I got off the call in shock. The startup where I’d been for 2.5 years was shutting down the next day. I was suddenly unemployed.

I’d been trained to think that being unemployed was wrong, even borderline shameful. That awful purgatory where you wallow aimlessly in the midst of half-baked projects, hoping for a lifeline of new work to save you. Every fiber of my being told me to get back into the workforce immediately.

Still shaken, I refreshed my résumé over the weekend. I was on autopilot, looking for what I knew best: business consulting. I’d been a consultant for nearly 15 years; it was my safe space. It was familiar. It was well paid. It was … fine.

But a quiet voice whispered to me: “fine” wasn’t good enough. Something was missing in my life. Something I wouldn’t find if I settled for “fine”. So I turned off autopilot and listened to that voice. I’m glad I did.

What followed was months of self-exploration. The experience was messy, energizing, and full of doubts, but I ended up somewhere much more rewarding. The journey reminded me that there was more to me than work and ambition: I was a father, a partner, a son and brother, a friend, a community member, and someone who needed to take care of himself in order to be there for it all.

Here’s what I did, step by step.

Plus see below for an accompanying worksheet so you can try it for yourself.

Step 1: Faced my emotions

I was taught that emotions don’t belong at work. My first job was in finance, where it was numbers only, no feelings. The quote from Wall Street summed it up: “If you need a friend, get a dog.”

The first breakthrough came when I named my overriding emotion: fear.

That mindset stuck as I advanced rapidly in the corporate world. Each new fancy title, each additional responsibility, I just ran faster, never sparing a thought for my emotions.

This time I couldn’t. I was emotionally drained. Post-pandemic and post-startup, I was out of gas.

So I let myself feel. I wrote. I walked. I talked with friends. I exercised. I tracked my emotions: what I felt, when, and why. Soon a pattern emerged. The first breakthrough came when I named my overriding emotion: fear. Fear of failing. Fear of risk. Fear of mistakes.

I realized I’d lost confidence in myself. Superpowers I’d relied on for decades — presenting, leading teams, figuring things out — suddenly felt out of reach. I was blaming myself and my lack of skills for the startup’s failure. Leaving consulting to join the startup had been a big leap of faith. When that fell apart, I didn’t know if I had it in me to take another leap.

Once I named it, I could reframe it. I wasn’t broken. I had just been in the wrong environment. The startup failed for reasons unrelated to my abilities. Failure became experience. Wounds became resilience. Fear became fuel.

To drive the point home, I ran a short experiment: I offered free coaching to a small group of friends, on topics ranging from personal to professional challenges. Two things happened: I learned I still had my superpowers. And I realized I loved helping people. (Actually a third thing also happened: My wife thanked me for helping someone other than her for a change). That tiny win was a pivot: data > doubts.

Takeaway: Don’t ignore emotions at work. Name them, reframe them, and use them to move forward.

Try this: List three emotions about your life or work, and create one small experiment to reframe each.

Step 2: Took stock of where I was

Next I needed a baseline. Not “What job do I want?” but “Where am I today?”

I built a personal dashboard focusing on health, finances, key relationships, career, and professional leadership. For each category, I figured out what mattered most to me. As an example, my health goal wasn’t to run a marathon or compete in weightlifting championships. My goal was to play with my kid without throwing out my back and go on hikes with my wife, for years to come.

Here’s some of what my dashboard showed:

• Health: Good overall, but blood work flagged some risks.
• Finances: Enough runway to do some experiments.
• Key relationships: Important ones slipping.
• Career: Time constrained to 20-25 hours/week, max.
• Professional leadership: Desire to help others grow and feel fulfilled.

Takeaway: Before you plan your next move, know your assets and your constraints.

Try this: Fill out your own dashboard (see link to worksheet at the bottom).

Step 3: Rewrote my story

Even with this clarity, I was still looking backward: thinking about what I’d done, not who I could become.

Now in my 40s, I was blessed to have a much fuller life than ever before. But I also needed to balance aspects of my personal and professional life differently. I used to shake my head at people who had to leave work early to “pick up their kids”. (Aside: I’m sorry to anyone I used to give a hard time about that before. I so get it now.) My life was richer, but I was still applying old models of success that no longer fit.

Two insights followed. First, I always have been and forever will be a work in progress. Second, I get to decide who I’ll become next.

Takeaway: Growth never stops. Who you were got you here. Who you’ll be next is up to you.

Try this: List 3 examples of when you thought you had something figured out, but later your understanding grew.

Step 4: Identified my values (bonus: and my new identity)

I wasn’t just a worker anymore. I was someone who uses what he’s learned to help others grow and gain fulfillment.

The answer came when I embraced my core values. Among other values, I’ve always loved figuring out hard problems. As a lifelong generalist, I valued connecting dots between various aspects of life to provide a holistic view.

With that clarity came a new identity: I wasn’t just a worker anymore. I was someone who uses what he’s learned to help others grow and gain fulfillment. Suddenly my choices made sense.

Takeaway: Before making a big change, go back to who you are at your core: your values.

Try this: Identify your top 3 life values, and the behaviors that support them.

Part 1 wrap-up

By not settling for “fine” and instead doing the hard work of getting to know myself better, I turned fear into experiments and experiments into goals.

That’s the part I’ll share in my part 2 (link). Stay tuned.

In the meantime, if you’re at a pivotal point in your life, unsure if you’re living in accordance with your values, or just curious to dive deeper into where you are today, download this worksheet and let me know what you learn about yourself.