Three lessons I've learned the hard way

Sometimes you need to put a fork in the electrical socket. Please don’t, though. It’s a metaphor.

I’ve eaten a lot of humble pie over the last 18 months. Here are some of the lessons I’ve learned the hard way.

People and vision matter more than process

While I was on winter break in December 2024, Matt pinged me and asked, “Would you be interested in running WordPress.com while I’m on sabbatical?” My initial reaction was “no, not really, it seems like a lot of work”, but YOLO was my MO at the time so I said yes.

“Drinking from a fire hose” is a certain form of drowning. Running WordPress.com was like drinking from the entire water main. I went from engineering team lead to being responsible for product development, marketing, customer success, etc. It was a unique learning experience, to say the least.

My guiding hypothesis was that we needed to implement some modern management practices to make the organization more effective. I love EOS, so I adapted some of its systems to Automattic’s culture. Unfortunately, I was wrong in the ways that matter most.

All problems are people problems, and you can’t reorg or delegate your way to solving them. I reorg’d the business twice during my 10 month tenure: once when I started in January, and a second time in May when I was dissatisfied with my first iteration. I thought the effectiveness problem was organizational alignment, but it turned out to be human performance.

Leading with vision requires picking the right challenge, then seeing if you can be even more ambitious. With the humility of hindsight, I oriented the organization towards where the puck was (WordPress hosting), instead of where the puck was going (AI-assisted website building). I needed to take a much bigger swing to have a material impact on the business.

Ultimately, though, my downfall was that I failed to thrive at the executive level. I did a poor job of building relationships and collaborating effectively with my peers. And when my leadership competency came under attack, I took stock of my energy, evaluated my priorities, and decided to move on.

Don’t take a rebound job

Because I get really uncomfortable when I’m not working, I immediately went on an aggressive job search and ended up at PostHog.

I both loved and hated those six months. I loved it because PostHog has a bunch of really talented people (an obvious example of “talent compounds”) and I learned a ton. I hated it because building B2B software wasn’t what I wanted to be doing and my sleep issues got a lot worse.

On the learning front:

• I went 0 to 1 on writing production Python in about four weeks. Thank you, Cursor.
• I realized how little I knew about SQL and substantially leveled up my knowledge. Thank you, Mastering Postgres.
• I knew nothing about applied statistics and learned enough to be successful on the experimentation team. Thank you, blood, sweat, and tears.

Importantly, the experience made me realize how much I enjoy learning, and that my knowledge had stagnated over the last decade.

But, it was the job I could do, not the job I wanted to do. My insomnia got worse, so I eventually left. In hindsight, I realize I should’ve taken the time to decompress, reflect, and wait for the right opportunity.

Treat the job search like a competition

After PostHog, I thought I would spend the next several months watching the AI revolution unfold. I learned again, and finally internalized, that I really don’t do well sitting idle. This time, however, I was a lot more deliberate about my search.

The job market is really tough right now. With many companies mandating a return to office and a few years of progressive layoffs, there is a ton of competition for remote jobs. Additionally, those living in the U.S. are competing with international talent that is a lot cheaper.

As a candidate, it’s easy to feel that your challenge in finding a job is a reflection of your inherent self-worth. The reality is that there are many, many factors outside of your control. Even so, it’s worth doing the best that you can with the factors you can control.

Speaking as someone who is involved in the hiring process again:

• Invest the time into creating a really great resume. So many resumes are poorly formatted, way too long, and stuffed with a bunch of keywords. It makes it really difficult to understand a candidate. Create a resume that’s concise, notable, and highlights your unique accomplishments. You might think brevity will unnecessarily pigeonhole you, but your sole goal is to stand out and make it into the interview process.
• Write a cover letter that explains how your resume and experience are relevant to the organization and job description. Submitting a great cover letter will, again, make you stand out amongst the other candidates who either didn’t submit a cover letter or wrote a poor one. Your cover letter and resume should be examples of the work product you’ll produce.
• Consider a structured search process like Never Search Alone. In particular, I found it really valuable to do Reverse Exit Interviews. They are 15 minute conversations with former colleagues, asking: “What did I do well?”, “What could I have done better?”, and “If you were in my shoes, how would you approach this job search?” The interviews gave me great insights about how others perceived me at work. I also found a lot of value in sending monthly updates to the people I had chatted with. The updates made me realize that I had accomplished something each month, and the replies of support bolstered my confidence.

In July, I started at New_ Public as the Open Source Developer for the Public Spaces Incubator. I really enjoy the people I work with, believe in our mission, and find the work rewarding. The past 18 months have taught me a lot: how to write a cover letter that stands out, why patience matters, and what it takes to be an effective leader. The lesson through all of it, though, is this: do the hard thing and survive long enough to get lucky.