1. Are you serious?
What I don’t mean here is — “are you excited?”
Excitement is the currency of the naive. Grit is the real treasure.
You need grit to finish a project you said you would do, even though it will take you until 1 A.M. and even though you will have to get up for a 7 A.M. appointment the next day.
Creating stuff is fun. Making a living from it is serious.
2. Are you sure?
“You’re talkin’ ‘bout the American Dream. You find something that you love, and then you twist it, and you torture it, try and find a way to make money at it. You spend a lifetime doing that. At the end, you can’t find a trace of what you started out lovin’.”
— Justin Matisse, Hope Floats
Just a reminder — not everything you do has to make money.
3. Are you a self-starter?
I once knew this girl — bright, clever, quick, hard-working. At one point in her life, she went after everything, hard. She didn’t wait for instructions.
By the time we had worked together 5 years, she said this:
“I don’t want to overachieve anymore.”
So she stopped.
Later, she was “released” from her role.
It is fine to coast. But not if you want to make a living with creative work.
4. Are you considering you current situation?
I have a friend who left his job. He filmed himself walking out the door for the last time.
Two years later, his life is crazy — a couple children fill his days and work creeps in whenever it can, in the cracks of a naptime or stray hours in the early morning. This strain of non-employment has further choked his time as he and his family are planning a move from Pittsburgh to New York.
The other day he says:
“What I’d really like is a project where I don’t really have to chase clients or build anything. I want a situation where I can come in, do work for someone who has a specific task for me in mind, and then they pay me.”
“Declan, what you’re describing is a job.”
Sure, creative culture clashes with corporate practices. That doesn’t mean your life might demand a structure you don’t have the time to build.
You can be an employee. It’s okay.
You can take projects for money. It’s okay.
You can work for evil advertising. It’s okay.
5. How much money do you need to make?
My answer to this question, for many years, was — MORE.
So I made more. Double my salary, double the book sales, $10,000 extra in freelance work.
Woohoo! More money!
It wasn’t enough.
Personal finances tend to suffer when you are “too busy” to pay attention to them, no matter how many zeros are on your checks. Combine that with an addiction to SAAS products, and you have a recipe for disaster.
Pick a number. A real, reasonable number. Go make that.
Later, (maybe) change that number and make more.
6. Do you know someone who can help with the boring stuff?
Meaning — can a close friend tell you the difference between a tax credit and a tax deduction? Will a person explain to you the difference between filing as a sole proprietor, an LLC, or an S Corp. Can you learn what a run rate is? Should you use a cash or accrual method of accounting?
You probably can’t stand to read another word of those examples. This is fine.
It’s fine to stick your head in the sand and pretend laws don’t exist. But not if you want to make creative work for a living.
7. Do you know what your value is?
And no, I don’t mean “I am a person so therefore I am valuable.” (Although that is true).
What is your unique value to the marketplace?
Here are some hints:
Not your value: “I charge $70 per hour”
Not your value: “I make great videos with Premier Pro”
Maybe your value: “I help companies market to their customers through video”
8. Are you willing to be stubborn?
When people tell you your goals are impossible?
When you overcommit and have to do the work anyway?
When a task takes approximately 6 hours and 43 minutes longer than you thought?
When you have to hire and fire and rehire and refire until you get the right person in the right role?
9. Are you willing to re-invent yourself?
Before WWII, Jimmy Stewart played a syrupy lover in Born to Dance.
(“Hey babe, Hi babe, why not give me a try babe? Cuz I’m nuts about you!”)
After WWII, Stewart came back and made It’s a Wonderful Life.
(“I suppose it would have been better if I’d never been born at all”)
Okay, it’s unfair for me to compare lines out of context. How about a quote from Stewart himself after returning from war and screening his 1930s movies:
“Born to Dance made me want to vomit. I knew I had to toughen up.”
Stewart is one of the few actors who was able to make a hard left turn and continue to make money.
If you want to make creative work for a living, it will require some loss of naivety. It will require you to toughen up.
It will require you to become a new person.
Can you handle it?
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