The greatest tragedy in life is not trying.

‘Someday’ is the saddest word — it may as well mean never.

I know that failure isn’t a dirty word. In startup circles, I often get the feeling that it’s almost admired. We want to see failures, failures who have turned their shortcomings into a success down the line. That’s why we idolize entrepreneurs who have truly screwed up, only to find a way to become winners in the third act.

I think it’s apparent that failure itself isn’t a tragedy. When you fail at something, you don’t even need to feel too badly about it. There’s about a thousand quotes, platitudes and cliches about failure that you can fall back on to help you recover. Just search failure on Google and you’ll be bombarded with wonderful prompts and ideas to help you come back stronger than ever.

We’ve reached a point now where many of us are learning that failing, falling, crashing and burning are all a part of any journey to accomplishing anything. That’s good. I love it. I love that we’ve blown past some of the stigma around making mistakes. It’s just going to be OK.

Because the real obstacle that stops us from moving forward has nothing to do with failure. The real hurdle that takes out most entrepreneurs, dreamers, founders, writers, game changers, future basketball superstars, would-be musicians, painters, rappers, runners, programmers, visionaries and potential astronauts has never been failure. It’s not even bothering to get off the couch and try.


I meet tons of people, doing what I do. About 15–20% of them are building companies, or freelancing, or making money or achieving some level of success. Those people are incredibly inspiring to me, and they make my life so much more interesting because they have built some raw experience, that I can use to teach them, or learn from myself.

The other roughly 80% of people have written “start a business” or “write a book” on their to-do list and have never done it. It’s been on the list for so long, there’s almost zero chance they’ll get around to it. They are everyone. They are everyone because they just haven’t tried. They’ve decided that they’re going to change their lives, and they think that decision is enough.

I wish that was the case. I wish I could say that intent is 9/10ths of the battle, but that’s patently untrue. Intent is just raw material waiting for a catalyst. As long as you do not take action, you will not find that catalyst, and you will not achieve traction, and you will not become more than you are.

I believe that not trying, due to inertia or a perceived lack of time, energy or resources, or any other reason, has prevented the world from hearing music more beautiful than we could imagine or dream of.

I believe that there are hundreds of visionaries and geniuses, somewhere out there, who just didn’t try — and because of it, humanity missed out on companies, products, ideas, innovations and theories that could have changed the way we live and breathe. I believe that there are artists who could have created works of beauty so profound that they could bring politicians to tears — but they never tried.

I have intense FOMO when it comes to makers and builders. I don’t want them to succumb to the modern human instinct of laziness and lethargy, because if they do, I could miss out on the greatest companies and creations of all time. I’m selfish. I want nice things. So sue me.

We’ve accepted that failure provides us with lessons. As long as you’re living consciously and not running on autopilot with zero self awareness, that’s always going to be true. Inactivity, never trying, that doesn’t teach you anything. You don’t improve, you don’t advance, you don’t develop and you sure as $#it don’t win.

If the worst that could happen, by trying and failing, is that you learn some tough lessons, you have every reason to go for it. Sure, there are always other consequences that can be hard to face — I’ve lost money, lost clients, lost some self respect, lost my way and lost my relationships, due to starting and shutting down businesses and relationships — but you always get through them. You can always come out the other side.

I don’t think people believe me when I tell them that I want everyone who reads my posts to be bigger than me. I want them to be huge. I want every single person to be wildly successful, fulfilled artists, talented novelists or millionaire entrepreneurs. I can’t think of a better legacy to look back on. But it’s never going to happen if you don’t put on your game face and try.