My 2022 Year in Review

Mathilde Leo
9 min readDec 30, 2022

It’s that time of the year again! Like many people, I welcome the last few days of the year as an opportunity to look back in my rear-view mirror and reflect on the last twelve months. 2022 has been an intense and rewarding year. And that’s perhaps why it went by so incredibly fast.

First, let’s look at the highlight reel:

  • 🇨🇴 Started the year in Colombia, meeting the Circle team IRL for the very first time
  • 🥳 Celebrated my 30th birthday in a beautiful restaurant overlooking Medellín with my partner and colleagues
  • 🌱 Hired my first 2 team members and grew loads in my role as Head of Community (I share why in this year in review!)
  • 🎙 Spoke at 2 virtual summits hosted by Circle, recorded 2 podcasts (my very first ones) & spoke at 1 IRL event
  • 🥑 Hosted a Community brunch at my favorite restaurant in Lisbon with some new friends from the community space
  • 🧪Experimented with tons of new community programs for the Circle creators and experienced a few successes
  • 🏠 Made a new property investment and paid off the loan for the first flat I ever bought
  • 👩🏻‍💻 Completed the Breakthrough Facilitation course to brush up my virtual facilitation skills
  • 🇫🇷 Took my best friend on her first trip to Paris and had an absolute blast
  • 🇹🇭 Completed a 3-month online course to learn Thai (yes, including reading & writing thai script)
  • 🧘🏻‍♀️Never felt more grounded & balanced. (Is therapy paying off? Seems like it!)

As I write these words, I’m packing my suitcase for a trip to Thailand — the first in many years! That’s perhaps why I feel like continuing this year in review with an analogy:

2022 was like running up that hill in Phuket.

You might think this is a Stranger Things reference. It’s not. Let me explain.

If you know me, you know that one of the most defining experiences of my twenties was training and fighting Muay Thai in Thailand. If you don’t, well, that’s where you’d find me every winter. I’d join a training campaign for a month and train every day, twice a day, alongside professional fighters.

My first week at the camp would always be the most painful. My shins would be covered in bruises. My body would ache as I adjusted to the heat and the insane level of cardio required to keep up with the intense training regimen. There was also this run. ‘The Big Buddha Run’. It was like a rite of passage for new fighters: you would join a group at 6am on a Saturday morning at the bottom of a hill. Your challenge was to run 5km uphill, nostop, to reach the big buddha statue at the top and Phuket’s most impressive viewpoint. When I say “uphill”, you need to picture the steeper hill you’ve ever been on. Inclination 15 on the treadmill. That’s what I’m talking about.

The first time I did the Big Buddha run, I gave up halfway. It was so hot. I was in pain. My legs were still sore from training the day before. I felt so disappointed.

The second time, though, after weeks of consistent training, it was a different story. I was able to run alongside the pro fighters and reach the top of the hill — sweaty and happy. 2022 was like my second Big Buddha run. Not effortless, but not painful either. A year of growth and achievement — only made possible by the consistent work and effort that preceded it. Let’s unpack that a little!

Building self-confidence at work

The intention I had for 2022 was to ‘trust myself more’ and I’m happy to say: mission accomplished! It’s not always easy to navigate the uncertainty and fast-changing environment of a high-growth startup. When almost everything you do is new and you need to reinvent your role every three months, there’s always this lingering question: “Am I doing this right?”. In hindsight, it’s easy to answer this question positively. But when you’re in the weeds, juggling all the things and struggling to find the time to look at the big picture, self-doubt often cripples in. How do you break free?

As unsexy as this sounds: it just takes time. Trusting yourself is a process. It requires you to show up every day doing your best — even if you don’t have all the answers. Doing things because they feel right, not because you have the perfect plan. In other words, trusting your gut, which is nothing more than the sum of all your past experiences. And as uncomfortable as it was, I did a lot of that throughout the first half of 2022. Gradually, I noticed that I started feeling more confident in my role. I second-guessed myself less. I participated in meetings more. I accepted more public-speaking gigs… but the best outcome of all was that I advocated for the one thing I needed to make a real impact: a team!

Building my team & giving away my legos

Managers own the job of creating great teams. After running Circle’s community function solo for over a year, it was time to build mine. After wearing all the hats, it was time to create dedicated functions. I was excited. I decided to organize my team around two pillars: Community Education and Community Engagement. Like two sides of the same coin, the two conditions for a product-led community to thrive. It wasn’t enough to give Circle users a place to have discussions and share experiences about community-building. I knew we would need to go a step further: educate, connect, and inspire to accelerate the success of our community builders. In addition to ‘leading by example’, ‘educating through co-creation’ became one of my guiding principles. Rather than creating all kinds of resources or programs ourselves, my future team would need to create the conditions for our community members to participate in value-adding ways and teach others — even if they’re still in the process of figuring out how to build a thriving community. With these loose principles in mind, I drafted my first job description for a ‘Community Education Manager’ role — one that I felt encapsulated the biggest needs of the community at that point in time. (I should say I rewrote it about 10 times until I felt happy!) But the hardest part had yet to start: recruiting the right people!

I learned the hard way how time-consuming recruiting can be. One mistake I made was not making it my #1 priority. This saw me spending months sifting through hundreds of applications, doing a lot of sourcing on LinkedIn, learning how to sell Circle and my vision… all while running all of our community programs and onboarding new team members. Needless to say this wasn’t very effective. Another mistake I made in the process was not keeping my pipeline full enough. I would get excited about a candidate thinking they were “the one” and pause my conversations with other folks… not realizing that a promising conversation doesn’t always lead to a signed contract. And then there was interviewing — a sport I was completely new to and that I found rather draining. How does one assess someone’s past experiences, vet for soft skills as well as cultural fit — all within a 45 min conversation? I should mention that since then, Circle has hired a wonderful Head of People and an internal recruiter who have made this process SO much easier! Big kudos to them!

As long-winded as the road was, I couldn’t have hoped for a better outcome. The person I ended up hiring turned out to be the perfect fit for this role — someone driven by customer empathy, the desire to consistently deliver great work and to grow in her role. All of this is to say: new managers, if you’re deep into yet another round of interviews, keep it up! The perfect match will show up. Not long after, I was able to hire our most engaged community member as our new full-time community manager and the person tasked to level up our engagement strategy (how fitting!)

My small but mighty team was assembled and a new chapter of the Circle community was about to start. (Aka, the real work). I was thrilled!

Becoming a manager (and attempting to be a good one) meant I had to take a pretty significant step back from my day to day hosting events, building relationships, running product betas and all the likes. I needed to shift from doing to guiding. Share problems to solve rather than solutions… while still putting enough “meat on the bone” to inspire the team and get us all moving in the right direction. I was blown away by the results.

Looking back at the past six months, I’m incredibly proud of everything the team achieved. I can confidently say the value created by the Circle community has skyrocketed thanks to the passion and care Emma and Pedro have consistently put into their work. We’re well on our way to building the most supportive community for community builders — all while making community the heartbeat of everything we do at Circle. As the company grows, empowering every single team, from Product to Marketing, Sales and Customer Success with a community-led mindset is going to be one of the most exciting parts of my role as Head of Community.

So, 2022 showed me the importance of building together rather than going solo, but it also taught me how important it was to give away my legos. In other words, let go of some responsibilities — the lego tower I had started building — by letting the new folks joining the company take over in order to take it to new heights. When I joined Circle, almost exactly two years ago, we were a team of 10 serving a thousand early adopters. Fast forward to today, we’re close to 100 team members serving a much larger customer base. Along the way, a lot of the areas I used to own turned into dedicated functions. Rather than seeing that as a threat, the “giving your Lego” mindset is all about learning how to adapt and pick up new blocks to build something even bigger and better.

This is all a process and I still have a lot to learn. While some aspects of being a team lead come naturally to me, informed by my own experience of being managed and the values I carry, there are plenty of others that are new to me. I’m very grateful that I get to learn from the very best, people like Sid, Rudy, and Andy — Circle’s co-founders who I have the chance to work with every day — but also Tim and Mel who joined the Circle leadership team this year and showed me, through conversation and example, what effective and thoughtful leadership could look like.

Building pockets of belonging

There’s something special about being in a role where you get to play a small part in the success of thousands of community builders, indirectly impacting millions of people through the sense of belonging created in these online communities. Having met some of these wonderful people IRL this year, I took the full measure of how important our work at Circle is. We’re not just building software. We’re helping people create pockets of connection and belonging. When we share the stories of creators who have built a thriving community, we ignite that same passion in many others. When we co-create resources with our creators, we show there’s not one best way to build a community business, but many different paths. When we support, guide, and motivate an aspiring community builder, it’s many more people we indirectly impact. All in all, 2022 was a year where I myself felt a deep sense of belonging — through my team, the company I work for, the communities I helped build, the ones I joined, and my local community here in Lisbon. It takes many different pockets of belonging for someone to feel at home!

So, what’s next? Rather than sharing goals or resolutions, I like to end my year in reviews with a theme to guide me in the year ahead. My one word intention for 2023 is Flow. Mihaly Csikszentmihalyi describes the flow state as the feeling where, under the right conditions, you become fully immersed in whatever you are doing. The flow state is intrinsically rewarding. It’s also immensely productive. That’s what I want for myself and my team: a year where we all feel fully engaged, aligned, and inspired to do our best work. A year of flow!

Wishing you all a happy new year!

A trip down memory lane

Work highlights

--

--

Mathilde Leo

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