Editor's Note: If you missed last week's email, check it out. It will help this one make a lot more sense.
What was I thinking?
Usually, when you quit your day job, it's because you hate it. It suffocates you. Drives you insane. You can't stand your boss. And you especially can't stand that annoying coworker that always swings by for a chat - and never leaves.
Not me. I had coworkers that I enjoyed working with, an amazing boss, and a great working environment. The best part, though? I got to work on some really cool stuff. Really. Cool. Stuff.
On a scale of 1 to cool, this job registered a 10. That's because I was basically paid to travel the world and sell stealth fighter jets.
No lie. It was the sort of job they make movies about - never mind the fact that the movies are always sexier than real life. Even so, I got to see the world on the company’s dime. Belgium, South Korea, Poland, Turkey… the list goes on. I've swam the Dead Sea, toured the Italian Alps, and sampled sushi in Japan. And the perks didn't hurt either: First class tickets, fancy dinners, and free champagne everywhere you turn.
More importantly, the work was fun and rewarding. I got to witness our fighters fly for the first time in Milan, celebrate the arrival of the first two in Israel, and negotiate a $7 billion deal in Seoul. It was truly satisfying work.
Which leads you to wonder, why would somebody leave all this behind? If it was as great as it sounds, why hit the road? The answer is actually simple.
I was scared.
People ask me a lot - What was your tipping point? What made you decide to finally make the leap? Sure, I was terrified of leaving. Very scared, actually. I’ve been working with the same company for close to a decade, after all. But there’s one thing I was even more scared of.
I’ve put my heart and soul (and a good amount of life savings) into this business. Sure, I could keep running it as a side hustle forever. But in doing that, I would always wonder. What if I had really dug in, really given it everything I had? What could I have built it into? Would it be something I was truly proud of?
There’s a trend among entrepreneurs today. We’re all trying to start businesses that produce a passive income stream so that we can move to the Bahamas (or travel the world) and live off that income into perpetuity. Mailbox money.
And I'll be honest - that lifestyle sounds pretty amazing. Who wouldn’t want that? But I’ve found in this past year that there’s something I want even more than that. More than the cushy lifestyle or the margaritas on the beach, I want to work. Really hard. I want to build something that I’m proud of. Have an impact on the people around me. I want to go to bed at night exhausted and wake up ready to do it all over again in the morning.
Maybe you think I’m crazy. And maybe I am. But here’s the thing: I’ve never felt more uncomfortable before in my life. And as a result, I’ve never felt more alive or excited about what’s ahead.
Leaving a plush corporate job is terrifying. But for me, it’s been one of the best decisions in my life. At least so far. The timing isn't perfect, and there are many holes in my plan. Most of them I probably can't see. But the timing will never be perfect. The planets aren't going to align, and the sky isn't going to part to reveal the path forward. So I'm doing the only thing I can do - trust my gut, and take a leap.
Tim Ferris wrote that "someday" is a disease that will take your dreams to the grave. I would add that when they get there, you'll only be left with the "what if's" that remain behind. I've had this dream for a long time now. And I refuse to let all the someday's take it to the grave. For better or worse, I'm all in.
I will say this, though. If anyone out there wants to drop weekly checks in my mailbox, I won't refuse. And every now and then I'll probably spend it on a trip to the beach and a few margaritas. But after a week of that, I'll probably get bored - and I'll make my way home. To get back to work.
Until next week,
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