What are you optimizing for?

I have a lot of career conversations (interviews, reports, chats with people asking for advice) and the single clarifying question I’ve grown to center the discussion around is this:

What are you optimizing for?

I left Squarespace in July after an eight year run. To reiterate what I said in that post, Squarespace changed my life. I grew up as an IC at Etsy, and I grew up as a manager/leader at Squarespace. And both on paper and in practice, it was a great role - a wide managerial scope (3 orgs / 12 teams / 85 reports), the carried reputation of successfully building International from the ground up, and the opportunity to work with a diverse set of smart and kind coworkers who operated in good faith. I had no major complaints about my compensation or work-life balance. I genuinely enjoyed those whom I worked most closely with as people.

Which naturally begs the question: why did I leave?

During The Great Resignation of 2021-2022, I didn’t take any interviews. While fully remote opportunities with bigger titles and sky-rocketing compensation were available, it wasn’t the right time. International wasn’t what it could be, yet. I was determined to get a few deserving teammates promoted. My family was navigating a personal tragedy. And in the midst of Covid lockdown, my wife, young son and I were slowly losing our minds at home. In the scope of what I was optimizing for most - personal stability, achieving International’s vision, my reports - an elevated title and more money weren’t my priorities.

And you know what? It was the right call. We needed the stability at home, International changed the face of the Squarespace business, and nothing gave me more pleasure as a manager than facilitating career growth for many excellent teammates. It was truly one of the best parts of my job.

Fast forward to 2025 and the opportunity at Imprint came up in May. For the first time in many years, the things I was optimizing for (both personal and professional) had meaningfully changed:

• My family life felt more stable. My kids are a bit older now, and while I become a chauffeur starting at 5pm every day, their days (and most importantly nights) are increasingly predictable.
• Purchasing a house we loved gave us a sense of location permanence and a community to invest in.
• I wanted to feel more shared urgency at work, and I wanted the shared organizational incentive of an exit / financial outcome to override any cross-functional complacency. I was ready to trade off a less predictable startup work schedule for this urgency.
• I’ve learned a lot from Will and his writing over the years, and I wanted to work with him directly.
• Imprint was an order of magnitude smaller - 150 people, ~40 engineers - with booming financials and a nascent engineering culture. I’ve built enduring engineering teams and cultures. I wanted to know if I could do it again.
• I stopped caring about management vanity metrics like reporting number and org size. I know I can do that job. I wanted to get back to feeling like I was actively pushing the business forward, and was happy to frontline manage teams again in order to do so.

What people value at a given time varies: current liquid compensation, future stock compensation, title, work-life balance, job stability, the challenge of building something significant, the convenience of building something insignificant, a leadership chain you believe in, etc. The mistake I see most often is assuming those values must be static or universal. None of these are more or less right or wrong than others, and they’re fully contingent upon context and timing.

Thinking about this question has grown me in a few specific ways:

• When you sell candidates on joining your company/team, how does your framing of the opportunity match what the best fit candidate is optimizing for?
• As a leader/manager, how much does your culture and practices match what your coworkers were optimizing for when they chose to accept their jobs?
• I have grace (for others, for myself) when highly valued coworkers move onto new companies. Sometimes the reasons are work related, sometimes they’re not. Often it’s a messy mixture of both. Despite any feelings of disappointment, be happy that they’re making the best decision for them. In the grand scheme of things, jobs come and go, but strong relationships with amazing coworkers who you’d be happy to work with again are few and far between.

My enduring advice to job seekers is to know what you are optimizing for, and navigate your search and interviews through that lens. Knowing what you’re optimizing for doesn’t guarantee the right outcome, but not knowing almost guarantees confusion.