I Left My Heart in Calgary

I Left My Heart in Calgary

  • calgary
  • silicon valley
  • quality-of-life
  • technology
  • arts and culture

In less than 10 years, I moved to Calgary twice. The first time, in 2007, was exciting and scary at the same time. I had just graduated from university and decided to leave my hometown of Winnipeg. You might think, “Who wouldn’t want to leave Winnipeg?” and you wouldn’t be completely wrong. I kid, Winnipeg.

But at that time, it was more than just about where I was leaving. It was where I was headed.

As someone born and raised in the prairies, Calgary represented this far-enough-away western land that was not only bigger, but also booming.  I remember this period of preparing to move West fondly; it was filled with the thrill of the unknown. This included moving into my first apartment in the Beltline and establishing a career for myself in marketing. It became a lifestyle I worked hard to achieve, and couldn’t picture happening in my hometown.

But it wasn’t until I moved back to Calgary earlier this year, this time from San Francisco, and now married and a new father, in which I realized what Calgary truly means and has afforded me. Perhaps it goes without saying that the decision to leave an amazing city like San Francisco, was a lot more difficult of a decision than when I decided to leave Winnipeg ten years earlier.

Before I get into my experience living and working in Silicon Valley, this mythical land of "tech bros" and "unicorn startups", and why I gave it up for a city known to many as “cow-town” – it’s important to share more about my first experience living in Calgary.

This city has always treated me well. There have been good times galore. Back in 2007, when I first arrived with my resumé in hand (literally), I immediately found Calgarians friendly and supportive. Not that there were many native Calgarians that I met. Mostly, it was people from all over the world that I befriended in pubs like The Ship, who had left behind their own version of a “boring prairie town”, and made Calgary their new home and a place for opportunity. It was this collective sense of ambition and wild west adventure, that always kept life interesting for me as a 20-something year old in Calgary, who could also spend weekends in the mountains.

This period also included reuniting with old high school friends from Winnipeg, who had moved to greener pastures in Calgary months and even years before I made my move. From having this sense of brotherhood to entering a real adulthood, I eventually settled down and met my wife to be, a rare Calgarian born and raised, who had recently moved back to her home city after living in Whistler for several years. During my first five years in Calgary, I had not only bought my first condo in Bankview, just stumbling blocks from 17th ave, but also moved on up (now with my wife) to our first house in Garrison Woods. Calgary will always hold a special place in my heart for these reasons – from establishing my independence to finding my true love, both in my city and my partner.

Warm and fuzzy feelings aside, my first time living in Calgary also opened my eyes. It wasn’t about the money and powerful oil companies. Executives in fancy suites entering their office towers and doing lunch downtown wasn’t my thing. What became an eye opener for me was discovering entirely new communities within Calgary that I was amazed to find.

My first job in Calgary, and really, my first serious job post-graduation, was joining a not-for-profit theatre company. In 2008, I was hired as the marketing and communications manager at Theatre Junction in the historic GRAND Theatre downtown. Not only was the building very unique, but by working at ‘Calgary’s Culturehouse’, I was exposed to the city’s diverse and contemporary arts scene. Something I had no idea existed when I first arrived months earlier. It definitely was not something I expected Calgary had when I first moved here, let alone was so diverse and beloved. From presenting world-renowned theatre on our historic stage, to hosting packed parties in the theatre’s back alley, I was immersed in art and culture. If I thought Calgary was mountain town cool when I first arrived, I quickly learned through our buildings and cultural scene that we could be New York City-style cool as well.

Working in Calgary’s arts and not-for-profit sector, was not only an eye-opener, but also an amazing experience. From working with our community partners around the city, including other innovative theatre companies like One Yellow Rabbit and Alberta Theatre Projects, to meeting more of our local musicians, dance ensembles, and other unique places and spaces at the time like Arts Central, where we’d promote our season’s shows, it felt as if I was living in one big creative workshop of a city. It exposed me to new thoughts, ideas and ways of looking at society and the world at large. And it forced me to see things differently, not so black and white, or in the case of living in Calgary, red and white.

In some ways, ironically, the arts community in Calgary reminded me of Winnipeg’s – and unbeknownst to me at the time, it was much bigger and active than that of the Peg. I saw how people from all walks of life supported Calgary’s diverse arts scene, came together, attended each other’s shows and fundraising parties. The often weirdness and kookiness of it all is what intrigued me.

I saw artists interact with oil and gas execs. This convergence of corporate Calgary and its sponsorship of avant-garde theatre, was beautiful and powerful at the same time. Business people I’d otherwise never meet or associate with, became our patrons and friends. This showed me the city’s rich sense of generosity and how several different, distinct communities could band together. It was the first, but definitely not last time I’d experience the wonderful community feel of Calgary.

It also broke down my own stereotypes of what Calgary appeared to be from the outside, even after I first moved to the city. Stampede parties and a C of Red were there if that was your thing, but I craved something more. When I became a “cultural” insider by working at one of the city’s most historic venues and gathering spots for art shows and political events alike, I’d meet students, regular joes and prominent Calgarians all at the same time - mixing and mingling. Ultimately, we were all working together to make Calgary a more interesting, innovative and diverse city.

The spirit of the city burned bright both on and off the stage. Artists and performers who toured the world would often tell me just how warm and special Calgary is.


Shortly after getting married in 2013, the flood hit. The river’s wrath of destruction affected my family personally (my in-laws lost their home). While it’s been talked about time and time again, the sense of community and camaraderie among Calgarians was something remarkable, but (hopefully) we’ll never experience again.

It was around this time, the summer of 2013, in which I began looking for my next career move. I had left the theatre a couple years earlier, and moved into the ad agency world.

Being someone who has always gravitated towards the fringe and counter-culture, I’ve been drawn to new technology and new ways of thinking (and doing) for as long as I can remember. New modes of communication, from social media to virtual reality, excite me, just as much as classic literature from the last century’s greatest writers and poets. And as much as working in Calgary’s not-for-profit scene was a great learning experience, and groomed me for something bigger, I was now ready to apply this marketing knowledge to help companies around the world undergo their own digital transformations.

I was hired as a digital strategist in 2010, and later became a Director of Digital Strategy for a global ad agency, who had a small satellite office in Calgary. I worked with local, national and international clients and helped them establish their online presences, social communities and leverage technology to drive deeper engagement with customers and employees alike. The work was rewarding – but more valuable to me, was what I learned and absorbed from the creative directors and designers I worked with. Some who came from Toronto and Montreal, others from Vancouver, but who now were all embracing life in Calgary. It was through these online campaigns and web launches we worked on together, which ultimately led me to San Francisco.

Near the end of 2013, I was offered an opportunity to transfer and relocate to the agency’s larger office in San Francisco – an opportunity I couldn’t pass down, and one in which I didn’t know for sure if or when I’d return to Calgary. As someone looking to make my mark in the tech industry, I knew what the Bay Area could do for my career.

What I didn’t quite realize at the time was what was also being built in Calgary.


It goes without saying what a great city San Francisco is; however, living there never quite felt like home. While yes it was California, and I could enjoy the beauty of the ocean, beaches and gazing at palm trees while working in the mecca of innovation and technology, there was something missing. The warmth I was used to, from fellow Calgarians and our community spirit, was gone. So too was 300+ days of sunshine a year.

While San Francisco will always hold a special place in our hearts (our son, our little American, was born there in 2014), the inevitable slowly started to creep into our lives shortly after we moved and our son was born. From learning first-hand the complexities of the American healthcare system, to the fact that for other new parents (including new moms) the norm is to be back at work just a few weeks after birth – something did not feel quite right for my wife and I. Blame it on being spoiled with our Canadian life, but family values in a large U.S. city, are not the same as family values in our home and native land.

There was a lot more to it than that as well.

Was it the outrageous cost of living in San Francisco? Two million plus for a fixer-upper? No thanks. Homeownership was a pipe dream. An American Dream this Canadian would never know.

When I got my first U.S. pay check I couldn’t believe how much I was taxed by the state of California. It made me want to write home and send a love note to the Alberta taxman. 

My wife and I were also spending too big a portion of our paychecks on rent, just to have a decent apartment for our small family of three. While we liked our place, in a great San Francisco neighborhood away from downtown, and with spectacular views of the Bay, there was little outdoor space. Worse yet, getting to work in the morning was no cup of tea…er…Tim’s. People naturally complain about their commute in whatever city they live in, but when you live in a major U.S. city, the struggle is real. And then some.

Seeing first-hand the disparity of rich and poor everyday as I ventured to work in San Francisco’s Financial District, was so much more pronounced than anything I’d ever seen in Canada (I’ve lived in Winnipeg, Montreal and Calgary). It was depressing and a sad reminder of a city and environment that has all but forgotten about it’s less fortunate. Not to mention the artists who made the city the epicenter of the counter-culture movement 50 years earlier. It forces good people out.

There were many early mornings as I rushed to work in which I could barely move on the San Francisco Muni subway. The speed of the train (when it was working and on-time) much resembled the pace of life in a city where so many young professionals are so narrowly focused on their status in life and the inflated salaries needed to live just a regular life. And of course, their startup stock options – the golden ticket to early retirement in Silicon Valley.

I quickly found out that that type of million-dollar fascination and obsession is wishful thinking at best. After a year with my agency, I decided to switch jobs and do what you do when you’re young and ambitious in a city like San Francisco – work for a fast-growing software company and hope they skyrocket to the moon. 

But in this kind of all or nothing, uber-fast pace environment, you begin to see the worst in people. Granted I was forced to push myself and reached professional heights I’d never been before, just to keep up with the level of talent I was surrounded by, it often wasn’t easy to relate to my American teammates. As I often worked beside people who had held senior level positions for companies like Google and Twitter in previous roles – their often know-it-all attitude and preoccupation with pre-IPO stock valuations was anything but friendly, nor creates a culture of trust and collaboration – ironically, the values many startups in Silicon Valley bestow.

Office politics also take on a whole new meaning, especially when early retirement is at play. Work Life balance becomes non-existent. I often felt like an outsider because I was in my mid-30s and had a child - while most other colleagues my age seemed only married to their work and ego.

After working with a couple different startups that didn’t take-off, my final stint in San Francisco was with what would become one of the U.S’s fastest growing financial technology (FinTech) startups. I was hired as a marketing director in 2016 and stayed for over a year. During the time I was there, the company quickly rose to become one of Silicon Valley’s greatest success stories, and reached true unicorn status. The company raised a billion dollars in equity. We grew from 500 to nearly 1,000 employees in one year. The company reached a valuation of over $4 billion dollars. It all seemed surreal. We had what felt like an unlimited marketing budget, and were given the autonomy to try new things – which was great. The rocket ship was finally taking flight.

But everything, including a great salary, came with a steep price – your total devotion to the company, at the sacrifice of time with family and friends. 12 hour days were the norm. As was going to work with the flu, and working on weekends.

Even with a competitive salary in San Francisco, the only way to afford a home was to move outside the city. By doing so, we’d be looking at a morning commute over 60 minutes. I’d chat with colleagues who commuted, and who took transit from places as far as San Jose, or drove in from the North Bay, and would easily spend 90 minutes commuting each way.

We wanted our San Francisco city life, it was an important reason we moved down there in the first place. But even that began to mean less.

When compared to a mid-size Canadian city, a city like San Francisco definitely has a more storied history. That certain cache. And when telling friends back home about our lives in the city by the Bay, they commented at how lucky we were. But the truth was, I was growing jealous of these same friends back home in Calgary.

On the few occasions we did make it back home to visit (for the occasional holiday, or the need to leave the U.S in order to renew my work visa), I saw how Calgary was once again transforming. What was being developed impressed me. Changes in the East Village. New shops in Inglewood. Walking through a revitalized Bridgeland. And so much more happening in every corner and quadrant of the city. It reminded me of the same feeling I got when I first moved to Calgary almost a decade earlier.

During these trips back to Calgary over the past few years, the city was of course in the midst of its worst recession in decades. We’re still feeling the impact. But even during the worst of it, I could sense optimism. Speaking with our friends, and even friends of friends when we’d visit, we’d hear about them now having the time to pursue their passion. Their startups. Their boutique agencies. Their brewery ideas. Their clothing stores and coffee shops. Flash forward a couple years later, and many of our friends did see these passion projects and business endeavors through. The resiliency and determination of Calgarians is infectious. This excitement and energy of Calgary began to take hold of me again.

We’d often go out for dinners with friends when visting Calgary. I’d hear them mention other new Calgary startups and tech companies making an impact not only in the city, but on a world stage. I learned about Benevity and how they were using the power of technology for social goodness. Through my own research, I learned about several new Calgary startups making waves in the FinTech space. There was a new Innovate Calgary building by U of C, which has become home to dozens of other startups. It was like what I was seeing happen in San Francisco’s SoMa district, but much more affordable to live in. 

I’d also drive through the neighborhoods I used to frequent when I lived in Calgary. Everywhere seemed so easy to get to, relatively speaking when I’d compare it to our lives and mobility in San Francisco. How our unique Calgary neighborhoods felt like their own small towns, was both charming and appealing again.

I’d marvel at new architecture like the Peace Bridge and National Music Center. Buildings and bridges on par with anything back in San Francisco. While we liked to spoil ourselves in San Francisco with every hipster trend imaginable, I was surprised to see the exact same options readily available throughout Calgary at new bustling restaurants and cool coffee shops opening on the regular. From avocado toast to microbreweries, and large bike paths and vast dog parks, Calgary didn’t remind me so much of Houston or other cities we’re commonly compared to. It reminded me of Seattle, Portland, and yes, even San Francisco, which I could attest to first hand.

The uniqueness of Calgary neighborhoods, and the trendy restaurants and shops popping up in neighborhoods like Kensington Village and Marda Loop, showed me that Calgary has everything you could ever need. Over dinners at Charbar and Una, and rekindling our monthly family tradition at Silver Dragon in Chinatown, I’d tell family and friends that the city’s new restaurants and chefs could rival anything and anywhere we ate at in San Francisco. And on the simpler joys of life, whether it’s a Guatemalan pour over coffee from Phil and Sebastian, or a Fiasco Gelato from a food truck festival in the East Village, there never seemed to be a dull moment or treat left behind in Calgary.

As we now had a small child, I’d also notice the many parks and playgrounds around town, more so than I ever had before. The amount of green space in Calgary is amazing, and could give any other city in the world a run for its money.

But the biggest difference I could see between what life back in Calgary could be like, to what we were experiencing in San Francisco, was that in the former, Calgary life seemed all so manageable. Even in the dead of a Calgary winter, where 20-degree weather and palm trees awaited us back by the Bay, I found comfort in the reflection of Christmas lights on icy streets and the lure of the mountains less than an hour away. You don’t realize how nice having four seasons actually is until you can’t have it.

When we’d return to our busy lives in San Francisco, we’d try to appreciate what the city offered. There was a lot after all. We indulged through dinners at 3-star Michelin restaurants. Wine tasting weekends in Napa, trips to Tahoe, and hikes through the tallest redwood trees.

But with raising a one-year old on our own, these opportunities, including a simple night out at a bar or restaurant, became rare and much too costly. Even when we did go out on the town, I’d often think of how the dinners we’d have in Calgary with friends along 17th Ave, or on Stephen Ave were just as fantastic and fulfilling.


After our son was born in 2014, we needed to begin thinking about preschool in San Francisco. How crazy I thought. Applying for schools well before our son even turned one. The cost of these schools was one thing, but the competitiveness, just to send your child to a decent school, was unsettling. It felt like something you’d read about or watch on TV, but now we had to throw our own hat in the ring.

Ultimately, it came down to weighing options. On one had – stock options that would take another three years to fully vest, and may never amount to much, regardless of how successful the startup I worked at was that year. On the other - quality of life. Life won.

We moved back to Calgary this past Spring, and seeing the leaves on trees and flowers reborn, was very suiting for where we were in our lives. A full circle, and life was beautiful.

Our best friends are blocks away, not cities away. Our mortgage is 1/3 of what our rent was in San Francisco. And our son has a backyard to play in.

I work at a great startup called Chaordix in a cool building that allows even cooler dogs. At work every day, when I walk into our office in Ramsay, I’m often reminded of the spirit of San Francisco, and what drew me there in the first place. (In full disclosure, Chaordix is the software company that powers the #LoveYYC community you’re reading this from).

This past summer I got out to Sled Island and Calgary Folk Fest – amazing festivals and world-class talent all around. On weekends, we walk through farmer markets with our son. Our toughest decisions aren’t about expensive preschools but rather revolve around deciding which of the five toddler-friendly parks near our house we’ll go to today. We go on date nights and walk through night markets in Inglewood. We take our son to the TELUS Spark, which rivals any children’s science museum, or Exploratorium in the world.

We’ve also continued our pursuit of becoming bonafide foodies, because much like in San Francisco, Calgary’s cuisine scene enables us to do so. And when we’re feeling lazy, ordering in from the Garrison Pub is just as special. Thank goodness for the food delivery apps in the city. And if I need to be reminded of California further, I can easily stroll past all the packed yoga and Pilates studios just in Marda Loop alone.

Calgary may not be romanticized in Hollywood movies, or have been the subject of muses by great poets. I can’t think of a song named after Calgary (not sure if that Bon Iver one counts?), and it may not have inspired local music scenes that define generations.

And that’s just alright with me. Because Calgary is also more than Stampede parties or memories of Winter Olympics from decades long gone. It’s a great city, like any great leader, that breaks down stereotypes, inspires the people around it, and overcomes the great challenges thrown at it.  

While we now have more breweries and hip coffee shops than ever before – it’s important to remember that almost every city has these things. In today’s world, trends are a commodity.

A rarer resource is great people. And that’s what Calgary is most rich in. It’s what leaving and then returning to our city taught me. From our renowned mayor to the game changing work our city’s startups and tech talent are creating. How our arts scene continues to evolve and push boundaries, and how we continue to be a place where major corporations in renewable energy can flourish.

There’s no doubt the city has changed. It’s been forced to. And it keeps changing and keeps growing by leaps and bounds every time its forced to get out of its comfort zone. Much like we all do.

We don’t crave attention or need to be mentioned in the same breath of cities with multi-millions of people. But when it comes to livability, we’re on the lists that matter. With over a million people, I think we’ve found our sweet spot. There’s always enough to do here, to keep us busy and entertained. But we can have it all with less congestion, a lower cost of living, and, most importantly, a much greater quality of life.

The things that matter most to me now that I’ve returned to Calgary as a father – cleanliness, low crime, affordability, parks and recreation - are must-have’s I can enjoy every day. They’re not trumped by rows of skyscrapers with glass ceilings, or hidden by too much rain or pollution. The mountains are always in reach. Achieving new heights is always there for the taking.

Still, Calgary seems to be one of the world’s best kept secrets. Perhaps we like it this way. After all, it’s only a matter of time again before more brilliant and ingenious minds catch on and also make this city their own. And we will welcome them, like we have always done before. Anytime you have a place with so much talent and a willingness to reinvent and transform – you attract the best in the world. As our industries evolve and change, to those that are more green and digitally-inclined, we continue to lead by example. We’ve still kept our essence of entrepreneurship, with a hint of the wild west for good measure. It’s intoxicating.

Leaving San Francisco meant leaving a rat race for a pace that’s much more comfortable and rewarding. In Calgary, I have an open range and canvas for exploration and finding and pursuing the profession AND lifestyle I want to lead. This also includes opportunities to meet many other like-minded people who are passionate about the same things as I am.

This is what I love most about Calgary. When we keep surprising visitors and new transplants to our city, and breaking down stereotypes. From fashion to food, Stampedes to software, it’s how our city continues to offer the best of the best. Even compared to other world-class cities. But we do it in our own unique way.

It’s easy to reflect on how Calgary has changed over the years, but also on how nothing has really changed.

Perhaps we’ve always been this creative, innovative and trendsetting all along?

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