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This month's Odyssey Insights piece comes from Caren Robb, our VP of Finance. As she approaches a milestone birthday, Caren reflects on a career built across finance leadership roles, and a lesson that took her years to learn: that some of the most meaningful contributions in a career are never the ones with your name attached to them.
“As I approach my 50th birthday, I've found myself reflecting on the decades I've spent building a career. Like many milestone birthdays, it naturally makes you look backwards before you look forward. I find myself thinking less about what I've achieved and more about what has shaped me, and perhaps more importantly, what kind of contribution I want to make over the years still to come.
Looking back, one realization has surprised me. Early in my career, I was focused on one thing: becoming the leader.
Like many ambitious people, I believed success was measured by titles and position. The next promotion. Managing a larger team. Sitting at the head of the table rather than around it. Leadership was the destination, and every career decision was a step towards it.
Then something happened.
The more experience I gained, the less interested I became in chasing leadership itself. Instead, I found myself chasing experience.
I wanted to work with exceptional people. I wanted to understand what great leadership looked like, and, perhaps more importantly, what poor leadership looked like. I became fascinated by watching how different leaders made decisions, inspired people, navigated uncertainty and responded when things didn't go to plan. Every leader I worked with taught me something, whether through admiration or caution.
Without realizing it, I had become a student of followership. It's a word we don't celebrate enough. It often conjures images of obedience or simply doing what you're told. Yet the best followers I've worked alongside have been anything but passive. They have challenged thinking, asked difficult questions, offered different perspectives and quietly influenced outcomes without ever needing the spotlight. In fact, I've come to believe that organisations spend far too much time talking about leadership and nowhere near enough talking about followership.
Every leadership programme teaches us how to inspire others. Very few teach us how to support someone else's leadership well.
One of the biggest lessons I've learned is that influence doesn't always come with authority. Some of the most rewarding moments in my career haven't been when I've been the one making the decision. They've been the moments where I've earned enough trust with a leader to challenge their thinking, give honest feedback that changed a behaviour, or simply be there when they needed someone to listen.
Sometimes it was a question they hadn't thought to ask themselves. Sometimes it was an idea that started as a passing conversation and quietly became part of the strategy. Sometimes it was nothing more than offering a different perspective at the right time. Those moments rarely came with recognition, but they've often been the moments where I've felt I've made my greatest contribution.
Those moments rarely make it onto LinkedIn. There isn't a promotion announcement for quietly helping a CEO see a different path. There isn't a press release for changing the direction of a business through one thoughtful conversation. Yet I've come to realise those quieter moments often create the biggest ripple effects.
As my career has evolved, I've realised something else. The leaders I admire most are also exceptional followers.
A CEO follows a board. A board follows its shareholders. An executive follows a strategy. A founder follows the needs of customers. We all move constantly between leading and following depending on the circumstance. They're not opposite skills, they're complementary ones.
Perhaps that's why humility matters so much.
Following well requires confidence, not insecurity. It means putting the success of the team ahead of your own visibility. It means being willing to challenge respectfully, then commit wholeheartedly once a decision has been made. It means recognising that your impact isn't measured by who gets the credit, but by the outcome you've helped create.
As I look ahead to the next chapter of my career, I'm not aspiring to have all the answers. I'm still learning, still observing and still being shaped by the remarkable people I have the privilege to work with. If anything, the past years have taught me that leadership is less about standing in front and more about knowing when to step forward, when to step back and when to help someone else succeed. I'll still celebrate promotions, new roles and career milestones. They're important, and they deserve recognition. But increasingly, it's the quieter achievements that stay with me.
The conversation that shifted someone's perspective.
The trust that allowed honest challenge.
The moment an idea took root because people felt ownership rather than instruction.
Perhaps we've become too obsessed with producing more leaders.
Maybe what organisations really need are more people who understand that leadership and followership are not competing ideas. One gives direction. The other gives momentum.
Some of the most meaningful contributions we make are not always the ones with our name attached to them. They are the ones that quietly enable others—and, in doing so, move all of us forward.”
Caren leads Finance at Odyssey, where she's spent the past several years building the systems, teams, and rigor that let a fast-scaling, fully distributed company operate with discipline across 15+ countries. Her reflection here is a reminder that the strongest finance leaders, like the strongest leaders anywhere, often do their best work quietly, in service of someone else's decision.
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