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Confession Corner: Business Owners Fess Up To Their Stupidest Mistakes

Mistakes are an essential part of learning, especially when you’re running a business. Whilst no one wants to do something stupid or costly, ultimately, errors can serve to make us more resilient – as long as you’re willing to brush it off and learn from the experience. It can also make you more inclined to try new things. There are many quotes from famous entrepreneurs who point to the importance of failure en route to success. 

Here 16 business owners share their top blunders with you. Some of them are laugh out loud funny and I know I can relate to a lot of them. 


Wrong priorities

“I can share a lot of mistakes as a business owner. A few are: 

  • Working on enhancing a product or service where I should’ve focused on customer development instead.
  • ‘Sexy Shiny New Object Syndrome’ for tools that were not necessary at the beginning.
  • Not going niche enough.”

Carsten Pleiser – Design Buffs


Pyjama malfunctions

“Wearing my pyjamas (and bed hair) for an important, early morning client conference call and not realising my video was on the whole time. My humiliation didn’t stop there either. I got up to close my office door and, in the process, showed them the hole in my PJs at the back. That’s when they told me I was on their screens. The words, “We can all see you, Kia” will haunt me forever.”

Kia Cranwell


Wedding balls-up

“A fellow freelance designer whom I went to uni with had a wedding stationery project for a family friend and somehow ended up mixing up the starter and pudding on the menu. They didn’t realise until the big day when guests were reading ‘Sage & Onion Stuffing Balls’ as a dessert. Luckily for them, all the guests saw the funny side.”

Jonathan Minns


No one likes a break-up

“Trust your gut feeling, it is always right. I’ve stayed with a client too long on more than one occasion. My gut said walk away each time.”

Elizabeth Stanley


Bye-bye inheritance

“My two biggest mistakes were that I didn’t put a contract in place with a client I’d successfully worked with before (so thought it would all be fine) and got screwed out of £1,200. Also, paying a chunk of my inheritance money from my grandparents to a factory to make some handbags for me, hoping to start a brand from it. They sent me all faulty goods then stopped responding. I never saw that money again.”

Alex Pitt, Alex Pitt Creative


Taking on the big boys

“Spending two years developing software that would compete with industry giants hoping I could take just a small slice of their market share. Guess what, it didn’t, and I wasted lots of time and energy.”

Alan Fuller


Time is money

“I stayed with a client for too long last year. I’ve under-quoted time for work lately leaving me a bit out of pocket… actually a lot out of pocket.”

Anne Cholmondeley


Next stop: Copyright issues

“When I was first working in a design studio in the West End we created ranges of toiletries gift packaging for cartoon characters. One huge range was Thomas the Tank Engine. On the front of the sales brochure I was designing I decided he fitted in better if I reversed him. My boss went mad, Thomas has different bells and whistles on each side so the copyright was infringed and refused! We had to cover some of his bits in bubbles! I was saved but learnt a huge lesson!”

Angie Phillips


Social media skeletons

“Ranting on Facebook groups as many recruiters and business owners scour them.”

Oscar Heron

There’s no time to feel sorry for yourself in small business. So, when you make a mistake you need to take away the good from it, instead of dwelling on the bad. Find the lesson, learn from it, and walk away a smarter busienss owner. 

Andy Cordina Founder, Bettie Confetti

Time is money: part two

“My first job, I quoted for six hours, it took me 25. The fortunate thing was the client was so understanding and paid me for the 25 hours!”

Sharon Murray, Virtual Assistant at ConnectPA


Working for free

“I allowed myself to get totally scammed on a freelance website once, working for two weeks without realising I was never going to get paid for it.”

Kate Wellham


Wrong words

“I handed a client back his pen and said, “you better have that back, I’m a bit of a necrophiliac,” obviously I meant “kleptomaniac”! The worse bit was, he’s a will writer.” 

Catherine Gladwyn



“On one of my first IT jobs (24 years ago), I linked MS Access to the main system that ran the whole business. It accidentally pushed null data back into the system. The business shut down for two weeks whilst we reentered all data back in from printouts.”

Doug Hall, Mr H. IT Consultant, Wiltshire 


Keep your cards close

“When walking an old client through how to do something I accidentally mentioned a piece of software I used. They bought the software and I acted as an ad hoc consultant setting them up with it. For free. And it has slightly impacted on the amount of work that’s come through since. Don’t give away your secrets!”



Stick to what you know

“I’m a freelance exhibition stand designer and I learned never to take on something that you haven’t any experience in, such as stands with another floor above or an outdoor stand. This doesn’t mean you shouldn’t push yourself to try new things, but when it comes to doing a cost-effective job where they are paying for your experience, stick to what you know.

Also, always double-check emails and work before they are sent. In my case, I triple-check! And I always use Company Check or Companies House to check the financial basics of a company and set alerts for when a company goes bust. Thankfully I’ve only lost £80 in the past because I hadn’t seen soon enough to claim when a company had gone bust.”

Claire Litt Bell


The list goes on

“1. I sat through a meeting with a dinosaur plaster on my hand.
2. I met a client with baby vomit on my shoulder.
3. I signed a client email “love Em xxxx”.
4. I said “love you” at the end of a client call.
5. I spilt a drink on a client.
6. I misread the signals and thought a client was coming in for a hug (he wasn’t).

…I could go on. It’s amazing I have a business really.”

Emma Bail – Evolve Accounting



If it’s any consolation

Blockbuster passed up lots of opportunities to buy Netflix and in 1999 NASA made a simple maths miscalculation which cost them $125 million.

Every single person in business has made errors. It’s impossible to become a great person in business without making mistakes and learning from them. Henry Ford, Simon Cowell, Drayton Bird and Walt Disney are amongst the successful entrepreneurs who have bounced back from bankruptcy.

“The definition of insanity is doing the same thing over and over again and expecting a different result.”

Albert Einstein 

See every mistake as a way to progress. See it as if you have to make 100 mistakes before you reach your ultimate goals and every one made is another one out of the way. 

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Sophie Cross

Sophie Cross is a freelance writer and marketer specialising in business and travel. She is the editor for London Revealed magazine and her clients include Group and Merlin Entertainments.

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