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‘Imposter syndrome led me into making one of the worst business decisions of my life’

The number one confidence killer in all bright sparks is imposter syndrome. And it’s only recently that I have realised that imposter syndrome led me into making one of the worst business decisions of my life: Selling my first business.

For years, I’ve been haunted by thoughts of ‘what if’…

  • What if I didn’t sell out?
  • What if I had taken the advice of those I trusted most?
  • What if I had trusted MYSELF?

Selling my business was a fatal blow to my confidence and triggered a crack in my self worth:

I’m a failure. I didn’t have what it takes to run a business.

To those outside looking in, it appeared as though I was making all the right moves when it came to my career. That I’d gotten ‘lucky’, and was reaping the benefits of having a large organisation acquire my boutique business.

And, I suppose, it was somewhat true.

But I carry a backpack full of lessons from my first foray into business.

For me to share those lessons with you, I need to go back to the beginning.


I loved everything about owning and running a business. The freedom. The creative control. The ability to choose to work with clients that I knew I could add value too and create impact with.

I’d felt like I had found my purpose.

I was two years into business when I was approached by a national agency who said they were interested in meeting with me. I remember being so chuffed at the time. “Wow, we are on the radar of this huge multinational? How cool!”

I went to the meeting with a literal pep in my step – I was positively beaming. I remember walking away from that meeting on a high thinking how lucky I was to be exposed to such inspirational people. I really liked the women at the helm, the brand, and what they stood for. I truly thought that the reason they were reaching out to a small start-up was to forge a professional connection.

Looking back, it was what those large companies refer to as a ‘chemistry meeting’.

Or, to put it more simply: to see if we vibe.

One day, the CEO floated an idea by me: Was I interested in merging my business with theirs?

Over the next few weeks, I was wined and dined as it was explained to me how it would work, and if I’m being honest, I’m sure they could smell the naiveness on me. I remember feeling at such odds and ends during this time; what was the right thing to do? I knew I loved running the business – but I also knew that I really didn’t understand the economics of scale and how to actually grow the business.

Imposter syndrome began creeping in.

Perhaps they were right. Perhaps I should get out while I was ‘on top’.

I’ll never forget one meeting we had that left me questioning everything I thought I knew.

They had reviewed our books and clearly stated that we would end up running at a loss if we kept going the way we were going. That we were ‘exposed’ legally from contracts to processes. Surely, they said, wouldn’t I prefer to see the business receive the support, the guidance, and the investment that it deserved?

And then came the sledgehammer: We’re moving into this market with or without you. We’d be your biggest competitor, so you’re either with us, or against us.

It was, to put it simply, a masterstroke on their behalf. Checkmate.

My fear of failing was uncovered, and I began to believe that my business would never thrive with me at the helm.

I started to believe the nasty thoughts that were creeping in: I didn’t have what it takes.

My hands shook as I signed ownership of the business over in one swift motion.

The ink wasn’t even dry when I began to unpack what had happened over the past few months. The sale didn’t just signify the end of my business. It killed a part of me. I’d forgotten who I was.

And it was all my fault.


Did they do anything wrong? No, they didn’t. It was just business. I get it. I harbour no bad feelings towards anyone that was a part of the deal.

Do I wish they were more honest? Yes, of course.

But perhaps the most important questions were the ones I needed to ask of myself:

  • Why hadn’t I backed myself?
  • Why didn’t I believe that I deserved success?

I buried the answers to those questions for years, but I can now say with certainty that I was a victim of imposter syndrome.

Once I did the inner work and admitted this to myself, it’s like I gained instant clarity. I picked myself up and realised that I shouldn’t be ashamed. I’d had a momentary lapse of self-belief and that I deserve to give myself a second chance.

I told myself that I’m a superstar, and that not only can I do this, but I deserve this.


If I had my time again, would I sell? It’s a great question. Because while it was the worst decision I could have made at the time, I wouldn’t be where I am today.  As cliche as that sounds, it’s true.

Nowadays, I’m proud to say I’m back in business and thriving. I’m much more resilient and respectful of myself than I’ve ever been.

And as for imposter syndrome? Well, I haven’t seen that bitch in years.


With 15 years experience in PR, Business Chicks member Kat Orchard is a publicist by trade, and owns creative communications agency KK&O, and online hub, Just Another Girl. After working with medium to large sized businesses across a myriad of communications projects within her agency, Kat noticed a gap for those who have side hustles, or are a small business that cannot yet afford the cost of an agency. And so Just Another Girl was born. Kat funnels her experience and knowledge, coupled with practical tips into her raw, and at times sarcastic, blog. She specialises in helping female business owners supercharge their words and electrify their PR by offering practical tips and tricks. Kat is also a loving mother to her three year old daughter, Poppy.

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