Apr 21, 2016

29 Things I’ve Learned In 29 Years

At the time of my writing this, my 29th birthday is a few days away.

29 laps around the sun… and I feel like I have experienced a fairly densely packed ride so far.

I’ve struggled, I’ve conquered, I’ve travelled, I’ve felt, and I’ve loved.

The following collection of words flowed through me in one sitting, and I’m going to share it, unedited, with you now.

My hope is that you take something from what I’ve learned and you’ll be able to apply it to your own life. And by reading this, perhaps you can either experience less suffering of your own, or find clarity and meaning in the suffering that you have already endured.

29 Things I’ve Learned In 29 Years


1. The things that we have the most shame and emotional wounding around are often our greatest gifts

Imagine that you had something that stuck out about you, in a physical/visible way, when you were growing up. Now imagine that you were teased about it. Regardless of whether someone said something nasty to you a few times, or multiple people said things to you about it relentlessly, you would carry a lot of emotional pain around that aspect of yourself for years (and likely decades) to come.

Well, this is how it works for everyone. Except instead of those things being visible, they’re internal.

We all gather the most emotional wounding around the greatest gifts that we have to offer the world.

If you have a sensitive heart and found it easy to love things, people likely made fun of you for how sensitive you were and how much you felt.

If you were highly emotional and quick to react to things with ferocity, people might have told you that you were being ridiculous/too much/crazy.

If you were deeply introverted and needed more time than most people to respond to things that were asked of you, people may have told you that you were stupid or ridiculed you for being too slow.

Whatever the negative messages were that you internalized about yourself from others, they undoubtedly surround some of the greatest gifts that you have to offer to the world.

A whole new phase of life is available to you when you stop trying to suppress, control, or minimize those seemingly ‘terrible’ thing about yourself and embrace and accept them for what they are. They are gifts, not burdens.

2. Kindness matters more than you could ever imagine

Kindness is the truest and most valuable form of currency available to us.

One time I was doing a speaking engagement outside of my hometown.

I gave a talk for around an hour, and for whatever reason, I felt like I really had to win over the crowd. They were not as receptive of a crowd as I was used to speaking to. Subsequently, I left the stage feeling more drained than I normally would (as public speaking is something that usually gives me a lot of energy).

After getting off the stage I felt ready to B-line it outside to get some fresh air. But before I could leave the room, one of the audience members swiftly approached me and clearly wanted to talk.

I would normally have said something along the lines of “I’m very much looking forward to speaking with you one-on-one, but I just have to recuperate a little bit by grabbing some fresh air by myself. Can we pick this up in ten minutes when I’m feeling a bit more centred?”, but this felt like a unique situation. There was some unique energy in his eyes that called out to me.

We stood in the corner of the room for at least twenty minutes and he told me about everything that was going on in his life (well, almost everything, as you’ll soon see).

He said that he was starting his own business, he recently ended a multi-year relationship, and he was having a challenging time making friends in his new city.

He talked most of the time, and I listened with a compassionate ear. I could tell that he had a really good heart and just needed someone to listen to him for a bit.

And that was that, or so I thought.

He reached out to me on Facebook a few days after the event and confided in me that he had been considering killing himself that night. Then his friend told him about the event, he came out, he enjoyed my talk, and felt compelled to speak to me. He then told me something that stuck with me to this day.

He said “Had you not listened to me with such genuine care and compassion, I probably would have gone home and finished myself off that night. But to receive such loving kindness from a total stranger who didn’t benefit in any way from listening to me, it gave me faith in people again.”

The moral of the story… kindness saves lives. And even if every act of kindness doesn’t save a life in any trackable kind of way, it still ripples out into the world and benefits all of humanity – whether you can see it or not.

3. You have to create your art if you are to ultimately feel at peace with yourself

One of my favourite quotes of all time comes from the guy who created the hierarchy of needs, Abraham Maslow.

“A musician must make music, an artist must paint, a poet must write, if he is ultimately to be at peace with himself. What a man can be, he must be.”

Whatever calls out to you from your heart/gut/intuition, the message must be heeded.

I find myself slipping into this mode sometimes. If I do too much coaching and don’t spend enough time writing/creating then I turn into a grumpier version of myself.

And creativity is not something that chooses a select few. Everyone is creative… it’s just that some people use their creativity and most others neglect it.

So whatever your thing is… your art, your creative process, the thing that you do that gets you into a flow state… you must honour it and engage in it regularly. This is one of the greatest self-care tips available to you. Do your thing, and do it often.

(Bonus: when you truly start honouring yourself fully by creating the kind of value in the world that only you can create, it becomes infinitely easier to stop judging other people altogether. The more ‘you’ you are, the easier it is to accept everyone else’s way of being.)

4. You will meet and attract intimate partners who love you like you want them to when you start loving yourself for the character traits that you have neglected

The people we attract into our lives should all be seen as lessons.

If you consistently attract intimate partners that have one aggravating thing in common, well, guess what my friend, that thing is trying to be brought to your attention for a reason.


– You attract three people in a row who can’t handle how sensitive you are? This is because you haven’t melted through the part of yourself that judges how sensitive you are.

– You attract a slew of partners who barely give you the time of day and they have to constantly be reminded that you are loveable? This is likely because you’re lacking in the self-love department and you still need to convince yourself (i.e. realize) that you are already loveable as you currently are.

– Your third significant other in a row tells you that you’re stupid? Maybe you have that same story in your mind about yourself and these people are simply mirroring the story that you internally perpetuate about yourself. The antidote is to gather evidence of your intelligence, and start to recognize your brilliance in every day life.

In all three of these examples, the way out of the pattern is to notice, love, and deeply accept that trait in yourself. When you start loving that part of you, you will begin to attract others who also love and accept that part of you. It sounds like magic, and that’s because it is. But it is still true.

warmth, warm hands, blonde, paris, love, thaw, cuddle, cuddles, cuddle buddy, slow sex, 29 things

5. There is no shortcut to putting in the work

Whether we’re talking about emotional processing, working on your career path, or keeping the home fires burning in your relationship, there are no shortcuts to putting in the work.

Yes, there are things that you can do that are more effective and efficient than other things, but there are no magical silver bullet solutions that allow you to avoid putting in any genuine effort.

Want to meet and attract a high quality partner who loves you for you? Put in the work to love yourself, put yourself out there, and have a trusted confidant guide you through the process and help to witness your blind spots.

Want to repair the cumulative damage that has been done in your relationship? It’s going to take communication, and time, and intentionality. It can absolutely happen, but it’s going to take work.

Want to build a business that utilizes your greatest gifts while helping a large number of people? It’s going to take time, and money, and it’s going to require you to dig deeper into yourself than you ever thought you could.

It all takes work. And there are no shortcuts.

6. You have to feel your feelings

People will spend years of their lives (and an untrackably high amount of emotional bandwidth) running away from feeling their feelings.

Terrible things happen to people. A lot of suffering will occur throughout your lifetime. This is unavoidable. But how you respond to the corresponding emotional residue from those events is up to you.

Your close friend dies in a car crash. Do you start drinking alcohol daily in order to numb away your pain, or do you sit in it and feel all of the emotions that are available to you to be felt?

Your significant other of several years breaks up with you. Do you go out clubbing and compulsively sleep with five new people this week, or do you call up your best friend and cry on their shoulder?

Your parent tells you that they’re disappointed in you. Do you binge-eat a pint of ice cream and a box of donuts in hopes that the sugar high will counteract their criticism, or do you journal about it and then talk to your therapist the next day?

The only way out is through. You have to feel your feelings. It’s rarely easy, but it’s worth it. You will save time, energy, relationships, and you will stave off illnesses by allowing yourself to feel what is available to you to be felt.

7. There comes a time when feeling your feelings and constantly rehashing the past becomes damaging

Emotional processing has a shelf-life.

Their is an endless amount of self-work that we can do. You can always scrape up some old emotional residue and think that you’re making progress because you’re feeling something. But at a certain point in your journey, you have to allow the past to be the past and move forwards.

For example, if someone told you during your childhood that you were deeply flawed and unloveable, it would be beneficial to uproot this belief in a therapeutic setting, journal about it, and feel the pain that your child-self wasn’t allowed to feel at the time… but then after a certain amount of rehashing, it would be time to prove that belief wrong by allowing people to love you as you are.

You would feel it for a while, and then move into a more behavioural approach.

Afraid to spend money? Spend some of your money in a safe, calculated way.

Afraid that you’re unloveable? Let yourself be loved.

Afraid that you’ll get kidnapped if you go travelling outside of the country? Go travel, and gain the experience of not being kidnapped.

Our stories only have as much power over us as we allow them to have.

8. Always have something to jot down notes with

“The weakest ink is stronger than the strongest memory.” – Chinese proverb

How many thousands of brilliant ideas have passed through your fingers because you forgot about them moments after the thoughts came to you? Well, you’d never know because they aren’t being recorded.

One of the highest leverage habits that I have adopted over the past few years is to always have something to write with on hand. Whether I have a fully charged phone on me, or a miniature Moleskine notepad, I always have something to jot my thoughts down into.

Because of this simple seed habit, my emotional processing has sped up, my self-awareness has increased, my relationships have improved, and I get more done in less time.

9. Follow your heart, even when it doesn’t make sense to do so

Sometimes you will get messages from your heart that don’t make any sense. Maybe they seem poorly timed. Or out of alignment with what you’re doing, or what you want. Or just plain wrong.

Notice that I said you’ll get messages from your heart and not from your mind. Even if you’re a seasoned meditator, your mind is basically a 24/7 shit-show. I’m not saying to listen to and honour your mind’s messages.

Your heart is the wise one.

The messages that you receive don’t need to make sense… the fact that you want it to make sense is just your ego/mind grasping for certainty where there is no certainty to be found.

Your heart’s message doesn’t need to make sense to your rational mind. It just needs to be listened to and honoured.

29 things, 29 lessons, 29 life lessons

10. There is no such thing as certainty – ever

I once had a client come to me who expressed a desire to want “100% unwavering confidence” in the fact that he was deciding to marry the right person.

When I dug into why this was such a strong need for him he said that (1) his parents had divorced when he was young and he felt that it really messed him up, and he didn’t want to pass on any emotional wounds to his future children, and (2) he felt like he was a catch and he wanted to make sure that he wasn’t settling.

So, understandably, the first words out of my mouth really bothered him.

I told him, “I can guarantee with 100% certainty that you absolutely ARE settling by choosing to marry this woman.”

He looked stunned. “What…? Are you serious? How can you say that without even knowing her?”

I told him that life is constantly about making sacrifices… about ‘settling’ in one form or another.

By deciding to live in one city, you are saying no to thousands of other options. By striving for excellence in one career path, you are saying no to millions of other potential careers. By choosing to marry one person, you will only ever be married to their quirks and no one else’s.

Miraculously, he accepted this reality faster than I expected and he felt a huge weight lift off of his shoulders.

You will never have certainty, about anything. You will always be settling in some way, in everything that you do. But you do the best you can with what you have, and you go from there.

You can experience a high degree of felt truth when you listen to and honour your heart, but truth, certainty, and your intuition is a constantly shifting reality. So stop grasping for “certainty.” It never existed in the first place.

11. Doing everything in your power to understand yourself to the greatest extent possible will pay dividends in every area of your life

There’s no such thing as being too self-aware. And it is absolutely something that you can cultivate.

First, cultivate self-awareness internally by following the note-taking/journalling exercise referenced in point #8, and then supercharge your self-awareness by doing the following.

– Ask your parents/grandparents/people who knew you when you were young to tell you about your personality from the ages of 2-6 years old. When you’re young, you are the least socially conditioned… and in many ways you are in the most authentic state you’ve ever been in. Ask your relatives what your nature was like when you were a kid, and you’ll gain valuable insights as to who you are at your core.

– Do PAID personality tests, online and offline. Goofy little online personality profilers are fun and all, but they’re generally less effective compared to the tests that you have to put any amount of money down for. For starters, check out the DiSC Classic Profile, StrengthsFinder, and Myers-Briggs.

– Hire coaches specific to the area of your life that you’re looking to work on.

Once you have a thorough road map of how you work as a person (especially having cultivated a heightened awareness of your ‘weaknesses’ and/or blind spots) you’ll be so much more effective in navigating your life, career, and intimate relationships.

12. Someone will always hate you, no matter how safe you try to play it in life

If you do work that you love, there will inevitably be someone there to attack it. Also, if you do work that you hate, someone will be there to attack that. You’re screwed either way, so you might as well be happy while being criticized.

No matter how safe you play it in life, there will always be someone there to disapprove of what you’re doing and how you’re doing it.

As of the time of writing this, I reach somewhere between 1-2 million people per month with my writing. And for every twenty messages that I get about how I’ve changed someone’s life for the better, I also get one message from someone telling me that they hate me/that my writing sucks/etc. And I’m 100% okay with that. It is a tiny, inconsequential tax in doing the work that my heart needs to do.

So don’t worry about whether you’re playing big or small… just do things that honour yourself and you’ll be able to weather the storm of haters with ease.

13. Your time will always be more important than money

People are far too generous with their time, and unnecessarily stingy with their money.

Reason being? You can always make more money, you can’t always make more time.

Here’s a true short story that perfectly exemplifies this point…

A fast food chain in tiny-town America once held a one-day promotion for a free small bucket of chicken. People were instructed to print off a coupon at home, and bring it in to one particular restaurant location on one specific day. Within a couple of hours, there was a lineup that wrapped around the block. By the time that many of the coupon-holders got into the store they had waited over three hours to redeem their coupon.

So to re-cap, they waited for over three hours for a bucket of chicken that cost roughly $6.

Now, if you asked many of those people if they would sit in your drive way and watch your grass grow for $2 per hour, most of them would have enough self-respect to say no. Because the hourly rate would seem to ridiculously low that it wouldn’t be worth it for them. And yet this is exactly what they were doing. By standing in live for over three hours they were valuing their time at $2/hour.

This might be a somewhat polarized example, but it speaks to a real fallacy in how people treat their time. They value their precious dollars, but don’t stop to consider how much time they waste in their daily lives.

So the more boundaried you can be with your time, the better. Say no more often. Guard your time like the valuable resource that it is.

14. Your health will always be more important than money

Over the past year I hit an energetic wall when I realized that I had been taking on an unsustainably high volume of coaching clients, while writing/creating less and less. In essence, I was prioritizing my revenue over my artistic sensibilities… and my heart hated it.

More is not always better. After a certain level of your basic needs being met, money really doesn’t equal happiness. Especially when you are chasing money while neglecting your health.

Your physical and emotional health, and the health of your closest relationships are true wealth. Financial wealth is entirely inconsequential by comparison. I have worked with too many emotionally unfulfilled multi-millionaire clients to believe otherwise. Ultimately, we are all searching for a deeply fulfilling love. Everything else is secondary.

control, slow sex

15. Just because something is difficult to get doesn’t mean that it’s worth your time to get it

Our funny little monkey brains place value on things that are difficult to obtain.

Half a million dollar sports cars are seen as a status symbol because they are only available to those who have excess resources to throw around.

We have crushes on celebrities because they seem unattainably perfect.

Some people spend decades of their lives chasing the reality of having built a 7/8/9 figure business just because it’s a challenging thing to do.

Well, just because a task is difficult, doesn’t mean that we should chase it down and try to conquer it. Or that it would be good for us to have achieved it.

If the challenging task is aligned with our core values (and more of a secondary reward) then, fine, go after it. Just make sure that you’re not trying to do/achieve/own a thing simply because it is a difficult thing to do. This tip alone can save you years of unnecessary suffering.

16. Be selective about the information that you choose to consume

There is a lot of noise in the world. Fear-based news, non-stop ads, and people gossiping in public settings are among some of that collective noise.

Be intentional about what thoughts you allow into your mind.

Not all feedback is valuable. Not all news is good news. Not all conversation between friends is healthy for you to hear.

Just like you’re aware that it probably wouldn’t be good for you to exclusively eat donuts, you’re similarly allowed to tune out what you deem to be unhealthy for your mind to consume.

17. Have a good thorough sweat at least once every week

Self-explanatory. It’s good for you on every level.

It helps you stabilize your mood. Reduces stress. Regulates your hormone production. Boosts your sex drive. Helps you sleep better. Makes you happier and more productive.

Exercise doesn’t have to mean spending time in the gym. It can be playing frisbee in a park, or dancing at a nightclub, or playing badminton for a few hours with a friend. Find a physical activity that you find fun and do it at least once per week.

18. If you consistently neglect your heart and the suggestions that it offers you, you will be miserable

Do you know that you need to end a relationship (intimate or otherwise)?

Is it time that you finally allowed yourself to start engaging in your passion project, if only on evenings and weekends outside of your 9-5?

Do you feel awful about how you treated someone years ago and you feel like reaching out to apologize?

If your heart is consistently sending you a message, it won’t quiet itself until you listen to it and act upon it. Your heart knows best. Honour it’s messages to you.

19. Sexuality is a million converging sliding scales… aka you are normal

Mainstream media tends to treat sexuality like a black and white issues. You’re either this or you’re that. You like these types of things, or this other type of stuff. On/off. Black/white. It’s all very dichotomous.

In reality, sexuality is much like personality… in that there is the same number of sets of sexual preferences as their are human beings in the world. Not only that, but everything is a sliding scale.

You might like rough sex 20% of the time, with men and women.

You might love being being physically and mentally dominated, but loathe experiencing any pain during sexual play.

You might want your partner to fuck you with a strap on while wearing a diaper.

Or maybe you only enjoy climaxing while you’re with your monogamous partner, the lights are off, and there’s loud music playing.

There are so many converging sliding scales of sexuality… it’d be impossible to condense them into a couple of hundred words.

Suffice it to say, whatever you’re into, you’re normal. You’re allowed to have a deeply fulfilling sex life. And there’s someone else out there with a high degree of overlap with how you operate.

sex toys that every couple should own

20. Sexual exploration, self-employment, and close intimate relationships will teach you more about yourself than almost anything else imaginable

Sexual exploration, self-employment, and close intimate relationships are some of the most potent mirrors that we have available to us. You learn about yourself and your self-imposed limitations constantly by engaging in any or all of these three tools.

When you let go and allow yourself to expand in one area, you also miraculously open up in the others. Nothing exists in isolation. Everything in our lives is interconnected.

21. People can love you if you don’t love yourself, but you will find it nearly impossible to receive it or believe it until you love yourself too

The old adage of “No one can love you until you love yourself” simply isn’t true. The existence of other people’s love for you is not contingent on you loving yourself. But you’ll definitely find it difficult to believe or receive the love of others until you have a decent amount of love for yourself first.

Working on self-love is a lifelong journey, and it’s a necessary one if we’re going to be engaging in any relationships that hope to thrive.

22. Your self-care is an entry point to durable self-love

You have to take care of yourself on a physiological level before you graduate to the emotional level of self-love.

Just like a baby intuitively knows that it isn’t loved when it’s physiological needs aren’t being met by it’s caregiver, your heart/body/inner child feel unimportant and unloved when you chronically deny yourself good sleep, healthy food, rest, and play.

Start with self-care, and move on from there.

23. Good friends are beyond invaluable

Our closest friendships train us in how we should be treated in our intimate relationships. If you have friends that love, support you, challenge you, and accept you as you are, you will be in a fantastic position to attract in a healthy love relationship. If you have friends who criticize you, hold you back, and talk behind your back, you’ll be well positioned to attract an intimate partner who does the same.

It is better to be alone (in terms of an absence of friends and in the context of being single) than to be in relationships with people who hurt you.

The right friends can be the launching pad from which all of your greatness springs forth.

If you have a small handful of deeply trustable, close friends, guard them with everything you have. Add value to their lives. Tell them how much you love them. Invest in your relationship with them regularly. They mean more to your happiness and development than you could even comprehend.

friend, overhaul, 29 things, 29 lessons, things i've learned

24. You can have it all, but you can’t have it all at the same time

You can be kicking ass and highly optimized in several areas of your life simultaneously, but if you think you’ll be able to rock a 10/10 in your health, wealth, relationships, and personal growth in the same moment, you’re in for a rude awakening.

I once had a client who was competing in a body building competition. He spent some time in the gym six days a week, and was being highly structured about his dietary intake. Every calorie was tracked. Every meal had to be prepped. He had to report in to a dietician multiple times per week. After a few months of training he confided me in me that his social life had been suffering because of all of the time he had been putting into hitting his physical ideal pre-competition.

I reminded him that he knowingly dedicated himself to this goal and that his social life was only taking a momentary hit. He would be able to resume it to his desired levels once this health bender was over, and he could check in with his values at that point once the goal was complete.

You can do extremely well in a few areas of life in any given moment, but you will never feel flawless in all areas of life. Nor should you aim for it. Perfection isn’t the goal… living, experiencing, and feeling is the goal.

25. When in doubt, take action

Imagine you’re in a new city, walking somewhere on foot, and you’re using your phone’s GPS to help you navigate your way.

If you come to a cross roads where you’re not sure which way is left and which is right, you can either stop and analyze your situation for an unnecessarily long period of time, or you can just head in one direction and see what feedback you get from your GPS.

Either you go in the right direction and you keep going, or you go in the wrong direction, get corrective feedback, and know to turn back around.

Life is much the same way.

Not sure if you should do something? Try it out. You’ll either like it or you’ll hate it. Either way, you’ll get the corrective feedback from your body and you can then act upon that new information.

26. Frequently check in with what you say your values are and what you actually put in your calendar

How often do you check in on the integrity of what you say is important to you versus what you actually make time for?

Maybe you tell yourself that family and close friends are the most important thing in your life… but you haven’t seen your parents in six months and you can’t remember the last time you got all of your friends together in one room.

It’s healthy and productive to occasionally call bullshit on yourself. Get painfully honest here.

What matters the most to you? Health? Achievement? Societal impact? Time with friends? Romantic love? Your children? Your sense of personal growth? Whatever it is, make sure the general make up of your weekly calendar is reflecting what you value. If you have too wide of a mismatch, it will start to weigh on you heavily.

You’re allowed to make time for your favourite things. Because again, life is about constant compromise. It’s necessary to take time away from some things to make more time for other things. Be selfish. Your time is yours alone, and you get to decide what to do with it.

27. There is a time to push forward with all of your might, and a time to slow down and tend to your wounds

Life is seasonal.

Sometimes you need to plant seeds, sometimes you need to harvest the crops.

You don’t need to hustle, push, grind, and build your way through life. You must balance your doing with being.

Sometimes you need to work hard, sometimes you need to relax softly.

28. It is nobody else’s job to give you permission – you have to give it to yourself

Want to approach that person that you find attractive? Want to create your art? Want to heal your relationship to sex/intimacy/your ex that you had a falling out with, etc.?

No one is coming to save you. You have to give yourself permission.

You can have anything you want, but you must pay for it. And the first step is to give yourself the permission of allowing yourself to go after it.

29. Everything is a journey. So make sure you’re engaging in journeys that you actually want to be engaging in.

Everything that you do on a daily basis is inevitably what your mind is going to become better at doing.

Building rapport in the relationships that you’re investing in. Going down your specific career path. Studying whatever you’re studying on a daily basis.

Do you want THOSE synapses to be getting stronger… or do you not? You’re allowed to let go of them if you know they aren’t serving you.

Make sure that the thing that you’re leaning into is something that you actually want to be doing. Otherwise, you’re wasting the most valuable resource available to you… your heartbeats.

29 years, 29 lessons. That was quite the deep dive. So I’m going to leave it there.

If this post resonated with you, feel free to share it with a friend or someone you love.

And thank you for reading this far. I wish you the best of luck in your journey.

Dedicated to your success,


Ps. If you enjoyed this article, you’ll probably also love reading…

All Of Your Suffering Was Worth It

This Is The One Thing You Always Have Control Over

Growth Feels Like Death, Because It Is Death

7 Simple Life Skills That Improve Everything

When Feeling Your Feelings Becomes Damaging



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