This is an open letter to those who are choosing to join the collective insanity of self-employed creatives (ie YOU), to be read on the first day of your glorious and heroic struggle.

Hello Young Lion, welcome.

There are logical arguments and real world advantages to self employment, but before you go this route, be clear that you are doing it for the right reasons and with healthy expectations. There is a myth of business ownership, many people believe going into business for themselves is “the answer” to woes in their working life. And it can be, provided there is a solid game plan and acceptance of additional burdens and responsibilities.

Meet Benny

Let us consider an example in Bernice the Barista. She has twelve years’ experience working in cafes, and she’s aiming to open her own spot, Benny Brews. She is an expert at expressos, killer customer service, and she makes the best breakfast sandwich you’ve ever had. She believes she can be successful and wants to take the leap.

-BUT- for all of her experience at the counter, she has had limited time in the office and with the books. There’s a lot she doesn’t know about running the business, and her success will be determined by how she handles that truth. On the one hand, she can be honest with herself about her limitations and address them, OR she can allow false confidence to lead her to believe that she knows all there is to know and Everything Will Be Fine.

Let’s say Bernice is married to Sarah, who happens to work in accounting with a firm downtown and wants to help her wife set up shop. If Bernice is receptive to Sarah’s input on setting up Benny Brews, it definitely means shortcuts through the minefield of forms and red tape. They attend small business seminars together and brainstorm over Burgerville afterwards. Additionally, that personality type, a team building leader, will have an easier time of finding and retaining loyal employees.

But let’s say Benny’s a diva, she’s made one too many killer paninis and it’s gone to her head. She says something idiotic to her poor wife like, “Do you know latte art? NO. I don’t know your world, you don’t know mine, thank you babe but no.” This also says a lot about what her business culture will feel like, a totalitarian bossypants who has to have things her way. Benny will never understand why she has such a high turnover rate with her employees.

You Better Budget

Now, being a freelance creative is not quite the same as opening a brick and mortar food service, there’s WAY less overhead (2k for a decent work computer vs 10k+++ for all costs on the shop), but it is still a business and is similar in that there are strategies that lend themselves to success and bad habits that can bring our plans to ruin.

Fastest example possible, you just made $500 for designing an album cover. Sweet! $500, right? No, not really. Even if you’re Starvin Marvin dying for your next brick of ramen, you should only spend half of what you’ve made — considering that about a third-ish of it will go to taxes and it’s good to squirrel away what you can when you can. So out of a six-piece pie of $500, $250 goes to rent (three pieces), $167 is set aside for Tax Man (two pieces rounded), one is set aside for whatever ($83, retirement savings, food, liquor).

If you’re not ready to think about finances in this way, you are not ready to be your own employee. When self-employed, you are your own boss, you have a responsibility to yourself. You have to treat yourself well. If you only get paid five times in a year, but those checks are substantial, you need to budget yourself to make sure that your income covers your costs of living. If you make 20k in a day and lose your mind, go to the car dealership and pick up something for 18k, you might wind up having to flip it within a year to cover the taxes.

Small Ponds and Peergroup Galaxies

Then there’s the matter of the racket that you are trying to break into — let’s continue with the freelance creative example, specifically someone looking for an angle into graphic design. This field is *extremely* saturated, you are jumping into an active and viciously competitive pool.

How does your portfolio look? Where have you worked? What brands have you handled? Who do you know? These are the questions you will be asked, and it does you no good at all to try to puff your chest out without any work or connections to back it up. The name of the game is collateral, finished product, what you can show and speak to. On a secondary level, who you’ve worked with and who can vouch for you. Reputation is worth a lot.

If you’ve just got a couple of personal projects under your belt, don’t swag around like you’ve done real work yet — keep your tone humble and remain grateful for the opportunity to be at the table. There are a dozen kids behind you with Macbook Pro’s who can’t wait to take your place.

Back to the cafe model, you don’t open up a new shop in a neighborhood full of coffee houses and pretend you are changing the face of the block. Calm down, it’s just coffee, and if you present yourself like some massive upstart gamechanger, every single Average Wednesday will tarnish your reputation. You definitely want to find the things that can make your shop stand out in the neighborhood, but don’t pitch it like your customer will find The Truth and The Light at the bottom of every cup.

Just Like Clockwork

Similarly, as a working creative, you want a reputation for solid, dependable, reliable work, you don’t have to be the gamechanger. It’s cool to have a couple of stories in your pocket about being the last minute hero/heroine who saved the day, waaay better to have a track record for knocking things out on schedule. Save the true war stories for other veterans, they will appreciate them.

Carve a niche for yourself in a peer group of solid, dependable, reliable workers by doing solid, dependable, reliable work. Have cool and interesting things on the side, only way to keep yourself seasoned and in tune, but always remember that quality in the work comes before your ego or pride in what you do. Worry and lose sleep about the quality of what you are delivering, not how it is going to be impact your reputation.

If you put the time and love into it, the attention to detail, that will be your reputation. That is the one you want.

You’ve got to be good at what you do, from cafe’s to graphics to code to elephant polishing, long term survival is dependent on talent. But you have to be even better at the business around it, accounting and promotion and management and all of it. Both are full time jobs, and the Truth at the Bottom of This Cup is that it is MUCH EASIER to be someone’s employee. You show up, you clock in, you do your job, you clock out. You have your evenings free for crochet and Netflix. You can have normal hobbies.

Born Different

Then there’s us, and I’ll quote my old friend William Melody’s sentiment, “I just can’t be an employee.” For whatever reason, we don’t fit into the nine-to-five, team player model, and that’s where the freelancer / contractor / self-employed piece of it comes in. We’re happier working longer hours, wearing more hats, taking more control (for better AND worse) of our finances and earnings. Pleased as shit to be awake at 2-3AM, wrapping your head around a new method or technique. It’s a certain kind of mind and person that (dis)functions well this way.

Even the more social of us, who do go out to meetups and have bowling teams and bands and go rock-climbing, there’s always a background track (or five) in the mind about what is happening in the business and how it can improve. Another independent in the room? Guarantee those two are comparing notes on how things are going. It is a part of life, like breathing, you do it without realizing you’re doing it.

And now I get to be contradictory and say that there are circumstances in which I would be an employee, absolutely. Even if only in my mind, there would be a defined period of time for the gig (five years, say), with specific reasons that I am working in that lane, at the company, to allow me more time in my life for _______. But until those stars align, I still enjoy defining my orbit through these systems of life, working in a craft that continues to challenge me after 15 years, and perhaps I will never be an employee again. I have my plots but some things are best left to Fortuna.

So where do you think you fall? Do you still want to own your own painting business, or are you happy working for someone else’s? That’s the real distinction, the real difference, and I’m not offering it up as a value judgement or a superiority thing. The best leaders I’ve seen hold a belief in equality of players in the team, the worst have promoted cultures of elitism.

The world needs players to fill all roles, it’s a matter of being honest with yourself about how you want to do what you do. All of this “Like a Boss” shit is a good joke but I wouldn’t go about it as the tone of your mission statement.