Lessons From My Toughest Year In The Freelancing Business

The more I panicked, the harder it became to get back on track and bring in the assignments I needed.

By Natasha Khullar Relph

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Note from Natasha: I wrote this post in 2013, after a very rough year in the freelancing business. It was probably the hardest year of my professional life. I have recovered since then, but I wanted to share this post to show you how failure and defeat happens to all of us, and how each of us can find in ourselves ways to recover.

These are the lessons I learned during that year. And truly accepting them and fixing them has helped me reach a point where I subsequently walked away from a six-figure job because I was doing more with my business. 

I know you can do the same. This is how.

Exactly one year ago, I confidently told my husband he could quit his job if he wanted. I could support us. I had been working fewer than four hours a day and I was making more money than I ever had in all my years of full-time freelancing.

Plus, I finally had an agent I liked, and it was only a matter of time until the book I was writing would sell; there had been murmurs of interest already, I was told.

The Perfect Storm

My husband didn’t need telling twice. He quit his job. 

However, between rewriting my book three more times on the promise that it had interest, finishing the first half a novel, and coming up with three more different book ideas, the first quarter of my year passed by in a blur. Halfway through the year, the book dreams had gone sour, many of my freelancing clients had lost budgets or gone under, and because I had spent most of my time chasing the book dream, I hadn’t replaced those freelancing clients. I had dramatically fewer assignments than I needed.

My agent and I parted ways.

For the first time in 10 years of full-time freelancing, I was panicking. Of course, the more I panicked, the harder it became to get back on track, to kick ass, and to get the assignments I needed that would start paying the bills.

We started dipping into, and slowly depleting, our savings. Selling stories became difficult for the first time since I started freelancing. Our cash flow became horrendous. And I spent hours, days, weeks, beating myself up about putting my family in a position that I now felt incapable of getting them out of. My confidence was shot to hell. And the less confidence I had, the less chance I had of digging myself out of this hole.

It took a while and a lot of pep talks from my wonderful husband, but finally I’m back on track. I started taking on new clients and building a career in content marketing that looks like, given time, will do extremely well. In my journalism work, I’m building new relationships and bringing in new clients. I feel confident, re-energized, and ready to give it my all once again. I’ve held on to my book dreams and can’t wait to partner again with someone who can help make them happen.

Most importantly, I’m painfully aware of all the mistakes I made in my freelancing business and how not to fall into the same traps again.

Lessons Learned

Here’s what I learned from my most difficult year in the freelancing business and what you should do to avoid making the same mistakes.

1. “Made X” is not the same as “paid X”

If there’s one thing freelancers should be taught on the very first day they quit their jobs to start a freelancing career, it’s the importance of cash flow. Especially if they’re going to be feeding their families off their freelancing incomes.

For instance, I’m owed more than $5,000 right at this very moment, money that should have come in months ago. But that I’ve made this $5,000 does nothing to help me, to pay my rent, or count as income in my balance sheet until it actually arrives. I kept a tab on how much I was making—and it was sufficient on a monthly basis—but a lot of it wasn’t paid on time, which means that my cash flow suffered.

An easy solution would have been to negotiate quicker payment terms with some of my regulars and just ask that payments be made via Paypal or direct deposit instead of check (it takes my bank six weeks to clear an international check.)

2. Don’t put the dream ahead of the reality

What I should have done was to keep my freelancing part of my work as my day job and work on the book and associated activities on the side. But in order to get a good book deal, I needed to work on my platform, come up with marketing plans, and do a bunch of other stuff I was feeling pressured to do. This meant that I did the opposite—I spent a lot of time on book-related stuff and fewer and fewer hours on my freelancing business.

In hindsight, this was not very clever.

3. If you’re not keeping up, you’re falling behind

Part of the problem this year has been that my regular clients and editors have almost unanimously come back saying that budgets have either shrunk or completely disappeared. With publications that were paying me $1,000 a story now offering $200 a piece, it’s painfully clear that magazines and newspapers just aren’t a sustainable way to make a living.

This shouldn’t have come as a surprise.

I should have diversified and built passive income streams years ago—with short blog posts, web content, more trade publications, and even branded content.

4. Keep yourself open to better opportunities

In the mess that has been my career this year, I did one thing right. In fact, the best thing I did throughout this whole ordeal was the most counter-intuitive one: I turned down a $15,000 ghostwriting deal.

This happened before desperation had set in and we still had plenty of savings. I’m grateful that I had the good sense to do so because had I taken that gig, I would have spent months traveling and working on this book at the expense of everything else I’m now doing, including my business, my books, and the new direction I’m taking my freelancing. ($15,000 over six months is not a lot of money, especially since I know this book could not have been written on the side.)

By turning down that $15,000 in the short term (and struggling for months because of it), I truly feel I’ve now put myself in a position to really grow my income next year. In fact, I’ve vowed to work towards making six figures a year and I’m putting everything into place to make sure that happens.

When you’re really struggling, it’s so easy to take low-paying, crappy jobs. You have to keep the faith that something better will come along. It almost always does. (And if it doesn’t, you can always find another low-paying, crappy gig.)

5. Don’t live in denial

Many freelancers just don’t run numbers enough. And when we do and don’t like them, we avoid facing facts. For instance, I’m a person who always pays her bills the moment they arrive, but there were a couple of months this year when I let the bills lie on my desk unopened.

Stupid, stupid, stupid.

I ended up paying late fees a few times, something I’ve never done in my entire life! I won’t tell you to open those bills, because that’s obvious. I know it can be overwhelming. But I will tell you that you’ll be better off for having done it.

6. Try harder before you get into trouble

Everyone takes desperate measures when they’re in serious trouble. I was surprised by how quickly I could drum up work (and cash) once I realized the desperation wasn’t going to set in three weeks from now; it was here, right at our doorstep, ringing the bell while we locked the doors and covered our ears.

So I took extraordinary measures and got work.

What had been stopping me from doing all the intense marketing, asking for help, and trying new things before things got out of hand? Nothing. Not doing it and allowing myself to get into a position of desperation was a big mistake.

7. Ask for help

I’m not very good at asking for help. In fact, I downright suck at it. But you know, I swallowed my pride one evening and posted on a message board for writers about how I was really struggling and that I needed help, any help, that anyone could offer. I got dozens of responses, referrals, and words of wisdom.

A week later, after having read through all that fantastic advice, my husband and I made notes, did lots of research, and launched ahead into the content marketing world. This now makes up a large part of my income.

8. Treat it like a freelancing business

Until this year, when I’ve said treat your freelancing like a business, I’ve meant asking for the best rates, working with clients who treat you well, and making sure you’re being professional and timely.

But this year, I’ve also realized that you have to invest in yourself and your business. I spent a lot of time learning new skills this year. I also asked my editors straight up how we could make it easier for me to get paid, since the checks they send take a month to be delivered and then six weeks for my bank to cash. One of my editors suggested Paypal, another swallowed the fee for a bank transfer.

Being a business means taking a tough stand. I have a 50% advance payment clause with small business clients that is non-negotiable. I told a magazine editor that my terms were payment within 30 days of submission and he changed the contract without question.

Saying “treat it like a business” is one thing, but truly treating your writing like a business means thinking of money and being smart about it. Money has never been the only thing I think about in my freelancing, but this year has been an important reminder that this is how I pay my bills. In order to do so, I have to ensure I’m getting paid in a timely manner. It means that I, not a random editor, have to set the rules of my business.

We’ve had a few setbacks this year. We’re slowly putting things back where they belong and making sensible and grown-up long-term plans, with contingency clauses.

It’s exciting and freeing, in a way. I’ve discovered hidden corners of freelancing that I’m perfect for, but that had never considered. I had seven client phone calls last week, already had a business meeting this week, and have four more phone calls scheduled for the next few days.

I’m looking at my freelancing today, not as an experienced journalist, but with the awe and wonder of someone who’s just discovered a myriad of different opportunities. 2013 has been a difficult year, but it’s set the stage for 2014. And I’m convinced that next year is going to be my best year yet.

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