23 (Surprising) Reasons To Work for Yourself

  1. You discover things you never knew about yourself.
    For example, you know how sometimes people play that annoying game and ask you what you'd do if you only had 24 hours to live? And so you sit there and scratch your ass, and then say something poetic like, “I'd go to the beach and let the wind whip through my hair one last time.” Alright, Robert Frost. Maybe you would and maybe you wouldn't, but the fact is you'll never know how you'd react to something until it happens. And it's no different when you become a business owner. You'll never know what kind of leader you'll be, what kind of boss you'll be, and even what kind of moral you are until you're in the thick of it. And once you are? You learn a hell of a lot about yourself—like what kinds of things you do when nobody's looking. (I PLEAD THE FIFTH ON ANYTHING THAT HAS TO DO WITH LEFTOVER PIZZA.)
  2. You'll learn a lot more about life than most people.
    No matter how successful you become, every single day you'll be kicking and screaming and fighting to stay ahead, and when the pressure's on, you'll have no choice but to figure it out. In order to do that, you've got to learn stuff. And by stuff I don't just mean accounting and taxes, I mean important stuff, like how to relate to other human beings, and how to make things happen for yourself. Despite the way I probably just made that sound, this is a good thing.
  3. You get insta-respect from anyone you meet.
    I own a business” is one of those things that, whether you own a strip joint or a venture capital firm, gives some weight to your name. And when you're perceived as someone worth respecting? That can help you open doors. (Gracefully, and without having to bribe a guard.)
  4. You learn how to stack the deck in your favor.
    Most people are deathly afraid of risk. Even the word “risk” conjures up images of flashing red lights and high-pitched sirens. But risk isn't always risky. As a business owner, you learn how to take what's called calculated risks, because even though there's a chance of loss? There's an even bigger chance of gain.
  5. Your 899 years of hard work can result in wealth instead of a pink slip.
    When you're working for yourself, you're building an actual ASSET. One that you might even be able to sell someday. When you're working for someone else, you're dedicating years and years and years and years (and years) of your life making someone else rich…and you walk away with nothing.
  6. You can have as much fun with it as you want.
    I send my new writers a hilarious glass whiskey decanter engraved with the words, “Official TMFproject writer's elixir” on the front, and during our Monday morning Slack meetings, we laugh together and make jokes and have fun with our work—including any of the challenging stuff that happens. And when you have fun with your work, you inevitably do a better job. Win win.
  7. Your income isn't capped, and bonuses come any time you feel like putting in a little extra elbow grease.
    I'm talking about the difference between $40,000 take home and $200,000+. Running your own business is one place where your creativity actually pays off—and not merely in the form of a pat on the back.
  8. People who tell you that you “shouldn't start a business in this economy” are wrong.
    Job security never existed in the first place. And in “this economy,” making it happen for yourself is, quite frankly, your safest bet.
  9. You don't have to answer to anyone about what time your gynecologist appointment is—thank fucking god.
    I'm not sure how so many people don't mind asking permission to live their lives. But for the small business owner? Time becomes a resource you can use as you please: not something you have to beg for.
  10. You get to do wildly interesting things every day.
    Nothing is stagnant. It's always changing & it's always changing you. New projects, new ideas, new experiments, new people, new perspectives. Even if some stuff is a pain in the ass, life would be boring if everything were always rosy. You don't want to live a boring, predictable life, do you?
  11. It builds (healthy) big heads.
    Just think about your first kiss: When you hadn't done it before, it was UNGODLY INTIMIDATING. Then you did it once, and it wasn't so bad. (Minus a few instances of tornado tongue.) Then you did it again, and you were feeling pretty smug. Then you did it again? And you're all, “This is CAKE, BEST KISSER IN THE WORLD.” See how you got nice and confident there? Let's call this…the kiss effect. Now, multiply that by about 189, because when you start mastering more, ahem, high level activities? The kiss effect sends your confidence levels through the convertible roof.
  12. You can actually give a damn.
    You get to choose who you serve, and how you serve them, which is clearly better than existing solely to serve just your boss' bottom line.
  13. Some of my biggest business deals happened while I was in the Bahamas. And Spain. And Argentina. And Costa Rica. And Chile, of course. (Because I'm always in Chile, right? YOU'RE SO SICK OF HEARING ABOUT CHILE.)
    Not only is the ability to work from anywhere one of the greatest benefits of this gig; regular travel is also incredibly stimulating for my creativity and my overall mood, which makes me less of an a-hole and a better person to be around. And when I flourish, my business flourishes.
  14. No pants.
    Self explanatory.
  15. You get to deduct your new Macbook.
    And other business-related expenses—even a portion of your rent, if you work from home. Hot DAMN.
  16. You'll feel ALIVE.
    When you feel in control of your life and your future, you feel inexplicably, uncontrollably ALIVE like never before. There's something to be said about the thrill of the hustle, and the love of the game. And nothing—nothing—feels better than your own agency.
  17. Speaking of success: failure, its pain in the ass cousin, will happen.
    But the good news is this: running a small business is basically the world's greatest form of personal development, so even if you completely bomb everything, you're still going to end up ahead. Have faith in that. Did you hear me? HAVE FAITH.
  18. If you're planning to have a family, you can actually see them.
    This isn't something I have first hand experience with since, up until about a year ago, the sight of crying babies made me want to hurl myself into a pit of knitting needles, but I get it. And in more ways than one, having flexibility with your work schedule and your time is something that no amount of money could ever, ever make up for. It's IMPORTANT. And it's one of the biggest benefits of being a small business owner: you get your life.
  19. The internet makes everything easy: even starting businesses.
    A long time ago, starting your own business was a tall order; now, with the internet on your side, you've got zero excuses. You can get more done in 15 minutes than most traditional businesses can do in 3 hours.
  20. What could have been sucks.
    And you never want to find yourself in a place wishing you would have.

Oh, hell. That was only 20 reasons–not 23. But guess what? Since I'm the boss, I get to say THAT'S OKAY. See how this works?



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