When should you give up?

how to know when to quit, and when to keep pushing...

One of the hardest problems we’ll ever face is deciding when to give up.

In a culture that prizes doggedness and grit, giving up looks an awful lot like quitting, and quitting is just one Thanksgiving dinner away from failure. It takes courage to stop, to pull the breaks, and to admit that you’ve made a mistake.

So where’s that line? When is it acceptable to give up, and move on?

Give up when you’ve changed

10 years ago, I’d never left the country.

I was living in Florida, starting my second semester of community college, and working at Starbucks for $7.50 an hour. I was studying fine arts, and spending hundreds of hours sketching bowls of fruit with a charcoal pencil.

Now I live on the west coast, and I’ve traveled to dozens of countries outside of the U.S. My average day consists of mostly reading and writing. I started a company, and make most of my money sending out emails and hosting parties.

I changed a lot in the past decade. I bet you have too.

And yet, we hold onto the 18, 25, or 39-year-old version of ourselves years after they’ve come and gone. For whatever reason, we feel that we need to honor the whims of our younger selves. That we need to see that original vision through.

You decided when you were 18 that you wanted to be a lawyer; now 12 years later, you’re rueing that decision. Wishing there was a way out of the grave you dug yourself over a decade ago. There is—give up. Move on.

You don’t have to be a slave to a version of yourself that no longer exists.

Give up when you’re all alone

After a long day of hammering away at the keyboard, you look up. The lights are off, the curtains are drawn, the room is quiet. You are, like you have been all day, alone.

We’re often told that the path of true innovation is a lonely one. That people won’t understand what you’re working on. That you’ll probably be the butt of a few jokes. And while that all may be true, that’s not the type of isolation we’re talking about.

The greatest innovators, entrepreneurs, writers, thinkers, creators, and builders have all been surrounded by people. Surrounded by support, by friends, by family, by husbands and wives.

If somewhere along the line you made choices that isolated you from these people, it’s time to give up. There is no crueler fate than getting to the finish-line, and having no one you love there to congratulate you.

Give up when you don’t feel safe

You’re dreading this next meeting because you know Stephen is in it. Stephen is always at your throat. He’s always waiting for you to slip up, to make a mistake, to get sloppy. Whenever he’s around, it’s time to put your guard up.

Hold back, hide your ideas, protect your reputation, defend yourself.

Or maybe you don’t have a Stephen. Maybe instead your demon is walking around the neighborhood at 10 at night. Or being the only Iranian person in your town, or the only female at your work.

If you feel isolated, or alone, or attacked, or like an outcast—it’s time to give up. If you’re the only person in your city interested in quantum computing, or the only person around from Cuba—it’s time to give up. If you feel like you can’t safely walk around at night, or that your colleagues are actively trying to bring you down—it’s time to give up.

The world is big, and that means there’s a place—somewhere in it—where you’ll feel an undeniable sense of belonging. A place where people understand you, where people will protect you, where you’ll feel safe.

There is no personal or professional progress, that can be made in an environment where you feel like no one has your back.

Give up when you start praying for things to go wrong

Fingers crossed the boss isn’t in the office today!

The client is three minutes late to our Zoom meeting, hopefully they forgot, and I can leave early!

I hope the office floods in the storm tonight, then I can work from home next Monday!

Wishing for time away from your work, your family, your passion, or your city is the clearest sign that your body is just going through the motions.

Your mind has already given up. It’s time to stop; you’ll be thankful you did.

Give up before you have to give up

In the past year, I’ve suffered three sports-related injuries.

Each one was serious enough to warrant at least a week of mandatory recovery. That meant no activity. No running, lifting, or hiking. Even after that, weeks, and sometimes months, of rehabilitation ensued.

It was up to my body when I would heal, and how long it would take. I was reduced to nothing more than a passenger in my own body.

But each injury could have been avoided. I could have simply pulled my training back before my body gave out. If I had the guts to stop, I could have consciously chosen when, and for how long. Instead I was at the whims of a recovery schedule.

If you’re feeling tired, or lonely, or unsafe, stop. Reflect. Ask yourself: is it better to retire gracefully, or to be carted off of the field on a stretcher?

Don’t give up when you stop seeing progress

When I was in 3rd grade, Mrs. Gold brought a monarch caterpillar into our classroom. We huddled up next to his little plastic tank, watching him inch around.

For the next two weeks, our little worm didn’t do much of anything except eat leaves and inch. Then one day, our friend had climbed his way up to the top of his enclosure, spun himself a sleeping bag, and became a real life Metapod.

For two more weeks, I was under the impression that he was just napping. That’s because I was 9. I wasn’t yet familiar with metamorphosis, and had no concept of silent transformation.

It wasn’t until I was much older that I realized caterpillars aren’t the only ones who can pull off this little trick.

Plants grow down, before they grow up. Water remains motionless until it hits 212°F. Teenage growth happens in—spurts. Just because you can’t see the momentum building, doesn’t mean it’s not there.

If you give up too soon, all the latent potential you’ve been building will never come to fruition. Hold out a bit longer, even if the momentum has slowed.

Don’t give up because it feels like the right thing to do

Our bodies lie.

They tell us we’re still hungry, even after a big meal. They tell us we’re too tired to go to the gym. They tell us we’re grumpy, or sleepy, or nervous, and they do so at very questionable times.

Our bodies lie because it’s their job to lie. It’s their job to use whatever tricks necessary to get us to do just two things: slurp up as much energy as possible, and hoard it.

So trusting our gut is the surest way to do less then necessary. Our body wants to take the easy way out. It’s predisposed to giving up now, and saving energy for later.

The irony of it all is that our bodies are apex predators. They’re capable of running, jumping, fighting, swimming. They can go days without food or water or sleep. They can derive calculus from scratch, build pyramids, and write the Magna Carta.

But your body doesn’t want you to know this. It doesn’t want you to realize how badass you really are. So it tells you that you’re tired, or sluggish, or sleepy.

Be skeptical of your gut feelings. Probe a bit further.

Don’t give up when something better comes along

San Francisco has been failing to teach people the same lesson for 175 years.

Starting with the Gold Rush of 1848, folks from all over the world have been drawn in, like flies to a bug zapper. The promise of a better life, and the chance to ride a once-in-a-lifetime wave, has enchanted ambitious professionals for generations.

But there are two funny things about the Gold Rush that most people don’t know. The first is that none of the richest people in the country at the time made their money digging for gold. The second is that none of those rich people sold pick axes either.

So how did they make their money? The richest people in the U.S. before, during, and after the Gold Rush made their money in: oil, railroads, steel, banking, publishing, and real estate.

All boring and mature industries.

Riches were never found by discarding the old for the new—not even during a literal gold rush. Don’t give up on something that’s good enough, even if something “better” comes along to tempt you.

Don’t give up even if you’re lost, and can’t see a way forward.

Your problems are not unique.

Just about any conceivable obstacle you could be facing, any hurt, or slight, or complication, has been dealt with by someone else. The rise—and resurgence—of Stoic Philosophy in modern times is a testament to this.

How can journal entries written 2,000 years ago still ring true today? They can because of one uncomfortable truth: while technology may change, we don’t.

Knowing this should give you some level of solace. It means that there’s a well worn path for you to travel. There’s someone you can learn from, a video you can watch, and article you can read, a conversation you can have.

Your route, out of your own personal darkness, exists. You simply need to find your guide.

Read widely, spark conversations, listen to those who have come before.

Don’t give up if you’ve only failed specifically.

If you’ve been having trouble dating, or raising money from investors, or getting a new job, odds are you’re failing specifically.

You’ve gone on a dozen dates, and none of them panned out. Well, are you sourcing all your dates from Tinder, Hinge, and Bumble? How many dates have you gone on that were initiated by friends? How often do you go to singles events? How many different towns, cities or states have you dated in? Ever asked someone out at the gym?

For most of us, we don’t have a dating problem, we have a specificity problem. Until we’ve exhausted all of the other options on our menu, we can’t come to any other conclusion beyond “dating apps are not leading to fruitful relationships for me.”

The same goes for finding someone to invest in your company. You came to San Francisco to raise some money, but so did everyone else. Have you tried raising money from friends and coworkers? Have you tried pitching family offices instead of venture capital firms? Have you tried getting (dare I say it) a small business loan from a bank?

So you could be having a hard time raising money. Or, maybe you’re just having a hard time raising venture capital in San Francisco this quarter.

If you’re failing specifically, don’t give up. There are still hundreds of other options for you to try.


PS. If you’ve made it all the way down here and don’t feel that you’ve just wasted five minutes, consider sharing this post with just one friend.

It helps others find it. And it makes me happy.

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