Get Rid of Your Greatest Strength’s Weakness

Your greatest strengths are also sources of weakness, but who says you can't dull the harmful sides of these double-edged swords?


Michael Jordan’s greatest strength is his competitiveness. While it earned him basketball championships and billions in endorsements, it made him fail as an NBA team owner and doesn’t seem to have led to a winning personal life.

Vincent Van Gogh’s greatest strength was his emotional intensity. While it gave him a unique perspective on the world, it also led to isolation and mental illness.

My wife Kim’s greatest strength is her impeccable taste. While it helps her design beautiful things, create delicious food, and choose perfect husbands, it makes her hyper-sensitive to flaws and leads to unproductive perfectionism.

And you?

What’s your greatest strength? In what ways is it your weakness, too?

Most importantly:

What are you going to do about it?

Here’s my plan. I hope it inspires you to reduce your greatest strength’s weakness, too.

Walking through the jungle on my own.
“Yeah, yeah, but I think this way might be better.”

I’m Extremely Independent-Minded…

One of my greatest strengths and weaknesses is my extreme independence.

While most people gladly hitch smooth rides on the coattails of existing knowledge and experience, I think, “Lemme figure things out for myself,” and bushwhack my own path. It’s unnecessarily inefficient, arduous, and painful, but it’s also an adventure.

Sometimes I break through.

“Aha!” I high-five myself, “I’ve stumbled onto something fantastic.” I feel like an explorer who has discovered ancient ruins deep in the jungle.

Except it’s the year 2023.

So when I look around, I accidentally kick an empty Coke can and realize millions of others have been there already. I “discovered” Machu Picchu.

Chris talking with a llama at Machu Picchu
“What? You mean I’m not the first one to discover this?!”

The rest of the world came upon this epiphany the easy way: riding the idea gondola built by some famous philosopher, scientist, or TikToker. And they’ve ventured much further since.

So do I learn my lesson and follow their paths? No. I plunge back into the jungle.

…So Nobody Cares What I Think

Sometimes I actually do stumble upon an exciting new way of looking at things.

I holler out, “Hey! Come check this out! It’s pretty cool.”

But since I’m way off the beaten path, hardly anyone hears me. And since I’m such a weirdo, hardly anyone trusts me.

All anyone sees from afar is a scratched-up, dirty, sweaty loner waving and smiling like a lunatic.

Me all alone at the top.
“Amazing view! Too bad more people don’t care to come see.”

Luckily, thanks to my extreme independence, I don’t care what everyone thinks about me.

But I do care about their disregard. That means I’m failing at my mission to inspire them to adventure down ever more fulfilling paths in their own lives.

I’d be more successful as a tour guide, showing people paths to fulfillment discovered by others. But I’d hate that job. I’m too independent-minded to rehash others’ stories.

Or too selfish?

That’s another way of putting it. I do care more about myself than I care about you. And I rarely earn karma points for acts of generosity. In my defense, I avoid costing myself karma points by harming others to my benefit. And I’m trying to help others with The Zag.

We’re all fundamentally selfish, anyway. The trick is being selfish in a helpful way.

From Double-Edged Sword to Machete

What can I do to wield my extreme independence without harming myself with it?

Answer: Be less of a loner:

  • Find people I admire who can show me the ropes (aka mentors).
  • Connect with peers whose missions are tangentially related to mine.


I’ve known this for a while. My dream “perpetually perfect” life includes a strong network of fellow explorers to collaborate with and challenge one another. Not only could we help each other cover more ground, but we’d have more fun at it, too.

In my naive optimism (another double-edged sword in my armory), I believed that if I did enough interesting work, I would attract the attention of fellow explorers. Then they’d send me emails, Calendly links, podcast invites, and whatnot.

But I’m still waiting.

Maybe they can’t find my email address? It’s

Sadly, one of my favorite quotes from Mark Manson, “If we know our weaknesses then they stop being weaknesses” isn’t true. Our weaknesses (and strengths!) only stop being weaknesses if we treat them.

So I need to stop waiting for co-explorers to find me and go reach out to them.

“If we know our weaknesses then they stop being weaknesses.”

– Mark Manson (But I no longer agree.)
Me with group of fellow explorers.
At least we’re lost together.

You’re Welcome, Future Me

I don’t want to do it.

Reaching out to others is time-consuming, I suck at it, and when I’ve tried in the past, I’ve suffered minor frostbite from all the cold shoulders. I’d much rather keep writing, researching, and arguing with ChatGPT on my own.

But I want to have done it.

Even if I fail to find a team of co-explorers, my future self will be glad I tried. Better that than continue along my current, unproductive path hoping for different results.

So, for my July “Pump,” I challenged myself to a “Networkout.” Every Tuesday and Thursday from 2 to 5 pm, I push myself to get on the radar of my peers and potential mentors. I’m emailing them my thanks, commenting on their content, and offering helpful (I think…) feedback. If I can, I’ll get them on the phone.

And I’m trying to do this systematically, so even if all my virtual high-fives are left hanging, at least I learn from my mistakes and do better the next time.

Connecting with peers is like any skill: the better I get at it, the higher my success rate and the lower my perceived effort. This tilts the cost-benefit scale in favor of outreach. Eventually, I won’t need a strict “Networkout” schedule to force myself to do it. I’ll want to as much as I want to write, research, and otherwise explore on my own.

Then my adventures will be even more extraordinary and more people will take notice, but I’ll preserve my extreme independence.

And then I’ll be able to focus on making another strength of mine less of a weakness.

Maybe my optimism?

We’ll see.

Improve your greatest strengths and reduce their weakness cover image.
Turn your double-edged sword into a wicked single-edged one.

My Challenge to You

Ask yourself:

What do you think is your greatest strength? How is it hurting you? And what can you challenge yourself to do to minimize the damage while sharpening the positives?

Then make your plan and get to work.

If you want some company, guidance, and structure, consider this:

Join me in The Pump!

The Pump is a personal development workout club where each member picks an area of their life they’d like to strengthen, makes a plan, then gets to work. Then we share our progress in weekly check-ins.

I launched The Pump on July 1 for a month-long trial alongside a handful of brave readers. It’s been rewarding enough that I want to keep it going indefinitely. I have no shortage of strengths and weaknesses to work on, after all.

If you’re interested in joining me and others in The Pump, find more info here:

Free Wake-Up Call

Take the 20-question "Comfort Zone Assessment" to find out in just 3.5 minutes:

Where are you complacent?

Which area of your life most needs a push?

How to get started?

It's gimmicky and unscientific, but also quick, fun, and revealing.

Be Uncomplacent

PS: Surprise personalized accountability challenge afterward.

About the author

I'm Chris. Canadian, husband, dad, writer, investor, athlete, and obsessed explorer of the secrets to living a never-boring, always improving, unfollowable life story.

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