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5 Reasons Millennials Struggle to Find Mentors

When you’re in your 20s and 30s, sometimes all you want is someone older to help guide your way. Here are five reasons millennials struggle to find mentors.

Millennials Struggle to find mentors
Source: Warner Bros., and an amazing film on this topic

One of the biggest issues I get raised to me by people in my age group is the question of finding the right mentors for this season of life. The ages between 20 and 40 are drastically diverse, and seeking direction from your peer group who are struggling with divergent issues to your own can be difficult. Sure, at the start of our 20s, all of us are in a similar boat – getting set into full-time work, completing university or college courses, stepping out after a few years in our apprenticeships, starting relationships at the same time. But once you go over the age of 25, all of a sudden finding people who are similar to you is a major struggle. Some already have kids, some have never dated anyone, some have been married, some have been divorced, some have started thriving businesses, some have already filed for bankruptcy, some consider themselves professionals and are well established in the path of their choosing, some have no idea where the path even begins.

And so, whereas in early days where we would have been able to move together like a group of pack animals (in that we had a course, a direction, a mandate, or a cause that united us and kept us at least in relative proximity to one another), as the years go by, it’s like there’s no one around us we can look to to make sense of our current season of life.

That’s when we realise the benefits of having mentors. If we can’t find people who are on the same page as us, we need to find people who have successfully navigated a similar path before.

But for many of us, finding such people is a major challenge.

Why is that? Here are 5 reasons I think millennials struggle to find mentors.

#1: We don’t know what to look for and get burnt

One of the primary drivers for people finding a mentor is because they’ve been burnt by other people before, whether friends, family, relatives, or their support network. And so, because of past difficulties, we set out trying to find people who are older or further along than us, only to encounter the same disappointment again. We thought that by finding such a person, such a couple, such people, we wouldn’t get hurt.

And if you get hurt by someone you thought you could look for guidance from, it burns even more.

I think the hardest thing about people is to identify if someone is truly worth following or not. Does a couple being married for 20 years mean that they’ll give advice on having a happy marriage? Does a businessperson with 30 years in the industry really have insights that will help, or destroy? Does someone who says they’re willing to mentor you but then constantly bail on you actually have what it takes to help you? Does someone being in the same age group as you, or being younger than you, disqualify them as a mentor candidate simply because of the number next to their name?

I would always say that in any relationship with people, we should be realistic about the fruit of the person’s life. For instance, don’t just look at the duration of their marriage – is their marriage actually a blessing to others, and to each other? Does this person truly lead their company well, or are they just trying to compensate for something? Does this person prove that their worth your trust?

Two great thoughts I heard from Microsoft leadership consultant, John Maxwell, on these issues: First is that “he who considers himself a leader but has no one following him is simply taking a walk”. If no one thinks this person or these people are worth following, it’s probably a red flag. Furthermore he said that the advice he got on the subject of mentors was that many of them are probably going to be found in books and media resources. The sorts of people you want to guide you may not currently be in your immediate circle, and it’s actually quite rewarding to follow someone from a distance, especially if they’re worth following.

Or maybe the people you need are already in your circles?

#2: We think our experience is so different to everyone else

People tend to be obsessed with their own pain and their own negative experiences. When we’ve been through times of loss or of confused direction, we tend to think, well, no one else has experienced what I’ve experienced, it’s just me, no one else knows what I’m going through.

It’s quite an isolating line of thinking.

And so like the Hebrew prophet Elijah who cried out because “he was the only one”, we cut ourselves off from the reality of the people who have gone before us.

The truth is that as bad or as difficult or as unsure a time we could have gone through, there’s someone else who has gone through the exact same thing. One of my favourite things to do is help to show people how much they have in common with the people who are already in their lives. We just so quickly assume that those smiling faces mean that they wouldn’t understand what you’ve gone through. In truth, it’s often us who are usually unwilling to understand what those people have gone through, and not been able to see how well they’ve come out the other side.

You’re not the only one. This is a foundational thought in finding a mentor.

#3: We don’t think it’s fair that we have to go looking

When I was 8 years old, it was someone else’s responsibility to make sure I could eat. If I went the whole day without food (which never happened by the way, just as an example), you wouldn’t blame my 8 year old self, you would blame the people responsible for me. Fast forward 20 years, I’ve owned my own home for a few years now, and have my own means of income. If I was sitting on the couch now and not eating, it wouldn’t be fair for me to think to myself, “Well, this is really unfair. Doesn’t anyone care about how hungry I am? Doesn’t anyone care about what I need?”. No, you wouldn’t. Because I’m a grown man. If I need something now, I have the means to go get it.

I think this example parallels the approach many take to finding mentors and people to connect with. Why hasn’t anyone looked after my needs? Why doesn’t anyone care about me?

Because it’s not really about the fact that people have to care for you, because many people do. It’s about the fact that if you have a need, part of being an adult is going after it.

And that’s actually quite fair.

#4: We get entitled and say we want something we won’t make enough effort for

I gotta tell you, this is my pet hate with my generation. I’m so tired of hearing people say they want something, but then say “they’re so busy”. Or “it’s just hard for me to get there”. Or “it’s my personality”.

Saying you want something isn’t enough – you have to make the effort for it.

One thing I see time and time again is people asking to catch up with a mentor figure – usually someone who is quite busy and living an active family and career life – and they treat the person’s time with utter contempt. They show up late, they cancel with short (or no) notice, and they expect the mentor figure to do all the work.

One of the best ways I’ve been able to adopt mentors in my own life is offering to take the person or the couple out for dinner, at my expense, and having a bunch of questions ready to go. Arrive early, finish on time, and honour the person who’s accepted your invite. The more honour you place on people worthy of honour, the more you’ll find the truest benefit from such people.

Moreover, learn how to talk to someone in such a position. You expect them to just talk to you on your level. Meet them on theirs. If they have kids and you don’t, learn how to speak to parents. Learn how to speak to someone from an older generation. Learn how to speak to the opposite sex. Learn to listen and give credence to an opinion you think you fully understand. You’d be surprised how far that’ll help you go.

#5: We can’t handle correction well

I have a number of key mentor figures in my life, and recently I’ve found myself learning from another man I met a few months ago. I remember one night he caught up with me for dinner and highlighted to me a bunch of issues he’d noticed from a few encounters with me. After adopting the feedback, he told me I was an exception in that I had actioned his feedback immediately. His experience with many millennials is that they get and stay defensive, and don’t accept or invite correction.

Let’s be real – no one likes being told when they’re doing something wrong, or if there’s something they could be doing better. And many of us actually carry a great deal of pride that prevents people feeling comfortable enough to speak correction into our lives, and also prevents us from properly receiving feedback that could change our lives.

If you’re a closed door, don’t be disappointed that no one wants to bash through the wood and tear off the frame in order to try to get you to hear them. People eventually get tired, and if you’re always playing hard to get, eventually no one is going to get you.

Eat the humble pie. Lay down the pride. Invite feedback and correction, and get ready for what that’ll mean when someone actually takes you up on your invite.

Otherwise, you don’t want a mentor, you just want a validator.


Anyway, these are just some of my observations and experiences with regards to millennials and mentors. My desire is that all people would find people they can look up to and help them navigate through life, as long we’re willing to get out of our own way.

How about you? Struggle with mentors? Or found some things that work?

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