Are you suffering from entrepreneurial envy?

Are you suffering from entrepreneurial envy?

Or the year I went full circle with my business

A few weeks ago I wasn’t exactly feeling 100%.

I don’t know if my yin was squabbling with my yang, my cosmic planetary alignment was skewed, or I simply wasn’t eating enough bananas. But I was up and down like badger on a pogo stick.

At first I put it down to being a bit tired. It’s been a huge year at Toon HQ, and right now I’m running on fumes.

But then I realised I was suffering from something serious.

I had a bad case of entrepreneurial envy.

And perhaps you do too.

So in this post I’m going to take you through a clinical diagnosis of entrepreneurial envy—the tell-tale signs, the potential treatments, and the long-term side effects.

The pre-existing condition

This year my business and I turned a corner.

After years of happily cruising down the road towards small business success, I inadvertently hit an on-ramp and found myself on the entrepreneur highway.

And let me tell you, it’s been a bumpy ride full of potholes and with loo spots few and far between.

Now this wasn’t a deliberate pivot. As I did more, and became slightly more well known, I was asked to do more.

My ecourse led to me being invited on more podcasts.

One speaking gig led to another. And word of mouth went from a mumble to a slightly irritating noisy hum.

My marketing was working – it was terrifying.

And as I attended more events, I found myself rubbing shoulders (and only shoulders) with horribly successful people.

I went from following these people from afar on social media to mingling, having dinner and suffering late night karaoke sessions with them.

I went from being a small fish in a giant pond to a small fish in an expensive spa water lake full of coy carp.

And it messed with my tiny fishy mind.

At first I coped just fine with these situations.

I focused on spooning soup noiselessly into my mouth while those around me talked about their eight trillion Facebook followers.

I nodded politely when they regaled me with tales of making $68,000 dollars in membership revenue in the time it took me to butter my bread roll.

I smiled. I made appreciative noises.

But inside I was nonplussed.

They were them. I was me. Yes I was smaller, but business isn’t a competition, right?

Unfortunately, it wasn’t long before I started to think, “Wrong”.

After prolonged exposure to excessive entrepreneurial talk, it begins to seep into your inner being through the cracks in your confidence.

A photo posted by Kate Toon (@katetoon) on

When you’re surrounded by people obsessed with big numbers, retention, automation and building a business empire, your own business cul-de-sac just doesn’t seem enough.

I wanted what they had.

I wanted to be a jet-setting entrepreneur with a membership program, a masterclass, and a warehouse full of millennials squatting on bean bags in the up-and-coming part of town.

I wanted to be a real entrepreneur.

They say that when people are far enough away from you, you admire them. But the closer they get, the more you envy them.

Well I can envy Beyonce’s talent because I have no desire to be a singer. But when I see someone a few rungs up the marketing-type-person ladder, it feels doable.

I could be one of them, couldn’t I, and bask in the glow of my ‘golden octagon’ of entrepreneurial success?

The Golden Octagon of Entrepreneurial Success

Psst: I should have added digital magazine to the list but I forgot.

I needed to do all the things, and I needed to be the next big thing—now.

(Well, maybe after I’d given the dog a bath and popped into Coles to buy fish fingers .)


The symptoms

The symptoms of my entrepreneurial ailment began to present pretty quickly.

They included:

  • Dry eyes from obsessive social media following
  • Stomach pains from opening the emails of my entrepreneurial competitors
  • Finger exhaustion from continually entering my credit card details to buy the latest CRM or automation software
  • Carpal tunnel from trying to out-wit, out-write and out-awesome everyone
  • Brain ache from endless pricing and ROI calculations
  • Glazed eyes (not mine other people’s) from talking endlessly about sales funnels, integration and click-through rates.


The snake oil treatments

A quick search of the interwebs provided many possible treatments for the entrepreneur envy condition. Unfortunately, they all promised that if I followed their recommendations I too could join their hallowed clan and be cured.

Hallelujah! All praise Richard Branson!

Options included:

  • Attending ‘free’ business seminars on how to build your business empire
  • Handing over $10,000 for flashy influencer programs sold by tanned men with aggressively white teeth
  • Paying for business gurus who believe you’re only successful if you’re earning seven figures (which you need to pay their absurdly high coaching cost).
  • Joining a Mastermind group of like-minded desperados in an attempt to suck success juice from your entrepreneur of choice.

I’m sure some of these may have worked. But I’ll never know because they all involved giving big chunks of cash to other people—something I don’t particularly like doing.

The ‘heal thyself’ approach

I decided to create my own home-made remedy for my entrepreneurial illness, which involved three core elements:


Unwilling to pay for someone else’s expensive mastermind, I created my own with five other clever people. Of all my DIY treatments, this has been the most successful.


After deciding at the start of the year to go completely solo, I realised I was never going to be a mega success without a team of minions.

  • I tried the overseas VA thing twice – a miserable failure.
  • I nabbed a local VA – a joyous success (thanks Leanne)
  • I hired a part-time book keeper – an easy win (thanks Alec)
  • I outsourced some event management, PR, email set up, WordPress admin and design – a bit of a mash up, but so far so good.

I already knew there would be a pain barrier to go through before things were running smoothly. But I’ve also learned that if the person seems shit at first, they probably are.


I decided to upgrade my much-neglected software and buy all the things, the main three being:

  • Slack: Signed up, got confused, ignored it.
  • Active Campaign: Signed up, went through a world of torment to set it up, and now love it. Mind you, it still frightens me a little, and I’m pretty sure I’m using about 2% of its functionality.
  • Canva for work: Signed up, love it. Great investment.

I also took a step away from day-to-day copywriting to work on my business. Sayonara, clients.

I improved websites, enhanced membership programs, migrated lists, tagged consumers, and firmed up sales flows.

My business has never been in better shape. I, on the other hand, am shattered.

But through this relentlessly tedious, stressful and exhausting process, I realised something important.

I’m not cut out to be an entrepreneur.

I don’t have the energy, the drive or the singlemindedness.

I like the idea of the money, and even the fame. But when I do get a blob of money I realise there’s nothing I need, and people recognising me makes me feel a bit itchy.

Whenever I see someone boasting about how they’ve done 24 speaking events I feel a momentary pang of envy before thinking, “Poor you. All that travel. All those shitty plane trips”.

I lust after someone else’s membership program with automated upsells, downsells and sideways sells, and then think, “What a faff”.

I mentally build my awesome team, and then remember I don’t like working with others, which is why I went solo in the first place.
In short, I really can’t be arsed.

So I kind of want what I don’t want. Go figure.


The side effects

One of the main results of my love/hate relationship with entrepreneurism has been my anti-entrepreneurial rants.

Whenever I feel the boil of confusion and angst growing, the only way to lance it is to blurt out my feelings in a Facebook post. (You can read one here)

But rather than just becoming another internet shouty man (See video below), I’ve started funnelling my energies into an event. (Which ironically pretty much ticks off that Octagon.)

Oh and a book about being a misfit entrepreneur, which you can read more about here.


Ongoing treatment

After taking advice from several wise beasts, I’ve decided to be more comfortable with my own version of entrepreneurism.

And to kill the comparison monster once and for all.

It’s great to have goals. And it’s great to have people you look up to. But when that looking up makes your neck ache, it’s time to look back down and focus on your own game.

To be more awesome. To just be yourself.

And to also celebrate other people’s success. A lot of these crazy awesome entrepreneurs are now my mates, and people I genuinely like. I’m learning to be happy for them, rather than gnashing my teeth with envy.

I’m learning to admire, not envy, no matter how close the person is to me.

I started this year as a successful solo business person, and I’ve gone full circle.

Yes I have the course, the podcast (two, actually), the event, the membership program, the TV show, the speaking gigs, and the book is on its way. But it’s all small scale. It’s all on the low-down.

I don’t make $68,000 while I’m on the loo.

I don’t have the bean bags, or the team.

I don’t have the aggressively white teeth, or enough air miles to buy a small African nation.
But I’m okay with that, for now.

I think.



Stay Tooned

If you’d like updates on how I’m progressing with the book, and would like to help me make decisions about the cover and other fun things, feel free to follow me on Facebook or join my I LOVE SEO group.

Want to read the book intro?



Over to you

Do you suffer from entrepreneurial envy? Share your feelings of angst and worthlessness below. At the very least you’ll make me feel better, and it’s all about me.

Did you like this post?

You might like my book ‘Confessions of a Misfit Entrepreneur | How to succeed despite yourself’ – buy it online here.

Want to have a chat?

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  • As always, a great read Kate. I love your honesty and vulnerability. It makes you human and gives the rest of us hope. 🙂

  • You gotta love those late night karaoke sessions!! You were a natural!

    • I wondered if you’d spot that 🙂 That was for you.

  • Brilliant Kate! Regardless of where in our business journeys we are, I bet we’ve all felt like this – I know I have. The very fact that that you don’t stuff people into your funnel and wear them down with your automated thingo, is the very reason you continue to get such a warm welcome in their inboxes. I’ve unsubscribed from a heap of the Ubers this year – I can’t bear any more perfection and white teeth – whereas your emails land on a feathery bed of welcomeness because they make me feel like a normal, happy human.

    • Well I’m not sure you’re that normal 🙂 But seriously, thank you for reading and contributing and letting my emails land your feather bed. Off to get my teeth whitened.

  • I love this so much, Kate!! It kind of sums up everything I have gone through this year too…except without nearly any of that golden octagon. But I’m not comparing so that doesn’t matter. 😉

    • To hell with the golden octagon, I’m going with the silver oval of simplicity

  • Daryl Ansell

    Brilliant article Kate I think everyone in small business feels that way at times. You inspire so many people to excel in what they do and behave with integrity. That why you tribe is loyal and loves you to bits. One tip don’t video the karaoke for your site 🙂

    • haha – yes lesson learned. Never share karaoke videos with anyone!! Thank you Daryl your support is appreciated hugely!.

  • Love this Kate! And hey, I don’t think you’re doing too badly 😉

    • ah thanks pal – funny cos you have always been one of my people I admire/envy, then I met you and you were like the nicest human. And now I’m just happy for your successes.

  • Modella Clothing

    I laughed out loud Kate. Wonderful article that I can relate to. Love your honesty and rawness. Fabulous.

    • Ah thanks lady – I try to keep it realz – as the kids say – or probably don’t and now I sound like an old, uncool woman.

  • Emma Oddie

    Brilliant, Kate. Honest and wonderfully well written. I too feel the same way about being an entrepreneur. I like running my little business but I like too many other things in life to be single minded enough about it.

    • Thank you hugely – yep I’m the same. Not enough focus or energy. If only I’d started 20 years ago.

  • Shared on Twitter but can’t open the content locker – it tells me I don’t have access & wants
    me to sign up/join first. Any suggestions?

    • Oh that’s annoying, pop me an email and I’ll send you the chapter,…ekk I hope it’s worth the effort.

      • Maybe it’s because I changed the wording of the tweet a bit?! What’s your email address?

  • “Aggressively white teeth” I just spat out my glass of red on the keyboard.
    I knew I was never going to be a massively famous entrepreneur due to ginger hair goofy teeth and an opinion I couldn’t keep to myself….hang on…Duchess of York? Great post Kate. Everyone I know thinks the same about you (i.e. bucket loads of respect) so you can’t be doing that bad 🙂

    • haha – it’s true though isn’t it – SO WHITE. As a fellow goofy teethed entrepreneur I salute you! And thank you for reading and commenting.

  • Alexandra Kadzielawski

    “…full of millennials squatting on bean bag”. I love this Kate! I’ve only been following you for about a month, but I love how well you can articulate real life situations in a humorous way (especially on your podcast). As a newbie copywriter, it’s easy to fall into the comparison trap. Thank you for the reminding us that even those well established can feel envy on some level. Personally, I feel there are too many marketers out there, and too little talent. Often times entrepreneurs will talk about making that “$68,000”, without mentioning that over half of this revenue was invested in FB ads 🙂 This is very skewed…. Hard to really tell what’s true. Okay, back to my bean bag now.

    • Ah thanks for the kind words. Yep that big figure often hides a lot of expenses, and a gazillion wo/man hours of effort. Don’t believe the hype.
      I do love a bean bag, but I don’t have the core strength to exit them with any dignity.

  • Nadia Barlow

    I learnt a valuable lesson about comparing yourself to others recently when I was catfished. This person tried to befriend me and painted a picture of a fake life that made mine seem quite ordinary. I remember thinking gees, I actually thought my life was pretty interesting until now… Turns out it was all made up! There is nothing like the realisation that you were comparing yourself to a person who doesn’t actually exist, to show you the absurdity of it all. The moral of the story is: don’t ever compare yourself to someone else because that person may in fact be a pathological liar.
    By the way the full length version of this story is even more thrilling and comedic but it’s probably told better with a glass of wine.

    • haha well I look forward to hearing it one day. Comparison is the thief of joy and all that, but it’s such a hard lesson to learn and enforce. Thanks for reading!

  • Shauna Maguire

    Loved this post and although I’m running a completely different show to yours, I completely identify with your (hopefully cured) condition. It’s taken me a frustratingly long time to realise that my version of success is simply that – mine. So I can do what I want with it, regardless of what everyone else is doing. There’s so much power in realising you can actually do what you want, as opposed to what you think you should. Cheers to us!

    • Hey shauna, it’s not 100% cured but I’m getting there. And yes that’s the whole thing – we set our businesses up to be free and do our own thing, but then we start trying to do other people’s things. Cray Cray. Thanks so much for reading 🙂

  • “I nodded politely when they regaled me with tales of making $68,000 dollars in membership revenue in the time it took me to butter my bread roll.” Haha! This is brilliant. But in all seriousness, this is an important post. After all, the grass will always seem much greener on the other side, if we let it 🙂

    • Hey yep. It’s my bit bug bear at the moment. Hence the book. We need a bit more truth telling in business.