My 2021 Year in Review

Change, Growth, and Connection

Mathilde Leo
9 min readJan 10, 2022

For the past few years, I’ve written an annual review to reflect on the highs, lows, and lessons that marked my year. This process has been cathartic. Once again, I’d love to capture and share how far I’ve come, what I learned, and where I want to go!

2021 year in review, here we go!

🔟 Key moments & milestones

  1. Started the year on the beautiful island of Martinique with my mum
  2. Closed down the product community I had been running for 6 years
  3. Joined Circle the day before my 29th birthday, ready to start a new chapter of my career
  4. Hosted 100+ virtual events and sharpened my virtual facilitation skills throughout the year
  5. Started a relationship in a very unexpected manner and spent the year feeling more loved and supported than ever
  6. Invested in my 4th rental property back in France
  7. Spent quality time with family in my hometown in the French Alps
  8. Participated in the #Tweet100 challenge and made a few awesome internet friends
  9. Launched an exciting new side gig: the Anxiety Parties with Caryn Tan
  10. Said goodbye to 2021 in the world’s capital of Salsa: Cali, Colombia

⬆️ Highlights

What do I make of these experiences? I’ll remember 2021 as a year of change, a year of growth, and a year of presence.

A year of change

New role, new relationship, new rhythm, new routines. So much of 2021 was about embracing change. Back in January, I joined Circle as their 11th team member to lead their burgeoning customer community. After six years growing my own community for product managers, it was time for something new.

It’s never easy to close a career chapter, especially one that involves a community like Jam, which I ran for most of my adult life. I started Jam as a side project whilst at my first ever job. Every year after that, the community grew with me. From a product manager, I became a community builder and a founder. I poured myself into bringing thousands of incredible product people together, and I was lucky to make life-long friendships on the way.

As fulfilling as this work once felt, 2021 was the year I realized I didn’t see myself doing this for another five years. This wasn’t an easy realization. It took the pandemic and a new role to really convince me that the community had run its course. I was no longer a product manager and curating events for product folks increasingly felt like a chore. I no longer cared about the problem I was solving with/for this community and, most importantly, I felt lonely running it. After working for myself for so long, I was craving the buzz of a team. I wanted to work on solving new problems. Joining Circle and winding down Jam became an evidence.

Following the announcement that Jam was closing, my inbox was inundated with all kinds of thankful messages from community members who’d come to our events over the years and remembered them fondly. It felt really good to be reminded that my work had impacted so many people in small and bigger ways. Here are a few of the messages from my feel good folder:

Like me, many people were sad to see Jam go. A few folks asked: “why not pass the torch over to one of your members? Jam can go on!” There was no shortage of Jammers ready to take over, that’s for sure. But, even though the abrupt end of a six year chapter didn’t sit right with me, I needed change more than I wanted continuity. Some of life’s chapters don’t have the end they deserve. And that’s okay. The memories remain.

A year of growth

Jam behind me, I was able to fully transition to my new community role at Circle and press play on my next phase of growth. It felt great.

I quickly immersed myself in the world of online community building, entrusted with the mission of helping creators build highly-engaged, profitable communities. Having never run an online community before, I relied on everything I’d learned from the IRL world, as well as my product management background.

Leading a product-focused community that is growing exponentially is no easy task. There are so many different people to serve, so many directions you can take, and a lot of creative ideas coming from your members every day. Experimenting is key, and so is prioritizing.

One of the first decisions I made was to host weekly events, exclusive to Circle creators. With the community being new, I knew it could be shaped in so many different ways. My assumption was that regular, intimate events focused on getting to know other community builders and learning from each other would help create a sense of belonging. When people belong, they feel at home, understood and supported. There’s no better indicator of success for a new online community. So I experimented with different events formats, from expert workshops to group discussions. One of the experiments quickly stood out. That’s our “Show & Tell” series. Every week, a growing number of creators would join us — eager to discover what their peers were building behind the scenes.

Another successful series was the weekly Office Hours I hosted. These sessions started off as a pragmatic, product-focused Q&A, but they quickly evolved into an intimate gathering of regulars and new folks supporting each other on all things community building, engagement, growth and more. By the end of the year, I had made real connections with many of these people and grown as a community builder from hearing their experiences.

Happy Circlers after our community retrospective workshop.

I hosted over 100 events in the course of 10 months. Not bad for someone who’s secretly crazy anxious before every public speaking appearance (working on it!)

The consistency of these sessions, their open-ended nature and my newly-gained virtual facilitation skills all helped make this shift happen. As a team one, I’m particularly proud of this achievement!

Beyond the community, a lot happened in the Circle world. It was a year of hyper-growth for the company. We grew our team from 11 to 40, raised our series A round with an impressive $200M valuation, launched countless new features, ran successful private betas with hundreds of customers, and leveraged our customer community to continuously build the best product possible.

I’ve been impressed with our speed as a company countless times.

As this article from First Round puts it: “Speed is the ultimate weapon in business. All else being equal, the fastest company in any market will win”. At Circle, I’ve seen first-hand how speed can be turned into a competitive advantage. From how decisions are made, to how meetings are run there’s a bias for action in everything we do. This translates into faster feedback loops across the whole business.

The level of trust and autonomy I received from the leadership team from day 1 has been a key factor in my personal growth this year. Just like everyone else on the team, I’ve had the space to bring my ideas to life and experiment with different approaches.

I feel I’m still at the beginning of my journey as a community leader, and that’s what is so exciting. At this stage, one thing is certain: nothing makes me happier than helping independent creators turn their passion for bringing people together into a profitable business.

A year of connection

Despite being a busy year work-wise, 2021 was marked by a lot of quality time with my loved ones. My boyfriend and I spent a good chunk of the summer in my hometown in the Alps, touring an indecent number of Michelin star restaurants. My mum came to visit us in Lisbon a few times, bringing with her cheese of all kinds and her all-time high energy. We hosted friends over from London, realizing how much we missed the diversity of our friends group there. Cat, my favorite partner in crime, continued to make me laugh until my ribs hurt. My family gathered for Christmas for the first time in years. So many memories were created!

What strikes me is how much I was able to enjoy these moments fully. Unlike the previous year, where my struggle with depression meant I had an absent and heavy mind even in the best of company, 2021 felt light and joyful. What really helped is that I became proactive rather than reactive with my mental health. I started seeing a new therapist every two weeks and together, we worked on untangling my anxiety. In the past, I sought help when it was “too late”. Now I treat my mental health just like my physical health: putting those reps in regularly to build a stronger mind.

In the online world, too, I managed to create space for connection. First, by joining the wonderful support session for community leaders hosted by Danielle Maveal, where I could connect with my peers on a deeper level every week. And then, by creating my own space to help folks feel heard and supported. In December, a twitter conversation with Caryn Tan turned into the decision to host an Anxiety Party, inspired by this old article from Google Ventures and the empathy circles. The feedback following the first one was so heart-warming that we decided to make it a regular thing. Watch this space!

⬇️ Lowlights

The return of the impostor syndrome

Most of the struggle this year had to do with not trusting myself enough. I have some regrets for the year, mostly about second-guessing myself and not making decisions quickly and confidently enough. Impostor syndrome was back. At times, it was like I had lost touch with my strengths, and all the things that made me a natural community builder. I’d instead focus way too much on what I felt I needed to learn, research, or practice in order to feel worthy of my position as Head of Community at Circle. I often deferred action for fear of not “doing the right thing”. And when creators would turn to me for community building advice, self-doubt would often set in. I didn’t feel legitimate.

Towards the end of the year things got better, in part because I received amazing feedback and words of encouragement from community members I had helped throughout the year, and also because I recognized how much of this was a trap I fell into in the past.

In 2022, I’ll strive to find validation from within (a whole agenda!). I’d also love to find a mentor from the community space, someone who’s been there and done it before. (Is it you? Please drop me a line!)

Exercise

I haven’t been as consistent with my training as I managed to be in the past years. Overall I practiced Muay Thai only for a few months when my club reopened, and visited the normal gym on average 2x a week (down from about 4x times last year). It’s important for me to get back into a routine as days where I train are days where I feel more like myself, more focused and energized.

In 2022, I’ll schedule my sessions ahead of time! I’ll prioritize Muay Thai. Commit to two Muay Thai sessions a week (the same ones every week), and go to the gym twice a week including once in the weekend.

Lack of boundaries

Like many people working from home and across time zones, I faced the challenge of the never-ending workday. No one required me to, but I often stayed up late to get more work done — especially after events. I had a really hard time disconnecting in the evening. Being more of a night owl and feeling more creative at night only made this problem worse. I’d often find myself wrapping up a project at midnight, having dinner after that, and going to bed in the early hours of the morning. Not exactly sustainable!

In 2022, I’ll create (and enforce) a work schedule for myself. Mix up the days I choose to work EU hours and US hours, but always enforce a start and an end. Allow a full hour to wind down before bed.

➡️ Looking ahead

There’s so much I’m looking forward to in 2022. First, meeting my colleagues for the very first time at the Circle team offsite in Medellin this week! Bringing on my first team member, becoming a manager and creating an amazing culture within my team. Scaling the impact of everything we do in the community. Saying yes more (hello podcast invitations!). Mentoring and teaching others. Overall, my intention is to trust myself more. Hopefully, by venturing a bit more out of my depth, I’ll be able to inspire more community builders to take their next step towards their own vision of success.

I’m very excited for the year ahead! Happy New Year! 🎉

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Mathilde Leo

Co-Founder& Curator @makingjam ▲ Product Career Mentor ▲ Muay Thai Fighter