Entrepreneurship requires being weirdly optimistic

As of this writing, I’m the least unhappy with my work than I’ve been since the early days of my journey. Most of the time, when people ask me how I’m doing, I tell the truth and say, “ehh, not great.” I’m surprised I’m currently to this degree of not unhappy. Is “not unhappy” a valid emotion?

An interesting lesson that I’ve learned is that entrepreneurship requires being weirdly optimistic. Did you ever hear, maybe in an English or composition class, that the tree types of conflict in a plot are you against your adversaries, you against the world, and you against yourself? That’s the same thing with entrepreneurship, except it’s all three together, combined, at all times of the day.

Your haters and your competitors

Or, you against your adversaries.

You will definitely have haters. They’re annoying, but they’re inevitable.

You might even have competitors. Competition might be a good thing when it comes to market validation. But they’ll scare the shit out of you with their massive payrolls and their high-profile customers.

Your hard work ending in failure

Or, you against the world.

One recent revelation of mine was that failure can be a ton of work. You can work your ass off only to fail. That same amount of work might have led to success, but this time it didn’t, and you’re sitting alone at home not wanting to do anything because you just failed.

Failure is the default state for a startup. Failure will happen for you.

But Dillon, you say, why can’t you just pivot when you get a failure?

In the cases where the failure is a failed attempt to validate a market or product, sure, a pivot is probably the way to continue finding the correct answer. However, one doesn’t simply pivot.

One doesn't simply PIVOT

You just worked really hard on your current project. You had some great signs to make you think it would work. It made you excited. Then suddenly, it failed. You’re crushed. You’re defeated. You aren’t ready to pivot, not yet at least.

Your self-doubt

Or, you against yourself.

Taking the plunge is an interesting phenomenon. Suddenly, people treat you as if you’re smarter than you were before you took the plunge. Quitting your job to work full-time on a startup attempt signals a lot of self-confidence. I believe most people who try to start up are reasonably self-assured. I know I was.

Am I still self-assured? Depends on the day you ask. As I said earlier, today is the least unhappy day of work for me in recent memory. I feel pretty good today. Before today, I was probably much less down on myself.

Not losing enthusiasm

Success is going from failure to failure without losing your enthusiasm

Either Winston Churchill or Abraham Lincoln said that. It might sound corny, but that’s the only way to continue persevering and persisting your way to greatness.

The pessimist who hates all business ideas will be right most of the time. The optimist will be wrong most of the time. If you’re weirdly optimistic and maintain your enthusiasm failure after failure, setback after setback, you just might survive your wrong decisions and hit something big.

If you enjoyed this post or would like to give me any feedback at all, I'd love to hear from you! You can tweet me at @dillonforrest or email me at dillonforrest@gmail.com. It'd make me super happy to hear from you!