OMG, The Midst community is on 🔥
Watch comics Casey Balsham & Carole Montgomery + bestselling author Mary Laura Philpott live from your couch on October 14! | Meet the career coach who will help you get your sh*t together
This community builder and career coach specializes in creating order out of chaos and getting sh*t done
Rebecca Callahan, 50
Lives in: Denver, Colorado
Owner, Summer Day
Certifications: ACC (Associate Certified Coach) and CPCC (Certified Professional Co-Active Coach)
I coach early-career women through the “broken rung” leadership transition and build communities that connect and retain customers. Whether you’re navigating a career pivot or creating a space where your customers keep coming back, I’m the strategic partner who stays until you get results.
My rate: varies depending on if the work is hourly or per-project, and whether the client is for-profit or non-profit
I’m in the midst of my glide path
I came up with this concept when my husband and I had dinner with longtime friends. We were discussing our next chapters and how we’re going to get there. I explained how my goal wasn’t retirement, it was re-career. That, of course, raised some eyebrows, so I explained it as if I was in a glider.
Instead of retiring from something (say, corporate America), I was looking to retire to something — slowly but surely making changes and re-prioritizing until I landed gently after a long, slow trip down.
My primary goal in this next chapter isn’t monetary, it’s impact. What can I do to help the next generation? What can I do to help purpose-driven organizations thrive? How can I be there for my almost-adult children and aging parents in a way that allows me to be fully not just physically present?
My focus on impact means I’m selective about the clients I take on. I want to help women avoid the mistakes I made, and build meaningful communities that are doing good in the world — not just maximize profits. Although revenue isn’t all evil!.
My priorities have shifted in the past five years for several reasons
First, when my daughter (now 17) was in middle school, she wrote an essay on the gender pay gap and was appalled. She couldn’t understand why women were paid less to do the same job a man did. I realized she was watching and I wanted to do something to make a difference.
Between 2020–2022, I lost three parents to stroke, Alzheimer’s, and cancer. And I’m now caring for my father, who also has dementia. Those years were rough. I was working full time in intense roles and while my companies provided me the grace and time to do the things I needed to do, it came at a cost. I was burned out, mentally, emotionally, physically, and spiritually. And, you know what? Watching my parents succumb to these horrible diseases, it became readily apparent to me that what I was doing didn’t matter. Not really.
And what did matter? Well, that’s what I set out to find out.
I started my glide path in 2024 and haven’t looked back since. It was the best decision I’ve ever made. Prioritizing myself, health, family, and purpose have been a game-changer — especially as I’m deep into perimenopause (that’s a whole other “midst of”!).
My new priorities have radically changed my family dynamic AND how my work days look. I start each morning with stretching, meditation, and journaling. I’m learning to quiet my mind and listen more deeply to my body and give it what it’s craving. Sometimes that’s an intense weight-lifting session, sometimes it’s a long walk. Sometimes — and I’m being real here — it’s sitting and staring at the wall until my monkey brain calms down.
Now, instead of “I have to”, I find myself saying “I get to”. It isn’t just positive thinking — it’s a fundamental shift in how you structure your life and work.
That’s the mindset I help my clients develop, too.That’s the kind of communities I want to build.
This shift in perspective directly influences how I work with clients now through Summer Day. I understand the weight of burnout, the importance of intentional career moves, and the value of creating space for what truly matters. When I help women navigate the ‘broken rung’ or build a community that brings people together, I’m drawing from this hard-earned wisdom about sustainable success.
So, yeah, instead of defining retirement as jumping off a cliff — one day you’re employed and the next you’re not — I’m defining it in my own way. Re-careering as I float down my glide path.
Career highlights
Helping a client 6 months out of a job land her dream role with a higher salary than she dreamed of asking for
Launching and growing thriving alumni communities
Building teams that choose to follow me
Turning around a failing subscription product
My super powers
I create order out of chaos and get shit done in the service of my clients and colleagues. I’m a relationship builder who sees both the big picture and all the moving pieces. I see people, understand problems (opportunities), and can intuit what’s working and where the gaps are.
I’ve done so much in my career: relationship management, strategic marketing, retention, subscription management, sales, sales ops, product & project management and process improvement. But the throughline of my entire career, regardless of what role I actually held, is supporting others. Whether it’s:
Making my client look great in front of their boss by running a successful marketing campaign
Removing obstacles for my team so they could do their jobs better
Streamlining processes to minimize friction
Launching communities to bring people together
Supporting a coaching client who’s figuring out where they want to go
Ideal customers and clients
Early/mid-career women who are usually in the midst of a transition themselves: new job, new promotion, new move and looking for clarity around the shift. (Also see HR departments looking to invest in their new managers.)
Organizations offering transformational workshops: Participants leave inspired but struggle to implement changes alone. You want to support their growth and keep them close. A community solves both — providing ongoing support for participants while deepening their connection to your organization.
Market research and insights organizations: Subscription-based businesses that understand recurring revenue.
Community-curious organizations: Wondering if community is right for you? Let’s figure it out together.
I’m open to trades
As my glide path focus is on impact vs. profit, I’m definitely open to conversations with the right organization/individual to partner in creative and mutually beneficial ways. Email me at rebecca@summerday-llc.com.
Have you read Women’s Survival Guide?
Created by Founding MidstHer Kim Druker Stockwell, Women’s Survival Guide helps you shift from NOW WHAT?! to an exciting WHAT’S NEXT? through personal stories, inspiring interviews, and practical advice.
Discover new passions and a renewed sense of possibility together.
You’re invited to Midlife Women’s Wellness Summit on November 13 in Oak Park, Illinois
This summit near Chicago is thoughtfully curated by Founding MidstHer Angie Maguire, RN BSN, NC-BC, featuring:
Meditation with Chelsea McGee, RN, BSN, NC-BC
Addressing genitourinary symptoms of menopause
“Mind the Change” with Dr. Louisa Olushoga, MD, psychiatrist
Breakout sessions on breath work, healing energy, vitality yoga, and more
Seeking writing submissions about eating disorders
“This Is Not Your Mother’s Eating Disorder” is an anthology organized by Founding MidstHer Amie Newman, who is seeking personal essays, poems, visual art expression, and cultural critiques by midlife and older women who have experienced an eating disorder in adulthood.
1,000–3,000 words for personal essays and interviews; 100–200 words for poems. Learn more and submit here.
Community classifieds are a perk of being a Founding MidstHer.
In case you missed it: Read the September 2025 community classifieds here.
Organized by Founding MidstHer and award-winning essayist Kerri Devine
Use code LIVE to get a discount
As proud sponsors, we invite you to join The Midst at Pass the Mic for Perimenopause on October 14 at 7pm EST (4pm PT) in Charleston, South Carolina, and everywhere via livestream.
From the people who brought you Midlife Monologues (the sold-out, critically acclaimed show about the arc of a woman’s life), Pass The Mic will feature an electric cast of comics, memoirists, poets, actors, and singers expressing the hopes and challenges of their journey “in the midst.”
Featuring
Comics Casey Balsham & Carole Montgomery
Bestselling author Mary Laura Philpott
Dr. Kate & Jay White of Heads & Tails Podcast (a psychologist and an OB/GYN who’ve been married for 26 years)
Laugh, cry, join the sisterhood, and feel seen and supported in your life’s journey. Just for Midst readers, get a ticket discount when you use this code: LIVE.
I just booked my first session with Rebecca Callahan … my first time meeting with a career coach. I’m really curious how it works.