Reinvention Roadmap
Ten years ago, I was facing the possibility of losing $14 million. I went to my mentor looking for reassurance.
His advice? “Wish for bigger problems.”
I couldn’t believe what I was hearing.
My business was growing fast, and suddenly everything felt at risk. I was devastated. I wanted someone to tell me it would be okay.
Instead, he reminded me that I’d always wanted to build a billion-dollar company. If I couldn’t handle a $14 million problem, how was I going to handle the problems that came with a billion-dollar business?
Frankly, I was a little pissed off. But his question stayed with me.
I’d been so consumed by the size of the problem that I hadn’t considered what it was asking of me. I needed better strategies, sharper judgment, and a different mindset. Once I started looking at it that way, I got creative, found a way through, and ultimately built a much bigger business.
Looking back, my mentor had shown me something I couldn’t see for myself: the gap between the leader I was and the leader my ambition required me to become.
But I’ve since learned that the most consequential gaps aren’t always exposed by a crisis.
Sometimes, they’re hidden in the very things we’re good at. Habits and instincts that have served us for years become so automatic that we stop questioning them, even when our circumstances change.
And unlike a $14 million problem, these limitations don’t announce themselves. Often, someone else has to help us see them.
I discovered one of mine when I asked my team: “What’s one thing I could do differently to make our meetings more effective?”
Their answer caught me off guard.
“Don’t speak first.”
I loved brainstorming. I’d jump in with ideas to get the energy going, assuming everyone else would dive in too. I thought I was encouraging participation.
But as CEO, my words carried more weight than I realized. Once I shared an idea, people started reacting to my thinking instead of exploring their own.
I was trying to open up the conversation. Without realizing it, I was narrowing it.
That was hard to hear because my intentions had been good. But intentions don’t always tell us the truth about our impact.
So I changed one habit. Now I let everyone else go first. I listen, ask questions, and contribute at the end if I have something worth adding.
What had once been a strength had become a limitation.
That experience changed how I think about feedback. Sometimes the most valuable truth isn’t about something you’re doing wrong. It’s about something you’ve been doing right for so long that you haven’t noticed it no longer serves you.
And the more authority you gain, the harder that truth can be to hear. People increasingly defer to your judgment, which means you have to become more intentional about inviting perspectives that challenge it.
My mentor showed me that I needed to develop new capabilities. My team showed me that I needed to rethink an existing strength. Both changed what became possible for me.
And perhaps that’s the most exciting part of reinvention. No matter how much you’ve accomplished, you’re not limited to the person who got you here. You can develop new capabilities, change old habits, and become someone capable of things you haven’t yet imagined.
So wish for bigger problems. Seek out people who challenge you. Stay open to the truths that make you uncomfortable.
Because the greatest opportunity ahead of you may not be what you achieve next, but who you become capable of being.
Growth isn’t always about handling more complex versions of familiar challenges. Your next chapter may demand entirely new ways of thinking, deciding, and leading.
The qualities that made you successful can become limitations when circumstances change. The question is whether they still serve what you’re trying to achieve.
The best truth-tellers don’t just help you solve problems. They challenge the assumptions and habits that may be preventing you from seeing what’s possible.
Identify what people consistently praise you for. Then ask: Where might this strength now be limiting my effectiveness or the growth of others?
Consider your next big ambition. What will it require you to become good at that your previous success never demanded? Choose one capability to start developing.
Find someone who has navigated the transition you’re facing. Ask: “What did you have to stop doing, even though it made you successful, to reach your next level?” Their experience may reveal a blind spot you haven’t yet recognized.
Use this AI prompt to challenge your assumptions, uncover hidden limitations, and identify the capabilities your next chapter may require. Think of it as a mirror that helps you see what experience and success might have made harder to recognize.
COPY THIS PROMPT
Act as a candid, insightful advisor helping me identify where my past success may be limiting my future growth.
My current role or situation: [Describe]
What I’m trying to achieve next: [Describe]
The strengths, habits, and approaches that have made me successful: [List 3 to 5]
Challenge my thinking by exploring:
1. Hidden limitations: Which of my strengths could become liabilities at this next level, and under what circumstances?
2. Outdated assumptions: What might I still believe because it worked in the past?
3. Capability gaps: What new skills, behaviors, or ways of thinking might my next chapter require?
4. Uncomfortable truths: What might someone who knows me well hesitate to tell me?
Don’t flatter me or manufacture criticism. Distinguish reasonable hypotheses from established facts. Ask clarifying questions where context is missing.
End with three specific questions I should ask people who know my work to test your observations.
The real test: Take those three questions to people whose judgment you trust. AI can help you identify possibilities, but honest human feedback will help you determine which ones are real.
Think Again by Adam Grant
Adam Grant argues that in a fast-changing world, the ability to rethink and unlearn may matter more than raw intelligence. He makes the case for building a “challenge network” of people willing to question your assumptions. It’s a useful reminder that expertise is most valuable when paired with the humility to keep learning.
Dare to Disagree by Margaret Heffernan
Most of us instinctively avoid conflict. Heffernan argues that constructive disagreement helps us think better, make stronger decisions, and achieve progress. What stayed with me is her point that good disagreement takes skill and practice; it doesn’t happen by accident, and most organizations never create the conditions for it.
Who has told you a hard truth that changed how you lead?
Until next time...stay curious!
Cheers,
Nikki
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