First photo shoot

I auditioned for grad school programs for acting in 2016. I sat in a Broadway hotel room and performed various monologues for scouts from colleges around the globe.

After exhausting my character resume, the head of the University of Houston asked me to sing a song.

“A…song?” I froze. No one had ever asked me to sing a song before.

“Yes,” he replied. “Any song you know the words to. I assume you’ve heard a song before?”

While I appreciated his roasting, it didn’t help with the pressure of remembering lyrics. I spent five whole minutes thinking about any song I knew the words to.

It was an embarrassing and hilarious experience. And I just felt that same feeling seven years later.

I’m building a new website in the next two months so I got some professional photos taken. She said, “Just pretend I’m not here and act casual and confident.”

I’ve never felt so uncasual and unconfident in my life.

But I thought I’d share a few here since I don’t really care for social media. Feel free to print them out, put them up on your walls, build a shrine. Whatever you want to do.

The 5 traits of the most successful people I’ve coached

A hiker at the top of a mountain cliff

This week, I hit my 1000th coaching hour. That means I’m a certified Master Insight Coach. It took me one year, six months, and four days.

I’ve coached nearly 100 different people these last few years. This has given me a pretty good look at how we make decisions, what we’re afraid of, and our capacity for growth.

I’m lucky to have been able to coach some amazing people. Some of them I see myself working with for years and years to come.

Humans are infinitely complex and quite simple at the same time. We all have different personalities, strengths, and limiting beliefs. But we all want stuff, feel there’s stuff in the way of that stuff, and then either do something or nothing about it.

There are five major traits I’ve seen in the people who crush life. I see these folks as genuinely successful.

By “successful,” I’m not factoring in their income. I measure success by how fulfilled a person is by the life they’re creating.

Here we go.

1) Ownership

The top characteristic I’ve seen in people who move in the direction they want.

They don’t blame things outside of their control for their situation. They might mention them, but they quickly dive into what’s in their control to do something about it.

“Not everything is my fault, but it is my responsibility.”

The people who actually get what they want in life understand that if they want to experience change, they have to change.

2) Doubt, fear, and anxiety

“You’ve got to be fearless” is bullshit advice.

Humans are wired to stress about things. Only now, we don’t worry about getting attacked by animals; we ponder our purpose in life.

No matter how well a client is doing, they tend to still be afraid and doubtful as they level up.

  • “I don’t know what I’m doing.”
  • “Maybe I’m not cut out for this.”
  • “What if I screw up now that the stakes are higher?”

I’ve heard this all a thousand times. But they always get through it.

Which brings me to #3…

3) Doing the scary thing anyway

Successful people realize that they’re allowed to feel how they feel. Emotions come and go naturally.

But they don’t let these feelings stop them from doing what they want. They experience the growing pains of improvement.

It goes like this:

Step 1: I want this new thing
Step 2: I’m going to take action to get it
Step 3: This isn’t as easy as I was hoping
Step 4: I don’t know if I can do it
Step 5: I’m kind of doing it and it’s actually not that hard
Step 6: I can do anything I set my mind to
Step 7: Repeat

4) Committed and focused

The people who are most serious about improving their lives play full out.

They show up on time, are ready to take notes, and are eager to take action.

They are also prepared to invest in themselves. Not just with money, but time and effort as well. They make their well-being a priority.

5) Growth mindset

Those who climb the mountain know the only thing between where they are and where they want to go is time and effort.

They stay away from fixed phrases like “I can’t” or “I’m not the kind of person who…”

Deep and meaningful change is possible for every single one of us. The only way it wouldn’t happen is if we choose for it not to happen.

Take a person who is convinced they couldn’t run a marathon. They’re unlikely to start training for one. They won’t register for one to give them the incentive. They won’t find a training partner to hold them accountable. Six months will go by and they’ll be in the exact same place…thus proving themselves right.

Successful people realize the journey will be more difficult, uncomfortable, and complex than they originally thought. But they keep practicing and doing.

The hard becomes easy. Then they look to new challenges.

Which of these traits do you feel you have? Which do you think you need to work on? Reply to this email and let me know.

The journey down south (pt. 5)

I was either chewing a granola bar or was terrified to cross the rickety bridge.

(First, check out parts 1 through 4.)

Day 3

After a magical night of mushrooms, chess, and beer, the four of us got up for some Sunday hiking. The original plan was to wake up around 6am to get to this gorgeous waterfall two hours away.

That was hilarious.

So instead, we woke up at 9 and went to one of their go-to parks about 40 minutes from Asheville. We brought our hiking gear and a cooler with a few beers. We also stopped at a cafe for some road sandwiches.

The green mountains around Asheville have some of the best hiking I’ve ever experienced. It was with these same friends that I ate shit while hiking next to a waterfall a few years prior. They saw me slip and fall a good 10 feet down the steep hill. About five feet in, I thought, This is how I die.

This hike was much chiller (flatter). We parked, found a trail, and let Nanny off the leash. They were taking me to the creek. Or to my death…I’d find out soon.

After I snapped this Nanny said, “delete it.”

We found the water and stepped in up to our knees. It was freezing. I resisted the urge to cannonball into the deeper end. The rocks were slimy and slippery and I didn’t want to sprain my ankle in the Appalachian wasteland.

Similar to the night before, I felt like a kid again.

We skipped rocks, played fetch with Nanny, and basked in the sun. I felt envious of my friends that they had such frequent access to stunning nature. That’s my biggest qualm with moving to New York City.

I love green. And while I’m wildly extroverted, I crave quiet and isolated places…So I thought I’d move to one of the most populated cities on the planet.

Anyway, we finished a lovely hike and made it back to the car. The passengers cracked some beer and we headed back to the apartment.

I had been in communication with one of my coaching friends who was getting into Asheville that night. We met in our online coaching community and bonded over the topics of entrepreneurship, money-making, and dating.

She got into town and we met up for dinner. It was our first time meeting in real life.

I’ve done that now a handful of times. So be the times. Here’s the process:

  1. Build a strong relationship with someone over Zoom/over the phone.
  2. Make a plan to meet them in real life.
  3. Travel to execute that plan.
  4. Experience the surreal feeling of seeing what they look like in real life—how tall they are, what the side of their head looks like, how they walk.
  5. Feel two conflicting emotions at the same time: 1) It’s my good friend! 2) I have to get to know this person.

All that happened as we ate at this delicious Hawaiian restaurant. Half of me was chilling with my buddy and the other half was on a job interview.

Regardless, we had a fun evening. She met my friends and got recommendations for how to spend her remaining few days in the city. She was going with the flow and I shared that sentiment.

But I did need to get my car back at some point.

Day 4

On Monday morning, I called the repair shop to make sure I could pick up my 2009 Nissan Tesla (one of the lesser-known models).

They told me they were down a mechanic and would have to get to it tomorrow.

My thought was: All good. I have plenty of time. The retreat isn’t until Thursday.

While the adults were off at work, I used their cabinet desk to get some writing done and to respond to emails.

I texted my friend and updated him. When he got home, we started watching Lil Dicky’s show, Dave. He loved it.

Day 5

On Tuesday morning, I called the shop to confirm. They told me they needed to order a part and that I’d have to wait until tomorrow.

My thought was: What the God damn fuck, I need my car.

I was starting to get nervous. It felt like my car was being held hostage.

When they got home that day, we watched a few more episodes of Dave and then went out to a brewery for dinner.

Day 6

On Wednesday morning, I called the shop to confirm. My heart was racing.

I went for the assumed close: “Hey. So you guys are repairing my car today and I just wanted to make sure I could pick it up after working hours.”

He asked for my name and the make/model of my car. When I gave it to him, he put me on hold to check and see if they’d be able to fix it that day.

My thought: This.

After five minutes, he came back and said we were good to go for today. I could pick it up whenever I wanted and could pay for the repair over the phone. The dark clouds vanished.

“Thank you,” I said. I shared the good news with my friends and we left as soon as they were done working.

You never really appreciate something until you experience life without it.

Florida, here I come.

2am nightmare

Every month or two, something shitty happens.

I wake up in the middle of the night—usually around 2 or 3 o clock—and I’m wide awake. Each time, I think it’s like 30 minutes before my alarm is supposed to go off. Then I check the time and panic.

I’ll walk out of my bedroom and read or listen to a podcast. Something light until I get sleepy.

Eventually, I get tired again. But that tends to take another two to five hours. If I fall back asleep, it’s for another hour at most. Then I have to get up and start my day.

That happened today. I feel like a zombie. And I never know what to do.

I canceled my last call just to take a nap.

Anyone else experience this?

Another getaway

I’m spending the weekend in Brooklyn with a group of friends.

I’m always excited to explore my future home.

When I get back, I’ll share pictures, stories, and insights.

Coming up this week:

  • Downloading a dating app for the first time
  • Quitting coffee
  • Slowing down while being super career hungry

See you Monday.

Logo poll

Hi friends!

I need your help. I ran a design contest for the new logo of my LLC.

Can you please take 10 seconds, look at the final eight designs, and tell me which one is your favorite.

Here‘s the link.

Philly feedback

Connor Russo and Dillan Taylor

Here are my biggest takeaways from the feedback exercise I did with one of my best friends this weekend.

1) I struggle with portion control.

My buddy said something that hit me hard.

“I like hanging out with sober Dill way more than drunk Dill.”

He brought up the fact that I used to drive home drunker than was comfortable. That part was easy to swallow because I remember the day I vowed to never do that again—December 28, 2019.

But as for being drunk Dill, he called me out on something I’ve battled with since I was 18: the number of drinks I have when I drink.

On average, I only drink about twice a month. But when I do, I drink like I’m 20 years old. I haven’t reprogrammed my brain. When I have a beer, I want a second. When I have a second beer, I want a third. And so on.

TAKEAWAY: I will buy smaller quantities of alcohol when drinking with others. Six-packs, single bottles of wine, etc. If it’s not in the pantry then I can’t drink it.

2) I can be more welcoming to opposing opinions.

I love and appreciate the fact that we’re all so different, but sometimes when someone sees certain things differently than I do, I get confused.

Adam Grant introduced me to a useful term: logic bully.

For years, I thought breaking things down rationally was the only way to solve problems and get at truths. Unfortunately for me, that’s not how everyone operates.

My buddy pointed out that I could be more light-hearted in my disagreements. Even if I’m confident in my opinion, it could be more harmonious if I didn’t treat it as an objective fact.

Depending on the topic, this one will definitely take a lot of work.

TAKEAWAY: When I disagree with someone, I will slow down. I’ll try to steelman their points, separate the person from the idea, and ask questions as if I’m agreeing with them for the sake of the argument.

3) People love positive reinforcement.

It’s healthy to be able to do what my friend and I did—articulating areas of improvement and airing grievances. But he pointed out that hearing praise and appreciation from me just feels incredible.

The challenge is (especially for men I think) this can often sound cheesy.

Telling people what we love and respect about them and highlighting what they do really well…it takes practice.

I tell my friends I love them on the phone. I hug them. Sometimes it doesn’t feel natural. Sometimes they have no clue what to say. That’s okay.

I’d rather feel a bit corny than have my friends question how I really feel about them.

TAKEAWAY: Continue to consistently tell the people in my life what they mean to me and what I think they do well.

I encourage you to do your own feedback exercise with your friends!


Merry Christmas, ya’ll!

2 days of rest

I’ll be taking the next two days off.

Enjoy your holiday with those you love!

I have a blog?

Due to thoroughly enjoying this vacation, I’ve been neglecting this blog.

Such is life.

Dank blogs to come.









This simple habit makes me super happy

An iPhone resting on a wood floor

Aside from keystone habits (habits that make other habits easier) like good sleep and exercise, there’s no one habit to rule them all.

A fulfilling life typically consists of a number of healthy routines and practices. I do enjoy giving out tips and tricks on my favorites, but here’s one I often forget about:

Start your mornings without looking at your phone.

The mornings should be about control. They’re your time to take charge and set the stage for the day.

If I have a sluggish and lazy morning, the rest of my day is sure to follow suit.

And nothing pulls me out of the driver seat like looking at my phone right when I wake up.

You never know what you’ll see in your messages or on social media that will pull you away from the present moment. You could get stressed. You could get pissed off. Hell, maybe nothing will happen.

But that’s the point. Checking your phone is like pulling on a slot machine; it comes with infinite uncertainty. And uncertainty is not the best way to start the day.

I’m not saying you should neglect your obligations. But consider taking an intentional pause before you dive right into them.

Taking just 10 or 20 minutes to drink water, make some coffee, or do some stretches will do wonders for your mindset and your ability to have a productive day.

Your emails and notifications aren’t going anywhere.

I go the first hour or two with my phone on airplane mode each morning. I work for myself, so I know that’s unreasonable to ask of most people.

I’m also aware that some folks have wild schedules, families, and jobs where they are basically on-call.

But if you can’t take 10 mindful minutes out of your morning to pause before you start your day, then you are the person who most needs this in their life.

It’s Always Snowy in Philadelphia

Snowy weather in Philadelphia

Last night, I made a game-time decision to drive up to Philly to beat the snow and visit my friends for the weekend.

Three short lessons and I’ll have you back to the rest of your day:

1. Before you pack up the car, write a list of every item you want to bring on paper or in your Notes on your phone. 

As you put items in the car, cross them out or delete them. This may feel tedious at the time, but it’s the only way to ensure you remember 100% of what you want to take (leaving or returning). 

The same thing is true when you go grocery shopping. When I shop without a list, I always come back with more donuts than anticipated.

I made a list for this last-minute trip, but it was too vague. I wrote ‘Work Stuff,’ so I brought my laptop and notebooks. But I forgot my mouse and keyboard.

I’ll be fine without them, but taking six seconds to write those things down would’ve saved me the inconvenience.

2. Visit your damn friends.

There are only so many opportunities to spend memorable, quality time with the people you care about. Take advantage of them.

Take the long weekend. Buy the plane ticket. Pack the car.

It’s always worth it.

3. Have conversations with your friends with no phones in the room.

And old friend told me years ago, “When you’re with someone and they have their phone out in front of them face up, it’s basically a big fuck you.”

Some of you might get defensive when you hear this, but it’s true. It tells the person that they are not the priority. It says, I’ll give you my attention until I get a notification.

Look around the dinner table and see how many people have their phones out.

Unless you’re waiting to hear back about your brother in the hospital, put your fucking phone away when you’re spending quality time with friends. A few dives into your phone can completely upend a conversation.

Last night, the three of us sat and talked and caught up for three hours. Not one of us looked at our phones. It can sound corny, but this meant our only option was to look at each other and actively listen to everything that was being said.

99% of the time, you don’t need your phone. 

Put it away. Keep it in your coat pocket. Hell, leave it in your car.

You’ll survive.


A lesson from Harry Potter on happiness

Hogwarts School of Witchcraft and Wizardry

Something resonated with me as I finished another chapter in the final book of the series: The Deathly Hallows.

Harry, Ron, and Hermoine have just completed a suspenseful, dangerous mission. Their goal was to steal a Horcrux: a locket containing a piece of Voldemort’s soul, the story’s antagonist.

After barely making it out alive with the Horcrux, they set up camp to plot their next move. Harry’s emotions at this moment provide a valuable lesson.

“He had thought that he would feel elated if they managed to steal back the Horcrux, but somehow he did not; all he felt as he sat looking out at the darkness, of which his wand lit only a tiny part, was worry about what would happen next. It was as though he had been hurtling toward this point for weeks, months, maybe even years, but now he had come to an abrupt halt, run out of road.

There were other Horcruxes out there somewhere, but he did not have the faintest idea where they could be. He did not even know what all of them were. Meanwhile he was at a loss to know how to destroy the only one they had found, the Horcrux that currently lay against the bare flesh of his chest.”

In other words, you can accomplish your biggest, baddest goal…solve the most complicated problem on your plate right now…and the only guarantee is that you’ll now have different problems to solve.

This isn’t to say you shouldn’t pursue your goals. The point is to step away from the mindset that “Once I do or accomplish x, then I’ll be good.”

But you’re never “good.” You can certainly be better, but the work never stops.

If you win an Oscar—regardless of the euphoria and elation you feel giving your acceptance speech in front of the all-stars of Hollywood—eventually, your speech will end and you’ll be escorted offstage. You’ll give a few interviews, chat it up with Leo or Meryl, and go home.

The feeling of being an Oscar winner will surely stay with you for a short while, but for how long?

Soon you’ll have to find your next role. You’ll have to parent your kids. You’ll have to get back into your exercise routine. Life doesn’t just stop when you achieve something brilliant. Cancer or stress or relationships…these things don’t give a shit about your little golden trophy.

When we put all of our self-worth into accomplishing certain things, we feel a natural ache as that good feeling dissipates.

There’s a way around this.

If instead, you become fully aware and prepared for the short-term nature of these victories, you will be able to appreciate them and move on.

I doubt you’ll be hunting down jewelry with your enemy’s soul in it any time soon. But consider this the next time you put a ton of value in accomplishing something.

Appreciate buying a house. Then, prepare yourself for the HOA, mortgage adjustments, renovations…

Appreciate your new job. Then, prepare yourself for new coworkers, a new routine, different responsibilities…

Appreciate your increased income. Then, prepare yourself for taxes, lifestyle creep, greed…

The problems never stop. They just lead to different problems. Keep solving them.

Fiction books and sitcoms are lovely. But they end at the resolution. They never show us what happens after.

Once Harry defeats Voldemort, I reckon he’ll need to find a job.

How to Change the World in 2 Hours

I almost killed a guy yesterday.

Well, not really. But I thought about it.

It was just one of the numerous negative thoughts boiling in my head as I was driving around. Running on just five hours of sleep, I was truly the worst version of myself. That’s when I realized:

How many of us are out and about in the world–sleep deprived, groggy, improperly fed–interacting as a shitty version of ourselves?

Let me explain.

After I caught myself contemplating running over that dude (To be fair, it was a biker on a narrow, winding road–How dare he?), I finished up my errands and went to the gym.

Despite wanting to just go home and lay down, I dragged myself through an intense workout. Without fail, I walked out feeling almost high with endorphins. There was a smile on my big, dumb face and as cheesy as it sounds…I felt like myself again.

It was as if I woke up from the Matrix. The thought of bringing harm to another person (even one of those damn bikers) was anathema. When I stopped by the store for a protein bar, I had this incessant urge to compliment people through my mask. I said I liked this dude’s Red Hot Chili Peppers shirt. He and his wife laughed. He said, “Ah, thanks man!”

I tell this story to highlight two key things:

1) I don’t care how many times you’ve heard it before. Every single one of us needs to get good sleep and exercise regularly.

I understand people’s frustration in having this preached at them. These are two simple practices, but they require a series of difficult habit-changes. It’s not as simple as: “I’ll just get better sleep,” or, “I’ll start exercising regularly.”

If it were that easy, we’d all be the best versions of ourselves.

The hardest part of doing either of these is getting over what I call the habit void.

When you’re trying to do something that’s good for you, the habit void is the uncomfortable stretch of time where it just sucks and you’re seeing zero benefit.

The first month at the gym is sweaty, insecure, and exhausting. Once over the habit void, the sixth month at the gym is fluid, exciting, and energizing.

The first week of going to bed earlier is restless, frustrating, and stressful. Once over the habit void, the fourth week of going to bed earlier is relaxing, peaceful, and fueling.

We can justify and make excuses all we want. Whether you like it or not, sleep and exercise are two things you absolutely need. You may see them as asshole-acquaintances. The best solution is to make them your best friends.

Which brings me to #2.

2) If each of us (or at least most of us) got great sleep and regularly exercised, how much better off would the world be?

I know that sounds grandiose. Hear me out.

If another hour of sleep or a single workout can transform me from cranky, easily-irritated, and judgmental…to peaceful, patient, and compassionate…what the hell would society look like if we all took doses of these healthy practices?

I don’t think we’d all hold hands and sing Kumbaya (especially during a pandemic). But I do believe we’d feel a greater sense of community, connection, and genuine care toward one another.

We would feel better. We would be more confident. We would be happier.

These are NOT small things. They bring with them a snowball effect of countless other positive features.

We would be more efficient. We would be more willing to help others. We would be more present.

Maybe this is all a pipe dream. But I don’t think so. We’ll never get everybody to do the things they need to do.

But we can control what we do and make it more accessible and appealing to others. At the very least, we can experience the benefits of healthy practices ourselves and use them to brighten someone’s day.

Even if it’s just one dude and his Red Hot Chili Peppers t-shirt…