I’m Tired of Running My Successful Start-up After X Years. What Should I Do?


The Holidays are coming up, or likely depending on when you are reading this post, at least some holiday is coming up soon — and I hope you are taking a vacation.  Even in these crazy times.  Some sort of break.

Because, I know you are tired.  Really tired.  SaaS is hard.  The New Revenue dials and dashboards in Salesforce go back to zero every month, or at least every quarter.  Everyone wants to grow even faster.  The team is a bit restless.  The customers are great but … they … are … so … tiring.  The travel.  The competition is everywhere.  The complaints.  The 1-on-1s.  The investors.  I know.

I know.  As the Holidays come, though, let me reach out if you’re feeling really burnt out.

“I’m Tired of Running My Successful Start-up After X Years.  What Should I Do?”

First, let’s be clear — everyone gets tired after about 4-5 years.  Really tired.  Everyone.  You are not alone.  You would be surprised how many of the Top 100 internet CEOs were exactly there.  And after 4-5 years if often when one CEO steps down, for another.

But if you’re Burnt.  Crispy Burnt.  My first suggestion is this:  take 2+2 weeks off.  It’s hard to take a full month off, so instead do this (or if you’re already going on vacation, flip it around):

  • For the first two weeks, come to the office, but don’t really work.  Go to the gym or for a run after you get in.  Decompress at the movies in the afternoon.  Just let yourself disengage a bit.
  • Then, then two weeks really off.  Go at least as far as Hawaii, maybe further.  Check email only once a day, and do nothing other than simple responses for mission critical items.  No phone calls, no work product.

Only then, consider your next options.

Bringing in an outside CEO might seem on the surface a good option — but I’m skeptical, because after X years … you probably would have already done this if it was the best option.  You would have done this earlier if it was the way to go — because that’s obvious.


So I think the more likely practical option, after the 2+2 weeks, is if you’re burnt out after X years — Redefine your Role for this and next year. 

Dedicate yourself to bringing in that missing VP, or a COO, someone to somehow shoulder at least 40-50% of your load.  Since you’ve stuck it out for 4-5 years or however long, I bet if you can find someone to take half the weight off your shoulders — you can still do amazing things at your company.  And economically, you probably should.  You have so much invested in these shares, this company, this journey.  SaaS is a 7-10 year journey — and you already have learned and accomplished so much.

>> Tired?  Burnt?  Then Bring in the Help next year.  Make that Job 1.  Put everything else aside.  Then it will be better.  Maybe even great.  I promise.

(note: an updated SaaStr classic post)


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