I never considered myself an entrepreneur.
I had entrepreneurial aspirations and visions when I was younger, but I didn’t have any of the execution that would suggest I can consider myself that.
It was just Julie Ford and myself when I started working with Glance Marketing in 2015. Julie was eight months pregnant, and needing someone to come in and keep the newly minted company afloat while she took an insanely brief maternity leave. In hindsight, it might have seemed like an incredible risk to start with an unproven company with only a handful of clients in a very competitive market.
That thought quite literally never crossed my mind once. I saw it as an amazing opportunity.
Where isolation intersects with entrepreneurship
As much as I have embraced the small team environment and lively startup culture at Glance, I started to notice a very worrisome trend remerging in my life once again: isolation.
I would see envious thoughts creeping in of people that worked with bigger teams where they were able to collaborate and connect. Whether it was a sales team at a large tech company or hair stylist friends that had the benefits of a team around them, I felt jealous of the everyday camaraderie they shared. I began to feel like I was really starting to lose that interpersonal touch, just tethered to my laptop all day. It was lonely. And it really started to impact my mental health.
I noticed this trend early on in my career when I was a radio host for the Moose FM in Huntsville. I was 24 years old, and I had this insanely awesome job of hosting and producing the live weekend shows in Muskoka. I had full creative control of my show, hosting interviews, running social, and managing all board operations – but it was just me in the studio every single time.
No one to bounce ideas off of, no one to talk fantasy football with, no one to grab lunch with. None of it. And that loneliness can build up quickly.
When I fast forward two years later to working in the startup ecosystem, I was very familiar with these feelings that started to re-emerge.
Thinking of my day as an artist’s blank canvas
One of my favourite passages from Steve Chandler is to, “think of your day as a blank artist’s canvas. If you go through your day passively accepting whatever other people and circumstances splatter on your canvas, you will more than likely see a mess where art could be.”
As I started to think more about the way I was thinking, I realized that I was approaching my days all wrong.
If I didn’t want to live my days filled with the same pre-determined patterns and behaviours, attached to a laptop with my only human interaction happening with a barista – then I needed to redesign my day – because nobody was going to do it for me.
I started to embrace the underlying mindset that comes with being an entrepreneur. I stopped waiting for shit to fall into my lap. I needed to make it happen. For me, this meant:
- Reaching out and planning lunch with a friend.
- Reconnecting with a former colleague.
- Booking a midday boot camp workout.
- Being proactive and finding events or speaking engagements to network with others.
If I found my productivity dipped at 2:30pm, then I would listen to my body and go do groceries, laundry, read, clean… whatever.
I quickly realized that working from different parts of the city, Northern Ontario with family or on the West Coast to ski forced me to start thinking more like an entrepreneur. It forced me to level up on my self-discipline in order to be successful at working remotely.
How remote work forced me to change the way I was thinking
I was living in Park City, Utah for the first two months of 2018 and chasing winter all over the west. While I was crushing powder days, the feelings of a 9-5 still lingered, and tore me away from enjoying the moment because my mind was still on work and life back East.
I didn’t know how to confidently disconnect from work (mentally and literally) with technology.
I felt that I always had to be ‘on.’ I felt that I always had to be available for a call, Slack, email, or video conference at any time of the day. And while all of these advancements in communication and technology have made my job so much easier to work and connect from wherever, I still felt a great deal of anxiety because I wanted to make sure I was on top of my work and that I would never drop the ball.
Before I let those thoughts manifest into something bigger and far more detrimental, I made sure that any guilt I was feeling over living this lifestyle was dealt with, as well as any anxiety that came up where I felt I couldn’t fully disconnect from my smartphone.
Isolation, guilt and anxiety tried to rob me of enjoying the moment – until they were met with my newfound self-discipline and the root behind why I was working remotely.
That’s when I started thinking and acting more like an entrepreneur.
Reframing the mindset
The truth is, I couldn’t be living this nomadic life if it weren’t for such a supportive company and an amazing founder backing me.
I feel so incredibly fortunate to have crossed paths with Julie. From the early days with the level of trust she put in me to run a marketing agency while she was on mat-leave to the almost four-year journey we’ve grown this. And to see the positive people the company culture has attracted makes me so proud to be a part of it to this day.
Riding the ebbs and flows of a young company throws you right into the deep end and forces you to adapt to all aspects. So while I speak candidly about some of the harsh realities that can take a toll on your mental health, remote work has truly played a life-altering role in how I want to create my life.
This journey has reframed my thinking that maybe the core of entrepreneurship is about designing a life that feels good on the inside, rather than one that just looks good on the outside.
I’m excited to be a part of the Remote Year program and chart a course all around Europe and South Africa in 2019 and to live the laptop lifestyle spread across 20 countries. I’m going to split my year up in so many different areas that are tailored to doing what I love – and to continue to build off why remote work is such a central part of my life.
Stay tuned. ✌️