Should You Leave Your Own Company Now?

It’s said that the two best days in a boat owner’s life are the day they buy the boat and the day they sell it. That might also be true for owning your own business.

If you’re a serial entrepreneur, it’s part of your makeup to buy and sell, the same way a day trader buys and sells stocks. 

You’re not in it past a certain point. 

Maybe you enjoy the conceptual ideation, creating, teams, and determining product-market fit, but after that, you get bored. Scaling and managing is not your thing. 

For you, selling your business is just a matter of time, and you do it willingly and expectedly.

Or maybe you started a business and you feel you’ve done all you care to do and are ready to do something else… or nothing at all. 

You might ask yourself the question, “How do I not get bored?” So you rethink your desire to sell and stay put.

Whatever the case, there is likely going to be a time in your business trajectory when you will want to step away from the company you founded or find yourself leading. 

So how do you make that decision with no regrets? It’s something I had to do and, looking back, I think I have some solid advice that worked well for me.

Here are four questions you can ask yourself to help make that difficult decision.

1. Have you accomplished all you wanted? And if not, how much longer will it take?

Naval Ravikant has a great saying: “The reason to win the game is so that you can be free of it.”

Did you play the game to be free of it? Do you still want to be part of the game? Do you think, deep in your heart, that you beat the game?

What will it take for you to feel free of the game? Once you feel free, it’s time to go.

2. Do you have a successor that can continue your legacy?

A big part of not letting go is the fear that your successor will ruin your legacy. Maybe they’ll run it into the ground. Maybe they’ll go a different direction you aren’t comfortable being associated with.

After my company was acquired by Home Depot, I had confidence that the leadership team would continue the legacy.

But that’s not always the case.

Look at Michael Dell. In 2004, Dell stepped down as Chief Executive Officer of Dell Inc. while continuing to serve as Chairman of the Board. He built the company from his University of Texas dorm room. 

But, the vacation didn’t last long! 

In 2007, he ended up coming back as CEO per the request of his board. And he came back with a vengeance. In 2015, Dell acquired EMC Corporation for $67 billion, which is one of the highest-valued tech acquisitions in history. 

If he had a successor that could continue his legacy, would he have come back? I’m not sure. And to make it even more interesting, it was his own board that asked him to come back!

3. Will your culture remain after you leave?

Are the values you believe crucial to your company’s long-term success when you are no longer there embedded into the culture?

Spoiler alert: If you ask yourself this question right before you’re thinking of leaving, it’s too late. Similar to asking yourself if you’ve done your job as a parent right before your child is going off to college.

Start your culture on day one! Not during your transition period.

4. Are you comfortable with what’s next?

What’s your next gig? In my case, it was teaching entrepreneurship in a business school and joining other company boards. So I started doing that before I left. This gave me confidence to leave. And my wife the comfort that I’d not be at home moping around, gumming up things there.

Let me be the first to congratulate you on a job well done. If you’ve made it this far in this article, it means you’re seriously considering what’s next.

Ask yourself these four questions, and I promise it will all work out.

The opinions expressed here by columnists are their own, not those of

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