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The Frightening Facts About Being a Self-Employed Copywriter

Is the Copywriter-Entrepreneur Lifestyle Right for You?

The following questions were asked by a copywriter who is considering leaving his current full-time job to become a self-employed copywriter.  I’m sharing my response because it may help others considering the same option.

— Susan Greene


Dear Susan,

When you decided to become a full-time professional writer and go into business for yourself, were you scared?


Hi Josh,

That’s an interesting question. It was difficult to make the decision to go into business myself but not scary.  Going from a sure thing – a full time job – to something unknown was uncomfortable but not unthinkable.

I’d been planning it for a while, had some savings and also had already begun doing some freelance work on the side while employed full time.  In other words, I made sure I was prepared before giving my notice.

I had been working for nearly three years as an account executive at an advertising agency.  I’d gotten to do some copywriting but not as much as I’d liked.  I wasn’t crazy about the position and my boss was a difficult person.  I knew it was time to move on.  I believed that if freelancing didn’t work out, I’d be able to find another job.

Do you think being a self-employed copywriter is better than being a copywriter who’s employed by a company?

For me, yes.  But that’s something you need to decide for yourself.  You have to consider your mindset.  How important is it to you to have a steady paycheck?  Will you be able to sleep at night if you don’t know how much money you’ll have coming in?

How will you pay for your own health insurance?  For some people, not having benefits — like insurance, a retirement plan, and paid vacation days – is sufficiently scary to make them shy away from self-employment.

Another issue you have to consider is how you feel about selling.  If you’re not willing to do some marketing and sales work, you won’t be able to get clients. The work doesn’t come in by itself, as it does when you have an employer.  You’ll be the one solely responsible for going out and getting it.

Finally, being self-employed requires a certain amount of self-discipline.  You have to be motivated to work when there’s no boss or co-workers watching.

You may also find you have to work long days and weekends, if that’s what it takes to get a job done.  And you’ll likely need to be financially disciplined to avoid over-spending when you have no guaranteed paycheck coming in.

Personally, I didn’t like having a boss or even having a steady paycheck because I had no control over the amount. I was raised in a family of entrepreneurs. My father, brother and grandparents all owned businesses.  They weren’t wildly successful, but they made enough to raise their families and be self-employed their entire careers.  Most important, they loved their work.

My father, who owned a real estate company, couldn’t wait to wake up in the morning and get going on his work.  It provided him with a lot of happiness and self-satisfaction.  I knew I would be the same way.

When I began working at the ad agency, my plan was to learn as much as I could.  I knew I  would eventually be moving on to my own business, something writing related because that was what I loved most.  It was just a matter of time.

What would you recommend to someone who aspires to be a self-employed professional writer?

Plan ahead and transition gradually.  First, do you best to gain the skills you’ll need.  Second, you want to have some savings so that you don’t fall behind in your bills if your business doesn’t take off right away.  That may mean living on a tight budget.

Third, you should be doing some networking and some freelancing before you leave your full time job. That way you’ll already have some clients and potential work lined up.

What is the biggest mistake you see people make when they become full time freelancer writers?

They focus on the wrong things.  They set up their office.  They order business cards.  They launch a website.  They write a business plan and make financial forecasts.  But they don’t have a plan for getting customers, and without customers those forecasts are just pie in the sky.

Many people who’ve worked for an established business think work just magically comes in.  They assume that once they hang out their shingle, the clients will find them.

But that’s not reality for a new business.  You can be the most talented copywriter in the world, but you’ll starve if nobody knows it.  So figure out how you’re going to get your name out there and begin attracting clients and work.  That should be your #1 priority.

When you’re a new copywriter working on your own, do you ever worry that you won’t be able to do a copywriting assignment that comes in, that maybe you don’t have the skills or experience?

Yes, that happened when I was just starting out and it still happens today, decades later!

I worry that I won’t know what to write or that what I write won’t be clever. Or I think that the client will hate my copy or not think it’s worth what he’s paying.

I know that makes me sound terribly insecure, but I really do still have those internal conversations.  In the end I always find a way to get the project done and move onto the next one.

Now that I’ve been at this for many years, most new projects relate to or resemble something I’ve done in the past.  So I tell myself that the new project isn’t scary; it’s just like others I’ve completed successfully.

Then I force myself to get to work on it, usually by starting with the smallest, easiest, least intimidating section.  Once I break the project down into parts, it usually seems more doable.  Soon I gain momentum and the pieces start to fall into place.

What do you do when you hit a dry spell and don’t have work coming in?

I get out there and start hustling.  I go back to doing grassroots networking and cold calling to get work.  In all honesty, it’s been years since I’ve found myself in that position, but in the beginning it certainly wasn’t like that.  And when things got slow, I hustled.

I’ve also always made sure I lived beneath my means because I never wanted to feel panicked about money and have to get a 9 to 5 job working for someone.

My freedom is too important to me. So I’ve never driven an expensive car or bought expensive jewelry. I’m not into “stuff.”  I’ve certainly never tried to keep up with others in terms of material things. I make a respectable living,  I enjoy my work. I enjoy my life.  And that’s good enough for me.

I tell my kids, “It’s okay to be satisfied. You don’t have to always be looking for more or better. You can be happy with what you have, regardless of what others around you have.”

That probably sounds un-American, but there’s nothing wrong with appreciating your life and being fiscally responsible.

How do you get most of your business today, now that you’ve been a full time freelance writer for many years?

My current workload comes from the following 4 main sources:

  1. Existing clients with ongoing needs
  2. New clients who find me through Google
  3. Referrals from other professionals
  4. Subcontract jobs from ad/marketing agencies and web design firms.

By combining those sources, I keep pretty busy.

Are most of your clients local to you?

No, they’re not.  When I started out in business, pre-Internet (yes, I’m that old), my clients were all within a 50-mile radius of my office.  Most were obtained through networking at business groups, doing local public speaking engagements and getting referrals from personal contacts.

Nowadays, I work with clients all over the world, many of whom found me via a Google search.  Today, as a matter of fact, I just landed my first client from Abu Dhabi.  And I’ve done work for clients all over the world — England, Colombia, Hungary, Canada, Portugal, Qatar and Saudi Arabia, to name just a few of the countries from which they’ve come.

How do you stay motivated?  After all, you’re not working toward a promotion or a raise and nobody is keeping an eye on your productivity other than yourself.

I think, in part, that’s just my personality.  I am self-disciplined.  I get things done. I make things happen. I like the feeling of accomplishing something, of finishing a job I started and making sure it’s perfected to the best of my ability.

If you’re going to be in business for yourself, whether as a copywriter or any other profession, you definitely need to be self-disciplined and self-motivated.  You can’t succeed as an entrepreneur without those qualities.

How do you become a great copywriter?

Like any profession or skill, you have to work at it.  Even if you’ve been blessed with natural writing talent, you still have to practice if you want to excel.

I’d like to believe the more I write, the better I get in my profession.  When you invest 30-40 hours a week using your skills, you have to be improving, right?

Additionally, I do a lot of professional reading to continually find new approaches, get new ideas.  I’ve learned so much from other great copywriters.  I am humbled by their talent.

What is the most important advice you could give someone considering becoming a full-time, self-employed professional writer?

My #1 suggestion would be to make sure you love to write. Just because you got an A in Freshman English or because your grandma said she always enjoyed receiving your letters from summer camp doesn’t mean you should be a writer.  And editing someone else’s copy doesn’t make you a good writer.

Writing is hard work.  Essentially, you are making something out of nothing.  Creating isn’t everyone’s cup of tea.  If it feels like a chore to you, then you’re not cut out for the copywriter’s life.

For me, writing is what I’ve always been good at.  In fact, I can’t think of anything else that even comes close in terms of my skills.

I’ve been having a love affair with words since I learned to read at age 5.  I write every day, whether on client work or some personal writing task.  And nothing makes me feel more confident and accomplished than completing a writing assignment.

If you’re nodding your head “yes” because that sounds like you, then I’d say you’ve got a good start on a successful writing career.  Just remember, a true entrepreneur is a doer, not a dreamer.  So get to work!

Want more tips to grow your freelance copywriting business? Request my FREE Copywriter Report. Email Susan Greene at and put “Copywriter Report” in the subject line.

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Contact Susan Greene

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