I knew I was unemployable in high school. Yep, that’s right—the project manager that works 60-80 hour weeks when fate requires it of her is unemployable. Another word for unemployable is, dare I say, entrepreneurial? Freelance beckoned.

I had a hard time with authority and being pigeonholed (don’t tell me what to do!), and I felt especially sure that education, and the job market should be some sort of choose-your-own-adventure scenario (um, IT IS).

Long story short, I got spit out of college with a fire in my belly and a vision in my head. Freelance was the life for me—I knew it. Everything about those movies with smug professionals in their pajamas making on-the-spot decisions on calls to Asia was what I wanted. Alas, the job market (and common sense) warranted some 9-5 adventures before I got settled into my freelance career. I did my time, and I’m better for it.

Here are some things that I learned on my journey to finding my freelance:

Being green isn’t all that awesome.

Some people are born confident. They are magnetic and charming. Even if they are blowing it, it’s with style. I, my friend, am not that person. I can be confident, but only after assuring that all of my ducks are in a row. I can be magnetic, but only on days when I feel authentically stoked. I can even be charming, but only if I know my shit. I was full time permanent for around 4 years before I jumped into freelance. I highly recommend this. Being in an agency setting allowed me to test my chops in the real world, surrounded by mentors and kegerators.

Suck up the knowledge, play foosball, get out.

This will enable you to get into a groove and show your best side as you move forward.

You’re never ready for freelance.

The first time something gets fucked up and you’re the only one to blame, well, it’s next-level stuff. With time, this gets easier, but for a while, user error is gonna suck it big time. Do your best to fake it while learning, but be as honest as you can about your skill level. Chatting things through with a mentor is a great way to get a solution-based critique. I made a habit of doing this early and often.

If you don’t make sure the business side of things is handled, things get bad—FAST.

“The Wealthy Freelancer” is one of my bibles on this. Here’re some takeaways:
– Keep track of your money. I don’t care how you do it—spreadsheet, bar napkin, the whiteboard in your mom’s basement. Just do it. Profit and loss are your best friends. When you end up making that six figure salary you are going to want to write off every damn thing you can.
– Get a good book keeper. This is so important. Mine is a lifeline and translator in a world that I don’t understand. Ask for recommendations from other freelancers and small-business owners.
– Pay your effing taxes. I know, this seems super basic right? Well, when I transitioned from the wonderful world of W2s into 1099s-ville it was jarring. Quarterlies? Extensions? What are these things you speak of? Find a great tax-preparation guru, give them an awkward hug, and say thank you in advance.

Sharpen the pencil on your vision, yo!

It may seem cheesy and/or ridiculous, but this has kept me on track for 10+ years now, so … yeah. Write down your ideal day, your ideal week, and your ideal year. There it is. Write them using the most detail you can muster. How do you get up in the morning? What is the first thing you do? Do you want to travel this month? Do you want to take a month off? I think of these ideals as my brief. Whenever I feel off track I go back and review them. Am I on track? If not, do I need to re-write them? Or am I off track because I have forgotten what I set out to do?

After all that, you may become employed again.

The last thing I’ll say is that even after all of the shit talking, you may still, out of necessity or desire, want to take a full-time job again. More power to ya. I’ve done it a couple of times. I always ended up going back to freelance. If you’re good at networking, you may get offered jobs a lot. No lie, whenever that happens to me I have to weigh it out, the pros and cons, every time.

Freelance is not for everyone. The risk is high, the stress is high, the challenges are at times pedestrian, but then they are scary as hell out of the blue. The achievements are your own, though, and the joy of choosing your own adventure is there, every damn day.