Big IdeasBusiness Beyond Freelancing

Death of a freelancer, part 2

By 08/27/2014August 12th, 202235 Comments


Today, I bring you hope and a plan.

Before anyone goes all Willy Loman on me, I thought I better come out with part deux. (If you missed part 1, start there.)

I exposed 11 myths about the freelance life because too many people are wearing rose-tinted 3D glasses.

You know, the ones they hand out when you pay your admission price to the latest “Live the Dream” feature at your local theater (or your friendly neighborhood Internet marketer).

Everybody wants the lifestyle, for sure.

Money, time freedom, lifestyle freedom, travel, rewarding work, recognition, and a purpose in life.

The problem is, it’s not as easy as they make it out to be. “They” being anyone who sells you on the freelance dream without also telling you about the dark side.

I’ll keep this somewhat limited, because the full details would make for way too long of a blog post (and “they” tell me that no one reads super-long blog posts anymore).

Plus, this is all a lead-in to my upcoming book. But you knew that, right?

11 ways to overcome the dark side of freelancing

Challenge #1: It’s hard to make good money

Big Idea #1: Be your own client

While you’re learning the craft of copywriting, practicing on unsuspecting clients and getting paid modest amounts, use your new-found skills to build your own information marketing business.

Essentially, become a marketer who can write your own copy, not just a copywriter who helps marketers make a ton of money. Be your own client.

The combination of both can very well produce a six-figure income (after taxes, not before) within 3-5 years.

Challenge #2: Negative cash flow

Big Idea #2: Take whatever work you can get, and work like mad

Yes, I know this goes against the grain of positioning yourself as a successful freelancer who commands top rates.

If you can get the good clients right away who pay well, go for it.

Unfortunately, I see too many freelancers with big gaps in their schedules because they’re maintaining their integrity with minimum fee requirements.

Better to be booked solid with low-paying work (to start with, not forever) than sitting around practicing your writing for free. You can always adjust your rates upward once you’re fully booked.

Challenge #3: No perks

Big Idea #3: Set up a SEP IRA

I’m not a financial adviser, so please consult with one on this. Just know that you can put up to 25% of your self-employment compensation, up to $52,000 in 2014, into a Simplified Employee Pension.

Once you start making decent money, that adds up a whole lot faster than 401k contributions, which are limited to $17,500 in 2014.

I’m not even going to touch the idea of insurance here, but I have my own, very specific contrarian ideas on that. I’ll share those details with you in a private email soon, not here on my blog for all the world to see.

Challenge #4: Freelancers are a commodity

Big Idea #4: “Brand” yourself

This is a complex idea that I’ll flesh out in numerous posts and Google Hangouts for you. Suffice it to say, it starts with figuring out who you are, and it helps to have a good business name, domain name, tagline, and title.

Until you decide, use your name. “Steve Roller” is a brand in and of itself, and your name should be, too.

Challenge #5: Freedom is elusive, especially the first few years

Big Idea #5: See Big Idea #2

Not what you wanted to hear, was it? Yes, work your butt off your first few years. Nothing less will be enough.

Challenge #6: Programs and certifications don’t mean squat

Big Idea #6: Develop a “Polished Portfolio” with proven results

Nobody cares what certifications you have or what associations you belong to. You can buy any of those, with or without real talent.

Instead, put your effort into producing top-notch work, and leverage every piece in your portfolio (especially your “Showcase Piece”) into good projects and retainer agreements.

Challenge #7: Clients don’t respect the term “freelancer” anymore

Big Idea #7: Stop calling yourself a freelancer

Build your own business with your own unique brand (see Big Idea #4 above), even taking it a step further eventually and establishing an LLC or a C-corporation.

Long-term? Consider growing a business that can run without you, or that you can sell. Much more on this to come.

Challenge #8: The program-conference-more money cycle

Big Idea #8: Develop your own “program” or system 

Not to sell to other copywriters, but to carve out your own path and not look like everyone else who took the cookie-cutter approach.

Challenge #9: Playing “follow the follower” and not standing out

Big Idea #9: See Big Idea #8

Challenge #10: The conflict between writing for other copywriters or not

Big Idea #10: Set a goal to hire other copywriters yourself

Look, nothing wrong with writing for marketers who could easily write their own copy, but choose not to because it’s not as lucrative as marketing.

As long as you’re aware of it and you get good fees while you’re developing your skills, it’s a great way to learn the business and get paid.

Here’s what I’d suggest, though. While you’re writing for marketers (or other copywriters) learn from them. Study their businesses. Ask lots of questions. Partly so you can write good copy, and partly so you can eventually do what they’re doing.

It’s more fun and financially rewarding to own the business, market the products, and hire other copywriters than to be on the other side of the equation.

That’s why the Copywriter Café has changed direction, and is now about “Turning Big Ideas and Copywriting Skills into Profitable Businesses.”

Challenge #11: The laws of supply and demand are working against you

Big Idea #11: Don’t line up with all the other freelancers

Be something else. I don’t just mean calling yourself something else, although that’s a good start. “Independent Creative,” “Conversion Writer,” and “Creative Conversion Specialist” are three of mine.

Maybe create your own boutique agency. Partner with someone who has complementary skills. Offer your services to one company only as their “in-house” consultant.

In other words, get creative. Think. Do things differently than everyone else. Stand out. Let your “brand” shine, and shout it from the virtual mountain tops.

Again, my intention here wasn’t to give you all the answers.

First, I wanted to show you that the dream lifestyle of a freelancer is anything but. Second, that if you become a Big Idea thinker, you can overcome this dark side that too many freelancers languish on.

Come on over to the bright side. It’s a lot more fun and profitable.

Last thing. I could use your help.

Which two of these ideas would you like to see developed most for my book, Death of a Freelancer: 11 Big Ideas to Overcome the Dark Side of Freelancing? (I’ll flesh them all out, but will put priority on the ones you choose.)

Leave me your number one and two choices here. Thanks.


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 35 Comments

  • Christina says:

    Hi Steve,

    I’d love to see more on branding yourself and being your own client. These are two points that I’ve gradually grown to understand the importance of – and the difference is palpable. It’s an ongoing journey at any stage in a copywriter’s career, though. Hence, I’d love to read more on it in the book.


    • Steve Roller says:

      Thanks, Christina. I’m looking forward to delving into this more and helping writers figure it out. It’s not an easy concept to grasp, and it takes time, but once you do life gets a little easier.

  • Hermine says:

    Hey Steve, awesome series! I actually feel relieved to see the word “freelancer” go to the wayside – can’t say I’ve ever really cared for it much and I’d rather be an independent creative, or better yet – a change maker. That’s so much more my style.

    Anyway, I know you asked for two but there’s actually three that I’m interested in learning more about – branding yourself, being your own client and the polished portfolio.


  • Terri Scott says:

    Hi Steve,

    I appreciate your revelations. I’d going to recommend that you expand on points 2, and 5.

    I’m especially passionate about point 2, because the words need to be spoken. I know I felt guilty and confused about pitching clients that were easier to obtain (Yet paid less money). I was tired of being made to feel that I’m not a copywriter worth my salt, that I would be like those low-life content mill drones who beg for pennies per job.

    But here’s the thing: Working for lower pay doesn’t mean that we have to work for pennies. And, too many new copywriters are literally starved for work, because they don’t have the skills or the infrastructure to pitch the big accounts. So, they believe they’re not cut out for this type of work, they get discouraged, and they fail to live up to their potential.

    We both know of someone in the FB group who doesn’t really pitch the “big guys”, but they’ve developed a thriving copywriting business. And, they hire writers to work for them! They took the skills and the infrastructure they had, and they ran with it!

    Point number 5: People need to be brought down to earth and realize that this isn’t a career field for lazy, get-rick-quick people. It’s rough building a business while also working to pay bills, and managing life! It’s not easy becoming any sort of entrepreneur. It’s a challenge to one’s endurance, and their ego!

    So, people need to face the unpleasant realities of this field, and soberly count the costs. This endeavor CAN WORK, but it TAKES WORK!

    Bonus point to consider, point 3: More of us need to take better care of ourselves, regarding financial and health care planning. We need to learn how to do this for ourselves, since most of us expected an employer to take care of these issues, and we don’t know how.

    • Steve Roller says:

      Terri, I know more than a few people in the Cafe (who keep it fairly quiet) that take any work they can get, deliver quality work quickly, and make good money. I think it’s a good strategy!

      Thanks for following along here. I look forward to connecting soon.

    • Genise Caruso says:

      Hi Terri,

      Long time, girlfriend!!

      I had to comment, because I agree with what you’re saying. This is what I’ve basically been doing. I’m not going to get $500 for a resume and cover letter, because my target audience isn’t executives. I have a great deal of clients who are managers, all kinds of professionals, blue collar workers, and my largest clientele lately has been students.

      It’s hard, though, when you know you’re worth X dollars to price something at Y, solely because you know the student population simply doesn’t have the means to pay big bucks for any type of services. However, I do it, and the simple fact that I understand their needs gets me a lot of referrals and repeat business.

      Now, remember I offer a wide-range of writing services, some (How do I put this without making myself look awful?) that aren’t truly accepted or appropriate to advertise to the general public. Yet, the way I see it is these people are going to find someone to do this work one way or another, so I may as well be the one reaping the benefits of the $$$!

      I guess in a way I’ve had to put my personal feelings aside regarding certain ethical matters. I’ve tried talking myself into the fact that I’m not the one who is doing a bad thing, yet, I am the accomplice.

      When I was in school, I would never have considered paying someone to do this, yet, in my case, I didn’t have to, because mine were better than the others anyway!

      It’s amazing how many people are just freaked out by having to write a report or essay. I’ve read the work of these people, and there’s no doubt, they would have failed without my help. I call it help, because I’m drawing on their ideas, just putting them into comprehensible words. Along the line I’m also explaining to these clients what I’m doing, why and how they can, and by the time I’ve finished, some of these folks are actually able to write a clear, coherent paragraph, without crying.

      If anyone thinks people in our field, writing in any niche, are lazy, and this is a get-rich-quick business, send them to me, and I’ll straighten their butts out – fast! lol If we were all rolling in it, as a result of our writing, then there would be no need for networking, blogging, or anything else, because we’d be too busy spending out “riches” to sit and write silly comments.

      So, right on, girl…call me sometime!

  • Stephanie says:


    These are ALL great ideas!!! Since you’ve mentioned previously that you will be going over more about “branding” ourselves in future chats and posts, and we can hire Kat to help on Polished Portfolios, I’m gonna go with #1 -Be your own client, and #8 – Develop your own “program” or system. These two interest me the most. Thanks for sharing all of your “Big Ideas” and for being so honest with us about the world of copywriting! God bless you!

    • Steve Roller says:

      Those are definitely two I’m going to develop further, Stephanie. I’m in the process of building two side businesses (aside from the Cafe and my copywriting-for-clients business). As I experience success with these, I’ll share details. Thanks for your input.

  • AnnB says:

    Steve, I’ve really enjoyed these two articles. They reflect what I’ve seen and heard way too often.

    I’d like to see more about branding, and about hiring other copywriters (to help develop programs which would become passive income…..)
    Yes, that’s three, but tightly interwoven 😉

    Thanks, as always, for all your wonderful help to all the wonderful folks at the Cafe..


    • Steve Roller says:

      Thanks, Anne. You’re right, they are interwoven. 🙂 I’m working on all three myself, and sharing details with all of you in the Cafe as I experience success with them.

      Glad you’re along for the ride.

  • Dale says:

    Big ideas 1 and 8 hit home for me Steve. My problem, like most writers, is coming up with fresh ideas for info products.

    • Steve Roller says:

      #8 is a big one for me, and it’s one that so many copywriters overlook. There are so many ways to create programs or systems for clients that will help them do more business without your time. That equals passive income, of course, an easier way to get to the big money without just trading your time for dollars. Stay tuned as I roll some things out, Dale…

    • Steve Roller says:

      The branding is coming soon, Alan. Watch for an exclusive Chat on this soon (probably Sept 18). #1 is something I’m working on myself, in the early stages of development. My plan is to share details and experiences along the way as I start doing well with it.

  • Alan Steacy says:

    Hi Steve, I see #4 & #8 as game changers. I’d be most interested in your deeper dive into those two areas.

  • Kimi says:

    I’m with Christina, being your own client and branding yourself…something I know I want to do, need to do, and am trying to do, but could use some direction.

    Very helpful post, as usual. And I love the new direction you’re taking the Café. 🙂

  • Mark says:

    Hi Steve,

    Great post. Put me down for a second helping of big ideas #1 & # 11 (and a little numerology to stir things up too). Have a great Labor Day weekend. Later,

    • Steve Roller says:

      Thanks, Mark, and noted. I love discussing both those ideas, especially #11, which I think you’re the first to mention. Enjoy the holiday weekend, too!

  • Genise Caruso says:

    Again, one of the best articles I’ve read in a long time. Finally something that most of us can relate to, but have yet to put down into words.

    Surprisingly, some of the ideas to the myths I’m not even familiar with. (And, I thought I knew everything 🙂 I had no idea the term freelancer was so negative; and I’m trying to impress upon everyone that’s what I am.

    I would love to know more about #4 “Brand” yourself. It is something I’ve frequently heard, but never sure how to go about it. Fortunately, depending how you look at it, I have a very unique name, and believe I’m the only Genise Caruso in the country. I know this is something I could use to my advantage, yet I hesitate to push it real hard because I’m afraid every nut job will come out of the corners! I’ve experienced some of that and it’s pretty scary.

    I’m also intrigued by #8, Develop your own “program” or system. I’m not sure precisely what you mean by it, or more important, how to go about doing something like that. (I have considered standing on top of Park Bank in Verona, with a 5-piece band, and doing some type of erotic dance, while my business cards were raining down on everyone’s heads!) You have to admit it’s creative. (BTW, anyone who reads this, Steve and I live in the same town.)

    Now I’m not being funny, but are you essentially talking about doing something unique and innovative that no one else has done? Don’t worry I’m afraid of heights, so you won’t find me on top of the bank anytime soon!

    I guess when you put it all in a nutshell, the bottom line is how in the heck does one earn a decent living doing the bad word, and have a better quality life? I’d sure like to know the secret. I promise I
    won’t tell! 🙂 lol!

    Thanks so much,

    • Steve Roller says:

      Genise, lots of good questions here, and not enough to adequately address it all in a quick reply. Again, maybe we should meet for coffee soon and talk about it (as long as you don’t bring that 5-piece band).

      First of all, I would completely capitalize on your name! It’s unique, as you pointed out, and it sounds good. You could create the “Genise Caruso” brand, which is an involved process. Watch for the Sept 18 Coffee Chat with Steve & Kat where we’ll go in depth on this idea of branding.

      By the way, I don’t necessarily think “freelancer” is a bad term, I just think it’s a default term that most people have never really thought of. It does describe what we do, but not in an overly flattering way. Think about it. Has anyone ever lit up with enthusiasm at a cocktail party when you told them you were a freelancer!? The usual response (the one I used to always get) was “Oh.” Not the reaction we want from clients either, is it?

      I’m not saying embellish your title or your credentials, but let’s get creative with how we describe what we do for people!

      I didn’t describe #8 very well. Sorry about that. I’m referring first to the idea that you don’t need to endlessly buy other people’s copywriting programs or training or seminars in order to get out there and start making decent money. In fact, at a certain point, you could create your own informational product that you could sell to clients – an ebook, a program, a webinar, whatever. Something you create once, that fills a need and serves people, that doesn’t require you to create something new from scratch with each client.

      For example, if your target audience was small, independent restaurants, and you were trying to sell them ongoing marketing help. You could start with a little $79 program you sell each one called “How to Increase Your Average Check Size by 27% Next Month,” giving them tips on exactly how to do that. You could create a direct response letter, send it out to 1,000 independent restaurants at a cost of about $580.

      Let’s say you sell 20 of them (a 2% response rate). You generate $1,580, minus $580, for a profit of $1,000. Do that every week for a year and you’ve made a base of $52,000.

      But you also go back to each one that bought and sell them on your next bigger program for $487. Let’s say you sell 2% of the 1,000 who bought your $79 program on your $487 program. Now you’ve generated another $9,740 (20 times $487). And let’s say two of those people buy your really big program (a marketing system for doubling your restaurant business) at $5,000. You’ve now made $71,740 for the year, all from starting with a small report/program/system.

      It takes identifying who you are, what you’re good at, who you can serve, where there’s a demand, and getting creative with coming up with a solution. Not an overnight process, by any means, but something I believe can be learned and put into action for real results.

      Hope that helps a bit, Genise.

      • Genise Caruso says:

        Thanks Steve,

        I promise – no band!

        Cocktail party? I can’t remember the last time I was at a cocktail party, but it’s weird; when I mention I’m a freelance writer, people usually go, “oh, that’s really cool.” The part I personally don’t like is the entire term ‘freelance writer,’ because I think most people associate that with someone who writes stories or books. Saying I’m a technical writer and Certified Professional Resume Writer, takes too much breath, and I’ve learned there is a very big misconception over what a technical writer is, (I was misconconceived (lol) too) and CPRW again, isn’t something people readily understand.

        When I hear the word “freelancer,” I think of someone who is self-employed, typically working from a home-office, and peddling their goods or services. I never gave it much thought whether it had a bad or good connotation. Shoot, now you’ve given me something new to worry about!

        I agree, 100% that capitalizing on my name is a good way to go, but not sure how. When I established my business name, for some reason I was hell bent on using my initials in the title – GRC, “Golden Resume Creations.” Believe me, I had lists of “G,” “R,” and “C” words that I tried to put together, and nearly drove myself insane in the process. Now, I’m glad I settled on the name I did, because the majority of resume writing businesses start with the word “Resume,” so already I’ve got an edge.

        Last night my husband and I were watching a rerun of SNL, with Lady GaGa. In her first song she did a lot of ‘crotch holding,’ and so my husband made a comment about how she’s a Madonna wanna be. Personally, I think she’s better and smarter than Madonna, but started telling him about these two articles, and brought up the part about being a brand. I told him she is a brand, and a very good one. Who doesn’t know Lady GaGa? Not that I’m going to dress up in crazy costumes, because I don’t think it would do any good, in my case, ha ha, but I agree there is something with the Golden Resume Creations name of my own that can be capitalized on. Just what and how???

        I get what you’re saying about creating a “product,” I could sell, and actually have been working on something. I know nothing about publishing, but I suppose once I get to that part I’ll find out.

        Anyway, thanks for some really great ideas and points to think about. And yes, it is about time we met.


  • Andrea says:

    Hello Steven,

    right now I’m struggling with two ideas, and I was glad to find them in your list: one is #2 and the other is #4.

    I strongly agree with both, but in my head they go in opposite directions: how can I brand myself if I accept any writing job under the sun, and how can I understand what should go in my brand if I don’t try to have as many experiences as possible?

    I could really use some advice on how to conciliate the two.

    And… if I can get a bonus for a third one, I would say #8 too.

    • Steve Roller says:

      Andrea, good questions. I think part of it is that you don’t advertise the fact that you’re working for anybody and everybody. Keep that under wraps, and just do it to keep the cash flow going.

      Simultaneously, work on building your “brand,” showcasing the best work that you do (being very selective about what you reveal) and always cultivating the image and style that you desire, not that which you already have. You have to figure out where you’re going with your brand, where you’d ultimately like to end up, and work toward that. It’s a long process, and like I’ve said, most people aren’t willing to put in the time and effort to do it. That’s why we have so many cookie-cutter copywriters, because it takes time to do this brand thing right.

      Stay tuned for lots to come on all this, including a special Coffee Chat with Steve & Kat all about branding, on Sept 18.

  • I’d like to see more about #4 and #11, Steve, which are kind of related in my view. Even though I’m pretty solid in my branding (master marketing and copy sherpa), I can always use ways to enhance it. I’m still transitioning from being “freelance copywriter and web marketing strategist” (used to sound so impressive, now it’s meh) to the above title. It actually gets people talking!

    • Steve Roller says:

      I like it, Janice! “Sherpa” ties in well with your travel clients and has conjures up a good image. Our brands are a work in progress, but the core themes remain the same usually. By the way, I’ll be in touch soon on the question you emailed me. Thanks.

  • Troy says:

    Better late than never.

    I would have to say #s 4 and 8.

    I have a questionnaire to help with the branding part, but Part 1, hit too close to home. Even with the minor success I’ve had, I still don’t feel I’ve done an adequate job at branding myself.

    The big ideas sound really good in my head, but when I talk them out and write them down, I feel their too close to everyone else’s.

    Love #10, only because I am a recipient of it.

    • Steve Roller says:

      Troy, #4 takes a while, and #8 takes even longer, but if you can keep going until you get to that point, and make decent money in the process, you’ll also get to #10.

      Regarding your thoughts about sounding too close to everyone else’s, you might want to go on a media “fast.” Don’t read other people’s blogs or newsletters (well, except for this one, of course) for a few weeks or months. During this time work on your own deal, without the influence of others.

      Let me know if I can help in any way.

  • #8 and #11
    developing programs (and a brand) are essential to standing out and creating multiple steeams of revenue.

    Thanks for another great post Steve. I can’t wait to see what you (and we) accomplish 🙂

    • Steve Roller says:

      Looking forward to seeing where you take all of this, too, Jen! Our Big Breakthroughs coaching will start up as soon as I get back from Vermont. I’ll send details soon.

  • #9 and #11, Steve…

    Tracey Silla, High-Context Writer (Creative? CreatOR? Idealist? Optimist… High-Context Optimist…

    High-Context Communications
    Helping you find the words to make a difference…because we must. Just brainstorming again…)

  • #1 – Be your own client – I really like this idea! I decided to “hire myself” a few years ago and I’m slowly making progress on the goal.

    #8 – Develop your own “program” or system – I love the creativity involved in this idea.

    I can’t wait to read what you have to say about these and all the other Big Ideas!

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