Growth Begins Where Comfort Ends

Some of the more striking things I’ve seen while hiking are the wildflowers. The ones that force their way through rocky crevices, thriving in places where it seems impossible. They don’t have ideal conditions, yet they grow anyway. I think in many ways leadership is similar. The best opportunities often come in the least comfortable places. Whether it was building a team from scratch in the DACH region or building a team from scratch to attack a new vertical, every major leadership milestone in my career started with embracing the uncomfortable.

Building from the Ground Up in DACH

While based in Europe, I was asked to establish and scale Cherwell’s presence in the DACH region. Why was I chosen? I had spent my childhood in Austria. Only problem? I only spoke German like a 16 year old and, at that point, I hadn't used it in 30 years! So there I was - navigating cultural nuances, hiring and managing a German-speaking team (from BDR to Marketing to Sales), and negotiating deals in a language I spoke like a 16 year old. I had to rely on adaptability, trust my team, and find creative ways to break into an unfamiliar territory.

Pioneering in a New Vertical

Later, at Altia, I faced a different kind of challenge, expanding into a new vertical where the company had little brand recognition. This wasn’t just about selling a product; it was about proving credibility in an industry where often prospects didn’t yet know why they needed our solution. So, the discomfort came from uncertainty. This required a more consultative approach, understanding pain points deeply, educating the market, and positioning our value in a way that resonated with an entirely new audience.

These experience shaped my leadership in three key ways:

1️⃣ It reinforced that success isn’t about having all the answers; it’s about being willing to learn fast.

2️⃣ It taught me that hiring the right people, those who align with the mission and bring local expertise, is more important than any personal skillset I could bring to the table.

3️⃣ When there’s no existing roadmap, you have to create one. And that requires resilience, creativity, and a willingness to fail forward.

Don't get me wrong. There were definitely moments of doubt, but discomfort forced me to sharpen my leadership instincts and solidified my belief that leadership isn’t about maintaining control. It’s about being comfortable with the unknown and pushing forward anyway. Every new challenge, every unfamiliar situation, is an opportunity to grow. If you’re not feeling a little uncomfortable in your role, you might not be pushing yourself (or your team) hard enough. The best leaders aren’t the ones who seek comfort; they’re the ones who embrace uncertainty, take calculated risks, and build something great despite not having all the answers.

What’s the most uncomfortable challenge you’ve faced in your career, and how did it shape you as a leader?