020 – Failing from the Start

Greetings, Hero!

Today’s letter is a bit of a paradox—because while it’s piece of advice, it’s about the exact dangers of taking advice, or at the very least, seeking it out. And it’s doubly contradictory because advice is probably the number one reason people listen to mentors in the first place! But despite that, it seems I rarely end up giving people the actual advice that they wanted—and today, I want to explain why.

You see this play out most clearly in just how cryptic advice in stories can be: the hero comes around with a fairly straightforward question, and they take it to a wise old wizard or friend, and all they get is some kind of cryptic riddle or offhand comment. All they wanted was some straightforward, good-old-fashioned advice, and yet they cannot for the life of them find it. 

As a mentor, my responsibility is to help heroes accomplish their quests. And what many of them don’t understand is that the advice they’re seeking is sometimes actually counter or unhelpful to them actually fulfilling their quest. See, the nature of undertaking anything great in life is doing the kind of work that never gets any easier: facing the unknown. We have to dig deep within ourselves and find the courage to go and do something we’ve never done before in order to become the thing we aren’t quite yet. And that route is something every hero must do, on their own, for themselves. 

What many heroes don’t always see when they seek out advice is that they’re really just trying to escape the inevitable. They want advice about how to face something that feels unfaceable, about how to mitigate the exact fears that they need to face. And I know that I can’t help them, because the uncertainty of what to do often is the exact thing they need to overcome. 

There’s a quote from Nassim Taleb that paints the darker side of this as well—”When we want to do something while unconsciously certain to fail, we seek advice so we can blame someone else for the failure.” Sometimes, we seek out advice before we undertake the quest because opening ourselves to the chance of choosing the wrong thing is the exact risk we aren’t willing to take—when in reality, that choice is the actual call to adventure.

All of which to say… Advice is very useful, in fact, it’s often irreplaceable. But the next time you find yourself seeking advice, or giving advice, be careful—that advice might not be what you seek.

May the road rise up to meet you!

The Mentor

The Letter from the Mentor is a weekly letter of encouragement and inspiration from your favorite old wizard, archetypal figure The Mentor. Full of advice, stories, and cheerful good will, the Letter from the Mentor is a weekly reflection on the greatest heroes of our time and those times before. You can read more letters below or sign up to get them in your inbox every Tuesday morning here:

023—My Archrival.

Greetings, hero! I have to say, today’s letter is a little difficult to write. As the Mentor, I can’t tell you how many heroes I’ve

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