6 things I learned from my epic freelance fail

Several years ago I started a freelance writing business. I was at the tail end of a two-year hiatus and freelancing seemed like the perfect way to ease back into paid work and still be around when my kids came home from school. So I got myself an HST number, worked on this very website, hung out my shingle and waited for something to happen.

It didn’t! And that surprised me. After all, I had 20 years of great experience. I was a VP at 30. I co-founded a successful public relations agency. My network was full of influencers. I was an active industry volunteer. Lots of people owed me favours. At least I thought they did.

After two months of coffee meetings I finally got a gig. A friend of a friend was launching a web-based subscription service that promised to make life easier for busy parents. He needed someone to help with media relations. I didn’t want to do media relations; I wanted to write great content. But I thought it would kick-start my foundering business and build my confidence. In a 30-minute briefing, he explained his value proposition, we agreed on a price for my services and we were off to the races.

Two months later, I had been fired and replaced by another freelancer. I never saw a penny of my agreed-upon fee and I was gutted emotionally and professionally. It was the first time in my career that things hadn’t gone as planned. But it wasn’t a total loss. Here’s what I learned from my freelance fail:

  1. You have to believe it to sell it – Even though I was in the target audience, I didn’t believe in the service and I should have been honest about that. It wasn’t the first time I had pitched something I didn’t love but I would have done a better job if I believed in what I was selling.
  1. Run from clients who demand shock and awe – Or anyone who uses bombastic military phrases in a business context. My client said my news release needed more “shock and awe”. Unfortunately, his product was neither shocking nor awe-inspiring. I should probably have suggested we part ways at that point but I reluctantly added some hyperbole and soldiered on.
  1. Define what success looks like – And insist on payment even if you don’t achieve it. Despite my misgivings about the service, I worked hard to pitch it to editors and even convinced a highly respected personal finance journalist to mention it in his weekly column. But my client wanted front-page coverage and I had failed to manage his expectations so he decided not to pay me for my services.
  1. Do your own research – My client believed his product was revolutionary and, as an entrepreneur, he needed that level of passion. When I asked him about his competitors or any barriers to entry, he said there were none. And he truly believed that. My own research revealed the market was already saturated. Worse still, one of the media outlets I approached had its own similar service, which it offered for free. If I had known this beforehand, I likely would have turned down the opportunity.
  1. Know when to walk away – When my client refused to pay, I reduced my fee by half to accommodate his disappointment. At the time, the idea of not making anything at all seemed worse than preserving my dignity. But when he also refused to pay my discounted fee, I felt like a chump.
  1. Have money in the bank – You know that old adage about having six months’ salary set aside before you start a freelance business? Turns out it’s true. I started a freelance business because I needed to generate income right away. But that meant I didn’t have the luxury of building it up slowly over time and choosing the clients and the projects I really wanted.

My freelance failure was painful but, as with many awful experiences, it led me to a different place which turned out to be exactly where I needed to be. What lessons have you learned from your failures?


  1. Louise, what an awful experience! Thank you for sharing. I hope that you also took away from it these ideas:
    (1) Bill a portion of the work up front. Some freelancers I know don’t start work until they have a cheque in hand. Certainly by two months in, you should have received something.
    (2) Think about having a kill fee. This means if the project stalls or you disagree, the client still pays a portion.
    (3) Listen to your gut, it is usually paying way more attention to things that matter than your brain.

  2. Thanks for reading and sharing your tips Sue. I’ll keep them in mind the next time I dip my toe into the freelance world. The good news is I haven’t been scared off for good. I am inspired by the many successful freelancers I know, such as yourself.


  3. Very well written Louise 🙂

    Thanks for sharing your insights.

    One learning that I find helpful is to always “disarm the bomb before it goes off”. Meaning that if there’s an issue or concern, address it first. Only once it is resolved will your prospect/customer actually listen to what you’re saying. And by addressing the tough stuff first, you’ll also understand you best next step.

    1. Great point Cyrus. I think I was hoping that the bomb would fizzle out of its own accord. Lesson learned. They never do.

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