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Reboot (& Reflect)

I’m in the middle of a self-imposed career reboot. On good days, I celebrate what I’m calling my Year of Responsible Risk. On bad days, I obsess over why I need this reboot and why I’m not enjoying this process more.

I quit my last job (without another job) after realizing - for a variety of reasons - that it just wasn’t working anymore. As a lawyer temperamentally opposed to risk, this was a big deal. Initially I assumed that I would spend my unemployment period looking for that elusive legal job with the perfect working environment. So far, I’ve been wrong.

Career Reboots Take Work

My year started with a budget and a few plans. At some point, I knew I needed outside help. I’ve reconnected with a college friend who keeps me on task with biweekly calls and purchased too many self-help books. Eventually (and reluctantly), I hired a coach to help me focus on what I really wanted to get out of this reboot. Did I really want another legal job or do I want something completely different?

I used to shun such introspection. Strength-finding exercises, questions about what I’m passionate about right now, etc. And while not always fun, it has helped. It has focused me on the parts of the legal process that I do enjoy. And it has given me a clearer idea where I want to go.

My advice to everyone is this: make time for this work now. Don’t let your career happen to you. To state the obvious: the more you know about your strengths, your values, and how you work best, the easier it is to figure out your next steps. I wish I had done this work much, much sooner.

Your Strengths are Skills

One big reveal has been that some of my strengths—ones I took for granted and assumed everyone had—are actual skills. I suspect I’m not the only one who has failed to appreciate their talents.

My strengths revolve around thinking critically—analyzing issues from different perspectives and helping people work together by understanding each other. In the liberal arts tradition, I can find links between ideas, apply lessons from other contexts, and question assumptions. What are yours?

Critical Thinking is a Thing

Raised to “think also about this,” educated at a liberal arts college, and trained as a lawyer, I was surrounded by people with similar skills . . . until my last job. As the lyric in Big Yellow Taxi goes, “you don’t know what you’ve got till it's gone.”

The powers that be at my last job rewarded “we have always done it this way” behavior and built technology systems without first understanding the problems they were trying to solve. When I tried to find solutions by pointing out how one settlement was different from another, asking for outside experts’ opinions, or questioning assumptions, I was shut down.

When I quit, I knew that whatever work I did next had to be collaborative and include diverse perspectives because that is how to solve problems. What I didn’t know then is that what I’m looking for is a “thing.”

In The Fuzzy and the Techie, venture capitalist Scott Hartley implores businesses to seek collaboration between the humanities and technology fields or risk “rapid obsolescence.” According to Hartley, what matters is how you think, asking the right questions, and understanding the problems you’re trying to solve. And as one recent article points out, “[f]rom Silicon Valley to the Pentagon, people are beginning to realize that to effectively tackle today’s biggest social and technological challenges, we need to think critically about their human context.”

And so my Year of Responsible Risk continues with more focus than I had when I started. While I’m very grateful for this time to explore, it has been much more stressful and required more work than I thought. My career advice to you at my midpoint: figure out your strengths, ask questions, and challenge assumptions.


Amy Gernon lives in Northfield, Minnesota with her husband and four children. She has practiced law for over 15 years, where she enjoys building consensus and finding ways to resolve and effectively manage complex civil litigation.

Amy is also in the beginning stages of developing an advising consortium that pairs dynamic liberal arts academics with individuals and businesses to help them rediscover critical thinking skills, solve problems, and find inspiration through thought exercises.

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