Why Not Ask? Your Heroes Might Say Yes…
The Power of Reaching Out for Mentorship
Have you ever looked up to an industry leader and thought, "I wish I could learn directly from them"—only to immediately dismiss the idea because they seem too successful, too busy, or too unreachable?
Here’s a mindset shift: Why not ask?
Many of the most successful people in the world were once in your shoes, looking up to their own heroes. The difference? They took the chance and reached out. Whether it’s an author you admire, a renowned CEO, a sought-after speaker, or a top-tier coach, asking for mentorship—even in a small way—can open doors you never imagined.
My Life of “Radical Asks”
In grad school, I had a guest professor that was amazing. Nancy had deep wisdom, experience, age, poise — and she was a highly sought after speaker and author. I was so impressed with her and told a fellow student that I would love to shadow her and observe her in action.
My friend looked at me and matter-of-factly said: “Then why don’t you just ask her if you can shadow her?”
It never occurred to me to ask.
As I thought about that, my mind was flooded with thoughts of her saying no (rejection), me feeling embarrassed and exposed, and general disappointment.
But I was willing to gamble. So I asked. She said yes.
I flew up to northern California and shadowed her for a few days. It was so much fun and I learned a lot. Even now, almost two decades later, Nancy is still someone I reach out to for mentorship from time to time.
Working Directly with Your Heroes
To this day, I am so glad I asked Nancy about shadowing her because it started a whole lifestyle and practice of “radical asks.”
My asks continued to speakers, authors, thought-leaders, business owners, and more. It’s taken me across the globe, to the private homes of some of my heroes, to emcee major conferences, and to get tours of exclusive places that don’t actually provide tours.
Just ask.
Worst case? They don’t respond. You move on, no harm done.
Best case? They say yes, and you gain direct insights from someone you deeply admire. That one conversation, one shadowing opportunity, or one coffee chat could change the trajectory of your career.
Final Thought
You miss 100% of the opportunities you don’t take.
If you want to elevate your career, sometimes the boldest move is the simplest: Just ask. You never know who might say yes.
Who is one person you’d like to make an ask from? Respond back and let me know, and I’ll respond back to you personally.
Cheers to you making radical asks and getting to work directly with leaders you admire!
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