A few months ago, I was wrapping up another high-intensity international trip with consecutive workshops when I caught myself wondering—Am I really doing what I’m best suited for?

It wasn’t the first time I had this thought.

While I’ve built a career that many would consider ideal—helping startups scale to billion-dollar valuations, working on high-impact projects, and maintaining my independence—I still find myself questioning whether I’m truly optimizing for my strengths and long-term happiness.

The challenge is, I don’t want to put myself on a trajectory that I wouldn’t enjoy or that doesn’t play to my strengths. Over the years, I’ve seen many people optimize for money, prestige, or external validation, only to end up in careers that drain them. I don’t want that to happen to me.

I also know I only get one life, and I want to make sure I’m making the most of it. I don’t want to wake up in ten years realizing I was on autopilot, doing work that wasn’t fulfilling or aligned with what I do best.

Recently, I listened to Lenny’s Podcast interview with Bob Moesta, where they discussed his new book Job Moves. Bob’s insights into how people evolve in their careers inspired me to take a step back and go deep on myself. I wanted to figure out:

• What am I really great at?

• Where do I struggle (what drains my energy)?

• How should I structure my work to maximize my strengths while minimizing my weaknesses?

And to do it, I used ChatGPT as my thought partner. What followed was one of the most valuable self-discovery exercises I’ve ever done.

Step 1: Analyzing My Personality with the Enneagram

A few years ago, one of my forum mates in YPO (Young Presidents’ Organization)—a CEO leading a team of nearly 1,000—encouraged our small group of business leaders to take the Enneagram test. She shared that she had her entire team complete it and found it valuable for improving collaboration and self-awareness. I found it incredibly enlightening. It helped me better understand myself, my tendencies, and why I gravitate toward certain ways of working.

Since I had already generated this pretty solid overview of my personality, I figured it would be helpful to include the results in this exercise as a starting point.

My strongest type was:

🧠 Type 5 (The Investigator) – Deep thinker, highly independent, prefers analysis over collaboration.

Additionally, I also had strengths in three other types, which helped shape my approach to work:

🏆 Type 3 (The Achiever) – Goal-oriented, driven, competitive, success-focused.
💪 Type 8 (The Challenger) – Assertive, decisive, direct, and unafraid to take control.
🔍 Type 1 (The Reformer) – High standards, disciplined, wants to improve everything.

Looking at these results, it immediately made sense why I had built my career the way I did:

• My Type 5 dominance explains why I thrive in deep, independent work. I prefer analyzing problems on my own rather than collaborating in real time.

• My Type 3 side makes me obsessed with results. Efficiency, execution, and impact drive me.

• My Type 8 strengths mean I don’t like being constrained. I prefer autonomy and control over my work.

• My Type 1 traits make me naturally push for high standards. I focus on improving everything I touch.

Step 2: Using AI for a Deeper Analysis

But an Enneagram score is just a starting point. So, I had ChatGPT guide me through a structured Q&A process to dig deeper into how these traits play out in my real work life.

My Prompt to Initiate the Q&A Process:
💬 "I just uploaded my Enneagram results. I want to use ChatGPT to help me identify my core strengths and weaknesses and how I can optimize my work structure to maximize my strengths while minimizing my weaknesses. Please ask me a series of structured questions, one at a time, so I can reflect and respond deeply before moving to the next one."

This made ChatGPT an interactive thought partner, helping me uncover patterns in my work, habits, and decision-making style in a structured way.

The Breakthrough Insights: Strengths, Blind Spots, and Energy Drains

Through this exercise, I discovered some critical truths about how I work best.

My Biggest Strengths

✅ Rapid, High-Impact Problem Solving – I quickly diagnose a company’s growth bottlenecks and provide actionable solutions.
✅ Deep Strategic Thinking & Pattern Recognition – I recognize high-leverage opportunities faster than most.
✅ Execution-Backed Expertise – Unlike many growth advisors, I don’t just teach growth—I continue to do it hands-on in interim VP growth roles.
✅ Strong Reputation & Network – My book Hacking Growth has sold 800,000+ copies worldwide, and I've helped drive early success at several well-known companies.
✅ Equity-Focused Thinking – I prefer engagements with long-term financial upside (equity) rather than just fees.
✅ Thrives in Fast-Paced, High-Intensity Conversations – I love quick, high-value problem-solving sessions rather than long, slow engagements.
✅ Strong Execution Under Pressure (But Needs Deadlines) – Without a deadline, I can get stuck in analysis paralysis, but under pressure, I execute quickly.

My Biggest Weaknesses & Constraints

⚠️ Struggles Nurturing Long-Term Client Relationships – I don’t retain past conversations well and prefer shorter-term, high-impact engagements rather than ongoing relationships.
⚠️ Too Much Human Interaction is Draining – Excessive meetings, travel, and group discussions mentally drain me.
⚠️ Prefers Independence Over Delegation – I find it hard to delegate because it feels faster to do things myself than explain them to someone else.
⚠️ Prefers Execution Over Relationship-Building – I am not naturally wired to nurture long-term relationships, which makes repeat business harder to maintain.
⚠️ Can Get Stuck in Overthinking Without Deadlines – Without constraints, I can analyze a situation indefinitely instead of acting.
⚠️ Too Much Travel is Unsustainable – I traveled 200,000 KM last year, but I don’t want to feel like I have to travel excessively to hit financial targets.

Putting It into Action: How I Designed My Ideal Work Structure

I asked ChatGPT about a series of roles I may want to consider in the future, including:

✔️ Interim VP Growth Roles – I focus on early-stage scaling after product-market fit is validated. While I could earn higher fees working with larger companies, this stage is where my strengths are best leveraged—and it’s the most fun for me.
✔️ Venture Capitalist – I’d be strong at identifying winners and scaling post-PMF startups, but I wouldn’t enjoy the long relationship management and LP fundraising.
✔️ Founder Again – I’d be great if I came in post-PMF with a strong COO, but I wouldn’t enjoy the long-haul grind of another 7-10 year founder journey.
✔️ Scaling a Growth Advisory Firm – I could build a more structured, scalable model for my expertise, but I’d need to build and manage a team.

I also used ChatGPT to create a personalized guide for my personal assistant, outlining my strengths, challenges, and how she can best support me.

Final Thoughts: The Power of Self-Discovery

This process didn’t just give me clarity on my strengths and weaknesses—it confirmed that I’m already aligned with what I do best.

Your biggest career breakthrough might not come from a new job or strategy—but from truly understanding yourself.