The Best at Starting Over

This past weekend was difficult. That’s… probably an understatement.

I woke up this past Saturday feeling crushed by the weight of the reality that I am, in no uncertain terms, starting everything over with my startup project and by the time I went to bed the roaring inside my brain had intensified to a high-pitched scream.

At one point I wanted to take a screwdriver to my brain. But, a short and pointed conversation with my best friend quickly brought me back to center (and out of my toolbox):

Starting over? You’re the best at that. That? Do that.

She’s not wrong.

Since making the decision to come out here to SF in early-2015 I’ve had to “restart” my “primary” professional life no less than 5 times, the first was simply relocating here from Atlanta (originally we thought we were headed to Austin!) and joining a recent graduate of the YCombinator program.

I tried being a senior leader in three companies and got fired from all three before the first 12 months had even closed. I then started a new co. as a negative reaction (i.e. in anger) which didn’t work out (***thank the lord) and then cofounded Pinpoint, raised $16.5M, then resigned to start my current project, YEN.

And, insane as it might sound, in the middle of all of those major professional “shifts” I was still actively building a number of indie projects, a few of which were actually winning industry awards while a few others were totally fucked. I also started vlogging and booted up a handful of net-new email newsletters (I have a new one, go figure) while maintaining my daily public writing (i.e. blogging) routine.

Crazy, right? And if you actually look at my current “active” projects, you’ll notice that most of them are dead and gone, which means that I had, at one point, started them.

As my wife pointed out, I’m “good” at starting over. In fact, it might be where I’m at my very best.