Giving Up and Other Blasphemies

Declaring failure is sometimes the right thing to do

What the worlds of tech and VC celebrate is grit, persistence, endurance, dedication — an entire thesaurus full of similar words.

I am here today to celebrate the virtues of just giving up.

A Diving Story

Many years ago, when I was young and broke and living in New York, a group of my friends decided to go scuba diving in Bali. At the time, this was an exceptionally adventurous thing to do and I was exceptionally stupid — this has not changed — so I said “yes” to joining the crew. It sounded awesome!

No visibility problems here…

One of my buddies and I needed to get certified. We did the initial procedures at a gym pool in Manhattan. For our open water test, we schlepped one morning to Far Rockaway, Queens. We put on our dive stuff and sidled into the water.

I had not quite realized I was claustrophobic until that moment. The visibility in that water was, and likely still is, approximately one inch. My eyes, ears, and brain all shut down instantly.

The success of my entire trip relied on my getting certified so I could, you know, go scuba diving in Bali. That didn’t matter. I got out of the water, took my gear off, and sat in the rented car waiting for my buddy to finish, which he did.

In other words, I gave up.

Giving Up

There are other similar stories in my personal life. The message is the same: at selective moments, I am perfectly capable of being shamelessly pusillanimous and, more importantly, being comfortable with it.

Over time, I have realized this acceptance of acquiescence, for that is what it is, as a rather large positive.

I now think of my ability to periodically give up as being, gulp, one of my superpowers.

Note: if I ever ask you what your superpower is, please strap a rocket to my posterior and shoot me to the Oort Cloud.

The Dark Side of Persistence

The point of this anecdote is not to suggest you, too, should avoid getting open-water certified in Far Rockaway, Queens. Well, yes, I support that decision too, but here I want to talk about some lessons for entrepreneurs.

Well, just one lesson: if you’re facing an obstacle that you can’t conquer, sometimes it really is best to give up.

There are many reasons for doing so, and here are four that come to mind immediately:

• You enter a post-fact zone. This one is particularly relevant if you are trying to convince someone (an investor, a team member, and so on) of something.

• The result may in fact be incredibly miserable. If the practice is nerve-frying, reflect on whether the main event is likely to be any different.

• You will make everyone else miserable. Especially if you are a leader and have people who follow your instructions, you’ll be helping all of them slam into a wall at high speed.

• You’ll keep doing the same stupid thing repeatedly. You’ve heard this before—“Insanity is doing the same thing over and over and expecting different results.”

As a founder or really anyone dealing with limited resources, success is optimizing the use of the resources you do have. Giving up on occasion can free up resources.

Foolish Fetishizations

I once wrote about the fetishization of entrepreneurship, which I view as one of the curses of our time. The fetishization of persistence can also be a curse.

The downside to persistence is that it can lead to repeating a very dumb action until something breaks.

Don’t do that.

And One More Thing

The Bali story had a happy ending. We all showed up in Bali, nobody checked any certifications, and our dive guide — an ex-con who had just got out of rehab and smoked weed all day long, and deserves a blog post of his own one day — took us below the waves.