This is the second in a three-part series about how I engineered a better life for myself. Part 1 (here) focused on self-reflection. You should read that first, if you haven’t already.

Having laid down the foundation, it was time to choose what I wanted to build on top of it. Here’s what I did next.

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

Step 5: Chose my water bill

Tradeoffs set the boundaries of what was possible; understanding myself clarified what was meaningful within those boundaries.

This time I decided on an inside-out approach: first leading with who I was, and then seeking opportunities that matched. This led to different tradeoffs. Some were tactical: Capping myself at 25 hours/week ruled out many traditional jobs. Other tradeoffs were philosophical: Making time for exercise, healthy meals, sleep, family, and friends was a priority over career advancement. Younger me would have been aghast.

Self-assessments further helped me understand who I was becoming. I learned how I showed up under pressure, what my motivations were, my learning style, my sources of confidence, my blind spots, and more. It was equal parts humbling and empowering.

Tradeoffs set the boundaries of what was possible; understanding myself clarified what was meaningful within those boundaries. Together they created a compass that guided me toward my next destination with intention, not by default.

Takeaway: Life is full of tradeoffs. The important part is whether you choose them, or they’re chosen for you. Choose your water bill wisely.

Try this: Write down one major tradeoff you’ve accepted to be where you are today. What’s one small experiment you could run to test the boundaries of that tradeoff?

Step 6: Found my best professional fit

With my tradeoffs known, I wanted to see where they led. To find my next step, I turned to the Japanese concept of ikigai, applied to professional options. It has four parts, and where all four overlap, you will find “that which brings value and joy to life.” Hard to go wrong with a Venn diagram.

Here’s some of what I found out about myself for each:

• What I’m good at: Translating complex ideas into actionable terms, deep-diving into health-related topics, building user-friendly financial models, leading difficult conversations with empathy, coaching and mentoring others
• What I love: Mentoring and coaching people through challenges, reading broadly and distilling insights into practical advice, building user-friendly financial models, helping others succeed, running experiments on myself to learn and improve
• What the world needs: Emotionally intelligent and self-aware leaders, practical tools for navigating life’s challenges and opportunities, complex ideas broken down into pragmatic recommendations
• What I can be paid for: A variety of traditional business roles; generalist management consulting; leadership positions like Chief of Staff, COO, or Head of Strategy; running a small business; something to help others grow and find fulfillment

The overlap among the four dimensions was expected. They converged on three career options: a small business owner, a Chief of Staff, and a life coach. The first two made sense. The last one? A surprise. I used to roll my eyes at the idea of “life coaches”. What was that doing here?

Takeaway: When you uncover where your passion, your skills, what the world needs, and what you can get paid for all overlap, you will find your source of value and joy … and where to test first.

Try this: List 2-3 items for each ikigai dimension. What role can you find at the intersection of at least 2 of the dimensions?

Step 7: Did market testing

I now had three viable options to consider. The next step was to choose one. It was time for market testing.

I heard themes of deep work satisfaction, forming strong relationships, flexible hours, and the joys of helping others lead better lives.

I went straight to the source: people in my network already doing those three roles. They generously gave their time as I asked questions about their motivations, the challenges and rewards, and tradeoffs associated with being a small business owner. No amount of desk research could have replaced those conversations.

Here’s what I learned:

• Small business owners: Frankly, I thought this would be the winner. I learned it was incredibly rewarding and intensely demanding. They reported a high sense of purpose and fulfillment, not to mention living life according to their values. But also that this was more than a full-time job, with odd hours and the need to fill in for employees on a moment’s notice. That was incompatible with the tradeoffs I’d actively accepted. So this wasn’t the answer after all (for now), but I filed it away as a future option.
• Chiefs of Staff (COS): I learned something similar from people who were in COS roles: It could be an always-on job, something that wouldn’t easily fit within 25 hours/week. And fractional COS roles weren’t interesting to me, as they could be (from what I found) closer to high-powered assistants. Also not a fit. Two down, one to go. Uh oh.
• Life coaches: I heard themes of deep work satisfaction, strong relationships, flexible hours, and the joys of helping others lead better lives. The tradeoff was a potential ramp-up period before becoming financially sustainable. But connecting this with my earlier dashboard work (which had shown I had some financial runway to do experiments) revealed a strong match.

Wait, what? This was a surprise. I hadn’t seriously considered life coaching as a profession for me. But all the data pointed to that being the best fit. And data, like hips, don’t lie.

Takeaway: Desk research has its benefits, but doesn’t compare to conversations with people who are actually doing the work.

Try this: Pick one role and schedule a 20-minute conversation this week. Ask two questions: “What was your hardest tradeoff?” and “What was your biggest surprise?”

Part 2 wrap-up

My work so far had expanded my view of what was possible, then narrowed it down to an option I would never had thought of before, yet was aligned with my values, skills, interests, and tradeoffs. This was serious progress from my knee-jerk reaction of applying for consulting jobs just because I didn’t know what else to do.

But big questions still loomed:

• How could I stand out as a life coach?
• How would I take it from idea to reality?
• What else did I want outside of work?

The next step was about going from choosing to actually building. Stay tuned for the final post in this series (link). There’s a ukulele involved.

In the meantime, if you need help narrowing down a set of ideas to find the one that fits best for you, download this worksheet for part 2, and let me know what else you learn about yourself.