Learning to Work With Others (Instead of Doing Everything By Myself)

My report cards from childhood have some consistent criticisms: “distracts the class,” “comes late,” and the most common of all, “doesn’t work well with others.”

Shockingly, my parents didn’t care about that. I say shockingly because my parents certainly cared about my report card.

My horrific group work ratings weren’t the only things my parents overlooked. Consistently, I got scores well below 90% (my parents’ expected minimum) in gym, music, and art. I still remember coming home crying one day because I got Cs in those subjects. My mom laughed. She said, “It’s okay. It’s genetic. We’re not an artistic or athletic family. That’s not what we’re good at.”

I suppose that’s how they felt about group work too. Back home, no one taught me to hold the door open for people or to care about others’ emotions. The lessons I was taught, fiercely and perpetually, were: trust no one, always be number one, and don’t ever show fear.

Though I rebelled hard against my parents as a teenager, I took those core lessons with me. I continued to believe that I was athletically and artistically challenged. I stifled my fear instead of working on it. I made independence a part of my personality. I would even quote the report cards when confronted. Hey, if I’ve been bad at group work since childhood, that must mean it’s genetic, right? (I.e. “I can’t help what an asshole I am.”)

Since I began my journey of self-discovery, I’ve been challenging this conditioning. I took up running and yoga. I finally learned to ride a bike. I faced some fears I had accumulated from childhood: being upside down, climbing trees, jumping. I started playing guitar and singing. I’ve worked to publicly share my fears and my journey of facing them.

The group work bit has been harder to challenge.

In my last year of college, I realized that many of my classmates saw group work with me as a free ride to an A. I tried, with no grace whatsoever, to change those patterns. In the end, I ended up doing most of the work last minute and being furious about it.

Since I first started blogging in 2012, I’ve tried to do everything myself. Like this, I learned WordPress web design, basic HTML and CSS coding, graphic design, social media. I have rarely hired people (and when I have, I’ve rarely been happy with the results …here’s one of those rare times). I’ve been functioning as a solopreneur, a one-woman show.

These tendencies haven’t just crept into my work. They’ve also been part of my personal life. I’ve never had a roommate I didn’t resent at some point for not doing as much cleaning as I did. I’ve frequently loaned money that I never received back. And I cannot tell you how many times in my life I have been exhausted, thinking, “I am so tired of doing all the work!”

But how tired was I? Tired enough to clean less and give others an opportunity to notice it was messy and take initiative? Tired enough to set boundaries? Tired enough to not give out more than I was willing to lose? Tired enough to say, “No.” To say, “I can’t”? To say, “I need a break”? Tired enough to actually take that break instead of being productive during it?

Obviously, I wasn’t tired enough.

Last year, I planned a book launch in Toronto for The Art of Talking to Yourself. I had an idea to include others in the event: artists whose work visually represented my book’s contents. This was a step in the right direction, but I still ended up overwhelmed.

Of the five artists who participated, only two were available to help on the day. I didn’t think of how it would affect me to have more people helping. I just focused on doing everything I could myself.

The attendance to the book launch was low. Just when I was starting to get disappointed, Jamie saved the day. He stood outside and pulled in people off the street, promising them free food and inspiration. If he hadn’t done that, I might have walked away with some familiar feelings about how much I got back from what I gave.

About a month later, I was invited to take part in an event run by Daniel, an artist and musician who printed canvases for my book launch. From the moment I stepped into that room, I knew it was a special place. The walls were covered in art and, even before the doors opened, the room was full of people—those showcased in the event.

Something came alive within me that day: an idea. Is this what was possible when people worked together?

After that, I took off travelling again for nine months. I went back to solopreneurship, but my goals for the year were different. I didn’t want to spend all my time working. I wanted to face my fears, ignite my creativity, and explore the big, wide world.

I expected my business to suffer from my reduced working hours, but surprisingly, things went in a different direction. Having less time to work forced me to try to make things more efficient. For example, deciding to go on a four-day trek in Colombia brought me face-to-face with an uncomfortable reality: I couldn’t actually walk away from my business for four days.

There were tools that could help me with this, but they all cost money I hadn’t been willing to spend. I needed to make a decision: did I want to have freedom or did I want to save money? I bought some automation tools. I set them up. I gave myself the gift of freedom.

More opportunities came, and I kept having to make the same choice: was I committed to doing the new, uncomfortable thing to build the life I wanted or was I committed to comfort? I kept choosing the new. Choosing discomfort. Choosing to face my fears.

When I came back to Toronto in October, I reconnected with Daniel. Was he planning another event like the one last year? He wasn’t. I thought about trying to plan one on my own, but something within me resisted. That’s your comfort zone, I told myself. Working alone is the same old, same old.

So, Daniel and I decided to work together. The process was hard for me. With all my triggers around group work, my mind kept trying to convince me why it would have been better to work alone. And I kept having to redirect my thoughts, to choose to think a new, different way.

During one of our first meetings, Daniel said, “Some people are into trying to plan everything, and they just focus on that. They don’t realize that planning is only part of the work. Being able to run an event smoothly when things don’t go according to plan is an important part of it too.”

I kept remembering those words. At my book launch, I didn’t do a good job on the day. In fact, I did very little except talk about my books and sign them. I’m fond of planning, and I’m good at it. But I kept reminding myself of what I wasn’t good at—a skill set which Daniel has in spades.

One evening, Daniel and I went flyering for the event. My plan was to hit up as many gallery receptions as possible and put flyers into people’s hands. But when we entered the first art show, Daniel didn’t do what I had expected. He walked up to the main artist and began a long conversation. At first, I felt lost, but after a few minutes, I followed suit and started talking to another person, who turned out to be the director of the gallery.

Later on that night, we ended up at another reception. Within minutes, Daniel made some connections with new people. I was part of those conversations, but he had started them. Then, he said he had to go.

The first five minutes after he left were overwhelming. There were people everywhere. What was I going to do? Could I approach strangers and get into deep conversations?

It wasn’t until that moment that I realized how much working online had blunted my already hazy social skills. I could send an email to someone I didn’t know, so why was it so hard to just approach someone face-to-face? It wasn’t objectively harder. It was just new, uncomfortable.

That night changed my life. Not only did I overcome my fear, but I also found some incredible vendors and artists for the event, made connections with people whom I plan to work with one day, and stayed up until the wee hours of the morning talking to the gallery owner (with whom I’m now co-hosting an event).

So what was it worth: Daniel modeling those skills for me? Was it a fair trade for the extra hours I had spent flyering? I started to realize that what he had given me was priceless. There was no fairness, and there was no unfairness. There were only his offerings and my offerings. His boundaries and my boundaries. Everything else was magic.

Before the show, another person came to work side-by-side with Daniel and I. A comedian, poet, and button-maker, Anto is a ball of wit and energy. As we were discussing the approaching event a few days beforehand, he said to me, “We are going to take care of all the setup. Don’t worry. You’ve done so much in planning and promoting the event, it’s important that we come through on the day. You just stand at the door and invite all the vendors and artists before the show. We will set it up.”

Watching the cars pull up on the morning of December 16th, I felt like a child patiently waiting for my parents to do the adult work. When was the last time I let myself be in that position? When had I sat back and just allowed myself to receive?

That morning, lots of things went wrong, but I only remember what went well. Jamie took a long cab ride back to our sublet to get something we’d forgotten. Jason, our DJ, brought free breakfast for everyone and refused to let us reimburse him. Jamie and two volunteers, Brooke and Thomas, not only helped set up the market but also ran it in exchange for nothing more than free food and appreciation. Two more volunteers, Yana and Beki, came to help us set up and had to leave before the free food even arrived. Anto not only helped set up the vendor tables but also emceed the whole event. Four photographers and videographers came to document the event, mostly for service trades. We hosted 18 vendors, 8 artists, and 5 performers, all of whom had worked to help us promote the show, sell tickets, and build a loving vibe in the room.

That day, my heart was so full, and my mind was playfully obsessing over an idea that was rocking my world: “I couldn’t have done anything like this alone.”

There’s an African proverb that says, “If you want to go fast, go alone. If you want to go far, go together.” I had put going fast on such a pedestal that I never saw the value in teamwork. Until now.

As I’ve allowed myself to embrace the idea of working with others, opportunities have been dropping into my lap left, right, and center.

The day after the event, I met up with Daniel, Anto, and Avienna (one of our most helpful vendors in selling tickets for the event) to discuss forming an arts collective. We have a name. We have a plan. We have momentum.

Shortly after, Anto and I met up one-on-one. He wanted some advice about editing and the direction of his creative career, and I wanted to thank him for all his help in the show. I knew what I had to give, but I wasn’t prepared for what I was about to receive. When I told Anto that I wanted to start performing, he told me he could help me with that. Within a few days, I was on a stage performing spoken word. It was incredible, and I couldn’t have done it without his guidance.

A few days later, I ran into Yana (one of the volunteers who didn’t even get free food) at a music event a few days after the show and told her some of my ideas about music events. It turns out that she not only has experience with planning those kinds of events but also a huge network of people who can help.

That gallery owner I stayed up talking to? Him and I are now planning a weekend seminar event. He has a two-floor space for us to use, connections to artists all over Toronto (and the world), and a graphic design degree.

I reconnected with a friend from my theater school days. He’s now working for a media company with millions of followers, and we’re brainstorming on what we can do together.

In the meantime, Chris Agnos from Sustainable Human made a video with clips from my audiobook. He has an audience of 2 million and video creation skills that I can only dream about. But I’ll let it speak for itself:

All of these incredible people with resources that I don’t have. For years, I worked on being abundant by maximizing my own skills and resources. But I’ve realized that human beings are the richest resources of all.

I’ve decided to put off travelling this year and stay in Toronto. New opportunities seem to pop up every day. I’m starting to understand why: I had walls put up against working with others. Now that my walls are down, all the incredible opportunities I was keeping at bay are flooding my world. And I’m learning to swim.

The most important lesson here, and it’s one that I keep learning, is that just because something’s been around for a while doesn’t mean it’s permanent, even when it comes to personality. Everything can change. It’s just a matter of understanding why it’s there.

That whole thing about me not being from an artistic or athletic family is nonsense. My mother is a sensational artist and illustrator. She sews. She writes. My dad does woodworking. He used to play guitar. Both of my parents exercise regularly now. They’re both wizards at cooking. It was all just belief systems. Limiting belief systems.

Some ideas have come to us from multi-generational cycles that encourage self-repression and inauthenticity. Will we stand up to those patterns and say, “It stops with me”? Will we choose to make the new, uncomfortable choices? Will we trust where our intuition is taking us? Will we take the opportunities that are available, however inconveniently they may present themselves?

May our eyes remain ever-open to these choices, and may our hearts remain ever courageous to say, “Yes.”