Tomorrow, Wednesday, I'm getting on a stage to talk, out loud and on purpose, about the worst calls of my career.

The event is called Revved Write-Offs, and its premise is simple and a bit uncomfortable. We're hopeless at talking about failure in business. So three of us are standing up to do it properly.

I'd love you there. Wednesday 10 June, 5:30 to 7:30pm, QB Studios on Ponsonby Road, with a panel and drinks after.

I’m there with two people I admire, success stories, Rochelle Moffitt and James Boult, the type of people who you definitely wouldn’t associate with things going wrong.

A business that went sideways. A decision that cost us. A year you'd cross out if you could.

The format leaves nowhere to hide. Twenty slides, twenty seconds each, the clock running the whole way and stopping for no one. Six minutes and forty seconds to name the loss and tell the truth about it.

And if you can't make it, what follows is the part I most wanted you to read anyway.

Everyone talks about sink or swim. But they only ever mean the swimming. The comeback, the lesson learned, the part where it works out. Almost nobody talks about the sinking, the months at the bottom of the pool with your lungs burning.

I’ve done a lot of sinking.

My career has lurched between industries that have no business sharing a CV. Coffee roastery. Welding importer. Agencies. CMO gigs in (separately) sports and technology. Now my own shop. It’s been a lot of things. It’s never once been boring.

And every time I start something new, I say the same thing to my wife:

“I can’t do this. These people have backed me, and I haven’t got a clue.”

Australian entrepreneur Dante St James recently shared some numbers at an excellent webinar he held: 84% of entrepreneurs experience imposter syndrome regularly. 86% of successful ones still feel like frauds. As Dante put it, “the doubt doesn’t go away when revenue grows. It just gets sharper.”

The doubt isn’t a flaw in high performers and risk takers: It’s a feature.

The people who feel most like impostors are usually the ones who care most about getting it right.

In no particular order, here are some of the “jumping in the deep end” stories from my talk at Revved. Write-Offs.

At 22, I got dropped into a welding company. The owner handed me the keys and wandered off, the way someone had once done for him. Everyone there had been doing the job for ten or twenty years, and in walks a pimply-faced kid. They suspected I didn’t know what I was doing. They were right.

The first six months were marked by open hostility. Two years later, we left as mates, and I was good at the job.

I took a lesson from that, and it might have been the wrong one. I decided optimism plus enough effort could dig me out of anything, so I kept jumping.

But hope in and of itself is not a strategy. In some ways, it’s a tactic, but it needs to be deployed accordingly, not as a default setting. Otherwise, you’re just endlessly jumping into situations that may not be optimal.

Another thing I learnt along the way: bosses can be bad at their job and cost you yours. 

Once during a performance review, the main feedback I got was that I was “too trusting”. My boss once told me to watch out for colleagues with bad intentions. I found the idea baffling. It said more about them and the toxic business culture we were in than it did about me.

Years later, in a different job, a sales role, my boss and another senior colleague asked me for my stretch target for the year. I said 350k. They came back before the board meeting and asked me to double it to 700k. I asked for more resources. No, they said, we’ll simply back you (presumably, with vibes). 

They talked me round over a few days until I caved. Then the board meeting came and went, and somehow, when the smoke cleared, the number landed at a million. No more resources. 

I was already cooked. I just didn’t know it yet. We finished the year around 360k, ten grand above my honest first number, and they did everything they could to pin the miss on me.

Here’s the pattern I could only see in the rear-view mirror. Jump into something new. Sink. Slowly start to swim. Then, right as it got easier, jump again. A treadmill I didn’t know I was running.

All that jumping made me broad. For years, I envied people with linear careers, the ones who picked a craft and went deep while I kept starting over. I thought depth was the prize and I’d traded it away.

This might be the best time in history to be a generalist. Range used to look like a liability, a sign you never settled down. Now AI hands you depth on demand. The broad operator who asks the right questions across ten domains, and can summon expert depth in each one in minutes, is suddenly a serious proposition. Turns out the jumpers were just early.

So I’m still jumping. I’ve just got better at picking my dives and at swimming a bit sooner. The self-doubt never left. I stopped waiting for it to.

I still think I can't do it. I jump anyway.

On Wednesday, I'm doing exactly that in front of a room, with a clock that stops for no one. Come and watch me try. As I said, Rochelle Moffitt and James Boult are telling their write-offs, too, and both are worth the ticket on their own.

Why are we doing this? Because each time I hear stories like this, I feel a little less alone and a little bit more perspective. That’s what I hope for you. If you’re having a rough day, just know that nothing is ever as bad (or as good) as you think it’s going to be. 

Cheers, Dave