Self-doubt, freedom from bureaucracy, and the search for meaning

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Mark Pollard is Strategy CEO at Mighty Jungle, and host of the Sweathead podcast and community. Currently teaching strategy like he has 100 days to live. He is the former Head of Strategy at Big Spaceship, Leo Burnett NY, and Edelman NY with stints at Leo Burnett Sydney, McCann Sydney, Ogilvy, and more. Agency life since the age of 19.

Biggest fuck up?

I feel I fuck up all the time. I trust my brain to get somewhere new doing strategy work, and I can’t point to any of my thinking work that’s blown up in the wrong way. My fuck-ups are usually to do with logistics, concrete things, and politics.

I once published a hip-hop magazine, but I couldn’t keep it going. That feels like a fuck-up. 

With advertising, I left a couple of jobs too early. At the time, I hadn’t committed to an advertising career. I was working in advertising but just until whatever was coming next. I wasn’t feeling satisfied. I kept rushing – who knows where to? I’ve taken a few jobs in New York that weren’t fuck-ups, but I wouldn’t take them again. 

All of these fuck-ups have led to long periods of mourning and deep self-doubt. I often feel alienated – like I don’t fit into this reality. These situations trigger a deep plunge into this feeling of alienation.


Politicians, predators, and passengers. My annoyances come in alliterative threes. I dream of a world in which people doing creative work are able to suffer only their own internal pain and not be pushed through organizational charts, processes and bureaucracy that causes them additional pain for no reason.

Useful advice 

Viktor Frankl’s “Man’s Search for Meaning” has been on my mind for the past couple of years. I took two things from the book:

1. Without a sense of meaning, it’s hard to live.

2. We’re going to make it up. 

Frankl was a psychologist who was also a prisoner in Nazi concentration camps, so these thoughts carry weight.

In one way, they free you to make up whatever life you want.

In another way, they are heavy ideas because…how do you just make it up and what if he’s wrong, and who am I to just make it up?


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