What working in Chicago taught me about team building

I’ve been working at Rheaply for a year and half. I interviewed just before COVID-19 was declared a pandemic and got hired immediately after. Given the highly unorthodox circumstances in the world at that time, I should have assumed that my role at Rheaply would be just as surprising. I had no idea I was about to go on an adventure.

As the only hire in Canada, I worked remotely during the pandemic, never having met the team in person. I didn’t mind working from home, at times I found refuge in separating my work and personal life (there was a border between us after all). I became convinced working remotely was the right fit for me, and a way of life that I should adopt. But as the pandemic progressed and we went into lockdown for the 2nd and 3rd time in Toronto, my sense of balance started to erode. The only thing that inspired me was my job and I was quickly starting to lose my sense of self outside of that. 

Luckily, even while working remotely in my basement many miles away, I felt a closeness to our team. I noticed bonds and relationships start to form that took me by surprise given the distance. Through my colleagues, I started to learn alot about Chicago (a city I had never visited) and even more about sustainability (an industry I had never worked in). It was clear: I needed to visit in person. 

Suddenly, I was here: hugging teammates, doing architecture tours & eating deep dish pizza (yes, it was bliss). Similar to my time at Rheaply, this beautiful city has me humbled more often than not. There is an incredible amount of kindness that exists in the streets and an ease to being here (how many of you can say they had a teammate do their laundry?) It can be quiet and incredibly loud in the same minute, and yet always warm and welcoming. After the 3rd time of being asked how my day was by locals in the streets, I proceeded to ask my team in a meeting, “Why is everyone so nice?” “Oh,” they replied casually, “it’s ‘Midwest Hospitality’ ”. 

I know right…there’s a term for it and no one ever said anything. It was just implied. Craziness. 

Like many of us, it feels as though I spent a portion of my life waiting for COVID-19 to pass. So as I rode Divvy bikes, ate Jeni’s and strolled the riverwalk, I started to see what quarantine deprived me of – inspiration. And as I continue to be a tourist in the windy city, here are the reminders it’s given me about how to build powerful teams:

1. Food brings us together

Arguably, the most universal language is food and what better city to do it in? Breaking bread with people opens a door to a very different type of conversation. Between BBQs with friends, food halls, & hot sauces, you start to hear stories of struggle and passion, and most importantly, authenticity. It becomes very difficult to hide your true self as you carry out an activity so essential to your survival. Suddenly, when you are all united at a table for one purpose, the barriers lift and you’re fully present. During our company all-hands, we ate as a full company, broke off into teams, or asked everyone to find somewhere to eat! Some figured it out so well, that during our Scavenger Hunt, one team opted for a 2 hour lunch instead of worrying about winning the race. Way to be in-the-moment Team #2! 

In your next team activity, make sure to break the team off for meals – give them a chance to connect & go slow. It’s a beautiful thing to witness. 

2. Play breaks down barriers

Since coming here, I joined a running club, went swimming in Lake Michigan, tried some dangerously competitive board games (have you heard of Bohnanza?) & zoomed along on an electric bike. All firsts for me and all incredibly energizing. Your brain gets a creativity boost as you lose track of time. You start to laugh deeply and bond over things you don’t expect. You start to see everyone in a relaxed state & a closeness follows. If you’re wondering how to do this for a large group of people in an hour – can I suggest a show at Second City? It will hurt to laugh after a while – well worth it. 

Find an activity to bond over, preferably something new to most people on your team – it will create some solid memories.

3. Balance allows for innovation

There’s a calmness to work in Chicago that I have not seen in many places. There is a common understanding of hard work without compromising having a life. You see this in cafes: someone staring outwardly as they sip their morning coffee…weird or normal? What I’ve come to learn is that instead of worrying about work/life balance, I should worry about intentionality. How do I want to experience this current moment? Better yet, how do I want to remember it? I’ve spent most of my life in a rush to get somewhere, and it’s refreshing to be reminded that there is no finish line. That there is value in just being; in just deciding to not work for a second and have a real conversation. And most of all, there is value in building friendships. 

If you’re bringing the team together, avoid over-scheduling your events. Set aside time for them to work together, in a room, without an agenda. And watch magic happen.

While I will continue to say that working from home has incredible benefits, it’s been motivating to connect with people offline. Going for dinner, hopping on bikes and collecting experiences: those things matter deeply, especially as we grow our teams. It is where my full circle moments came to fruition and where people raised the bar for who I want to become. It is where I was reminded that at work and in your personal life, the people around you should be lifting you & helping you grow. It is where I saw kindness manifest in the simplest of gestures and words. 

And while ultimately I am incredibly grateful for the things I have learned in my role, I am speechless by the kindness of the people I work with. Thanks for everything, Team Orange & Chicago!


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