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What do you do after selling your company?


What should one do after selling a company? Besides growing out your Al Gore beard, of course.

So we sold the thing I've been working on for the past five years. Great!

But I'm not working on it anymore, so, what do I do now? This is a tough question to answer. I've tumbled this around my mind dryer for a while, and in the past few weeks have asked many people about it. I thought it might be interesting to take a stroll through my thoughts for anyone else who might find themselves in a similar life inflection point.

"Start something new," some have said.

You could. You could create another company. After creating one company the next will be easier, and, even if you don’t have ideas, you’ve been witness to tons of pain points around which you could design a new solution that can turn into a new company.

But you don't want to rush into the next thing. A new company needs fresh, hungry energy and you’re not there yet. You will be, but not right away.

For me, it seems the main driver of wanting to do something new comes from thinking, the best time to plant a tree is yesterday.

Yet you don’t want to let inertia run your life. The easiest thing to do is the thing you've always done. So you hold off on validating ideas for now.

"You should take this opportunity to travel," others will say.

If you enjoy leisure travel then, by all means, go for it.

Me, I’ve traveled plenty and I generally don't enjoy leisure travel anymore. I only see travel as being worth it if you have a good reason. Like visiting friends. Maybe one of them just sold a company of their own and you can drink ice tea on a porch in Georgia together. (State or country, your choice.)

If I wanted to be somewhere else, I’d find something to make it worth being there and dive in ass-first. I never thought I’d get to live in Montreal, but for the past five years I’ve had a great reason to be here and that’s enhanced the experience all the more.

Travel is just killing time. (Then again, you've got time to kill.)

"You could come work at our company," others will say.

It’ll be hard to get your head around working for others. After such intense work on a project of your own, working on someone else’s will feel strange. It could very well be the perfect way to reset, but it’s too soon to know if that's the right path unless you know what your next step is. And if you know then what are you doing here?

If you choose to work in an established organization, it will likely have to wait a bit if you want to give it your best. It will take time to mentally free yourself from the challenge you just finished. You don't finish a marathon and go to the gym later that day.

"Relax! Take some time for yourself," others will say, envious that you can relax.

You can take it easy for a while. Just chill.

Well, unfortunately the activity you used to find so relaxing was working on the company you just sold. Your "downtime" was happily devoted to it. All of your old hobbies and passions? Gone.

I've tried picking up some of my old hobbies and interests again in the past few weeks but they seem so … light.

You’ll find they’re a good way to keep busy, and sometimes even fun. You’d probably get used to them taking up a larger portion of your time, but they aren't the all-consuming engagement you got from building a company.

You didn’t start a company because you like to relax.

“Help other people,” some might say.

You’ve learned a lot and maybe you can pass some of it along. That seems actually worthwhile. A good use of time while you have the time to help.

I’ve been doing a little of this lately. I was a volunteer for Out Of Office Hours for the past few months and have had some great conversations with people just getting into tech. I've also spoken with a number of people starting their own companies, and offering any benefit they can take from my experience. I've also helped some people with their finances and their investments.

A lot of amazing people helped you out along the way, building and selling a company, so you should want to do the same. Pay it forward and all that. The tech startup world in particular is incredibly helpful and supportive of each other and that’s a tradition we should keep.


No one else will be able to tell you what’s right for you. But after 3 weeks, these are the two things I’ve found are most worth doing right after you sell your company:

  1. Take some time to decompress and ease your mind into a new phase. Don’t over-commit. Don’t make any major life choices. Find your centre. Do some exercise. Eat a donut.
  2. Have plenty of conversations. Talk to everyone you haven't had the chance to talk to because you’ve been so busy. Rebuild those relationships you had to take for granted. You never know what your best next step is, so surrounding yourself with different voices is a great way to open your mind. Not to mention that spending time with good people is good for the soul.

Me, I feel like I'm still rebooting. My work was so integrated with my life, that one without the other doesn’t quite make sense. My old habits are gone and I have to build all new ones. It's okay, I'm enjoying the challenge of not having a challenge.

In the meantime, if you have an idea of what I should do next, or if there's some way I can help, or if you just want to have a conversation about whatever, my calendar is more open than it's been in years.

Send me an email by clicking this link worded giraffe for no reason.