A guide to the four favourite business f***-ups I've made

  • Opinion
  • June 18, 2019
  • Wendy Thompson
A guide to the four favourite business f***-ups I've made

Wendy Thompson is the founder and CEO of the successful social media marketing agency Socialites, and has 16 years digital marketing experience in some of New Zealand's top advertising agencies. However. that doesn't mean she hasn't made her fair share of mistakes in her career. Here, in her typically colourful way, she shares four mistakes she's learnt from all her years in business – and the important lessons she learnt from them. 


Inventor Thomas Edison is an expert on failure. He famously said "I have not failed. I've just found 10,000 ways that won't work".

We remember Edison for his revolutionary invention of the light bulb. But he actually filed 1,100 patents in his lifetime, in electronics, medicine and chemistry. The man never quit. And that's the same story of the inventors of our time: entrepreneurs, and they never quit.

Recently, I was asked to speak for MUV and Start Up Grind at TechWeek about my failures. I only had six minutes to speak so narrowed it down to just four fuck ups, although it's probably closer to 44 million. 

My amazing Dad taught me that managing 'failure' is all about attitude. That we need to reframe failure and f*** ups, large and small, and package them as learning experiences, all of which build resilience. What doesn't kill you makes you stronger, right?

Even now, they are cringe worthy, and make me feel so awkward to share. But all failures, 10 years down the track, make a great story later!

My favourite f*** up #1

All my failures were embarrassing but as I look on it now, this is easily one of my most embarrassing ones. It makes me cringe because of my naivety at the time and my major over-reaction.

Fashion houses Gucci and Chanel logos, visually, are not world's apart (above). They're both high-end, iconic brands and there is room for both to thrive. They're hot property for millennials and in 2019 are showing no signs of being put out to pasture. Which leads me to my story.

Around 15 years ago, when I was running a Pilates business in partnership, I was making it up as I went along, as you do. It was at a time before I had any proper business support or know-how and was pretty isolated. We'd just taken out a huge business loan and it took six months to finally break even with just enough money to live on. This was all whilst I had two young daughters. It was all a huge amount of effort.

But my true failing here was my identity became so caught up in my business. I was the business. It defined who I was.

Then one day I went to my car and there, tucked in under the windscreen wiper was a flyer for a new pilates studio just down the road. And the kicker was its logo was very similar to ours and the colours were nearly identical.

I felt like I was being attacked and was enraged. I become self-righteous and indignant, and immediately asked a lawyer friend of mine to send a cease and desist letter. Um, kind of an over-reaction, right?

I totally let this distract me from my focus and spent a lot of time and energy thinking about them instead of putting the attention on my business and clients.

I was so naive. Here's the absolute clanger... this new Pilates business had copyrighted their business and I hadn't!

[No alt text provided for this image]

By my turning attention to this business, I became distracted. I should have been focusing on my business and only on my business. I was also letting my being scared rule my decision-making and my anger came from a place of fear. I assumed that these two Pilates businesses – the pilates version of Gucci and Chanel – couldn't operate side by side.

But they could and they did.

My favourite f*** up #2

Jerry Maguire's client famously said:

“What you do have is my word. And it’s stronger than oak.”

And he meant it. For nearly 24 hours. Then the next day, he broke his word.

My version happened over a hand-shake agreement for a retainer with a very important client of mine – a client that consumed half my business. I'd sent them the contract – I wasn't stupid – but the months went on and they hadn't signed... hadn't signed... hadn't signed... And then I was stupid: I didn't make it a priority to get this done. I had been working with them for years, after all.

Then, as is inevitable is business, things changed. Procurement called me one day. It was a moody, grey winter's day that I'll never forget. They murmured words like 'budget cuts', 'cutting back', 'cancelled retainer' and '10 days notice'.

I at first felt betrayed, but then stupid. This was my fault. They had to do what they had to do. I was angry at myself.

My favourite f*** up #3

One of my business Socialites' core values is 'Excellence in Everything'. We like to focus on each value for a month at a time and see where we can improve. In this particular month I decided that we'd deliver our clients the very best monthly reports they'd ever seen or will ever see again.

And did we ever! They were beautiful. They were slick, sexy, and jam-packed full of insights and data. They had pretty graphs and thumb-stopping imagery. My team and I were so, so proud of them. Then we released them into the wild, into the hot little hands of our clients. And then....


After four weeks of feeling like I was living in an alternate universe with no response from any clients, I gave them a call. None of them had read my beautiful reports. Not. One.

Basically, all they wanted from us was bullet points and screenshots. All that time, energy and money came to nothing.

My favourite f*** up #4

This one is a doozy, especially for me who is both shy and works in technology.

Years ago, I was running a social media workshop in a mid-sized conference room talking about social media to a room of around 60 marriage celebrants. It was a tough crowd given some barely used a computer let alone were ready for the onslaught of social media. At the front of the room was a big screen. Like a really huge, gigantic screen.

And then: "Ding!"

A very personal Facebook message with a photo appeared in all its full colour, giant glory on this huge, ginormous screen. 

Cue Fawlty Towers comedic moment of me unplugging, replugging, manically deleting, turned off the screen, then turned it on, and it was still there! The room was in hysterics. Amid all the guffaws and laughter it was very definitely one of those 'I wish the ground opened up and swallowed me' moments.

Lesson learnt: If you're running a workshop about social media, or anything that involves a computer, create a dummy social media account to demonstrate on. And if you're speaking at a conference, shut everything down. No notifications, no nothing. Ever.

I also learned that people are very forgiving – I was invited back to run my workshop again the following year.Wendy Thompson, CEO & Founder, Socialites.

So that's my small list of f*** ups. I'd love you to share yours. All in all, everything I have ever done has led me to here, and I like being where I am. So whether you're riding through failure or success, it's all okay in the end.

This story originally appeared on Idealog.

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