For Shawn Asselin, corporate burnout wasn’t a sudden explosion; it was the slow erosion of working on technology projects that never saw the light of day. Craving tangible outcomes and work aligned with his values, he launched Willie Wagtail, a premium men’s underwear brand.
But the timing was anything but convenient, Shawn built the business in the margins of his day while planning a wedding, raising a newborn, and holding down a full-time corporate role. Today, with the business experiencing triple-digit growth, Asselin discusses the discipline required to turn a side hustle into a main hustle, the trap of analysis paralysis, and the freedom of building a business that fits his life, rather than the other way around.
What did burnout look like for you in the corporate world? When did you realise something needed to change?
Burnout was a gradual build-up over time. Coming from a large organisation working on technology projects, our team would put months of effort into projects that never saw the light of day. I love working towards a clear outcome and over time those outcomes were becoming less frequent and less meaningful. I’d been wanting to start a business for a few years and I wanted to build something with meaning behind it and that aligned with my interests and values. When I flirted with the idea of designing underwear that would solve problems other brands weren’t addressing, one thing led to another and a year later Willie Wagtail came to life.
You launched Willie Wagtail while juggling a newborn, a wedding, and a full-time job. How did you find any sense of rhythm during that season of life?
That season of life was busy to say the least. My wife fully supported my dream to start Willie Wagtail. She was the one that suggested calling it Willie Wagtail after seeing one at the beach. We were both on the same page with our wedding plans, where we wanted to keep it under a certain budget in a relatively small intimate venue with our closest friends and family. Running a business taught me very quickly that time is your most valuable resource. I became very disciplined with the time that I had, from working early mornings, late nights and the occasional weekend. Most weekdays I would work 5-9 for Willie Wagtail, 9-5 work my day job then back to Willie Wagtail after dinner when the kids went to sleep. When I went into the office, I’d work on Willie Wagtail from the bus on my commute, sometimes on my lunch break as well. I wanted to quickly turn my side hustle into my main hustle.
Running a business on the side while working full-time can be a huge mental burden. What practical habits helped you stay focused without burning out?
The desire to run the business full-time was the fuel that did not stop burning, so it kept me on track to show up and be consistent. Simple habits made a big difference, but protecting time and energy was always at the forefront. Going on a walk or going to the gym really helped reset the mind and think about my priorities for the day or the week. I learned that if my priorities weren’t aligned, they would quietly consume my time and energy without actually moving the business forward. And finally, execution became critical. Analysis paralysis is something I still catch myself in at times, but I’ve learned that making quick, informed decisions and getting things done is what actually moved the needle.
What does your work life balance look like now that you’re working for yourself, and what feels different compared to corporate life?
I think the best way to describe it is that the business fits my life. I work beyond the traditional 9-5, but if we want to take off on a Friday morning for the weekend, we can. There’s a real sense of freedom that comes with working for yourself. I’m still hustling everyday but now I have far more control over how my time is spent, and that makes everything feel more balanced.
You’ve talked about always having an entrepreneurial streak. How has that mindset helped you navigate the pressure, uncertainty, and long hours that come with building a business?
From the beginning, I had a strong belief that I had a great product, but there was uncertainty prior to launching the brand. It’s easy to think in terms of the worst case scenario, not knowing if anyone would buy from us. As you get a few wins on the board, you just keep stacking the small wins and they compound over time.
I also joined an ecommerce community early on which fast-tracked my learning significantly. Having a group of founders around you who are building their brands and going through the same challenges makes the pressure and uncertainty far easier to manage. Getting product validation from customers in the early days lifted a big mental load and gave me the confidence to keep pushing
Now that the brand has real momentum, how are you managing the push for growth while still protecting your time, health, and family life?
We’re experiencing triple digit growth year-on-year, but at the same time I’ve become the bottleneck as the only full-time employee. The focus now is on levelling up from an operations perspective – building scalable systems, becoming more efficient with my time, and laying the groundwork for new hires as we require them. Part of my own growth has been learning to let go of certain key functions, and I’ve now brought on a few contractors to take the lead in those areas. So, my days are starting to look different but my approach to planning my days and weeks hasn’t changed and I still manage to keep my same routine with staying active and protecting family time.
