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Every two weeks, I share my writing on investing, career transitions, meaningful work, parenting, living intentionally, and other topics that engage me.

I'm still trying to figure stuff out.

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Systems and Serendipity

I approached my recent job search like any good former analyst would.

Systems, spreadsheets, and carefully planned processes felt natural. After all, my previous career pivot two years ago had worked out well, so I thought I knew the formula.

Update resume. Network strategically. Interview effectively. Negotiate offers.

Simple, right?

A month into my new role at Bath Savings Trust Company (BSTC), I can laugh at my former certainty. The skills that serve me well in my professional life became my biggest blind spot during the search.

Learning to Let Go of Control

My first and hardest lesson came from realizing I couldn't spreadsheet my way to success.

Throughout the process, I tracked every meeting and follow-up in a tidy Notion database. I created schedules and timelines. I refused to take days off, convinced that working harder would somehow accelerate the process.

But that's not how it works.

As it turned out, my new position originated from a casual conversation at a friend's birthday party that led to a key introduction. This seemingly random interaction completely changed my path.

Last summer, in a Beyond the Cove essay called The Neutral Zone, I referenced the term that William Bridges coined in his book Transitions.

I summarized Bridges’ definition as I prepared to embark on my search. I wrote, “This uncomfortable middle stage is where the old way has ended, but the new way has yet to solidify. It’s a time of uncertainty, where the path ahead isn’t always clear.”

While I understood the idea, I didn't fully understand how hard it would be to accept that some of the most valuable developments can't be scheduled or optimized.

The real breakthrough came when I stopped seeing uncertainty as a problem and started seeing it as a feature.

Build your spreadsheets. They'll keep you organized and accountable.

But leave room for unplanned conversations, surprising connections, and most importantly, the internal evolution that can't be rushed.

The Perfect Role Myth

My second major hurdle was letting go of perfection. I believed each potential role needed to be the ideal next step toward my ultimate career destination. This mindset created unnecessary pressure and limited my options.

A conversation with a mentor changed everything. "What if you just looked for a role that feels right for now?"

This simple question cracked open my rigid thinking. I started seeing opportunities differently:

• A role might build new skills
• It could provide stability while I explore
• Perhaps it would evolve unexpectedly
• Maybe it would surprise me by being exactly what I needed

When Process Becomes Power

My analytical habits weren't all obstacles. Once I stopped fighting uncertainty, I found ways to make my process orientation work for me.

After each conversation and interview, I'd update my Notion database with feedback, follow-ups, and my key takes from the meeting. These structured reflections helped me recognize patterns in what energized me versus what left me flat.

Without this systematic approach to self-discovery, I might have missed the emerging pattern that ultimately guided my decision.

Through this systematic reflection, I discovered a clear pattern. The roles that most energized me all involved direct client relationships, something I hadn't even included in my initial job criteria.

The Standard Advice Still Works

While wrestling with control and perfectionism, I also relearned some classic job search wisdom. Be specific in your networking asks. Build genuine relationships that outlast your search. This advice appears everywhere because it works, even for those of us who prefer systems to small talk.

A Final Note to My Fellow Process People

Your planning skills matter, but they work best as support tools and guides rather than strict formulas. Remember:

• Planning skills help but don't guarantee outcomes
• Uncertainty belongs in the process
• The right next step matters more than the perfect one
• Relationships matter more than spreadsheets

Most importantly, your process orientation and analytical skills aren’t weaknesses. They’re strengths that need minor adaptation. Create a structure where helpful, but learn to release control where necessary.

The path forward might look different from your carefully mapped route.

That's not only okay. It might be exactly what you need.

Looking back from my new desk at BSTC, I can see how each "imperfect" step in my search process led me here. The role brings together two important elements: the client relationships I discovered I wanted and the analytical skills I already had. It's a combination I might have missed if I'd stuck too rigidly to my original plan.

My spreadsheets still exist, but now they track client meetings and project milestones instead of networking meetings.

The process person in me hasn't disappeared. He just leaves more room now for the unexpected opportunities that make work and life more interesting.

Other Stuff

Alternative Investments in 2025: Our Top Five Themes to Watch It was interesting to see US Value Add Real Estate at the top of JP Morgan Private Bank's expected returns for alternative investments over the next 10-15 years. Of course, I take this with a grain of salt like all forecasts, and I'm certainly guilty of confirmation bias... but still! Persistent supply shortages remain the key fundamental driver of their investment thesis. Other than US Housing, top themes include AI-fueled demand for energy infrastructure and normalizing interest rates plus deregulation fueling capital markets activity.

​Read the outlook (9 mins)

On Fleeing the Inferno A heartfelt first-hand account of the LA fires from Lawrence Yeo of More To That, one of my favorite writers online.

​Read the essay (6 mins)

Alfred Lin: Strategic Thinking for Startup Success In this episode of The Knowledge Podcast, Shane Parrish hosts Alfred Lin, Sequoia Capital partner, who I hadn't heard interviewed before. They dive into the art of strategic thinking for startups and general business strategy. The conversation comes alive as Lin shares lots of detailed stories from Zappos, Airbnb, and DoorDash. This was one of my favorite TKP episodes in recent memory.

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​Listen to the podcast (2 hours)

And a Farewell Photo...