Listen, I’m not here to talk you out of chasing your dream. Please, chase the hell out of your dream! But when I hear “Do What You Love and the Money Will Follow,” I have to call bullshit.

Love writing? Well, do it for a living and money will magically show up in your account. Yeah, that’s a hard no. The money will follow? Bitch please, frustration will follow. Poverty will follow. Alcoholism will follow.

Tell the world you want to be a writer and you’ll find a disproportionate number of people will actually encourage this pure madness. One or two may give you the money-will-follow proverb. But please, ignore them.

The money doesn’t follow you, you have to chase it. You have to dive-tackle it, and pin it to the fucking ground.

You’ll struggle. The Struggle is real. But the Struggle is also kind of amazing. Here’s what that looked like for me.

Catchy Title. Shitty Advice

My Own Ridiculous Expectations

Of course, not everyone struggles. Some writers succeed right out of the gate. These people are what other writers call “massive assholes.”

I had a semi-asshole start to my career. I began as a copywriter for an ad agency in my small town. I knew almost nothing, but they paid me almost nothing. I had enough to put food on my plate, rum in my Coke and pay the rent on time(ish).

After a year, I started to feel creatively itchy and wanted to freelance on the side. First, a friend helped me sell a story to a political magazine. I’ll never forget being on the phone with the editor when he said, “We’ll give you $800.00.”

“Sorry, whud?”

That was more money than I cleared in two weeks. Then, I sold another story for $400.00. Then two more for $1000 a piece. Suddenly I was sitting at my desk wondering why I was wasting my time on a 9-5.

“I’ll go fully freelance. I’ll knock out a few of these a week, move to the big city, and spend the summer writing from a log cabin. It’s gonna be sick.”

Oh, Young Ryan… You stupid, silly, tit.

“Or… You Could Apply to The Home Depot”

I quit my job and moved to a bigger city. I had some very supportive friends… and two parents who thought I’d lost my goddamn mind.

My dad was a bus driver and my mom was a nurse. They grew up with real people with real jobs, with literal names. Banker, baker, cabinet maker. But freelance writer? The hell’s this nonsense? Are you working for free? You’re leaving your job for that?

I remember being on the phone with my dad and him excitedly telling me to apply to the new Home Depot in town. Because, “Once you’re in there, you’re IN.” He wasn’t being unsupportive. He just legit had no idea what I did for a living. He just wanted stability for his son.

He said I should work in the paint department because I painted houses in college. Also, the stores use computers these days and I had worked “In Computers.”

If you used a computer at work, you were “In Computers” according to my old-school dad. “What does Ryan do? He’s in computers.” Well… I’m not, but fuck it.

“I hear you. But I think I’m gonna stick with this writing thing for a while.”

“Yeah… Or you could apply to The Home Depot. Think about it.”

“Love you, Dad.”

This guy gets it

Big Pond. Dumb Fish

OK, I left the security of my small hometown to become a freelance writer… Now what? Can I have the money now? How about that log cabin?

After selling a few stories, my plan was to work for Magazine A this week, Magazine B next week. Who knows, maybe Rolling Stone after a year. Again, I was a silly tit.

My early freelance successes weren’t flukes, but they were definitely fortunate. Suddenly, my story pitches started getting rejected. The magazine income spigot dried right the fuck up.

“OK, I wasn’t prepared for this… Shit. Going to have to try something else. Or I could apply to The Home Depot.”

I wrote for newspapers, but that was barely rum-money. What else can I do? I started going to networking events hoping to meet entrepreneurs that needed a website or a press release written.

I didn’t know how to network. I had homemade business cards. I was bad at invoicing and often fucked up the math. One of my first clients said she liked me because I looked like a real writer, with my glasses and my wrinkled shirt.

“I actually did try to iron this shirt. Is it still wrinkled? Shit.”

But, I did Ok and I was happy. My business mentor convinced me that the only freedom was freelance. If I ever went back to 9-5, I’d be just another battery powering the Matrix.

But, then around 2008, the economy collapsed and my freelance clients could no longer afford to pay me.

So, back to the big machine I went. Back to 9-5.

My Return to the Matrix

After describing myself as a dynamic self-starter 10,000 times on 10,000 resumes, I landed a full-time gig in Toronto. I had to go back to office life and wearing pants during the day. Dammit all.

My income was now a “Wax On, Wax Off” mix of freelance and full-time paycheques. I really recommend this mix to young writers. Being fully freelance is fun and (sometimes) fruitful, but it’s also scary as hell.

Chasing freelance clients for your money starts to feel like chasing a coke-head roommate for their half of the rent.

Even when a company promises ungodly billable hours for a year or more, be wary. That magic carpet can suddenly disappear out from underneath you.

I once quit a full-time job on New Year’s Eve because an agency urgently needed my particular set of skills for a new client. Quitting was insane, but so was the offer.

I took the leap. I also took my first cheque, moved into a bigger apartment and started drinking a higher quality of rum.

But, a few weeks later, the head of the agency brought me into his office to tell me the client pulled out. And no client meant no Ryan. “We’ve got enough work to keep you busy for a year,” became, “We’re as shocked and as angry as you are.”

“OK, I wasn’t prepared for this… Shit.”

This is why after the word “Thirty” entered my age, I’ve been OK with 9-5 gigs (with a side hustle, of course). Freedom is good. But the exact same amount of money deposited in your bank every two weeks is also good.

But, Is The Struggle Worth it? Fuck Yes

I’m not a failed writer who’s telling you that the road is too hard. I’m a quasi-successful writer who wants you to know the road is not a road.

It’s a small path you have to machete your way through. You may struggle along the way. At times, your bills may be paid late and your relationships may be strained.

I’ll avoid any motivational quotes or proverbs. I hate those. I’ll simply say The Struggle is real, but it makes success so, so, so god damn satisfying.

The Struggle separates those who think they want to write from those with real fire. It’s the difference between entrepreneurs and wantrepreneurs. A writer friend put it well when he said, “Some want to work hard to make the team. Some just want the jersey.”

If you have any questions about how to become a writer, please, talk to someone far better than me. If they’re busy, you can contact me any time.

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