Well, This Is Awkward

“You need to be comfortable being uncomfortable.”

I first heard this saying 20+ years ago, long before I started a company or family.

And I didn’t think much about it at the time. But looking back on it now, it’s absolutely accurate!

Anything worth doing starts with being uncomfortable. At least a little. Or maybe a lot.

It pushes us into the unknown nooks and crannies of our abilities and past beliefs. Into the places we haven’t been, but where we feel alive and curious.

And where new experiences turn into learnings, growth, and forward progress.

Not to mention confidence and a few good stories to tell.

Q & A

A few weeks ago, I was at Drexel University talking with entrepreneur students. I had a video crew following me around (as part of one of my so-called muses).

They’re editing the video now, but sent me this transcript from one of the questions a student asked.

Q: Since you had a very technical company and you mentioned it's important to show the customer personality, in addition to feedback on the website, was there anything else you did?

A: Yeah. So initially, because it was just me, it was a lot of the Jeff show, for better or worse. And I was not comfortable at all with doing anything. I wasn't comfortable with writing. I wasn't comfortable with email. I wasn't comfortable being on webcam. I wasn't comfortable with webinars. I wasn't comfortable with any of it. But I had to be.

It was like one of those hats you just have to wear in the beginning. You have to put them all on and figure it all out if you want to do this. You have to push yourself outside of where you're comfortable.

I mean look, these guys are following me around with cameras. I'm not comfortable with any of this. But I know that growth happens when you push yourself, and it's interesting to see what that turns into. So we're out having some great meetings and dinners with guys that might be able to help these guys out, and they might be able to help this guy out, and I'm just along for the ride and it's just fascinating.

So you just got to push yourself. So I push myself to be good at stuff.        

Hide and seek

I had really bad acne in high school. Like, the worst. My face hurt to smile.

As a result, I learned to love the dark and hate the light.

I didn’t want people to see me. I wanted to hide. And honestly, sometimes the introvert inside of me still does.

So having cameras follow me around for almost a week was, well, uncomfortable.

But that’s also why I did it.

And it’s also why I feel the pull to create and build. To try new things and learn what works (and what doesn’t). It’s partially to see if I can, but also to grow and satisfy my own curiosity.

And, most importantly, to feel alive and be the person I want to be (and I want my kids to see).

Which means I (still) need to be comfortable being uncomfortable.