The Biggest Unforced Error is Leaving on Mediocre Terms

So a New Year is a time for reflection, and for many, it will be a time for change.  A new role, a new company, maybe even starting one yourself.

That time comes.  We all know it when it does.  I remember the first time I felt it.  In my first tech job, I was working at a firm helping startups … and then I knew one night, it was time.  It was time for me to join one.  I gave my notice the next day, with no job lined up, and zero savings.  I just knew.

But I did give 60 days notice.  That 60 days notice sounds long, but one of my bosses really needed it.  And it cost me.  I did end up joining a startup, and the strike price for my options doubled over those 60 days, costing me about $400,000.

Time has gone on, though.  And I worked with that boss several times thereafter, including as my investor.  It was worth it.

I’ve then left two jobs since.  In both cases, I actually gave 6 months notice again.  I thought that was more than enough, and it was.  But even there, looking back, I could have done more and better.  I could have left on better terms, even with the 6 months notice!  I should have.  I regret it, even now.

Fast forward to today, and as the years have gone by, I don’t so much see karma as I see re-runs.  What I mean is, I see successful folks again and again.  They start new companies.  They get promoted to VP of Sales.  They do new, interesting things.

And while we don’t, for the most part, work together 52 weeks a year, the ones I still work with, are the best relationships.  And they’ll all been worth investing that little bit of extra time at the end of one phase.

Here are 3 folks that worked together, back in the day.  One went on to be CRO at Brex, and then Partner at Founders Fund.  Another is now SVP at Gong:

Go long in your career.   I’ve yet to see this not pay off.  And the simplest hack to do that is just to leave on great terms.  It’s not that much extra work.

And you’ll see them all again.

Published on January 3, 2023

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