2 min read

I know you're thinking about quitting your job

Most of you know that I quit my job to start a business earlier this year. But few know that I was plagued with indecision for months.

Since I’ve quit, I’ve met many people who feel the same.

I want to write a post to my past self, back to when I had my first inklings. My hope is that if you’re going through something similar, this helps you too.


Dear Aamir,

Thinking of quitting your job to finally start that business you always dreamed of? I’m here to let you know that you did. You quit, you’re me, and I’m here! That shouldn’t surprise you - from the second you worked at that startup in grad school, you knew this would happen.

But getting here was more painful than necessary. So I’m going to tell you a few things that’ll save you some trouble.

First, you know you want to quit, you just don’t know when. You want to wait for the perfect time. Because you think you have time. But you don’t.

Quitting will never be easier than right now. You have no dependents. No major health problems. No crippling debt. No emergencies that cut into your rainy day fund. Your network from college is still fresh. And you’re early enough in your career to make mistakes.

Read over those again. Each of these factors are as good as they’ll ever be. They only get worse with time.

Take on all the risk you can, because if you completely fail, the worst possible situation is: You’ll need to move back home and find a job. And if really can't find a job, you’ll still have a roof over your head and food on the table. That's the worst possible outcome.

And the best possible outcome is that your life will completely change, and you’ll achieve your dreams and more.

That's some asymmetric risk right there.

Don't wait too long. Every day you don’t pursue your dreams is another day you train yourself to think you’re incapable of achieving them.

Start writing. It’s hard to make decisions when you don’t have conviction, and seeing your own thoughts on your page helps you accept them.

Once you’ve decided you’re ready, a few things to keep in mind:

Half-assing things doesn’t work out for you. Don’t try to start a business and stay at your job at the same time. You’re the obsessive type. Lean into that, use it as a strength. Go all in.

Every $70 you spend is one less day you have to get your business off the ground. Cook more, and practice some trigger discipline with Amazon Buy Now.

Like most anxiety inducing decisions in life, it feels like the world is ending before the decision, and much better on the other side. Despite not having an income, I’m as happy and carefree as I’ve been in years.

You’ve lived a structured path for most of your life. When you begin to live life on your own terms, opportunities unfold, serendipity abounds, and you’ll be on your merry way…

…wondering why you didn’t just do it earlier.