How do you know when to leave a company?
"Should I stay or should I go?"
In turbulent times, it’s natural to think twice about the path we’re on. These days a lot of people are likely asking themselves “should I stay at my current job, or should I try something else?” The classic question: “Should I stay or should I go?”
Here are some questions to ask if you’re in that situation, drawing on my own personal experience, as well as what I’ve learned helping friends think through whether or not to leave their jobs.
In 2014, I joined Product Hunt as the first full-time employee besides Ryan Hoover, and around the same time as Andreas Klinger, working on community and business development. Although I’ve previously written about the asymmetric upside of being in startups and why starting a company is less risky than you think, it was actually joining a startup as an early hire that ended up giving me the most career capital.
At Product Hunt, I built my network at scale in a programmatic way: every day I was working with dozens of founders, helping them launch and get their first customers. I also began to build my angel track record, finding Lattice, Rappi, Scale, and others. More importantly, I learned a lot watching Ryan Hoover, who’s the best community-oriented product person I’ve come across. I had learned a lot building my previous startup, rapt.fm, but joining Product Hunt was where I finally had insight of what a startup looks like when it’s working.
Product Hunt was an incredible experience. Yet I ended up leaving in 2016. Here are four of the big reasons why I chose to move on:
My personal growth at the company felt stagnant.
I was getting traction with investing and I wanted to double down on that.
I wasn’t having as much fun anymore.
Was this the right decision? It’s hard to be certain about counterfactuals, but here are some of the things I probably missed out on by leaving too early:
Money. Product Hunt was sold to AngelList later that year, and people who stayed, naturally, vested and got more money. That money would have been meaningful to me at the time.
More respect from my teammates. If I had stayed during the harder times and through the acquisition, I would have earned the respect of leadership instead of bailing. My relationships would have been much stronger. I had also developed a reputation for going after shiny objects which was only magnified when I left. I was definitely scattered.
Company-building experience. I could have learned a lot by trying to rise up within the company, becoming more integrated with leadership, and seeing the company close up through all stages. I saw myself as “not learning” as much as I could have, but that was mostly on me. If I had worked harder to gain more trust and scope, I would have been able to learn a ton about how to navigate the highs and lows of a scaling startup. There were certainly people who stayed who’s learning only accelerated over time.
Stronger relationships. Relationships are forged through overcoming hardship together, not when everything is up and to the right all the time. Instead of focusing on why it wasn’t as fun as it used to be, which was because I and the company were going through growing pains, I should have asked how I could grow from the challenges and built stronger relationships with my teammates. For me, “fun” at a job comes from the ability to have autonomy, mastery, purpose—and the quality of relationships with my teammates.
Hindsight is 20/20, but if I could do it over again I would have stayed another 6-12 months. I would have made more money, built stronger relationships with my peers, and I would have learned a lot about company building by being there through the highs and lows and the happy ending with the acquisition.
What would I have missed during that year if I had stayed? This is also hard to say. I visited family in Colombia for a couple months, a bucket list item I wanted to do. I also explored a number of different startup ideas that didn’t work out. The On Deck dinner series, which I also began during that year, was a great source of deal flow, but I didn’t know how to make it a startup until a couple years later. My team and I announced the launch of Village Global almost two years after I left Product Hunt too. It was a long road. I feel confident I could have helped launch On Deck and Village Global if I’d stayed a bit longer at Product Hunt. Of course, it’s impossible for me to know for sure if I could have “timed it right”.
Regardless, one thing I’d stress is to make sure your references are strong before leaving a company. References are often binary – they’re either very positive, or they’re not. Lukewarm references are often viewed in the same bucket as negative ones. So why spend two years at a company only to leave with lukewarm references, either related to skill or attitude? In some ways, you’d almost be better off not having joined the company at all than getting a negative reference. One way to check this is simply to ask the people who will reference you what they’d say about you. They’re also likely worried about what you’ll say about them, so you can proactively let them know that you’re rooting for the company and will encourage people to work there. Another way I’d do it is to ask how you can leave but still set the company up for success. Letting them know well in advance and helping find a replacement are ways to leave with a strong reference. Even if you didn’t crush it, you’ll be known as a loyal team player, which matters a lot.
Anyway. Here are some questions I’d ask myself if I was considering leaving my company today:
Can I build career capital by staying better than I would otherwise?
Is the equity/cash upside meaningful? (Not critical, unless it is)
Can I build a track record investing or operating here?
Am I building my network?
How might this network be utilized in other future opportunities I want to do?
Am I exposed to opportunities that could help me get line of sight to the next thing?
Am I still learning from the people I’m working with? Are these people I’d want to work with in the future?
Is there opportunity to develop a strong reputation internally?
If I like the company but not the role, can I try to find a new one internally?
If I succeeded at my 3-6 month goals at this company, would I be proud of my outcomes?
Do I believe in the long-term prospects of the company, and my ability to influence them?
Even if the company didn’t work out, am I developing my career capital faster than I would otherwise (because of either network, reputation, investment track record, skills, etc?).
Am I leaving on good terms? How can I best set up the company for success If I do so? How can I leave with as strong a reference as possible?
What are my alternatives? If I decide to stay, can I pick a certain date (e.g. 6 months from now?) to revisit it so I’m not constantly revisiting the decision?
If you have any additive questions or frameworks, add them in the comments!
Thanks to Vikram Rajagopalan, Sachin Maini, Will Jarvis, and Gonz Sanchez for edits.