Meet Jaime Derringer: DesignMilk founder, award-winning artist, and serial entrepreneur
"I’m in my third career act and am lucky to have invented jobs for myself as I go."
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
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.
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 used to be a workaholic, and it took me a few years to undo the behaviors that were literally making me sick and anxious.”
— Jaime Derringer
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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