Start with the Why: How to Lead a Curiosity-Driven Career

People often change jobs for status, money, or flexibility—but there’s another, often overlooked reason for job changes: Curiosity.

I love seeing curiosity-driven decisions because they come from such a genuine, authentic place. They begin with the humility to acknowledge a lack of understanding, followed by the drive to do something about it—a perfect closed loop.

I’ve noticed that many well-intentioned advisers often dismiss curiosity as a valid career motivator. I think that’s because curiosity is hard to control and even harder to coach. You can’t tell someone what they should be curious about—they have to discover it for themselves.

Coaxing curiosity is a lot less like following a linear path or a predetermined plan and a lot more like coaxing a newly adopted cat out of hiding—it requires patience and space. (And maybe a plate of tuna or cat food.)

Suffice it to say, curiosity has been the biggest driver of my fractional career over the past few years. While many of my fractional peers focus on one domain or specialization area, I’ve embraced variety. Rather than formalizing a consultancy, coaching practice, or startup studio—though I’ve considered each—I’ve stayed a free agent, ready to jump into new projects or industries at a moment’s notice. This flexibility has allowed me to pivot from web2 talent marketplaces to web3 crypto VCs and now into the "AI for good" space in just three years.

Exhausting? Yes. Invigorating? Absolutely. 

Some people skydive out of planes to get that thrill—I dive headfirst into new jobs or projects, often, without testing the parachute first.

The roles I’ve taken weren’t about building a long-term career, but about answering key questions that deepen my personal mission. To an outsider, my path may seem like a whirlwind of indecision, but for me, it’s a deliberate pursuit of understanding. After all, learning isn’t linear—so why should careers be?

Here are the questions that have guided my journey:

Questions that Have Powered My Curiosity-Driven Career Recently

• What does really good operational leadership look like from the inside of a startup?

• What happens at the very earliest stages of how companies get started?

• Where is the next cohort of up-and-coming tech innovators spending their time?

• What, exactly, is happening in the crypto ecosystem, and how will this impact life outside of it?

• What are some opportunities for nontraditional funding models, both to reward individual employees (ie: equity alternatives) and to fund businesses (ie: VC alternatives)?

• Why is there still such a massive disconnect between the digital "haves" and the digital "have-nots" when it comes to technological adoption and progress?

• What's inside the black box of large language models, and what would I need to know in order to feel safe putting my kids in front of an AI?

• How will the accelerated pace of digital transformation inform the way we learn, work, and connect in the future?

In pursuing these questions, I’ve also grown better at identifying where my unique skills can make an impact across the various industries I work in. It’s helped me hone in on my real transferable skills, the ones that carry me through one project team to another. 

It’s worth noting that this "marine corps mentality" only works because I’ve defined a clear north star for my own work: Helping people use technology to elevate how we learn, work, and connect. For me, the title or income bracket matters far less than advancing this mission. The how matters less than the why.

This weekend, I watched my two-year-old, Sydney, discover her shadow for the very first time. As we walked down the street, she looked back over her shoulder and asked, “Where’d Sydney go?” I watched her step into shady spots under the scaffolding and lose her shadow, only to re-emerge, giggling with delight as her silhouette reappeared in the dappled sunlight.

“One more time, one more time!” she insisted, eager to repeat the magic of each passing disappearance.

When’s the last time you felt this way at work—so curious and delighted that you wanted to relive the discovery, again and again?

There’s wonder and delight in learning something new, in the deeply personal yet natural process of getting curious and playing with the boundaries in your own world. Maybe it’s time we all leaned into that sense of childhood wonder—asking not what job we want next, but what questions we’re eager to explore. After all, when you’re driven by curiosity, you can find a home just about anywhere.