An Inspired Chat with Olga Ten of San Francisco and Amsterdam

Olga Ten shared their story and experiences with us recently and you can find our conversation below.

Hi Olga, thank you so much for taking time out of your busy day to share your story, experiences and insights with our readers. Let’s jump right in with an interesting one: Are you walking a path—or wandering?
Right now, I’d say I’m definitely wandering. For most of my life I followed a very clear path, always focused on goals, targets, and trying to control outcomes. Allowing myself to wander was a big shift—and honestly not an easy one. But that’s when the magic started to happen. Letting go of outcomes opened up space for unexpected opportunities, and paradoxically, that’s exactly when my business began to grow and take off in a completely new and exhilarating direction.

Can you briefly introduce yourself and share what makes you or your brand unique?
I’m the founder of Upmarqt, a peer-to-peer professional development community. Too often, we work in silos—even though we’re tackling many of the same challenges. Upmarqt was built on the idea that we can learn so much more from each other, and over the past year we’ve pivoted to bring that vision to life.
What makes us unique is the hyper-interactive design of our learning events, workshops, and courses. Professionals don’t just sit and listen—they experiment, practice, and walk away energized, inspired, and equipped with new up to date skills. At the core of everything we do are authentic human connections, combining offline and online experiences so our community truly gets to know each other.
We’re about to launch our first hybrid course for professionals who want to understand AI in a practical way—well beyond just ChatGPT—and apply it directly to their work. For us, it’s never just about “interesting” conversations, but about creating real learning experiences that stick and drive change.

Okay, so here’s a deep one: What part of you has served its purpose and must now be released?
Self-doubt has been both my fuel and my limitation. On one hand, it pushed me to achieve; on the other, it sometimes slowed down how far and fast I could grow. This past year, though, I’ve received so much validation that what I’m building with Upmarqt is genuinely needed—and that’s been a real confidence boost. Even now, when I launch something new, that little voice asks, ‘But what if no one needs this?’ The difference is, I remind myself I’ve been here before, and it worked. That reminder frees me up—suddenly my creativity flows, opportunities appear, and things start to click.
It’s tough to keep believing in yourself when you’ve tried so many things that didn’t stick. But then, out of the blue, something does—and it changes everything. I still believe your internal why has to drive you, but I’ve also learned that a bit of external validation goes a long way in keeping your confidence on track.

Was there ever a time you almost gave up?
Absolutely. When the second pivot of Upmarqt didn’t work, investors told me it wasn’t a backable idea. I had already invested so much—attending countless conferences, networking events, trade shows, and pouring time and money into early product versions that never really took off. Even a few months into our latest pivot, I found myself questioning if this was truly the right path.
What changed everything was the consistent success of our learning events—and, more importantly, participants telling us that our events genuinely changed their lives. That validation made it clear we had product–market fit. Today, with a brilliant team and exciting initiatives ahead, we feel confident about the direction we’re taking and energized about the future.

Sure, so let’s go deeper into your values and how you think. What’s a belief you used to hold tightly but now think was naive or wrong?
I used to believe that having everything under control was the key to success. But I’ve realized it can actually be very limiting. When you feel the need to control every aspect of your life—or your business—it becomes stressful and leaves no room for unexpected opportunities.
In business, having a vision matters, but setting rigid targets for things you can’t truly control is often pointless and discouraging. With Upmarqt, the current idea came from a consumer insight and global trends, but it wasn’t our core proposition. What really shifted things was recognizing what people actually wanted. That insight allowed me to let go of the old idea, pivot quickly, and openly admit when something wasn’t working.

Okay, so let’s keep going with one more question that means a lot to us: Are you tap dancing to work? Have you been that level of excited at any point in your career? If so, please tell us about those days. 
Absolutely! I truly love what I do and the impact it creates. Back in my corporate career, I was lucky to be part of a brilliant team where everyone’s strengths complemented each other. We had fantastic relationships, we were empowered to create outstanding products, and we had the freedom to be bold and creative with our launches. I could see the tangible impact of my work, and I was surrounded by highly competent, engaged people—it was energizing. That’s exactly what I love about Upmarqt too: working with a great team, driven by a purpose that genuinely makes a difference.

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