Should I Tell My Mentor About My Failures or Just Successes?

Picture the night before a mentoring session. You're mentally sorting what to bring up, and you catch yourself doing something sneaky: you're building a highlight reel. The project that went well, the compliment your boss gave you, the small win you're proud of. And that thing that blew up in your face last week? You quietly file it under "no need to mention." You're not lying, exactly. You're just editing. But here's the trouble with editing out the failures — they were the whole point of having a mentor in the first place.

I get the instinct. I really do. When you respect someone, the last thing you want is for them to see you drop the ball. You want them to think their time on you is paying off. So you show them the trophies and stuff the fumbles in a drawer. I did this for years, and not just with mentors — with bosses, with peers, with anyone whose opinion I cared about. It took me a long time, and a few humbling seasons, to learn that the drawer full of fumbles was the most valuable thing I owned. This article is about why, and about how to actually open that drawer without dumping the whole mess on the table.

Why We Hide the Losses

Let's be honest about what's really going on when we edit ourselves. It usually isn't strategy — it's fear wearing a nice shirt. We're afraid the mentor will lose respect for us. We're afraid we'll look like we're not cut out for whatever we're chasing. We're afraid that admitting the mess out loud makes it more real. So we lead with the wins because wins feel safe, and safe feels smart.

There's also a quieter reason, and it's more flattering to us, which is exactly why it's dangerous. We tell ourselves we don't want to "waste the mentor's time" on our problems. We frame the highlight reel as a courtesy — "I don't want to burden them." But be careful with that story. Nine times out of ten, "I don't want to burden them" is just "I don't want to be seen" in a costume that lets us feel considerate about it. A mentor didn't sign up to watch you perform. They signed up to help you grow, and you can't grow the parts you keep hidden.

Here's the plain truth I wish someone had handed me at 25: nobody good is impressed by a person with no failures. They're suspicious of them. When I sit across from someone who only ever tells me about their wins, I don't think "wow, what a strong candidate." I think "this person is either not being straight with me, or not stretching far enough to fail at anything." Neither one is a good look. The highlight reel you think is protecting you is quietly telling on you.

Your Failures Are the Raw Material

Think about what a mentoring conversation is actually for. You're not there to be graded. You're there to get better. And getting better requires something to work on — a real, specific, slightly embarrassing thing that isn't working yet. That thing is your failure. It's not the interruption to the growth work. It is the growth work. Bring only successes and you've handed your mentor a puzzle that's already solved. What's left to do?

I started my first job at 17 and spent the next few decades working my way up from the floor through some big companies, and I can tell you that almost nothing I learned came from the projects that went smoothly. Smooth teaches you very little. You barely remember it. It's the day the line went down, the call I handled badly, the decision I made too fast — those are the moments burned into me, and those are the moments where somebody older and wiser could actually change my trajectory. But only if I told them. A failure I hide teaches me a small, lonely lesson. A failure I bring to a good mentor gets turned into a lesson three sizes bigger than the one I'd have found alone.

Here's the part that stings a little: the wins you're so eager to share are often the least useful things you can talk about. Not because wins don't matter, but because a win rarely needs a mentor's help — it already worked. A loss, on the other hand, is a door standing wide open. It's the one place where another person's experience can walk right in and rearrange the furniture. So when you trade a loss for a win in what you share, you're literally trading away the highest-value minutes of the whole conversation.

What a Good Mentor Does With a Failure

Maybe part of the fear is that you don't actually know what will happen when you say the hard thing out loud. So let me tell you what a good mentor does, because it's almost never what you're dreading. They don't recoil. They don't file it away as evidence against you. Most of them lean in, because you've just handed them the one thing that lets them be genuinely useful instead of politely encouraging.

A good mentor takes your failure and does three things with it. First, they normalize it — they tell you about the time they did something just as dumb or worse, which instantly shrinks the shame down to a workable size. Second, they help you find the actual lesson, which is usually not the obvious one. You think the lesson is "I'm bad at presentations." They help you see it's "you didn't prepare because you were avoiding the topic, and the avoidance is the real pattern." Third, they help you build the next rep — a concrete, small way to try again before the fear hardens into a story about who you are.

None of that can happen over a highlight reel. You can't get the "oh, me too" that dissolves shame if you never admit there's anything to be ashamed of. You can't find the deeper lesson if you only present the polished version. And you can't build the next rep if you've pretended there was nothing to rebuild. Every one of the most valuable things a mentor can do for you requires you to go first and show them the crack. Hide the crack and you get a nice chat and a wasted hour.

How to Share a Failure Without Oversharing

Now, before you swing all the way to the other side and turn every session into a confessional, let's be clear: "share your failures" is not "trauma-dump on a busy person." There's a craft to it. Transparency isn't about volume; it's about honesty aimed at growth. Here's how I've learned to bring a failure to the table in a way that actually helps.

Lead with the fact, not the flogging. Say what happened plainly — "I sent the report late and it cost us credibility with the client" — and skip the ten minutes of self-punishment. Your mentor doesn't need to watch you grovel. They need the clean facts so they can help. Beating yourself up in front of them isn't humility; it's just a slower way of making it about your feelings instead of your growth.

Bring the failure and a question, not just the failure. "Here's what went wrong, and here's what I can't figure out" turns a venting session into a working session. The question is the handle that lets your mentor pick the thing up. Even a rough one works: "Why do I keep doing this?" or "What would you have done at the fork?" You're not dumping a problem on them. You're inviting them into it.

Own your part, without owning things that aren't yours. Real transparency means saying "here's where I blew it" cleanly, and also not dragging in a hundred excuses. But it also means not swallowing blame for things outside your control. A good mentor can't help you if you're either hiding your role or exaggerating it. Aim for the honest middle: this is what I did, this is what I'd own, this is what I'm still confused about.

Why This Is Really the Law of Pain

One of John C. Maxwell's 15 Laws of Growth is the Law of Pain, and it says this: good management of bad experiences leads to great growth. Sit with the phrase "good management." Maxwell isn't saying pain grows you. Plenty of people get hurt and learn nothing — they just get bitter or gun-shy. Pain only becomes growth when it's managed well. And here's the thing almost nobody says out loud: managing a bad experience well is really hard to do alone. Left to ourselves, we either bury the failure or replay it on a loop. Neither one is management. Both are just suffering with extra steps.

That's exactly where a mentor comes in. When you bring a failure to someone further down the road, you're not confessing — you're managing. You're taking a raw, painful experience and running it through a wiser set of eyes so it comes out the other side as a lesson instead of a scar. Hide the failure and you keep the pain and lose the growth. Share it well and you convert it. Same bad experience, completely different result — and the only variable is whether you let someone help you process it.

I've lived both versions of this, and the contrast isn't subtle. Life has handed me some heavy things — I've been married three times and lost my first wife to cancer after 23 years together, and I've had plenty of ordinary career failures on top of the personal ones. The seasons where I white-knuckled the hard stuff in private are the seasons I grew the least; I just survived them. The seasons where I let people in — mentors, coaches, friends who'd been there — are the ones where the pain actually turned into something. That's the whole reason I ended up writing Leadership Between the Lines and teaching the LBL-10 workshop: the leadership that matters is forged in the failures you're brave enough to talk about, not the wins you're eager to show. A mentor can't spare you the pain. But they can help you manage it into growth — and they can only do that if you tell them it happened.

Reflection Questions

Sit with one or two of these before your next mentoring session:

1. What's the one failure from the last month I've quietly decided not to mention? Why that one?
2. When I edit myself with a mentor, am I protecting them from a burden — or protecting me from being seen?
3. Which of my recent wins actually needs my mentor's help, and which am I bringing up mostly to look good?
4. If I brought my hardest current struggle to someone wiser, what question would I want to ask them about it?
5. Am I managing my bad experiences, or just burying them and hoping they turn into growth on their own?

The Bottom Line

So should you tell your mentor about your failures or just your successes? Tell them the failures — carefully, but tell them. The wins mostly earn a nod; the losses are the open door where a mentor's experience can actually walk in and rearrange things. The stuff you're most tempted to hide is almost always the highest-value material in the whole relationship. Hiding it doesn't protect you. It just quietly wastes the very thing you came for.

Here's what I'd do before your next session: pick the one failure you've been rehearsing reasons to skip, and put it at the top of your list instead of the bottom. State it plainly, own your honest part, and bring one real question about it. Then watch what a good mentor does with it — because I'll bet money it's kinder and more useful than the story you've been telling yourself. That's not weakness. That's you taking a bad experience and refusing to waste it. That's how ordinary people grow, no cape required.

This ties back to The Law of Pain — one of John C. Maxwell's 15 Laws of Growth.