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The DIRTY 30 COMMANDMENTS of Working for Yourself: How to Slay Like an Unf*ckwithable Boss

In: Starting an Online Business

  1. When negotiating, put on your big girl pants and start with your BIG ask.

    What’s the most important thing you *really* want out of this? People usually start with their little asks, and then build up to the big one, because they’re scared to death and trying to warm up to it. But, the other side wants you to do that. They’ll happily throw in your little ones, so when you make your big ask—the thing you really wanted (that they don’t want you to have)—it will appear as if you are greedy and demanding. And they will decline under the guise of already having agreed to all of your previous asks. And then you don’t get what you really want—which isn’t the point of negotiating.

  2. There’s a difference between meaningful work and meaningless labor.

    You’ll know you’re doing the meaningful work when you feel guilty. <—That’s important. Meaningful work never feels like drudgery. It feels like fucking heaven. And that’s precisely why you won’t do it enough: It’ll feel too good. SO GO WITH THAT. Use it as a sign. Make sure you do work every day that makes you feel like the guiltiest little shit around.

  3. You’ve just gotta own it.

    No one’s going to make you do the videos, or write the thing.

  4. Learn to pat yourself on the back—even when you fuck up.

    The truth is that you’ll fuck up every single day—and man, do you know how much harder this is going to be if you start questioning your self-worth as a human every single day on top of it? You don’t hate yourself for getting a math problem wrong. Life is nothing more than one big math problem.

  5. Go for the easy cash flow first.

    There are a million reasons why, including the fact that money is a beautiful tool that will help you get traction, but maybe most importantly is the reason that no one ever talks about: Because it will help you feel like everything’s going to be okay. And when you’re in business for yourself, that's really important.

  6. When you feel totally harried and crazy and like you don’t have any time, that’s when you do yourself a favor and stop time.

    I know. I’ve got all the secrets, right? But seriously: Go shopping at Target, go take a drive in your car. Time will slow down. And you will see the big picture again.  The thing is, time doesn’t work the way it used to. Before, an 8-hour day felt like an eternity. Now, 8 hours feels like 5 minutes, because of all the incoming stimulus constantly raining down on your brain. Time doesn’t fly when you’re having fun anymore; it’s the opposite. Time flies when you’re sitting cross-legged on your loveseat with a cold cup of coffee yelling at your computer screen because Paypal won’t load, and the guy on the phone from Avis says he can’t locate your credit card on file, and there are 30 new Twitter notifications, and look there’s an email and WHERE ARE MY TOENAIL CLIPPERS?!

  7. Unsubscribe from your competitors.

    You might be looking for inspiration but the truth is that this is the fastest way to drive yourself to drink. They’re going to get in your head, because someone will always be better at you at something—even if that thing is irrelevant for your work—and next thing you know, you’re going to be PARALYZED. You’ll hold yourself to a standard that isn’t your own—or even the standard you’re trying to compete on. And worse, you’ll accidentally drown out your own voice. Have the guts to create and do what feels good for YOU.

  8. Don’t try to sell meat to vegetarians.

    This sounds obvious when I say it, but it’s not that obvious when you’re starting a business going, “SOMEONE, ANYONE, PLEASE BUY.” Don’t focus on trying to convert people to your philosophy. Don’t waste half of your sales page trying to convince a vegetarian that they really need the Delmonico. You aren’t changing anyone’s worldview with a paragraph or two, okay?  Those things are complex, and ingrained. So know which worldview already aligns with what you’re selling, and start there.

  9. Never ask your family and friends for advice.

    They are not your target market. They will fuck you up in the head.

  10. On selling: Everybody wants something.

    What is it? Sell them that. Then, give ‘em what they need. This is called branding. And branding isn't about your merits; it's about the marketing of your merits.


    WHAT’S THE POINT? WHAT’S THE THEME? If you do nothing else, focus hard on creating a signature. The right brand gets whispered about; the wrong brand gets ignored; and no brand doesn’t even have the privilege of being ignored.

  12. Hire an assistant to do your invoicing and accounts receivables.

    Putting someone in between you and the client to talk money makes the conversation feel more objective, i.e. “Balance due is $10,000” versus “You owe me $10,000,” or even “A late fee was applied,” versus “I’m charging you a late fee.” This is a luxury, of course, but if you’re a softie about asking for money, or spending the money to employ an objective third party middleman can end up be more profitable, not less.

  13. Tell imposter syndrome to suck it.

    If you’re out there getting your ass kicked, you’ve earned it.

  14. If you’re procrastinating something, it’s usually because you think you’ll be bad at it.

    The solution: Reduce a new variable every single day. Not knowing how is only temporary. 90% of the reason why you’re nervous / scared / shitting your pants is because you can’t account for variables. So…reduce them.

  15. You can’t do as much as you think you can.

    Whatever you’ve got on your to-do list, cut it by 75%. That last 25% is what you’ll get done today, so plan for that. Trust me. This is great productivity advice, despite it sounding like I’m telling you to do less. I’m actually saving you from you from a god damn mental breakdown—which surely wouldn't be good for your productivity now, would it?

  16. Always count on something going wrong.

    Your customers won’t be able to download the file; the link won’t work; the internet will go out; you’ll have a massive case of diarrhea. What’s Plan B?

  17. Pitching is the most important thing you’ll ever learn in your business.

    Answer this question: How can I get them to say, “Tell me more?” And then answer it again and again, until you're at the bottom of the page. Suspense is your friend. This applies to pitching things on paper and pitching yourself in person—including elevator pitches. The thing about a pitch is that you can’t possibly say everything at once, so your goal is to simply get from the first sentence to the second. And then the next. And then the next. …And keep them listening. 

  18. Antipathy is the enemy.

    When you start to feel jaded, the people you need to talk to are often the ones you least want to. Important: Have conversations with your customers every week. Not business conversations; just regular, real-people conversations. It will remind you that they are real people, and holy shit, you actually like them. You’ll feel reinspired to help.

  19. Standing your ground on principle will be difficult, but worth it.

    Principle exists less and less, which means that if you have some, you’re ahead of the game. Because even though sometimes it feels optional, eventually it’s the only thing that will matter. The things that once made you hard are the same that will make you soft again. I promise.

  20. Keep meticulous records about everything.

    Make a folder for everything. Then, put things in their folder in the moment as it happens. As much as you think you’ll file it later, you won’t. This is important.

  21. Specificity holds power.

    “I’ll turn the ugliest room in your house into a sanctuary for less than $1,000” is more compelling than “I’ll transform your space.”

  22. The money isn’t as important as the presentation of it.

    There’s a difference between “$75 for three months of access” and “$25 / month, with a 3 month commitment.” Same price point; different presentation. Reduce sticker shock when you can, while doing so in a way that’s classy and respectful.

  23. Use people.

    By that I mean, when that jerky person or business or experience comes into your life, use their presence to show you what you *don’t* want to be. I’m pretty sure this is what they call “looking on the bright side,” but sometimes that’s hard when you’re dealing with creeps. Still—use the experience to keep narrowing who you want to be, and what you want to stand for, and what you don’t. Then, make it known what you DO stand for.

  24. Learn how to distinguish between important things and things dressed up as important.

    You will have to do this every minute of every day, and then have faith that you’re prioritizing well every minute, of every day—which can be hard when everything feels like it’s important. If you’re feeling that way, think about what’s important to *you* first, and then what’s important to other people. Because there’s a distinction there, too. One will make you, and one will make everyone else.

  25. Important skill: Being able to get your head space back, over and over again.

    This is another thing you’re going to have to do every minute of every day. I’m making this sound like a real joy ride, aren’t I? But these are nothing more than new skills that you have to acquire. (Which is why #4 is so important.)

  26. Hotels will change your life.

    Find a great little boutique hotel, and go there for three days. Answer no one’s calls, and no one’s texts. Watch what happens.

  27. Use Freckle or Freshbooks to track your time every day.

    Do it manually – not with an automated program. Manually enter in your work, and review it at the end of each day. (Alternatively, keep a Trello list and write down every single thing you do.) You will always feel like you’ve never done enough; like you slacked off; like you barely got anything done, but the truth will be there on paper.

  28. All you need is two inches.

    GET YOUR HEAD OUT OF THE GUTTER, LADIES—I’m talking about money. Everyone’s worried that they won’t be able to make money, but there’s plenty of money to go around. In fact, there are 1.5 trillion U.S. dollars printed and rolling around through people’s fingers right now. It's not this mythical concept. It's out there! And because no one has any concept of what a trillion dollars looks like, if you started stacking $1,000 bills (because clearly we just have those sitting around) one trillion dollars would be 63 MILES HIGH. In contrast, a million dollars? Is only 4 inches high. Which is really all to say you probably only need 2 inches out of all of that. A two inch stack of paper doesn’t sound half as intimidating, does it? It’s the mental piece that messes with you—not money itself.

  29. Awkward silences are your friend.

    When you state your prices, JUST STATE THEM, as if they were as natural as the hair on your head. Don’t apologize for them, ever. This is easier said than done. But no one wants to buy from a wishy washy, insecure, anxious person. They’re unconsciously looking for signals that they can trust you, and sounding confident is critical. Work on this every day and you’ll get better. …And then it’ll be hilarious the next time you tell your husband what you want for Christmas. <INSERT HARD STARE AWKWARD SILENCE>

  30. Nothing’s that big of a deal.

    Nothing. And especially the decision you’re making right now that feels like it’s DO OR DIE. Nope, not do or die. In fact, it hardly matters. Because here’s the thing about business: It’s always changing. And you are always changing. And you will always be tweaking things forevermore, anyway, so whatever you decide to do today, probably will be different next month. So that’s great news! That means that you can execute without all the anxiety around whether or not things are perfect. You’re going to change them later, anyway. And this is really all just a game. And you are just a player. And nothing you do actually matters that much. So, are you playing yet—or standing on the sidelines worrying you’re going to do it wrong? (Hint: You can’t play wrong. It’s called play for a reason. And that is the key to life, really. Playing more than anyone else, and then not feeling guilty about it. See #2.)

Want more? Try The A-Z Guide to Becoming an Unf*ckwithable Freelancer IN YO' SLEEP.
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I'm a Bad Influence on Women

Hey, I’m Ash! Twenty years ago I was a small town girl growing up in a trailer park in rural Pennsylvania. Fifteen years ago, I lost my family and everything I knew right as I became the first to graduate college. Fourteen years ago, I found myself leaving everything behind for a new life in the city where I could be “normal.” Ten years ago I realized normal was the most disappointing thing that ever happened to me. Nine years ago I quit my job in advertising and pursued my dreams as a creative writer. Eight years ago, I built a 6-figure business doing what I love using nothing more than the Internet and my voice. And now, today, I’m the founder of The Middle Finger Project, an irreverent media co. that helps other women find their voice and teaches them to use it to build whatever the f*ck they want to. With a book coming out with Penguin Random House in February 2020 (YASSS, WE’RE A PRODUCT IN TARGET!) I’m proud to be a bad influence on women and guide them into doing something disobediently brave with their life and their career.

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