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Heather Thorkelson: How a Life of Exploration Made Me a Multi-Business owner!

Heather Thorkelson Freedom Matters

This serial entrepreneur travelled the world while building her businesses – and wrote a book!

At Freedom, we love our users – not just because they use our product, but because they’re cool – cool people working on cool stuff. Academy Award-nominated screenwritersbestselling authorseditorsjournalists, developers, illustrators, designers, academics, coaches, podcast hosts, comic book writers, students, and entrepreneurs – the Freedom community is packed with curious, creative, and passionate go-getters. We love to share their stories, advice, and processes because how better to learn about productivity than from the productive?

Meet Heather Thorkelson

Heather Thorkelson is a Canadian business coach and consultant now based in rural Sweden. She has been living internationally for almost three decades and working as a coach for incurable entrepreneurs since 2010. She also owns a boutique polar travel agency – Twin Tracks Expeditions – and co-owns an arctic ship management company! But it doesn’t stop there! She recently published her first book, which is quickly becoming a go-to resource for business owners who can never go back to the 9-5, and started The Incurables – a curated coworking community for business owners. Phew!

With most of us on staycation for another year, we couldn’t wait to learn all about Heather’s career journey –and her global travels!

You’ve got such an interesting career and backstory! How did you arrive at where you are today?

I’ve never fit into the 9-5 or corporate world and so after a decade of working within that paradigm, all over the world, I started working for myself in 2010. I built my own successful coaching and consulting business, and then through a very odd turn of events, I ended up meeting my future husband on a ship in Antarctica in 2013. By 2015 I’d opened a second business – a polar travel company – with my husband and his twin brother who are both polar expedition leaders, and in 2021 I became co-owner of a polar ship management company. It’s hard to say how this all happened other than that I consider myself an incurable entrepreneur and I thrive on new challenges. My primary work is still coaching and consulting, but I’m building my other businesses alongside which keeps me on my feet and always learning.

Pair of Penguins in Antartica

Your previous career in the corporate sector you all over the world. Do you think all the traveling inspired your entrepreneurial spirit somehow? Or have you always been an adventurer?

It wasn’t the corporate work that took me all over the world, it was my need to see new places and try new things that had me moving to countries like Japan and Mexico to try different types of work while experiencing those cultures. And that part was borne out of me being the kid of an airline pilot. I was traveling from a young age with my family and moved away from Canada for the first time when I was 14.

I went to high school in Costa Rica and my classmates were from all over the world – it was like the United Nations! So the combination of travel from a young age, combined with the experience of friends from a lot of different cultures doing a lot of cool things (once we graduated) definitely influenced what I thought of as possible for me. But if I’m really honest, I knew from a pretty young age that I was destined for entrepreneurship. It was just a gut feeling I had from my early teenage years.

Please, we need to know more about the Antarctica trip! And how did that lead to founding a polar expedition business?

After I’d been running my business for about 18 months, I was hitting that typical wall of exhaustion that many early-stage entrepreneurs do. I’d moved from Toronto to Peru and while I loved my work, the building phase can be so taxing. Randomly, a friend of mine who I’d met while traveling down the Amazon river in 2005 called me up, told me he was the Ops Manager for a new polar expedition company, and would I like to come and take a short contract on an expedition ship as a polar guide. I was like “Sign me up!” A paid vacation to Antarctica sounded pretty great, and given that I’d already been to Antarctica as a guest in 2010, I knew how incredible it was.

That contract led me to meet the man that would become my husband, a strapping, bearded 6’3 Swedish polar expedition leader. And it turns out, he has a twin brother who is in the same line of work. Given that the polar expedition industry is relatively small, they are well-known and easily recognizable. So by 2015, we’d been together for some time and I could see that a lot of people wanted to travel with them. Being the incurable entrepreneur I am, I was like, “We need to start a company and make the most of this.” Hence, Twin Tracks Expeditions was born.

Heather Thorkelson Twin Tracks Polar Expeditions
Photo by Dean Tatooles, Southern Cross Galleries

You now live in rural Sweden, which sounds like a dream! What influenced your decision to move there and how to what extent does living in a rural environment affect your work and productivity?

Getting married to a Swede was the main reason! We wanted to have a place to call our own after living out of suitcases for a couple of years and Sweden made more sense for us to settle in instead of Canada. Living in the middle of the countryside has been amazing, to be honest. I have lived in so many different environments over the years, the last being a thriving metropolis of 11 million people (Lima, Peru) which is just bananas, especially considering I’m a huge introvert.

Out here we have a great property and I have a home office in a separate building from our main house that’s looking out over a field full of wildlife. I’ve got a sweet dog to keep me company and because there are very few distractions, I’m way more productive than when I’m in a more urban environment. The peaceful headspace I get from living out here is an added bonus.

At what point did you realize that tech was taking a toll on your productivity and time? Or, when did you know that you had to do something about it? 

Very early on in my entrepreneurial journey! It was so easy to procrastinate by scrolling Facebook or falling down YouTube holes, and it was at the detriment of my ability to pay my bills. Once I started to give social media some boundaries, things began to shift significantly and my business started to grow.

As someone who wears multiple hats, how do you prioritize what tasks, activities, or people get your time each day? 

It really depends on what’s urgent or important at any given time. Having three different companies means there are ebbs and flows. And I work with other people so I delegate as much as possible, and then I triage the remainder based loosely on Eisenhower’s Matrix. Furthermore, because it would be very easy to have an endless to-do list, I choose three priority items per day. As long as they get done, I’m satisfied. Anything else is a cherry on top.

The future of work is respect for humans over the push for productivity, and a recognition of diversity in people’s working styles.

How do you optimize your environment for focus and productivity? 

About 80% of my work is done in 90-minute sprints. I’ve never been diagnosed but I’m pretty sure I have ADHD which means I’m either thinking about a million things at once, or I’m hyperfocused on one thing. Sprints allow me to unapologetically focus on one thing and knock it outta the park. They are timed, there are no distractions allowed (thank you Freedom app!), and the only thing you are there to do is The Work. 

Do you have a pre-work ritual or routine that helps you get in the zone? 

Not really. I just let everyone around me know that I’m about to dig in and therefore no unnecessary distractions would be appreciated! Oh, and I always ensure I have water nearby. 

What are some of the rules and boundaries specifically regarding technology that you set for yourself? 

No checking social media when I’m doing a work sprint. No phones at the dinner table. And no social media when I first wake up (you can lose so much time scrolling in bed!). 

closed laptop on sofa

What would you recommend as a first step for someone who wants to become their own boss?

I recommend being really honest with yourself about whether you want the “freedom” that a lot of people peddle online, vs agency – which means you have control over how you spend your days.

I know very few people who are their own boss that use the word freedom. It’s a lot of work, and you can never really turn it off because being your own boss means it’s an extension of you.

I would also challenge that person to ask themselves how well they work without structure, and how they feel about marketing because both of those are must-dos when you are your own boss. 

The idea of solopreneurship is a misnomer – no one does it alone! Just like raising a kid, we need a village.

What is the hardest part about being an entrepreneur?

The stage when you’re trying to do it all alone and don’t have any other business brains to ask for advice, for a second opinion, or just to share your wins and frustrations with. I wish I’d known earlier on that there were other business owners like me who were neither trying to ram their sales funnels down people’s throats nor treating ‘manifestation’ like a business strategy.

I’ve always taken a really practical, human-centered approach to business and it took me a long time to realize that there were other people out there like me. Once I found them, things got significantly easier. The idea of solopreneurship is a misnomer – no one does it alone! Just like raising a kid…we need a village.

What inspires you to keep going when you are challenged or demotivated? 

For me, there has never been a Plan B. In fact, I wrote an entire book about this called No Plan B: A Handbook for Incurable Entrepreneurs and Other Rebellious Souls, because being challenged or demotivated is just part of the journey. What inspires me is that I believe in myself and the value of the work I put out into the world. And there is no other option…it’s self-determination or bust!

What do you do outside of your work routine that helps you stay productive?

I’m a stickler for a minimum of 7 hours of sleep, staying hydrated, and getting outside with my dog for a good long walk (sometimes two) in nature every single day no matter the weather. Being out in nature is my creative ideation space.

spaniel dog enjoying walk in Swedish countryside

Which of your recent projects are you most excited about?

I’m excited about my book, No Plan B: A Handbook for Incurable Entrepreneurs and Other Rebellious Souls which was published at the end of 2020 and has won some high praise from some of the most respected entrepreneurs in the digital sphere. And I’m excited about the growth of my curated coworking community, The Incurables, which has been a game-changer for the small business owners who are a part of it. 

What does the future of work look like for you?

The future of work looks like respect for humans over the push for productivity, and a recognition of diversity in people’s working styles. Individually, we need to work within the constraints of our own unique brains and support our mental wellbeing with tools like Freedom, which helps us create space to focus on what matters.

Heather Thorkelson sitting on couch in workspace

For more about Heather and her coaching work, visit her website where you can also sign up to her coworking community, The Incurables, or order her book.

For information on Heather’s polar travel company, visit Twin Tracks Expeditions and follow on Instagram and Facebook.