Back in October, I visited a few coaching friends in Vancouver Island, meeting them in person for the first time.
While at one friend’s house, we were discussing the things we felt incredibly grateful for. The same thought popped into my head that always does when I ponder what I appreciate most: my tribe of friends, family, and colleagues.
But this time, I had an insight.
Rather than vaguely trying to express this more to the people in my world, I decided I would be as intentional as possible.
I would craft hand-written letters to those who matter most. I would thank them and explain as best I could why they mean so much to me. Then, I would read the letter to them.
I’m not even close to totally completing this task (which I think is a good sign). But I have done several and would like to share what I’ve learned.
1) Expressing gratitude is euphoric.
Let’s get the selfish stuff out first.
Anyone who’s ever done a metta (loving-kindness) meditation knows the immediate rush of joy that comes from truly wishing someone well. We imagine someone we love and we picture them being free from harm and fear. We envision them being totally fulfilled. We see them laughing with the people they love.
This felt more impactful because I was sitting five feet from each person I read a letter to.
I could see their smiles and tears. I got to hug them afterward. I got to hear them stumble to find words that match the moment.
The idea of the exercise is to leave nothing up to the imagination. “Here are the specific reasons why I love you.”
Once that message gets across, the powerful connections I had with each person felt twice as strong.
2) This exercise is the easiest thing to do that brings life-changing results. Low input; very high output.
That sounds kind of businessy. Let me explain.
Each letter takes about 20 minutes to write. I type it out in a Google Doc first. This only takes about five to ten minutes because it’s effortless to write words that are sincere.
Then it takes another ten minutes for me to put pen to paper and transcribe the Doc.
The next time I would see the person, I would: tell them what I did, grab the paper as they panicked, and start reading it aloud.
In less than 40 seconds, our relationship would become wildly stronger.
I even gave this as a Christmas gift to my aunt and uncle. I have no idea if that’s just a cop-out from getting a “real” gift. But they both absolutely loved it so I think I’m off the hook.
3) There are a lot of things we keep to ourselves.
Here’s what I mean.
I’m lucky to have candid and loving relationships with my friends, family, and colleagues. But no matter how open and communicative we are with one another, there will always be thoughts and emotions we feel that the other person isn’t 100% aware of.
That’s also why I suggest doing a feedback exercise with those close to us. It paints a clearer picture of the lens our friends use to look at us.
We can let our actions tell the story. That’s a lovely thing.
But we can also remove the middle-man and get right at the heart of things. I’ll end with an example.
I wrote one of these letters to my dad.
In it, I told him what he did that meant the world to me. Last year, when I decided to not go back to school, quit my full-time job, and start my own business, I thought he’d be furious.
I was out front of my mom’s house, pacing on the sidewalk, when he told me on the phone I had his full-fledged support.
When I relayed this to him in my letter, he had no idea about the impact of that moment.
All this to say: We can always express our love and admiration for people more than we normally do. There’s always more to know.
I highly encourage anyone reading this to write just one letter to someone they appreciate. Tell them why they’re loved. Tell them what they mean. Tell them how much they’re needed.
This deck of cards is loaded with powerful questions which spark phenomenal conversations. When friends are over I’ll often take these out and take turns picking random cards and asking these questions in a circle.
Time flies every single time.
It’s like having a game night but you also get to have deep and intimate conversations with the people you’re with.
It’s strange to claim that I’m successful. But I certainly feel like I am.
As we’ve heard many times before, the word “success” means something different to everybody. It’ll mean something different to me even three months from now.
But for now, I can pay my monthly expenses comfortably, I have an amazing tribe of people in my life, and I use my time exactly how I want. Success.
I’ve read tons of self-improvement books and watched just about every motivational video on YouTube. There are loads of tips and strategies successful people teach us.
Having a routine, practicing mindfulness, failing often.
But I’d like to reword that last one.
Whether we’re developing our careers, our passions, or our relationships, I’ve discovered this truth:
In order to be successful we must be willing to look like a fool.
A healthy business comes from the willingness to put ourselves out there. I’ve messaged people asking to connect and they’ve ghosted me with a wide birth—probably thinking I’m selling something or working for a pyramid scheme. (Four people this year have straight up asked me, “Is this an MLM?”)
No, this is Patrick.
Early in my coaching career, I was terrified to reach out to others. My fear was that everyone would see me as a salesman when I just wanted to talk or reconnect.
Would I invite them to a session? Yes, maybe. But if they declined I didn’t care at all. I just love talking to people.
These fears were beaten out of me as I continued to reach out to people every single week. Now when someone doesn’t respond or ghosts me, I couldn’t care less. Who’s next?
As far as my passion for chess…
I started playing consistently during lockdown last year. One of my best friends said we should play.
It was something we could do online together. And we’re both competitive so I had the drive to improve. My sole purpose for several months was just to beat him. He was better than I was and each time he beat me it stung.
But I kept coming back for more. I started studying and practicing each day. Here’s my rating over the past 12 months.
Notice the dips and plateaus. Those periods were not fun. They were discouraging.
But like the stock market, if we zoom out and look at the big picture, the long term, we can see that I’ve only gotten better as I’ve stuck with it.
Chess, like many things, goes like this:
Step 1: “I’m getting pretty good! I feel like I could beat anyone….” Step 2: “I’m not sure I even know the rules. I suck. Maybe I should switch to checkers.”
And the cycle repeats. At every level.
The point is, when I’m not feeling on top of the world, I play with less confidence. But I play nonetheless. I may get destroyed and that always hurts…but if I just keep at it, the graph will continue to go up.
And finally, relationships.
A turning point in the health of my friendships came when I decided to be completely candid with my thoughts and feelings. In other words, I became good at having difficult conversations.
Speaking my mind. Setting boundaries. Being vulnerable.
I’m lucky to have a phenomenal group of friends, and it has been through my willingness to be open that these relationships have grown even stronger.
It can be quite scary, but if we are willing to risk foolishness, we’ll get good at just about anything.
Last night, I went over to my best friend’s house for dinner.
He and his partner were telling me about the move to intentionally add alone time into their relationship. Now every Tuesday around 4pm, they take turns leaving to go do something and give the other person the house to themselves. Tongue in cheek, they’ve been calling it “Fuck Off Day.”
It’s funny because a person could hear this and think, Oh, you’re trying to spend more time separated...sounds unhealthy.
When in fact, it’s one of the healthiest things I’ve ever heard a couple do.
They have an incredible relationship. And this practice is intended to maintain that strength.
I’m not an expert in love…but this truth can be applied to everything else in our lives:
Space from people, environments, and activities (especially ones we love) is essential.
Let’s go through some examples in order.
We all need alone time. We need to know what it’s like to simply sit with our thoughts and emotions.
I used to think I was just a wildly extroverted guy. Then I realized I was just surrounding myself with people so I never had to confront my anxieties. When we’re alone, there’s nowhere to hide.
Aside from that, time away from those we care about creates room for us to miss them.
It’s in someone’s absence that we truly notice what they bring to our lives. Until they return. We can’t fully appreciate something until it’s taken away from us.
Since I moved out of my mom’s house, we’ve grown ten times closer. She’s not my roommate anymore. She’s my amazing mother.
When I visit friends from other cities, I cherish every hour of conversation I have with them. I know that when the weekend is over, we’ll go back to our lives hundreds of miles apart.
In breakups, we can logically know that it’s for the best…yet we still feel the agonizing pangs of loss not having this person to laugh or be romantic with.
All this to say: We need space from people to solidify how much we love and appreciate them.
Why do we take vacations?
For the Gram, yes. But also to just fucking get away.
Away from our routines, our neighborhoods, our kitchens.
There’s something liberating about being in a totally new place. We’re often not even sure what the place is going to look like or what it has to offer. We just know we’d like a change of scenery.
I take one trip every month. Sometimes to another state. Sometimes out of the country. Why?
Because I work on weekends. Several of my clients work nine-to-fives and I don’t do calls on weeknights. That means I often work seven days a week. And that means I can only take so much before I have to get the fuck out of here.
I love this office but after a certain amount of time, any room can feel like a prison cell.
So I go somewhere. I visit a buddy. I see my family. I go hiking. Sometimes I just take the weekend off and host a friend here at my apartment.
It’s actually nice to not do my morning routine for a few days. But then, after taking that space, I quickly crave my old environment. I miss my desk, my roommate, my bed.
Then when I return home, I feel refreshed. I get back into my habits and rituals feeling reignited.
But there’s a reason I don’t play it for eight hours a day. It’s the same reason I don’t do anything for that long.
I’d get sick of it.
I had a session yesterday with a super ambitious salesman. He loves his job and is always eager to do well and help his team.
But the job is so time-consuming that he feels he doesn’t have any time for himself. So we created some boundaries for him to set and build that time (i.e. space).
I asked him: “What would you be able to do with the free time you create?”
He responded immediately: “I’d do my job better.“
He wants space from his job so he can be more present and capable when he’s in it. That’s how I feel about chess, coaching, and everything else. That’s why we need rest days from the gym—to allow our muscles to rebuild themselves and recover.
Intentional time away from the people and things we love strengthens our relationships with them.
Between people dying, hearts breaking, and a million other things which make us physically ill…we’re guaranteed to feel powerful negative emotions at times.
Yesterday, my coach told me, “There’s no system for grief.”
In other words, sometimes we’re sad and we don’t fully know why and there’s no formula to make it go away right now.
We have to just sit in it. And learn from it.
As readers of this blog know, I try to find the lesson in everything I do. After a painful experience, I allow myself to feel my feelings, and then I’ll ask things like:
What was the value in this? What have I learned? How can I use this as an opportunity to grow?
It doesn’t make shitty circumstances and more pleasant. But it is a long-term strategy for drastically improving as a person.
I handle myself with grace and respect when it comes to breakups, tough conversations with friends, and uncomfortable business dealings. I don’t take things personally and I never lose my temper.
How have I gotten so good at these things?
Because I was shit at them in the past.
I’ve tried to shame women into being with me (oh, to be 20). I’ve treated friends like garbage until they did what I wanted (sorry, Phil). And I’ve been stunned and speechless on the phone when a potential client told me “No thanks” (this year lol).
It’s through moments like these—memories that make us cringe—where the real growth happens. If someone doesn’t have any cringy memories, I assume they’re the same person they were in high school.
I treat women with respect because I know from experience how awful it is when I don’t. I’m open and honest with my friends because I’ve seen how sustainable and fulfilling that is over being passive-aggressive. And I’m detached from outcomes in my business because I’ve felt the agony of obsessing over a result and it not going my way.
It sounds David Goggins-y, but we learn from pain. Only if we let ourselves, though. Only if we seek the lessons.
We all want wisdom. But we don’t want the thing that brings us wisdom.
Until I was about 23 years old, I’m pretty sure I was a compulsive liar.
I lied about: my sex life, my skills, and stories which may or may not have happened to me. The goal was to create a Dillan who was way cooler, more impressive, and more capable than the Dillan I was.
Not only was I keeping reality away from my friends and family. I was also muddying my own lens of the world around me. I began believing the lies I was telling.
I also trusted people less. If I wasn’t being honest, how easy was it for others to be dishonest too?
Studies show that people who are carrying a gun suspect way more people to also be carrying a gun. So too with lying.
One of the heaviest burdens a liar carries is having to remember all that they said.
In my junior year of college, I got caught in a lie. I told one person something that contradicted what I told another person. The memory still makes me cringe. I felt like a child who got caught lying about stealing a cookie.
After that moment of disgust, I set out to intentionally break my habit of lying. It was fucking hard and took me about three years.
Even to an honest person, setting out to not tell a single lie is quite the challenge. It’s almost ingrained in our culture to spare the feelings of others and tell white lies to be polite.
I just finished a book—Lying by Sam Harris—which debunks every reasonable-sounding argument for telling a lie.
My two biggest takeaways are:
1) Lying erodes trust in the people we care about (both consciously and unconsciously).
I have a friend who’s one of the kindest and most compassionate people I’ve ever known. But one time, we were hanging out and someone texted her seeing what she was up to.
Not wanting this person to know she was choosing other friends over her, my friend lied. She said she was just chilling for the night to get ready for an early morning.
We laughed it off, but I remember thinking, Has she ever done this to me?
Now I’ve seen that she’s willing to lie to a friend. Whether we like it or not, I’ll never trust her 100% when I invite her to something and she says she can’t go.
2) Fake praise or encouragement is not kind; it’s disrespectful. It wastes a person’s time and morphs their grip on reality.
False encouragement is a kind of theft: It steals time, energy, and motivation that a person could put toward some other purpose.
Sam Harris, Lying
This has to do with short-term vs. long-term thinking.
If we give open and honest feedback (with grace and permission, of course), in the short term we may risk hurting a person’s feelings.
But in the long term, we accomplish a number of things. We…
• become a trusted confidante • genuinely help this person improve • cultivate a deeper relationship with this person
Giving and handling feedback well is its own separate conversation. But when I create something, I don’t want people to tell me why it’s awesome. That may feel good for four seconds, but what I really want is to build something valuable.
As uncomfortable as it can be, I can only accomplish that by having people I trust point out my blind spots and mistakes.
An essay is always improved after a round of edits.
On the other hand, if I’ve only been told that my thing is perfect…when I share it with the world and no one likes it, I’m left confused and heartbroken.
We can avoid that by simply being honest.
Where do you tell lies—even white lies?
How difficult would it be to not tell a single lie for the next seven days? I encourage you to try it. It’s more liberating than you may think.
In the past four years, I’ve had debates, discourse, and disagreements about politics, feminism, religion, race, transgenderism, vaccines, and more.
Some were heated and aggressive. Some were fun and fruitful.
I handled myself quite well during some. I sounded like an ass during others.
It doesn’t matter how much we connect or get along with someone else. We’ll never agree with 100% of what they believe. Disagreeing is a natural part of the human experience.
Through my conversational struggles and from the many mistakes I’ve made, I’ve learned three helpful (yet difficult) rules for having more productive disagreements.
Feel free to disagree with them (get it?).
1) Come to terms with this truth: We can never force someone to think, feel, or believe something. They have to get there on their own.
We are not creatures of logic. We make decisions based on emotion and then justify those decisions with logic.
In countless disagreements, I foolishly thought that if I just brought up another point of juicy rationale, I’d crack the other person and they’d see things the way I saw them.
Confirmation bias plagues us all. It will always be easy for us to pick and choose the (supposed) evidence which fits our narrative. We decide what we want to be true and identify with that belief. Then, if someone disagrees with that belief, it feels like they’re disagreeing with who we are as a person.
Yesterday, my friend told me about a heated debate between his two friends regarding the COVID vaccine.
One friend was arguing that the vaccines are probably not safe. He sent a screenshot of a well-sourced article listing the possible negative side effects.
The other friend then went to that same article and screenshotted a paragraph that was conveniently left out: the conclusion which said that the vaccine was ultimately proven to be safe.
I heard this part and thought that would be the shutting of the door to their argument. But the friend merely brushed it off and continued with his disputes.
With the power of the internet, we can find millions of people who agree with every possible opinion known to man. There are people with PhDs who believe the earth is flat. There are intelligent people who think the planet is 6000 years old.
Whether it’s opinions about vaccines or about our favorite athletes…our default is to cling to evidence that supports how we already feel and to shy away from evidence that challenges our beliefs.
Since that’s the case, we cannot ‘logic’ our way through a disagreement.
2) Ask way more questions.
There are several reasons for this.
Firstly, it’s crucial to understand fully what we’re arguing against. The last thing we want to do is misrepresent someone and challenge ideas they don’t actually hold.
We ask questions to paint a crystal clear picture of what they’re actually thinking.
A strawman is a fallacy in which we argue against the worst possible representation of someone’s point.
Example: “Oh, we need to do something about climate change? So you just want us to stop driving cars and stop having kids, huh?”
No…that’s not what they’re saying. That’s a strawman.
By asking curious and clarifying questions (not leading questions meant to achieve a ‘gotcha’ moment), we’re able to steelman. This is the opposite of a strawman, in which we’re able to articulate someone’s opinions perfectly.
A steelman would have us say: “So just to be clear, you believe…” Then they would say: “Yes.”
That has to be our starting point.
The second reason asking questions is so effective is it demonstrates to the other person that we’re not here to attack them. The more curious we are, the more we show we just want to understand them, the more their guard will drop.
This isn’t a trick. We want everyone involved to lower their guard and feel safe to express themselves without reacting in a defensive manner.
Curious questions make it a conversation, not a debate. This is ideal. Debates have winners and losers. But in great conversations, everybody wins.
The final benefit of asking questions is it adds scrutiny to the conversation, exposing the true strength of the person’s argument.
While this should never be the goal of asking questions, it’s possible that the person “defeats” themselves with their own words. It’s a great way to see if this person has given thought and research into this thing they believe or if they just want to believe this thing.
I recently had a disagreement over the COVID vaccines myself. (To be clear, I’m not super passionate about vaccines. It’s just come up a ton in recent months so it’s fresh on my mind.)
My friend who was super wary of the vaccines was sharing his opinions. I did my best to just ask questions. As I did, I felt that their answers were on shaky ground and I found many holes in their arguments.
There were a lot of “I don’t know’s” and “I don’t remember’s.”
Again, I wasn’t trying to slam dunk this person I have a ton of love for. I just wanted to get a clear picture of their beliefs.
Asking questions is hard, especially when we don’t feel curious at all. Curiosity is tough to fake. But it’s the only way to ensure nothing gets lost in translation.
3) Separate the person from the argument.
We’re not arguing with people; we’re arguing with ideas.
I could go on for hours about how much I hated having Donald Trump as our president. But I’m also super close with people who absolutely loved him.
That doesn’t mean I actually hate these people. It just means I don’t connect with their ideas. We don’t need to agree with someone to hug them or to have a beer with them.
So in a disagreement, it’s powerful to avoid saying things like:
• “Where you’re wrong is…” • “What you don’t see is…” • “I disagree with you on…”
With phrases like these, it sounds again like we’re disagreeing with them as a person.
It’s better to say things like:
• “My problem with that perspective is…” • “That argument to me is…” • “The way I see things is…”
With phrases like these, we make it apparent that we’re just discussing ideas. It’s not a battle over who’s more righteous, more intelligent, or more sophisticated.
We have to pick our battles. I’ve ruined social events because I thought it was the perfect time to argue against Catholicism.
But we should also feel safe and free enough to express ourselves. This can best be done if we change our goals for disagreement.
Instead of wanting to win, we should want to collaborate and learn.
“Seek out people, books or ideas that contradict your current beliefs and one of two things will happen…A) you will discover that you are wrong or B) you will improve your arguments for your own ideas.”
I had an incredible phone conversation with one of my best friends yesterday.
They’re usually great, but this one really hit all the nails: a ton of laughter, business updates, and vulnerability.
One of the silver linings of the pandemic has been the multiplication of how much I value my friendships. I find it vital to go out of our way to visit and maintain communication with the people we share our lives with.
We all have those friends with whom we can go a year without talking to and then just pick right back up where we left off. That’s lovely…but if it’s a close friend, I see that as an utter waste.
Let me explain.
I’m 27. I started my own business this year, am single, and have no kids. I’ve never been more career-focused than I am right now.
All this to say I’m hyper-aware that we’re all living our own lives. We’re stressed. Many of us are still figuring out who we are and what we want. Some of us have families. It’s not like high school where we can spend every weeknight and weekend having fun with our buddies.
However, since that’s the case, there’s never been a better time than right now to sustain healthy and fulfilling friendships.
• one of my best friends ghost me out of his life with no explanation to this day • friends get arrested • friends have quarter-life crises
It’s when we’re the most anxious, the busiest, and most overwhelmed that we need our friends the most.
If we let a year go by without any communication…yes, maybe we can pick right back up. That’s fine. But how many total hours of laughter, connection, and memories did we miss out on?
I love knowing what my friends are working on, are afraid of, and are thinking about on a consistent basis. I’m not saying I need to talk to them every single week, but more than twice a year is preferable.
We can start small. That friend we see once a year…we can bump that up to twice a year. We can set up a monthly call with our busy friends with kids.
It feels like work. Because it fucking is.
Let’s assume the major facets of life are health, wealth, and relationships (broadly speaking). I’ve noticed we put a ton of effort into working on our physical health, our mental health, and our careers, but we sort of expect our relationships to just take care of themselves.
When really they’re just like anything else important to us. They require effort, practice, and collaboration to figure out what works and what doesn’t.
When I’m an old ass man, I want to look back and think I’m glad I did…as opposed to I wish I had…
Right now, I’m so glad I had that phone call with my buddy. And I’m looking forward to visiting him in two weekends.
It’s his answer to: “How can I as a young man be better at talking to women?”
But I think it applies to all facets of life: making friends, being a great communicator, or building relationships in general.
Treat every single human being with the same amount of love, respect, and honesty. It doesn’t matter what their sex, race, job, weight, or age is.
Be curious about people. Exchange stories. Ask questions. Try to build something together.
“Friendship happens on the way to something else. If you “try to meet new people” it feels weird and forced. The more you aim for friendship, the more it eludes you. But if you aim to learn or achieve something with others, friendship happens naturally during the shared pursuit.”
These are all things I’ve been working on for the past year as I run my own business. In order to sustain my health, wealth, and relationships, I have to set boundaries for how I expend my energy.
But where did this all begin for me?
In April. Here’s what happened.
After joining my online coaching program in March, in the span of one month, I was called out by four different colleagues for needlessly apologizing for things. I learned how hesitant I was to stand up for myself.
One of those colleagues was a woman who told me she decided to stop saying “Sorry” the month before.
I was struck by this. But it took me several months to understand how I felt about this philosophy. Well…here’s how I feel about it.
I tried it out for a month or two. To be honest, it felt fucking great.
The first thing I noticed was how automatic saying Sorry was. I would open my mouth to apologize for something I didn’t do or something I had no control over—a dog barking, a broken appliance, the fact that I wasn’t available for something. Catching myself, I would promptly close my mouth and that would be that.
No one got mad. No one seemed to be waiting for some sort of justification.
But then something happened which made me question the whole experiment: I fucked up.
I did something that made a friend upset and I felt awful about it. This highlighted my issue with the whole “I don’t say Sorry” thing…Humans make mistakes.
What happens when we do something worthy of an apology? Saying we don’t apologize is to assume we’re perfect creatures. I’m happy to have the words “I’m sorry” in my toolbelt.
So where’s the middle here?
For me, it’s not about not saying Sorry. It’s about not always saying Sorry.
If Sorry is our default then it means nothing. If we say Sorry five times in one minute then it means nothing. If we apologize for things we had no control over then what does it accomplish?
But if we instead save it for things that truly matter, our words and actions have more impact on the people around us. Now, my friends know I feel deeply sorry when I say so.
We don’t have to apologize for everything. We just have to be willing to apologize.