The botched pitch, the lost deal, the decision that cost a lot. In those moments, everything shifts. Shoulders drop. Eyes meet. You breathe a little easier, because suddenly the expert across from you is human again.
A young designer described this to me one day in a noisy café near the train station. Her mentor-a creative director at a large agency-had just told her how she was fired at 27 for saying yes to a toxic client. “That’s the day I realized,” the young woman told me, “that taking a risk doesn’t mean being reckless.”
She never made career decisions the same way again. And that’s no accident.
Why “I failed” is more powerful than “I succeeded”
When a mentor says, “Here’s how I crushed it,” mentees listen politely. When a mentor says, “Here’s where I crashed,” mentees lean in. The emotional temperature shifts. Suddenly the conversation isn’t about perfection-it’s about survival, repair, and choice.
Failure stories crack open space for curiosity. They give mentees permission to ask the questions they’re secretly holding back: How bad was it really? What did it feel like the next morning? What made you try again? Those questions live in the gap between ambition and fear. That’s exactly where calculated risk lives, too.
In those moments, authority doesn’t disappear. It becomes usable.
Take Jamal, a junior product manager at a fintech startup. His mentor, the VP of Product, was known as the “launch machine”-eight successful product releases in four years. Jamal assumed this guy never missed.
One evening after a long sprint, the VP pulled up an old slide deck. “This,” he said, “was my worst launch.” The metrics were brutal: only 3% adoption, a spike in churn, angry emails from sales. He walked Jamal through every bad assumption, the ignored warning signs, the pressure to deliver something before the quarter closed.
Then he showed the recovery plan: how they sunset the feature, owned the mistake with customers, and used the postmortem to redesign their risk process. Six months after that disaster, their next launch doubled revenue. Jamal later said that story did more for his confidence than any praise he’d ever received.
Psychologically, this makes sense. When mentors hide their failures, mentees assume risk is a test they’re expected to pass flawlessly. That breeds paralysis, not courage. By surfacing mistakes, mentors normalize the idea that risk comes with turbulence, not total catastrophe.
Failure stories also act like a map. They reveal decision points, red flags, and alternative paths. Mentees see that the real skill isn’t dodging every mistake; it’s knowing how to limit the downside and recover. That is the essence of a calculated risk.
And there’s something else at play: honesty builds trust faster than success ever does. A mentee who trusts their mentor’s humanity will follow them into bolder territory.
Turning painful stories into practical risk-taking fuel
The mentors who make the biggest impact rarely just “share a failure and move on.” They break the story into parts, like a slow-motion replay: Here’s what I knew. Here’s what I missed. Here’s the risk I thought I was taking. Here’s the risk I was actually taking.
One effective move is to literally sketch the decision tree-on a napkin, a whiteboard, a shared doc. Show the options you had, the one you chose, and the outcomes that followed. Then ask the mentee where they think the real risk sat. It turns a war story into a workshop.
Another powerful gesture: put numbers on the fear. How much money was at stake? How many clients? How many months of runway? Risk feels different once it’s dragged out of the fog and into concrete figures.
There’s a trap many mentors fall into: making their failure stories too neat, too polished-like a Hollywood arc where everything was secretly leading to the perfect lesson. Mentees can smell that from a mile away. They don’t need a TED Talk. They need the messy middle.
Let’s be honest: nobody really does this perfectly every day. Most people compress their pain into a three-line anecdote they can drop at conferences. A living, useful failure story keeps some rough edges. It includes the awkward email, the sleepless night, the colleague who disagreed-and turned out to be right.
The mentors who help mentees take real risks also avoid weaponizing their failures. They don’t say, “I did X and it went wrong, so never do X.” They say, “Here’s what I missed about the context. Here’s what I would check differently next time.” That nuance lets mentees build their own judgment rather than inheriting someone else’s fear.
“A good mentor doesn’t hand you a map out of their past. They help you draw your own, using their wrong turns as landmarks, not as warnings to stay home.”
Some mentors like to frame it with a simple checklist, almost like an emotional safety rail for mentees before they leap:
- What’s the worst realistic outcome-and can I live with it?
- What’s the best plausible outcome-and is it worth the cost?
- What signals would tell me to pull back sooner?
- Who do I need in my corner if this goes sideways?
- What will I learn even if this “fails” on paper?
Used together with real failure stories, this kind of list turns vague courage into grounded confidence. It’s the difference between “be bold” and “here’s how I’ve stayed bold without burning everything down.”
From borrowed scars to your own brave decisions
There’s a quiet magic in realizing that the people you admire most are carrying a private archive of bad bets, awkward phone calls, and emails they wish they’d never sent. Once you see that, you start to look at your own future mistakes differently-less like verdicts, more like tuition.
Mentees who hear honest failure stories tend to ask better questions before they move. They probe the downside with more clarity. They also start distinguishing between reckless gambles and thoughtful experiments. That shift alone can change a career, a business, a life.
For mentors, sharing failure isn’t about confession for its own sake. It’s a transfer of pattern recognition, a way of saying: I’ve walked through this storm; here’s where the ground was soft. For mentees, hearing it is an invitation-not to copy the path, but to walk their own with eyes a little wider open, heart a little steadier, and their hand closer to the “course-correct” lever.
| Key Point | Detail | What It Means for You |
|---|---|---|
| Failure builds trust | Mentors who share missteps appear more human and accessible. | Helps you feel less alone in your doubts and fears. |
| Stories teach risk mechanics | Broken-down failure stories reveal decision points and blind spots. | Gives you a concrete way to think through your own risky choices. |
| Calculated risk is learnable | Tools like decision trees and “worst-case” framing turn fear into action. | Lets you move forward with courage instead of waiting for certainty. |
FAQ
- How honest should a mentor be about their failures? Honest enough that the risk, the emotion, and the consequences are clear, but with sensitive details (names, confidential data) removed. The goal is learning, not oversharing.
- Can sharing failures undermine a mentor’s authority? When done thoughtfully, it usually does the opposite. It builds credibility, showing that their current judgment was forged through real-world tests, not theory.
- How can mentees ask mentors about failure without it feeling awkward? You can frame it around learning: “What’s a decision you’d make differently today, and what did it teach you about risk?” Most mentors welcome that kind of question.
- What if a mentor never talks about their mistakes? That’s a signal. You can gently invite it, but you can also look for complementary mentors or peers who are more open about the messy parts of growth.
- How do I turn a mentor’s failure story into concrete action? Write down the key decision points, the context, and the warning signs they missed. Then adapt those into your own checklist for the next risky move you’re considering.
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