1+1: How to find your next career move + What to Make of a Life
- Josh Wymore

- May 13
- 3 min read
Here's one leadership idea and one resource I’ve found beneficial in the past two weeks:
1 idea: How to find your next career move
Whether you are a recent grad, a soon-to-be-retiree, or just someone who is pondering your path mid-career, I have two pieces of advice for you: keep a notebook, and make two lists.
Keep a notebook. When we approach these fork-in-the-road moments, we often fear that we'll have no options. The reality is often the reverse, however. Instead of starving for a lack of good options, we drown in a sea of opportunities. We ask:
Which of these jobs should I take?
Which of these schools should I attend?
Of all the places I could move, where should I live?
Thanks to globalization and our ever-evolving economy, we have more options now than at any other point in history—and the weight of all those choices can be overwhelming.
The biggest challenge in navigating these near-infinite options is knowing which opportunities are right for you. That's why self-knowledge is such a superpower for leaders (and why it’s the first pillar of Humbler Leadership). But if you need more of it, how do you get it?
Start by taking a page from your science classes and treat yourself like an experiment. As you work (or date, or visit schools), observe what you like and don't. Notice what brings energy and what drains it. You might think, I really enjoyed organizing all our information for that team project. Maybe I should look into a project management career? Capture these observations on paper and start to form hypotheses you can test.
When I was in college, I followed this process and learned that I liked coaching people more than I liked coaching sports. I had always enjoyed athletics, so becoming a football coach was my dream job. But once I started doing the work, I noticed that I gained the most energy from the personal connections with players outside of practice. Winning championships was fun, but helping them discover their gifting was 10x better. That observation ultimately led me away from athletics and toward leadership development.
Make two lists. As you refine your observations, take the next step and make two lists for any opportunity: your non-negotiables, and your dreams.
What are your non-negotiables in a house? And what would be ideal?
What are your non-negotiables in a university? And what would be on your dream list?
What can you not live without in a job? And what are the cherries on top?
For my first job out of grad school, one non-negotiable was the opportunity to take on new challenges that would help me grow professionally. I knew I didn’t want a job where I could coast; I really wanted to be pushed.
I also had dreams—things that would be ideal but not deal-breakers. Teaching in the classroom was one of those dreams.
When I sized up my job prospects, I had three available options. In the first two, I felt I’d excel on Day 1, while the third seemed so challenging that I feared I'd burn out.
The first two jobs were tempting because feeling like a hotshot sounded nice. However, my two lists reminded me that I would hit a ceiling quickly in those easier jobs and lose interest before long. For the sake of my long-term career growth, I also knew I’d always regret not taking my shot at the really ambitious job. It checked all my non-negotiable boxes and some of my dreams, too.
Ultimately, I said yes to the difficult job, and I thrived. I even got to fulfill my dream of teaching in the classroom, and that set in motion the speaking and writing career that I have today.
There are a million things you could do with your life, but only a few dozen will fit with your natural hard-wiring. Don't make the mistake of following someone else's dream for you because you failed to notice what you were designed for.
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What activities bring you the most energy. Why?
How could you experiment with those areas to learn more about yourself?
What’s on your non-negotiable list? Your dream list?
1 resource: What to Make of a Life
After a dozen years of researching and writing, the organizational scholar Jim Collins has finally released his newest book, What to Make of a Life. After a career spent studying what makes organizations great, Collins now asks, “What makes for a great life?” By synthesizing the journeys of such diverse legends as John Glenn, Benjamin Franklin, and Meryl Streep, Collins shows how successful people navigate the fog and cliffs of life to find work that fuels their inner fire and draws on their natural encodings. No matter where you are in your life journey, it’s a thought-provoking read.




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