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Wellbeing / Work styles

Confessions of a misfit entrepreneur

These days it seems everyone wants to be an entrepreneur. But do you really need a business plan and a sharp suit to get to the top? Kate Toon explains how she built three successful business in six years, and how you can do it too.

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When I started my business I had one simple goal—survival.

I wanted to leave the horrors of the boardroom behind, but still make enough money to live comfortably.

I honestly had no notion of entrepreneurialism – a word I still struggle to actually say out loud. And the truth is I never set out to be an entrepreneur.

But now I guess I am.


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Without wanting to toot my own horn, I’ve developed not one but three successful businesses. I’m making way more money than I ever did as an ad agency manager, and I’m earning it in far fewer hours. All in my PJs from a hut in my back garden.

And I have to be honest – a lot of it happened by happy accident rather than design. I’ve never followed the so-called rules of business. Most of the time I’ve either ignored or broken them.

And confidence? Judgement? Patience? Well, I don’t possess a whole lot of those ‘required’ business personality traits. Quite the opposite. In fact, most of the time I’m a big hot mess.

"I have to be honest and say a lot of it happened by happy accident rather than design"

So in this post I want to explain four ways in which I managed to build a successful business despite myself.

I’m not a planner

Most business coaches will tell you it’s vital to have a plan, or at the very least a vision. These important business tools will guide you through the tough times, and help you make clear decisions about what you should and shouldn’t be doing.

My vision was simple: Work at home and make money.

I didn’t map out the steps or set milestones. I didn’t keep myself accountable or measure myself against objectives. I just kept on keeping on.

That said, I have worked at home and made money. So maybe I did have a vision, but it just wasn’t ‘mood boardable’.

I get emotional

When I worked in the ‘real world’, bosses often told me I was too emotional. I was passionate and determined about my work. I was devastated at my mistakes. I rode that business rollercoaster clinging on with a white-knuckled grasp.

And try as I might to be a calm, centred being, I’m still emotional.

But now rather than quash it, I embrace it. I believe emotion breeds empathy, and empathy allows me to understand my customers better.

My emotional-ness helps me soothe their pain points, and deliver better products and services. I’ve been there. I get them. And they, in turn, get me.

So while I’m still riding the rollercoaster, at least now I get to choose my seat.

I rush into things

Along with not having a plan, I’m a huge fan of rashly rushing into projects and submitting to ‘shiny new object’ syndrome.

I don’t do A/B testing, run surveys or create a beta version for anything I do.

I just go live with it – pretty much immediately.

The ‘better done than perfect and undone’ mantra is something I live by.

This has led to some horrendous last-minute panics and some horribly late nights. But it also means my products and services are out there, in all their imperfect glory, earning me money.

And of course, I’m happy to admit my failures and not just cling to my mistakes because I took such a long time to make them. That helps.

I’m a little bit scruffy

Don’t be fooled by the profile pictures. I’m actually quite a scruffy beast.

And while I’ve tried to fight this, looking glam is not something that comes naturally to me.

I have zero interest in clothes, makeup or hair. And I can’t force myself to care.

For a long time this held me back from getting my face out there for my brand.

My insecurities whispered that unless I was 20 kilos lighter with bigger boobs and a glossy mane, no-one would take me seriously and no-one would buy from me.

It’s simply not true. My slightly frazzled appearance is rarely commented on. When it is, the comments are that it makes me more real. If I can do ‘the thing’ while being scruffy, then others can do ‘the thing’.

I’m a misfit entrepreneur

If the idea of a successful entrepreneur is someone who jets around the world giving TED talks and works a four-hour week – well that’s not me.

I don’t have a grand strategy.

I haven’t carefully crafted a polished personal brand.

And I don’t get anywhere near enough sleep.

My version of entrepreneurialism involves frantically typing emails on my phone at the Coles checkout or dry shampooing my greasy fringe just seconds before an important video call.

I’m doing the best I can, with the time I have. And so far my best has been more than good enough.

Yes, I may not have my own private island, a seven-figure passive income and a luscious head of hair … but I’m still doing okay.

And if you’re a fellow misfit entrepreneur, I’m guessing you’re doing ‘okay’ too.

Kate Toon

is a copywriter, SEO lover and Hula Hooper based in Sydney. She’s the author of Confessions of a Misfit Entrepreneur | How to succeed in business despite yourself. Connect with her on Google+, Facebook, Twitter and LinkedIn.

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