What I Learned about Freelancing After Going Broke in 2013

Confession: I was totally broke in October 2013.

And I don’t mean broke in a figurative sense like I didn’t have much money.

I mean broke in a very literal sense in that I had less than zero dollars.

In September and October 2013, my consumer debt had ballooned up past $70K (again).

And I was getting hit with overdraft fees because money wasn’t coming in fast enough.

As soon as I deposited a client check, I would immediately allocate it to outstanding bills and I was back to near-zero.

I had seen this financial disaster coming in late 2012. And although I had tried hard to stop it, I had failed.

It was like being in a car wreck in slow motion.

I could see the wall approaching. I could anticipate the crunch of metal into concrete. And although I pumped the brakes, I couldn’t stop the car.

It was a complicated situation involving both loss of income and medical bills from the birth of my 4th child.

Back then I’d been writing a lot of copy for one particular client in the survival niche.

I’d written multiple long-form sales letters and dozens of advertorials. The future looked bright.

My client and I got along so well he even flew me out to his business in Illinois.

He picked me up from the airport, put me up in an old house he owned right next to his business, and introduced me to his employees.

He even introduced me to his family. We all had a few meals together. And one evening he took me out to his cabin right on the Mississippi.

We all went out on an evening boat ride — his wife, kids, and their spouses — then ate dinner together and had a great time.

By the end of the trip I really did feel like part of the family.

But something was about to happen that would totally destroy that business relationship.

In June 2012, about 11 months after my trip to Illinois, my client suddenly went radio silent on me.

He’d been sending me a significant amount of work every month. In fact, I would get a list of pieces to write at the beginning of every month.

The work had been so consistent, it was almost like a retainer (even though I billed by the piece). So I always kept space in my calendar for this one particular client.

Then one day he stopped sending me work. No notice. No explanation.

I called. I emailed. I even sent a handwritten letter asking him if I’d done something to offend him.

I never could make sense of why he cut me out of his business because I saw the weekly results and knew my copy was producing consistently.

Example: At the time I was charging him between $500 and $750 for a long form advertorial. I remember one of those advertorials produced $15,000 in revenue from just one email to his list.

Any winners I wrote for him would be mailed multiple times and get similar results with each mailing. I would not be surprised if he grossed $50,000+ just from that one email.

So why would he stop working with me without notice or explanation? Did he begrudge the $500 or $750 he was paying me?

I’ll tell you the answer to that question tomorrow…

But the reason I tell you this particular story is because I lost about $4,000 a month in steady copywriting income when this client disappeared.

And although I had other one-off projects coming in, I was not able to replace that income as quickly as I needed.

With medical bills piling up and credit card debts weighing me down, the loss of predictable income turned into a real personal financial crisis that reached its climax in October 2013.

So how did I get out of that situation?

Two things happened…

  1. My father-in-law had compassion on us and gave us a cash gift that provided some breathing room to get our finances in order.
  2. More importantly, I met the client who would put me on retainer and ultimately become my longest client relationship. We met in September 2013 and started working together in October.

By the beginning of 2014, I had built up my cash flow again and my business rocketed higher for three years straight.

As I reflected on that extremely difficult situation, I began to think about my best income years vs. the latter part of 2012 and and first nine months of 2013.

And that’s when it hit me…

During all my best years I’d had at least one retainer client and sometimes two.

But during my personal financial crisis of 2013, I’d had ZERO clients on retainer.

When you’ve got at least some stable income coming in each month, it washes out some of those valleys you may experience while waiting for a new client to sign a contract… or a current client to pay you the balance of a project.

Ever since that epiphany, I’ve been careful to have at least one retainer client at any given time, and preferably two or three.

This is one of the “secrets” of building a successful freelance business I wish I’d been consciously aware of prior to 2013.

And I hope that by sharing my own mistakes I can help you avoid the pain and humiliation I had to go through.

I’m rootin’ for ya,

Ryan “retainer clients” Healy

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Ryan Healy

Ryan Healy is a freelance copywriter, list manager, and the author of Speed Writing for Nonfiction Writers. Since 2002, he has worked with scores of clients, including Agora Financial, Lombardi Publishing, and Contrarian Profits. He writes a popular blog about copywriting, advertising, and business growth, has been featured in publications like Feed Front magazine, and has been published on sites like WordStream.com, SmallBizClub.com, and MarketingForSuccess.com.