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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Advice Thumb


Listen, when I was a kid around fourteen years old, I still remember talking to one of my dad’s friends.

So we’re on the back porch and it’s a beautiful summer night.

He’s got a cigar in his mouth, and my dad has a cigar in his mouth.

I was asking him (my dad’s friend) advice for the future, because I explained that I was going to college in a couple years – so he unleashed a bit of his wisdom.

“Dude, I’ve gotta give you just one piece of advice – make sure you really enjoy those college years, because from then on out, it’s all work and all suffering, so make sure you really take the time to enjoy those years!”

And even though I was only fourteen at the time, I very clearly remember the emotion I first felt:

Fuck that! why the hell would I want four years of my (hopefully 95+ year life) to be done by the time I’m 22? Does that really make sense?

Whether you’re in your 20s or 30s, you’re going to get a lot of advice from a lot of different from people.

People have advice about everything.

And guess what?

A lot of the advice might be good, but a lot of it sucks too.

Here’s the thing: everyone has advice for everything, and the irony is that the less successful a person is in any domain in their life, the more likely they are to want to give you advice.

You’ll have fat friends giving you weight loss advice, to divorced people giving you marriage advice, to people who have struggled their entire lives giving financial advice, or miserable people giving happiness advice.

Unfortunately, the average person giving you advice is probably giving you – no surprise – average advice.

Because of this, there’s actually a very big danger in taking advice – and there are two things I personally use to vet advice to see if it’s really good for me.

Why You Shouldn’t Take 99% Of the World’s Advice

[click to continue…]


Path in woods

Most people blow the shit out of their 20s, because they make a very big mistake.

Most of the time when we’re lost in life, we do one of two things.

Think about the teenage years, when everyone is a little awkward, figuring life shit out, figuring parent-related shit out, and even figuring out sexuality.

Usually in those strange years, we tend to do one of two things.

The first thing is that if we’re lost, we just conform.

You know, our parents say, “Hey Jimmy, daddy was banker or a CPA, so you’re just going to go to school for accounting, finances or economics.”

And the kid’s either like, “Okay, fine, I don’t really care, I want a good job.”

Or, they tend to do the exact opposite.

Most kids just accept and conform, and work for mommy or daddy’s business, get the college degree, get married and get that whole white picket fence life – and just do what they see everyone else doing.

They don’t spend too much time thinking deliberately about what they want.

Most people just conform, which is fine.

Then, you’ve got another side of the coin here.

When we’re lost, we tend to either conform (and do what we see everyone else doing, going back to school, getting jobs, getting married, having kids), or we rebel against the system.

This is really easy to spot in the teenage years too.

You see kids going gothic for just a phase, from that 16-19 age, where they get piercings, black lipstip, fishnet shirts, and they’re involved in all kinds of alternative stuff.

Or you have those teenage girls that become lesbians for a few years, and magically become straight again by 21.

It’s just this fighting against the system, and fighting against the man idea (the whole preacher’s daughter syndrome).

Most of us conform, some rebel, but most people miss the magic: the third path.

The Third Path: Where The Magic Happens

The middle is where the magic happens.

Guess what? Neither of these paths are deliberate living. Neither of these paths get you to your dream life, because neiter of them are conscious, deliberate choices.

Most are just reacting to something (pulling or pushing) – accepting the push from your mom, or just pushing against it.

Neither one of those paths is me saying, “Hey, what do I really want from life, and where am I trying to go?”

The conforming path is just “okay, going with the flow…”

The rebeling path is just pushing shit away – just for the sake of rebeling, not because rebelling even gets you anywhere, it’s just about saying fuck you to mommy and daddy, or the man.

Neither of them are conscious choices about going down a deliberate path.

The secret is in the middle: what do YOU as an individual really want?

Most people are too busy going with the flow, like going back to grad school, or going off to thailand and becoming a digital nomad, stoner rhasta, saying “fuck you” to the man and promising to never get a job.

“I’m not dealing with this society bullshit” is a pretty common phase that almost every 20 something goes through at one point or another.

But both of these are losing paths, and neither of them really get you on the path that’s really fulfilling.

The Real Question About Figuring Out Which Path to go Down


My question for you is simple: first, what bucket are you in?

Maybe you’ve been conforming for the past five years – which is fine – maybe you just got a job and got married because you thought that’s what you were supposed to do.

Maybe you didn’t get a job, and just dropped out of society to live on the fringes, smoke weed, and just mess around because you didn’t want to deal with this society and grown up bullshit.

But what do YOU want?

What do you really want?

What do you want your financial life to look like?

What do you want your spiritual life to look like?

Your work?

Your health?

Your relationship?

Your travels?

What do you want all of this to look like, in the absence of conforming or just fighting against mommy and daddy.

Then, only then, can you go after the path you want.

Everything else is just a distraction, a bullshit side path.

Stop Lying To Yourself

Stop telling yourself things like you can be “successful or happy” – it’s bullshit.

Stop telling yourself you can be “spiritual or rich” – it’s bullshit.

Always choose the and.

You can be successful AND happy AND fulfilled AND contribute AND have time with your family.

You can have both.

Think in terms of and, intsead of either/or.

Maybe you’ve rebelled, or maybe you’ve conformed.

But what do you really want?

Comment below which path you’ve been on for the past 5 years, and what your game plan is now.

– Alex

Images: used with permission from picjumbo and


Wtf Thumb

My early 20s (until about 26) were literally the biggest clusterfuck you can imagine.

I went through a dozen jobs by the time I was 27, because I hated every one of them, I didn’t make much money, and I couldn’t justify putting off all the cool projects I wanted to do in my life.

So I didn’t do anything.

Looking back now (after having made a lot of progress), there were really three strategies that worked well for me.

That’s what I want to share with you in today’s video.

3 Strategies to Combat That “WTF” Feeling

First things first, which one of these three strategies do you think you could implement to see good results?

Are you currently using any of them?

And if you aren’t taking action… wake your ass up and start doing something, because ultimately that’s what worked best for me.

I didn’t get any slap in the face from God saying that I should go down a certain path, and so I forced myself to go down any path.

You can always course-correct along the way anyway, so don’t let yourself get stuck thinking about life, instead of acting your way through it.

Also, as my first video, do you want me to do more video?

What about video + article?

Just written?

Let me know below.




What if the biggest reason you aren’t taking action is a complete load of crap?

For years now, even before his death, there was a famous Steve Jobs quote circulating around the internet that came from his Stanford commencement speech.

“You can’t connect the dots looking forward, you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something: your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart, even when it leads you off the well worn path.”

Over the dozens and dozens of coaching calls I’ve done over the past few months, most of them were marred by one thing: lack of action.

Most of us are too busy being paralyzed because we’re confused as all hell.

Why would I ask that girl out again if I “wasn’t sure how I felt about her?”

Why would I take one of those three jobs when they all feel like boring, soulsuckers to me?

Why would I go down one career path when I’m not 100% sure if that’s what I want to do forever?

They all sound so logical.

And they’re all so wrong.

“None of These Are Really Calling To Me… I Just Need a Bit More Time to Figure It Out”


There’s this feeling that “if I don’t know what my passion is, or if it REALLY is what I like… why commit 100%? What if it’s the wrong path and I end up MORE unhappy, or lose time?”

Years ago when I was looking for jobs in my early 20s (and was both an idiot in how I applied, but also got zero offers), I felt this on a daily basis.

Eh… personal training?

Eh… some marketing job?

Eh… park ranger?

They all sounded like good ideas, but none of them really sounded great.

Not one of them sounded like that one thing I wanted to do for the rest of my life. And as a result, I didn’t do anything – since none of them were the clear winner in my mind.

Years and years went by, and I made shit progress in my life.

But it wasn’t until I realized a concept (what I called “God Vision” to someone once), that everything changed.

Now, it’s a principle I think about on an almost daily basis.

God-Vision is The Most Powerful Force in The Universe


God vision is what you cannot see in the future – but can only realize in the past.

In other words, if you were some divine being that could see your own life as a timeline, and all the micro experiences (and the big ones) that happened on that timeline, you’d be able to see first hand how much they served you and helped you.

It’s when that job you hated you took, but you got skills you later used to build a successful business.

For example, I took dozens (yes – dozens) of jobs from the ages of 23 to 28 that I didn’t necesarilly like, but I vetted them on one main thing: whether or not they would give me skills that I could learn and use later.

The issue of money was secondary, since I figured I could be poor now, learn what it took to succeed, and make money later.

The result?

I ended up using many of those skills from freelancing, marketing jobs, sales jobs – all things I hated – in order to build my own business. That became a crucial part of my story.

But if I never took the time to get those jobs because they weren’t my “dream jobs,” then I never would’ve acquired that skillset.

God vision in action.

Sometimes one step’s purpose is simply to lead you to the next step.

It’s when you passed up income to work for a crucial mentor, living at home, and instead, acquired more habits for success.

When I moved back from China, I moved back in with my parents until – get this – I was 26.

That’s a long ass time to move back in with your parents, especially if you’re fairly driven.

I decided to keep a string of part time jobs for almost five years, because there were other projects I wanted to work on on the side.

That was really important to me – meaning and purpose, more than anything else.

As a result, I made almost no money in my early and mid 20s, but I started little projects like Milk the Pigeon.

Milk the Pigeon taught me how to write, it taught me about blogging, it taught me about online business.

It introduced a new set of skills I never had, and guess what skills I used to launch my actual business?


It’s when you decided to learn random skills for fun, and not for a financial purpose, and five or ten years later, they come back to serve you.


When I moved to China at 23, I went because I wanted to take a few years off to study kung fu and meditation in some temples with monks.

Now even though I didn’t end up staying longer than a year, I ended up learning to speak, read and write Chinese – well – because I was putting in seven hours a day (four hours of class I paid for, and three hours on my own).

Everyone else was thinking of Chinese being useful from a business perspective, but I was just thinking one thing when I left my job:

“Fuck it, this is gonna be awesome.”

I had no intention of becoming a China based entrepreneur or capitalist.

So I learned a skill for fun.

And guess where it came back?

Next year, I’m starting school again for Chinese medicine – where knowing Chinese is a massive advantage when it comes to becoming world class at my craft.

God-Vision is simple: If you were God looking down – you’d be laughing, “It’s so perfect” and it is.

It almost seems like all of these events were related, and they had to happen.

But the reason why it’s so hard to trust the process is that:

  • A. it requires faith, which is scary as hell, and
  • B. we haven’t lived it yet

This is usually something you hear from people in their 50s and 60s, so if you haven’t lived it personally, it’s understandable that it’s scary as hell and makes no sense – how the hell can I trust the process?

The catch is that God vision only works if you live life right.

Here’s what I mean.

God Vision – How to Predict Your Own Future, Figure Out Your 20s and Live an Awesome Life

There’s a final scene in the movie The Last Samurai, where one of the Samurai leaders is having a flash back to a scene previously in the movie as he’s dying, about how death is perfect, like the cherry blossom.

When the cherry blossom is blooming in the spring, it’s this beautiful, short-lived perfection (which is a major tourist attraction in Japan), and is a metaphor for how quickly life passes.

Finally, as he lay dying near the end of the movie, he sees the tree again and says. “Perfect. They are all perfect.”

This is a part of that feeling Steve Jobs was referring to – you can only see the pieces connect in retrospect.

Life has to be lived forward but understood backward is another famous way to describe this effect.

It’s usually only at the end of a person’s life do you hear the stories about how they were in the right place at the right time, and ended up randomly meeting their wife, or a unique business mentor, or a book that impacted them.

It’s like the Stephen Spielberg two minute speech that’s been shared a lot lately: the intuition about what direction to go in is really subtle.

It’s not a massive god-slap in the face – but a constant, easy-to-ignore whisper in your ear.

There’s one catch: this kind of God vision, where shit just lines up year after year, only works if you live life deliberately and aren’t afraid to commit even when the path is dark in every direction.

Here’s what that looks like.

God Vision in Action: 3 Things To Do Daily


I recently was on the phone with someone, and I was sharing just how eerie the last five years have truly been (regarding the pieces lining up) since I forced myself to work hard.

There was the eerie connection about learning Chinese and ending up studying Chinese medicine – and getting to meet some cool mentors only because I knew Chinese.

There was the piece about learning to write here on Milk the Pigeon, and my first successful business being a blog-based business (my health one).

And there was the other piece about sacrificing a large chunk of my 20s for the hustle and skill acquisition which later served me well.

In the middle of the conversation I tried hard to narrow down what I consciously chose that helped make it work, and I realized it was three things.


The first skill to focus on is listening to those “little whispers.”

It’s the whisper that says that a guy or girl isn’t right for you, that a job “sounds” cool and pays well, but it’s not what you want, or that a certain opportunity is going to lock you down.

It’s like my intuition to avoid full-time jobs, so I could start projects on the side.

I didn’t know if it would work out, but I was literally unwilling to not try.


The second skill is to always choose opportunities based on Growth + love.

If you are thinking of moving across the country, taking a new job, breaking off something with someone, or are making a difficult decision, if you choose growth you always win.

Growth might mean taking a job you aren’t qualified for, and even though you feel afraid, you take it and decide to step up to the plate.

Growth might mean improving your career or work skills, it might mean starting a side project that you have no idea will workout (because it entails learning new things), or it might mean doing something hard in your business or job because you know you’ll learn.

Growth always pays off in god-vision land, because the more you grow, the more it impacts every part of your life.


The third skill is focusing on learning skills.

This is something I harp on all the time here, but in retrospect I realized that the most valuable things that I have now (even though I’ve long forgotten all those awful jobs) are skills.

Skills pay the bills.

Skills are how you build a business, get a job, or even get a romantic partner.

Having skills mean you are good at something, and you get skills in the arena.

So if you see an opportunity to develop skills – video editing, writing, blogging, marketing, selling, playing a guitar – take it.

And even if you don’t like your job now, if you can get skills, those skills might be the missing piece to your jackpot that comes together in your next job, business or opportunity.

That’s God vision.

You can’t predict the future, but if you do these three things you can have absolute faith they’ll come back and help you.

The trick is, right now you just don’t know how yet.

The One Thing To Remember

The ultimate question to ask yourself is simple – is this opportunity cool?

Would this give me skills to have?

And ultimately, is this the direction I want to go in?

If you keep doing that long enough, one day you’ll look back, with that faith and experience of knowing a life well-lived, and you’ll too think:

“It was perfect.”

– Alex

Thoughts on this? Share them below.