How Jennifer Gresham Balances Many Jobs (Air Force Scientist, Coach, Writer, NGO Founder)

by | Jul 8, 2022

Meet Jennifer Gresham. She’s a multi-careerist based in California. We met on LinkedIn, when he responded to my “2 careers” article. We struck up a conversation, and I learned about her many hats. Check out her insights.

Jennifer’s careers:

  • Air Force scientist (biochemistry Ph.D.) – variety of jobs as an active duty officer, culminating with role as the Assistant Chief Scientist for the Human Performance Wing
  • Writer – wrote articles and book chapters on human performance augmentation
  • Coach – built my own business as a coach, an accidental career shift that happened when my blog readers wanted help changing careers as I had. Gradually expanded to include moonshot coaching–helping people define and take on impossible but deeply meaningful goals
  • Nonprofit founder/Executive Director – I now run Work for Humanity, a nonprofit where we are helping small business owners in the food & beverage, retail, and hospitality industry create better jobs, for their workers and themselves, resulting in a more equitable and enjoyable future of work for all.

On her motivations for many careers

I’m very motivated by challenge, so once I achieve a reasonable level of mastery in my work, I’m usually looking to pivot.

But I’m also just intensely curious about the world. I see each career as an educational adventure, where I get to teach myself and experiment with new ideas and approaches to problems.

On how long she has had these careers

My careers all overlapped with one another–and still do. For example, I’m no longer getting paid as a writer, but I still do an enormous amount of writing to advance my current career.

  • Air Force scientist – 20 years
  • Writer – 3 years
  • Coach – 11 years
  • Nonprofit founder/Executive Director – 4 years

Advice to aspiring multi-careerists

The biggest issue I saw for career changers is they undervalued their previous experience. They thought they were starting over, and thus, employers needed to “take a chance on them.” Show yourself and others how you can creatively apply your prior experience/expertise to a new problem. It makes you invaluable.

Overcoming obstacles

Money is always a big one.

I initially took a big pay cut with each pivot. I was fortunate that my husband was willing to support us financially when I made the jumps, at times pulling money out of savings if his income wasn’t enough to cover our expenses.

This was scary, and we both had to have faith in my ability to grow into higher income and impact. With time, my new career always paid us significantly more than my last, so I was able to “pay us” back, or fund the next adventure, depending on how you look at it (though my nonprofit pivot will likely prove the exception to that–time will tell!).

On how careers are mutually beneficial

Each career has made me more valuable to the next.

I simply apply the tools I’ve learned from one career (scientific method, data analysis, communication, coaching) in a new context. It also gives me an incredibly diverse professional network.

I’ve leveraged my science contacts, for example, to better understand systems and social change in my nonprofit work.

On finding balance

When I changed careers the first time, I took the time to define my personal values. One of those values is Family First, which means my relationships with my immediate family members (husband and daughter) take precedence over everything.

That being said, our rule as a family is that, if someone really wants something, if something is really important to them, the rest of us do everything we can to support them in pursuing it. It is both a creative constraint and a wonderful way to always stay grounded in what matters to me.

On something she wishes to have learned sooner

The most important professional skill you can learn is how to create opportunities for yourself.

Multi-careerism makes you more resilient and resourceful, so you never have to worry “What if this doesn’t work out?”

Suggested reading

  • David Epstein’s book Range is essential reading to help you understand why generalists are just as important as specialists.
  • Slowing Down to the Speed of Life by Richard Carlson will give you a better mindset for embracing uncertainty and avoiding busyness.

Overcoming the stigma of multiple careers

Yes, certainly. I notice I’ve never once been recruited for a job in corporate. That still surprises me, to be honest.

I imagine that my entrepreneurialism, in addition to multi-careerism, makes me a poor fit for most corporate jobs as they are defined now.

My strategy to overcome that has been to start my own ventures.


On how to sublimate ego at the day job

For the most part, I haven’t had to do this, but when I coached career changers, I would help them see that it’s just a mindset shift.

Instead of seeing the job that’s paying your bills as an obstacle, see it as the fuel for your pivot (which it is!). Plus, you can learn something relevant to your goals in almost any position. Get curious and creative.

On how to decide what to do next

The first time I changed careers, it was a process! I looked at the intersection between my skills, my interests, and my network.

After that, I saw gaps in the new fields that I was working in that I thought I could contribute to. If a problem persists in a field, it probably needs a new perspective, in other words, a generalist. I also use the intersection of fear and excitement as my navigation guide.

A Day in the Life

My schedule is highly variable–since I own it, I’m able to shape each day to the tasks at hand and my energy levels. Here’s one recent example.

7 AM – wake up

7 – 8 AM – Breakfast, Wordle, social media, plan out my day

8 – 11 AM I try to save this time for thinking/strategic planning and projects that require a lot of creativity. For example, that might include reading/watching videos about fundraising, then writing our fundraising strategy, then planning out the next several newsletter topics to match up with the strategy.

11 AM – Noon Lunch break, where I eat, check email/social media, take care of any small errands that need to get done

Noon – 3 PM Calls with my team, clients, potential partners, potential funders, usually by Zoom during the pandemic

3 – 5 PM Workout/shower/snack

5 – 6 PM Wrap up any projects that didn’t get done in the morning

6 – 7 PM Dinner as a family

7 – 10 PM Reading, watching movies/talking with my daughter

10 PM Bedtime

For the most part, I don’t work over the weekend unless I feel like it and my family is otherwise engaged with their own things.

Where to find Jennifer

  • LinkedIn
  • Work for Humanity
  • I’m always looking for speaking opportunities on the topics of the future of work, leadership, and unlocking human potential. I also still occasionally take coaching clients who inspire me, including career changers.


Kabir Sehgal is a Multi Grammy & Latin Grammy Award winner, as well as New York Times bestselling author.

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