This April, I made a big life change and switched companies after nearly four years at the previous one. Every time I say I’m taking a sabbatical, it never happens. One day, I’ll make sure it happens. I took about a week off before advising with Replit, then ultimately joining the company. Many people ask what made me choose the software creation platform over other opportunities I had, and I’ll share with you my framework for choosing.

"What are you optimizing for?"

I've asked this question to every person I've interviewed as a hiring manager for the past seven years. "What are you optimizing for?" helps candidates think bigger about what’s important to them in their next opportunity. Though title and comp are important factors, there are more underlying motivations, sometimes not realized by the candidate in conversations. Recruiter or hiring managers should understand candidate needs and work backwards from there.

Answers from candidates may be surprising. It might be a Software Engineer wanting to move into a Technical Product Manager (TPM) or a Product Designer with the desire to make impact in a different industry. Perhaps it is looking for a different pace/cadence in their work life. Take a look at my own notes of my optimization list.

My handwriting is terrible, so I’ll transcribe:

• Early stage company building

• Design/dev tools, Marketplaces, or Creator Economy

• This might be my last job as an operator. Make it count.

Here’s the kicker—I wrote this list before I joined Webflow, not after I left. My optimization list is something I’ve had clarity for several years and not only after I decided to leave. This artifact helps you guide what you’re looking for. What you optimize for doesn’t show up in job descriptions or aggregators. They emerge in conversation. Once you know what you're optimizing for, stack rank priorities.

The three P's

On the Design MBA Podcast, Lattice SVP of Design Jared Erondu spoke about the decision to join Lattice as a founding designer after doing High Resolution. He mentioned three P's for him: People, Purpose, and Pay. Inspired by Erondu (which we all are), I reflected on my own of what a post-Webflow world looked like for me. My stack ranked three P's were Purpose, Product, and People.

Purpose

Kimber Lockhart, my first manager and the person who hired me at One Medical, wrote, Don't create a sense of urgency, foster a sense of purpose. This mantra stuck with me everywhere else I’ve gone. For me, purpose is your life version of being mission-driven.

Work is a big aspect of my life, and it’s the best environment for me to contribute to something meaningful. Purpose in the workplace can be multi-fold. It could be helping build a product that has a positive impact on the world, helping the company scale effectively, or growing humans on the team. My hope is what I contribute to exceeds my own lifetime.

Product

If I can’t be excited about the product, I won’t join the company. The product is the artifact that delivers purpose. Regardless of title, compensation, or any other incentives, I will never work at a company where I don't believe in the product or can’t be enthused by developing it. I have no interest in being a Chief Design Officer at a place where material change can’t be made and the product is shitty. I care more about the product and what can be achieved vs. the notoriety of design leadership royalty.

People

At first glance, this may be surprising for some that People is the last one in this stack rank. It doesn’t mean I don’t care about people, but if Purpose and Product aren’t right, it doesn’t matter who I work with. There are many people in my career I’d love to work with again or start something with friends, but if it’s not the right company, it doesn’t matter. That said, it’s usually the case I’m working with people at multiple companies that check all three P’s.

I optimize work for working, not making friends. I’m not looking for a family at the workplace and there to achieve something with a team. Through that, many friendships are formed organically; not optimizing for it, but they happen.

Understanding the signals and anti-goals

As you have conversations, identify what signals might tell you if a role is a good fit for you. Signals aren’t red flags and more factors to help you consider making a decision. One person’s red flag might be another person’s green flag. It all depends on what each person is optimizing for. For example, something I optimize for is working at a company where I know it’s a multi-year effort, not because I want to rest and vest, but know it’s going to be a long-term investment. In one of the interviews I had, I mentioned this. The person’s answer was, “Oh, you could be here a year.” That’s when I knew it wasn’t the right fit for me. Again, the opportunity was great and I didn’t view it as a red flag but had the utmost clarity in what I was seeking.

Anti-goals come before signals and are a strong filter before conversations. These aren’t essential, but they help in creating constraints to guide you along the way. A few of the anti-goals I established were:

• I do not care about title whatsoever. I’m in a privileged point in my career where it’s no longer important

• Org size: I’ve led teams 30-40 people before. I knew in a market decimated by layoffs and the rise of AI, orgs would look differently and number of people on the team wouldn’t be a measure of success

• No repeating of “the same job.” I wanted to make sure wherever I ended up presented a new challenge and opportunity for me to grow as a person.

Recap

Don't spend all your time career planning, but have an idea of what makes sense for you. Like all the good things in life, they happen organically when you’re not trying too hard to make it happen.

1. Identify what you're optimizing for

2. Establish a priority framework (Note: they don't have to start with the letter P)

3. Understand signals and anti-goals

The reflection I ask people who are considering a job change is, "Are you running towards an opportunity or running away from one?" If the place you work at is a dumpster fire and you need to get a new job immediately, then GTFO. However, if what you're running towards isn't clear and the current role you're at is meeting your needs, then create more time. Having this rubric already established made it obvious what the right choice would be.