The Dark Side of Freelancing: Here’s What No One Will Tell You

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For the past four years, I’ve worked as a writer, making a living through freelancing and my online business.

If you’re considering this path, you’ve probably read advice from dozens of sources on details like optimizing your email list, engaging followers on social media, reaching out to potential clients, making the most of your time when working from home and other nuggets of wisdom for success in the new economy.

What you don’t often hear from those of us doing this work is . . . how we actually make a living. Where does the money come from?

We’re not blatantly lying about our income. But we’re all kind of reluctant to admit when we can’t pay the bills from our solo businesses. So we just sort of omit other funding sources.

What We Will Tell You About Making Money

Over the years, I’ve made my living as a writer in a variety of ways. First, I focused mainly on writing for clients in areas like:

  • Freelance blogging.
  • Freelance journalism.
  • Manuscript editing.
  • Newsletter editing.
  • Web copywriting.
  • Web copyediting.

Then I moved into creating my own products and services as a solopreneur and making money through:

  • Ebook sales.
  • Coaching.
  • Online courses.
  • Webinars.

I’ve also built my blog audience up so that I can make money from:

  • Sponsored blog posts.
  • Affiliate sales.

Advice on starting an online business tends to focus on tips for success in these areas. But there’s a lot of luxury – free time, energy to spare, money to invest – assumed in that neat, clean path, and most of us don’t have it. Most of us take a much messier path.

What We Usually Won’t Tell You About Earning a Living

Building a full-time income as a freelancer takes time.

You have to establish your expertise, gather clients and build a reputation simply by doing the work for a while.

As a solopreneur, you have an even steeper hill to climb: building your own audience, developing your own products and never-ending self-promotion.

In the meantime, you still have to house and feed yourself and maybe a spouse, kids, pets and more. When freelance work has dried up, coaching clients stopped calling or self-promotion became tiresome, I still had to pay the bills!

To do that, I have:

  • Worked odd jobs like house-sitting, babysitting, dog-walking and house-painting.
  • Worked part-time as a barista (sort of a cliche for a writer, right?).
  • Split expenses with my boyfriend, or relied entirely on his income between clients.
  • Taken loans from my parents.
  • Relied on gifts from friends and family.
  • Lived with my parents, rent-free.

And I’m not the only one.

This work does not support me 100 percent, but I used to believe it should. I felt like a failure. Why was everyone else doing just fine striking off on their own, but I couldn’t make ends meet?

It was because of the income they weren’t talking about.

Many writers, coaches and other solopreneurs I meet are paying the bills with odd jobs and other financial support, just like I am.

And it’s OK!

It’s a grave disservice to new freelancers and solopreneurs to omit these alternative sources of income when we talk about launching lifestyle careers. We’re setting you up for failure by suggesting you ought to be able to support yourself entirely with your solo business, even early on.

Believing this myth was a huge detriment to my career as a writer, so I want to offer the advice I wish I had heard early on while I worked to make a living writing:

1. Keep Your Day Job as Long as Possible

I quit my job and tried to make a living freelancing way too early. This meant I was constantly struggling to keep my head above water, and I had to take on work I didn’t love just for the money.

I couldn’t focus on finding work that was right for me, because I just had to take whatever would pay.

2. Don’t Be Shy About Gifts, Loans and Support From Family and Friends

A $100 bill in a card from my sister when I moved out of state was the push I needed to invest in my first self-published ebook, which became the centerpiece for my brand.

Also, I forgo the whimsical stuff for Christmas and birthdays, and instead ask for gifts that support my work: an iPad, podcast equipment, gas cards for travel, etc.

3. Move Into Your Business One Step at a Time, Instead of in One Giant Leap

Oh, the leap sounds fun, I know. It sounds brave and exhilarating and admirable — and, sure, it is.

But it’s also reckless and a little miserable. I definitely wish I had eased out of traditional work and into working for myself in a few smarter stages.

Lifting the Financial Burden

In the past year, I’ve gone back to work, to the dreaded day job, to supplement my writing income.

It may seem like a shame now to punch a clock and work for someone else. But I’m easing the financial burden from my writing and giving myself the room I need to breathe and finally build a career I can truly love.

See Also >> 32 Ways to Earn an Income From Home

Dana Sitar is a writer and editor at The Penny Hoarder.