I quit my tech job, here's what I learned

Why PM is not CEO, and how to be valued

It’s been over 30 days since I quit my PM job. I’ve never been happier. 

This is a welcome change because for most of my life, I’ve struggled to be happy. While I was never seriously depressed, my baseline has always been a tinge of blue, like a mild version of Sadness from Pixar’s Inside Out. 

Biggest thing that changed? Control over my time. 

With that said, it’s not all sunshine and rainbows. There are things I wish I knew earlier. I hope they inspire you to turn your raw experience into valuable assets, not just years on a resume.

You’re flying in a simulation

Each supporting team creates a layer between you and the real world. It’s nice to have engineers, sales, and growth marketers fill in the blanks for you. They sweat their details so you can focus on what you do best. 

But when you build something that takes off, what feels like exhilarating flight is, in reality, flight simulation. You are more sheltered than you think. Knobs you didn’t even know existed in the cockpit have been taken care of.

I thought I escaped the simulation by working at an early-stage startup. Not so much. 

Prior to spreading my wings, I never had to think deeply about marketing and sales. The simple fact that we already had customers and ways to reach them made the experience less raw. Even 0 to 1 products usually targeted a similar customer base. Monetization is also often an afterthought because the core business can afford to fund experiments.

I thought I was an end-to-end product owner, but that’s only because I spent my entire career in a simulation. There were always things that were “someone else’s job”.

Why PM is not CEO

In building a business, there are four non-negotiables:

  1. Worthy problem
  2. Distribution to reach customers
  3. Monetization
  4. Differentiated solution

This is just Business 101, but what you don’t often hear is how the PM job only covers maybe the first and last parts. This is by design, as each part is stressful on its own. By doing fewer, you do them better for your company. 

But for you, it’s important to be intentional about the scope of your job. What are the crucial skills for your next act? Stay close to them. 

A company’s job is to make you increasingly valuable to them, but your job is to be increasingly valuable to the world. 

You do better by cultivating more quality options over time, not becoming a shiny cog that only fits into one machine. Sometimes, the company’s incentives are aligned with yours, but it’s not a given.

Every skill you gain doubles your odds of success

Not every skill is made equal, but being interdisciplinary will grow in importance. 

A global talent pool means that the bar for “world-class” in any given skill is only going to keep rising. Rather than sweating in the Red Queen’s race, consider adding new, lateral skills to your toolbox. It will make you more antifragile.

In my case, I would’ve spent more time learning sales and growth marketing — the distribution side of the house. Being more full-stack / self-sufficient is critical to operating outside a fully-resourced company. Teaming up with people with complementary skills can help, but no matter what the early days will always seriously stretch your capabilities. 

I had a laughably hard time even coming up with sales copy for my first paid product. I was wordy, unclear and spent too much time focusing on features, not benefits — the classic rookie mistakes. 

I used to think sales was icky, but I realize now it’s about giving people a reason to care.

Whether you’re trying to get a promotion, or a side hustle off the ground, let go of all the fancy stuff you’ve done, and instead focus on how you can help people. Point out the problem, then provide the solution.

The price of a brand name

As it turns out, I suck at branding.  

I never had to work at it because I’ve always coasted off of brand names like Harvard and Bain. I thought they proved that I “made it”. Little did I know that the price of living off a brand name is to live by someone else’s rules. 

The price may be worth it when you’re getting started. Subsequent doors open a little more easily. But a lifetime of trading one brand for another is not only empty, it also caps your upside just as it limits your downside.  

If the brand’s reputation precedes your own, your fate is tied up in how that brand fares. The alternative is to build your own reputation. 

In my case, I would’ve spent less time obsessing over prestige, and more time learning skills that create rather than extract value. I would’ve experimented with building alternative sources of income to validate that I’m trading time for money in my day job, but also gaining skills that the market cares enough to pay for independently.  

Even if you have no intentions to do your own thing, the secret to being valued by your company is to have plenty of great alternatives. The only way to know for sure is to explore your options and benchmark your market value. The reason I was able to negotiate boldly with Instagram was because I knew I could walk away. 

People will only ever value you as much as you value yourself.

You are the largest shareholder in a private company: You. And being dependent on a single, irreplaceable source of income is a fragile way to monetize your assets.

Being happy is a skill

I read a book that broke down the happiness formula into three ingredients: being healthy, expecting the future to be good, and a flexible schedule. While you can’t concoct these ingredients instantly, you can in the long-run.

First, make sure you’re not just becoming a better cog, but a more valuable asset to society. One way is to pursue a variety of skills that make you unique and self-sufficient. Test that you’re headed in the right direction by checking if the true market values it. By cultivating alternatives to a single paycheck, you can then trade for things that make you happier, like a flexible schedule.

You can also experiment venturing into the wilderness at some point. At best, you learn new survival skills and maybe even rewrite your baseline happiness. At worst, you gain a deeper appreciation for your cross-functional partners, and the luxury of life in a cozy simulator.

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