Why Mentors Fail (and what to do about it)

Steve Glaveski
Dec 16, 2019 · 3 min read
Plato and his pupil, Aristotle

It is said that the right mentor can help you get further, faster.

As Isaac Newton said, “if I have seen further, it is by standing on the shoulders of giants”.

The right mentor can help us to see the forest from the trees, make better decisions and avoid treacherous pitfalls.


Mentor Challenges

But there are two key challenges when it comes to the mentor-protege relationship serving, rather than sabotaging an entrepreneur.

  1. Finding the right mentor(s)
  2. Determining which advice applies to your unique circumstances

This post will focus on the latter.

When we achieve success in any domain, it’s easy to fall victim to the ‘narrative fallacy’ and draw a straight line from start to end. But success is far from linear.

It’s easy to, as Behance founder Scott Belsky argues, misattribute our success only to the moments we’d rather remember as opposed to the things we’d rather forget.

We place little emphasis on all of the inevitable missteps and failures that essentially helped us to course correct or created serendipitous opportunities and connections that otherwise would have remained undiscovered.

Not only are mentors susceptible to the narrative fallacy, but the conditions that underpinned their success — market appetite for their product, competition, the economic and political landscape, the role of technology and so on — were unique to their business, not yours.

Source: Farnam Street

Finally, they are susceptible to bias, based on what worked for them. Steve Jobs might have pushed proteges to spare no expense on design and aesthetics, whereas Jeff Bezos might push for frugality so that you can carve out margins with lower-priced items because in both of these cases, that’s what has worked for them.

This is why we must not take anything a mentor says as gospel, and only apply or experiment with insights that have been stress tested against your unique circumstances.

Questions to Ask

  1. What mistakes did you make that helped you get on to the right track and inadvertently got you closer to your goal?

2. Which entrepreneurs do you admire, and why? (look for bias towards particular types of entrepreneurs)

3. When it comes to your product philosophy, what are your key values? (do these align with your product philosophy?)

  1. Which factors or conditions underpinned their success, and which of these does or can your business share?

2. Which factors or conditions, and which of these does your business share not and can’t share?

Based on the answers to these questions, you will develop a better understanding of how much of what your mentor says you should seriously consider for application to your own business, and how much you should discard.


Steve Glaveski is the co-founder of Collective Campus, author of Employee to Entrepreneur and host of the Future Squared podcast. He’s a chronic autodidact, and he’s into everything from 80s metal and high-intensity workouts to attempting to surf and do standup comedy.

Steve Glaveski

Entrepreneur. Author. Podcast host. Metalhead. Wannabe Surfer.

Steve Glaveski

Written by

#Founder of @CollCampus and @LemonadeStandCC. @Future_Squared #Podcast host. #Author of #TimeRich and Employee to #Entrepreneur. Visit: steveglaveski.com #MEL

Steve Glaveski

Entrepreneur. Author. Podcast host. Metalhead. Wannabe Surfer.

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