Getting a raise vs. having a kid

I got dinner with my old boss last night.

He recently got promoted to VP in his company. He’s also the recent father of two.

When I asked him about the new VP position, he calmly said, “Yeah man. It’s cool.”

When I asked him about his partner and kids, he lit up. He raised his volume. He smiled as he spoke. He talked with his hands. “I love it,” he said. “It’s my favorite job I didn’t know I wanted.”

I pointed out how much more excited he seemed about his role as a dad than his role as a VP. He told me that one influenced the other.

When he detached himself from wanting a promotion and focused his love and attention on his family and wellbeing…he got the promotion.

We so often chase something only to see it evade us. Like magnets repelling from one another.

Fulfillment. Friendship. Opportunites.

These come readily to us when we just stay present, provide as much value as we can to those we care about, and continue to do the things we want to do.

We work on ourselves. We sharpen our axes.

We get what we want when we don’t care about getting what we want.

It’s never enough

Pizza crusts on a plate

Yesterday, my best buddy and I won $1,000…each.

It was a raffle for subscribing to The Hustle, an extraordinary newsletter on the worlds of tech and business. I’m a sucker for those things…

“For each person you refer, you both could win a billion free socks!” Or something like that. My friends often roll their eyes. But look who’s laughing now.

The $1K comes in the form of an Airbnb gift card. This is phenomenal because it feels like I’ve won free experiences, as opposed to the less-sexy prize of $1K in my savings account.

I’d be grateful either way. And this blog is about that ‘g’ word.

God.

Lol jk. It’s about being grateful.

Something happened five minutes after I saw we won. Something I’m embarrassed to share.

I started thinking about all the trips I have planned in 2022 and about how nice it would be to have my lodging paid for. Brooklyn in February, road trip to Florida in April, NYC again in May, European road trip in July…

Then I thought, Ah man…There’s no way $1K is going to cover all of that. If only it were $5K…

I actually thought that. It took five minutes for me to feel like a free $1K wasn’t enough! Am I insane??

I immediately laughed at myself. “Yeah Dill, some people really have it awful. What ever are you going to do?” Silliness.

Unless I’m a sociopath, the point of sharing that is to highlight the human tendency to always want more. That’s why conditional happiness (or the hedonic treadmill) is a dead end.

Conditional happiness: “I will be happy/fulfilled/satisfied once I have or do this thing.”

Then we get whatever that thing is and we are happy…for five minutes. Then we go right back to our default state.

One of my clients got his dream job, his dream car, and is financially set for life. He told me that none of that brings him sustainable fulfillment. Robin Williams was loved by the world, made millions of dollars, and pursued his dreams successfully. And he hung himself. I got free God damn money and got upset it wasn’t more.

It’s up to us to build a default state of gratitude and appreciation.

I’ve decided to forgive The Hustle for only sending me $1K. Please send your condolences directly to my email.

Football is scary

An American football on the grass of a field

Yesterday, my mom took me and my uncle to a Washington Football game.

The only sports I care for are MMA and soccer, but I always say yes to a live sporting event for three reasons:

  1. I’ll enjoy any event if I’m with people I care about.
  2. It’s always fascinating to see people who are at the highest level perform (in this case, NFL players).
  3. The people-watching is golden.

Today, I want to talk about that third one.

Growing up, football was my favorite sport (sorry, Bow Wow). Then around high school or college, I noticed something that turned me away from it.

People truly treat it like a religion.

Don’t get me wrong, I love how a sport can bring people together and evoke powerful emotion in millions of people. I enjoy listening to folks passionate about a sport discuss the business and inner workings of what makes the game tick. I enjoy the roars of crowds at games like the one I went to yesterday. Depending on the UFC bout, you can find me standing and screaming at the TV.

But what leaves a sour taste in my mouth is hatred—disgust for other players or fans (i.e. human beings) because of the jersey they’re wearing.

I’m not saying every single football fan is filled with rage, but it’s not uncommon.

When I was in high school, I would go see my team play against our rivals. I despised them. I wanted them to lose every game. I was convinced I didn’t like them as people without ever speaking to a single player.

Why?

For no other reason than the arbitrary fact that I attended my school. If circumstance led me to attend the rival school, I would’ve felt the same about my school. If I grew up in another state, I wouldn’t have even known either of these high schools existed.

Thus the religious context comes into play. When I see babies or toddlers with Steelers jerseys on, I doubt those kids chose to be Steelers fans. Likewise, if we’re born into a Muslim or Hindu family, we’re unlikely to be raised as Christians.

At the game yesterday, I saw fans flipping other fans off, telling them to “stop fucking talking,” and ironically clapping in their direction when their team did something good. There was an essence of mob mentality, meaning I saw people do things they would never do if they were in a living room with just one opposing fan.

There was no genocide, but in what other contexts do we act this aggressively toward other people?

I’m probably being overly dramatic. I just think it’s odd to see people feel so identified with a group of people they’ve never met. And it’s not even that group of people; it’s the shirts they’re wearing.

This blog likely triggered a few football fans. Apologies.

But maybe that proves my point?

The R word

Every now and then I talk about Resistance.

The concept comes from The War of Art by Steven Pressfield—a book I read once a year.

Resistance is the invisible force that keeps us from doing the things we want to do and living the lives we want to live.

It takes many shapes: fear, procrastination, justification, anger, shame…

It says: “You don’t have to do this right now. Do it later. It’ll be easier and more enjoyable if you do this in the future.”

Most of the time, Resistance sounds reasonable. We can’t start until we do this thing, until we have more knowledge, until we have more confidence.

I’m writing a book. Each and every time I sit down to start typing, without fail, I find reasons to wait. I set out to begin writing at 9am, but won’t start until about 9:45.

Readers of this blog know I’m not a big grind-hustle-discipline guy. I don’t think we have to torture ourselves to live a life worth living.

But the simple truth is we don’t get something from nothing.

There are plenty of things worth doing that we won’t feel like doing. Whether it’s something small like reading or working out, or something with higher stakes like starting a company.

We can just start. It’s time.

I’m sad and I don’t know why

A gorgeous winter landscape with the Sun going down

Maybe sad is the wrong word.

Last week, one of my clients said the same thing happens every winter: From December to February, he just wants to quit his job, not talk to anyone, and smoke weed by a campfire.

I feel that.

Not that I really want to do any of those things, but I do feel a twinge of sadness or dissatisfaction and I can’t pinpoint the source.

Yesterday, I called my best friend to tell him that and see what his thoughts were. But after ten minutes of just chatting and laughing, my state had completely changed.

I had energy. Things felt light again. What happened?

Aside from being a social creature who gets filled up by human conversation…I was reminded of an inconvenient truth.

Our states and conditions are constantly changing.

Happiness is an emotion. Just like rage or sadness. I don’t think we can genuinely “be” happy; I think we can feel happy. Being assumes it’s ongoing and everlasting.

This is why I don’t strive for happiness. My goal is fulfillment.

We can be fulfilled and still be sad, stressed, or uncomfortable. So during times like these—when it’s colder and darker than usual—I stick to my fulfillment system:

Every day, every week, I do the things I love and try to get better at them: Quality time with friends/family, coaching, chess, exercise, reading…

Yesterday, after work I wanted to:

• cancel a run with my buddy
• skip the gym
• watch YouTube and porn until midnight

I didn’t do any of that. Despite my mind telling me what was good for me, I stuck with what I knew: You won’t be happy to do these things, but you’ll be glad you DID them.

It’s true every time.

Likewise, when I choose not to do the things I know I regret after—watching porn, staying up on my phone, ordering $40 of DoorDash—I’m thankful 100% of the time.

How the hell do I conclude this blog?

Basically, I’m feeling grey at this point in time, and that’s okay. Nothing’s wrong. There’s nothing to fix.

I’m confident that if I just keep living with my values and doing the things I know make me a fulfilled person, the grey will subside.

Meow.

Am I an asshole?

Here’s one of my favorite parables (I’m not actually certain it’s a parable, technically):

If you go out into the world and happen to run into an asshole, you just met an asshole.

If during your travels, you run into 30 assholes, you’re the asshole.

I used to work with this woman who thought the world was out to get her on a daily basis. She complained about people, judged others, and gossiped constantly.

Each week, it seemed like something wildly unfortunate and unfair would happen to her. This confused me until I realized an odd, almost spiritual truth:

The world is what we think it is.

Whether we see life as a gift or as a burden, it all comes from within.

I used to think people sucked. And lo and behold, they did.

But once I started working on myself, improving my life, and seeing people as fascinating…they became much more lovely.

It’s all one big self-fulfilling prophecy.

First time at chess club

Last night.

I found out there’s a chess club in my city. They meet every Tuesday night in the Whole Foods cafe.

I showed up with my chess set and clock to a bunch of old men sitting and playing casual games.

For some reason, I was nervous on my way.

Not that I would get my ass beat (in chess). Something about hopping into a new community of people.

I guess at 27, I’m still giddy about making new friends.

They were some of the kindest people I’ve ever met. The youngest guy (he was in his forties) welcomed me to his board for my first game.

I played two gentlemen, two games each. I absolutely destroyed them.

We played for two hours until the grocery store closed. I told them about my first tournament coming up this month and they were super supportive…as if we’ve been teammates for years.

Needless to say, the nerves were gone.

Things are never as bad as the possibilities our minds make up.

I’ll see them next Tuesday.

Let the dog cry

A Golden Retriever looking up and smiling

I’m dog-sitting for my friends.

Each morning, after breakfast and our long walk, he cries.

Every minute of whimpering feels like an hour. My internal alarms go off and I anxiously go through my checklist. Are you hungry? Do you have to poop? Do you want to play?

So I do all these things. Still crying.

When I texted my friend to ask what they do, they calmly replied: “I don’t know, ignore it? He’s a big, furry baby, Dillan.”

So after making sure he’s good to go, I just go about my morning.

Eventually, he stops.

This made me think of our minds.

For seemingly no reason at all, our brains are in panic mode telling us something is wrong. We jump to solutions and distractions. Fix fix fix.

Only to prolong the alarms.

The practice of mindfulness doesn’t aim to stop negative thoughts. The goal is to simply be able to recognize negative thoughts as they inevitably appear.

So, “I’m never going to be financially stable” becomes “I’m having a stressful thought about not being able to pay my bills. I feel it in my chest and throat.”

This rarely makes the experience more fun, but it does look at it from an objective space.

I used to connect being tired with my life being shitty.

One night of bad sleep and I would spend my day thinking, I feel like garbage I have no motivation I am garbage the world sucks I suck.

Then one morning during a meditation, I was asked to focus on the physical sensations of being exhausted. I felt my heavy eyes and throbbing forehead. I watched the sentences and images of thoughts float by.

It was as if the clouds had parted.

“I suck” became “Oh, I’m just tired.”

Nothing’s wrong.

We can just let the dog cry for a bit and see what happens. Eventually, he’ll lay down and rest.

I went too far

A little girl wearing a mask and holding a teddy bear also wearing a mask

I like to create rules.

Boundaries and guidelines for living a healthy and principled life.

In the past couple of weeks, I’ve added two rules to my chart:

  1. I can only drink alcohol twice a month.
  2. I can’t give unsolicited advice.

I’ve changed my mind on both of these. Let me explain.

Let’s start with the second one: giving advice.

I recently read The Advice Trap: Be Humble, Stay Curious, and Change the Way You Lead Forever. (Here’s my review of the book if you want my quick summary.)

In short, giving advice isn’t always the best way to help someone. We usually provide solutions to the wrong problem and, while we don’t like to admit it, our solutions aren’t always that good.

I soaked this in. The last chapter is a reassurance that giving advice isn’t evil, it’s just not always the most effective option.

Despite this, I processed the whole thing as: I must never give advice.

So, when I inevitably did, I felt gross. I felt like a bad person who was hurting my friends and colleagues.

It didn’t take long for me to go, Yeah…I don’t think I’m supposed to feel this way.

As for my drinking, that rule came from puking two nights in a row while on vacation. Naturally, I woke up that second morning certain I would never drink again. I’m sure I’m the only person who has ever pretended to decide that.

But this weekend, I went to DC to have dinner at my friends’ apartment. They cooked a delicious meal and offered me a glass of wine.

I thought, You know what, I DO want one glass of wine. Maybe even two.

And that’s what happened. The three of us finished a bottle then drank water and played games for the remainder of the night.

I said out loud, “Ah. This isn’t the problem. Getting fucked up is the problem.”

Believe it or not, I just don’t enjoy getting wasted as much as I did when I was 20 years old. Go figure.

The next night, I got dinner at my other friends’ house and we each had one hard Kombucha (I know, we’re tanks). It turns out that when I only have one or two drinks I tend to not make shitty decisions.

Conclusion

I erased both of those rules from my whiteboard.

The lesson?

It’s a great thing to notice areas of improvement in our lives. We have the power to make changes in our habits and tendencies to create something better.

But it’s even more healthy to reassess those changes and course-correct if they’re not fully meeting our needs. We can ask: Is this really a problem? If so, is this the best way to address the problem?

Then when our needs shift we can adjust again. And so on.

I don’t really drink unless it’s a social event and I’m not rushing to preach my worldviews to people. But I will have a beer here and I’ll share some opinions there…

All I can do is try to be healthy and helpful and apologize when I overstep.

That’s the new rule.

The value of heartache

A woman holding a neon heart against her chest

Life can fucking hurt.

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.

Feel…but learn as you do so.

You are not your past

A giant analog clock on a wall made of stone

For 26 years, I had two limiting beliefs cemented in my mind.

  1. I could never run a business—I’m not business savvy and none of it is common sense to me.
  2. I’m a talker and a thinker, but when it comes down to it I never take action with the things I want to do.

Today, I work 20 hours a week, make more money than I ever have before, have my dream job…and it’s all from taking consistent action and creating my own company.

Okay, that all sounds like a fake entrepreneur’s Instagram ad. I promise I’m not about to pitch my ebook or online course.

My point is: In the last year, I’ve flipped those two “certainties” on their heads.

I created a sustainable business that pays for my life. And the thought of not taking action if I want something feels nauseating. When there’s something I’m interested in that I think would benefit my life, my first thought is: How can I make it work?

To be fair, none of this came from a simple mindset shift or from a single event. This has all been a slow-growing and consistent progression. (Plus several anxiety-riddled months.)

So what can we do with all this? Or did I just want to brag about my life? While it does feel nice (and a bit slimy), I wanted to highlight an unfortunate truth:

We create fixed identities for ourselves by using the past to define us.

We can hear it in our language.

• “I always…”
• “I never…”
• “I’m not the kind of person who…”
• “I tend to…”
• “I could never…”

As Steve Chandler says, we mistake habits as traits. Repetitions as characteristics. Because we’ve done something more than once in the past, it’s set in stone that we’ll keep doing it.

I truly “couldn’t” run a business or take consistent action. Until I could.

When we think we can’t do something, we tend to prove ourselves right by not putting in the effort to make it happen. If I’m certain I can’t write a book, I never sit down to start typing. Therefore, my hypothesis gets confirmed.

Many of us have heard the phrase: “People don’t change.”

What fucking nonsense.

People change all the time. Our values, our habits, our goals…The vast majority of us are experiencing a neverending evolution.

Personalities and tendencies are real, but we don’t have to let them pigeonhole us and keep us stuck in the same place.

I’m aware that this blog sounds like a typical self-help book. But if we just take consistent, scary action…we’d be amazed by the ways we prove ourselves wrong.

Why I never lie

A child with painted hands

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.

The effect?

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.

Conclusion

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.

Sweating my way to Canada (pt. 3)

My friends Dennika (left) and Anya (right)—Tofino, Vancouver Island.

If you haven’t read parts one and two of my journey to Vancouver Island, go do that first. It’ll help me sleep at night.

Today, I’ll wrap up the story and share the insights I gained from my 16-hour travel day.

Flight 2.5: Montreal to Toronto

After missing my first flight ever, I plopped down at the gate and waited for my new flight to Toronto. I had an hour and 15 minutes until it boarded, which felt like heroin.

It feels strange to write this now, but at that time I felt truly depressed. I felt it all in my face and chest. This was my deepest, darkest fear and it had actualized.

But over the course of that hour, I quickly calmed my nerves by meditating over two facts:

1) There was literally nothing else I could’ve done to avoid missing my flight.

I got unlucky. The delay. The jammed luggage door. The random COVID test.

Perhaps Usain Bolt would’ve caught up to the gate in time. But for me, there was no glaring instance of stupidity that kept me off that plane.

Shit just happens. Sometimes everything goes our way. Something it feels like the cards are stacked against us. Usually it’s something in between those two.

This stoic concept of what I can control vs. what I can’t arrived quickly to me. It’s a habit I’ve built over the years. But the second fact which took over my entire body was this.

2) My life is pretty damn good.

Let me explain.

I was sitting in that chair legitimately feeling the highest levels of anguish and heartache I’ve felt in years. After about 40 minutes of reflection, I thought, Holy shit dude. If THIS is what causes these emotions for you…that’s proof your life is amazing.

For most, what unravels these formidable feelings are things like…

• losing a loved one
• feeling lost in life
• having clinical depression

For me, it was adding five hours to my day and having to get on one extra plane as I headed to an unbelievably gorgeous island with unbelievably gorgeous people.

Some people really have it rough, eh?

A wave of light and gratitude swept over me. My sadness was gone. My frustration was gone. I got on my flight, joked around with the flight attendants, and headed to Toronto.

Flight 3: Toronto to Vancouver

We landed.

I got an A&W burger and a rootbeer float.

I called my friend and told her about my trail of tears.

We laughed.

The plane boarded and we took off for a five-hour flight to Vancouver.

Flight 4: Vancouver to Vancouver Island

There was another delay and for the second time that day, I was sure I would miss my next flight.

Please no…I’m so close.

I could see the island. The last flight would be 11 minutes long.

When we finally docked, most of us jogged off the plane. Just outside the gate, there was a man yelling, “To Vancouver Island?” My ears perked up.

“Yes sir,” I exclaimed.

“Right down there to C53,” he said confidently.

I put my hand on his cheek and said, “Thank you, my Guardian Angel.”

Well, I wanted to do that but I didn’t want to miss my flight. I followed his directions and speed-walked to C53.

I made it to the gate to find a young couple showing their boarding passes also out of breath. It was the last gate open in the entire airport. The plane was waiting for us because they knew several passengers were coming from my Toronto flight.

I walked directly up the steps to the tiny plane, sat in my seat, and texted my friend:

“It’s done. I’m on the last plane. Justin Trudeau can’t kill me. He forgot I bleed red white and blue.”

The flight took exactly 11 minutes. It was the most turbulence I’ve ever experienced on a plane. And I couldn’t have cared less.

We landed, I thanked the flight attendants profusely for waiting for us, and I walked out.

“Dillan,” I heard.

My friend was waiting outside the terminal for me. I dropped my luggage and melted into her arms.

This was my first time meeting her in real life. She was smaller than I pictured and smelled just as good as I had imagined.

I made it. My vacation could begin.

How this daily blog saved my life

A little boy with glasses reading a book

I was a fairly negative person until I was 23.

People did shitty things and it felt as though life was happening to me, not for me. I blamed others—or, even more vaguely, “society”—for my shortcomings.

It couldn’t have possibly been my lack of work ethic or my non-existent skills. No, clearly the universe was out to get me.

A big part of changing those thoughts was actually brought on by starting this blog.

For two and a half years, I’ve been typing my thoughts out every morning at this desk. The big fear I had when starting was that I would quickly run out of things to write about. I mean, a fresh blog every day? How interesting do I think my life is?

It turns out, our lives are quite fascinating…if we allow them to be. It’s a choice.

We can choose to go through our days as curious observers. I call this the Researcher Mindset. In other words:

Every single conversation, event, or mishap has value. There’s a lesson in everything. If there isn’t, that’s only because we’ve chosen not to look for it.

I’m not a “Everything happens for a reason” guy. I think things just happen…and we have the awesome power to derive meaning and wisdom from those things.

Let’s go through two examples—one small-stakes and one high-stakes.

1) A potential client says No to my business proposal.

No matter how smoothly the process goes up until the sales conversation, I have no control over how a person reacts when I say the dollar amount.

I’ve said a number and had people calmly say, “Oh, that’s it? Cool!” And I’ve said that same number and seen people baffled and think I’m joking.

People have ghosted me, dodged my messages because the money aspect scared them away, and flat-out asked to end communication with me. Needless to say, for a person running a business and trying to help people, this can be wildly frustrating.

In the early days, it was easy to take rejection personally. I would think…

How could they do this to me?
People suck.
• I can’t catch a break.

Shockingly, feeling that way and giving off that energy never made anyone change their mind and sign up with me. It just made it harder to be present and loving with the next person I was talking to.

So I began using my Researcher Mindset.

With every proposal conversation, I ask: What did I learn from this? What can I take away from this?

By asking these questions, I’ve improved as a business owner tremendously. People get back to me quicker, they’re more comfortable negotiating, and things are just clearer in the conversation overall.

2) My mom dies.

I’m well aware that my mother’s passing will be the worst day of my life.

But I actually don’t even have to wait for that day to use the lesson I’ll learn from it. Let me explain.

What I assume will smack me in the face will be the full understanding that no matter how much we care about a person, our time with them is limited. We will all fade.

The lesson here is simple. The only thing we can control is how much we cherish and utilize our time with these people while we have it.

When my mom invites me to something, I say yes. When she tells stories, I listen.

Conclusion

It can be hard at times, sometimes it may feel impossible.

But the most powerful question we can ask on a consistent basis is: How can I use this?

It’ll make us more resilient, more positive, and more appreciative.

it certainly has for me. Be a Researcher.

3 rules for disagreeing with someone

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.

Conclusion

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.”

-Mark Manson

I really don’t feel like writing this blog today

There are many days where even the thought of putting together a few sentences is exhausting.

But doing the things we care about doesn’t always mean we’re having a blast.

Most days, I don’t feel like:

• working out
• reaching out to prospective clients
• writing
• practicing/studying chess

But putting in those groggy hours makes the times I do feel like doing them so much easier and more rewarding.

If I can do this shit when I’d rather do anything else…then I can probably do anything.

Up since 5am

I woke up this morning to someone banging on my door. It was my downstairs neighbor.

He said there was a ton of water coming into his apartment from the ceiling. We inspected my water heater and the entire thing was flooding.

We unscrewed the wall unit and saw it was in fact coming from above. So I walked upstairs and did exactly what he did to me. I knocked on their door about ten times until an exhausted mother asked what I wanted. Rinse and repeat.

Her pipe had burst. We called the emergency number, she took down my phone number, and we laughed about our unique way to begin the Saturday.

In the past, this might’ve set me up for a shitty day. But right now, I’m just stoked I know two more of my neighbors. Plus Hank got an earlier and longer walk this morning.

And seeing the sunrise in its entirety wasn’t bad either…Today is a good day.

Dammit, our parents were right

Parents helping their daughter learn to ride a bike

I’m almost the same age my mom was when she had me.

As my friends and I approach the ripe age of 30, I’m realizing more and more that the cliches of getting older are cliches for a reason.

There are the funnier ones, like:

• hangovers get worse
• it’s easier to build fat
• we enjoy quiet alone time more

But in this blog, I’d like to briefly discuss a recent shift in my perspective. Let me explain.

Until now, I’ve relished a fairly obligation-free life. I’ve been single most years. I have no kids or pets. I’ve never owned any real estate.

But something struck me the other day as I was laying on the couch with Hank—my friends’ dog I’m pet-sitting.

Hank the dog laying on the couch
Sorry for the crouch-shot.

I’ve spent the last two weeks walking, feeding, and playing with this other living creature. Here’s what I’ve realized.

We may begrudge adding more responsibility to our plates, but it makes our lives more fulfilling and purposeful.

When I wake up at 6:30 and can’t see straight, I hear a rhythmic thumping as Hank’s tail wags and slams against my wall. It doesn’t matter how many times we do it; he’s elated to get up, eat breakfast, and go for a stroll around my apartment complex.

Every morning.

If that doesn’t motivate someone to get their day started I don’t know what would.

Parents might roll their eyes reading this. I’m aware I’m just watching a dog here.

But this is my first true experience of another living being depending on me to survive and live an enjoyable life. It’s been a real jolt of energy to add some responsibility to my life.

One of my best friends, for example, just had a baby. Even being ‘Crazy Uncle Dill’ has added some meaning to my days.

Her first words were: “Dillan is hilarious.”

I’m not saying I’m trying to have kids tomorrow. I’m saying I’ll remember this as a pivotal mindset shift as I become…dare I say it…an adult.

Simple lesson (pt. 1)

A simple lesson I learned this year:

Rejection is always good news. It’s the best possible proof to show this isn’t a good fit right now.

The simplest cliche to change my life

Leaves changing red in the fall

I tried to kill myself in 2017.

That summer was a crescendo of 23 years of me having no defined values, no direction, and no true skills.

I would talk and think endlessly of all the things that could be…while at the same time ignoring my way through life. I wasn’t getting any actual work done.

After a handful of pills and a fifth of Jim Beam, I woke up two days later with both staggering fog and utter clarity. “This has to change,” I mumbled.

But what I quickly came to realize was that that desire was backward. I had been waiting my whole life for this to change. And waiting around hadn’t gotten me far. So I turned to what is now my favorite cliche…

If we want something to change, we have to change.

It’s so stupidly simple. But what I’ve seen in a lot of folks—including myself—is a longing for transformation while living with the same habits, routines, and thought patterns as the month before.

The change starts with us. There’s nothing out there that’s going to make it happen for us.

Do you really want this?

A man shooting a scene with a camera

We often think we want things that don’t actually fill us up.

We may desire to:

• run a thriving business
• read a book every week
• be in impeccable shape

But there’s a lingering question in all this…

Do we actually want to do what it takes to do this, or do we merely enjoy the idea of it?

I thought I wanted to be a full-time YouTuber, so last year I did a daily vlog for two months. I burned out hard and realized I fucking hated it. This felt crushing because I would watch Casey Neistat’s videos and feel like I didn’t have enough grit or determination to achieve what he has.

Comparison aside, I had to come to grips. I wanted the result but resisted the work needed to get the result.

What I wanted:

• millions of subscribers
• a community
• ad revenue

What I didn’t want:

• to shoot scenes
• to be “on” all the time
• to edit for hours each day

So what does this mean? How can we look forward to the boring and mundane stuff?

I love running a coaching business, playing chess, and working out. Even when I don’t.

It’s okay to not like the things we think we like. We just have to find the work we like.

3 questions when I’m in a rut

1) How am I complicit in creating discomfort in my life?

2) How can I take ownership over what my life looks like?

3) How is this making me stronger?

I’ve written this affirmation every day in 2021

A blank sheet of paper next to a cup of coffee

I started dabbling with affirmations last year. I thought they were total bullshit.

I’ve never been into the idea of manifestation or the law of attraction. Naturally, we should have a clear vision of what we want…but the only way to make it happen is to consistently do the work and actions necessary.

We don’t manifest a healthy body. We exercise and eat well to create one.

We don’t manifest more money. We provide more value and change our financial habits to create more money.

We don’t manifest better skills. We practice until we get really fucking good at them.

….BUT affirmations don’t have to be about wanting something from nothing.

On New Years Day, I decided that my life would have a new mantra. I wrote it down in my notebook and have continued to write it every day since:

“I love doing scary things.”

Has this turned me into a fearless and rich person? Absolutely not. But, whenever opportunities or risky ventures have presented themselves to me this year, I’ve simply reminded myself that I love doing scary things.

I’ve never taken more intimidating (to me) action in my life than in the past eight months. I’ve…

• started a freelancing business
• halted that freelancing business to go full-time with my coaching business
• paid $12,000 for coaching programs
• put myself out there as a coach to a bunch of people from my past—getting ignored and rejected constantly
• started running group coaching calls/workshops
• bought plane tickets I couldn’t afford
• did a triathlon
• wrote this blog every day and shared my favorite ones
• told a woman I had feelings for her
• started writing a book
• built an established business when, my whole life, I’ve said I know nothing about business

What I’ve learned from this:

  1. Affirmations aren’t bullshit if we use them to guide our mindset toward taking more action. Simply writing things that sound powerful isn’t enough, but if we do something about it, those words can change our lives.
  2. We don’t have to be fearless; we have to be courageous. Fear is natural, but we must not let it stop us from creating the life we want to live.

Are we allowed to feel bad?

A toddler playing with their stuffed dinosaurs.
Me and my thoughts yesterday.

I had a really shitty day yesterday.

After showering and getting dressed for my three back-to-back coaching sessions in the morning, I sat down in my office. Of the three calls scheduled, one canceled last minute, and two didn’t show up at all. 0/3.

Sometimes I welcome a canceled call for the extra free time. But three in three hours took an enormous mental toll.

Waves of financial anxiety and doubts of self-worth came rushing in. I even made a Twitch account out of spite. I mumbled: “Stupid coaching. I’ll just be a streamer. Coaching is stupid anyway…”

Whenever this happens it feels like two entities are competing with one another: Logic and Emotions.

Logic was telling me:

This is not even close to the end of the world.
• Lots of people in lots of places have it WAY worse than you do right now.

• Why are reacting this way?
• People would kill to have your problems.

But despite all this, my Emotions kept rubbuting:

• This fucking sucks and I’m sad.

I felt it in my eyes and face. It was like my vision was slowing down.

Luckily, I had a fourth session scheduled in the afternoon. My goal was to not bring any of my energy from the day into our conversation.

We did our session and it was amazing. He had incredible insights, he made me laugh, and we had a lovely deep dive into his thoughts and fears.

Only after we finished did I tell him about my day. He said he could tell something was up simply from my body language when we hopped on the Zoom. I thanked him for his time and for making my day better.

In the evening, two of my best friends invited me over for dinner. I was a bit nervous because I was doubting my ability to have a clear and present conversation.

On top of that, one of the friend’s dads just had a funeral. How could I deserve to complain about my day when she just buried her father?

It’s not a competition

We swapped stories and it was bittersweet to hear her discuss the anxiety and closure-filled week. When she asked about how I was doing I figured I’d just be candid and open up.

They both listened to every word I said and showed nothing but love and support.

When I admitted it was weird to talk about my “problems” knowing they had just gone to her dad’s funeral, she immediately responded: “It’s not something to compare.”

Really good peoples.

We drank wine and played with their dog and my grey day drifted off like storm clouds. The tension in my eyes was gone. I just felt grateful.

Lessons

1) It’s possible to both a) acknowledge our good fortune and b) feel sad…at the same time.

2) One of the most important things to have in life is friends to whom we can open up wholeheartedly without being judged or scorned.

3) We will never arrive at a day where we’re completely safe from shitty things or negative emotions. We can only improve our skills in handling them and ask the people around us for help.

4) I’m going to be a professional streamer.

5) Lol jk.

Why you don’t need confidence

A confident woman looking in the mirror

I coached a fellow coach yesterday who said she wanted to leave the session with enough confidence to do x, y, and of course…z.

We started exploring.

What’s your definition of confidence? What does it look/sound/feel like?

When in your life have you been truly confident?

How much confidence have you decided you need before you can take action? On a scale from 1 to 10?

She told me about her career as a teacher. She studied education for seven years and then jumped into teaching kids, year after year after year. She said when she stood up and taught a classroom she knew who she was and what she was doing.

I reflected back: “It sounds like you gained tremendous confidence after learning and practicing something for many years…And now you’d like that same level of confidence with something you’ve only just started.”

We explored further.

She explained that as a teacher, she could provide the answers, but as coaches our job isn’t to give away solutions but to help others discover the solutions they already have access to.

She had an insight: “When I’m coaching, I’m not the teacher. Life is the teacher. I’m just supposed to be with them in that space where they can learn their own lessons.”

“Holy fuck,” I said. “That’s awesome!”

When I asked her what her biggest takeaway was, she responded without pause: “I don’t need to worry about confidence. I need to focus on authenticity. I’ll show up as me and practice until I get really good at everything I want to do. The confidence will come.”

Sheeeeesh. I wanted to her hug through my laptop screen.

This was such a lovely example of overcoming one of the most powerful stories we tell ourselves: I need more confidence so that I can…

Don’t get me wrong, confidence is amazing. The flow that comes from a belief in oneself can be euphoric. But it’s not a prerequisite for taking action, it’s a byproduct.

Natural talent is fun, but most of our confidence comes from doing something a lot and getting better at it. When we think we need more confidence what we really need is more practice.

Just jump in. The confidence will come.

Good

A man climbing up a steep rock

One of the most popular personal development cliches is to embrace failure. Fail forward. Fail over and over again so we may improve our skills.

On a recent phone call with my friend and business mentor, we discussed the vitality of challenges. He brought up Jocko Willink’s famous concept: ‘Good.’

My friend and his team recently underwent a huge transition in their business, with him taking on a bigger leadership position. He was telling me about the newest obstacles on his plate: maneuvering the varying values among teammates, finding the best practices for communication, and finding bigger and better clients.

As he laid all this out I couldn’t help but think: Good for you.

As I told him this, I explained that he’s becoming a wildly better leader. He’s experiencing stress tests. No one improves by doing the same thing every day and never being challenged.

I tell the same thing to my fellow coaches all the time.

Many coaches hesitate to take action because they’re afraid of looking dumb, having an awkward conversation or encounter, or not coaching well. I’ve experienced all of these and it sucked every time.

But it was after blunders like these where I felt the most growth in my skills as a coach and as a business owner.

People think they should get better before taking action so they make fewer mistakes. That’s backwards. We must first take action and make a ton of mistakes, for that’s the only way to get better.

The next time something challenging comes up in our lives, we can sit back and think, Good.

How long does it take to build a habit?

A woman building the habit of flossing her teeth

Every month or so, I watch a video of James Clear talking about habits. Here’s the one I watched yesterday.

It’s always a refreshing realignment. His explanations are scientific, actionable, and best of all…simple. His book Atomic Habits is one I feel everyone should read.

Be it from his book, his blog, or his interviews, here are the big things I need to remind myself each month:

1) The quality of our habits tells us everything about our lives.

The number in our bank account is the sum total of our financial habits. The way our bodies look and feel is the sum total of our diet and exercise habits. The state of our living space is the sum total of our cleanliness habits.

We don’t need to “clean our room”; we need good cleanliness habits and then our rooms will always be clean.

2) We repeat what we enjoy.

Discipline and willpower will only get us so far…and most of the time they don’t get us far at all.

This is why the failure rate of fad diets is so high. Torturing ourselves into being healthy is wildly unsustainable. Statistically, the best results come from tiny, progressive changes in our daily habits.

Short exercises. Eating fewer processed foods. Drinking a glass of water.

None of these sound glamorous. That’s because they’re not. What sounds sexy (and I see this in coaching sessions all the time) is throwing five new habits on our plate at once.

“I’m gonna…”

• do an hour-long workout five times a week.
• finish four books this month.
• wake up at 5am on weekdays.

The same thing happens every time. The person, fueled by motivation, crushes the first day or two. But then when they return to their normal state, they remember they don’t enjoy the work needed to sustain any of these systems. They went from 0 to 1000 and gassed out. They ran a marathon without training for it.

It doesn’t sound as cool but the effective approach would be: “I’m gonna…”

• work out for five minutes before I shower.
• read at least two pages each morning.
• wake up five minutes earlier each morning.

It’s the unsexy, incremental changes which move us toward the person we want to be. But those changes have to be easy and enjoyable.

3) It takes forever to build a habit.

I don’t mean: Ugh, this is going to take forevvverrr.

In the personal development world, we often hear numbers thrown around for how long it takes our brains to feel something as habitual. I’ve heard 21, 66, and 100 days.

These are all averages so there’s no guarantee how long anything will take for anyone. It could happen this week or in eight months.

The truth is, building a habit takes a lifetime. If we stop doing the thing for any reason then we’ll have to start over.

I’ve been doing the same morning routine for almost four years now. There have been plenty of weeks where I’ve strayed or neglected to do parts of it. And each time, I have to slowly build it back into my ritual.

As James says, when people ask how long it takes to build a habit, what they’re really asking is, “How long do I have to work?” In other words, How long until I can just go on autopilot?

But our autopilot capabilities will always be tested, no matter how deeply ingrained the habit is. Changes in schedule, priorities, interests…Anything can throw us off course.

It’s up to us to steer ourselves back toward where we want to go.

Am I getting worse at chess?

A woman playing chess and holding up the king

The other day I was playing chess against a friend.

The week before, I had beaten him three times in a row. Naturally, I concluded that I would ride that momentum forever and never lose to him again.

When we played next, he beat me three times in a row. I considered quitting chess altogether…

Jokes aside, I must admit there was an emotional toll those three losses took on me. My thoughts were:

• Have I gotten worse?
• How has he gotten so much better?
• What did I do right last week that I didn’t do this week?

Then I heard about a psychological experiment that was conducted in the Air Force. They wanted to prove which method of feedback was more effective in impacting an officer’s performance—positive reinforcement or negative reinforcement.

Generals boasted as they pointed to clear evidence that punishing pilots for mistakes almost always led to improvements on their following flight. Likewise, praise tended to lead to worse results on their next go.

But there was a glaring issue with their testing.

When they were challenged to create a control group, they found that no matter what, soldiers who did super well one week tended to do worse the next week…and soldiers who did super shitty one week tended to do much better the next.

This highlights a popular statistical phenomenon: Regression to the Mean.

Basically in everything we do, there’s a natural variation—ups and downs, push and pull, give and take.

If we have an amazing week at work, things will likely even out the following week to bring us closer to our average. But it’ll feel like we’re regressing.

The same is true for any skill or activity—chess, business, exercise…

As of writing this, my ELO (number rating) in chess is 1420. Sometimes I play like a 1600 and sometimes I play like a 1200…but 1420 is about my average.

Nothing guarantees absolute consistency. In other words, sometimes we’re awesome, sometimes we suck, and both are fine. The more we do something, the more we move toward whatever our average is. When we’re on a low, it doesn’t mean we’re getting worse…and it probably means we’re about to experience a high.

The goal is to improve our mean so we can experience higher highs.

Effortless

I just finished reading Effortless: Make It Easier to Do What Matters Most by Greg McKeown.

It was the perfect sequel to the book that changed my life last year: Essentialism—The Disciplined Pursuit of Less.

This book challenges the notion that anything important or valuable has to be hard work.

Hard work is lovely, but it’s wildly beneficial to us if we stop and ask: “What would it look like if this were easy?”

I’m a slow reader…and I flew through this in two days because I enjoyed it so much.

My biggest takeaways:

• Burnout is not a badge of honor.

• The more you complain, the more you have to complain about. The more grateful you are, the more you have to be grateful for.

• When you focus on what you lack, you lose what you have. When you focus on what you have, you get what you lack.

• Establish clear conditions for what ‘done’ means, then stop.

• There is no mastery without making mistakes. And there is no learning without the courage to be rubbish.

What you need to be successful

A successful person on top of a mountain
Not me.

I heard a quasi-debate the other day between friends.

The question at play: What leads to a person’s success—hard work…or luck?

On one end, we can be given all the best tools and resources necessary to live amazing lives; but if we don’t take action and actually use those tools…nothing will happen.

We need to do the work.

On the other end, we don’t choose anything about ourselves: to be born, who our parents are, where we’re born, our brain makeup, etc. If we grow up in a neighborhood where education isn’t available and drugs and violence are rampant…it would be almost impossible to develop an “I’ll just work my ass off” mentality.

We need to be lucky.

The Growth Mindset—the belief that we can improve in anything with enough time and effort put into it—is real. But it’s only real if a person believes it’s real. Hence the word mindset.

And a person can only believe it’s real if they have the luck and means to—e.g. a community which challenges them, an inner ability to pursue things, or access to the internet or to books.

As with almost every debate, my stance is that two things can exist at the same time. In order to be successful we must put in the work consistently…and we have to be lucky.