What I Learned in My First Year of Freelancing

I had one goal when I started working on my freelance copywriting business full-time:

Stay married.


I don’t mean it to sound like my wife was unsupportive of the idea. She just is not a huge fan of the unknown, which we all know the freelance life has in spades.

Plenty of people make measurable goals for their first year in freelance, but I haven’t heard of a goal quite a measurable as that one. I’m either successfully thriving or paying alimony. That’s measurable.

Intrinsically, if I’m still married in this lifestyle, it means that other things are happening that might serve as goals to other people. Obviously, enough money must be coming in. In addition, I must be happy with the lifestyle in order to be bringing value into our relationship. People who are depressed because they haven’t left the house in a week tend not to stay married, either.

I met my goal. In fact, our relationship is better than ever.

There are plenty of books about how to embrace the freelance life, how to set up a freelance business, and how to grow your business once you do, like The Wealthy Freelancer, The Freelancer’s Bible, and The Well-Fed Writer. The problem is that books like that are often too good at their jobs: they flooded me with so many tips and tricks that I couldn’t possibly investigate all of them.

So what really worked? I’m glad you asked, considering that’s what I promised in the title of this post.


Freelancers tend to start out as generalists, afraid to turn down anyone that wants to give them money. That’s why it’s possible for people to make a living from sites like ODesk and Elance. Although being flexible is obviously a great skill to have in freelancing, I found that specializing in one market or vertical solves many problems that can come up in a freelance business.

I chose to specialize in companies looking to do business in the education market, due to my background as a teacher. Not only did I find a thriving market of potential clients, but I also saved myself a lot of time. My marketing is limited to a couple of LinkedIn groups that my decision makers frequent. If I want to go “press the flesh”, I have my pick of conferences where my clients and targets will be presenting. When you have a narrow focus, you can spend your time on more important things, like billable work. You also don’t have to worry about the local economy and the businesses around you.

Guard your time


We all got into freelance work for one reason: to control our own destiny. But too often I hear of freelancers answering e-mails at all hours, working 80-hour weeks, and never having a weekend.

If I had let myself fall into those traps, I would have definitely not met my marriage goal. All of the books I mentioned told me to keep work time and family time separated, and I’m proud that I’ve been able to follow through.

A client will try to test your response time very early in the relationship. No matter how long you’ve been working with them, if they call or e-mail after business hours (my time zone, not theirs), I let it sit and dealt with their issue the next day. Guess what? I never lost a client because of it. They simply got the hint that I was out of the office at that time, even though my office is the living room and I was technically “in”.

Get out!

I’m very happy being alone most of the time, which is why the freelance life is great for me. However, early in the last year, I let myself slide into a slight depression because the only people I had had a conversation with for a week were my wife and three-year-old daughter. If you don’t know, a preschooler doesn’t really form opinions about politics or sports.

So I fixed it. I became active in my local Rotary club. I formed my own networking group of dads who worked from home. I started some new hobbies. In other words, outlets that I wouldn’t have had time for if it wasn’t for my flexible schedule. I’ve met many new people, instead of just the small group around the water cooler or in the teacher’s lounge when I was working, and have things to look forward to every week besides work and the occasional family activity.

Keep a nest egg in the business account

In my personal finances, I’m not much of a saver. But with my business account, I always like to keep a fair amount in reserve. It may not be the six months of income that some of the freelance books suggest, but it’s enough not to worry about the times where business is a little thin (which happen to everyone and don’t let them tell you otherwise).

Another reason to keep some cash on hand is to take advantage of short-term opportunities. For example, the Creative Freelancer Conference sent out some great discounts in the weeks leading up to the event, which made me look up the airfares to San Francisco and talk to my wife about leaving for a weekend. If I didn’t have the $1500 or so on hand, I would have never had the opportunity to participate in a great learning and networking experience. You never know, good or bad, what can happen in this freelance life.

Scott Sterling is a freelance writer and editor who focuses on marketing content – such as web content, white papers, and case studies – for educational companies and tutoring services. Before taking the leap, he was a teacher, insurance agent, and technical writer. He is based in St. Petersburg, FL and can be found at www.educationcopywriting.com or www.caregiverdad.com.

Images via Grand Velas Riviera Maya and kojotomoto


4 responses
  1. John Soares Avatar

    Scott, I heartily agree about specialization. I’ve also specialized in higher education, but I primarily write supplements for college textbooks (instructor’s manuals, test questions, lecture outlines, etc.). My specialty has paid the bills and much more for many years.

    It’s also important to have at least 3 months’ savings: freelance writing can definitely have periods of slow or no work.

  2. Shafiqul Alam Mridha Avatar
    Shafiqul Alam Mridha

    I need a job.

  3. Suzie Avatar

    This is a great article. I actually am refraining from putting my website here because this article has inspired me to revamp it – and especially to emphasize the areas I specialize in. Thanks for writing this! I am bookmarking this one! 🙂

    1. Noemi Tasarra-Twigg Avatar
      Noemi Tasarra-Twigg

      Happy to help!

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