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

Furious worker wants to quit day job.

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.

Freelance writing success

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50 comments on “Why Hating Your Day Job Won’t Make You a Successful Freelance Writer
  1. Bellaisa says:

    At my husband’s work, the ‘warming the chair’ point is an understatement. Many of his co-workers hardly ever sit in their chairs because they are too busy showing up late, taking a million breaks, or doing other non-work stuff that they get paid for.

    I think that someone who has the dedication to work even though they could get paid for doing nothing is someone who can make it in their own business, but those people are few and far between.
    Bellaisa recently posted…Subliminal Guru: Subliminal Messages That Are Subliminally Easy!My Profile

    • Carol Tice says:

      Some workplaces do seem to create a culture of work-shirking and avoidance. I never wanted to warm a chair at my day jobs — I wanted to work!

      When I was a secretary, if I was out of things to do I’d roam the halls, asking if anyone needed anything typed up. Probably an early sign that I was cut out for entrepreneurship more than corporate life. 😉

  2. Donyae says:

    The thing I learned from my day job that helped me as a freelancer was that I hated having a day job and if I wanted to live a life where I didn’t need one then I had to treat my writing like it was my job. Because it is.

    Writing is something I love but it’s still work and I have to treat it that way. Best job I ever had.
    Donyae recently posted…Why I’m Against Octavia E. Butler for the WFAMy Profile

  3. Mark says:

    I think people who have gotten comfortable being unproductive while working for someone else will have the most trouble transitioning into freelancing. It hurts when you realize what it’s like to have your own time wasted, rather than just a boss’s!
    Mark recently posted…Nothing Worse Than a Stagnant BlogMy Profile

    • Carol Tice says:

      It’s true — within every big organization lurks a decent number of people who’re complete deadwood. At one movie studio I worked at in my teens, one longtime company secretary watched TV 8 hours a day — no joke!

      People like this are in big trouble when they try to go freelance.

    • No wonder they hate their day jobs; nothing gets old so fast as being so lazy as to be useless.
      Katherine Swarts recently posted…Drowning in DutiesMy Profile

  4. Marco says:

    Hi Carol – Thank you for this powerful post and reminder. I’ve quit a job or two and almost always regretted it. The plan was to do some kind of freelance writing and/or PR and it just rarely panned out. In fact, we need to remember that “day jobs” are just that. Something we’re doing during the day to earn enough money to pay our bills and hopefully save a little. I always say you need to “earn” your way out of your job. That is, your side gig is getting so busy and lucrative that you don’t have time for your day job anymore. Until then, keep that day job!

    • Carol Tice says:

      Really? When I quit a day job, I usually had a party. I always felt certain it meant the door was now open for something better to happen.

      But your story illustrates what I’m talking about — when people quit day jobs with vague ideas of freelancing, no business background, and without the skills to market themselves, nothing happens. Then, you crawl over to the next day job and the cycle repeats.

      I know a few writers who were able to grow their freelancing on the side and then quit, but often it doesn’t work out that way. Sometimes, it’s just into the pool. Like I say…learn about running a solo business, if you want to succeed in freelancing. That’s key.

  5. “Learned helplessness in action.”

    Exactly what happens to so many after they leave their “real” jobs. It is also what happens to students after being force-fed year after year.

    • Carol Tice says:

      Oh, definitely ! Exact same syndrome. I’ve met so many hothouse flowers who’ve been in academia too long and don’t seem able to survive in the wild.

  6. Willi Morris says:

    Sometimes I think you’re reading my mind. I’ve been considering getting a day job. (Long story, will have to share privately) And I’ve been weighing the pros and cons in my head, but I haven’t written them down. You’ve managed to land a lot of these.
    Willi Morris recently posted…12 (More) Blogging Lessons After Year TwoMy Profile

  7. Lindsey says:

    Nice motivational read. I am a working freelancer, with a good handle on many of these skills and a total dislike of corporate desk jobs. I’ve tried too many to count. I am actively looking to increase my entrepreneurial skills and this was definitely helpful. I am starting to draw better boundaries now about what I will/will not do and it is really freeing!
    Lindsey recently posted…Novel Revision Strategy RoundupMy Profile

    • Carol Tice says:

      I think you can’t succeed in business without understanding ‘what business you’re in,’ as they say in The Cider House Rules. We can’t be all things to everybody. Or in my line of work, I like to say, “I can’t be the 24/7 global free Dear Abby of freelance writing.” We all have to define what we do to be helpful, and what we do for pay.

  8. This one really hit home. I’m struggling through multiple major transitions right now, and one of them is training my brain into the real freelancer success mindset. I suspect I’m not the only freelancer who spent too much time in the pipe dream of having the best (more accurately, ALL the good parts and ONLY the good parts) of both worlds: a place where *I* could choose what I did and when, but someone else would take responsibility for the big decisions and (especially) provide a guaranteed minimum income.

    Point #2 is especially significant; I have a tendency to try to do everything just in case I miss something, and even now that I’ve finally put roots to the habit of doing the most important things first EVERY work day, I still wind up in a frantic rush to finish “the list” at least as often as not.
    Katherine Swarts recently posted…Drowning in DutiesMy Profile

    • Carol Tice says:

      I think that’s more or less the deal I have on my Forbes blog, Katherine…but it only took 20+ years of writing my *ss off, 12 of them full-time as a staffer, to get there. Of course, it’s not a full-time living from that one client…but it is a thrill to have a client who trusts me implicitly, gives me a beat and the ‘publish’ button and just says “go for it.” And I do have some guaranteed pay, plus more for driving traffic.

  9. Great advice, as always, Carol. The things many of us dislike about the workplace will continue to challenge us as freelancers. Leaving the workplace to write full time requires a mindset change. We’re business operators who must be business partners with our clients.

  10. Pete Boyle says:

    Great article Carol,

    It really is a shock when you leave the world of the 9-5 and realise just exactly what is required to make your freelance endeavour a success. I’m still not there yet, but am starting to get a good handle on what’s needed and what can go wrong.

    I think the advice you give about finding a mentor is great. I didn’t have one myself but can only imagine how much time I would have saved and where I’d be now if I did. Ain’t hindsight wonderful!

    In my time at various companies I experienced a lot of what Kevin Carlton mentions in an above comment, employees putting their own individual needs above that of the company leading to a stagnation of whichever process is being undertaken. It is in fact one of the main reasons I left the corporate workplace. I was fed up of being let down by others as they didn’t think completing an assigned task was their responsibility or in their best interest.

    I’ve slowly eased in to the freelance life and, whilst there’s been more than a few hiccups on the way, I honestly do prefer it. As you say there is a lot more work to do with far more to consider, but it’s a challenge I readily accept and relish.

    Going it on your own is a daunting task, but can also be a great motivator. If I didn’t hit targets on a particular week when in a company it didn’t really matter, if I drop the ball as a freelancer the rent isn’t getting paid. It’s a scary thought, but one that forces me to take action. I have to be accountable for everything, if it’s not going well, I can’t blame anyone else.
    Whilst I’m definitely much happier (and busier!) in my freelance life, I’d give anything for paid holiday days!

    Thanks again for the thought provoking article Carol. I wish I’d been able to read this when first starting out.

  11. Carol, I started to feel more confident about my decision to quit my job and make writing my career, when I started saying, “I need to work on my business,” rather than “I need to work on my writing.” Saying these words helps me take it seriously. Even so, I find people are still looking me funny when I try to explain what I am doing. I think they think I just stay home and write poetry all day.
    Sharilee Swaity recently posted…3 Simple Organizing Secrets … from a Reformed SlobMy Profile

    • Carol Tice says:

      Right on, Sharilee!

      I’ve mentored many writers…and I seldom think the reason they’re not earning is that they don’t write well enough. But when I ask what they’re currently doing to market their writing *business,* too often the answer is, “Um, well, I’m really not doing any marketing right now.”

  12. Matt D. says:

    True, true. Freelancing is a business and it should be treated as such. Now, where are those like-minded people?

  13. Paul Acorn says:

    Dear Carol ,
    Many thanks for this article, which should be required reading for all newbies (including comments made by others). I can relate to many of these things from the days immediately after graduation (>25 years ago) when I started a business/self-employment and had no business experience and no mentor (and hence no well developed mindset although I had read about setting up a business) – made tonnes of expensive mistakes. It’s never easy to hear the truth or anything that could hurt the pride when you are good at the core business, but lousy at marketing. The business is like a 3-legged stool (core activity, marketing & finance) and if even just one of these is shaky then so will be the business.

  14. This article has been needed for quite some time.

    I was given a lot of freedom in my day job. Freedom to negotiate contracts, freedom to start and end projects with clients, and the freedom to be creative. But at the end of it, there was always the comfort that we were working as a team.

    In your own business, the buck stops with you. That was the biggest realisation when I went out alone. Even though I was alone, the tasks I had/have felt far bigger than anything I undertook in the corporate world.

    But that’s what makes it feel like exactly what I should be doing. It feeds my need for freedom. Pursuing this independence is what keeps me from returning to a world of comfort.

    Doesn’t mean I wouldn’t mind taking a paid sick day though 😉
    Razwana Wahid recently posted…Professional or amateur: You decideMy Profile

  15. Sune says:

    To this day, I still don’t think of blogging as a ‘real’ job. I’m definitely going to have to start changing my mindset on that one, I really think it could mean the difference between failure and success!

    Great post by the way!

  16. Cherese Cobb says:

    Steph, I did the same thing! I kept saying to my family that I needed to go get a “real” job–then I realized I had one. I just had to treat it like one. I love the idea of going to business conferences and hanging out with small business people! It’s time to click these terms into google!

  17. Carol

    One thing I remember from my days in a full-time job is just how many people put their own self-interests (and vanity) ahead of those of the company.

    You can sometimes sense this happening when you deal with certain organisations.

    Though I’ve never experienced this myself, perhaps an obvious example for writers is when you make an enquiry with a company about possible work.

    Now I’m guessing you want to avoid making an approach to the writers in an organisation. Because they could feel you’re stamping on their territory.

    And they’re probably not the decision makers anyway.
    Kevin Carlton recently posted…10 super simple strategies copywriters use to find a sizzling-hot USPMy Profile

  18. Emelia says:

    Oh, you got it so right Carol! There’s no such a thing as “I want to be my own boss” in the freelancing world. I do agree that it starts with thinking and doing things like an entrepreneur.

    • Carol Tice says:

      Well, in one sense you *are* your own boss, in that ultimately you can say yes or no to client nibbles you get. But in another sense, you are the servant of many masters, and have to juggle priorities in a way you didn’t in a single day job with one boss.

  19. Linzi Clark says:

    A valuable warning to would-be freelance writers like me who are still in the corporate world harbouring dreams of escape! This has been really helpful to learn before taking the plunge.
    Linzi Clark recently posted…Lunch break pumpkin artMy Profile

    • Carol Tice says:

      I think anyone considering this transition would do well to go down to their local SCORE office and get a mentor, or take classes in running a business. Will really pay off down the line!

  20. Thank you so much for the thoughtful post about the differences between corporate work and freelance writing. Even though corporations talk about taking initiative a lot, it is always within established bounds. I also really liked Michelle’s comment about learning how to take initiative instead of being told what to do. It’s really easy to fall into that trap.
    Lynn Lipinski recently posted…Fiction in a minute: Halloween RunMy Profile

  21. Lois Harris says:

    Funny, I just wrote blog about something like this. It was actually about my first year having my own freelance writing business…so I don’t have as much experience as some. I didn’t hate my old job, although it was getting a bit trying. I had wanted to be on my own for a few years. I think that if you have the right attitude, you can learn the new business, and un-learn the old ways of relying on others for some things. Also, I think it depends on how much independent thinking/researching/doing you had to do in your old job. With staff cutbacks and doing the work of three people, I actually learned from my old job that there is ALWAYS a way to get things done, even when it looks like it’s impossible. You just have to be determined. Which has helped in my business.

    Having said all that, you need way more motivation than ‘I hate my cubicle’ to get into this business. It’s hard work. But it is rewarding, there are people like Carol who can help you along, and the sense of satisfaction when you do get decent work and have time for what you really want is also a big booster. I’m not quite there yet, so here’s hoping.

    Cheers

  22. Michelle says:

    Thanks for this post! I can attest to how true that is. It took me about three years to understand not to completely function like an employee myself. I started out with the “tell me what to do so I can hide behind a computer” mindset. It’s something I still fight from time to time. I think that’s why content mills are a thing (gone down that dark road before). They put you into the “tell me what to write all the time” mode and on the surface make you feel taken care of, meanwhile you get raped for rates. Best thing I did was to branch out and study entrepreneurial topics. But at the same time, I learned a lot of what I know by working as a W-2 employee for a small business and taking directions, even if some of that is what not to do. 😉

    • Carol Tice says:

      That is ABSOLUTELY why content mills thrive. They step into that insecurity gap and present a way to at least appear to be earning as a writer without having to do much marketing…and writers jump at that. Years later, they can tell it’s never going to add up to enough money, but it’s such a hard habit to break because you have to move from passivity into action to run a well-paid freelance biz, get off Craigslist and Demand, and find quality clients.

  23. Steph Weber says:

    Yeah, I’m ashamed to say I’ve fallen into this trap a time or two myself. You must think of it like a business or you’ll get nowhere.

    At one point, I said to my husband, “Do you think I should go get a job?”

    And he was like, “You already HAVE a job!”

    My husband was treating this venture as a legit business, while I continued to see it as a side gig. That was the smack in the face that I needed! I have a business. Now, I need to treat it like one.
    Steph Weber recently posted…Ready to Hire a Freelance Writer? 3 Signs that Prove OtherwiseMy Profile

    • Carol Tice says:

      Good for your husband, Steph!

      I’ve always felt the fact that I was a *business* reporter and had talked to scores of startup CEOs was a huge advantage. I think on an unconscious level, I got it right away. “Oh. I’m starting a business now. I know what that’s like.”

  24. Marte Cliff says:

    Well said, Carol. I write primarily for real estate agents – marking materials, but also marketing advice via my blog and newsletter. Many of your observations about freelancing also apply to them, so I think I’ll write a spin-off.

    • Carol Tice says:

      Feel free — all kinds of solopreneurs grapple with these same issues. Though hopefully in the case of real estate, they can’t possibly go into it imagining they won’t have to be out there hustling up clients.

  25. Sabita says:

    Thank you for such a detailed article Carol. Awesome realization for anyone looking to dive into the freelancing world. In fact, many people consider becoming a writer an easy endeavor.

    And yes, I totally agree that the focus of many writers stay away from becoming an entrepreneur and learning to grow one’s business. On the contrary being one pays off for those who has the guts to be one’s own boss and keep going. 🙂

  26. Well, most of my writing is about the workplace, so I’ve learned PLENTY from my day jobs, lol! Also, I worked as a Director for many years, so I do have experience making decisions and providing input into the business.

    Still, I can’t say I particularly LIKE the business part of my business, although obviously I see it as a necessity. And it does feel mighty good when it works!

    All that said, I do agree with you, Carol, about the whole worker-drone thing. I’ve written lots about the dangers of corporate conformity. I’m working on a piece for my blog now titled “Chaos and Confusion, the Making of Sheep, and Apathy: Hallmarks of the Unhealthy Workplace.”
    Crystal Spraggins recently posted…Still Breathing …My Profile

    • Carol Tice says:

      I’ve written a lot on careers and employment, too — great way for us to leverage our knowledge!

      At first I wasn’t crazy about the whole business side, especially selling stuff to people, which I’d never done as a staff writer. But eventually, I learned to make a game of marketing and enjoy the thrill of the chase — and the high of landing a great client.

      • Lisa Columbia Snyder says:

        How do I get my first freelance writing job without a single clip?

        Many years ago, I earned a degree in journalism. I worked in publishing, then I took a decade off to raise a life: my daughter. Presently, I have a part-time job. I’d rather work full-time plus to become a freelance writer than seek another part-time job as, say, a barista. (Fine job, just not now, in mid-life, when I want to begin a freelance writing career.)

        I am determined to succeed. I am prepared to research, research, and more research.

        In other words, I’m in. I need help in the how.

  27. Really well said, Carol! I’ve had to explain this idea, that running your own business is actually RUNNING a BUSINESS, to so many people in the last year. Sure, I love the creative part of being a freelance writer more than anything, but it doesn’t even make up half of the time I spend working!
    Katharine Paljug recently posted…What’s the Secret to Getting More Done in a Day?My Profile

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  2. […] Why Hating Your Day Job Won’t Make You a Successful Freelance Writer | Carol Tice’s blog was one of the first I ever read and I’ve loved it (and her) ever since. Her tips are always insightful, and this post is right up there. If you want to start writing because you hate your day job, then you probably want to read this post.  […]