3 min read

Permission to Fall

In life, I regret the things I didn’t do more than the missteps I made along the way.
– David Stanley

For the last three months, I traveled throughout South America. Despite what my Instagram photos may suggest, for the first month I was on the road, I was not enjoying it. Everything was new and stressful. There were no familiar places or friends to fall back on. The lack of regular schedules shot all my routines to hell. I felt lonely without my friends, and had no idea what I was doing. I drank too much, and exercised too little.

Searching, far from home

I had gone away to get out of the tech scene for a while, for a change of pace and scenery. I had recently left Chill, where I’d driven myself at a maniacal pace for almost three years. I needed time and space to think, refresh, and get some perspective.

But I was 6,121 miles away, and it wasn’t working.

On the night of December 21st, I remember calling Matt from my apartment in Buenos Aires. I’d talked myself in circles, about whether this crazy trip was still a good idea.

Should I just go back to California and take another job? Should I scrap the idea of trying to build something of my own? I was minutes away from booking a trip back to the USA so I could spend the holidays with friends and family.

Thankfully, Matt helped me see that I was just looking for familiarity. But why wasn’t I enjoying myself in Buenos Aires, a city full of steak, beautiful women, and dreams? At first, the answer seemed simple. I wasn’t committed to letting go of control and to seeing what the trip would bring me. I was holding back. I was also suffering from social isolation, and a bit too much time on my hands.

But that wasn’t the real reason. I know how to let go and accept what comes.


The real reason was simpler and deeper: I needed to give myself permission. Permission to feel new emotions. Permission to try on new experiences. Permission to fail.

At first, I dismissed this realization. There’s no way that it could be that simple. Of course I give myself permission to enjoy this. I got myself here, right?

But as the weeks wore on, the quiet reminder inside insisting that I give myself permission refused dismissal.

Whenever I shied away from embracing an experience or taking emotional risk—whether it be asking out a woman I liked, striking up a conversation in Spanish with a stranger, or allowing myself to truly enjoy a fun moment with new friends that I’d soon part ways from—the reminder never faltered: “Give yourself permission. Give yourself permission. Give yourself permission.”

Those words, the overriding theme of my trip, changed my perspective on risk.

Giving myself permission to embrace joy also meant that I needed to give myself permission to fall. To leave the constrained band of emotion which contains most of daily life, and to be susceptible to a full range of emotions. To accept the real possibility of failure and getting hurt, knowing I will find a way to get back up if that happens. Never before this had I thought, “it’s okay if I fail here.”

The falls make the jumps

Without the fall, there is no leap. Without the leap, there is no bridging the gaps between where we are and where we want to go. Without crossing these gaps, there is no progress, no growth. And without growth, there is death.

Thus, without the fall, there can be no life.

We each have opportunities to grow, and to do, and to be. The size of these opportunities is so great as to be scary. We all want to be successful in realizing our hopes and projects in the world. But we’re scared of falling.

I was afraid of the pain of falling down. The pain of failing at something I tried. Of people laughing at me. I still feel that. I think all creators do.

But, I’ve learned that the pain of regret, of not trying, of not going for it, of not kissing the girl or pitching the idea when the moment was ripe, is searing. And far worse, it lingers.

The only safety net is our own survival ability and the ability to pick ourselves back up.

It’s the falls that make the jumps.

Only one gatekeeper left.

And so, the real question:

Will I leap?



(Photo credit: Cultoftheshadow)