Core principles

Every individual or business should run on a small set of core principles.

I just updated mine:

1) Curiosity before solutions.
2) Make people feel loved and heard.
3) Serve; don’t please.
4) Do the things I love all the time and get better at them.
5) Take nothing personally.

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.

No one cares where I went to school

Two students sitting down on the grass at university while doing their homework

In early 2020, I wrote a shitty blog ranting about college.

I still hold all the same opinions. But today I’d like to briefly discuss one aspect.

The fact that I run a profitable business that sustains my life and fulfills me at the highest level. I help people create the lives they want, get organized, and even grow their own businesses.

And in the last four years, not a single person has asked if I went to school.

Not where I went to school. If.

I’m not saying any of this to brag. I’m a college dropout who spent most of those four years living with his mom because he couldn’t afford anything else. (To which I’m incredibly grateful. Thanks, mom!)

The point is this.

In the past, people cared about where we got our credentials. Today, most people just want to know if we’re useful.

“Where did you graduate?” is now “Can you help us?”

I have friends making six figures because they taught themselves how to code. I know folks with great jobs because they’re great people who learn well and have strong interpersonal skills. I do well because I’ve developed the skill of coaching and curiosity.

All of which is possible without paying $80,000.

The caveat here is that of course there are professions where schooling is entirely necessary. I don’t want a surgeon who taught herself how to cut people open.

I don’t think college is a bad idea. It’s just not the only idea. There are many other ways to do interesting things and make money.

Many companies would ask me: What are your credentials?
“Alcoholism,” I would say. “Bankruptcy and divorce.”

Steve Chandler

Fuck Off Day

A woman waving goodbye to her toddler son as he runs out with his backpack

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.

People:

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.

Environments:

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.

All because I took some time away from them.

Activities:

I love chess.

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.

TL; DR:

Intentional time away from the people and things we love strengthens our relationships with them.

THINGS I’m grateful for

Luigi, Yoshi, and Mario standing next to one another

Yesterday, on the CREATE Program calls, we talked about expressing gratitude.

We separated the things we’re grateful for and the people we’re grateful for.

One woman laughed because of how hard it was to not go straight to the people in our lives. It felt counterintuitive. There’s usually a negative connotation in focusing on the stuff we have instead of the relationships we enjoy.

But my prompt was this:

What are the things—both tangible and intangible—you are so incredibly grateful to have in your life?

Awesome answers included:

• “My sobriety”
• “How much time I have left on Earth”
• “My past—for all its valuable lessons”
• “Having a computer which connects me to so many people”
• “My growth”

It was difficult to have this conversation without a big dumb smile on my face.

Here’s my answer to the question:

I’m grateful for the infinitely small probability of getting the life I have.

I didn’t choose my parents or my environment. Which means I didn’t choose to not be a Syrian refugee. I didn’t choose to not have a shitty mom. I popped out in a hospital in Virginia Beach in 1994 and they happened to hand me back to two capable, loving adults. Then those adults raised me in middle-class America.

That’s some good shit.

There are so many factors that could’ve drastically altered my life. A few strands of DNA. One of my best friends not attending my high school. A childhood injury.

But so far, everything has happened how it happened and I look how I look and live how I live.

I’m grateful for the brain I was born with. It has given me the skills to connect with others and create a lovely life for myself. It allows me to read and write every day. It keeps me from being mean to people.

Tomorrow, I’ll talk about the people I’m grateful for. Stay tuned.

(**If you would like to join wholesome conversations like this one, ask me about the CREATE Program!)

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.

My 10 Commandments

The front lawn of a courthouse

I’m not the least bit religious, but I do advocate for living a principled and value-driven life.

Here are my 10 Commandments.

Thou shalt…

  1. Pursue a Growth Mindset—seeing everything as a lesson and a chance to improve.
  2. Never be uncomfortable with your shirt off—remaining fit and active.
  3. Treat every human being with the same amount of humor and respect—be they a CEO or a gardner.
  4. Pick your battles, but be confident when expressing your ideas and opinions.
  5. Cherish every minute of quality time you get with close friends and family.
  6. Never order food or watch a show unless with another person.
  7. Never take anything personally—especially rejection.
  8. Go to the gym at least three times per week.
  9. Never text while driving a car—even at a red light.
  10. Spend more time in a day reading or having a conversation than staring at a screen.

Being human, I don’t stick to these perfectly. But having these guidelines has moved me drastically closer to the person I aim to be.

What are your commandments?

I asked my doctor friends about vaccines

Three doctors looking at

This is NOT a post trying to convince someone to get vaccinated. It’s a blog about humility.

How it started

A few months ago, I had a warm debate with a friend about the COVID vaccine. I found her arguments to be shaky and without much reassuring evidence to support them.

But it wasn’t what we were arguing about that struck me. It was the level of certainty she had about her opinions while clearly being nothing close to an expert herself.

Certainty that the counter-evidence was likely bullshit. Certainty that the 1% of medical doctors against vaccines are in the right. Certainty that the virus is being propped up so the government and big pharma may gain control over citizens.

In general, I’m less interested in what a person thinks and care way more about how they think.

The conversation with my friend eventually fizzled out, but I couldn’t help but think: Have you had this debate with any real medical experts?

This was my first dose of humility…because I hadn’t spoken to anyone in that field either. So I decided to change that.

I’m lucky to have friends and folks in my life who are either medical doctors or are surrounded by them. I reached out to each of them and asked for their expert opinions in a neutral way.

I didn’t state my thoughts and then ask for validation. I simply said: “I’m trying to get a clearer picture here. As a medical professional, would you be willing to share your thoughts on the COVID vaccine?”

Every single doctor I reached out to sent me paragraphs in response.

Here are the notable takeaways:

• “I’m extremely confident in my ability to read and dissect medical literature surrounding this topic. I think a lot of people who “do their own research” don’t know the first thing about how to conduct, analyze, or determine the relevancy of medical studies. A Google search is not even remotely the same thing.”

• “One of the reasons mankind is still alive is the existence of vaccines. Polio, Measles, Mumps, Varicella, Meningitis, Influenza, and more…would ravage us if we didn’t have vaccines. I think people have become more skeptical in the world today compared to 20 years ago about nearly everything and essentially with this first new vaccine coming in that time, it’s a perfect target for controversy.”

• “As far as reasons I support it? It’s literally the answer to this problem we are all dealing with. It is safe, it’s well researched, the studies are all massively in favor of it, and it’s the fastest and likely the only way to go back to our normal lives.”

• “After these years of education and practical training, I think vaccines are one those things that have received unnecessary negativity towards.”

• “I know there are people who can’t get it, and that is okay. I also know that people who chose not to get it aren’t necessarily selfish people, they are normally just extremely uninformed or misinformed. Everybody acts in a way that they think is best. But just because you think you’re right, doesn’t mean you are. And in this case, it is causing harm to other people. It’s everyone else’s job to protect those of us who are more vulnerable. It’s part of our societal duties.”

• “I understand people want to be wary about side effects which is absolutely fine, but everything we do in medicine is evidence-based practice. We all take the Hippocratic Oath and essentially we try to do no harm while doing what is right for patients.”

• “I would understand the resistance to the vaccine if there was legitimate cause for concern, but there isn’t. Every single time I see a new BS conspiracy theory pop up, I take a week or two to look at the research and listen to the various experts that I know personally or follow on various forms of media. Without fail, every concern has been comprehensively debunked.”

• “It baffles and frustrates me that people are so resistant to entertaining the possibility that they may be wrong. It’s led to so much vaccine resistance and done so much harm. It’s the reason we are still in this mess, the reason the delta variant is such a problem, and the reason so many people are dying unnecessarily.”

What to do with all this?

To be clear, if any of these doctors said something like: “I actually warn people against the vaccine because of x, y, and z…” I would’ve included that too.

These just happen to be all the major points made by the five people I reached out to. I’m also aware that five people isn’t a great sample size.

The point of all of this is highlighted in the first takeaway I listed: I don’t have the slightest clue of how to read and dissect medical studies. Likewise, my friends who think they can in a matter of minutes seem foolish to me.

I think in the world of the internet—where we can find anyone articulating any opinion—it behooves us to practice more humility.

When did experts become morons? Corruption is real and people make mistakes, yes. But what allows someone to feel certain they know more than someone who’s been studying that thing for decades?

We’re experiencing a strange death of expertise.

Which makes me eternally grateful to have people in my life I can turn to who know way more than I do.

If I were thinking of getting spinal surgery, and I had a friend—who’s a server in a restaurant, say—tell me they actually did some research and thought I shouldn’t because it could damage my vertebrae…my response would be: “What the fuck do you know about spinal surgery??”

Vaccines and spinal surgeries are obviously different things in scope and scale. But what I’m trying to hammer home is the ridiculous nature of listening to people who certainly don’t know what they’re talking about.

This goes for my friends who are for the vaccines as well.

In summary:

1) I don’t know shit. Neither do most of us…so we should turn to the people who do know shit before cementing our own ideas.

2) Skepticism is healthy, but the point of expertise is to have people we can trust to take care of the wildly complex things which keep our lives going.

3) The next time we feel certain about an opinion, we must ask: How much time have I spent challenging this opinion? Who can I talk to in order to challenge these thoughts?

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

Talk to your friends

Two friends laughing together while sitting on a bench

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.

I’ve had…

• 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.

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. 3)

A simple lesson I learned this year:

It’s lovely to craft a successful career for ourselves. But what is twenty times more important is sustaining fulfilling relationships with other people—friends, family, and colleagues.

Is people-pleasing so bad? (pt. 1)

A young couple looking at menus in a restaurant

Two weeks ago, I ran a workshop on people-pleasing, saying No, and protecting our time and energy.

It was lovely to hear a group of friends, family, and colleagues collaborate and share stories and ideas.

The underlying notion of the conversation was that people-pleasing is bad and should be avoided. But then one of my coaching friends posed a challenge.

“I think people-pleasing gets a bad rep,” she said. “Sometimes it’s totally justified to do something we don’t feel like doing for the benefit of ourselves and especially others.”

I needed to hear this.

In the self-improvement and entrepreneurship worlds, it’s normal to hear things like:

If it’s not a Hell Yes, it’s a No.
No is a complete sentence.
Say No to most things.

What I realized as my friend was sharing her thoughts was that all these ideas are contextual. If we’re running a business, these rules are quite helpful. We can’t say Yes to every opportunity. We’d get distracted and pulled in too many directions.

But part of having healthy and fruitful relationships is being selfless for those we care about. Again, my friend made an excellent point:

“If you say No to five invites in a row, don’t get upset when your friends stop inviting you to things. Plus, how many times have you gone to something you didn’t want to go to…and you ended up having a lovely time?”

I love when I have my mind changed. Since this discussion, I’ve been more cognizant of saying Yes to things which would bring me closer to people…without burning myself out.

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.

All good, dog

Yesterday was strange.

One canceled session, two no-call no-shows, and a ton of dead time. I don’t do well with dead time.

I rarely have even one call in a day that doesn’t happen. Yesterday there were three.

As uneventful as the day was, it was mentally draining. Fears and doubts about my ability as a leader came creeping in.

But then something happened which made me forget about all of that.

My best friend dropped off his dog so I could watch him for the weekend.

Hank the dog playing at the park

Life ain’t so bad.

30 more visits with Grandpa

A grandpa smiling while sitting on a couch
Not my Grandpa lol.

Vacay

I went on a lovely family vacation this past weekend. Lakehouse, swimming, tubing, laughing.

But the most memorable moment came when I walked down to the boathouse to find my Grandpa standing at the bottom of the walkway. It looked like he was mentally preparing himself to ascend a mountain.

He had just gotten a pacemaker put in days before. I asked him what was up.

He told me he gets out of breath easily and so I held out my hand to help him up the steps. Once we made it up the first section, he thanked me and assured me he could take it from there.

“All good Gramps,” I responded. “We’ll go up together.”

We got to the deck and he took it from there since he had the handrails to balance himself. I walked back down to the dock to grab the beer I wanted and I noticed I was crying.

It wasn’t a sob. My mouth wasn’t moving. But tears streamed out of both eyes.

This was the first time I got a ‘slap in the face’ reminder of the universal truth: Our time is limited here.

A new lens

After that happened, I saw my Grandpa in a different light. I already love talking to him. He’s hilarious and one of the cleverest men I’ve ever known.

But for the rest of the weekend, I didn’t just enjoy my talks with him…I cherished them.

Every joke and story he told, I found myself uncontrollably beaming. I also looked at my calendar to find the best weekends in the coming months to drive down and visit him and my Grandma.

On top of that, I did some math.

My Grandpa turned 80 this year. Assuming he lives to be 90 years old, I have 10 more years left with him. But that’s incorrect.

On average, I see my Grandparents three times per year. Maintaining that trajectory, I don’t have 10 years left with my Grandfather…I have 30 more visits.

After this weekend, I can check off one of those boxes. 29 to go.

Is this depressing?

No. Not to me.

Talking about this shit is sad, yes. But I much prefer to be open and candid about the inevitable, rather than bury my head in the sand and pretend like death doesn’t exist.

I know people who do the latter and they tend to be the ones who shut down when the worst occurs. Not productive.

Understanding that we’re all approaching death isn’t morbid. It’s empowering.

It forces us to desire more presentness, listening, and compassion.

It invites us to say “Yes” to the things that matter more often: trips with friends, phone calls with family, playtime with kids or pets.

We can obsess over the number of checkboxes we have left with the people we love…or we can focus on the quality of each of those boxes before we check them off.

Having people we love who are alive is a gift. We get to call them, laugh with them, disagree with them, hug them, learn from them…

Even with someone we don’t particularly like—if we found out they had a month to live, we’d forgive their faults and forget our grievances with them. We’d hear what they had to say and make sure they were comfortable and cared for.

What if we did that more often with more people?

Conclusion

It’s up to us to enjoy the box we’re currently checking.

I’m not dreading the number of boxes I have left with my Grandpa. I’m ecstatic for the next box I get with him in a few months.

3 days of little tips (pt. 3)

Ask each of your close friends—or the people who know you best—what they think you’re biggest strengths and blind spots are.

What can I do more of? What can I do less of?

The more people you ask, the more you can put together patterns and work on things. Plus, you’re guaranteed to hear things you never thought you would hear.

How I maintain my energy

A pile of double A batteries

On a coaching mastermind call yesterday, we discussed ways we stay energized.

For me, it’s three things.

1) When I’m in a rut, I check my health trifecta.

• Am I getting at least seven hours of sleep each night?
• Am I eating a lot of processed foods and sugar?
• Have I exercised at least three times this week?

2) I take one weekend off each month.

I happily work on weekends since that’s when many of my clients are available. But once a month, I take a long week or weekend off to travel somewhere (usually on the east coast).

It’s a refreshing break after three weeks of hard work and I always return home feeling amped to get back to my routine and do it all over again.

Since I have no kids or other major responsibilities at this time, I figure I should take advantage of it while I can.

3) I spend a lot of time doing things I enjoy.

Chess, martial arts, exercise, quality time with friends, reading…

I find it vital to our souls to spend a good amount of time away from anything having to do with work or money. Like a vacation, it makes us appreciate our time back even more.

We should all have a thing. Preferably something challenging—a skill or a craft—we can practice and get better at.

For me, these three things are perfect substitutes for any drug or stimulant.

Marry pt. 2

The wedding I went to this weekend was amazing.

I saw old friends I haven’t seen in years, got all dressed up (something I love to do), and danced the night away.

I also:

• DoorDashed $60 of McDonald’s at 1am and fell asleep before it arrived.
• Laughed until I cried as my friend crawled (literally) into the room the morning after.
• Am pumped for the five weddings I’m attending in 2022.
• Feel eternally grateful for staying in people’s lives.

Fun fun fun.

Dance if need be

Sometimes, the best thing we can do for ourselves is put on our favorite album and pace around our home.

Mouth along with the songs. Dance if need be.

Start the day right.

Fulfillment formula

A woman in front of a chalkboard with formulas written on it

Here’s an overly-simple formula to ensure a level of fulfillment in our lives:

Step 1: Find something we like to do that’s difficult

Step 2: Do it all the time

Step 3: Get better at it

Step 4: Repeat steps 2 and 3

Be it an instrument, a sport, or a craft…having an activity we look forward to or something that challenges us is crucial—especially if it has nothing to do with our work.

When it comes to this, I’ve found that “Find your passion” is shitty advice.

Every now and then, someone finds something they are obsessed with immediately and that’s lovely. But for the other 99% of us, passions are developed…not found. They are grown like a plant, not discovered like pirate’s treasure.

In his book So Good They Can’t Ignore You, Cal Newport proves that the number one factor in how passionate a person is with something is their amount of experience/skill level in it.

We’ve all felt this. As we get better at something, we have more freedom to play around and do cooler shit, which tends to make us enjoy it more.

I’ve felt this with soccer, chess, tennis, jiujitsu, and writing.

Not that I’m particularly good at any of these things…but I have gotten better at them and have subsequently felt an increase in how much I enjoy doing them.

What do you like doing? What would you love to do consistently until you get pretty damn good at it?

Some days are perfect

It’s 10pm as I’m writing this.

Today, I cried tears of joy while driving home.

I got breakfast and mimosas with one of my best friends and his fiancé. I haven’t seen them in months since they’ve been up north preparing to have a baby. Today, I met that fucking baby, held her, and reached enlightenment.

Then I met my other friend to see a movie—The Green Knight—in theaters for the first time since the pandemic began. We rode scooters back to his apartment in perfect weather.

I drove straight to my mom’s house to take care of her dogs—walk, feed, and play with them.

Finally, I met up with another best friend to play chess, go out on his boat, and grab dinner. Leaving the dock, I looked back at the pink-sky sunset over the water and couldn’t believe this all happened in less than 12 hours.

I write about the lessons, struggles, and questions I explore on a daily basis. But sometimes I just need to sit back and reflect on how fucking grateful I am to have the life that I do.

My friends, my environment, my capabilities…

I’m not sure if I deserve them, but I certainly try to.

I think I like today. I think it’s good.

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.

Laughing on a boat

A couple laughing on a boat
A better-looking, more muscular version of me.

I took most of this weekend off to spend time with friends.

We had a shrimp boil, played corn hole, and drank Coors Light on a boat. Simple living.

It was one of those weekends where you find yourself belly-laughing every five minutes or so.

Being on the water. Telling jokes and stories. Discussing ideas about life.

I’m not a religious man. I don’t really believe in purpose or destiny…

But I dare say that’s what life is all about.

Letting go

I had a lovely coaching session with a client this past weekend where he let something go after seven years.

He had been writing songs since he got out of college and they have been unfinished all this time. The challenge is, his music tastes have changed a ton so he doesn’t feel inclined to go and finish the songs he started years ago.

By talking it out, he decided to let those songs go and archive them.

“I’m not going to finish them and there’s a reason why.”

He decluttered his life. He made space for more time and bandwidth.

What can you let go of to do the same?

Losing power

For the first time in my adult life, we lost power at my place.

We lit candles and reminisced over the good days when we could sit on our phones with the lights on. Instead, we had to sit on our phones with the lights off.

It got me thinking…what else do we constantly have at our disposal that we totally take for granted? It didn’t take me long to realize the answer: everything.

The fact that I…

• can see and hear
• have all four of my limbs
• don’t have any major disease
• have friends
• have parents and grandparents who are alive

The list could literally go on forever.

One day, these things will be taken from me. The only thing I can do is cherish them in the present.

Morning walks

Today I’m going on an early morning walk with my buddy.

I couldn’t think of a better way to jumpstart the day.

It’s a lovely reminder of how important (and impactful) it is to do something with others with no phone around.

No internet. No notifications. Just laughs and conversation.

A friendly weekend

It’s always a bittersweet morning when a friend leaves after visiting for the weekend.

When he arrived on Thursday night, I thought, Wow, we have three nights. He’ll be here forever!

But as happens every time, the weekend flew by and before I knew it I was hugging him goodbye.

He left me with some insight as he packed up his stuff. He said it rarely feels like his trips last the perfect amount of time; it’s either not enough time or too much. “I prefer when it feels like I wish I had more time. I remember the trips purely as fun, with zero frustration. Also, it makes me excited for the next one.”

It certainly wasn’t enough time…I am looking forward to the next one.

Visit your friends.

VYF

I took the weekend off because one of my best friends is visiting.

He’s sitting right behind me on his computer as I type away on mine.

Today we’ll go for a hike, get some lunch, play some chess…

Life is good. Visit your friends.

Find a buddy

Two buddies drinking at a bar and celebrating

This morning, I swam laps with my best friend at the local center.

There was literally no chance I would’ve done that alone at 7am. I needed a buddy.

Get yourself a buddy. They’ll motivate you and hold you accountable for things you don’t really want to do.