Picking Rocketships Is a Bad Career Strategy
Hi! I’m Molly. I write about what it actually takes to lead inside growing, changing companies: the frameworks that help, the truth about what it feels like, and the messy work of shaping a career that actually fits.
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In the tech world, we’ve spent the last twenty years romanticizing rocketships.
There’s a famous piece of advice that Eric Schmidt gave to Sheryl Sandberg: When you’re offered a seat on a rocketship, you don’t ask which seat. You just get on.
It was great advice for that moment in time. There really were a handful of companies where you could see the trajectory clearly. You could reasonably predict they were going public. You could look at the landscape and say, “Those four or five companies are going to define the next five years,” and you would likely be right.
It is much harder to do that today.
The tech ecosystem is exponentially more crowded. Capital is abundant and moves faster. Product cycles are shorter. Right now, with AI, it’s even harder to distinguish what is a feature, what is a product, what is a company, and what might actually become a generational business. Everything looks like a rocketship at first glance.
I’m honestly looking at a lot of the $100m and $200m ARR companies — what used to be an incredibly hard milestone to reach — and wondering how many of them are going to go to $0. Almost nothing feels predictable to me right now.
So if your strategy is simply “pick the rocketship,” you are building your career on a detection system that is increasingly unreliable.
My ultimate litmus test for a job is: If this company struggles or fails, will I still be glad I took the job?
Companies are fragile. Even the generational ones.
I’ll never forget a conversation I had with someone at Facebook in 2012, a couple of months after we went public.
For those who don’t remember, we debuted at $38 and then the stock fell to $18. It was a rough period inside the company. The press was brutal. The narrative was that we had overpromised and underdelivered. There was real doubt.
We had acquired this person’s company not long before the IPO. He told me, very calmly, “I just can’t see why it’s a good idea for me to stay.”
A bunch of us tried to convince him to give it time. To believe in the long-term version of the company. But he left within six months.
In hindsight, that may have been the worst financial decision he ever made.
But here’s what matters: at the time, it was not obvious. At all.
It did not feel inevitable that the stock would someday be at $100, or $300, or higher. When it got back to $55, many friends sold large portions of what they were holding. Even the companies that later look unstoppable go through moments when they look and feel broken.
If you try to time your career based on whether something feels like a rocketship in that moment, you will almost inevitably become a fair-weather employee. You’ll leave during the uncomfortable middle. You’ll second-guess during volatility. You’ll anchor your conviction in market sentiment rather than substance.
I once worked with a founder whose company had been hyped for years. When a negative press cycle hit, employees started quitting in waves. It turned out that many of them had only joined for the best-case scenario. When the story turned, they bailed.
That’s the danger of building your career around success narratives. They change.
(One of the greatest articles ever written about the hype cycle of companies was written by Aaron Zamost 10 years ago. If you’re inside a generational or generally hyped company, read it immediately. It helps you weather the storms to understand the cyclical nature of hype cycles…)
You Can’t Control the Outcome
With startups, it is as likely that your stock will be worth $0 as it is that it will be worth millions. You can do all the homework. You can assess the founder, the market, the product, the cap table. You can still be wrong.
Fundamentally, you cannot control whether you end up inside a success story.
What you can control is what you take with you.
What you learn.
What you experience.
The relationships you build.
Those are compounding assets.
Did you build something from scratch? Did you manage through ambiguity? Did you ship under pressure? Did you see how decisions get made when stakes are high? Those skills travel with you.
The experiences matter even more than we realize at the time. A messy, volatile period can sharpen you more than a smooth ride ever will. Managing a thin-margin business makes you a better operator than watching a graph naturally go up and to the right. Being inside a storm teaches you things that stability never can.
And then there are the relationships.
The only thing you are guaranteed to take with you, other than what you learn and experience, is people. The peers you trust. The leaders you respect. The people who would work with you again in a heartbeat.
When I was at Google, I worked in Communications. We grew from a team of 25 to 125 in about a year and a half. I wasn’t there that long, but I built friendships that lasted. Many of those colleagues went on to run communications at Tesla, Square, Twitter, and other next-generation startups. Suddenly, I had trusted relationships across the industry.
Those connections created optionality that no stock grant ever could.
Strong work relationships are almost a greater long-term outcome than money, particularly early in your career.
A Better Litmus Test
Instead of trying to predict which company will win, you ask whether the work will grow you. Whether the problems are interesting enough. Whether the stretch is meaningful enough. Whether the people are worth investing in.
You can still believe in the mission. You can still hope for the best possible outcome. But you’re no longer betting your entire career logic on whether you’ve perfectly identified the next generational company.
Even if you have joined one, there will be moments when it looks like it’s failing. Markets fluctuate. Strategy pivots. Narratives turn.
The people who build durable careers are not the ones who perfectly timed entry and exit. They’re the ones who were convicted enough — about the mission or, better yet, about their own growth — to weather the storm.
So when you’re evaluating your next move, don’t just model the upside.
Model the downside.
If this company struggles or fails, will I still be glad I took the job?
If the answer is yes — because you’ll grow, because you’ll build real relationships, because you’ll sharpen skills that compound — then you’re betting on something you can actually control.
And that’s a far sturdier strategy than trying to predict the next rocketship.
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