Minimizing Regret

Friday, June 18, 2021 was my last day at Facebook.

I was with the company for just over two years. In my brief time there, I bootstrapped a product and a team focused on delivering Facebook's next-generation advertising products: privacy-preserving, high-performance, and not under the control of platforms owned by competitors. I'm proud of that work, and look forward to seeing that effort redefine the digital advertising industry.

Toward the end of my tenure, I also spent a lot of time shaping some new product initiatives outside of advertising that I can't talk about publicly, but that are sure to redefine Facebook, both in terms of culture and how it serves customers in the market.

It's not often that someone is given these kinds of opportunities. Each of the four initiatives I helped set in motion during my short time there will impact millions of businesses, and billions of people. Billions of dollars will be made or lost. Industries be redefined by Facebook's mere presence.

That's pretty amazing.

And the people... the people I worked with at Facebook were among the best I have ever met. There is something incredibly energizing about showing up on Day 1 and realizing that you're the dumbest person in the room—that every single person there will teach you something, whether you like it or not.

While I believe that we can always be learning, it's rare to find an environment where everyone is so willing—even excited—to always be teaching.

So why leave?

Many have asked me this. It's a reasonable question. I had some wins under my belt, rave reviews from leaders across the company, a great career trajectory with huge upsides ahead, an incredible manager who I genuinely loved working with, and this amazing set of peers supporting my growth.

While battling this question myself, I ultimately had to answer just two questions.

Question 1: Do I believe in myself?

It's easy to trick yourself into taking credit for success that isn't really yours. This is one of my deepest fears: growing willfully ignorant of my own inadequacies, fueling a downward spiral oscillating between self-doubt and self-delusion.

It's easy to stumble upon a rocket ship that's about to take off, to strap yourself in, and then to take credit for arriving at the destination—even if your biggest contribution was acting as a counterbalance to dead weight elsewhere in the vessel.

When you join an established, already-successful company, you join a place that—almost by definition—already has a lot of the machinery to help make people successful.

Internal platforms exist to accelerate development and experimentation. Performance programs exist to ensure the organization is keeping and rewarding the best talent. Product management machinery exists to help product teams make the best decisions. Go-to-market machinery exists to build and leverage relationships that ultimately help with sales.

As an engineer at a company with those tools, you have a huge advantage. You can focus on just your little slice of the world, and have faith that the rest of the machine will carry your incredible ideas to success.

Unfortunately, this applies even if your ideas are not so incredible. It's easy to hide bad decisions in a large organization. It's easy to take credit for the wins, and blame others for the losses. It's easy to "ride along" and just let momentum carry you forward.

While this perverse form of psychological safety is useful early in your career, eventually it stunts your growth. It prevents you from taking real risks, from pushing yourself to stake something meaningful.

Nothing ventured, nothing gained.

Question 2: Which decision will I regret when I'm 80 years old?

The "Regret Minimization Framework" was named and made famous by Jeff Bezos. Asking this question forces you to take a long view of success, looking beyond money, or status, or peer pressure.

It forces you to imagine what a life well-lived looks like, and work backwards from that vision.

I knew that I would not regret leaving a stable, successful company to make a bet on myself—even if I ended up failing.

I knew I would be proud to tell my children and grandchildren about the calculated risks I took and the hardships I faced, regardless of the outcome.

Ultimately, asking these questions made the decision to leave incredibly simple.

Whatever the benefits of staying at Facebook, I knew they'd be successful without me. I knew I wasn't really staking anything by staying, even if the impact and rewards were large.

I knew I wouldn't be growing in the ways I wanted to.

And once I realized that, I knew that if I didn't make this bet—on myself, and on this new opportunity—I would be haunted by regret for years to come.

Onward and Upward

On Monday, June 21, I begin a new role at AudioEye, a SaaS company dedicated to "eradicating every barrier to digital access." It's a small company with big dreams.

We have a solid, industry-leading product. Business is growing, and we're having to constantly reinvent ourselves just to keep up with our success. We have built a strong leadership team, which I'm happy to be joining.

And, after we succeed, AudioEye is a company that I will be proud to tell my grandkids about when I'm 80.