“Yeah, but at least there were doughnuts there.” And so begins this bit of advice for freelance writers.

Kyle Wong wrote about this thing called the Trough of Sorrow in an article for Forbes – and it’s really good advice for freelance writers, too.

We’re friends, you and I, right? And friends tell each other the truth (at least that’s what they kept saying in Stranger Things ). So, it’s time to talk about the Trough – just a little bit. You see, I’ve been there – and even visit again now and then.

If you’re an incurable optimist like me, when you start a new project, venture… or life, really – you go in kind of expecting some tough times at the start, but a steadily upward-sloping line of progress toward your goal.

Reality, of course, can look a lot different.

The path is a lot more likely to loop, scribble, and have jagged ups and downs. That this crazy, random-looking path is the norm among entrepreneurs was a HUGE shock to me, but also a comfort – and I hope you’ll remember this little talk someday when you need it.

Everyone braces themselves for the hard work of starting a business. You know you’ll have to stretch yourself beyond anything you’ve done before. As a freelance writer, that means learning how to run a business, how to get clients, how to make your portfolio, how to build a website, how to set prices, how to DO the projects those clients want – and more. But those are one-time learning curves, for the most part.

You see those challenges coming. You anticipate them, grit your teeth, and get a running start. WooHOO!! You cleared the hurdle.

Smooth sailing ahead, right?

Maybe. For a while.

Until you hit the Trough of Sorrow. Something happens. You lose a good client, deliver work that’s not your best, get stiffed, blow a deadline. You get sick – or your kid does. Your life goes haywire and you feel completely unhinged and derailed.

All of a sudden, you feel like your success path took such a steep dive that it’s off the bottom edge of the paper you were using to chart it. You feel like you’re scraping yourself off the ground 100 yards further back than your original starting point.

I promise: You will hit this point someday.


I wish I could protect you from it – and that’s one reason I email you, run the Facebook groups, and created the Working Writer, Happy Writer and Freelance Writers Bootcamp courses (quick reminder – you’re hearing from me because you are already enrolled in the WWHW course – let me know if you need help logging in).

But I can’t protect you from that Trough any more than I could keep my kids from falling off their bikes as they learned how to ride.

The best I can do is to let you know that it’s normal. It’s inevitable. You won’t stay stuck in the Trough forever. Either you’ll climb out one side and keep going – or you’ll fall out of the bottom and find something else that works better for you.

Freelancing is not for everyone. And for some, it’s not forever. There ARE perks to having a “real job” that sometimes outweigh the benefits of being out on your own.

Donuts, for example.

Advice for Freelance Writers

OK, maybe not the best example, but bear with me. When I worked in an accounting office, I knew some things for sure:

  • I’d get paid twice a month. There’d be a NICE bonus at Christmas, and another one at the end of tax season (because we worked 6-day weeks for months).
  • There was an endless supply of coffee.
  • Dave would be funny. Lori would have a funny story about her kids. Gladys would be mean. Jill would help me get over whatever Gladys said to me. Dianne would be a bit OCD. Hedy would have salad for lunch as we watched All My Children in the conference room. Jack would have a long, long lunch. Gordon would pour Skittles into a glass dish – a sound I could hear through a closed door. Dorothy would appear out of nowhere, like a ninja.
  • There would be donuts. Or, during the summer, one of the best crumb cakes you could even imagine (more than half its height was crumb!) – because Gordon would pick it up on the way back from the shore.

Sometimes, that level of certainty is what matters most. 

But not always. Sometimes, life allows us the luxury of forging out on our own. What we trade our security for is a whole set of freedoms that only come to the self-employed. There are pluses and minuses to every choice we make.

The quick rundown of freelancing perks:


OK, that’s the really short version. I don’t want to keep you too long today.

So, how do you brace for the Trough?

Here are a few provisions that I’ve found helpful on the multiple occasions when I’ve dipped into the Trough – and while I can’t prevent you from dipping in during your journey, I can help you prepare ahead of time so you land in as soft a spot as possible rather than slamming onto the rocks.

  1. As much as possible, build a little financial cushion. Desperate freelancers make bad decisions, repel clients, and suffer along the way.
  2. Develop a specialty. Might be a niche, might be a type of content. Having something you’re especially good at seems to surround you with a hedge of protection – at least a little.
  3. Connect with colleagues, mentors, and fellow entrepreneurs. Even the “hermitiest” among us needs this. Other writers are good to know, but so are other authors and other business owners. Just having someone you can check in with, someone who’s got your back, someone who’s been there – that’s a huge help when the waters get choppy.
  4. Make a habit of reading the kind of books that make you strongersmarter , and more skilled.

Well, there it is. Someone had to say it. Better that you know – so you can recognize the Trough for what it is rather than becoming bewildered by what’s befallen you.

When you find yourself in it, take a moment to catch your breath. Look for the lessons all around you. Then start climbing out. There are better days ahead – and you’ll be stronger by the time you reach them.

And have a donut. You’ll feel better.


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