The Personal Innovator’s Dilemma
What careers and companies have in common: evolve or get left behind
The New Reality of Disruption
There's a growing unease many of us feel...a sense that the old career playbooks are failing.
At companies like Shopify and Duolingo, using AI isn’t optional — it’s now a factor in hiring and performance reviews.
For me, it crystallized when I realized the SaaS benchmarks I’d relied on for years just didn’t apply to AI startups. The models broke.
You've likely heard the new conventional wisdom:
"You won't be replaced by AI. You’ll be replaced by someone who knows how to use AI."
It sounds catchy, and it's true to a point.
But it dramatically undersells the seismic shift we're facing. This isn't just about adding a new tool; it's about questioning the very foundations of our expertise.
It's the personal version of the Innovator's Dilemma.
When Success Becomes Your Biggest Obstacle
The Innovator's Dilemma is a concept I learned at Harvard Business School, coined by Professor Clay Christensen.
In business, it describes how successful companies often fail to adapt to disruptive innovation. Examples are everywhere:
Kodak doubled down on film quality while digital photography transformed the market.
Blockbuster optimized DVD rentals while Netflix pioneered streaming.
Toys R Us expanded floor space while Amazon revolutionized online shopping.
The common theme?
They relied on what had worked well before, and assumed it would keep working. Their strengths became their vulnerabilities.
But this isn’t just about companies.
It’s about individuals, too.
The Personal Innovator's Dilemma
The individual version of this dilemma is even more threatening because our careers don't have the runway of a large corporation. Examples are everywhere:
The software engineer who insisted on writing everything from scratch, while peers used AI to accelerate development.
The journalist who resisted building personal audiences through newsletters and podcasts.
The marketing executive who mastered traditional campaigns, but is behind on SEO, growth hacking, and the creator economy (and now, AI-driven visibility).
Each faced the same challenge:
Stick with what made them successful before, or invest in learning the skills of the future, even when it feels risky and uncomfortable.
My Own Confrontation with Disruption
In my investment work, I had this moment.
For years, I relied on standard SaaS frameworks and benchmarks: CAC, LTV, retention, growth rates. They worked, until I met AI-native companies.
Suddenly, the models broke.
These companies scaled differently. Their cost structures were different. User behavior looked nothing like the SaaS norms.
When I first encountered AI companies, I tried forcing them into my existing models. The results were nonsensical. These companies had different revenue and cost structures, exponential rather than linear scaling potential, and much less constant user retention.
I had a choice: defend my existing expertise or admit I needed to develop new frameworks. It was humbling.
So, I began the messy process of evolving, a journey that's far from over. It means continually:
Diving deeper into how AI can augment the kind of work I already do, ex: financial analysis, market research, and strategic thinking.
Learning how to automate repetitive workflows that previously ate up hours.
Questioning whether old metrics still matter in an AI world and what actually matter.
Learning how to code and how AI agents function from a technical perspective, even without a technical background.
It is an ongoing, slow, and sometimes frustrating process, but I’m also energized by it.
Rethinking More Than Just Work
This confrontation with disruption in my own work hasn't just changed how I work; it's shifted how I think about preparing future generations.
If I imagine educating my (future) kids for this new world, the focus shifts dramatically:
Instead of just memorizing historical facts, they could learn to use AI to research, compare, and synthesize different sources and points of view.
Instead of static coding lessons, they could learn to code by using AI to co-create a game they would actually want to play, combining creativity and technical skills.
Instead of vocabulary lists, they could leverage AI tutors for immersive, real-time conversational practice in new languages, exploring culture alongside.
In a world where information is abundant but judgment and curiosity are scarce, I believe the most valuable skills will be:
Knowing how to learn
Thinking critically
Building creatively
What It Means for All of Us
Whether you’re a founder, operator, freelancer, or employee, the challenge is the same:
Are you evolving faster than the tools and technology around you?
Ask yourself:
Are you using the newest tools in your field before you’re forced to?
Are you spotting early shifts, or only reacting once it’s obvious?
Are you willing to look a little inexperienced again to stay sharp?
Ultimately, the greatest risk today is not trying something new. It's assuming that what got us here will be enough to get us there.
Your Anti-Complacency Challenge
Complacency is the career killer in this environment. Here’s a challenge for you to proactively inject some productive discomfort into your routine:
Spend 30 minutes this week using a tool you don’t understand yet.
Ship something publicly before you feel fully ready.
Ask someone younger what tool, platform, or trend you’re overlooking.
It will feel inefficient, and maybe even embarrassing.
That’s the point.
Because the greatest professional risk today isn't trying something new and failing. It's succeeding at something that's becoming irrelevant.
What are you learning to disrupt yourself?