As a founder, you’ve learned to live with “churn” in your workforce. People come and go, and it’s your job to figure out how to carry on regardless.

What happens when you’re the one eyeing the exits, though? When you’re not quite sure if you’re up to the job anymore?

Serial entrepreneurs like Kris Duggan have seen countless colleagues work through this process. They’ve identified five questions any entrepreneur should ask themselves as they think more seriously about moving onto what’s next.

Do You Still Love Going to Work Every Day?

For many workers, the answer to this question is “of course not.” For them, a job is a paycheck, not a calling.

Founders are not “most workers,” however. You launched your company from a place of passion and continue to love working on it day in and day out, long into the evening.

Once that’s no longer the case, you may be ready to move on.

Is Your Team a Source of Strength or Frustration?

Your team should be a source of inspiration. Conversations with your colleagues should recharge your batteries and get you excited about their work. If, instead, you dread interacting with your team, or find yourself bogged down by the details of managing them in a way that’s not easy to overcome through delegation, you could be experiencing burnout.

Are You Still the Best Person for the Moment?

Answering this question honestly takes a big dose of humility, which doesn’t come naturally to many founders. 

One way to look at it is to step outside yourself and imagine how you’d evaluate your performance, capabilities and future-fit if you were your own boss. You’ve done this for who-knows-how-many employees over the years; now it’s time to do it for yourself.

You might not love what you learn. But you must be clear-eyed. If an honest assessment reveals that you’re not the best person to scale your company from 50 to 500 employees, or lead development of its next standout product, or enter a half-dozen international markets in the next two years, so be it. Time to step aside gracefully.

Are You Too Focused on Side Quests?

Feeling compelled to focus on “side quests” beyond your company’s operational core may be an early sign that you’re ready to move on. 

For example, while no one doubts Tesla and SpaceX CEO Elon Musk’s entrepreneurial chops or stamina, he has for years devoted considerable amounts of his time and effort to rabbit holes like the Boring Company (which has little to show for seven years of work) or X (formerly Twitter, which lost much of its value after he bought it in 2022).

Great leaders often make bets that don’t work out. However, when these bets distract them from their most important duties, it may be time to reevaluate their priorities.

Are You Making Uncharacteristic Mistakes?

Another sign that it may be time to move on is an increase in the number of preventable mistakes you make on the job. These may be difficult to recognize at first, but pay attention: If colleagues you trust begin to question your judgment, or you find yourself suffering more frequently from tunnel vision, something may have changed.

Know When to Go

We’ve all been in awkward social situations that drag on just a bit too long. Dealt with guests who overstay their welcome. Wondered, silently, when this wildly unproductive call or meeting would end.

It’s easy to recognize these situations when we’re not the cause of them. It’s more difficult to admit when we’re the problem. Who wants to do that?

Well, if you really care about the company you’ve built, it’s important that you do. Think of it as a parting gift that ensures your legacy as a founder lives on, and just maybe frees your time to begin your next great adventure.