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.


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.


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.


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.

The E-Myth

I just finished The E-Myth Revisited by Michael Gerber.

It was a super helpful, albeit cheesy book on running a business.

Here are my two biggest takeaways:

1) Being a Technician—i.e. being skilled at your craft/service—does not qualify you to be a business owner.

Great bakers, coaches, or carpenters don’t necessarily make folks who are great at running bakeries, practices, or home remodeling companies. Running the back end of a business is a completely different ball game.

In short, there’s a huge difference between working in your business and working on your business.

2) Your business is not your life; it should fuel your life.

I needed to hear this.

For the past year, I’ve been growing my first ever business and have become more and more passionate about it as it grows each month. Thinking about my business—creating clients, scheduling calls, inviting people to coaching sessions….I would be focusing on this stuff almost 24/7.

I wore that like a badge of honor, but I had to be reminded that that wasn’t my life. My life is my friends, my family, my health. My life is the freedom I enjoy with the people I love. I want my work to give me more freedom, not chip away at it.

If anyone owns any kind of business, or is at least considering it (no matter how big or small), I would consider this book mandatory reading.

The Addict Brain

A female addict drinking wine and smoking a cigarette

Last night, I really wanted to stay up and watch YouTube videos on my phone. I wasn’t tired enough to go to bed at my ideal hour: 10pm.

I recently listened to a podcast where a comedian talked about the Addict Brain. He was using it in the context of cocaine and cigarettes, but said it applies to almost everything we do.

To be clear, I have friends and clients who have been to rehab and have been sober for years because of their addictions. By no means have I experienced an archetypal, debilitating addiction to drugs or alcohol.

But the Addict Brain is at play whenever we are faced with something we know is no good for us but our mind tells us: “Don’t worry, it makes sense for you to do this!”

Logically, I’m 100% certain I will regret these things if I do them:

• DoorDashing a large Wawa sub with mac and cheese instead of cooking a decent meal.
• Staying up watching YouTube on my phone until 12:30 at night.
• Skipping my meditation, the gym, or jiujitsu.
• Watching porn.
• Playing video games instead of going to class (when I was in high school and college).

When I have been faced with these decisions, logic is never at play. The Addict Brain throws rationality out the window. I say I’m certain I’ll regret these things because I have mountains of evidence which prove that to be true. I’m never happy or fulfilled after doing any of these things.

So last night, when I had all the energy in the world to stay up later and watch my favorite chess streamers…I turned my phone off and tried to sleep. After 20 or 30 minutes of tossing and turning, I woke up this morning, slid my sleep mask off, and began my morning routine feeling refreshed and grateful.

Thus is the age-old battle between instant gratification and long-term fulfillment.

I’m fulfilled when I’m:

• Eating well.
• Getting great, consistent sleep.
• Active and mindful.
• Present.
• Productive.

The thing is, all this stuff takes time. It’s a slow burn. It compounds, meaning it takes a while to feel the effects but the longer we do it the stronger those effects are.

Example: I’m not just working out this afternoon so I can feel accomplished today. I’m working out this afternoon and then consistently after so I can look good with my shirt off, do fun and athletic things in the future, and be in great shape for my partner and family down the road.

But it all starts today.

It begins with our next meal, with tonight’s bedtime routine, with the next workout. And then the next one. Then the next. And so on…

The Addict Brain wants to keep us from being healthy and fulfilled. But fuck that.

My religion

A person praying next to a bunch of candles

I am not religious at all, but here’s the closest thing I have to a faith-based belief:

Every single one of us has the ability to create the life we want, and the only thing in our way are the stories we tell ourselves.

These stories may sound like…

• “I’m just not x.
• “I don’t know how to y.”
• “I need to be more z.

But they’re all complete nonsense. Understandable nonsense…but nonsense all the same.

There are people without limbs in the Olympics, blind musicians, and impoverished and oppressed people who become financially free.

That doesn’t mean it’s easy and that doesn’t mean we should do nothing for those less fortunate. It’s a battle for all of us. Some will have to fight harder than others.

Me, for example…I grew up in a great neighborhood, had loving and supportive parents and friends, and have never feared for my life. I have both gone through hell, and at the same time, had it super easy.

This isn’t some “being broke is a mindset” blog. I advocate for compassion and understanding of all.

But I encourage anyone to fight for what they want, wherever their starting line is.

How you do one thing

I’ve found that when one area of my life begins to slip, so too do other areas.

When I skip on a bunch of exercises in a week, it tends to be an unproductive week of work as well.

When I have an unproductive week of work, I feel less secure in my friendships.

When I feel less secure in my friendships, it’s harder for me to cook healthy meals.

The opposite is also true. When one thing is going super well, other facets of my life seem to thrive.

“How you do one thing is how you do everything.”

Anxious dogs

Three curious dogs looking up

I’m watching my mom’s dogs for the week. They’re both anxious as hell.

One has separation anxiety. The instant I walk out the door he starts barking and crying until someone returns. The neighbors love it.

The other can’t make it halfway around my apartment building without trying to shed her harness off. She gets terrified by the sounds around her: cars, birds, cicadas…and pleads to head back to the house.

Logically, the first dog must know that someone will come back home. They always do. And the second dog must know that nothing is going to attack her while we’re on our walk. Nothing ever does.

But we can’t logic away our emotions.

I firmly believe that we should train ourselves to step away from powerful emotions which aren’t serving us. But that doesn’t eliminate the fact that we feel powerful emotions.

When I see someone get triggered during a socio-political conversation, I think: That’s not useful. But I never judge that person. We experience emotional responses that aren’t useful almost every day.

Extreme pride, shame, panic, disgust…These almost never serve us.

If I could explain to these dogs that they have nothing to worry about and they changed their behavior, their lives would become much easier. But how often does that actually happen?

We all know that person who got back with their shitty significant other after being cheated on twice. That’s clearly illogical. But we’re not logical beings. We make decisions based on our emotions and then justify them with logic.

We’re not awful people for having harmful emotions. But it’s up to us to not let them dictate our actions or decision-making.

Pick your stress

A stressed woman with her hand on her forehead

We often wonder or are asked, “What do you want in life?”

Naturally, this is an important question. It’s valuable to be able to paint a vivid picture of what our ideal life looks like or what we’re working toward. But I don’t actually think it’s the most useful question if we want to know these things.

Pain, discomfort, doubt, anxiety, displeasure…These are all totally natural experiences as we go about our lives. Unless a person has achieved enlightenment, they’re a liar if they claim to never feel any of these unpleasant emotions.

I live a fulfilling life. I love what I do, have amazing friendships, am healthy, and have a number of hobbies and passions I pursue…And I experience these shitty feelings all the time.

The question most people fail to ask themselves is this:

What stress am I willing to experience?

Let me explain.

Last year, I worked my first sales job and fucking hated it. I dreaded going to work, wasn’t good at it, and would come home utterly drained and void of energy to do anything I cared about. That was stressful.

During lockdown, I quit that job and started freelancing. I had to teach myself skills I’d never tried before and ask people to pay me to do them, wasn’t good at it, and never knew where my next paycheck would come from. That was stressful.

But here’s the thing: I was super willing to take on that second form of stress. The stress from my old sales job broke me. The Resistance was higher than the value I got out of it. But when I was freelancing, the freedom I experienced in creating my own schedule and living life on my own terms was totally worth the discomfort I was feeling.

Stress and discomfort are natural constants in life. What discomfort are you willing to go through? What makes it all worth it?

Sometimes I wake up depressed

Money, overwhelm, habits falling off.

I take very good care of myself…but I’m still a human being, which means sometimes I don’t.

What do I do when this happens?

• Tell my support system—friends, mom, colleagues.
• Let myself feel this way—i.e. don’t try to hide it or convince myself otherwise.
• Exercise.
• Help other people.

Ups and downs come and go. But neither lasts forever.

Can I help?

In a session yesterday, a client told me about the two question he asks himself when talking to a prospective client.

I think they could be applicable to any kind of relationship:

1) Can I help this person or add value to their life?

2) Do I want to?

We’re talking about practice, man

A chess board on a bed

I started playing chess last summer. Since then, I’ve played almost every day.

One of the main reasons I got into it was because one of my close friends played as well. He would destroy me, and we’re both quite competitive so that was all the drive I needed to want to improve. I had a worthy rival: Someone just ahead of me to push and challenge my skills.

I read books, got a chess tutor for a month, and have watched mountains of chess content on YouTube.

After about a year of playing consistently, I finally feel like I’m at the point where I can play my friend and confidently beat him most of the time. (Sorry, Andrew!)

This makes me happy for a number of reasons:

1) Feeling our skills improve is one of the best experiences in the world.

Seeing our muscles get bigger, or timing sharpen, our understanding flow better…There is a motivating excitement that comes with any sort of visible growth.

What we’re trying to improve becomes more fun since we can simply do more things.

2) Competition is fun.

For many of us, that competitive drive will never leave. But as we get older, the hope is that we channel it in more productive ways.

Winning in chess is obviously more fun than losing (especially against a good friend), but what’s more fun is competing against my past self.

Dillan's chess rating

Seeing my ELO increase is jubilating. (An ELO is the number that rates a player’s skill level.)

It took me a while to break 1300. Now I’m trying to break 1400. And so on.

3) The Growth Mindset is real.

The Fixed Mindset is the idea that every skill falls into having natural ability or not. Some people can and some people can’t.

People with a Fixed Mindset say things like:

• “I’m just not a musical person.”
• “I suck at this.”
• “This just isn’t something I can do.”

Of course, we all have certain strengths and weak spots. But the Growth Mindset states that if we just put enough time and energy into something, we can improve at it.

Example: I’ve said my whole life that I’m not a business guy. Now, after running a coaching business for about a year, I’m training and coaching others on how to run their businesses. Practice, bitches.

There have been plenty of times where I wanted to stop playing chess because I felt like I had plateaued. But I just kept playing and practicing.

I’ll leave you with one of my favorite comics…

A comic about practice

Swimming is hard

A happy man riding a bike during a triathlon
(Not me.)

I completed a sprint triathlon yesterday morning with my best friend.

A quarter-mile swim. A 12-mile bike. Then a 5k run.

I didn’t prepare for it nearly as much as I should have. Prior to the event, I only swam three times and ran two. Not ideal.

The swim was the toughest part by far. My arms were exhausted during the last few laps. Once I got out of the pool, it felt like I won the entire event…despite being like 200 people behind.

We went into the pool one by one, swimming through each lane down and back, then under the rope and into the next lane. We went in based on our swim times. Naturally, I went in with the last group because I assumed I would need to take a few breaks. I made friends in line and we bonded over our lack of ability.

My buddy went in way ahead of me….He had prepared properly. I got into the pool 15 minutes after he got out. Our plan to complete the triathlon together went out the window.

I was feeling insecure coming in because of my lack of training. I feared being surrounded by a bunch of super-athletes judging me for not taking this as seriously as I should’ve. But I learned something powerful yesterday.

There were folks of all kinds of shapes, sizes, ages, and capabilities competing. Here’s the lesson I gathered from seeing all these wonderful people do their thang:

There will always be a shit ton of people who are way better than we are at something. There will always be a shit ton of people who are way worse than we are at that same thing. It doesn’t make sense for us to compare ourselves to either group.

We should learn from and be inspired by those ahead of us and help and teach those behind us. We need only compare ourselves to who we were in the past. Am I better than I was last month? Last week? Yesterday?

When I was in line for the swim, I met an 82-year old who has done a ton of these events. I’ll leave you the advice he left me.

If you’re not having fun, you might as well stay home.

82-year old badass

Triathlon prep

I’m doing a triathlon tomorrow.

I’m woefully unprepared for the swim portion, but I’ll make it happen.

The date seemed to pop up out of nowhere.

It was a lovely example of the importance of being proactive so our future selves can be happier. There were several days where I decided not to go swim laps because I simply didn’t feel like it. It truly felt like I had all the time in the world to prepare.

“Not today. Next week though…I’ll definitely do the work later.”

But later never comes.

The best time to do the work is always right now.

At the same time

Things can exist at the same time.

A person can be doing very well and be violently anxious.

Police brutality and black-on-black crime can both be problems to mend.

Something can feel super easy and incredibly difficult.

This blog post can be wildly insightful and dumb as shit…at the same time.

Write like a motherfucker

A person writing with pen and paper

Last night, I finished another chapter of Cheryl Strayed’s Tiny Beautiful Things. It was my favorite one yet.

The book consists of captivating Dear Sugar columns; people write in asking for her advice and she tells gripping, emotional stories and gives life-changing insights.

The chapter I read before bed last night was called “Write Like a Motherfucker.” In it, a woman wrote in looking for much needed motivation. She’s a writer who doesn’t write. She’s often paralyzed by her depression.

She writes:

“I’m…a high-functioning head case, one who jokes enough that most people don’t know the truth. The truth: I am sick with panic that I cannot—will not —override my limitations, insecurities, jealousies, and ineptitude, to write well, with intelligence and heart and lengthiness. And I fear that even if I do manage to write, that the stories I write will be disregarded and mocked.”

What powerful vulnerability. And what a concrete example of someone who wants something but believes there’s something in the way.

To be clear, I am NOT downplaying the role of mental health here. I love that Cheryl opens by recommending professional help to this woman. The power of not having the energy to do what we want to do is stark.

But the reason I love this chapter so much is because Cheryl throws down some masterful tough love.

The phrase tough love often gets a bad rep. People tend to get distracted by the first part, tough: possibly unpleasant, firm, or uncomfortable…that they forget about the second part entirely, love: coming from a place of “I care about you and your wellbeing.”

I believe in accepting others for who they are and showing consistent compassion to ourselves and those around us. But I also believe in challenging ourselves and those around us for the sake of pushing humans to be better.

Cheryl hits her with this hammer:

“The most fascinating thing to me about your letter is that buried beneath all the anxiety and sorrow and fear and self-loathing, there’s arrogance at its core. It presumes you should be successful at twenty-six, when really it takes most writers so much longer to get there.”

Wow. No pity party here.

I can only imagine how much this stung to read. But Cheryl does a fantastic job in relating her own experiences and assuring her that this all comes from a place of love and care. Plus, the point is not: Does this sting? The point is: Is this true and is this useful?

Going through mental chaos is God damn difficult. In many cases, it can be debilitating. But unfortunately, that doesn’t remove the work that needs to be done.

Cheryl describes humility: not being up too high or down too low, but on the ground level. She writes:

“We get the work done on the ground level. And the kindest thing I can do for you is to tell you to get your ass on the floor. I know it’s hard to write, darling. But it’s harder not to. The only way you’ll find out if you “have it in you” is to get to work and see if you do. The only way to override your “limitations, insecurities, jealousies, and ineptitude” is to produce. You have limitations. You are in some ways inept. This is true of every writer, and it’s especially true of writers who are twenty-six. You will feel insecure and jealous. How much power you give those feelings is entirely up to you.”

The negative feelings we experience are absolutely valid. But the work still needs to be done. It’s up to us to continue to show up and do it.

“Writing is hard for every last one of us—straight white men included. Coal mining is harder. Do you think miners stand around all day talking about how hard it is to mine for coal? They do not. They simply dig…

You need to do the same, dear sweet arrogant beautiful crazy talented tortured rising star glowbug.

So write…Not like a girl. Not like a boy. Write like a motherfucker.”

(Strayed, Cheryl. Tiny Beautiful Things (p. 60). Knopf Doubleday Publishing Group. Kindle Edition.)

Nothing’s wrong

One plus one equals three
A real photo of my senior thesis.

I got coached by a friend yesterday. I came into the session with the past two weeks containing more stress and anxiety than I’ve felt in years. Here’s what happened.

It went well. She’s a great coach. But often times we go into a coaching session thinking we’ll leave with total relief and clarity. We believe if we come in with negative emotions, we’ll talk out our feelings and reach the insight that we don’t need to feel them at all.

But that’s not always true.

When she asked what was going on, I told her that in the past two weeks:

• my biggest possible client pulled out
• I have a big presentation coming up, and
• I’ve been falling off with my habits

Talking this shit out is always powerful. Talking it out with a coach who knows what she’s doing is always 50 times more powerful. These were my three biggest takeaways:

1) Nothing’s wrong.

Feeling discomfort—stress, anxiety, uncertainty, doubt, fear—is a natural part of the human condition. Why then do alarms go off when we feel these ever-occurring emotions? Our fight or flight response is activated and our bodies tell us in one way or another that something’s wrong.

I had to remind myself that I’m constantly stepping out of my comfort zone, I’m running my own business, I’m new at it. Rather than thinking I don’t need to feel stressed, I came to the realization: Of course I feel stress! And that’s okay. Who wouldn’t?

In other words, nothing’s wrong.

2) Three magic questions.

Be it with my coaching, my hobbies, or anything else I want to pursue in life…I basically boiled down my life purpose into three questions:

• Am I having fun?
• Are other people having fun?
• Is this helpful?

The answers to those three questions tell me whether or not I’m in the right space.

3) I always figure it out.

I have flunked out of college, tried to kill myself, and been in $80,000 worth of debt with no job. And I’m still here…typing out this blog.

We often feel like if we don’t “figure it out” (whatever the hell ‘it’ is), we’ll fall into a black hole. But no, we just wake up the next morning. We adapt. We figure it out.

The important thing is to continue to be vigilant about figuring it out. Ask questions. Get a coach. Share thoughts and feelings.

When we do all of these things consistently, we come to understand that no matter how we’re feeling…nothing’s wrong.

Slipping up

Today is one of those days where I wake up and realize that my habits have been off track.

I’m looking at my phone past 10pm.

I haven’t been doing my weekly review on Mondays.

I haven’t even been working out as much as I normally do.

Perhaps it’s because of stress. Whatever it is, the shitty feeling of not taking care of myself as well as I normally do packs on even more stress.

This is natural. It happens every so often. No need to freak out. Just have to readjust and get back on the horse.

Funny enough, I’m riding horses today with my mom for the first time. Pretty perfect.

The first day back at the gym after taking a break always sucks. But it’s a necessary suck. It’s like paying my dues for slacking. That’s okay.

“Too often, we fall into an all-or-nothing cycle with our habits. The problem is not slipping up; the problem is thinking that if you can’t do something perfectly, then you shouldn’t do it at all.”

James Clear

Why do I feel this way?

A baby playing with macaroni

Yesterday, I had a conflict with my best friend. The thing was, he had no idea because it happened entirely in my mind.

The details aren’t super important. We had made plans to do something that I was excited for. He backed out the day of because he wasn’t comfortable doing it until next week.

All the logical parts of me were saying: Of course man. You don’t have to do anything you’re uncomfortable with!

But my automatic emotional response was something entirely different. I felt like: Really man? Come on, you pansy.

I noticed right as it was happening. If I logically know his choice makes sense and is fine, why do I feel hurt and frustrated? Or, put in a cheesier way: Why is my brain saying one thing but my heart is feeling another?

I wanted to text him back but I worried about being in too emotional of a state to say anything of substance. I remembered the advice I’ve heard and have given several times: Don’t respond in an incredibly emotional state—be it anger, sadness, or even excitement.

The reason being that our emotions are fleeting. Especially if it’s a powerful emotion, we most certainly won’t be feeling that way for very long. So naturally, when we respond to someone in that state, we tend to regret what we’ve said or done when time passes and we come out of it.

I didn’t respond. I remembered my training.

As the day came to a close and I finished working, I still felt a slight tinge of disappointment. But I was quite glad I didn’t say anything earlier. Whatever it would’ve been, it wouldn’t have been productive.

I went to jiujitsu and called him when I got out. I told him everything.

It was a truly lovely and utterly strange conversation. I wasn’t saying sorry, but I felt bad. He had nothing to forgive, but he felt reconciled.

We came to the conclusion that I tend to have emotional reactions when things don’t go the way I thought they would. I’ll have it in my head that it’s going to be this, but when that doesn’t happen, my internal response goes, This isn’t how it was supposed to happen!

I asked him about times when his logic and emotions were saying two different things. We shared stories, discussed mindfulness, and expressed gratitude for our ability to have such open conversations.

We laughed as we compared this phenomenon to when someone’s partner dreams they cheated and wake up pissed off at them. Logically, they know nothing happened…but they just emotionally experienced something traumatic.


• We’re emotional beings. We make decisions based on emotion and then justify them with logic.

• While it can be scary or uncomfortable, having totally candid conversations with our close friends is one of the most rewarding experiences out there.

• We cannot control our thoughts or emotions. They simply arise. What we can control is whether or not we let them dictate our words and actions.