This is the most honest I’ve ever been about being an eventepreneur. It’s extremely difficult for me to talk about this stuff and I’m concerned that it will make me look weak. But in truth, I’m tired of smiling and saying that everything is fine.


There are two things I hear a lot as an eventepreneur.

“Man, I’d love to start my own company one day.” and “You’re so lucky to be able to set out on your own!”

And probably the most common one that causes me to have to lie the most often:

“How’s life?”

Some people look at my company and believe it to be a successful venture; and to the outside world, it can seem that way. After all, we’re swamped with requests for events, have taken on our first team member, close to taking on our second and have a global brand and blog readership of millions to show for all our efforts.

But there’s only one problem. I don’t feel successful.

In fact, most days I feel like I’m riding a bike with no brakes down a hill. I’m just swerving and trying to keep from crashing. And that team member…well, whenever I turn around on the bike, I see her smiling face staring back at me with the highest expectations shining in her eyes, riding her own brakeless bike, following my swerves and turns.

It’s terrifying. If I make one wrong move, if I don’t swerve fast enough, if a strong enough gust of wind hits me sideways, then we both could go tumbling down the mountain. And yet, when I’m asked, “how’s life?” I cheerily smile and tell them that things are great.

Why? Because I know that no one wants to hear me complain. After all, I’m the lucky one. I’m the one who managed to get his company off the ground and make it “successful”. I’d look like a petulant child who had been given the greatest toy, only to throw it back at his parents and saying he wanted it in a different colour.

So, I smile. And I lie.

The Loss Of Quiet

I think the thing I miss most from the time before I started my company is the quiet. I used to enjoy lounging on the sofa, laying in a park, or walking around London and just letting my mind wander. I used to think about events I wanted to create, things I wanted to make, words I wanted to speak to my friends and dozens of other fleeting thoughts that never stayed long but were always entertaining.

I used to refer to this as my quiet time. I loved it. Even though my mind was active, it wasn’t racing. It was simply wandering.

Now, however, those peaceful meandering paths my mind used to wander are gone. They’ve been replaced by an F1 circuit. There’s this unending roar of engines as my thoughts race around my head. The thoughts are no longer abstract and compromising, but rather they’ve become precise and pressing. What’s our revenue this month? What are sales looking like? Will this new event proposal close before the end of the quarter? Am I being too hard on my team?

Before my partner would ask me when he saw my eyes drifting off into some daydream, “What’s on your mind?” I would smile and simply answer, “Oh, nothing.” Now he sees a look of concern on my face, and he asks me the same question. But I can never truly tell him, “It’s nothing.” Because it’s always something.

It’s now to the point where the quiet is almost unnerving. I try to keep my mind occupied as often as possible to keep the roar of the engines from deafening me but this makes me feel like I’m always “on”. I can’t take a moment off. Holidays have become a week-long effort to shut out the noise and try and relax. And most of the time, I’m unsuccessful, so I don’t look forward to them. They’re now just week-long periods where I’m not fully connected and not fully in charge.

I don’t tell the people who ask me, “How’s life?” about this. I think they’d just see me complaining. They don’t really get how much I valued my quiet before everything got so noisy, so why would they understand just how much I miss it?

So, Why Don’t You Just Stop?

This is the question I’m asked by everyone that I do open up to, the people that are closest to me. They wonder why I’d continue doing something that makes me feel crazy, depressed, and anxious. And I like to tell them that while being an eventepreneur does make me feel all these things, it also brings with it positives. It energises me, it gives me a purpose, it fulfils me.

This is all true. But honestly, I think but I’m not sure if I could find other things that would bring me those positive feelings. There really is only one main reason I don’t stop. I’m scared –  actually, I’m terrified.

I’m terrified that if I were to give up my company that my team wouldn’t understand and accuse me of failing them.

I’m terrified that if I took my foot off the pedal for growth, that the buzz around my company would fade, the spotlight would shift, and we wouldn’t be the ‘industry darling’ that we are today. And if we don’t have that buzz, would my team still have the pride they currently have? Would they still want to work for a company that wasn’t as exciting?

I’m terrified that I would never love something as much as I love running this company.

I know that sounds counterintuitive after I just told you that this company makes me crazy, but it’s true. I love this company and I love being an eventepreneur. I love building something with a group of people. I love knowing that my dreams and ideas have somehow coalesced into a physical thing that is providing a living for someone other than me. And I love being able to provide a service to clients that they truly need and are grateful to receive.

And that’s my dilemma. I desperately love the thing that makes me miserable. And I think that this isn’t unique to me. I think a lot of entrepreneurs deal with this dichotomy of emotions.

Maybe It’s Just Me

Hey, maybe it really is just me. After all, I’m not a sad sack that just mopes around all day. I keep my energy up, I engage with my team, I truly enjoy what I do on a daily basis. But I constantly have this monster that seems to be standing over my shoulder waiting to pounce. It’s the monster of depression. If I let my guard down for just a second, suddenly all the great things in my life are numbed and the challenges are enhanced. My leisurely bike ride with my team, along a winding river trail, suddenly pitches downward into the aforementioned steep hill.

I’ve sought help, both professionally, spiritually and from the few people, I class as my mentors when it comes to this depression monster. There are solutions to making it less powerful. For instance, meditation does help, and is essential for my sanity and helps take the edge off.

I’ve tried to dull that monster’s claws and teeth with medication. But that medicine comes with a price. While it does dull the monster’s effects, it also dulls my edge. It takes away that positive anxiety that pushes me on to the next challenge and keeps me aware of opportunities that are just around the corner. So, I avoid them. Because I’m just as afraid of losing my edge as I am of letting that monster win.

So What Do I Do?

This is the most honest I’ve ever been about being an eventepreneur. It’s extremely difficult for me to talk about this stuff and I’m concerned that it will make me look weak. But in truth, I’m tired of smiling and saying that everything is fine. Because, while things are good, they’re not always fine.

I don’t really know what I hope to accomplish by writing all of this, but I know that I would love to know that someone else is struggling with the same monsters, brakeless bikes, and roaring engines that I am. Because that means that someone else might have found a way to make all those things make sense.

But more than anything, I think this is just my way of blowing off some steam before the kettle explodes. It feels good to get this out ‘on paper’ – it feels cathartic to let down my guard.