Starting Over, Again

Chasing “cool” jobs, and going back to a 9–5

The theme that ties all of these newsletters together is starting over. Whether that’s after a relationship ending, through recovery from illness, or moving into a new career.

I’ve always been envious of people who knew what they wanted to be. My younger brother is a very skilled builder. He knew from a young age that that’s what he wanted to do, so he went about making it happen during his high school years. One of my best friends is an extremely talented architect. She, like my brother, left school and made a plan, studied, got a job.

That was not my experience. I liked biology and history in high school, so I thought I should probably study environmental law. Instead, I ended up doing a degree in microbiology and geography. I worked for the council, then started a lunch delivery business that turned into a catering company. After that, I worked as a chef, a yoga teacher, at an insurance brokerage, as a marketing manager. I took a full year off work, then went into retail for three months, before the move to Bali to work as a travel writer.

I suppose it depends on the school or household you grew up in, but the message I received loud and clear was that you were supposed to see things through. Even when it didn’t feel right. You were meant to stick with it. Not take sick days. Accrue all your annual leave. Collect your weekly salary and hope you’d be looked after.

My first proper job was at Christchurch City Council, after the earthquakes. I worked (outrageously) as a building control officer and stayed for two years. During that time the council went through a major restructure, and people who had been loyal for over twenty years lost their jobs.

It was there I did a ‘personalities at work’ training, based on the Enneagram test. It was the first time I properly realised that people valued things differently to me. People genuinely valued stability, security, and tradition. That was a turning point. I understood my parents better, and why teachers and managers had always seemed uneasy about my decisions. At the end of the course, I had a meeting with my manager and the facilitator to talk about my professional development. The facilitator told me I should probably look for a different job.

That was also around the time the first wave of travel vloggers started blowing up on YouTube, and the QUIT YOUR 9–5 messaging got very loud. I was 21, so I did.

More than half of New Zealand workers are considering a career change in the next year, according to a 2024 Robert Half study. People are looking for higher pay, better work–life balance, and a chance to learn new skills. Millennials are leading the charge, but career restlessness spans every generation. Still, most people aren’t going through with it. A 2025 SEEK survey found that while 41% are open to making a change, only 6% are actively pursuing one. They’re held back by financial pressure, a lack of qualifications, or the belief that it’s too late. Meanwhile, 54% of workers already regret the path they’ve taken, usually because of low pay, shifting interests, or a sense that their work feels empty.

Flexibility has become a major priority, especially for people dealing with health issues, caregiving responsibilities, or burnout. Remote roles and adaptable schedules offer more than convenience. They offer sustainability.

I’ve always chased the ‘cool’ jobs. Mostly because I have a chronic illness, so the flexibility appeals. And also because these are the things I’m good at. But those jobs tend to have a few things in common:

• There’s an unspoken rule that you’re underpaid, because it’s a privilege to even have the job

• You’re easily replaced

• You’ll be paid in exposure

So after a year of being in and out of hospital and working from bed, I’m changing things up again. I’m going back to 9–5 as senior writing lead at a digital agency, and it feels so right. I’m ready for a regular salary and hours. Even after saying I’d NEVER work in an office again, this role is collaborative, creative, and it’s going to be a challenge, which is what I need after six months of off-and-on hospital stays and irregular hours.

This has reminded me of all the seasons in a lifetime. It’s a mix of sadness and relief to come to the natural end and not overstay my welcome. It’s exciting to acknowledge the end of one and the beginning of something very new.