As you may have noticed, I’ve been on a bit of entrepreneurial kick lately. It started around nine months ago, when I talked about the lessons that I learned from my biggest investing mistake. It was there that I wrote about the saying that had really resonated with me and which was starting to change how I looked at things:

“Don’t worry about failure; you only have to be right once.”

Coincidentally or not, around the same time I started coming across a lot of articles with the same theme:

It’s not what you do and mess up, it’s what you don’t do that will plague you when you are old and looking back on your life.

So says Amazon and Blue Origin boss Jeff Bezos.

“When you think about the things that you will regret when you’re 80, they’re almost always the things that you did not do. They’re acts of omission. Very rarely are you going to regret something that you did that failed and didn’t work or whatever,” says Bezos

– Jeff Bezos: This is what you are going to regret at 80 by Catherine Clifford

Over and over again I kept seeing the same message that basically boiled down to: “Don’t fear failure, because you’ll regret not trying more than you’ll regret having failed”. It was almost as if the universe was sending me a message.

Seeking Failure

I was inspired, and since then have been brainstorming what kind of ideas I could try failing at (see my article on Million Dollar Ideas). Additionally, I’ve been reading a lot about some of the most successful people of our time and some of their unique paths to success. I was amazed by how many of them faced significant setbacks early in their lives. Not all of them experienced instant success by dropping out of school and starting businesses that took the world by storm like Bill Gates, Mark Zuckerberg or Elon Musk.

Sir Richard Branson, the founder of the Virgin Group, dropped out of school. Mark Cuban, owner of the Dallas Mavericks, was fired from one of his first jobs. Howard Schultz, the former CEO of Starbucks who helped turn it into the behemoth that it is today, lived a true rags to riches story. John Paul DeJoria, the co-founder of John Paul Mitchell Systems and Patrón Spirits was previously homeless. Mike Lindell, the inventor of MyPillow was a cocaine addict who had lost his home and whose marriage had fallen apart. Steve Allan, the CEO of MediaCom, received 82 rejection letters before he even landed his first job. Even Steve Jobs, one of the most successful and widely respected entrepreneurs of our time, had gotten fired from Apple, the company that he had co-founded. It seemed like no matter where I turned, I was reading a story about massive early setbacks or unlikely successful comebacks. It was hard not to compare those stories with my own life and my own failures. Those personal setbacks that seemed so massive to me looked minuscule when compared to what some of these people had overcome. If they could scale those mountainous challenges that were placed before them, then I could certainly step over a few anthills.

Board Games

My first attempt drew upon one of my favorite hobbies: Board Games. I figured I’ve played enough games to be familiar with a wide range of game mechanics and to have a good grasp of what works and what doesn’t. I had even played around with designing games back when I was a child and through high school. The investment required early on seemed pretty minimal, as the only things I really needed were index cards, poster board, scrap paper and some colored pens. Lastly, I figured I had a large group of game loving friends who I could con into helping me to play-test my game.

After a few months working on designing 2-3 games off and on, I thought I had made some good progress. One, a simple card game that I liked to describe as a cross between Codenames and Taboo, essentially was finished after a positive reception to play-testing and just needed another couple hundred cards created (which I think would’ve been easier than it sounds). Another was mostly finished, but had stalled out a bit due to concerns with the main game mechanic. The most ambitious one, and the one I was most excited about, was still halfway through development and undergoing major design changes. Nonetheless, I thought it might make sense to start looking at what prototyping services might be available so that future play-testing groups didn’t have to put up with hand-written index cards and poster boards with sloppily drawn boxes on it.

That’s when a cold splash of reality was thrown in my face.

Every link I followed, every forum I visited, and every thread that I read was full of caution, warning, and naysayers. For every piece of advice that was imparted, it was constantly followed by a drumbeat of pessimism. Everybody was eager to point out how hard it is to break into the gaming industry or how much work it is to design a successful game or how little money there was to be made.

I don’t think I was naive. I had realized when I started designing my games that it would be a lot of work and the chance of actually breaking into the industry would be slim. I had no delusions that anything I created would turn into an Exploding Kittens type of success. None of this feedback was news to me. And yet, it was hard reading post after post and comment after comment from people who were essentially imploring others to second guess what they were trying to do and discouraging them from even trying. It was the polar opposite of the inspirational optimism that had encouraged me to start my attempt to seek out failure.

Maybe not coincidentally, I put my attempts to design a board game on hold shortly after this.

Other Endeavors

I was a little discouraged, but still determined to find something to plow ahead with. Next up on my list was the board game cafe that I had always dreamt of opening. I spent many hours on my commute to and from work brainstorming various business models and ways to make a potential board game cafe stand out and, more importantly, increase its profitability. I read about the successful Snakes and Lattes cafe in Toronto and watched some of their Youtube Videos on how to start your own cafe. I researched similar stores that were nearby to view the potential competition and to see what they were doing. I looked into potential locations and ran some numbers in my head regarding what kind of business I would have to attract in order to justify any potential rent.

In short, I sank a lot of time into it.

Yet once again, I ran into waves of negativity and pessimism when I sought out online forums for advice. Over and over again I read about how opening a gaming store meant working incredibly long hours for very little pay…. and that was if you were lucky enough to avoid bankruptcy. I’m not at all opposed to hard work, but it was clear by their tone that these warnings were meant to dissuade people. Once again, I found myself wavering and decided to look elsewhere.

I won’t bore you with more stories. Suffice it to say, they all end in very similar ways.

Self Selecting Success?

I was frustrated and confused. Obviously I didn’t expect things to be easy and I thought I was prepared for obstacles. However, I found myself getting thrown for a loop by the conflicting messages I felt like I was receiving. On the one hand, I kept reading about how the only way to find success is to put yourself out there and try and to be willing to fail. At the same time, I wanted to be smart with my approach and not take any stupid chances and to learn from those who had gone before me.

Honestly, I was mostly frustrated with myself, though. I thought I had mentally prepared myself to take chances and seek out failure, but it turned out that as soon as I met the smallest of obstacles, I reverted back to my risk-averse self. All it took for my motivation to crumble was a few cautious words from some online forums. If that was all it took to cause me to completely give up, how would I be able to face real adversity?

I started seeing things all over that seemed to directly speak to my dilemma. There was an old re-run of The Big Bang Theory where Penny quit her job as a waitress to focus full time on her dream of becoming an actress. Leonard freaks out over the irresponsibility of it, but Sheldon has the opposite reaction, pointing out that it’s helpful to avoid distractions when working towards one’s goals. When Penny asks Sheldon why Leonard doesn’t understand, Sheldon replies: “Because he is not like us, Penny. We’re dreamers.” Eventually, Leonard admits that he actually respects Penny’s decision because in taking such a big risk, she is doing something that he could never do. It’s hard not to see how that relates to how I was feeling. I even had what seemed to be a particularly relevant message from a fortune cookie that felt like it was directly mocking me: “Great men live dangerously, small men don’t take chances.”

I’m wondering if there is some survivorship bias that leads to a degree of self selecting success. The people who keep trying and failing until they succeed go on to be admired and talk about how the key to success is to keep trying and not letting failure dissuade you. The ones who give up before succeeding become embittered and hang out in online forums with cautionary tales to anybody who will listen. There’s a famous saying that Henry Ford might’ve said, “Whether you think you can or think you can’t, you’re right.” Maybe he (or whoever did say it) was right.

To me, this raises an interesting chicken or the egg question: Is there something inherent about people that makes them more (or less) likely to survive round after round of failure and eventually experience success? Or is there no practical inherent difference between people and it’s solely up to how persistent people are? There’s some evidence to suggest it might be the former.

People have one of two mindsets: scarcity thinking and world-class thinking, Siebold explains.

Too many people operate “through fear and scarcity,” says Siebold.

But successful people don’t think that way, he says.

“The world-class operates through more of a love and abundance mentality, so they’re seeing the opportunities,” Siebold explains to CNBC Make It.

“They’re looking for the opportunities, they believe they can succeed in the opportunities, where the rest of us are sort of in that fear and scarcity mindset and we’re trying to survive.”

– Self-made millionaire: This is the biggest difference between successful and unsuccessful people by Sarah Berger

I definitely feel like I’m somebody who operates through fear and scarcity. No matter how hard I try, when I start brainstorming ideas all I can think of is how difficult it would be to implement and what can go wrong. Fear definitely dominates how I think about possible new endeavors.

So where does that leave me? Pretty much back at square one. I’m a little more frustrated than when I started, and while I am a little more deterred, I’m still determined. I apparently just need a little more (maybe a lot more) “world-class thinking”. Anybody have some to spare?