Dealing with fear as an entrepreneur

The common thread between philosophy, therapy, religion is how to avoid self-sabotage. When are we most prone to self-sabotage? It's when we are afraid. Within the entrepreneurial route, there's so much fear involved in it. 

Anyone can get excited about something for 90 days. But that initial enthusiasm or the contrast to that shitty job you had wears off by day 91. Then, it's just the reality of “oh shit, I have to grow a business”. Psychologically, it can feel like life or death. That is the heaviest part of starting something. 

Within that abstract realm. Rom Doss says, “the great way is easy for, for the one who has no preferences”. The great way is easy for the one who has no preference. 

The great way, the great challenge, the great path is easy for the one that has no preferences– for the one that can find the good in any result.

Rethinking the result of failure 

How can you get off of this fork in the road of success and failure and get on to a single path that is going to take you to providence no matter what? Meaning is your ego tied to some result with your business or is your ego tied to learning as much as possible?

A guy was asked by Socrates whether he should get married and not. Socrates said:

“By all means marry. If you get a good wife, you’ll be happy. If you get a bad one, you’ll become a philosopher.”

He’s basically saying you could win either way. It's the same with starting a startup. Make the leap and start your company head on. Go into the unknown because either the company will do well and you'll be happy or there'll be struggles but you certainly will learn so much more.

Comfort with all outcomes

By starting your own business, you will have the learnings that are going to inform so many facets of your life. I built a business for five and a half years and it failed. I look back and say that was a 25 year career in five years. It's led to every insight I've had since then. It has allowed me to invest in startups, build further startups, informing the businesses that I built within Airbnb. 

It's shifted perspective on my life; it’s informed me how to orient your ego. I oriented my ego on accomplishment and I’ve since learned that if it's oriented on learning, then you can not lose. 

If you are comfortable with both outcomes: (a) the businesses are either successful or (b) you have a ten-year career condensed into a year and a half on something that does not pan out. George Bernard, a brilliant thinker, would say that he can get “comfortable in any scenario in life, as long as he can think through the worst case scenario and get comfortable with that”.

MBA versus Startups

The worst case scenario: you spend all your savings, some of your family and friends money, 150k, and a year and a half into your idea, and it does not pay out. 

A year and a half is less time than an MBA. 150K is less costly than an MBA. You're going to learn 10 times more than an MBA. Worst case scenario, you have a better education in less time for a cheaper amount of money than going to get an MBA.

And that's the worst case scenario! Best case you build something you're really happy with, proud of and eight months in 18 months in, you look back and you say “I'm so glad that I took both feet off the ledge and went after this”.

Bottom line

That fear is what we think is this potential at every turn that something goes wrong. The prison that I have often lived in is “what will people think if it doesn't achieve some result”, if it doesn't go the way that I wanted to go. 

That is a prison of my own mind. It's the wrong question. The question is more like, “what will you think if you don't take this chance 10 years from now, 20 years from now, 50 years from now?”

When you do that, not only does the fear evaporate, but a lot of these psychological constraints that we have start to ease up because we start to let go of this immensely specific preference that we have on how everything should work. 

When you start to let go of that then, you start to become a little bit more flexible and know that there's a whole range of potential results that are still net positive, even including the worst case scenario. 

Letting go is freedom. It’s freedom from sabotaging our own potential because we have this false constraint. This limiting grip on a very narrow set of outcomes because our ego is oriented around achievement instead of learning, which opens up really 360 degrees of potential outcomes that are still net positive.