Roy's Blog
October 5, 2026
SCARS. BEAT. PROMPTS.

🚀 Audacious Move™ of the Week
SCARS. BEAT. PROMPTS.
AI can give you career advice in seconds.
But the mentor who can change your career brings something no prompt can manufacture: lived experience.
We are drowning in advice.
Watch a video.
Follow a guru.
Download somebody’s 10-point formula for success.
You can get an answer to almost anything before you’ve finished your morning coffee.
But answers aren’t the scarce commodity anymore. Judgment is.
And judgment is earned.
It comes from making decisions when the data was incomplete.
Screwing things up.
Getting blindsided.
Dealing with impossible people.
Making a call when there was no obvious right call.
And living with what happened next.
That’s why, when you’re choosing a mentor, I wouldn’t start with credentials.
I’d look for the scars.
Here’s what to look for.
🚀 #1. They’ve Got Stuff Done
Forget impressive theories.
Look for a track record of achievement.
The best mentors have built things, changed things, fixed things and delivered results.
They’ve faced obstacles and found a way through them.
They haven’t just studied success.
They’ve produced it.
AI can synthesize thousands of theories about what successful people do.
Your mentor should be able to tell you what happened when the theory didn’t work.
That’s the experience you want sitting across the table from you.
🌪️ #2. They’re a Graduate in Messiness
Business isn’t neat.
Careers aren’t linear.
And no algorithm gets to make all your difficult decisions for you.
Organizations are full of politics, uncertainty, competitive pressure and human beings who don’t always behave rationally.
Find someone who has succeeded in that messiness.
Someone who has walked into a situation where the playbook didn’t fit and figured out what to do next.
You want practical wisdom earned in the real world—not textbook perfection.
🔥 #3. They’re an Operator First
Find a doer.
Someone with what I call a Masters in Business Achievement.
They execute.
They make decisions.
They produce results.
They understand something increasingly important in an AI world:
Knowing more isn’t the advantage it once was. Doing something useful with what you know is.
Execution Is Your Strategic Learning System.
You execute.
You learn.
You adjust.
Sound familiar?
Be Imperfect FAST™.
👟 #4. They’ve Been Close to the Front Line
Don’t assume the best mentor occupies the biggest office.
Some of the most valuable teachers are people close to customers and operations.
They know where strategies collide with reality.
Where the beautiful PowerPoint hits an angry customer.
Where the clever idea smashes into a process that doesn’t work.
Where somebody actually has to deliver what leadership promised.
That’s where judgment gets built.
Find someone who has been there.
🏪 #5. They Understand Small Business
Never underestimate a successful small business leader.
They don’t have massive staffs, deep pockets or endless resources to hide behind.
They improvise.
They solve problems.
They make decisions with imperfect information.
And they live with the consequences.
They survive because they execute every day.
That experience is mentoring gold.
💥 #6. They’ve Failed
This one matters more than ever.
Be suspicious of anyone whose career story sounds perfect.
Failure teaches things success never will.
The mentor you want has made mistakes.
Backed the wrong idea.
Trusted the wrong person.
Missed something they should have seen.
Taken a hit.
Learned.
And come back smarter.
Success gives you credentials. Failure gives you wisdom.
You need both.
⚡ #7. They Live in a Culture of Execution
Finally, look at the environment your potential mentor comes from.
Do people spend their time discussing things?
Because we’re moving into a world where creating another idea, another analysis or another recommendation is becoming ridiculously easy.
Execution remains bloody hard.
Ideas have zero value until somebody turns them into a result.
Find a mentor who understands that.
🎯 Advice Is Cheap. Judgment Isn’t.
That’s the shift.
Your mentor doesn’t need to be famous.
They don’t need thousands of followers.
They don’t need to dominate LinkedIn.
And they certainly don’t need to be a self-proclaimed guru.
They need scars.
They need evidence.
They need stories that didn’t end the way they expected.
They need a history of getting stuff done when circumstances were ugly and the answer wasn’t obvious.
Use AI.
Use every tool available to you.
But when you’re looking for someone to help shape the decisions that could change your career, look for something technology can’t download for you.
Lived experience.
Choose someone who has lived the lessons you need to learn.
SCARS. BEAT. PROMPTS.
🚀 Want more Audacious Moves™?
🎙️ Listen to Audacious Moves to a BILLION™ for practical, contrarian ideas for building an extraordinary business.
✍🏻 Explore more articles, ideas and proven tools at BE DiFFERENT or be dead.
Extraordinary businesses aren’t built by ordinary decisions.
They’re built one Audacious Move™ at a time.
Now go make yours.
Cheers,
Roy

- Posted 10.5.26 at 06:00 am by Roy Osing
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