Don't Worry, I Got This

How To Be a Self-Employed Freelancer

How To Be A Self-Employed Freelancer

On Flying Under the Radar and Playing Battleship

freelance writing

A few months before I left my job to travel for a year, I had a bad day at work. I don’t even remember the specific circumstances of this day, but I do remember this: I was crying by the time I left work and four minutes later when I got home, I stood in my driveway, clenched my fists by my sides, squinted my eyes and screamed:

“I. Am. Never. Working. For. Anyone. Again.”

With an emphasis on Never.

I’m sure I looked like a toddler in the midst of an afternoon meltdown. My buddy Chris, who happened to swing by our house at that moment, stood opposite me, paralyzed and wide eyed. I had had it.

Two years later, I’ve realized that creating the life that I want still does not involve having a boss, performance reviews or two-hour staff meetings. Yes, I know, I still have responsibilities, accountability, and I still work with people on a regular basis. I play well with others and I do good work.

The thing that floors me though, is that I really thought I would be better at this from the get go. I had visions of working in the mornings and going for bike rides in the afternoons. Or sitting in airports on my laptop, chain drinking a Americanos, writing emails to clients. Pretty much thinking I was Hot Shit.

I would be a smooth operator. A sovereign nation.

Freelancing in style.

I’m not there—yet. Instead, I often feel like I am flailing, like when Wiley E. Coyote jumps off the cliff and his limbs continue running in mid-air.

But here is what I have learned so far.

Listen To People: Rely on the wisdom of self-employed or business owning friends to remind you that you are doing the right thing. These people verbally slap me across my face and tell me that I will survive and that I won’t end up destitute, scavenging food out of the dumpster behind Trader Joe’s.

Don’t Listen to All People: Choose wisely whose advice you follow. Fortunately, I have had only one person tell me that what I was doing was a stupid idea. On our way home that evening, my husband kept looking over to me saying over and over again, “Don’t cry. Don’t cry. Don’t cry.” In retrospect, that person did me a favor. I still hear his voice with every little success.

Trust Myself: Another friend told me that when I find myself in a moment of desperation, thinking that I couldn’t do this, I should scribble a big sign to put above my computer screen that says “You are awesome.” How goofy is that? Pretty goofy. I might do it.

Pay Attention: To jobs that you like or jobs that you dislike. And pay attention to clients that are a good fit or not a good fit. This is important. Crappy jobs and crappy clients = crappy work.

Realize That You Are Already Doing It: When do you call yourself a writer or a graphic designer or a crime fighting ninja warrior? The minute you start doing it. Just keep doing it.

Fly Under the Radar: Sometimes its okay to quietly do your work and take cautious baby steps to move forward. It pays off in the right moment when you do need to sell yourself or jump on an opportunity. Pimp it at appropriate times only.

Work Smarter, Not Harder: When you work, you work. When you are not working, you are not working. Simple in theory. Not so simple in application, especially for us writer types.

Play Battleship: Find a mentor, friend, colleague or partner with whom to collaborate, gain support or help garner ideas. Meet up for a working coffee, lunch, beers, whatever. I call this “playing battleship”, sitting across from each other at the coffee shop with our metallic laptops, looking nerdy.

Security Is An Illusion: It’s frigging stressful sometimes being your own boss, and you’ll often feel like you are jumping without a net. I don’t always know how much money I will make next month or if a client will fire me tomorrow. But, never, ever believe that being an employee somewhere else is 100% secure. It’s not.

Do What You Are Supposed To Do: This is a little different than “follow your bliss” or “do what you love”, because I don’t quite buy either of them. I love surfing, but it would be laughable for me to make an income off of surfing.

You know what you are supposed to do. Do it.

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