Finance tips for the self-employed

This is probably what you think self-employed looks like:

I’m at an amusement park with my kids, in the middle of the week, and I’m on a conference call while I watch my son try to get on a ride.

Being self-employed looks so nice at an amusement park. The self-employed are always free to go on a vacation. They pick up their friends at the airport in the middle of the day, they show up for poker night because they can stay out late, and they can plan their wedding without having to pretend they are working.

Close up, though, most self-employed people are completely stressed about money.

That money part is what I hate about being self-employed. Anyone who says they don’t love a steady paycheck is lying. A paycheck is so nice. It’s reliable like a friend, it makes you safe, it gives you a way to organize your life.

Here’s how I deal with the worrying:

1. Pretend you have an out.
Sometimes I have to calm myself down by telling myself I’ll solve my money problems by taking a regular job. One fantasy I have is getting a job at Microsoft. Once I was giving a speech at a human resource convention in Seattle. And a top HR guy from Microsoft was there. And he wanted to talk to me.

I thought, “Great, I’ll sell him something from Brazen Careerist.”

Then I thought, “No. I just want a job.” I thought I’d do anything—even read resumes all day—if he’d just give me a steady paycheck and access to the amazing health care they give autistic kids of employees.

I hear Microsoft is ending that insurance plan. I wonder if this will help me stay more focused on running my own company instead of looking for escape routes. Probably not.

2. Forget living in the moment. Instead, live five months in the future.
Your clients will take too long to make a decision, no matter how long they take, and they will never pay immediately. So instead of fighting the lag-time, you should always be earning money for five months out. If you are spending your days trying to drum up business to get revenue five months from now, you feel safe, knowing that it’s not an emergency. Any closer than that and you feel like if you don’t close you’re gonna die.

3. The only way to feel rich is to be able to dump an awful client.
Thinking five months out frees you to dump a client, and it’s so so fun to dump a client who misbehaves. It’s a way to assert your power as a freelancer even though you have no power because if you don’t get money you’ll starve and have to get a staff job somewhere (and you probably can’t – because most self-employed people are largely unmanageable in a corporate hierarchy).

I had a client that signed a contract to pay half up front, and then didn’t. And the company was so late it was almost time to give the speech. And I said, if you don’t pay this week, I’m not doing the speech. I loved that. I loved that because I don’t need the money from the speech. I’m okay for right now. Well, I mean, I’d really like the money this week. But I’m okay for next week, so I liked telling her to fuck off.

4. Have one great client.
You need a lot of schemes. You have to always be pitching different people different stuff because you don’t know what’ll stick. But you really need one client that is great, and pays on time, and makes you love doing your job. That client gives you sanity.

For me that is Federated Media. Really, I could write a whole post about how much I love them. They are so easy to work with and they sell ads that I’d never sell on my own, because I’d get impatient and tell the advertiser to fuck off before I collected any money. So Federated makes my life great, because I can blog about anything and say yes or no to anything and they just roll with it, and keep selling ads. Well, they did tell me to remove the word fuck from a post. But that’s how you know that Federated didn’t pay me to write this post. Because they allow pretty much anything except obscenities, which they say fuck qualifies as.

5. Self-employment stability requires doing stuff you hate.
Be a grown-up. Self-employed doesn’t mean you love everything you do. I have done stuff to appease editors that drove me crazy. I have given speeches to groups of people that were all at the conference with the sole purpose of cheating on their wives. I do lots of stuff I don’t like. I remind myself that I do it so that I can have a job that I pretty much love.

To cope with the bad stuff, you have to find a way to trick yourself. Like, I don’t love the pressure, but I love writing about the pressure.