Big IdeasBusiness Beyond Freelancing

Freelance Myths Exposed

By 01/14/2016January 27th, 201658 Comments

Steve Roller at cafe

Freelancing is difficult.

Don’t let anyone tell you it’s not.

When someone tells you, “It’s easy,” “Anyone can do it,” or worse – “It will be fun,” they’re misleading you.

It’s not at all easy. Most people can’t do it. And it’s not fun until you start making serious money, which usually takes a few years (and some people never get there).

There’s a dark side of freelancing that no one likes to talk about.

Marketers selling you programs and systems designed to help you live the freelance lifestyle certainly don’t want to tell you about it.

If they did, it would put a dent in their sales.

Other freelancers don’t want to talk about the dark side of freelancing either. Why not? It’s embarrassing to admit that your chosen lifestyle isn’t working out like you planned.

The reason you hear the same freelance success stories trotted out over and over? Because they’re so rare.

And the ones that are legitimate?

There’s usually more to the story than they’re letting on.

From the Dark to the Light

So what is this Dark Side of Freelancing?

And if freelancing isn’t everything it’s cracked up to be, why are so many people ditching their jobs and jumping into self-employment and freelancing?

The Dark Side of Freelancing is reality. My reality, as someone who’s been a freelancer now for over 30 years. From 1986 to 2003 I was in direct sales, and I’ve been a copywriter since 2004.

I’m not making millions (yet), but I’ve carved out a very successful career in both sales and copywriting.

I’ve discovered the dark under-belly of freelancing, stumbled and fumbled my way through the challenges (with help from others), and emerged victorious.

I work on my terms, spend time with my wife and four kids, live in a nice neighborhood, and make decent money.

I also travel a lot, and bring my work. In fact, this blog post is the beginning of a book I’m writing while spending ten weeks in Quito, Ecuador.

Life is good, but not easy. You’ll have to work hard and work a lot to make it as a freelancer.

The Dark Side of Freelancing is also the reality of many other freelancers I know.

Writers, copywriters, content writers, graphic designers, website developers, entrepreneurs, travel writers, independent sales people, consultants, and coaches are all operating in this arena.

Are you ready to make your mark?

As founder of the Copywriter Cafe, an online group of thousands of writers, copywriters, and entrepreneurs, I’ve had the chance to counsel and coach over 400 people one-on-one since 2011.

A lot of them have gone on to big success. But you’d be amazed what people tell you in a private setting.

I won’t be using names in my book, but I’ll be describing situations so you know what you’re getting into (or are already immersed in).

More important, I’ll show you how to overcome the Dark Side of Freelancing.

That’s what this book is all about!

The book I’m writing (which I’m blogging, so you can read it chapter by chapter before it’s published) will give you answers if you…

  • Are tired of working for “the man”
  • Don’t fit into the corporate lifestyle
  • Want to be able to live life on your terms
  • Like the idea of working for yourself
  • Have a business of your own (or an idea for one) and want to make it more profitable
  • Realize that good, salaried jobs are going away
  • Have an independent streak and know that you’d rather not have a boss

In other words, if you want to work for yourself, build a business you can be proud of, and make good money in the process, you’re in the right place.

Over the coming weeks, in 21 quick, easy-to-read blog posts with easy-to-implement ideas you’re not hearing anywhere else, I will lay out a different way to approach the freelance lifestyle.

Follow along, keep an open mind to some contrarian ideas, take action, and you’ll overcome the Dark Side.

The 21 upcoming blog posts will form the basis of Death of a Freelancer: 11 Big Ideas to Overcome the Dark Side of Freelancing. You’ll get to read it before it’s published in book form soon.

Use it as a Guide Book for creating the freelance lifestyle you deserve. It’s there for the taking.

I’ll also be giving away some free copies of the physical book. Grab my special report to get those updates if you’re not already on my email list.

One last thing. I’m still looking for a few ideas and examples for the book. Do you have an interesting freelance story? Anything you wish someone would have told you starting out? I’d love to hear from you. Leave me a comment.

Steve Roller

Author Steve Roller

I'm a business coach, author, copywriter, world traveler (33 countries on five continents so far), and professional speaker. In addition to helping companies get more customers and make more money, I help other writers create profitable businesses. I offer one-on-one coaching, professional copy critiques, and live, in-person business-building workshops. When I'm not writing, coaching, or speaking, I enjoy nothing more than hanging out with my wife and four kids and planning my next adventure.

More posts by Steve Roller

Join the discussion 58 Comments

  • aliciajoy says:

    Great post, Steve. I totally agree. Freelancing can be hard and takes a lot of resilience.

    One thing I’ve learned is that you have to ramp up your discipline and focus muscles. Being your own boss is great in that you set your own hours and don’t have anyone watching over you. But those are also the factors that make freelancing so difficult in the beginning. Routine, discipline, and focus….none of these sound fun. But they work.

    Thank you for sharing this, Steve.

  • Steve, you asked the question, “What is one thing you wish you would have known before jumping into freelancing?”

    Actually, there are two…take your choice. I began down the path of copywriting doing my personal ‘research and due diligence’ at the 2015 AWAI Bootcamp. I listened attentively to presenters. I ‘interviewed’ ANYONE who had done this for awhile and been “successful”. This was in addition to intentional late night barside conversations…which included principals like Rebecca Matter. I asked pointed questions!

    NO ONE shared the LONG process to profitability if one is even fortunate to be amongst the few who DO achieve success. Also, NO ONE shared the rarity of success in this business and the frequency of failure.

    Yes, if I had known, I possibly would have chosen differently or cut the process earlier.

  • David Rosa says:

    Man, the dark side as certainly been a reality for me. For the past 4 years, it’s been real for me. The struggle I’ve endured should probably cripple the strongest giants in this freelance game.

    Wish I had a mentor back then to let me know how serious I had to take this business if I wanted to survive. Which answers the first wish.

    I absolutely know the possibilities in this industry, yet to wing it like I’ve been without someone guiding me has made it that much difficult.

    A lot of folks have an ego with this whole thing. They believe it can be done on their own and the richest and women come with open arms.

    Only if…

    This is a post, I wish was ingrained in my soul back when I was 22. But it’s something I am very aware of now and ready to make it happen on a much larger scale.

    Thanks, Steve

  • Scott Gese says:

    The one thing I wish I had known before jumping into freelancing is this…
    Some people tend to tell you things about this business that just aren’t true, well, at the very least, they tend to puff things up a bit.
    This is not a business where you can make it with a hop, skip and a jump. For me, this is a long slog.
    I’ve taken off the rose colored glasses I was given and I’ve ditched the Pollyanna attitude. I now know this is much harder than advertized.

  • Christa says:

    Hi, Steve,

    The thing I’d wanted to know before starting out was the fact that even though it “only takes a laptop and internet connectiom” to start your online business that there is another cost…”time”.

    Like most sales it’ll start gathering momentum if you can keep at it and focus.

    But it truly takes months to figure out the “what” even though the “how” is quite straight forward.

    You choose a market and a product seems simple enough, but which one to get that blurred picture in focus is time consuming.

    Then it costs money to get good copywriting training.

    It costs money to get a website going and it costs money to find a good coach, more time (money) to implement workable ideas and hours and hours of writing time to get really good.or good enough.

    In short, I’ve done sales and I understand running a business.

    I wish there was a much more realistic time/cost, pragmatic problem-solution, realistic list of what it really takes to start up a business that brings in sustainable income.

  • Mark Meador says:

    Timely topic … and one that is sure to earn you the scorn of established “goo-roos.”

    Quito’s eternal spring obviously agrees with you; your insight and words are as inspiring as ever.

    “Don’t quit your day job,” is the advice I most needed to hear back in ’97 when I went solo.

    The learning curve (stumbling and fumbling says it perfectly) is inherent in every venture. It’s a time of dark doubts, extreme frustration and zero income.

    In all honesty, it can take anywhere from six months to three years of full-time work equivalent before one figures the angles and starts to generate replacement income. And I would venture the majority of aspirants — with great talent and ideas — succumb to the fear and economic necessities and abandon their dreams during this stage.

    A much saner approach, one that ups the probability of sticking with it, is to let your daytime job (no matter how much you hate it) cover the “nut” while you sacrifice sleep and leisure time to learn how to build your business.

    The consequence, of course, is that it’ll take you longer to go solo (triple the normal time, perhaps, depending on how diligent you are).

    The upside, however, is when you do launch you’ll be one of those envied “overnight success” stories.

    Que te vayas bien, hermano!


    • Steve Roller says:

      Great advice, Mark. “Don’t quit your day job” is something everyone should hear. You’re right, six months to three years is probably about how long it takes most people to figure it out.

      And yes, Quito agrees with me well. Thanks.

  • Mele says:

    Great post Steve! I wish I knew to spend more time with like-minded people. Most of my friends are corporate types who thought I was crazy to struggle while trying to establish a freelance writing business. I would’ve learned that the struggle was NOT unique to me. I believed the “rah rah, it’s easy” stories and so I thought something was wrong with ME when the money didn’t come fast. I struggled with some serious self-esteem issues at one point.

  • Jonny says:

    Sometimes it feels like the struggle will go on forever, but 99 percent of it is internal.
    Fighting the fear, resistance, and rejection (often imagined) are challenges that I don’t think advice will help with. But it does help to hear from others who face the same challenges, even after they win.
    The best advice also comes from inside: Don’t quit.

    • Steve Roller says:

      Persistence is a huge part of it, that’s for sure. Glad we connected here in the Cafe, Jonny. You have a very interesting life over in South Korea. I’d like to find out more sometime, and help you wherever I can.

  • I’ve spent the better part of my adult life building businesses. Sometimes things went good; a lot of times things went bad (like Harry Nilsson’s song JOY). I don’t regret any business I ever started; I learned something from each. Any regrets I may have had concern the tremendous price in energy — both physical and psychic. But I always came back to trying to create something. I guess I still am. Hell, life’s an adventure. Let’s go out and get into some mischief.

    • Steve Roller says:

      Let’s get into some mischief, indeed, George! I like how you put that, “always came back to trying to create something.” I like the word “create” rather than the more common “build” when we’re talking about businesses.

      Can’t wait to see what you do with your latest idea.

  • Tom Emanuel says:

    I am very interested in your new book. Thanks for including me. I have one comment on what I read: You need a “so” in this sentence.

    “I won’t be using names in my book, but I’ll be describing situations that you know what you’re getting into (or are already immersed in).”

    Sorry, but I am a word-for-word reader.

    • Steve Roller says:

      Tom, thanks for catching that! I just fixed it. You weren’t one of the first seven to leave a comment to get a free book, but since you caught a mistake, if you email me with your physical address, I’ll send you a copy when it’s ready.

  • Thank you for writing about this important topic. Multiple streams of income is something you should definitely cover. We all know that we can’t labor 24/7. What’s the best way to leverage your expertise to create multiple income streams.

    Looking forward to the results!

    • Steve Roller says:

      Thanks for the feedback, Michelle. I plan to cover how to develop multiple streams of income, including passive income. A book is one way, if you market it right. I’ll be covering that, too. Stay tuned…

  • jer1986 says:

    Thank you Steve this is encouraging and I enjoy the real “no fluff” truth about freelancing. I’m looking forward to reading your book.

  • Jerry Bures says:

    To me, a wish after the fact is nothing more than a regret. And that’s something I’ve never been much inclined to do.

    “We must all suffer from one of two pains: the pain of discipline or the pain of regret. The difference is discipline weighs ounces while regret weighs tons.” – Jim Rohn, Motivational Coach

    Instead, I am reminded that…

    A new batch of Freshmen students race off to college every Fall with the understanding they will be spending tens of thousands of dollars and thousands of hours over the next four+ years to get a well-paying job in a field of their choosing.

    And yet, we hear all the time of the many who end up finding work in a field that has nothing to do with their studies.

    While I had hoped it would be easier…and quicker, I had decided to give myself at least 5 years to either figure this out, or see enough evidence that I would eventually succeed.

    It’s taken me six years, but I’ve recently been rewarded for my persistence.

    “Your persistence is a measure of your faith in yourself.” – Tony Robbins

    And I gotta say, it’s all about the ‘doing.’ And if I can do it, just about anyone can.

    “I will do today what others will not do, so that I can do tomorrow what others cannot do.” – Author unknown

    • Steve Roller says:


      You are a model case in persistence. Man, it’s exciting to see you see some success lately! I’m glad you stuck with it, and I have a feeling it’s going to exceed your wildest dreams in the next six years (or less).

      Keep me posted on things, and by all means, share your success stories with the Cafe if you’re comfortable with it (or I’ll do it for you).

  • chicfbdotcom says:

    Catching up on the emails and this resonates particularly. One of the most significant reasons I look up at you as a mentor is the “dirty truth”, there’s no “eyes folded in prosciutto” as the old Italian adage says.

    I am on the preparation stage of my ‘great escape’ that is my life after my daughter goes to college. I live in 2 opposite planets, the 9-5 and the independent woman entrepreneur wanna-be, they are two parallel tracks, I use engeneering of the mind to keep them separate, yet feed them, nurture them, make them grow. I play ‘as if’, like the Merlin principle, I rehearse pretending it’s reality, trying not to letthe fear of the unknown take over.

    My perspective is divergent from my other fellow colleagues here. The one thing I would like to know before jumping is how I will still balance freedom and discipline.

    Looking forward to reading your book.

    • Steve Roller says:

      “No ‘eyes folded in prosciutto'”! I love that expression. I wouldn’t have expected anything less from you, Francesca.

      I know from talking to you that you are living in these two worlds, and will make the break soon when your daughter goes off to school. Keep building your business slowly until then so it’s a smooth transition. I’ll do whatever I can to help.

      You’re right, it’s always a balance then between freedom and discipline. One of the things freelancers don’t talk about much is how hard it is to discipline yourself when no one is holding you accountable. More about that in my book, of course. 🙂

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