Entrepreneurship & Dating

In the months since I left my job, I’ve come to realize that entrepreneurship is a lot like building a relationship with a significant other.

When you start a side hustle, it’s a lot like starting to date someone new. There’s a ton of excitement, you want to spend every spare moment on it, and you’re caught up in the romanticism of it all. It's fun and addicting.

As things progress and you decide to pursue entrepreneurship full-time and leave your job, the magic begins to fade a bit as the reality of every day life sets in. Much like a relationship, you start to get comfortable.

Without a 9-5 and a boss to dictate your every move, your ultimate freedom can become too comfortable and even paralyzing to an extent. Rather than pushing forward, you want things to stay like they are so you do nothing and get stuck.

Rather than working your butt off to maximize the time & effort spent working on the project, you take your foot off the gas because you don’t have to get up and drive to the office anymore. You don’t have to respond to that coworker’s email or your boss's messages.

All of your deadlines and projects are self-driven now. There's no one pestering you and motivating you to get stuff done.

Like a long-term relationship or marriage, you get comfortable. You “got” the dream girl (or job). Rather than keeping that edge and being the energetic, charming person you were before, you get lulled into a false sense of comfort. You get boring. You stop taking risks. You stop hunting.

But that’s a recipe for failure in both entrepreneurship and any long-term relationship.

Keep hunting.

You can’t lure a woman in by being one person (exciting, unpredictable, strong, decisive, etc) and then expect her to stick around when you become another person (boring, predictable, lazy, complacent, indecisive and deferring all decisions to her).

You can’t work your ass off on a side hustle and then turn on cruise control once you’ve left your job. That's a recipe for inertia.

You’ve got to keep your foot on the gas. Stay aggressive. Stay consistent. Stay exciting.