Design Your Life To Start A Startup

I was a guest speaker at a Columbia Business School class this past week and one of the questions a student asked was, "Should I only apply to remote jobs if I want to start a startup on the side? This way I avoid time wasted on a commute?"

I gave a random answer in the moment but thought a bunch more about it — should people working on startups on the side push hard for remote work to avoid the commute? Say your commute is 30 min a day, twice a day. Hour a day, 5 hours a week, 20 hours a month. Imagine working 20 extra hours a month on your startup?

I mentioned this to my wife and she responded, "Well, don't people spend like 3 hours a day on their phones? Maybe start there?" Turns out it's higher than that.

It reminded me, again, that if you're working on a startup idea you're doing two things. Working on that idea and working on your life so that it can support that idea. If you want to build something long term, the second is more important than the first. We're all goldfish and we've grown to the size of our bowls — no one has any "extra" time.

To create room for anything new in your life (a startup, an exercise habit, a committed relationship, etc.), you’ve got to let go of something old. We stink at this.

There are two types of removable things that hijack your life and they’re both tricky.

The first is the obviously bad stuff. You know what it is — Instagram, Tik Tok, LinkedIn (or your social media of choice). Could be a relationship that drags you down. Could be diet or staying up late or, really, anything. The point is it's pulling your time and energy and you know that. Since you know it's bad, the solution is a system, not willpower. Willpower hasn't worked.

So, pick something you want to stop and over-engineer a solution to it. If you spend an hour on Instagram a day, reset your password to something random with a lot of numbers, send it to your mom, then tell her to only give it to you on Sunday. Then, an hour later, change the password and send the new weird one to her. If it's diet, take a picture of everything you eat and send it to your best friend. Whatever makes you feel bad about doing the thing or makes it literally impossible.

Next, fill the hole with something useful. When you feel like checking Instagram, have a list of 3 things you'll do instead that move you towards something useful. Watch a module of Tacklebox, write out three possible H1s to a website, send a cold email, read 7 pages of a book, do 5 air squats, call your brother. Have a plan for the gap or something equally as useless will fill it. I have a list in my notes app of "5 minute useful tasks" at all times. It's helpful.

The second is the hidden stuff. These are harder to find and change, as they're subconscious. You feel a certain way because you’ve always felt a certain way and it probably roots back to something I’m completely unqualified to dive into. But, for entrepreneurs, I’ve found there are four daily questions that’ll help. We’ve discussed them but I cannot discuss them enough.

If you cut 20 minutes of the first type of debt from your day and fill it with this 20 minute exercise every day, your business (and life) will fundamentally change:

1) What would I do if I were 15% more assertive?

2) What would I do if I were 15% less concerned with what people think of me?

3) If a brilliant CEO took over my job today, what’s the first thing they’d do?

4) If someone took control of your life today, what's the first thing they'd change?

The job of an entrepreneur is to notice things about people. If you do that better than competitors, you’ll usually win. I’ve found that the best way to get there is to make sure you notice things about yourself, first - the habits and ruts you're in, the things you’re naturally good or bad at, the thrust and drag of your daily life. All of it is malleable if you notice it and build systems to change it.

It’s the type of thing that's endlessly useful to come back to.

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