23 Reasons Working For Yourself Will Drive You to Drink

IN: Business 101, Hard Stuff

I want to find a way to say wanker in this post, but since I’m not British, it feels a little unethical. Like I’m stealing words that don’t belong to me.

I’m not sure why I want to say wanker; I’m not angry in the least. But now that I think of it, a few things have inconvenienced me lately.

Like the fact that my Wifi signal decided to take a pee break three times during an important (first) client meeting yesterday.

Or this stiff neck I’ve acquired from sleeping on ruthless Costa Rican pillows, which are more like limp doilies stuffed with used cotton balls.

You know, sometimes stuff gets…tricky.

Out of the thousands of people on this planet, there are at least 2.7 people in this world, give or take, who have emailed me at one point or another, saying how cool my life is. Yes, it is cool. Working for myself is cool. Being an entrepreneur is cool. Traveling all over the place is cool. Calling the shots is cool. Hiring people to help you is cool. Doing fun projects is cool. IT IS COOL.

But in case you’re contemplating striking it out on your own, I also think you should know about the other stuff that happens every day, not just to me, but to all entrepreneurs. At least, I imagine. (And if this shit doesn’t happen to all entrepreneurs, I call shotgun in heaven, jerks.)


  1. You call the shots, but you’ve also got to take the hits. Client not happy about something your team created? It’s up to you to fix it. Uncle Sam need an extra $5,000 this quarter? PONY UP–and then figure out how to ride sidesaddle.
  2. You have to learn how to be a bitch. Deadlines aren’t just an arbitrary date your boss imposed; now, they’re your ass. And if other people aren’t meeting them–like your employees, your contractors, your web designers, or whoever–you can’t just make nice and say, “It’s okay!” Because it’s not. (Note: You don’t really have to be a huge bitch. But you do have to learn how to be more assertive than you’ve ever had to be before.)
  3. You’ll have your emo moments when you just want to put on a black hoodie, close all your curtains, and hide from the world. Because it can be overwhelming, and you’ll be talking to more people in one day than you used to talk to in a week. And even though you’re working alone, it will never feel like you have any alone time.
  4. You need more math skills than 2 + 2. Most importantly, in the form of profit and loss. You might be booking yourself like crazy, but are you actually making any money? Or are you spending more than you’re making? And can you clearly see that? If your personal expenses are mixed in with your business expenses, it’s going to be muddy. (Also: If your personal expenses *are* mixed with your business expenses, you’re screwing up.) In the beginning stages, loss can be expected, but don’t forget to plan for it.
  5. Everything rests on your shoulders. And you’re going to feel stress, pressure, anxiety, and random crying spouts every now and again because, well, everything rests on your shoulders and the only person who can handle that without ever cracking is Indiana Jones and YOU AREN’T HIM.
  6. You’ve got to learn to roll with the punches, without doing any punching. There’s going to be a lot of things that happen that are out of your control. And you’re not going to like it one bit. So roll your neck there, high strung Harry, and practice the ancient art of chilling. (Even though you won’t want to because your life and your sanity and your livelihood and your everything depends on it and why can’t everything just go according to plan?)
  7. You’ve also got to know when it’s better not to roll with the punches–and step up your game, instead. Don’t be lazy. If you can do something about it, you should.
  8. You’re legally liable for a lot more than your auto insurance. Did you know that if you’ve ever accepted money for services or, say, an eBook, then you’ve automatically formed a sole proprietorship? (If you didn’t already register yourself as a formal business entity.) And that means you’re automatically a business? And since you’re one in the same, your personal bank account can be liable for anything that goes wrong? (Say, a rogue random on the internet buys your book, follows your advice, and then tries to sue you because it didn’t work, and ends up taking your child’s college savings.) Stop doing business with your pants down.
  9. Your back’s going to hurt, and you’re not going to go to the chiropractor because you’re too busy for that. You didn’t think staring at a screen for 15 hours a day would be good for it, did you? Work hazards, indeed.
  10. There’s a strong chance you will hate yourself. You’ll hate that you can’t do it fast enough. Or good enough. Or witty enough. Or smart enough. You’ll compare yourself to everyone and everything. You’ll hate that you can’t pull yourself away from your work–even when you sincerely TRY. You’ll hate that you have no work/life balance. You’ll hate that you don’t care about work/life balance. You’ll hate that this thing has taken over your life, and you’ll hate that you LOVE IT.
  11. Your friends will assume you never do anything.  They’ll all think that working from home means not working at all, or that you can talk for 2 hours on the phone at high noon, or you can run errands for them, or that you should have time to Facebook message them back because you just work from home, right? What are you DOING all day?
  12. You have to learn how to market yourself–and be damn good at it.  There are two things you have to be good at: What you do, and marketing what you do. Period. Otherwise, no one is ever going to know about your stuff, and no one is ever going to buy your stuff. And if no one buys your stuff, then you’re out of business, and another dream just fell into a canyon to a painful, bloody, disgusting death. Marketing is the number one skill you need.
  13. You can’t just lay around watching Mad Men all day.  Self-discipline. Get some.
  14. Your do-it-yourself attitude will kill you.  There wouldn’t be enough hours in your entire lifetime to do everything that needs to get done in your business, even if you tried working from now until age 89. So accept it, and then hire other people to do other stuff. Not only will you be able to concentrate on what you do best, the experts you hire? Will help you do the other stuff best, too.
  15. You’ll be a slave to email. You’ll want to close your inbox but you’re just waiting on that one client to get you over that one other thinggg…or you’ll answer all your emails and see inbox zero – fucking miracle – and then those 20 people you just responded to? Will respond back. And then it’s time to do it ALL OVER AGAIN! Learn to love it. Or, pause your inbox. Sort of like pausing life, except not. (You wish.)
  16. You’ve got to love paying people.  Because you’re going to end up spending thousands of dollars on things you’d never thought you’d spend thousands of dollars on. Like someone to help you manage your email.
  17. There will be no guy in cubicle 9 to have a crush on, who would otherwise make waking up and reporting for work every day WAY MORE FUN. Just saying.
  18. You have to learn how to make a fucking decision. The most important skill I’ve learned as a business owner is how to make a decision quickly and cleanly. You’re going to have to make a lot of decisions every day, and if you can never decide what to do about anything? You will NEVER get ahead. Make decisions often. Totally screw ’em up if you have to, but make ’em. And keep moving FORWARD.
  19. Success is elusive. You’ll set your first goal for 6 figures. And then you’ll hit it, and you’ll be like, wtf? That wasn’t so hard. So you’ll set your goal for double that. And you’ll hit it. And you’ll still kind of feel like WHAT NOW? And so you’ll keep adjusting your goals, and you’ll never really feel successful because by the time you hit your goals, you’ll have developed new ones. And it’s one big, giant continuous circle–sort of like a giant piece of calamari, except you don’t get to dip it in anything delicious.
  20. “Done for the day” does not exist. Ever.  I love when someone asks me “if I’m done working.” I’m never done working, because there’s always something I can be doing to improve things. So to answer your question: No. I am not done working. However, I can put it on pause for you if you’d like. (But if you’re going to mess with my flow, there better be a cold beer involved.)
  21. You’ll ring necks for Wifi. Enough said.
  22. Everyone will always want something. Maybe it’s because you’re the top dog, or maybe it’s because you’re an expert now because you own your own business, but either way, you’re going to get flooded with requests for your time every single day. And you’re going to have to learn how to politely decline those requests, or risk getting eaten alive by them. That is not an exaggeration.
  23. Every single day you’ll wonder if you’re doing it right. And every single day you’ll doubt you are. And every single day, you’ll need to take yourself by the hand, sit yourself down, and tell yourself to buck UP. Because there’s no crying in baseball–only in entrepreneurship on days when your Wifi doesn’t work, and you have a stiff neck, and you just realized you’re out of creamer after writing an obnoxiously long blog post that has an awkward number of 23 bullet points instead of 20 or 25, but you don’t really care because you just don’t, and inevitably someone is going to respond to this post with a pep talk about “setting boundaries in work and life,” which I’m immediately going to forward to Meredith because responding with, “THE ONLY BOUNDARY I CARE ABOUT IS THE ONE SEPARATING THE LOSERS AND THE WINNERS” would be rude, and I pay her to help me so my brain can stay FRESH for the writing and the strategizing and the other high level things that people pay me to do, before the neighbor drops by and wants to bullshit for an hour since they think I don’t do anything, and that call with my accountant at 2 o’clock to learn how to do math more advanced than 2+2, before responding to 49 new messages, and then, before the end of the day, I’ll suddenly realize that I didn’t get half the things done on my to do list, which will prompt me to immediately freak out and ask every single person on my team to do extra work, because I’m terrible at logistics, and I always think I can do everything myself, and turns out? I’m just your average entrepreneur wanker trying to make it in this crazy, maddening world that inevitably DRIVES YOU TO DRINK.


Bottom line: Kids, you can try this at home…but don’t say I didn’t warn you.