One year in the outside

Happy birthday to us Outsiders—from launch day in March 2018 to now, we’re into our second year of existence. Tim and I got together to reflect on such a big, challenging, and exciting year—one rich with expansion and travel, new movements and longtime colleagues.


On jumping on a wave

Tim: I’ve been thinking about our metaphor for the year. Entrepreneurship is often positioned as active, and not passive—we drive it, make it happen, push our way forward. But for us, the past year has felt more like we’ve been surfing a wave that was already underneath us. It doesn’t feel like we created the wave. It feels like we’re riders, not makers.

Tues: Sometimes, it’s felt like we’re being carried along in a pretty overwhelming way. We have a lot to do, and quickly. But more often, we’re being lifted up by something incredible. There’s an enormous sense of wonder and gratitude. But yeah.. it doesn’t feel like we launched a new thing. It feels like we branded a joint effort that was already happening. 

Tim: Yes! We’ve spent the past year adding structure and collaboration to the momentum that was already in-play. It’s much like what we both already know about change—the conditions and opportunities are already there, flowing. We are organizing on top of it. 

On resisting bigness 

Tim: Given that we’ve both spent most of our career as independents, both of us have an instinctual resistance to growth for growth’s sake. That’s not the assumed path. But despite that intention, the past year has brought some big projects and clients. It’s required us to think about how we delegate, share, and restore the energy of The Outside. The people who work with us are all dispersed independents. We’re a remote team, and we don’t see any need to formalize as anything more than that. We’re operating at a high level but in really agile ways. 

Tues: There are many reasons we want to stay small and connected. Neither of us are interested in the full-time pitching and landing of consultancy work, and then sending in junior people to do the work. We might make more money that way, but being closers is just not why we’re here.

We could totally grow and take on more work, but there’s the question of quality control. We would have to figure out how to propagate the DNA of the work. That in itself would be a huge effort, given that the way you and I show up is the essence of this business. But even if we were able to train teams of Outsiders to be like us, where would that leave us? Mostly, I don’t want to be big because the bigger we are, the further you and I are from the work.

On the constant of equity

Tues: When we launched, we put a stake in the ground with equity at the centre. I thought it would be a year of building, then stopping and reflecting and deciding if we want to continue, a see-what-happens kind of thing. I was sure it would be a constant in our work but I wasn’t sure how. But now, a year in, equity is still central. This feels good. 

Tim: Every now and then we would find imbalances of race, gender, economics, or access, or power falling off the table. We have to bring them back to the forefront again and again.  

Tues: No one says no to inclusion, but once you get into the work of it, it takes effort to incorporate voices and perspectives that haven’t been heard before. We are getting better at noticing when it needs to be centred again. It’s not enough to practice the rhetoric. This is a truly ongoing exploration.

On the last year’s biggest lesson

Tim: I often find the things that make me worry most don’t turn out to be anything at all—and the things I didn’t anticipate pop up as being much more challenging. As we neared to launch day, I thought our biggest concern would be building out the systems and structures to run the business. But once you’re underway, systems and structures just sort of erect themselves out of need. You give it a shot, inventing the way you think you might like things to be done. Then you notice what could be better. Then you iterate. The tactical underpinnings of business are not a finite thing. We template and retemplate our approach every day.

What I didn’t anticipate was the constant tension of securing and managing our relationship as partners in this business. We had a strong friendship coming into this work, but now, we work with multiple teams and projects. We have to schedule in time to be able to connect as mates. If we don’t do that, a lot of the fundamental DNA of the work begins to feel shaky.

Tues: Yes! Friendship is the relational fabric that requires real attention and care when we’re working together at this scale and with such complexity and intensity. The tenor of our work makes our connection that much more important. I think we’ve become good at putting any uncertainties or frictions on the table so they stay open and healthy and clean.

The work has accelerated so much – it’s a deepening of our understanding of what it means to build relationship. It’s almost like the old ways were no longer sufficient. We are busy with logistics, but we can’t let relationship fall off the back of the truck. The care and attention we bring to our work is a daily thing we live. It’s not curriculum or rhetoric.

Imagining next year’s focus

Tues: With our first year behind us, I see confidence in prototyping as a key deliverable of our work. I’m looking forward to our own practice of how distributed teams work and evaluate their development—and helping others practice the same.

Tim: Communications will be big. We are learning so much about going from normal, traditional communication to sharing and evolving our thinking. We need to help our clients honour the process, honour the uncertainty, and seek clarity.

Tues: Our gazes tend to be in different directions, and we’re good as business partners for that reason. Either way, we know we have to keep practicing depth.

The fortune cookie

Tim: I’d like to open a fortune cookie about the next year and have it say: You are fulfilled, not frenzied. You are happy and healthy, and your work makes the space for you to be all those things.

Tues: I’d like mine to be about us—a group of Outsiders—laughing and having a good time together. I want more of those moments where we’re able to look around at one another and say, Look what we did! More of our extended crew, clients included, feeling great together. I think that’s how it feels when we find the right balance of growth and peace, and staying close to the work. I want us to build a platform for us to say yes more often without burning out.

To those who helped

Tim: I’m so thankful to so many people for the past year. I’ve done a lot of deep personal work so I can show up despite being deeply destabilized as an entrepreneur, as is the nature of entrepreneurship. I want the excitement and growth and risk-taking as well as the peace and the balance. I’m grateful to my wife for great conversations, my kids for kicking the ball around, and my dog for the walks. It’s our most intimate moments that keep us connected to why the work matters.

Tues: I’ve been grateful this year for my good friends who have checked in with me so much over a year of big change. You’re right that this year has felt very inward-facing as well as outward.

Tim: There are also circles of elders who are cheering us on—almost too many to mention. Most are not doing it deliberately, but they’re just people who hold the emergence of The Outside in an almost invisible, loving way. I really appreciate all those people.

Tues: It feels like a community of change—like a cohort of practitioners, whether they’re clients or fellow facilitators. We learn so much from them all. And of course there are the people who help us all make it happen behind the scenes, such as Jen McSween, our Operations Manager. She’s up front with us a lot, and carries the water with us in a lot of ways. Beyond all the things the people in our circle do, they believe in us, anticipate us, and indulge our sense of humour. There’s so much heart in this work. We’re very lucky that everyone around us brings it along with them just as much as we do. 

Tim: Happy birthday, Tues!

Tues: Happy birthday, Tim!

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