You Need to Try 100 Times to Find One Winner


Most people can endure anything. It’s all a matter of where you set your expectations. Everyone can become a master of something but very few are willing to try 100 times to find the work, passion, or person they can fall in love with.

If you’re a creative, an entrepreneur, or in sales, you must either learn this lesson or quit now.

There is no muse. If there is a muse, she does 1% of the work and you do 99%. And the work you do is ugly.

When someone says “I’m not creative” or “that’s great, I could never code” what they’re really saying is more about their mindset than their actual ability.

No baby is born knowing how to code. No baby knows three languages.

Sure, there may be some predisposition towards certain skillsets. But the most common differentiator is one person decided to slog through all the boring, bad, and ineffectual work to get to the good stuff.

Learning to Code

A couple of years ago, I did a coding “boot camp” where you learn how to become a junior full stack developer in a matter of 14 weeks. It cost me around $14,000, which is a lot, but I considered it a worthwhile investment. I was making around $45,000 at the job before that, so as long as my next job made at least $59,000 dollars, it would be worth it (and it was).

On the first day of class, I was sitting on the fence about whether or not I would actually like coding. However, it was much too late to go back on my decision.

I decided then and there that, no matter what, even if I hated it, I would commit to crushing this course. I was all-in.

Then something weird happened. I started to really like coding. Maybe I gave myself some Stockholm Syndrome for it. Didn’t matter. It worked.

I didn’t worry about anything else—dating, seeing the cool parts of my new city (besides networking events), what was happening in the news, or anything else. All I did was go to church on Sunday and hang out with my sister and brother-in-law, who I was living with. That’s about it. I came out the other end very confident, not that I knew everything about code, but that I could learn anything.

Lesson one: committing to something beyond how you feel about it day-to-day may mean you actually enjoy it more.

Job Search

During that 14-week course, someone from the previous 14-week cohort came in to talk to us.

He said one of the most helpful pieces of advice I ever heard. “I applied to 100 jobs before I got an offer.” He wasn’t giving advice, just relaying his experience—but it set my expectation. Apply to 100 jobs = get an offer.

Others in the room gasped at the number. I think they didn’t expect it to be so hard. I had no previous expectations, so this new one came in fresh and without judgment.

I kept a spreadsheet of every job I applied to. 138 applications later, I accepted a job. The job was from application number 93. The advice was nearly spot-on.

Side note: in the coding and software development world, the hardest job to get is your first one. It’s a big room, but a small door. Once you get in and get a couple of years of experience under your belt, you’ll have recruiters coming to you instead of always having to hustle for jobs.

Lesson two: set accurate expectations, even if they’re seemingly incredibly high so that the weight of the process doesn’t crush you along the way.

Creative Work

I heard the singer-songwriter Sia on the Tim Ferriss podcast. She was a successful songwriter long before she ever got famous herself.

Sia, credit Scott Murry 2016 via Flickr

She described the creative process as having to get all the crap out of the pipe first before the good stuff can come out. She mentioned Ed Sheeran is one of the best at this—he puts out tons of hits because he is so comfortable getting all the sludge out of the pipes before getting to the good stuff.

What does that actually mean? You write 100 bars for a new song and the first 90 are terrible. The first 50 are god-awful. The last three may actually have something to them.

A 3% success rate. I’m guessing that’s why most people don’t make it in creative fields. They don’t have the stamina or the shamelessness to just keep plugging along.

RELATED: 6 Passive Income Ideas for Creatives

What Little Kids Know (that Adults Forget)

This is why little kids are always trying something new and creative: they don’t know they’re bad at it yet. As kids get older, and they learn they’re not as talented as they thought, or as talented as the kid next to them, they stop trying. They find their niche. That’s not wrong, but if you bring that mindset into a new skill, especially a creative one, you won’t make it.

I love Kanye. He represents an ideal. His shamelessness has gotten him into and out of trouble so many times, he’s more like the embodiment of a zeitgeist. He might be the most American of Americans.

His shamelessness has given him a reputation. “Love yourself like Kanye loves Kanye.” It’s also made him look like a fool for tweeting at Mark Zuckerberg to invest in his shoe line. And only a few years later that shoe line has made Kanye a billionaire.

Lesson three: you don’t need to strike gold every time. You just need the endurance (or the shamelessness) to keep at it.


“Some people work 10 years to become an overnight success.”

Twitch, Clubhouse, Tesla, and many more. The founders slaved away for years in obscurity and failure until one day they had billion-dollar brands. If you haven’t heard of the first two, go look them up.

Paul Graham suggested the cutoff in investors’ heads for an entrepreneur might be 32. It’s not trying to be “age-ist” on purpose. Candidly, if you haven’t taken your leap by then, it is very likely that you never will. You’re probably just not someone who thinks laterally. Or at least you don’t act on it. 

You can always find exceptions (Ray Kroc, Colonel Sanders) but let’s get real. If your 60-year-old friend came to you with a big startup idea, and they’d never succeeded at any startup before, how likely are you to invest in them?

This isn’t to say you can’t be creative and bold if you’re older, but if you really are a creative and bold thinker, why haven’t you already taken action?

It’s usually young people who do startups for a couple of reasons:

  1. Young people are expected to make mistakes, make career changes, and act rashly. They have a built in excuse. 
  2. They have some work and industry exposure, but not enough so their thinking is firmly entrenched. They’re still curious.

Lesson four: don’t wait for “experience” or you’ll never start.

Don’t Wait to Get Started

If you’re young, stop wasting your time. It’s your greatest resource, which means it can provide you the greatest returns if you know how to steward it. Most people don’t.

You have time, so use it. The longer you wait to start, the longer you’ll wait to get to your winner. Remember, only 1–3% are actually decent.

Be shameless. The sooner you start embarrassing yourself, the sooner you’ll actually win. The shameless win, not necessarily the smartest.

If you’re smart AND shameless, and you’re not already in politics, then you have what it takes to be an entrepreneur, a VP of sales, a creative artist, or something way cooler that I haven’t thought of. Don’t wait. Start. 


Leave a Reply