I’d bet that right now, more people are considering whether to change jobs than ever before.
Life inside most companies is hectic as they sprint to adopt AI and redesign the org around it. Everyone’s job descriptions and expectations are changing rapidly.
At the same time, new companies are getting traction faster than ever. It seems like everyone else is getting rich at startups that didn’t exist 18 months ago.
All of this chaos and opportunity has a way of dredging up existential career questions.
So, should you quit?
From the hundreds of conversations I’ve had with people on my teams trying to make this decision, I’ve learned there is no good framework you can offer. The decision is just too personal, too emotional, too subject to the constraints and commitments in their lives.
But there is one thing that does seem to help: steelmanning both sides.
As I give them the best reasons to quit and the best reasons not to, their eyes often light up when they realize they’re more excited about one line of reasoning than the other. And that is their answer.
So that’s what I’m going to do here. Using the two best reasons for each, I’m going to try to talk you into staying. And then I’m going to try to talk you into leaving.
You should stay, because your time at a company compounds
Like any investment, a job is a J-curve. Your time is the x-axis, and the return on that time is the y-axis:
When you first join, that ROI is negative for both you and the company that hires you. You’re working hard, they’re investing in getting you up to speed, but the output isn’t there yet.
You have to build up all the context, figure out how the business really works, and develop the deep relationships and trust that you need to actually get things done.
You might break even after a year. But it’s only in years three, four, five, and beyond that you can get to the top of the curve, and things start to really work.
You can’t replicate this by stringing together shorter stints at companies. It’s fine to have one or two of them; sometimes things just don’t work out. But when job hopping becomes a pattern, it’s career poison. It feels like progress to switch and get a 10% raise and maybe a bigger title. But eventually this approach stalls out, because anyone hiring for senior roles is looking for examples of real tenure and real impact. If you’ve never done that before, why would you do that now, for their company?
Instead of jumping, you have an opportunity to throw yourself into this job. Focus on learning, being useful, making cool things, and building deep relationships with your colleagues.
You’ll soon find that you’re able to really get things done. Your impact will kick in, leadership will notice, and all of a sudden you’ll start to get the kinds of opportunities you really want, without even having to look for them. You’ll get more responsibility, bigger scope, and even more ways to compound your time at the company.
As you get closer to the top of the curve, you may also find that you’re earning more balance for yourself.
My personal example: the first time I had to cut back on the hours I was working was right after we had our second kid. I knew it was the right thing to do, but it still felt strange to me, and I brought it to my coach. His response was: “Are you actually producing less for the company, or is it possible that because you’ve been there for so long, you’ve figured out how to be just as effective in less time?” And it turned out he was right. I got promoted just a few months later.
So if you’re thinking about leaving to go find something better, consider that everything you want — learning, impact, great opportunities, even work-life balance — is actually right in front of you. You just have to let the power of compounding do its magic.
You should stay, because passion is built, not found
The top of the J-curve is not only where you get better at your job. It may also be where you learn to love it.
In the 70s and 80s, we started teaching kids to follow their passion. The idea is that the thing that will make you happy is out there waiting for you, and all you have to do is go find it.
This is terrible advice, because the world doesn’t work like that.
When I read So Good They Can’t Ignore You in my 20s, it shaped my view on careers more than almost any other book. The core thesis is that passion is not something you inherently have, but something you build over many years of working at it. From the book:
If you want to love what you do, abandon the passion mindset (“what can the world offer me?”) and instead adopt the craftsman mindset (“what can I offer the world?”)
Focusing on passion is selfish: you want the world to give you something that will make you happy.
The craftsman mindset is how it really works. You work hard at something, you start to get good at it, and you’re able to provide more value. Then the world rewards you for it in the form of money and status and increasingly interesting opportunities. This turns into a feedback loop, because it gets easier and easier to translate your work into greater mastery, impact, and reward.
I took my first startup job at Thumbtack (a marketplace for local services) because the team seemed smart and the company was growing fast. That was about it. What I came to discover over multiple years was that I loved the marketplace business model and all its complexity and second-order implications. It was like managing a miniature economy. Since then, I’ve doubled and tripled down on marketplaces, and have become more and more passionate about them.
Is there anything inherent in marketplaces that makes me a better fit for them than the next person? Definitely not. I’ve just worked on them for over a decade.
I’ve talked to so many people on my teams throughout the years who are full of anxiety because they haven’t found “their thing” yet in their career. I always tell them the same thing: no one has, because it’s not something you find. It’s something you build, over many years of focus.
So if you’re thinking about leaving to go find your calling, consider that it could already be right in front of you, if you’re willing to work at it.
OK, enough convincing you to stay. Now let’s change gears into why you should leave.