Dealing with Disappointment as a Freelance Writer

I opened my email on a Tuesday afternoon and was blindsided by an email from one of my biggest clients: “We’ve decided to pause the project for now.”

It was a client I’d been working with for months. We’d done strategy calls, planning, the whole thing. We were this close to launching. A launch that would have carried my business for a whole year. And just like that, it was over. 

I can still remember exactly how I felt, and I’m having a bit of a flashback writing this. I know I sat there staring at my screen for a good five minutes. I was sick to my stomach, anxious about the loss of expected income, and I wasn’t sure if I was going to cry or scream. I’d had a few months of hit after hit, both in my business and personally, and I honestly wasn’t sure I could keep going.

Have you ever dealt with that mix of frustration, self-doubt, and extreme anxiety? I think most of us have at one time or another.

What I didn’t do was let myself spiral into “what if I’d done this differently” for three days straight. I did give myself one day, because I think we need to allow ourselves to be human and feel human feelings. But I learned long ago that starting a shame spiral when things go wrong is the wrong thing to do. Instead, I put on my own oxygen mask first (thank you to every airline safety talk ever), and then I got proactive.

Disappointment is a guarantee when you’re running a business. It’s not if it happens, it’s when. The question is, are you going to absorb the hit and stay stuck or keep moving and building your business?

The Disappointment Tax

“Just stay positive.” “Everything happens for a reason.” Has anyone ever told you either of those when you’re struggling or you’ve suffered a loss? They mean well, and they’re usually trying to offer what support they can, but neither are really helpful in the moment.

Sometimes things just suck, and you’re allowed to feel that. But I do have a suggestion for those gut punch moments: give yourself a deadline.

You get to feel disappointed when something falls through, whether it’s a lost client, a project that got canceled, or a pitch that didn’t work out. That’s your right. It matters to you, and that’s good.

I allow myself to sit with that disappointment for a while. I wallow. I’ll cry angry tears in needed, stomp around, vent to a friend, or bundle myself in a blanket and veg with a feel-good movie.

But I don’t do it forever. I set a mental timer. I get to go all in on feeling bad about the thing for a while, but then I need to do something different. I like to use 24 hours for my mental timer. I’m almost always ready to move on after a good night’s sleep. I have clients who want a couple of days, or a weekend.

That’s it though! After that, it’s time to pull up your britches, take a deep breath, and start moving forward again.

Staying in disappointment mode doesn’t serve you, my friend. I speak from experience. It’s a tax on your time, energy, and momentum. The longer you pay it, the more expensive it gets.

Being Proactive

After my Tuesday afternoon email, I gave myself until Wednesday morning to wallow in self-pity. Then I flipped to a new page in my notebook and wrote down three questions:

What can I control right now?​

I couldn’t control that client’s decision. And I wasn’t the cause of it. It was a business decision, not a personal slight. What I could control was my follow-up, my outreach to other prospects, and how I spent the time I’d just gotten back.

What’s one small action I can take today?​

I reached out to two past clients I hadn’t talked to in a while just to check in. One of those conversations turned into a new project three weeks later.

What do I want to be true a month from now?​

I wanted to have replaced that income and felt more diversified. So I mapped out a plan: refresh my LinkedIn content, send a few targeted emails, and finally launch that offer I’d been sitting on.

None of this erased the disappointment. But it gave me something to do with it.

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The Friend-to-Self Conversation

Another thing I’ve noticed over the years is that we’re often terrible at talking to ourselves the way we’d talk to a friend.

If your friend called you and said, “I just lost a big client and I feel like a failure,” you wouldn’t say, “Yeah, you probably screwed it up.” You’d remind them of their wins. You’d help them see the bigger picture. You’d probably tell them to take a breath and make a plan.

So why don’t we do that for ourselves?

Next time something doesn’t go your way, try writing down what you’d say to a friend in your position. Then read it back to yourself. Out loud if you have to.

It works because the voice in your head when you’re disappointed is usually not your wisest one.

Moving Forward Without Moving On

I still think about that project sometimes. Not in a “what if” way, but more like it was part of my story. It taught me to build in more buffer when doing my business planning, to diversify my client base, and to not put all my hope in one outcome.

You don’t have to move on from disappointment like it never happened. You just have to keep moving forward in spite of it.

And that starts with the decision to be proactive instead of passive. Make the decision to:

• Ask better questions.
• Give yourself a deadline on wallowing

And most of all, treat yourself like someone you’re rooting for. Because you are.

What’s one thing that didn’t go your way recently, and what’s one action you could take in the next few weeks to increase your momentum? Hit reply and let me know. We promise to read every response!

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