When Expertise Becomes Avoidance (and Advice Stops Helping You)
During one of the hardest seasons of my career, when my board was trying to remove me, I turned to my coach for guidance and he told me to “talk to a tree.”
I was infuriated. Why would I talk to a tree? I didn’t fly him out here so I could talk to a tree. I wanted to talk to him.
But he told me again, “you’re going to talk to a tree.”
For a while I just stood there, convinced I looked ridiculous. I was pissed. I told the tree this was dumb. I complained. But then I kept talking. I talked about what was going on, what I was afraid of, all of it.
The tree didn’t say anything.
That really obvious reality—that the tree wasn’t going to talk back—became profound as I continued talking. The tree didn’t give me any advice or analysis. In that silence, I could hear my own words. For the first time in a long time, I felt safe enough to listen to my own clarity.
It struck me how quickly we lose access to ourselves when we’re frightened. We immediately turn outward, hoping someone will tell us the “right” move.
This is often the very opposite of what we need.
External support is crucial, but too much outside information floods you. Instead of creating clarity it leaves you confused and overwhelmed.
There is a key difference between seeking support and trying to outsource your leadership. One bolsters wisdom you already have, the other dismisses it entirely.
Knowing the difference is crucial. You can spend years drowning in expert guidance, but until you train your ear to hear your own voice, every decision will feel like you’re trying to outrun disaster. You’ll spend your time managing your fear rather than leading.
Trust and Doubt
Running a company amplifies all our old habits of doubt. When the pressure rises, reaching for external expertise feels like the smartest thing to do, the best thing for our company.
Coaches, colleagues, friends, books, podcasts, articles—they all offer valuable perspective. But when you use external authorities to soothe your anxiety you end up feeding your self doubt. For a second, it shields you from uncertainty, but each time you abandon from your own instincts you teach yourself you can’t be trusted.
And when you don’t trust yourself, you end up hoarding knowledge without building wisdom. You might accumulate a library of knowledge, but it’ll just sit there.
Expertise is only useful if you’re willing to back yourself.
The wonderful thing is that your instincts never disappear, they just grow quiet.
Returning to those instincts is about building trust. It requires repeatedly taking small risks on yourself, like working with a team. You can’t trust a team instantly, you build trust through progressive delegation.
Learning or Hiding
Right before every big decision, I always have the impulse to seek out expertise.
Are there books on this subject? Who can I call? I remember a podcast about this, where was that?
Sometimes I’m honestly gathering data, other times I’m trying to outsource my leadership.
These are three areas I check to know if external sources are actually helpful right now:
Focus
Is your research bringing you closer or farther to your problem/decision?
Closer looks like clarity: you have a deeper understanding of the issue. Your options come into focus. You can begin to articulate next steps.
Farther looks like chaos: you are tangled up in opinions, overthinking, excessive information. The issue seems to get bigger but never clearer.
Feeling
Do you feel curious or frantic?
Curiosity has space in it. The stakes are not life or death. You feel open, engaged, interested.
Frantic feels tight. The stakes are immense. You’re stuck in binary thinking (right vs wrong, success vs failure). You’re working from a place of scarcity.
Time
Can you put down the issue after you’ve thought or talked about it?
Once you take in new information are you able to take time to digest it? Or do immediatly you look for something new chew on?
When you return to the problem, are new insights emerging? Or is your mind running in the same circles?
If the deeper you dig, the less confident you feel, you’re not building expertise—you’re running from yourself.
You might be escaping the fear, but you’re also leaving behind your wisdom.
The Power of “Right and Wrong”
A common justification I make when I abandon my own gut is “you need the right information to make the right decision.”
But what is “right?”
Underneath our self-doubt is an old and stubborn belief that there is a right and wrong way to move forward.
Right and wrong gives us security. “Right” is a solid piece of ground in a shifting world. But if “right” promises objective success, “wrong” promises sure failure.
Suddenly every decision becomes high stakes, it’ll either shoot you toward success or doom you. This pressure forces you to abandon your own instincts in search of external validation.
I have a client who always wants me to tell him if he is right:
“What am I supposed to be doing?”
“What’s the right way to feel?”
“How do I know I’m doing it correctly.
He’s asking me if he’s safe, but my answers will never convince him.
These questions are part of a fruitless and frustrating quest. There are decisions that will get you closer and farther from your goals, but there are not objectively right and wrong choices.
You’ll will never reach “right”—but you can reach better places.
Re-thinking Right and Wrong
“Right” and “wrong” have been with us for a long time. You can’t just throw away. But you can re-think what they mean for your success.
Look back on three recent decisions and their consequences. Try to label them right/wrong.
If a choice wins praise but makes your work miserable, was it right or wrong?
If a choice doesn’t take you where you intended but shows you where you actually want to go, was it right or wrong?
This is how you fall in love with “
wrong.” Right and wrong can both be a routes toward your success. In that case, the real work is defining your goals, not evaluating your moves.
how do I want the business to grow?
how do I want myself to grow?
A guide is much more useful than a grade.
Putting It All Together
Leading is terrifying.
It means making choices from your wisdom and claiming them as yours.
But this is incredibly empowering. You get to take responsibility. You get to shape the direction, not follow someone else’s pre-made plan.
Self-trust doesn’t arrive in a moment of confidence, it accumulates through repetition. You practice listening to your instincts. You practice letting “wrong” teach you instead of punish you. You practice asking yourself what you want.
Next time you feel like you don’t know how to do something. Before you gather external information, ask yourself:
What do I already know?
What do I actually want?
What strategies and outcome feels most aligned with the business I’m trying to build?
Write the answers down before you read, ask, or research anything.
This anchors you in your own wisdom.
See you next week! 👑
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