30 Conversations | Conversation #6 | Bet on What You Might Learn
What if the biggest risk in your career isn’t taking a chance—but never giving yourself the chance to discover what’s possible?
This week, I had the privilege of sitting down with Natasha Tippett, Director at Creative Destruction Lab, as part of my 30 Conversations project—a personal research initiative exploring the intersection of finance, strategy, commercial law, venture capital, innovation, and leadership.
I was particularly excited for this conversation because Natasha’s career bridges two worlds I am increasingly fascinated by: technical innovation and entrepreneurship. Her journey from engineering to entrepreneurship and eventually to helping scientists and investors understand one another offered a perspective I hadn’t yet explored.
A little about Natasha
Natasha sits at the intersection of science and business, translating ideas between worlds that don’t always speak the same language.
She began her career in engineering, initially imagining a fairly traditional path: climb the ladder, gain experience, and progress into the next role. Then she moved to Australia—and stepping outside her comfort zone broadened her perspective in ways she couldn’t have planned.
Those experiences eventually led her to build a travel agency centred on authenticity, trust, and technology. Later, wanting to understand the business side of entrepreneurship, she found herself working at the intersection of science, startups, and investment.
Today, she helps bridge the gap between highly technical founders developing complex technologies and investors deciding whether those ideas are worth betting on.
Her journey reminded me that careers aren’t always built by following a plan. Sometimes they’re built by following what you learn.
Three ideas that challenged my thinking
💡 1. You don’t need the whole puzzle to take the next step.
In Natasha’s world, scientists and investors often meet with very different questions.
Scientists are trying to develop something that may fundamentally change how we solve a problem. Investors are trying to determine whether that idea can become a viable business worth backing.
Neither side has complete certainty.
Yet both are being asked to make decisions with incomplete information.
That made me rethink how we approach risk. We often assume that taking a risk means being confident about the outcome. But innovation doesn’t work that way. Sometimes the best you can do is gather enough information to make the next decision.
Reflection: You don’t need every piece of the puzzle to decide whether to put the next piece down.
💡 2. Some of the most valuable people are translators.
One of Natasha’s greatest strengths isn’t simply her technical background or business experience. It’s her ability to understand both sides of the table.
She described the learning curve of moving from the analytical mindset of an engineer into a role where she needed to translate between scientists, founders, and investors.
Rather than trying to become the smartest person in the room, she learned by being in the room, listening to recurring questions, identifying common concerns, and recognizing the gaps between how different stakeholders understood the same problem.
Over time, those observations became expertise.
Reflection: There is tremendous value in being the person who can connect two worlds that otherwise struggle to understand each other.
💡 3. Maybe your career isn’t supposed to fill your entire cup.
I’ve grown up around the idea that career progression means climbing the ladder: get the job, earn the promotion, move up, repeat.
But Natasha challenged that model.
Your career is one part of your life, not necessarily the entirety of it. Different seasons of life may call for different priorities, and a fulfilling career doesn’t have to look like constant upward movement.
Sometimes the right move isn’t the one that advances your title. It’s the one that gives you exposure, courage, learning, or perspective that you didn’t have before.
Reflection: Instead of asking whether my career is moving upward, I want to ask whether it’s helping me become someone who can move forward.
My biggest takeaway
Every conversation in this project has reinforced that careers are rarely linear, but they can be intentional.
The lesson I’ll be taking from this conversation is:
“You don’t have to know exactly where you’re going. You have to be willing to learn your way there.”
Natasha’s career reminded me that some of the most valuable experiences don’t announce their relevance when you’re living through them.
The move that feels like a detour might become the experience that gives you your next perspective. The skill that seems unrelated might become the bridge between two worlds. The uncomfortable decision might simply be expanding your map.
Maybe the goal isn’t to have the perfect career plan.
Maybe it’s to keep building a career you couldn’t have imagined at the beginning.
How I’m applying this
Learning only matters if it changes how we think or act.
Because of this conversation, I’m going to:
- Take more calculated risks for the learning opportunity, not just the potential outcome.
- Continue developing my ability to translate ideas across finance, strategy, innovation, and business.
- Stop treating career detours as wasted time and start asking what each experience is teaching me.
I’m excited to see how these small changes shape my own career journey.
A thank you
Thank you, Natasha, for your generosity, openness, and willingness to share your experiences. I truly appreciate your time and the perspective you brought to this conversation.
Conversations like these remind me that sometimes the best career lessons come from people whose paths look nothing like the one you imagined for yourself.
Help me reach 30 conversations
This is Conversation #6 of 30. (20% of the way!)
My goal is to speak with professionals across:
- M&A and Commercial Law
- Venture Capital
- Investment Banking
- Corporate, Economic, Industry and Development
- Corporate Strategy
- Innovation & Entrepreneurship
- Family Offices
- Economic Development
- Luxury and Consumer Strategy
- Fashion Business
- Media, Entertainment and Tourism Business
If you work in one of these areas or know someone whose perspective would add to this project, I would love an introduction.
Every conversation is helping me better understand how organizations create value through capital, strategy, governance, and innovation, and I hope these reflections provide value to others exploring similar career questions.
Who do you think I should speak with next?
#30Conversations #CareerDevelopment #Leadership #CommercialLaw #MandA #VentureCapital #CorporateStrategy #Finance #Innovation #Mentorship
Six conversations down. Twenty-four more opportunities to learn.
