Why Hating Your Day Job Won’t Make You a Successful Freelance Writer

I hear every week from aspiring freelance writers who despise their cubicle life. You hate your boss. Working for the Man is unfilling. It’s boring. Certainly not how you ever planned to spend your precious days.

So you’re thinking about quitting to become a freelance writer. Maybe you’ve been writing on the side in hopes of building up your freelancing until it’s time to quit. Or perhaps you’ve recently taken the plunge.

If you’ve been in Corporate America a long time, here’s my forecast: You’re in for a rocky ride.

There’s a popular myth that if you hate being a cog in a big corporate wheel, it’s a sign that you should quit your job. Your hatred of the paycheck world indicates you will be a super-successful freelance writer.

But in my experience mentoring thousands of writers, that ain’t necessarily so. Here’s why:

Welcome to a completely different world

Freelancing is not anything like holding down a day job. You’ve been working away for years, but what you’re doing is in no way preparing you to operate a solo freelance business.

A typical day job works like this:

1. You have one small, specialized area of responsibility
2. A boss tells you what to do and by when
3. If you’re tired or sick, you can warm a chair and keep getting paid
4. Unless you’re in the marketing department, you do no marketing
5. If you weren’t in legal, you don’t negotiate contracts
6. All the big decisions are made by professional managers
7. A million little things are also handled by others
8. All the equipment and supplies you need are provided for you
9. If you need information, you ask the research department
10. Watching expenses is not your problem
11. The profitability of the business isn’t within your control, and not a big concern

As a freelancer, all these things work in reverse. Because now, you’re not working for the Man. You ARE the Man:

1. You are responsible for every aspect of the business
2. There is no boss to tell you how to prioritize your work
3. Warming a chair earns you zero dollars
4. All the marketing is your responsibility
5. Negotiating and getting contracts signed is all on you
6. You make all the big decisions, without a pro management team
7. Every little thing must be handled by you, too
8. You must purchase or obtain all needed equipment and supplies
9. If you need information, you’ll have to go find it
10. Watching expenses is critical to your financial survival
11. The profitability of the business is paramount — or you don’t eat

Compare those two lists, and you can see that corporate employment leaves you lacking many vital freelancing skills.

The worker-drone passivity problem

What often happens to your brain in Corporate America is that your initiative-taking and leadership centers atropy. They’re never called on. You don’t come up with ideas and take action on them. It’s all spoon-fed to you.

What’s more, when the company makes some spectacular misstep, your main role is to accept it. If you aren’t enthusiastic about the merger or the new product, you’ll be sacked, right? You learn to be quiet and go with the flow.

This leads to big problems when you suddenly have to run your own show.

Is your Google broken?

Over and over, I hear from writers who attempted freelancing…and hit a wall that stopped them cold. You can see these writers haunting the LinkedIn forums, asking basic questions that two minutes of basic Google searching could solve, or a quick LinkedIn search.

Questions like:

“Does anyone know the email of the editor for Costco Connection? I can’t find it…” (It’s visible in the online edition, on the magazine’s masthead.)

“Can you help me find the marketing manager for the company I want to pitch?” (LinkedIn usually works, or checking the contact name on the company’s online press releases.)

This is learned helplessness in action. If the answer is not directly in front of your face, you start asking random people to provide the answer, even if you could easily find it yourself — if you took a little initiative. But that’s just not in your blood, after your days behind a corporate desk.

It’s fascinating to have writers ask me over and over for factoids they could get in under one minute from a Google search. I sometimes jokingly wonder if maybe their Google is broken, or somehow my Google is better than their Google.

But I know what it really is: an allergy to being a self-contained, functional entrepreneur that was learned in the belly of a corporation.

What freelancing requires

There are a few things that working a day job do give you that help in freelancing. The top quality, I’d say, is the ability to deal with difficult people. I don’t know anyone who’s spent substantial time in Corporate America who didn’t acquire that skill!

If you want to write copy for big companies, it helps to have lived in that world before. You know the lingo. You don’t freak out when they bring out their wireframes and task charts and ask you to collaborate in the cloud or take five different meetings about the same project.

But some of the things that made it hard for you to hold a job — a dislike of following orders, for instance — will likely also hurt you as a freelancer.

In freelancing, you don’t just have one boss. You have many. And you have to juggle all of their demands and personalities and foibles.

At the same time, you have to decide your course and steer your business alone, making endless decisions about how to market, where to spend money, which clients to take, and what to charge.

The winning mindset

It’s funny, but many people spend years working in corporations, then start freelancing, flounder around for years…and then finally, remark to me, “I just got it — I need to think of this like a business!”

All that time spent in business, and yet we imagine freelance writing is a purely creative endeavor that magically exists outside the realm of commerce.

If you want to succeed as a freelance writer, learn to be an entrepreneur. Hang out with small-business people you know. Instead of going to writer conferences, go to conferences about how to grow your business. That’s what I did, and it made all the difference.

You may know how to write, but freelancing is running a business. Acquire entrepreneurial skills, and you’ll have a huge advantage over most freelance writers.

What did you learn from day jobs that helps you as a writer? Leave a comment and tell us.