In the third of a three part series, serial entrepreneur and investor Josh Comrie talks about the emotional journey of the entrepreneur.

I grew up in the 80’s in South Auckland, and that’s when I first heard of the term ‘entrepreneur’ – I thought it meant a French pastry chef.

The hero career of choice back then was a white collar professional – you know, a lawyer or accountant. Now, there’s an abundance of resources for entrepreneurs… mentors, money, courses, incubators – more than ever before.

There’s better access to markets, better insights available and tools to make the mechanics of running your business really simple. AND, there’s more competition than at any time in history.

The entrepreneur journey is often played up as a hero’s journey. It is now the number one desired career choice for high school kids in America. And this honourable journey is amazing. But it’s tough.

So if you are considering this journey, or are on it, I’d like to give you some insight into the things that business school won’t teach you, your idols won’t share, and Gary V(aynerchuk) tries to tell you in his very American way.

What am I talking about? Emotions!

Now many of you are probably thinking right now, “Well, I’m not that emotional, I’m a strong rational being.” Yeah sure you are pal, me too.

We are all emotional beings, making all of our decisions based on our emotions and then rationalising them afterwards. Or using my favourite bias –  confirmation bias – to justify the hell out of it.

So here I’m going to call out, for me at least, the emotions you go through on the journey of entrepreneurship:

1. Liberated

You’ve left your day job, or incorporated your company. You feel released, you have guidance (once upon a time I would have said ‘control’, but I’ve changed my perspective on what we genuinely have control over as I’ve matured). You have full responsibility for your life. You get to make the calls on this venture. I’m the man/woman!

2. Excitement

For me the unknown carries great intrigue. Plus I love being able to design an offering, take it to market, and take people on the journey with me. There are so many great decisions and opportunities that lie in front of you.

3. Confusion

Man oh man. There are just so MANY decisions to make. And so many things to do. The list is quite literally endless. If you carry any semblance of my core value of growth, you are always looking to improve yourself, your products, your team. Consequently, there’s always more and more things to ponder, plan, and execute. Quite flummoxing!

4. Fear

The overwhelming realisation that I have a team, customers, maybe investors and massive financial commitments. Plus I have competitors, suppliers, brand, operations and cashflow. Yes, I have an existential need for cashflow. OMG! I learned to deal with this very early in my life, but if the ‘ballers life’ is one you desire, get used to some consistent and nagging level of fear. Yes, this is another way of saying pressure. I’m over-stating it, but it needs to be said.

5. Lonely

“How am I going to be lonely?” I hear you say. “I have/will have customers, staff, suppliers etc. I expect to be overloaded with human company.” So yes you’ll have people around you for sure, but they will not share your burden of challenge, stress or workload. Having a thought partner is rare, in other words.

6. Inspirational

Whether you know it or not, you will literally be an inspiration to others – even more so when you’re doing well! You’ll forge the path, damn the naysayers, create something from nothing and hopefully, be able to share your returns with the world.

7. Joyous

Sound out of place? Hear me out. Emotion #6, inspiration, is about others – joy doesn’t come from making oneself happy, rather making others happy. Truly, it does. If you’re being an inspiration, overcoming all the negative emotions I’ve mentioned, growing, making something of meaning, changing the lives of your customers, staff and loved ones… then Wow, you really DESERVE some joy!

To successfully carve this path, you’ll join the hallowed ranks of just one in twelve people or about 8% of the population (according to inc.com – despite record highs of people becoming an entrepreneur). Of those 8%, fewer than half of these go on to build a business (team, enduring product, customers etc).

So to do this, you’re in the 4% of all people of self-employed goodness. Congratulations!

Feel the emotions, and do it anyway, I say.


Josh Comrie is the founder and CEO of Ambit AI and an active angel investor.