Living the dream on the daily:
Wendy Mullin is a serial entrepreneur, death doula, filmmaker, and cleantech pioneer who doesn’t plan to retire

Occupations:

• Founder, Built By Wendy: multidisciplinary design studio for fashion, interiors, and other projects

• CEO & Co-Founder, Kiosk Mobile Utilities: a Los Angeles Cleantech Incubator startup, Kiosk is an all-in-one sustainable mobile utility providing renewable power, responsible waste management, water, first aid, communications, shelter and supplies for people working and playing on-location.

• Filmmaker: screenwriting and costume designer

• Founder, Departing Dearly: Funeral director and counselor and end-of-life doula

Age: 55

Location: Los Angeles

Previous locations: Brooklyn, New York, and Kansas

I’m in the midst of:

• Built by Wendy: I started this line while I was in college in Kansas in the late ’80s/early ’90s and it’s been going for over 30 years, but during COVID, I found it too difficult to do. I’m self-funded and it felt too stressful to invest my limited resources into clothing when the world felt/feels so unclear. I scaled back to just selling my tees and guitar straps.

• Costume design: So in 2022 I got into the Costume Designer’s Guild and started working on commercials and films to supplement my dwindling income from scaling back Built by Wendy. But to be honest, I don’t love it. I actually started my career in NYC styling music videos, so I thought it might be interesting to scope it out again since I live in L.A. and know lots of film people. I’ve worked on some cool stuff with great people like Marty Supreme most recently. But I find it stressful and physically exhausting. And dealing with racks of clothing is something I’m just kinda over.

  

• Screenwriting: I think partially why I don’t love costume design is because I actually love filmmaking, and screenwriting is more my thing. In high school, I founded my film club and made films and did photography, so my angle was always from that point of view. But I was kinda of a messed-up teen and ran away all the time because my family was having problems. That sort of derailed me and I ended up in a hospital where I taught myself to sew and that’s how I handled things. From there is how Built by Wendy happened. Anyhow, back in 2014, I wrote a teen John Hughes–esque dark comedy about it, which has been in development for the last year. We have a great cast attached and a director and it’s being packaged by UTA. So we’ll see!

• Sustainability and cleantech: Going back to 2022, I got interested in sustainability and was thinking about pursuing my next chapter in something that could create less waste in the world. I don’t love how much junk is out there, especially with clothing, which is partly why I don’t care about making clothes anymore. There are just so many clothes out there, which was not the case when I started Built by Wendy 35 years ago.
  
  So when I started working on film sets, I realized how wasteful they were and how inefficient the logistics and machinery was, so my partner and I came up with an idea for a sustainable all-in-one basecamp for film shoots, live events, disaster response… basically any off-grid situation where people’s needs and basic resources — shelter, seating, communications, water, first aid, bathrooms, power, and waste management. We are currently in the Los Angeles Cleantech Incubator as one of their portfolio companies and we are finally launching our first truck this fall.
  

  

• Deathcare: My main passion is really creating a new structure on how we deal with end-of-life and deathcare issues. My mom died in 2018 and realized there weren’t any modern resources that spoke to me and gave me resources, so I created a death and dying concept in 2019. Then in 2020 I built a website to share not only practical resources but cultural items for art, music, film, etc. that are deathcentric. I became a death doula as well. Then in 2025, I got my funeral director license and have been working at a funeral home and also developing a business concept for sustainable celebrations of life and funerals.

• Interior design: Last one! I have always designed my shops, but then in 2010 I started taking on interior projects for friends and still do by word of mouth. I’ve designed a few restaurants, offices, and homes, and sometimes assist my friend who works on fancy celeb homes. I love designing interiors and my dream is to one day build my own house. I can really make things look great on a budget, kinda like what I did with Built by Wendy.

I’d like to connect with:

As a lifelong entrepreneur, I love to engage deeply in things to see what is broken and where structures and systems could be done better. I am always looking for investors to help me take my ideas to the next level. I’ve always been a self-funded scrappy founder, but my current projects are on a bigger scale and scope and I need support.

About my relationship status and/or family:

I have one daughter, 15, and an ex-husband who co-parents with me. I also have a long-term partner. I love having them all in my life.

Follow me here:

hello-kiosk.com

builtbywendy.com

departingdearly.com

Linkedin

Instagram: @builtbywendy and @departingdearly

My superpowers:

Intuiting trends, deep-diving into a field, being fearless in trying new things and supremely on top of multiple pieces of information and being very organized.

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Need a craft genius? Jennifer Perkins has glue gun, will travel

Age: 51

Location: Austin, Texas

Occupations: Creative Content Designer, Author, and Kitsch Enthusiast

This sums it up in a nutshell, but a lot of people know me from different facets of my career. Once upon a time, people called me the Naughty Secretary, and now I’m often referred to as the lady with all the Kitschmas trees. Creativity has always been the common thread, but I have worn A LOT of hats. I tried to put these in somewhat of an order …

Past titles include:

• Owner, Naughty Secretary Club

• Co-Owner, Has Anyone Ever Told You? record label

• Host of Craft Lab for DIY Network and HGTV

• Host of DIY This with Jennifer Perkins for DIY Network & HGTV

• Co-Host of Stylelicious for DIY Network

• Co-Producer of Stitch Fashion Show and Craft Bazzar

• Content Creator: I Love to Create (Aleene’s Tacky Glue, Tulip Paints and Duncan Ceramics), Tuesday Morning Stores, Colorbok, Sakura, Michaels, JoAnn, Big Lots, Smoothie King, Slice, and more.

• DIY Editor for BlogHer network

• Brand ambassador, Treetopia

• Editor-in-Chief Kids Crafts 1-2-3 Magazine for Walmart

• Author of five books:
  • The Naughty Secretary Club: The Working Girl’s Guide to Handmade Jewelry
  • Creative Crafts for Teens: 25 Empowering Projects
  • Paper and Tape Crafts: 28 Inventive Activities for Kids Ages 8–12
  • Make Me I’m Yours Jewellery: Over 20 gorgeous necklaces, bracelets, earrings and rings
  • Upcycle It Crafts for Kids ages 8-12: Fun and Useful Projects to Recycle and Reimagine

• Monthly craft night host for Tom’s Shoes in Austin

• Host Creative Queso Podcast

• Workshop instructor

• Creative content producer for HGTV

• Afterschool art guide at Figment Creative Labs

• Proprietor of Jennifer Perkins Art and The Huntress Gatherer Etsy Shops

Follow me here:

Substack: Glue Stuff To Stuff

Instagram: @jenniferperkins

Linkedin

Website: jenniferperkins.com

Books on Amazon

I’m in the midst of: Planning my summer 2026. Piecing together a million side hustles, family vacations, and life is a serious puzzle. Plus, I am really trying to improve my Substack game and not ignore my social media accounts.

What’s next for me: Teaching online classes have always been a big goal for me, but they just seem so daunting. As a little girl, I remember my dad teaching me about “PIGs” — Positive Income Generators that make money while you sleep. I feel like online classes are a logical step in that direction for me, but, ugh, the idea of video editing and figuring out the backend makes me want to collapse in a pile with a bag of Nerds Gummy Clusters and a smutty audiobook.

Services I offer: I love being asked to teach and speak — have glue gun, will travel. I’ve taught craft classes from Los Angeles to Brooklyn and online for places like Creativebug and Michaels. I also do the occasional consulting and ambassador work.

I’d like to connect with: Geez, anyone and everyone. I love making new friends and connecting like-minded people.

My relationship and/or family status: I have been with my husband since 1998. We went to college together and bonded over our love of obscure indie rock and ’80s hair metal.

We just bought tickets to see David Lee Roth today but also pulled out an old Tortoise record on vinyl. We even had a record label together in the early 2000s called Has Anyone Ever Told You? (yet another side hustle that’s not on LinkedIn).

We now have two teenagers, one of whom is really into music. I shed tears of pride when something like Siouxsie pops up on her playlist or she wants to go see Pavement shows with me. My son is more of a gamer dude, though he has recently discovered The Cars and plays tuba in his school band.

My income: My whole adult life has been a combination of gigs. I tell people that some folks have one job that pays a certain salary and some of us have 15 jobs that pay the same salary. That being said, the amount on my taxes fluctuates wildly based on gigs I had the year prior.

Writing books, hosting TV shows, and contract content work pay the best, but I …

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Need a craft genius? Jennifer Perkins has glue gun, will travel

Age: 51

Location: Austin, Texas

Occupations: Creative Content Designer, Author, and Kitsch Enthusiast

This sums it up in a nutshell, but a lot of people know me from different facets of my career. Once upon a time, people called me the Naughty Secretary, and now I’m of…

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Lindsey Stanberry’s been around the New York media block and even worked on a book with Madeleine Albright. But the best thing she’s done for her career? Let’s dig in.

Occupation: Founder, The Purse; author, Money Diaries

Age: 44 (for a few more weeks!)

Location: Brooklyn, New York

Previous locations: I grew up in Cincinnati and went to college in Boston at Boston University, but I’ve lived in NYC for my entire adult life.

Follow me here:

Substack: The Purse

Linkedin

Instagram: @read_thepurse

I’m in the midst of: Trying to build a media business from the ground up while also studying to become a certified financial planner. And then there’s my personal life …

Most impactful career experience so far: Two things. One, running Money Diaries at Refinery29, writing the book and hosting the podcast. It was such a “pinch me” experience.

The second was managing a team of young reporters at CNBC through the pandemic. It was so hard. I was so stressed trying to juggle that job with raising a 3-year-old. We were living with my parents so we could have childcare support, and we were so lucky to have that support, but our lives were still so disrupted by everything that was going on in the world. I feel like I made a lot of mistakes during that time, but it also helped me grow as a manager.

My dream job: Running The Purse is my dream job.

I love to connect with: people who are interested in having open and honest conversations about money.

My relationship and/or family status: I’m married (16 years), and we have a 9-year-old son.

My income: Maybe it seems funny that The Purse is all about money, but I tend to not feel super comfortable sharing my finances publicly. Now, if we were sitting down to a coffee and you had specific questions, I might share, especially if I thought sharing that knowledge would be helpful to you. I tend to be pretty open in one-on-one conversations.

So without getting into specifics, I’ll say that I make most of my income from paid subscribers and some brand partnerships. From January to May 2025, I also worked a full-time temp job, and I tried to save a big chunk of that so I could spend the second half of the year completely focused on The Purse. My husband has a full-time job, as well, and we completely share our finances and expenses.

Monthly expenses in a nutshell: I’m lucky to be in a phase of life where we’re able to keep our expenses low, and that’s allowed me to take this risk and start my own business.

My son is in public school and we’re not paying for much child care at the moment. We own our apartment, and we benefited from being able to refinance during the pandemic and have a low interest rate. We paid off our car earlier this year. I try not to spend a whole lot on the unnecessary expenses that I enjoyed when I had a job that came with a regular paycheck (re: shopping for new clothes and paying for private exercise classes, for example). I’d guess beyond my mortgage, my biggest expense is groceries, and I’d estimate we spend around $1,000 a month to feed our family of three.

Primary personal debts: Slowly — so slowly — paying off our mortgage. We’re lucky that’s our only debt.

Retirement savings: Let’s just say it’s healthy! Beyond our low expenses, I’d say the second reason that I could comfortably take the risk and start my own business is because my husband and I were big savers for most of our 20s and 30s. We socked away money in savings and in our 401(k)s — and some is invested in a brokerage account — so we’ve been able to reduce how much we save recently while most of our earnings are funneled into paying our bills.

I would like to get back to a point where we’re able to invest more in retirement, but I feel good that we’ll get there.

Number of hours per week that I work: I honestly have no idea, but it feels like all the time. And with a lot of starts and stops built in. Most days, I work from 5:30 to 7 a.m., then from 8:30ish to 3ish, stop to pick up my son from school, then get back to work from 4:30 to 6ish.

I don’t usually work anymore after dinner because I’m too tired. I spend at least one weekend day studying for whatever class I’m in the middle of. Sometimes I’ll also work on Purse stuff on the weekends. Right now, it feels like too much because school/studying takes up a lot of time.

Where I work: I have a dedicated desk at a coworking space about a mile from my apartment. I work there three to four days a week, and often on weekends I’ll go there to study. If I’m not at the coworking space, I work from a small desk in my bedroom. My husband also works from home, and he works from our dining room table.

How I feel about the traditional 9-to-5: I don’t think I’m either pro or anti. I loved having a full-time job and going to an office every day. I’m one of the few people who misses office life before the pandemic.

I like the separation between work and my personal life. But I think …

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“Most of my jobs have been about growing and driving change, and it’s only recently that I’ve felt I have an actual playbook or blueprint to apply.”

— Molly Neuman, CD Baby President

Location: Los Angeles

Let’s connect here: Instagram: @mollydneuman @therealbratmobile

Linkedin • CDBaby.com • Bratmobile.com

Relationship or family status: I’m married to an awesome husband, and we’re about to celebrate our 13th anniversary. We have a 12-year-old daughter who is the light of our lives.

Career timeline

Bratmobile

Drummer (1991–present)

Lookout Records

Vice President, A&R and Marketing / Co-Owner (1994–2006)

Indivision Management

Artist Manager/ Co-Owner (2001–2006)

eMusic

Vice President, Label Relations (May 2006–June 2013)

Rhapsody International

Senior Director, Label and Publishing Licensing (July 2013–Aug 2014)

A2IM (American Association of Independent Music)

Interim President / Vice President (September 2014–December 2015)

Kickstarter

Head of Music (January 2016–November 2017)

Downtown Music Holdings

Global Head of Business Development (December 2017–October 2019)

Songtrust

President (October 2019–July 2022)

Downtown Music Holdings

Chief Marketing Officer (July 2022–June 2024)

CD Baby

President (June 2024–present)

Amy at The Midst: One of your earliest professional experiences was working as Vice President and Co-Owner of Lookout Records. Do you think of yourself as entrepreneurial, and if so, has that helped you in your career as a music executive?

Molly Neuman: I didn’t start my work in music with an entrepreneurial mindset, but more of an opportunistic one. I needed a job!

I had been touring a lot with different bands and none of them were really something I could support myself with, so I paused and got a regular job at a biotech company as a receptionist and shipping clerk.

My partner at the time worked at Lookout and things were really growing at a crazy rate there, but without much planning. They needed someone to help get things on track and my qualification was that I had worked somewhere else!

I jumped in and we cleaned the office, created some systems, and worked on ways to promote the current artists that were signed at the time. I think that spirit of jumping in, even when I didn’t really know what to do has carried with me in every role I’ve had in my career.

There’s always a foundation of relevant experience, but most of my jobs have been about growing and driving change, and it’s only recently that I’ve felt I have an actual playbook or blueprint to apply. Meanwhile, things outside of organizations change all the time, so adaptation, curiosity, and a bit of reckless ambition have all been key!

How do you think about the current state of the music industry?

It’s intense. There are so many people making music and so many more people connecting with it, but it’s so fragmented and siloed — it’s difficult for many to envision a sustainable career purely from making and performing music.

My basic advice for musicians is to make it because you love it and try to connect with people in genuine ways to see if it resonates and you can grow with it. There are so many options for musicians and songwriters now, it’s overwhelming. But there are trusted partners and ways to learn and make connections that are really incredible.

I recently discovered two interesting things about you. In high school, you worked for Arizona Representative Mo Udall. And in 2009, after graduating from the Chef’s Training Program at the Natural Gourmet Institute in New York, you founded a personal chef, catering, and health consulting company called Simple Social Kitchen. Tell us more!

Ha, yes, those things are true! I worked for the legend that is Mo Udall for two summers as a receptionist and aide, and there was, of course a little bit of nepo baby reality to that job. My dad had been his chief of staff and co-wrote a book with him called Too Funny to Be President.

It was amazing to be in Congress and meet people and learn a lot about communication and constituent support. Arizona, as you know, is an incredible state with so much history and so many complex dynamics; it was really a wonderful gift for me.

I went to NGI for their Chef’s Training Program when I was working at eMusic and wasn’t so sure a career as a digital music executive was the track for me.

I learned a lot about food and health and started a business to do catering and teach classes and be a private chef. It was rewarding, but really, it’s a tough job! Very physical, a lot of math, low margins in what you make, so I ended up closing that up after a few years. It was a side hustle, so I do feel like it’s something I have in my back pocket if I need to find a new gig someday!

Above: Watch “From Punk to Power: Thriving Through Change and Uncertainty” | Molly Neuman | TEDxBerklee Boston

Molly fills in the blanks …

My income: I’m grateful that I feel well-compensated in my work but know that there are so many ranges and factors that go into executive compensation. I also make a little bit here and there from my band, which is fun!

Monthly expenses in a nutshell: Mostly they’re around my kid, who goes to an independent school. Long story but when we moved to L.A., we didn’t know where we would live, so we decided on a private school that my husband had attended). It seems like a good fit for her. It’s an investment, but one we’ve decided works for our family. She does other activities like dance, Spanish, and acting, so there are a few other expenses there.

Other than that, we …

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“I’m the happiest I’ve ever been personally and professionally and I strongly attribute that to finally leaning all the way into my God-given purpose.”

L’Oreal Thompson Payton is a book author, bookstore owner, freelance writer, and yoga instructor

Age: 37 (until October 29, then I’ll be 38)

Location: Evanston, Illinois

Previous locations: I’m originally from Maryland, moved to Chicago in 2013, and had a very brief stint in Ohio from July 2021–March 2022.

Follow me here:

lorealthompsonpayton.com • Zorasplace.com

Substack: LT in the City Weekly

Linkedin • Instagram @ltinthecity and @zorasplace

I’m in the midst of: building Zora’s Place, a Black feminist bookstore in Evanston; writing my fourth book, an infertility memoir that will be published in spring 2027; and IVF for Baby No. 2.

I’d like to connect with:

• Event organizers and people hiring feminist authors and wellness advocates for PAID speaking engagements. Check out my speaking reel here.

• Editors looking for an award-winning health and lifestyle journalist to write cover and feature stories. View my portfolio here.

My income: As a freelancer, it definitely fluctuates. In 2025, I’m actually on track to make less than last year — and I suspect the various DEI rollbacks and state of media have something to do with that. I had way more speaking engagements and editorial assignments in 2024. I’ve yet to replace my full-time corporate income as a freelancer, but I definitely enjoy the flexibility and freedom that comes with it.

ABOVE: Watch L’Oreal Thompson Payton talk about her experience of overcoming perfectionism, and her book, Stop Waiting for Perfect, on the CBS Mornings Show in 2023. In December 2025, she will release Amanda Gorman: Poet and Activist (Step into Reading).

Monthly expenses in a nutshell: Our biggest expenses are definitely our mortgage and childcare, which is roughly the same (if not more) than our mortgage due to where we live. But the rising cost of living has made pretty much everything outlandishly expensive.

Primary personal debts: Mortgage and some credit card debt.

Retirement savings: Ooh, good question…I think I have roughly $75,000 from 401ks that have rolled over throughout the years from previous jobs.

Number of hours per week that I work: Probably more than I should. My “official” work hours are Tuesdays–Saturdays from 11–5 at the bookstore and Monday is my admin/errands day. I will say I’ve gotten better about not staying up super late working now. I need a solid 8.5 hours of sleep each night, so I try to be in bed by 9 or 10 during the week.

Where I work: Mondays from home (or co-working with friends at a coffee shop or the library); Tuesday–Saturday at the bookstore.

Pro– or anti–9-to-5? In terms of having a corporate job? I’m pro–do whatever you need to do to survive in this hellscape of a country/economy.

A typical weekday schedule in a nutshell: My husband, Jeff, works in downtown Chicago and is in the office five days a week. So most mornings, he’s up around 6:30 am and then I usually wake up around 7 before we get Violet up if she’s not already.

After everyone’s gotten ready, we’re out the door around 8. I drive Jeff to the train station and then drop off Violet at preschool. If it’s a Monday, I’m usually going to do our weekly grocery run afterward.

But in general, I work out, make breakfast, shower when I get home, and then start the workday.

On Mondays, I’m catching up on admin for the bookstore and placing that week’s order.

Tuesdays–Saturdays I’m at the bookstore. It’s still a little slow in the mornings, but usually picks up toward the afternoon.

Whenever there’s a lull, I’m answering emails or tackling client work. There’s a lot of multitasking going on throughout the day!

And in the evening, I reverse it all — I pick up Violet and then Jeff. He’s the cook in our family, so he’s the one who makes dinner while Violet and I are playing, watching TV, or calling my family on FaceTime.

Jeff also does bedtime duty and I typically go to bed around 9 or 10 pm.

On the weekends I’m usually: On Saturdays, I’m at the bookstore from 11–5. On Sundays, we try to go to church in person, but if not we’ll watch it at home. And then depending on the season, there’s usually some kind of extracurricular activity for Violet. This fall and winter we’re doing ice skating lessons and tap/ballet classes.

Relationship status: Jeff and I have been married for 10 years (it’ll be 11 on November 1). We celebrated last year with a trip to St. Lucia and it was ah-mazing! He’s the most patient man I know besides my dad.

Violet is our little Libra/rainbow baby. We had several failed embryo transfers before she was conceived and it was such an arduous mental and physical process. But she’s here now and she lights up our lives, while simultaneously keeping us on our toes.

I see a lot of me in her — inquisitive, ambitious, and determined. Plus we both love books and reading!

My superpowers: Storytelling, for sure. And also building community. I feel fortunate to be able to do both in my work as a writer and now, as a bookstore owner.

How much my career is tied to my identity: Whew, if you had asked me this question a few years ago, they would’ve been synonymous. But after a very telling performance review wherein I exceeded every metric given to me and only received a “met expectations,” I realized the goal post was always going to keep moving. Nothing I did would ever be enough. I was tired of working twice as hard to get literally half as much, so I put a plan in motion to quit and by that fall I was out.

So these days I would say my career is a complement to my identity, rather than synonymous. I very much identify first and foremost as a writer. But now instead of working myself into an early grave trying to meet (or exceed) impossible metrics, I’m leaning more into the purposeful part of my writing rather than allowing it to consume me.

My happiness meter, out of 10: Hmm, honestly? Happiness with my life is probably a 9.5. I’m the happiest and most satisfied I’ve ever been personally and professionally and I strongly attribute that to finally leaning all the way into my God-given purpose. All things considered, our family is also in a good place. Could we use more money? Absolutely. So can everyone. Everything is so expensive now. And we have our health, so I like to think we’re rich in other ways.

Now my happiness meter with the state of the world? At the moment, probably a -1,000. Especially given what happened with ICE in Chicago. The stories and videos make me sick to my stomach. I vacillate between heartbreak and outrage every five minutes.

Hopeful retirement age: What retirement? I’m gonna be like Toni Morrison and write until the end.

Peri/menopause experience and advice: Well, my doctors haven’t officially diagnosed it, but based on everything I’ve been reading and seeing online, I’m about 95.5% sure I’m perimenopausal. Which tracks. I got my period when I was like 8 and it’s been downhill since then.

My experience so far, like most others, has been sweaty. It didn’t help that I was diagnosed with endometriosis earlier this year and the treatment for that was two months of lupron depot, which essentially sent my body into early menopause in preparation for our next embryo transfer.

Honestly, I’m advocating for a hysterectomy after this next kid. I’m done, I’m so over it. I know that won’t eliminate/allow me to bypass the menopause symptoms, but at least I won’t have to worry about bleeding out every month.

Healthy habits: I’m pretty consistent about journaling, meditating, and working out. I’m a certified yoga teacher and I teach a class once a week and do strength training about three times a week.

Not-so-healthy habits: Overdoing it. I definitely pack more into a day and onto my to-do list than is reasonable for one human being, but I’m doing my best to uncouple my productivity and my worth.

Best investment: Therapy. … Hands-down. And my Peloton.

Worst investment: …

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“I’m a formerly hard-charging GenX’er who basically murdered myself and factory-farmed my creativity in an attempt to achieve my way into happiness. Shocker: it didn’t work.”

Age: 49

Location: Portland, Oregon

Previous locations: Born in Winchester, Massachusetts; college in St. Paul, Minnesota; San Francisco during the first dot-com boom; Los Angeles for 14 years; moved to Portland in March 2020, arriving on the day everyone freaked out and bought a year’s worth of toilet paper.

Follow me here:

• Instagram @emilyonlife (but I’m rarely active there)

• Linkedin

• Substack: Subject to Change

Subject to Change with Emily McDowell

Cautionary tales, unsolicited advice, and notes on living in liminal space, evolution, and returning to yourself.

• emilyonlife.com

• thegreatergoodsalliance.com

I’m in the midst of: Navigating Long Covid that caused a reactivation of Epstein-Barr virus. I’ve been ill for about nine months, and confined to bed for about two months of that: in March 2025, and then again in June. I’m constantly negotiating how much energy I have and whether I’m doing too much and setting myself up for a flare.

I’m also in the midst of reinventing my career and identity. I’m a formerly hard-charging and ambitious GenX’er who basically murdered myself and factory-farmed my creativity in an attempt to achieve my way into happiness. Shocker: it didn’t work.

In 2022, the stationery brand I founded, Em & Friends, was acquired by the publishing arm of Barnes & Noble, and I left the company. I had a strict two-year non-compete agreement, so I spent that time consulting with them, staring into space and wondering who I was, healing from clinical burnout, doing a lot of breath work, and studying transitions and liminality.

Truth be told, I still don’t entirely know where I’m going career-wise, or what my future contributions to the world might be. But after four years of leaning into the lost place (well, two years of desperately clinging to my former life and two years of leaning in), I don’t look at those questions as problems to be solved anymore, or judge myself for not having solved them.

In April 2024, I launched my consulting and coaching offerings, then my mom died in June, and then I got Long Covid/EBV. So I’m in the midst of learning to work in a completely different way, by both choice and necessity, that puts my body’s needs first, minimizes stress, and aligns with my intuition instead of society’s definitions of success.

My income: A lot less than it used to be, but enough. I’m very fortunate to be able to replace some of my former work income with investment income.

Monthly expenses in a nutshell: My biggest expense is health care: I’ve spent $36,000 on medical expenses in the last year, including insurance premiums, copays, meds and supplements, and practitioners who don’t take insurance. Beyond that, my mortgage and regular household expenses. I spend money on fancy groceries and DoorDash, a couple trips a year, and charity/mutual aid. I have twin 18-year-old stepsons, but most of their expenses are covered by my partner and their mom.

Primary personal debts: Just my mortgage. I’ll never forget how amazing it felt to pay off my undergrad debt at 37.

Retirement savings: When people hear my brand got acquired by Barnes & Noble, they often assume I made F-U money. I made around $2 million, which is freaking wonderful, but I’m not buying yachts anytime soon. I also lived below my means and put money away for the last 15ish years, so I’m in very good shape for retirement. I didn’t grow up with wealth, so investing was a total mystery to me; I wish I’d started it sooner instead of keeping all my savings in my checking account for seven years!

My office: I’ve been working at least part-time from home since 2011. During the Em & Friends years, I was in our Los Angeles office a couple days a week until I moved to Portland in 2020.

Relationship status: Engaged! We met the week the pandemic hit, so our options were to never see each other again or move in together and start bleaching our co-mingled groceries. Lucky for us, it worked out.

I’d like to connect with: People who resonate with my story, folks hiring for speaking gigs (I love doing this and want to do more of it, especially virtually), cool and interesting and curious people in general, potential clients.

My consulting work: I offer strategic, creative, and emotional support to product business owners, both one-to-one and in a group program called The Greater Goods Alliance that I co-lead with Lisa Congdon.

My clients also include entrepreneurs who don’t necessarily sell products, but feel called to work with me; I’ve helped folks write websites, clarify their offerings or design new ones, decide to close or pivot their businesses, and navigate life transitions and liminal space.

I especially love working with product business founders because a decade-plus ago, when I needed a “me,” I couldn’t find one. I hired plenty of consultants over the years, but each one specialized in one or two aspects of what I needed to know: how to prepare a wholesale collection and work with retailers, or how to put together a warehouse, or how to exhibit at a trade show. I didn’t have a creative thought partner for product development. There was nobody I could work with who could help with all the facets of my business, and nobody to learn from who’d actually done the thing I was doing, at the scale I was doing it.

Now I AM that person, and it brings me great joy to share everything I know. This includes helping people clarify exactly what success means to them, and discerning what they actually want, not just for their business, but for their lives— and help them make a plan to get there. I wish I’d had someone to help me with this 10 years ago, too.

A typical weekday schedule in a nutshell: I need like 12 hours of sleep, so I sleep late. I’ve never been a morning person anyway, and at 49 I’ve just embraced it. My morning routine is “being unconscious.” It’s fine.

I get up, make a coffee, put some collagen in it for luck, usually drink it in front of my computer. My work all happens over Zoom and email, at random times; I’m working very part-time at the moment, so I don’t protect certain hours, but I do when I’m busier.

I have a lot of appointments – naturopath, various docs, therapy. Right now, I look at taking care of my health as a job, and I’m very aware and appreciative of having the privilege to do that. I try to see local friends a few days a week, and connect with faraway ones regularly. I make dinner or order in. My partner and I get in bed early and talk; that’s our primary time to connect. We watch dumb TV and provide running commentary.

On the weekends I’m usually: See above, minus the Zoom meetings.

How much my career is tied to my identity: Oh my god, at this point, zero, which is really wild. For more than 20 years, my career was synonymous with my identity – first, in working in the creative departments of major ad agencies, which was so demanding that it essentially required us to collectively brainwash ourselves into believing we were CHANGING THE WORLD, therefore making us willing to regularly pull all-nighters and work through holidays to sell more pizza and car insurance.

I left advertising to start what would become Em & Friends, which pushed me even deeper into identifying with my career, which is the natural outcome of naming the brand after myself, publishing products from my ideas, and creating a brand identity that was based on my personality. Who knew?!

I don’t think it’s inherently problematic to tie one’s career to one’s identity, but for me it definitely contributed heavily to my burnout. When I left Em & Friends in 2021, a huge piece of the work in front of me was detangling and disconnecting my identity and intrinsic worth from what I put into the world, my productivity, and what I’d been publicly known for. I feel infinitely more …

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Location: Arvada, Colorado

Previous locations: All across the Midwest from 1978–2001

Join my community: MidCircle from Her Stories Project

Follow me here: stephsprenger.com • Instagram • Linkedin

The Reclamation Era

The intersection of midlife, single motherhood, and neurodivergence

By Steph Sprenger

I’m in the midst of: Revising and shopping around my memoir, curating an anthology of anonymous divorce stories for Redacted: What Divorced Women Aren’t Telling You, facilitating creative writing workshops for midlife women, and producing storytelling and comedy shows for primarily female audiences.

I produce Listen To Your Mother Boulder, which is a national brand that cities can franchise, and I produce a few different comedy shows — Comedy Coven, which is an all-female lineup — and I'm My Therapist's Favorite, which is a more relatable, vulnerability-focused lineup.

My income: Sooo variable, which is the least fun part of being self-employed. My income fluctuates based on the season, current shows I’m producing, which workshops I am running, and how many clients and students I have. The flux can be incredibly stressful.

Monthly expenses in a nutshell: My mortgage, all the bills for a household where I am the sole caregiver for my teenage girls, college expenses for my oldest, and any business expenses I have for productions — venues, marketing, etc.

Primary personal debts: I just paid off my car, hooray! So, just my house, and fortunately I have minimal expenses for my college student at the moment thanks to scholarships. One of my greatest sources of gratitude is that I do not have credit card debt. It helps me sleep at night.

Retirement savings: I have some. Thanks to my ex-husband’s “regular job,” we were able to save considerably during our marriage, but not as much as I would like. Being a self-employed single parent is scary; I find it incredibly difficult to contribute to my retirement savings at the moment with all the flux as well as having a college student.

Work remotely, from home, onsite, etc.? I primarily work from home, which I love. I teach voice lessons to adolescent girls out of my home, and my writing/teaching/producing is all done from home. My shows, auditions, rehearsals, etc. are all held at other locations, and that is a welcome treat. But to be honest, working in bed will always be my favorite — and probably most productive — place to get things done. I notoriously set up camp in my California King with my laptop, planner, and notebooks next to me where my husband used to sleep, a pillow under my knees, heating pad on my back, and rescue dog fighting my MacBook for my lap.

Relationship status: I’ve been separated for just over two years; my divorce was final in May 2024.

I’d like to connect with: Midlife writers in search of community, divorced women interested in reading or submitting to Redacted, and most importantly, A LITERARY AGENT! Seeking representation for a memoir is not for the faint of heart — it is a humbling experience requiring tenacity and maybe a touch of insanity.

I am always looking for writers to join MidCircle AND we are always looking for guest presenters to submit applications. We offer 2–3 monthly guest workshops about writing, publishing, midlife women's health, etc as part of our membership community.

A typical weekday schedule in a nutshell: Every day is a little different, which is both fantastic (fun!) and challenging (overwhelming!) for my perimenopausal ADHD brain. I typically start my day with journaling and meditation, try to squeeze in a workout when I can, and usually have virtual writing workshop meetings or co-working sessions in the first half of the day. I do my best, focused writing mid-morning, and I often spend afternoons editing, reading submissions, writing newsletters, interacting in workshops, and returning emails. My late afternoons-early evenings are for teaching voice students and spending time with my teenager. During a show season, I will have occasional auditions, rehearsals, or performances in the evening.

On the weekends I’m usually: Trying my best not to work while also squeezing in a little time to get some work done to prevent an avalanche of overwhelm on Monday. When my daughter is occupied, I’ll sneak to my bedroom to write or work, but otherwise, we spend time relaxing together, having adventures, or binge-watching our current favorite series (We’ve blown through Schitt’s Creek, Ted Lasso, Stranger Things, Only Murders in the Building, and Ginny and Georgia, and are currently making our way through Gilmore Girls for her first viewing and likely my tenth). I am fortunate to have a small handful of amazing best friends, and almost every weekend involves time with some of them. That’s the beauty of having older kids; friendship becomes more center stage again.

How much my career is tied to my identity: Oh, so much of it. So very much. My website’s tagline is “Leading women back to themselves, one story at a time,” and it truly feels like my life’s purpose. Being an essayist and memoirist means that my art is essentially my life, and with my workshops, shows, and 1:1 clients, I feel like my mission is to help other women find their voices. Curating women’s stories is my passion, and I feel like my work is just an extension of who I am as a person. As I type this out, I can’t quite decide if this is a good thing or a bad thing. Will I be one of those people who never really retires? Maybe. Actually, scratch that; I adore being lazy.

My happiness meter: Despite a harrowing couple of years, I am a tremendously joyful person at my core. Joie de vivre is my trademark vibe, and I feel grateful that I am able to tap into contentment, connection, and a sense of purpose even when I feel like my world is one fire. I’m just going to go ahead and knock on wood now.

My superpowers: My ADHD gives me some inherent superpowers: my hyper-focus is legendary. This is not always a good thing, as I forget to eat and check the mail, but it is a terrific creativity aid. I am intuitive and creative, but I think my biggest superpower is that I am a connector of people. I think I am especially good at bringing out the superpowers of others, helping writers tap into their authentic voice and find the heart of their stories.

Hopeful retirement age, if at all: Ha! See above. Honestly, I would prefer a “soft retirement,” where I continue to write, facilitate workshops, and produce and perform only as it suits me. That would be ideal. A balance of family, friends, and relaxation with doing the work I love so much as I hit my sixties would feel like a life well-lived.

Peri/menopause journey: Oh, lord, this is a fun one. Pro tip: Carry a perimenopause emergency kit in your purse with tampons and spare underwear lest you find yourself having a Code Red situation at the art museum with your kid (yes, that happened last week). I have learned that perimenopause + ADHD makes for a roller-coaster of emotional dysregulation and sleep issues. Currently, I am using low-dose estrogen patches and taking oral progesterone, and it’s been a game-changer. I’m 47, and my cycle shows no sign of stopping, although it really enjoys f***ing with me with unpredictable, vexing rhythms.

Healthy habits: I’ve tried really hard to start exercising regularly again after the divorce. Doing yoga and pilates, hiking with my dog, and doing short strength training workouts at home. I am a sleep champion and after beginning HRT and trying to get my single parent cortisol tamed, I’m finally back to sleeping 8.5-9 hours a night. I journal and meditate every day, and have pretty firm morning and evening rituals that feel like self-care vines I grab every single day.

Not-so-healthy habits: I stay up way too late with my youngest daughter. When high school starts in a few weeks, with a much earlier morning bell than middle school, we are screwed. I do not meal plan or cook as often as I should (could!!), and keeping a tidy house is not a forte for this ADHD family. I like to pretend that the laundry basket and mail box do not exist.

Best investment: Leaving my marriage may not sound like an investment, but it was. It was an investment in myself, and the bravest thing I ever did. I jumped, and there was no net. I was the net.

Worst investment: That really expensive industrial vacuum I bought from a door-to-door salesman in my twenties. It felt like a marker of adulthood. It was not. I sold it on Craig’s List for a fraction of the price five years later.

Any career regrets? Sometimes I wish I had gotten an MFA to combat my impostor syndrome and give me more street cred. I’ve always felt self-conscious about my cobbled together career, which began with a degree in music therapy that I only use for a small portion of my work. Sometimes I wish I had a more traditional writing career, that I’d done it the “right way.” But I honestly don’t think I would change it. My meandering path was hard-won, and made me the person that I am. Finding my voice, learning for myself, and fighting for a career that works for me has taught me immeasurable lessons about authenticity and resilience.

Best thing I’ve done for my career: Started blogging — despite my tremendous discomfort with the self-indulgence of it all — after my youngest baby was born. It brought me back to myself and was the first step of opening doors towards publication and creating community for women writers.

Most impactful career experience so far: Producing Listen To Your Mother Boulder. Again, curating women’s stories is such an honor and the biggest joy of my career.

My dream job: Getting my first memoir published and continuing to write more books. I would love to have my publications be a platform where I can reach more women through speaking and facilitating workshops. And god, if I could get paid to write all the time, it would be an absolute dream.

How I’m using AI (if at all): I often ask ChatGPT to help with wording for calls for submission or give me ideas of places to pitch for marketing. I cannot believe how helpful it is for brainstorming and thinking outside the box. I use it personally as well, for things as varied as “should I refinance or sell my house?” to suggestions for how to navigate co-parenting nightmares. I use it for researching Substack pieces as well. I love it.

My career timeline in a nutshell

I graduated with a degree in music therapy and music education in 2000.
From 2001 until 2023, I was in private practice as a music therapist, working primarily in early childhood settings, facilitating parent-child or preschool music programs.

2012: I began blogging and submitting my work for publication

2013: I auditioned for Listen To Your Mother Denver, and created The HerStories project writing community — publishing five anthologies in a decade and offering numerous writing and publication opportunities for women — with my co-editor Jessica Smock.

2016: I began producing LTYM Boulder in addition to continuing my part-time music therapy work, writing, and HerStories Project work.

2023: I quit most of my early childhood music classes, began teaching voice lessons to adolescent girls, wrote my memoir, began stand-up comedy, and got a divorce. You know, the usual midlife crisis stuff.

Beyond the polished titles and curated career updates, there’s the real story — messy, multi-dimensional, and inspiring.

“What Linked in Doesn’t Say” dives into the truths behind professional lives: relationships, income, career pivots, money lessons, and the moments you won’t find in a LinkedIn profile. Because there’s more to career evolution than what’s on the résumé.

Stephanie Sprenger is a member of our Founding MidstHer community.

Age: I’m an amateur 62-year-old, and an aging person in training.

Location: Los Angeles

Previous locations: My roots are in the (510) East Bay. Short stints in San Francisco and NYC.

Follow me here: Instagram • Facebook • Linkedin • heymiddleage.com

I’m in the midst of: Assisting two aging parentals, about to start writing again on my dormant blog (and maybe Substack), learning new editing skills, and navigating thinning brows (tips welcome). Caring for three resident cats and three foster kittens. Cat energy is essential for life.

My income: Moolah fluctuates. Content creation started as a hobby, but now it’s my job. Fortunately, income has increased every year since I started. There’s no roadmap so I’m learning as I go. It’s super exciting and creative, and nothing I ever imagined would happen.

Monthly expenses in a nutshell: Mortgage, taxes, groceries, insurance, retirement accounts, investments, pets, eating out.

I used to be a fashion-obsessed shopper; I followed every trend in clothes, shoes, beauty products, hair, and nails, but since I don’t work in an office anymore, that spending has decreased to a sliver of our expenses.

The most unexpected spending has been insurance, which increased for our home, cars, and health threefold in the last couple of years.

I have multiple subscriptions because I love streaming (current faves: PokerFace, Hacks, Stick, and I can’t wait for Slow Horses season 5). Also coffee. Cannot live without my Nespresso.

Primary personal debts: Mortgage. I haven’t had any other debt for over three decades. I did a lot of foolish spending in college and in my 20s, so I had a lot of credit card debt. Once I paid it off, I vowed to never have unproductive debt again.

Retirement savings: On track, but it never feels like enough, since the cost of life keeps increasing. I don’t have plans to retire, but that’s by choice.

Work remotely or onsite? Remote, and anywhere I need to shoot content.

Relationship status: Married for 35 years

I’d like to connect with: Women who are experienced in the content creation world who want to hang out, share advice, and support each other.

A typical weekday schedule in a nutshell: I set my own schedule, which isn’t just a luxury, it’s essential — more on that below.

My only flex is that I wake up to no alarm, so I sleep late.

I quickly scan emails and Instagram from bed, down a big glass of water, slap on sunscreen, then take a quick walk. Breakfast is always free of refined sugar — usually berries, plain Greek yogurt, nuts, and a Nespresso with Nutpod creamer. Then it’s emails and content creation: concepts, writing copy, stories, and planning. Late mornings are for meetings.

Around 1 pm, if it’s a home workout day, I’ll do strength training or an online shuffle class in my garage. On boxing days, I hit the gym in the late afternoon.

I’m on the socials throughout the day scrolling, posting, responding, and searching for cool content and music. Social media has its issues, but for me it’s been hugely positive. Instagram connects me globally, giving insights into midlife experiences — the joys, frustrations, and triumphs. I keep things uplifting because there’s enough negativity elsewhere, and I block if needed without hesitation.

Dinner at 7 pm (I cook three to four times a week), then content editing after streaming a show or two with the fam. My best creative energy hits around 9 pm, so I stay up late working.

Each week, I make time for something social like coffee dates, Zoom chats with Instagram friends, lunches with new connections, and midlife-focused events or brand activations. In Los Angeles, that usually means driving an hour or two each way, but it’s usually worth it.

Sometimes I feel like my days lack depth, but I know I make a difference to the person who needs a nudge to start physical movement or change the way they feel about aging because I get messages, including very vulnerable ones, every day.

Also, I’ve got two aging parents who need support. One lives nearby, so I’m on deck for doctor appointments and errands. My dad’s a quick flight away, and I visit to give his caregivers a break. Last year, I spent a total of eight weeks with him. That time? A gift. I know most people don’t get that kind of window. I didn’t have that kind of time with my mom, and it’s my biggest regret. So now, I build my schedule around what really matters — and this matters.

On the weekends I’m usually: My fave start to the weekend is a boxing workout on Saturday morning. If I do some hard work, and get a good sweat on, I have energy for the rest of the weekend.

Lately the husband has been finding places to eat on Instagram so we’ll check out a new place outside of our neighborhood. In the last month we had sand coffee, super yummy Hawaiian/Korean food, and soft-serve ice cream with fancy toppings.

My Sunday morning ritual since college: the entire New York Times in print and a big latté.

Since I work at home, errands and chores are spread out over the week, but I used to cram them all into the weekends.

How much my career is tied to my identity: I lacked a career for so long that I’m used to, and very comfortable with, not being identified with a job.

My happiness meter: Fulfillment is the goal more than happiness, and as I get older, it comes from gratefulness, less self-criticism, physical well-being, and leaning into friendships.

“Fulfillment is the goal more than happiness, and as I get older, it comes from gratefulness, less self-criticism, physical wellbeing, and leaning into friendships.”

My thankfulness meter is a 10/10 every day.”

My career trajectory: Lukewarm with no direction until I was in my mid-40s. At 62, I feel limitless.

My superpowers: I can start a conversation with anyone — in grocery-store lines, on airplanes, or waiting to pick up my pizza. I’m generous with compliments. Brief human interactions are spirit boosters.

Hopeful retirement age: Retirement would make me blah and lazy, so I don’t plan on it. I’m lucky: I travel enough that I don’t need to retire to travel. I have a flexible schedule so I don’t need to retire to do what I want.

Peri/menopause journey:

I listened to a podcast about Boomers feeling frustrated because we’re the generation hit hardest by the Women’s Health Initiative, which essentially took menopause hormone therapy (MHT) off the table. That’s me — I’m at the tail end of that group.

I’d heard the word “perimenopause” but had no clue what it really meant. Looking in the rearview mirror now, I realize many symptoms I experienced like frozen shoulder, brain fog, and insomnia were probably perimenopause-related, and I just didn’t know it.

When I was 60 — eight years after menopause — I started MHT to prevent osteoporosis, right at the supposed “cutoff” age.

An unexpected bonus? Within a week, the full-body joint pain I’d been living with for years vanished.

Healthy habits: I’m super active. Boxing training sessions two to three times a week, online shuffle classes, yoga, walking, step, strength training, and floor mobility work.

After menopause my A1C kept rising, so I’ve cut back on sugar dramatically.

I don’t drink alcohol (Asian glow IYKYK).

I’m all about aging with healthy feet. A year ago I partnered with Vivobarefoot and it’s official — I’m a barefoot shoe believer. Most people, even health enthusiasts, wear unhealthy shoes. Barefoot shoes keep my feet strong, improving balance and mobility. Drop a comment if you have questions. (To save 20% on the U.S. site, enter code MIMI20. Code doesn’t apply to sale items.)

I’m also in a text group doing NYT puzzles — we rotate choosing the Wordle word and share our Connections results. Throughout the day, I tackle The Mini, Strands, and Letter Boxed. It's mainly for fun, but I suspect it's good for memory and keeping my brain sharp.

Not-so-healthy habits: I use my devices until I go to sleep.

Best investment: Exercise, now and always for today and for later life.

Worst investment: Years ago …

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A self-described recovered workaholic, Jaime Derringer, 46, still has energy to grow a new startup

Location: San Diego

Previous locations: I’m a Jersey girl, through and through

Follow me here: Instagram @jaimederringer • Linkedin

Blob

i'm whatever you want me to be

By Jaime Derringer

I’m in the midst of: growing a new company, TRAME, raising a teenager, approaching menopause, and rediscovering myself. I started perimenopause in my mid-30s, having no idea what I was dealing with and feeling very alone. Now that I’ve talked to more and more women about it, it’s been such a relief to have support from so many.

I’m in my third career act, but still have the energy left to help grow a startup. I feel really lucky to have been able to follow my passions for most of my career, essentially inventing jobs for myself as I go.

My income: I’m compensated fairly, although you can never really make enough money when you live in California.

Expenses in a nutshell: All the typical expenses of any family! I admit, though, that we splurge on food delivery often because we both hate to cook and have zero time for it. We also splurge on at least one amazing vacation per year. And we have a lot of hobbies, so any extra money usually goes right into our hobbies and, of course, the savings account.

Primary personal debts: Our mortgage is our largest debt, and since we live in the suburbs, we also have two cars.

Retirement savings: I have been self-employed for so many years that I’ve been really good about ensuring I put away the maximum that I can each year into my SEP. I know how much I put away each year, but never look at the total because I don’t want to be tempted to touch it before I retire.

Share The Midst

Work remotely or onsite? Remote all day every day since 2009. I love working from home.

Relationship status: Married with one child

Partner’s age and profession: My husband, Jordan, is 48 and is an attorney. He’s always been very supportive of me doing my own thing, and I’m so grateful to spend my life with someone who would let me quit my day job to become a full-time blogger when blogging was barely even a thing yet!

I’d like to connect with: People interested in technology, art, design, philosophy, the humanities… books, movies, music… creative people! Business people, too. I don’t know — I usually learn something from everyone I meet!

Available for: Speaking engagements and board/advisory seats

A typical weekday schedule in a nutshell: I have been working from home since 2009. I used to work all the time, especially in the early days of Design Milk, but now I work more traditional hours. I’m online early since my co-founders are located in Paris, and usually finish my day somewhere around 5 pm. I am very entrepreneurial, so I’m typically available any time, but I try to have stricter boundaries when taking time off or spending time with my family.

I used to be a workaholic, and it took me a few years to undo the behaviors that were literally making me sick and anxious. I feel so much better now that I have a better balance.

I do some sort of physical activity every day. I lift weights four times per week and I walk almost every day. I try to get 10K steps per day. It is really hard to do that when you work on a computer so I invested in a folding treadmill that I walk on while I work. Better than nothing!

Also, I sleep at least 7–8 hours every night. Sleep is something that is non-negotiable for me. I stop using my phone before bed, which has helped me fall asleep more quickly.

Ideal schedule: I would like a four-day work week, please!

On the weekends I’m usually: Making art, walking, and reading. I have a lot of hobbies, so all of my free time goes into them when I am not working. I have been doing a lot of weaving lately, but also lots of drawing. While I do these things, I’ll almost always be listening to an audiobook. I read about five books per month, ranging from sci-fi to memoirs.

How much my career is tied to my identity: 50–60%. I used to be at 100%, so I feel like …

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Top of mind by Amy Cuevas Schroeder

1. Oprah + some of the first ladies of menopause

Years ago, Oprah was one of the first people to talk openly about peri/menopause with the masses, and she’s continued to bring the topic to the forefront on TV and in her magazine and website.

On March 31, she hosted a new special with Halle Berry, Naomi Watts, Maria Shriver, Mary Claire Haver, MD (an ob-gyn and the author of The New Menopause), and Rhonda Voskuhl, MD, a neurologist who specializes in menopause.

Halle Berry talks about how she thought she’d skip menopause altogether:

Oprah's Menopause Revolution

2. ‘The GenX Career Meltdown’ story in the New York Times hits close to home

As a career-long creative who’s worked in media and advertising, Steve Kurtz’s March 28 NY Times piece accurately describes the career shift that many of us GenXers are going through right now. It’s true: just when we should be at our peak, experienced workers in creative fields find that their skills are all but obsolete.

On the one hand, I think the doom-and-gloom alarm story will help GenXers talk more openly about our career struggles. On the other, I don’t want us to give up, my friends.

I like writer Terri Trespicio’s take, from her recent newsletter:

[Steve Kurtz] describes Gen Xers as the people who were training in candlemaking when electricity was invented.

I get it: The things we invested heavily in learning and worked hard to do don't happen anymore: Huge-budget shoots. Paste-up text. Hand-made illustrations. Living comfortably on a journalist's salary.

We don't rely on candles for light anymore. But I still have some around, don't you? They still play a role, even if it's not to see by.

Also: Would you really want to go back to no electricity? Of course not.

I always dreamed of being a magazine editor, and then I was one—and then, I wasn't.

There was never a guarantee that our jobs would stay the same, or that anything would be the same. Do you regret the skills you learned? I don't.

And why should we? The world may feel like its on fire, democracy in a death spiral — but we still are living in a pretty unbelievable time. And learning what we did helped shape who we are today.

We have access to things we never did before: Low-cost tools and low barrier to entry, basically free platforms on which to build brands and work of our own imagining. The tech that allows us to work with anyone, anywhere, anytime we want. Plus, no end of things we can learn — without going into debt learning it.

You're not old. Show me someone who says they are and I'll show you someone who stopped learning years ago.

I realize you may not agree with me. That's fine.

Just remember what Gay Hendricks says in The Big Leap: “If you argue for your limitations, you get to keep them.”

Meet Roma van der Walt: CEO of Vitelle, ‘geriatric mom,’ and female longevity aficionado

Santa Monica, age: 43

File under: women’s longevity, female sports, science and tech, seeking funding

Let’s connect here: Instagram • Linkedin • vitelle.co

I’m in the midst of: launching our B2B startup’s first customer pilots. Vitelle is a health intelligence platform providing digital health companies with the insights and analytics around their core product to improve their customer engagement, care coordination, and continuity of care. I lead a team of seven remote and some fractional team members. They are incredible.

Previous locations: In backward chronological order: Adelaide, Australia for 1.5 years; Sydney, Australia for two years; NYC for 15 years; Cologne, Germany for five years; and prior to that, Bavaria.

Relationship status: Married with children

Partner’s age and profession: My husband is 51 and the breadwinner. When we first met, I was in a high-income bracket working at the United Nations despite being younger. He is very supportive of my ambitions. Not just work but also when I am dared to do crazy sh*t — like when one of his friends dared me to run a 27-mile ultra marathon four months postpartum with 4,500 feet of elevation gain.

My husband took the kids, kissed me goodbye, and watched me beat his friend and come back happy after having some well-earned me-time on the mountain.

My income: is a roller coaster and as founder and CEO, I pay myself last. I have learned that there are a lot of myths about how much and how quickly founders can pay themselves, and I am very realistic about how much black women have raised in the U.S. (less than 300 black women have raised $1 million or more).

Expenses in a nutshell: I grew up without a lot and am proud of the life we’ve built for ourselves and our kids. My husband and I have poured a lot into my decision to build this company, so the past years have been lean. We have some incredible angel investors that supported Vitelle early on and in 2024, Techstars Boston invited us into their program. Most of our pay goes toward rent, car loan, childcare, cost of living. Gone are weekly date nights.

Primary personal debts: I’m lucky as a German to not have student debt, but the past years of bootstrapping have meant accumulating some personal debt.

Retirement savings as of December 2024: not comfortable saying

Work remotely or onsite?
Remotely at home and will co-work with friends from time to time. I love meeting my friends who are freelancers or fractional at spaces to work side by side.

A typical weekday schedule in a nutshell*

• 7–7:45 am: Get the kids out of bed, fed, dressed, and into the car with their dad to drive to school.

• 8 am–4 pm most days: At my desk for meetings and working on sales, partnerships, and fundraising.

• 4:15 pm: Pick up kids from school, rush home, manage the toddler’s emotions, and make dinner.

• 7 pm: Often back at the computer until about 8/8:30 pm

• 9:30 pm: Bedtime

• *Not mentioned: Picking up stuff nonstop, organizing groceries, lunch boxes, laundry, dealing with sicknesses and extracurricular activities

Ideal schedule

I wish I had time to exercise before the kids get up. It happens some mornings but it’s short.

I also need to schedule more mindfulness into my life and walk more. I don’t live in New York anymore and our dog died last year.

How much my career is tied to my identity:

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Meet Tamara Warren, 49, living in Brooklyn for 21 years

File under: entrepreneur, journalist, car expert

Let’s connect here: tamarawarren.com • lecar.co • Linkedin

Instagram: @tamarawarren @lecarco

I’m in the midst of: writing a book, building a company to empower women through education about cars, keeping up my chops in multi-media journalism, and producing a documentary film.

Available for: Speaking, car-buying advice, creative writing, and storytelling. I have many stories to tell.

Previous locations: Detroit and a 90-mile surrounding radius and short stints in Berlin and Brussels.

Relationship status: Married with two city kids, ages 16 and 9.

Partner’s age and profession: 64-year-old artist, Lee Quinones

My income: It varies!

Expenses in a nutshell: Ask me after my kids are grown.

Primary personal debts: The ancestors and the people who have helped me get where I am.

Work remotely or onsite? I’ve always had a home office.

A typical weekday schedule in a nutshell:

• 6 am-ish: Wake up to get kids out the door by 7. I try to soak a bit of sunlight and take a brisk walk before I hover over my screen.

• 8 am: Because I use a range of skills in my work, I build my schedule in chunks to be the most effective. I have days where I block out writing time for deep concentration and other chunks that I set aside for meetings or strategic planning for events and collaborations.

• Noonish: I take a mid-day break for a walk that usually involves a phone call, and then back to my desk.

• 4 pm: My daughter gets home from school. I spend an hour with her, prep dinner, often go see one of my son’s baseball or basketball games, which gets me some seat time in cars that I need to test-drive.

• 8 pm: The kids are older now, so bedtime is way more chill for them and for me in this life stage. I might work for another hour or two or watch a little bit of a show if I am too tired, and then unwind by reading a hardcover book before bed.

At least one day during the week, I carve out time to go into Manhattan, where most of the action goes down that makes NYC life so stimulating.

Ideal schedule: I’m good and crushing it when everyone is healthy, where they need to be, and there’s no crises that throws me off my game. This week we’ve had one family member down with the flu and another with an injury, so my game is a little wobbly.

How much my career is tied to my identity: I’ve been calling myself a writer since I was like 9.

My happiness meter: I am pretty happy. These days, I work to maintain focus, study the lessons of history, and stay true to my course to find peace and a way forward.

My career trajectory: Well, it’s not linear, but my goals have stayed consistent: to write, to make an impact, and to learn new things. Here’s the long version you won’t see on LinkedIn:

In college, I worked with Amy, founder of The Midst, on our school newspaper The State News and her Venus, a wonderful music zine constructed from a feminist lens. As a ’90s club kid I went to see bands or DJs almost every night in Detroit and around Lansing. What fun! During those years, I started writing a book about my grandfather, an Auschwitz survivor, after completing a thesis in college. It was heavy stuff and the dichotomy between my nighttime adventures and mission-based daytime work was a good balance that’s taught me a lot about how my brain works.

After college, I moved from East Lansing to downtown Detroit to be closer to my grandfather, who lived in a retirement community in the suburbs. I conducted hours of interviews and supported myself by working for Detroit techno labels, planning tours, and album releases. I wrote articles about Detroit music for international magazines. After a while I ran into some barriers — I couldn’t find a publisher for the book and I didn’t have enough money to finish the film, so I swerved in another direction. I spent a summer working in the Daimler-Chrysler newsroom cutting clips and then applied to law school. I went to law school for two-half years and made some real mistakes in my personal life (bad relationship) and needed a fresh start.

In 2003, I quit law school, and started writing for The Detroit Free Press and ran after-school art programs in Detroit Public Schools. I was learning how to cobble together a freelance life and to embrace “writer” in my career. I found an internship at AutoWeek, a weekly car magazine, and learned how to test-drive cars. In my spare time, I wrote about music, art, and on many random topics, like inner-city Detroit baseball and women’s health clinics for magazines.

That summer, I attended a writing seminar in upstate New York, where I met a mentor who invited me to house sit for her in Brooklyn. I moved to New York for a month, and basically never left. This mentor suggested I keep writing about cars, so I did, along with every other topic I could find.

Example: I wrote about mutual funds, and anyone who knows me knows that I am not a mutual-fund expert. I wrote about surfing, though I’ve never surfed. I’m from the old-school of print journalism, trained that an industrious reporter can write about anything through careful research, thoughtful questions, and chutzpah. Over that decade I wrote for over 100 magazines and edited an art and design publication. I started a blog called GoTryke with one of my friends from the Detroit techno scene, mixing my interest in cars, culture, art, and design.

Yet I was feeling burned out by the constant grind of internet journalist and declining pay, and longed to get back to creative writing. I entered an MFA creative writing master’s program at the New School at night after work, when my toddler was sleeping. At that time, I made my life goal come true – my first New York Times byline and became a regular contributor, which gave me a huge boost as a working writer.

I wrote for a lot of the legacy car mags like Car and Driver and Automobile. I wrote about celebs for a couple of the airline magazines. I had a music column in a defunct men’s magazine. After the Times car section folded, I questioned the future of journalism (again) and considered a career change, only to be recruited by The Verge in 2015 to report on transportation and tech. Later I became the Transportation Editor. Cue my expertise on EVS, autonomous cars, and the company that everyone asks about in this space.

By 2018, after so many years in journalism, I was looking for a new challenge. I realized that my friends, predominantly women in their 20s, 30s, and 40s, didn’t read much of my work on cars. I was their go-to person for car recommendations. I wrote articles that helped me understand the inequity in the auto industry on a deeper level — women buy more new cars than men, make all the decisions, and yet are largely left out of the education process.

I quit my job at Vox, and prepared to launch Le Car with my mother, who had recently retired from a public health career. We got into Techstars, a tech accelerator and launched the Le Car app in 2019. I also co-hosted a weekly gig at Cheddar that broadcast from the New York Stock Exchange during this time.

At Le Car, we’ve had a ton of mentors, some who have come and gone, and some who’ve stuck with us. We were teed up to raise money and chase the hockey stick curve that startup culture peddles after Techstars. I swerved again and realized that’s not what I wanted. So, in 2020, we launched the LeCar.co website, started producing events, and slowly building a community of solid women and some men who come to our events and seek our car-buying advice. Le Car provides advice, education, and connect all the ways cars impact our lives from design, to travel, to style, and safety. My mom and I work with fantastic teams and contractors, and we collaborate with artists, designers, and engineers.

I’ve also learned to embrace my multi-hyphenate approach to living. Over the last couple years I hosted a Vox media podcast about Tesla and edited an artist monograph. In the summer of 2023, I decided to pick up the book on my grandfather again, a full-circle moment, and I am working on that now. I’ve got a Detroit ’90s music scene novel going, too. I’ve found the balance I had when I was 22, managing people and multiple projects, along with the chaos of all of my grown-up responsibilities. Who knows what’s next? I’m sure I’ll keep learning.

My superpower: Curiosity and a cool head.

Menopause journey: Fully in it. At 40, I was told my estrogen was dropping. Six weeks later I was pregnant …

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S. Lucia Kanter St. Amour, 53, San Francisco

I know. My name sounds like an Italian opera, right? I’m frequently asked about it — it’s about a 7.5-minute story. Then people will say, “Well, can you just give me the 90-second version?” And I say, “No. If you really want to know the story of my name, take 7.5 minutes out of your overly busy life (which includes scrolling social media a lot longer than that — not judging!), and listen to the story here.”

Let’s connect on Linkedin • pactumfactum.com • Goodreads

Read my new Substack: Two Minute Taboo

Previous locations: Born and raised in a small town outside Chicago, then UC Berkeley for college (can you say “culture shock”? And I never went back to that small town).

I’m in the midst of: Oooooh, I’m so glad you asked — and I already spoiled it above but still — Drum roll please . . .

I launched my free Erotica Substack (separate from my professional podcast on Substack) on Valentine’s Day! Yes, yes, I realize erotica is the hot trend now with 50+ aged women, in which case you might argue I’m late to the party. However — not to put too fine a point on it — a lot of it is mediocre. This is not.

I’m writing under a pen name for practical reasons to set it apart from my professional brand, but let’s be clear: I will stand up right beside my erotica work and proclivities as the very apotheosis of feminine (and feminist) power — which I proclaim as a respected feminist essayist and VP emerita for UN Women). Gen X women like me, in particular, were sold a bill of goods about sexuality and it’s not too late for us to reclaim it (there’s a reason that a mainstream movie starring Nicole Kidman called “Babygirl” released in December, my fellow Grown Ass Ladies).

🌶 I use a 1–3 chili pepper rating scale for my pieces; they are short and sizzling, meant to be consumed in about 2 minutes, intended to enhance (not imbalance) your life.

But wait, there’s more. I’m releasing my fifth book, The Covert Buccaneer (complex dual timeline women’s book club historical fiction set in San Francisco — release date set for October 13, 2025), and already I’ve signed with a production company for a star-studded ensemble cast for the audiobook edition.

Oh, and I’m working as an attorney and law professor, too. You know. In my spare time.

Relationship status: Married to a man who manages (mostly) to keep up with my crazy.

Partner’s age and profession (if you have one): He’s Sicilian, age 58, and a retired designer, builder, and champion racer of Formula 1–style open-road racing cars. I know. 🔥, right? He can build or fix anything mechanical, digital, electoral, hydraulic, or automotive; and has never once left the toilet seat up. Oh. And he cooks. I’m basically a trophy wife 🏆😜

My income: Let’s just say I have something many Silicon Valley tech bajillionaires down the road from me don’t seem to have: enough.

Expenses in a nutshell: Well, I’ve moved my youngest son, a sophomore at UC Berkeley majoring in astrophysics (super fun as a mom to say my son is a rocket scientist!) into his first apartment, but technically he’s still on the payroll. His older brother with special needs will always need care: a group home, conservatorship, fiduciary services, etc. So, I’m always thinking about making sure he is provided for even after this world somehow has to limp along on its axis without me. I shop consignment; I don’t buy alcohol and makeup; I don’t eat out often, in favor of sumptuous home cooking (I consider leftovers to be food of the Gods); I don’t take expensive vacations (I went nine years without a vacation because of my special needs son. The savings add up!)

Retirement savings as of December 2024: I started contributing to my retirement with my very first job and didn’t stop. So, I’m in decent shape. I also never carried a balance on a credit card since my first one when I was a sophomore in college. If I couldn’t afford something, I didn’t buy it (with the exception of homes, cars, education debt — all paid off). You know who taught me money management? MY MOM!

Work remotely or onsite? Both. I’m wiggly. I need variety. I write at home. I teach onsite at the law school. I do speaking engagements in person (sometimes remotely); and my Chief Legal Officer role is remote for a company based in New York.

A typical weekday schedule in a nutshell: Look, I’ll level with you. I’m like an intelligent dog: if I get bored, I’ll just get into trouble. Not so much digging up the garden, but buying more shoes (and I don’t need more shoes). See “I need variety” above, plus I like my body to be in motion:

• I teach part-time at UC Law San Francisco (faculty for 20+ years, teaching Negotiation)

• Serve as Chief Legal Officer for a women’s healthy equity company

• Write 2–4 hours per day

• Climb the steps to Coit Tower to see new things in the rotunda murals (because those muralists from the 1930s are speaking to us!)

• Hike with my dog and say hi in my “woojy woojy” voice to every other dog along the way

• Cook really legit Italian food

• Read an average of 2 really decent fiction books per week (mostly women’s historical)

• Attend myriad SF arts, cultural events, and talks (Chris Hayes was just here and I went to see him and had a chance to talk to him. I even gave him some advice!)

• But! I start each day with my slow pour-over coffee, music, and writing. And no one is allowed to talk to me, lest they suffer the consequences of an irate Italian woman (Trust me. Just. Don’t. No one wins.)

Ideal schedule: Well, dang. I think I just described it above. GO ME! I’m killing it!! 💪

How much my career is tied to my identity: 50%

My happiness meter: I’m 95% human Labrador*. A happy tail-wagger. This annoys some people. Oh well. 🤷🏻‍♀️ That’s a “them” problem.

*Begs the question: what breed is the other 5%? Try talking to me during my morning pour-over and find out . . .

My career trajectory: I’m fortunate to be at a point where I can pick and choose my projects. I don’t have to work with or for any more meanies 😡. If I don’t like it or it doesn’t seem meaningful for creating a greater good, I’ll pass. Because I am often asked to speak at conferences (fave format: fireside chat) and I enjoy that, I can be picky about the ones that connect with my purpose and overall vibe.

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This senior marketing and content strategist specializes in RFPs, women's lifestyle content, and career coaching

Elizabeth Rago, 48

St. Charles, Illinois

Let’s connect: Linkedin • Instagram • Facebook

File under: Entrepreneurship, grant writer, teens, mental health, recovering people-pleaser

How I earn a living: By day, I work full time as a grant and RFP writer in the out-of-school time space. By night, I’m building a lifestyle brand and safe space for the whole woman called The Modern Domestic Woman.

Previous locations: Milwaukee, Wisconsin, and Oak Park and North Aurora, Illinois

Relationship status: Married 23 years to a man who supports all of my whacked-out business ideas. We have three kiddos together who are 18, 16, and 13 — a lot of hormones in this house.

Partner’s age and profession: He’s 50 and likes to kick, stretch, and kick #iykyk. We recently swapped roles so he could take a sabbatical to discover a new career path.

Income: Just enough to pay the bills

Expenses in a nutshell: Trying to feed three teenagers, I feel like most of our income goes toward food. It would seem that we could get by easily with my pay, but we are still recovering from our financial past. When the kids were little, both my husband and I were in car accidents, which turned into epic amounts of medical bills that broke us.

We also have a child with special needs, who requires a variety of mental health, OT, medications, and medical expenses — which is 100% worth the investment in our child. But it’s also a major challenge.

BUT, we have a roof over our heads, are able to pay our bills and buy food, so we are very thankful.

Primary personal debts: Mortgage, one car loan, my school loan

Retirement savings as of December 2024: Ugh, I hate this question, but I’ll be transparent. We just started rebuilding our retirement. The complicated life events I mentioned caused my husband and me to use our retirement to recover from a myriad of medical bills and lack of pay due to job loss.

It plagues me at the moment and I have a loop of shame going through my mind every time I think of money. I am working on that with my therapist.

Work remotely or onsite? For my day job, I work remote. Side convo: as a freelance writer, I was working remote before working remote was cool. I started freelancing almost 20 years ago and that helped us avoid childcare expenses because I could work from home and be with the kids.

With The Modern Domestic Woman, I work both remotely and in person for outreach and events.

A typical weekday schedule in a nutshell:

• I start my day listening to a 15-minute “devotional” podcast while I make my tea. I believe in a higher power and need all the help I can get to act right during the day. ;) Then I write in my daily mental health tracker.

• Work on MDW and any freelance clients from 5–7 a.m.

• My husband and I tag team school dropoff, so sometimes I do mornings.

• Work from 8 a.m.–5:30-ish for Right At School, my day job. We’re deep into our busy season right now, so that 5:30 turns into 6 a lot.

• Once I get off work, the husband and I catch up, and we complain about who’s going to make dinner. Then we tag-team dinner, too, while watching a movie that has a good soundtrack like Lord of the Rings.

• 6–8 p.m. Hanging with the kids, laundry, tidying up, helping with homework

• The husband and I like to watch some kind of show at night. At the moment it’s a carousel of true crime docs, Severance, the Dune series, Silo, and American Primevil.

• 9:30–10:30ish Check my MDW social and email to see if anyone left messages for support services and message them back.

• Go through my daily mental health tracker.

• But my work week doesn’t stop there! My weekends is where I build out my content for MDW and do any freelance work. I don’t mind working on the weekends but long for the day when I can truly take weekends “off”.
  

  

Ideal schedule: I honestly have no idea and I’m almost laughing as I consider this question. I’ve been building MDW for 12 years, so I have always worked two jobs side-by-side. Maybe just a 40–50-hour-a-week schedule?

I don’t mind working at all as long as my work reflects my values and fills my cup (and my bank account, let’s be real). My dream is for MDW to be able to support my family and focus on building that empire.

How much my career is tied to my identity: 50%

My happiness meter: I lean to the happy side of the spectrum, but only if I get enough sleep. I’ve learned that getting enough rest is crucial for my well-being. I would say an 8/10 because I’ve been through a good chunk of stress with my family over the years. The combination of knowing what’s important and 20 years of therapy helps boost my happy meter on a daily basis.

My career trajectory: I LOVE coming up with new ideas, so over the years I’ve tried to launch a few businesses. Most failed but one stuck and that’s The Modern Domestic Woman. BUT, because we’ve always needed insurance and a predictable paycheck to pay for the expenses of life like all those medical bills and therapies for my kiddo with special needs, it’s simply been about survival when it comes to my career trajectory. Just now, at 48, I feel like I have a little more control over my career trajectory and I’m excited to see it bloom!

My superpower: I have resting nice face and an innate ability to make people feel at ease, connect with them, and get them to tell me their stories.

I also have never-ending ideas when it comes to content.

Available for: Hugs. LOL, at this time, my schedule is packed and I am building the MDW empire, so I have no bandwidth for any more freelance clients. I am, however, available as a content and career consultant for virtual coffee.

I have virtual “Tea Time” multiple times a week with women who are looking for a sounding board, considering changing careers, need support services, and don’t know where to start.

I’d like to connect with: Female investors and women who have experience running a non-for-profit. There are two sides to MDW. A lifestyle media company and the support services side. I already have an LLC for the media company, but I’m applying to be a non-profit for the women’s health and mental health support services entity. As a grant and RFP writer, I know there is so much money available on a local, state, and federal level. Being awarded these grant monies, I will be able to help women pay for crucial services like therapy, and medical and legal expenses.

Menopause journey:

It makes my face hot to think about this conversation. I’ve spent the last 3 years researching my various symptoms, educating myself about perimenopause, and discovering valuable resources like The Midst to help me feel less alone.

Healthy habits:

• Keeping a daily mental health tracker has been a game changer. It’s the way I purposefully check in with myself in the morning before the chaos starts and the evening, when I can quiet my thoughts and reflect.

• I switched from coffee to tea about three years ago and it’s been wonderful for my gut health.

• Remember when I said I work remotely? That means HOURS in front of a computer. I have a walking pad that I’ve been using for four months and now I walk about 5–6 miles a day, five days a week! Plus, I’m down a full pant size and my sleep is so much better.

• My digestive system has been a challenge for me for years. After going through colonoscopies and getting the diagnosis of “everything’s fine” one too many times, I took my diet into my own hands last year. For the most part, I only eat fruits, nuts, vegetables, and some lean meats. No dairy (crying) or processed foods, unless it’s a special occasion, and then I have to go straight back to my diet. This is difficult but the more I practice this way of eating and get creative with it, the better I feel.

• Tapping into my higher power is definitely a healthy habit. I know people feel uncomfortable talking about this topic, but I think it’s OK to be transparent. My higher power embodies love and compassion — full stop. And taking time to reflect on my values and the intention behind what I do on a daily basis connects me to a being greater than me and keeps me grounded in what matters most. My family, helping others, and making a positive impact on my little corner of the world.

• I’ve recently embraced a sober-curious mindset and I am 12 days in. I feel absolutely fabulous in my body and mind so I’m going to keep this habit up.

Bad habits:

• COVID really presented the idea that having cocktails during the week was a good choice and I fell right into that way of thinking. I hated feeling sluggish and gross the next day after a glass or two, so I recently cut this habit and know it’s a good choice for me.

• Mulling over conversations in my mind hours (and sometimes days) after they’ve happened.

• Overcommitting. Where are all my people pleasers at? I LOVE helping and sometimes love helping beyond my own physical capacity. I needed to establish boundaries and redefine my values over the last six months to help me from over-committing and burning out.

Career timeline in a nutshell

2001–2003: Customer Service and Sales Rep, Sanford Corporation

Straight out of college, I applied for any and every job I could — and took the first offer I got because I had bills to pay and I didn’t have the luxury of waiting. I started working for the Sanford Corporation (think Sharpie markers and Papermate felt-tips pens) and worked in customer service in the call center. Shortly after, I transitioned to inside sales.

Takeaway: Sanford was going through a rebrand as they had been acquired by Newell-Rubbermaid, and I was assigned to collaborate with our e-commerce department to create internal/external product information tools during rebranding. I was fortunate that both of my bosses saw my writing as an asset and assigned me projects like editing, creating product copy, and a variety of customer communications.

Why I left: I wanted a career where I was making a difference in someone’s life instead of “just selling pens.”

2003–2006: Admissions Counselor at Aurora University

I loved being an undergraduate admissions counselor at Aurora University. In this role, I was responsible for recruiting full-time undergrad students, which involved a lot of one-on-one counseling, application reviews, interviews, and campus tours. I also walked students and parents through the financial aid process.

On the marketing side, I collaborated with the communications team to create materials for the university and made sure the website was error-free and consistent with the brand.

I interacted with diverse groups, from students to alumni to faculty, and enjoyed representing the university in a positive way. Another part of the role was working with student ambassadors, training them, and helping foster relationships between them, faculty, and staff.

Takeaway: I was really good at this job and could have made this my career if not for the fact that I was emotionally immature at the time. It’s embarrassing to admit, but I was not a nice person to some of my co-workers. In fact, I was a workplace bully. I hate that I was mean to others as this is the polar opposite of how I live my life today.

Why I left: My husband and I relocated to Milwaukee, Wisconsin, for his career.

Late 2006-early 2007: Six-month career gap

We moved to Wisconsin and had just given birth to my son. After writing in my last two positions, I felt confident that I had solid writing samples to start freelancing. I started writing press releases for a Federal Bank and reaching out to small businesses asking them if they needed help writing web copy or creating their newsletters.

2006–present: Freelance writer and content strategist (the timeline from here on out will be a rollercoaster because freelance)

To say I was driven to be a writer and make a living is an understatement. My dream was to write for a women’s lifestyle magazine, so I started pitching to all my faves — and received no responses. …

I shifted to building more of a lifestyle resume and got my first client, a yoga studio and soon after, a vegan restaurant. I created marketing material and copy for a variety of projects, and I loved it.

Nineteen years later, I’m still freelancing and helping people with their content strategies.

Other freelance highlights:

• I’m proud to say that over the last 19 years, I’ve freelanced for small businesses, ad agencies, newspapers, and large corporations, providing health, wellness, and women’s lifestyle content. I was also a syndicated columnist but was laid off due to Covid.

• I worked several part-time jobs to supplement my income when my freelance work dipped including working the front counter at Two Wild Seeds Bakery in St. Charles.

• In 2013 I was in the cast of “Listen to Your Mother,” where I read a piece called “Under the Big Top” at the Athenaeum Theater in Chicago and was part of the Illinois Farm Families “Field Moms” reporting on agriculture in Illinois.

• Freelancing has led me to meet so many amazing people and writers like Amy Guth, above. Amy is an amazing film producer, screenwriter, journalist, and speaker. …

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This career-long solopreneur started as a musician and has built a career as a singing teacher, public speaking coach, and executive coach

Alicia Dara, 51

Seattle, Washington

Let’s connect: Linkedin • Instagram • Substack

File under: Executive coaching, professional development, women in leadership, C Suite women, coaching, women’s media

I’m in the midst of: Growing my executive coaching business, which takes me all over the U.S. to work with high-level individuals and corporate teams. I’m also growing the staff of Womancake Magazine, my platform for women over 40 that I started in 2022.

Beyond that, I’m working on expanding skills like cooking, working out, and investing. I was stuck in a scarcity mindset for a long time, and have only recently begun to break free. Gotta say, it’s pretty great!

Previous locations: Born and raised in Vancouver, B.C., educated in New York City.

Relationship status: Been with my Hubz for 12 happy years. We are childfree and very connected to our community.

Partner’s age and profession: 52, CTO

My income: I don't talk about my finances in public forums. But I do have financial and business tips for freelancers and solopreneurs:

1. Think big about your money, even during the leanest times

That means saving and investing tiny amounts now, so that you have good financial habits in place that you can scale as time goes on, and you generate more income. Don’t be afraid of investing! I waited too long on this; I should have jumped in much sooner. Before I worked with my financial planner, I used Ellevest for a few years, and it taught me a lot.

2. Stop messing around with social media and start investing in actual relationships

Your goal is to create a robust client pipeline that comes directly from past client referrals, and that will only happen if people know you, like you, and trust you to help them get where they want to go. You can work at a discounted rate in the beginning, just to build up your client list.

3. Don’t under-promise and over-deliver

This is a common mistake that many freelancers make at the beginning of their careers and stay stuck in for too long. Don’t do this!

Under-promising and over-delivering is the quickest way to burn out. Clients will treat you as if they own all of your time, and you’ll be running to catch up forever. Make the value of your work clear and price it accordingly, and deliver at that level. Your power comes from this simple balance. If clients want more of your time, charge them for it!

4. Create a Friday Power Hour

I learned this from my high-level clients. As you go through the week, whenever you come across an article, podcast, or other media that interests you and sparks your curiosity, put it in a dedicated folder. Look for articles about what’s happening in other sectors and industries: how are leaders solving problems, and what kinds of trend-spotting are they doing?

Once a week on Friday afternoons, listen to and read everything. Spending time in this mindset will break you out of your usual ways of thinking, and that can lead to much more effective solution-making in your own work.

Work remotely or onsite? Both. I work with private clients remotely from my home office in Seattle, and I also fly around the country working onsite with high-level individuals and corporate teams. I like this combination of flight and return; it makes each week feel new and fresh.

A typical weekday schedule in a nutshell: If I’m at home, I’ll work Monday–Friday from 8 am to 5 pm (with an occasional weekend travel day if that’s how my schedule works out).

If I'm traveling, then all bets are off, and I’m on a client’s schedule and timeline. Most clients will fly me in the night before I give a big training, so I have time to catch my breath and prepare. The next day I bring my carry-on to the venue and fly home right afterward. Sometimes I have to fly to another city for another client. My schedule is like a game of Tetris, with all these different bookings coming at me, and I just have to stay calm and arrange it all in a way that allows me to keep my sanity while working at my highest level.

Ideal schedule: Mostly I’m fine with my current schedule, although I’d love to be able to wrangle it so that I could do no more than two trips per quarter. Sometimes my travel is all crammed into a few months, and it’s a lot! Once I’ve worked with a big corporate client and they want to book me again, I will often ask if we can schedule the next training a few months in advance. That keeps things manageable.

How much my career is tied to my identity: 50%. I learned a long time ago not to over-identify with a career. People are a lot stronger if we stay fluid and flowing rather than stuck in a single groove.

My work also involves engaging multiple skill sets, and I try to keep adding to them as I go. For example, last year I learned a ton about neuroplasticity, so I can better help my clients employ a growth mindset to everything they do. This year I’m learning about systems theory, so I can better understand the way they see the world and their own high-level work.

My happiness meter: On a daily basis? 8/10. It would be closer to 9.5/10 except for ongoing perimenopausal issues that make my physical pain threshold higher than it should be. Looking forward to crossing over to the other side of all that!

Career timeline in a condensed nutshell

1996: Started teaching singing lessons privately at arts organizations

Takeaway: People will always come back if you elevate their mood and expand their sense of possibility.

Why I left: I earned enough money to cover my bills but not much more than that.

2011: Started adding public speaking to my coaching business

Takeaway: I quickly realized I could make much more money, and I identified a key demographic that needed a ton of help: professional women. I started giving big and small group trainings that began to attract a ton of attention.

Why I left: I wasn’t feeling challenged by the kind of clients I was working with.

2021: I pivoted to executive coaching

Takeaway: Working with high-level, high-performing individuals and groups is constantly inspiring. I’ve gotten an education in all kinds of sectors, and I’ve been able to help tons of professional women from around the world find their Power Voice. They often keep in touch with me after we’ve worked together, and I love hearing about their ongoing accomplishments and success, it’s the best part of my job!

My career trajectory: “Lifetime” solopreneur

I’ve been largely self-employed my whole career, and I’m used to the slings and arrows that go with it. I was born to a family of professional musicians, and I trained as a singer from an early age. After high school I studied musical theater at a conservatory in New York City.

I was extremely shy socially, but I was told (in quintessential ’90s language) that my stage confidence was “fierce”. None of this made me love musical theater. I didn’t want to sing songs about being a woman that were largely written by men. In my last year of school, I started playing guitar and writing my own songs and immediately felt better.

I moved to Seattle in the mid-’90s and worked hard in the music scene (which I wrote about here). I had a boyfriend who was a guitar player in a band, but he also wanted to sing, so I gave him voice lessons. His voice got much better and many people noticed, and they asked me to teach them. That was the first phase of my career.

During that time I taught teenagers and adults, both privately and for various arts orgs. I worked with all kinds of local musicians including some rock stars and industry types. I also made a ton of records of my own music, and toured around the country whenever I could afford it. This was during the Lilith Fair era, when venues would pay good money for women to perform their original songs. I also played and sang back-up in other bands, and did some voice work in commercials and soundtracks. I eventually formed my band Diamondwolf, and we won some awards, which felt great.

About 15 years ago people started asking if I would coach their speeches for weddings, Bar Mitzvahs, and work presentations. I noticed that professional women often struggled with the confidence they needed to just be in the room, let alone speak up for their work. I created a training called “Public Speaking Bootcamp for Women” and taught it to groups in downtown Seattle. Word spread quickly and every training was full. I had no idea how much it was needed! I decided to get an actual coaching certification, which made me more attractive to corporate clients. One of my old friends from the Seattle music scene reached out to me from Microsoft, where she was employed, and asked me to give my bootcamp training to the women on her team.

From there, my coaching career took off. I coached huge groups on the Microsoft campus, and private clients in my home office. This was also a time when I was volunteering for my local Planned Parenthood office almost weekly. I put together a CD compilation of local artists to benefit PP, and it was endorsed by Cecile Richards herself. Learning from the largely female staff at PP was an honor. It strengthened my belief in the power of compassionate, science-based public health policies that can uplift the health of entire populations, and it showed me the power of community support.

My reputation became better-known, and in 2016 I coached a prominent political candidate in their campaign office (in case you're wondering, that environment was almost exactly like the chaos you’ve seen on “VEEP”). This led to more high-level performance coaching for other public figures.

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We’re kicking things off with this new pilot series: What Linkedin Doesn’t Say, in which women 35+ share honest depictions of their professional lives. The goal is to look back on our careers to date, identify patterns, and get to the heart of what we really want — revolution GAL-style now.

So without further ado, here’s an interview I did with myself. Do I have it all figured out? Oh, hell no. That’s why I’m being transparent with you — maybe by writing this, you’ll help me figure out my future. :) — Amy

Age: 48

File under: Double day; entrepreneurial tendencies; tech; women’s health

I’m in the midst of: Working full time as a content strategist in tech while bootstrapping The Midst, this here independent platform empowering women 35+ to live healthy, inspired lives on their terms. I lead a team of five remote folks plus freelancers.

Location: Phoenix, Arizona, for two years

Previous locations: Chicago suburbs; Brooklyn; Chicago; Bay Area

Relationship status: Happily married for 12 years with twin 9-year-olds, one with very special special needs

Partner’s age and profession: 51, psychotherapist, owner of Therapy for Creativity

My income: North of $150K per year

Expenses in a nutshell: We live pretty lean for a family of four. I shop for deals and keep a close watch on our expenses. More than half of my day-job income covers bills for The Midst. I do not pay myself for my work at The Midst, but hopefully that will change as we grow! In the meantime, I’m proud to say that The Midst has no debt and I own the company 100%.

Primary personal debts: Mortgage, loans on two cars

Retirement savings as of December 2024: $190K in 401K

How much my career is tied to my identity: ~80%

My happiness meter: Depends on the day, but my average is about 7.5 out of 10.

Work remotely or onsite? Thank goodness for remote work. I’ve worked remotely for nine years and am always eager to travel for offsites or to company headquarters. A full-time onsite job would be difficult — mainly because my day jobs tend to be for tech companies that are based in San Francisco or New York, which are expensive cities. My husband and I tried relocating with our kids to these cities, but it’s very hard to line up everything for everyone: close proximity to the office, solid public schools for my regular-ed daughter, and a special school for kids with severe special needs for my other daughter.

A typical weekday schedule in a nutshell

• Drive daughter to school

• Usually work between 7 am–5:30 pm Monday through Friday, primarily at my day job and secondarily on The Midst

• Pick up daughter from school in the afternoon

• Dinnertime with the fam

• Evening walk with my dog, Luna

• Reading before bed

Ideal schedule: Ideally, I’d work about 20 hours per week, and I’d set my own hours. I don’t want to stop working completely (I’d be bored AF); I just want less pressure to work a “double day.” Also, when I’m inspired and in flow, I naturally want to “work” as many hours as necessary.

My career trajectory: You can take the GAL out of entrepreneurship but you can’t take entrepreneurship out of the GAL. I’ve always teetered between running my own small business and full-time work. I started a scrappy fanzine called Venus in my college dorm room at age 19 with a budget of next to nothing and scaled it to an internationally distributed magazine before selling the company in 2006. But not for a lot of money. :)

After being my own boss from an early age, I was eager to work for others, at larger companies. In 2009, I moved from Chicago to New York and started over during the economic downturn — at a time when print journalism was going downhill. That was a challenging time, but ultimately a pivotal learning experience for me. I wrote a thing about it here.

Looking back, I have a pretty intense work ethic with a bit of a risktaker streak. I wanted to start working as soon as I could, so I started by babysitting at 11 and volunteering at a hospital at 13. As soon as I hit the legal age to work at 14, I got a job at an ice cream shop in Michigan, raking in $3.65 an hour. In high school, I started a business making jewelry and sold my handmade beaded necklaces at school and craft fairs.

My superpower: I specialize in creating high-performing content strategies for brands. I love the process of figuring out what makes an audience tick and the kinds of content that keep them coming back for more.

Available for: Content strategy consulting. View my portfolio here.

Menopause journey: I’ve been in perimenopause for about eight years. I still get my period, so I’m guessing I’ve got another year or two of peri to go.

Healthy habits:

• Primarily vegetarian diet

• I eat a lot of almonds and frozen berries, and drink a lot of water.

• In my mid-40s, I cut way back on drinking red wine and switched regular coffee to half-caff with Stevia.

• I get a lot of sleep thanks to the help of Trazodone (prescribed by perimenopause specialist at Northwestern University Center for Sexual Medicine and Menopause).

• I walk at least one mile per day and am lucky to live in one of the sunniest places in North America.

Bad habits: Processed foods, microwave popcorn

Career history in a nutshell

2006: Sold my magazine, Venus, at age 30

I continued to work as editor in chief for the new owners for about two years. I also worked in the evenings as a journalism instructor for Columbia College in Chicago.

Why I left: After a couple of pretty happy years, I had a falling out with the new owners of Venus. Oh, the drama.

Per the owners’ request, I gave them six months notice of my departure and recommended my replacement, an editor I’d hired about a year earlier. The owners decided to boot me out early, right as the economy was crashing. My attorney warned me this might happen.

Moral of the story? Don’t give your boss six months notice. :) It was painful at the time, but let’s just say that it propelled me forward into a new career path. And I learned a shit-ton as an early entrepreneur — especially what not to do.

2008: Freelancing for NYLON, Time Out Chicago, etc. + substitute teaching in NYC Public Schools

I moved from Chicago to New York to start over and search for a full-time job. To supplement freelancing, I tried my hand at substitute teaching. I thought I’d experiment with substitute teaching as a way to figure out whether I should get a master’s in education. I quickly learned I am not cut out to be a substitute teacher — I was peed on by a kindergartner and also had many paper airplanes thrown at my head in a Harlem high school bio class.

Key takeaway: Learn by doing.

2009–2011: Content and community for HarperCollins and Girl Scouts of the USA

After struggling to find a full-time job for months, I finally landed two jobs and decided to take both. I worked onsite at GSUSA, but only 35 hours per week. In the evenings and on my lunch break, I worked remotely for HarperCollins on an online startup project called inkpop.

Why I left: One bully coworker at HarperCollins (everyone else was great) and an emotionally troubled (though, extremely talented and brilliant) manager at Girl Scouts. I went to HR to ask for help and they eventually pressured me into resigning. Key takeaway? HR will probably not be on your side. The good part? Everyone else at Girl Scouts was pretty top-notch; I made great friends and keep in touch with them today.

2011–2013: Founded DIY Business Association and freelance copywriting for Levi’s and West Elm

Toward the end of my time at Girls Scouts, I got the entrepreneurial itch again and started DIY Business Association to empower solopreneurs. Our mission at DIY Business Association was to empower and connect solopreneurs. We organized a series of events and hosted inspiring speakers.

Freelancing as a copywriter was another great skill-building opportunity.

Why I left: Through the DIY Business Association, I partnered with Etsy and that connection turned into a full-time job. I was excited to work for such a cool and fast-growing startup.

2012–2013: First content manager for Etsy’s Seller Development team

The people and culture were absolutely fantastic and full of positive energy, and I loved writing for and about Etsy sellers. Plus, I could take my dog to work! Engineers developed a system that communicated “you’ve got poop!” if your dog went No. 2 in the office. Hands down, working for Etsy during its somewhat early days was one of my most impactful professional experiences.

Why I left: Cool boss turns mean, and low pay. I later learned that coworkers dealt with similar issues, and my manager was asked to leave. In retrospect, I wish I’d stayed at Etsy longer! My equity today would have been valuable. I was naive about the equity process, though, and screwed that up.

Then I was recruited by an agency for a better-paying opportunity, which was critical at the time because I was a newlywed and supporting my husband while he was in college.

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