The 3 Biggest Mistakes 20-Somethings Make When Looking For Mentors

by Alexander Heyne · 2 comments

Mentorship mistakes

About five years ago, I sent an email to someone I had a loose relationship with, and was sure I’d score a home run:

“… I guess what I’m saying is, I really want you to be my mentor.”


Of course, I got no reply, and these days I can imagine the guy on the other end thinking, “ugh, another one of these” before hitting the delete button.

Like everyone, I made horrible mistakes at the start of my “career searching” days, where I wanted to have influential people’s advice on my path, but didn’t know how to really open a conversation.

Now, as more and more people gradually hit me up for advice, I can see from the other side of the table what’s going on a bit better.

My Rookie Mentorship Mistakes


Please don’t beat me to a pulp with that keyboard!

When I was in my early 20s, I didn’t realize that if you wanted to meet someone you could just reach out to them and ask to meet them.*

So in my early 20s, I didn’t realize that mentors – and even some influential people – are much easier to meet than you think (if you reach out the right way).

For example, when I was living in China I was thinking of Chinese medicine as a profession. There was a well known professor that my friend in China told me about, who was in Portland, Oregon and was affiliated with one of the major Chinese medicine schools there.

I thought to myself, wouldn’t it be aweosme if I just emailed him and could pick his brain about what it takes to attain mastery and be world class?

How cool would it be if this guy, who was really at the top of his game, would take the time to chat with me?

Wouldn’t it be awesome?

So I emailed him.

I followed up with him several times over a few months, and some months later I said something along the lines of:

“Hey, I know you were the dean of this program, and I have a quick question on what it takes to become great – do you have five minutes where I could buy you a coffee or tea?”

He actually replied to me saying he’d be happy to meet, gave me the address for his home, and we sat down for an hour to talk about Chinese medicine.

It blew my mind how generous he was with his time, that he was so accessible and would even invite me to his home.

It almost re-wrote this narrative in my mind that I have a hard time making friends, or that influential people are hard to reach, that they want to slap you in the face and just slam the door.

This guy was super open.

Now, in business it’s often different because everyone is interested in ego, fame, and riches, so a very successful person is more likely to reject you and be guarded since there are many people who want their time and advice.

However, in many other fields (outside business), where people are more interested in mastery and becoming incredible at what they do, mentors are often really happy to help newcomers with their passion and their experience.

It made me realize how many of these opportunities I must’ve passed up on, because I didn’t have the balls to go out and ask people.

*There’s a heavy P.S. here, see below.

Asking: Your Super Power


I have this horrible pimple I don’t want you to see today.

All you have to do sometimes is ask.

It made me realize that 99.9% of people never even ask.

I guarantee he would’ve let dozens of other people come to his house, because it’s what he loves, but most people never would have asked because people don’t know you can “do that.”

Here’s another cool story about asking.

Through the Milk the Pigeon email list, one person replied whose name was also Alex and he said, “hey man, I just moved to NYC and I’m interested in some of the similar things you are, would love to grab a coffee and meet. Here’s my own personal website.”

Usually I would say no, but he took the time to write a personal (not-selfish) email that added value and told me a bit about himself so I knew he wasn’t a complete weirdo.

We ended up connecting, and now (years later) he’s one of my closest friends, we’re in a mastermind together, and have shared hundreds of business emails together.

And it all started with him saying, “hey dude, want to grab a coffee?” beacuse he had the guts to.

But he also framed it in a way that added value to me.

It makes me wonder how many thousands of people would also want to reach out and just hangout but never asked (or asked in the wrong way).

Realistically, a lot of the time reaching out does work – and works incredibly well.

Get Mentors (And Friends) Like a Pro – Not a Selfish Bastard


Bro, I’m a pro – chill the fuck out, I got this.

Let me be clear here, most people just never ask.

You can’t get unless you ask, and if it’s over email, the worst case is that a person will just not respond – it’s very unlikely that you’d see someone react aggressively towards you.

How do you reach out the right way though?

Like I said, I get lots of emails which are basically requests for my time, but very few people emailing me who ask for something, but also have something to offer.

Here’s what I would’ve done back then.

1. Have the guts to ask.

Most of the time, this is good enough. If they don’t reply or say no, ask at least five times, spaced two weeks apart.

2. Frame it the right way.

Next, another thing most people do is just phrase the email like this:


… Without thinking of the other person.

How do you think you’d feel if you got 30 emails today – and they were all paragraphs long asking for advice?

It feels like shit, like you have to sit there for two hours as a chore responding to people – 99% of which won’t even take your advice and do anything with it.

The thing that I changed was always thinking of how I can add value to the other person, even if you don’t think there’s a way to add value.

3. Here’s a good example of a cold email.

Sub: Want to meet up?

Hey dude, I’ve been reading MTP for a couple months now and love what you say.

I have my own site right here which is pretty similiar too:

I just moved into NYC and I know you said you’re in there a lot, want to meetup for a quick coffee? 

There are also a few online courses that I bought that i’d be happy to give you my login details for.

- Your awesome name.

This is almost word for word what my friend Alex sent to me when he moved to NYC and didn’t know anyone.

Realistically, asking anyone to meet up in person (if they don’t know you at all) may not work, especially if you’re framing the email as, “let me pick your brain.”

But here’s the exact email I sent to that medicine mentor of mine.

Email 1

And here was his reply:

Email 2

First, remember that I had emailed him about 6-7 times over the course of a year, asking simple, one-line questions.

I don’t know whether or not he knew me or remembered me, but I always sent the email in the same thread to build a relationship.

By the time he replied with this, I was like holy shit, this is awesome!

A forty minute uber for $100?

Not a problem at all, I would’ve walked five hours to make this appointment.

Notice how I didn’t take my own advice to add value – sometimes you don’t have to, and asking passionate people to share their advice is often enough.

The “five minutes” time frame is really helpful too.

4. Ask for coffee or a remote skype session (for five minutes).

The other thing is that many people will be happy to meet with you, and if they aren’t, email them back asking if they’ll skype or have a few minutes for a phone call.

Now there’s no excuse if you live in goddamn Micronesia and your mentor works at Harvard – make the call.

Who Would You Reach Out to If You Got a Guaranteed 5-Minute Meeting?

Kind of a cool question, huh?

People interested in mastery (like a specific skill, not business) are often most interested to share (in my experience).

Here’s your mission for today:

Reach out to 1 person that’s an influential mentor of yours and try to get them on the phone for 5 minutes, because you might be surprised at the kinds of miracles that occur.

Comment below – who’s one person you would love to have a 5-minute conversation with to reach your goals?

How could you offer value to them – even if you don’t think there’s anything you could add?

Think about laterally adding value, if they know business, maybe you can offer to help with their relationship, spirituality, or health.


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{ 2 comments… read them below or add one }

Fix November 15, 2016 at 3:54 am

Right now you need to be really good at three to five things, find the common intersection, and then build a business around those talents. You can create your own personal brand and offer something truly unique that few people on this planet could do in the same way.


Gustavo Woltmann February 4, 2017 at 7:18 am

This topic is very important. Every young man has to look for right mentor so he needs to be very careful when he is doing it.


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