A couple of friends of mine were talking today about venturing out into the world of freelancing. For the first time in my life, I wasn’t insanely jealous. I remembered the last four years of my life and was thankful to have a steady day job to go to. I liked the freedom but I think that’s all that I liked. I didn’t need the freedom to be my own boss, I just needed freedom from a 9 to 5 for a while. My freelance life was essentially living off of my savings and supplementing my income with web development jobs and improv coaching.

I’ve thought about my freelance life and the reasons why it didn’t take off and here they are.

I’m not obsessed with my career

I once worked on a freelance project with a guy who was taking this on at night, after his full-time day job. That’s how much he loved web development. I don’t love it that much. I like it. I’ve come to a place where I realize that it’s interesting and I’m privileged to have gained this skill that I can use. But I’m never going to be on the cutting edge, searching for the newest technology. I need to go to an office, perform a task, then leave. If you’re a freelancer, you should be prepared to work your ass off at your thing. Get obsessed. Spend all night tinkering, researching, learning, practicing. If you don’t want to do that, perhaps stick to the day job.

I’m not a hustler

Freelancers should be curious and obsessed to the point where they’re always looking for new projects and always networking. That’s not really my bag. You know that Actor’s Studio thing at the end where James Lipton would ask “What’s your favorite curse word?” and “What will God say to you when you get to heaven?” I always liked the “What other profession would you have liked to attempt?” I always thought relief pitcher. Setting aside the fact that it’s an incredible stressful job where you have to let past failures go – two traits that are very un-me – I have always loved the idea of having a specific skill and being called upon to use it. Sometimes my job feels like that. I’m often the final step in the process and no matter what the project is, I just have to go in and throw strikes. I don’t have to manage or improve my hitting or worry about the media, I just have to throw strikes.

(It also bears mentioning that a typical day of freelancing wasn’t that productive.)

I can’t do it all

I never appreciated producers, business development, and payroll until I went freelance. I always had respect for designers and back end coders but always wondered what the hell everyone else did. Now I know. They find and then deal with clients. Then, after the work is done for those clients, they bill them. I can’t do what they do. As a freelancer, you have to.

Some Advice

So, you’re obsessed, you’re motivated, and something’s calling you to take the plunge. Cool. You have to do it. Just a couple of things…

With regards to money, account for everything: your rent, your bills, your food, your healthcare, and also the miscellaneous and come up with a monthly budget. Be honest or you could really screw yourself. And let me explain the miscellaneous (I talked about it before here). I’m talking about toilet paper, light bulbs, paper towels, and soap. Dish soap, hand soap, bars of soap, body wash, shampoo. There’s nothing like using that last sliver of soap for one more day because you can’t afford to buy any more. And do you, like, socialize? Go out? Budget that. Once you have your monthly total, save up two to three times that for the lean times, then begin.

Remember that when you don’t go into an office you can go stir crazy, so, be sure to meet up with people.

Put on pants. Every day. Real ones, not pajama or sweat. This is important. There is nothing worse than the feeling of watching the sun set and realizing that you have not put on pants.

I learned things about myself as a freelancer. I can’t say I liked all the things that I learned but I learned them.