It was sophomore year and I’d just transferred to a new high school.

I didn't know anybody.

I had always spent a lot of time wandering around alone and daydreaming but high school didn’t feel like the right place for things like that.

I needed a crew.

I had a cheat code: skate shoes.

Back then you only wore skate shoes if you were a skateboarder, and there weren’t that many of us. The days of the X-Games, Street League, and now the Olympics were far, far away.

Sean and Brandon noticed my shoes and let me eat lunch with them. They were seniors and way cooler than I was but they tolerated me. I was super insecure at the time, and even around other skaters, I was intimidated. They carved out a little space for me but for some reason I never quite felt like I belonged.

One day I bumped into Mike in the quad. I’m not sure how we started talking. Must have been the skate shoe cheat code. Earlier in the week Sean was gleeking on me so I hocked a loogie on him. That didn’t go over so well and I was kind of homeless as far as lunch time went.

Mike said I should come eat lunch with his crew — they had a table in the back of the cafeteria and there was room for me. I didn’t know any of them and I was still incredibly shy and insecure but I said fuck it, it couldn’t be any more awkward than eating lunch alone.

The next day I peeked in. I made sure Mike was there first and then I went on to meet everyone else at the table. That table changed my life. These were my people. The next several years of my life were spent exclusively with people who interacted with our lunch table ecosystem. That table was safety, friendship, belonging, power.

That table helped me feel more like myself. It gave me a safe space to be me.

Mike, if you’re reading this, thank you. I’ll never forget the day you invited me to the table. That one small act of kindness created memories and lifelong friendships that are irreplaceable and forever woven into the fabric of who I am.

So many of us who are trying to make a difference are focused on scale. A bigger platform, more followers, more leverage, as if once we reach a certain threshold we’ll have some special power and our work will be “real.”

But we already have the power to positively affect others. One interaction, person to person, can shape someone’s day, give a boost to someone’s week, even change someone’s life forever. That’s about as real as it gets.

Being a business owner is largely an act of service.

You're responsible for building a support system that allows whatever machine you've created to deliver an amazing experience to your guest.

Of course, for the end-user to have a great experience, every person involved in delivering that experience must be bought into the experience you're trying to create. That buy-in is what makes the work rewarding.

This is important because creating memorable experiences is hard work.

You've probably heard some version of the quote: “Do what you love and you'll never work a day in your life.”

Bullshit.

It's more like: "Do what you love and you'll work harder than you ever have in your life, and you'll be incredibly rewarded by the journey.

Back to the support system.

As the business owner, you provide the foundation for that system. If you don't find your work rewarding, everyone will notice. You won't inspire your team and eventually you'll burn yourself out.

I've been there, and I know I'm not alone.

Many business owners I know have a sacrificial relationship with their business. They constantly give away pieces of their soul to try and keep the machine running.

That's not sustainable energy. The real energy comes from stepping into your power — understanding where you shine and unapologetically cranking up the volume on that channel. Not just because you want to, but because it is the biggest act of service you can provide and no one else can do it quite like you. Not even close.

That energy permeates into every aspect of your organization and everyone can feel it. Even your guests.

If you've been sacrificing yourself for a long time you'll have some initial friction to overcome once you start stepping into your truth but I promise you, on the other side of that friction is beauty.

We need you. Not a watered-down version of you. Not some burnt-out version of you. You. Raw and uncut.

Bring it.

At the beginning of our business journey, I started listening to a bunch of podcasts on entrepreneurship.

Inspiration and motivation were recurring themes that regularly got lumped together and the often painted picture was: If you wait to be inspired or motivated to get something done, you’ll never accomplish anything.

But Inspiration and motivation are completely different animals.

Inspiration is energy - energy that gets embedded in the things you create.

That energy is a cocktail of the vision you have inside you mixed with the things you experience that move your soul.

If we feel inspired, we can pass that energy on to other people through our work. We can never give more than we have, and if we’re not inspired in our work, it will show. It’s this energy that makes an experience memorable.

This is why our favorite restaurants are places that create memorable experiences while others are simply places to get food. The thing they do is the same, but one is completely uninspired.

Enter motivation. Motivation is inspiration's boring cousin. Motivation is simply the drive to get something done. People seem to love to comment on intrinsic vs. extrinsic motivation - how one is fleeting and the other has staying power. Sure. But at the end of the day, neither is enough if you want to create something worth remembering.

That basic restaurant you go to, the one that’s purely functional and entirely unmemorable, whoever opened that place was just as motivated as the person who opened your favorite restaurant, they just weren’t as inspired or didn’t understand how to channel that inspiration.

The ability to inspire and create memorable experiences has nothing to do with money. A fancy build-out alone is not inspiring, a painting that moves our soul doesn’t do so because of the amount of money that was spent on materials.

This is your true competitive advantage in your business, in your projects, in your life. If you can channel your energy, you have the ability to inspire people in a way that only you can do. Create an experience only you can create.

Let’s go!

This space is built to empower people to lean into what makes them, them. To contribute in the way only they can. It's built off the idea that although many people can do what you do, no one can do it how you do it. The idea that you are special.

This idea of being special often gets a bad rap. The fear is if we tell people they're special, they'll feel entitled.

Thus we need to clarify the definition of special.

Being special isn't the same thing as being entitled.
Being special doesn't mean receiving special treatment.
Being special doesn't mean you're any more valuable than someone else.

Being special means you have intrinsic value as a human, or as my childhood neighbor Mr. Rogers said in his 2002 Dartmouth Commencement Address after reading the words to his song "It's You I Like":

"And what this ultimately means, of course, is that you don't ever have to do anything sensational for people to love you."

The emotional connection you create and have the potential to create is one of a kind. You are more than your work. You are more than what people think of you. You are even more than what you might think of yourself in any given moment.

This is what it means to be special.

It's National Suicide Prevention Week. I have no experience with suicide in my life. I do know that when I've had dark times, having people there for me, even when I felt I didn't deserve it, has changed my life.

Check in with your friends and loved ones. Let them know how irreplaceable they are.

From the time we’re young, most institutions we interact with focus on building our brain. The traditional path to adulthood leaves us incredibly “smart.”

So smart we’re able to continually make really bad decisions — decisions that go against the core of who we are, and instead of noticing how they make us feel and correcting them, we can easily rationalize them.

That is the power of our brain.

Like all powerful things it needs checks and balances, something to focus that power — an operator so to speak.

This is where your heart comes in.

But there’s a problem. The institutions we interact with every day don’t focus on building our heart in the same way they focus on building our brain. If at any point in time you’ve suddenly become aware that you feel incredibly capable but also completely lost at the same time, you know what I’m talking about.

This is where many people would insert some sort of “follow your passion” speech. While those are cute and can provide a small burst of energy, they still neglect the ecosystem we’re dealing with. Passion alone is lazy.

We need to engage in activities that make a heart-brain connection. Activities that put both of our most powerful tools to work together. This will look different for everyone. This newsletter is one of those activities for me — the message comes from the heart and my brain is responsible for translating it in a way that can (hopefully) inspire you. It’s the structure, the intended impact, and the thought process that goes along with it that makes this newsletter more than simply a journal.

Our heart points us in the right direction, and our brain navigates the terrain. 

We need both, working together, in that order.

What will you do to build the connection?

I love starting projects but I’m not always the best at finishing them. 

I’m constantly surrounded by projects in various states of incompletion and instead of focusing on finishing one of them, I just keep starting new projects.

This creates the illusion that I’m making real progress but I know it’s just a fancy procrastination mechanism — my brain trying to keep me safe by not sharing things that are very personal to me for fear that people might not like them, and to shelter me from my own disappointment in what I’ve created not living up to what it was supposed to be.

For my fellow serial project starters, I want to offer a few reasons to finish one of those projects, to take something to Z, to share your gifts. 

Here we go:

When we share our gifts with others, we learn more about ourselves. 

Coming up with ideas is pretty fucking easy. Taking an abstract idea and making it exist within the boundaries of reality is hard. You’ve got to tweak it, bend it, and maybe even bend reality a little bit. This is where you really put your fingerprint on your ideas. The process of taking something all the way will help you uncover gifts you never knew you had and understand your idea on a deeper level. Ever notice how after you teach something to someone else, you often understand it better yourself? This is the same effect. 

Sharing our gifts builds bridges of connection. 

Sharing our gifts is like sending out a flare or flying a flag. “This is what I believe!” It is, in essence, revealing who we are. It can be scary but if we never reveal who we are, we’re depriving ourselves of the connection that comes with finding other people who believe what we believe. Stepping into your truth deepens existing connections, plants the seeds for future connections, and weeds the garden of imposters — people and things disguised as true connections that only suck your energy and muffle your voice. 

Sharing our gifts inspires other people to share theirs. 

Sometimes people need to be inspired by someone that they can relate to. Someone who has been where they’ve been. Someone on their level. While the Steve Jobs of the world are often used as the gold standard for what creators and entrepreneurs should be, they are few and far between, and modeling them is toxic. There are people all around you with ideas brewing inside them just waiting to be inspired by someone like you. People can’t be inspired by your gifts if you never share them. 

I’m not saying you have to share everything — some things are sacred and just for you. I'm just saying you have something unique inside you that can make the world a better place, but only if you let it out.

I read. A lot.

I listen to podcasts.

I get newsletters much like the one you’re reading now.

Why?

To be completely honest I’m terrified of dying and often feel an immense pressure of packing as much in as possible.

Gain knowledge. Make progress. Repeat.

No moment wasted. Everything optimized.

I generally enjoy it. At least I think I do.

I’m a curious dude, and my naturally competitive nature pushes me to maximize my energy output and attention. I don’t really casually do anything — I go all in.

Until I inevitably hit a wall.

A wall where picking up a book feels painful, podcasts make me want to smash my phone into tiny pieces, and I have a strong urge to unsubscribe from all my newsletters. A wall where I’d rather do just about anything than listen to one more motherfucker tell me how he has it all figured out.

That’s where I’m at right now.

Let me tell you what I did last week:

I watched about 10 Disney movies, read a handful of kid’s books, doodled with no intention, and went on a few long drives.

Initially this made my brain think I was wasting time, like I should be listening to Impact Theory instead of watching Frozen II. Like every day I read a kids’ book instead of learning a new life-hack as I inch towards death is a day wasted.

But I played forward.

Once I got over the guilt of thinking I should be doing “more”, I was gifted with a wave of relaxation coupled with a slew of new creative ideas, and this feeling of clarity. I felt like I did when I was a kid and used to wander around the playground and daydream about my secret life as a Gundam pilot.

It was a great reminder that my brain needs space to be at its best. That I have more in common with artists than I do high-performing CEOs. That children's stories have all the lessons that adults need to hear. That I like having some free time to dream!

I struggle with a lot of what I write being painfully obvious. Yes, we all need our own unique mix of intentional productivity and free time. It just seems that as we get older that free time often comes with a side serving of guilt. Is it self imposed? Societal pressure? Idolization and modeling of people who do spectacular things but at their core are dysfunctional and probably complete assholes? I don’t know.

Maybe I’m the only one who struggles with feeling like they need to go full-throttle all the time, but if you’re with me, welcome to your virtual support group. We’re giving you permission to try out a few days of no strings attached and see how it goes.

I sometimes get asked what success feels like. Until this pandemic, I couldn’t really tell you.

What happened?

My guess is that all of the excess stress that bubbled to the surface forced some really important conversations both with myself and others, and I’m pleased to announce that I now know what success looks like.

Success to me means letting go of others expectations.

In our business, it means having a vision and feeling empowered to stand behind it. Challenging people instead of pleasing them and when it becomes clear someone’s not on our path, having the freedom to let them go and not see it as a failure or a reflection of your ability as a boss, just for what it is: a mismatch.

Personally, it means spending time creating things I want to create. YouTube is a great example. I’ve been making more videos about things that resonate with my soul — things I hope will help other people in a very real way. Since I’ve started down this path my videos have gotten way fewer views, the algorithm seems to hate them, the small amount of ad revenue I make has shrunk considerably, and I couldn’t be happier.

Sure I could probably make some serious cash and have a much larger audience (i.e. be more successful) if I devoted my whole existence to making coffee videos but that’s not a trade I’m willing to make.

Through all my different explorations I’ve found the most truth by casting out the label and pressure that’s often associated with the role.

I never wanted to be a business owner or entrepreneur (gross) — I just had a vision for what work could feel like.

I never wanted to be a YouTuber — I just wanted to share ideas.

I’m just me.

You’re just you.

Feeling successful is about being true.

I live across the street from a coffee shop. It's not the shop I own. 

Before COVID hit, going across the street to have coffee and read was a huge part of my morning routine. Inevitably, once or twice a week someone would see me and say some version of: 

"You here keeping an eye on the competition?!" 

I never know how to respond to that shit. It's 7 am man. I'm just trying to read. 

I know they're probably just making conversation but it's alarming how much the "us vs. them" sentiment is woven into our society. That somehow everything is a competition. 

There's this underlying feeling that the easiest way to elevate your status is to bring someone else's down. 

As a formerly highly insecure and competitive person, I often defaulted to this mindset in hopes of finding recognition and acceptance. 

All I found was distance. Distance between myself and other people. Distance between myself and my goals. 

It's been a huge undertaking to undo these thought patterns. To focus on competing with myself instead of others, to try and help instead of hinder.

We're all part of an ecosystem that thrives when every part of that ecosystem is healthy. Unlike all the companies involved in the Subprime Mortgage Crisis in 2008, we don't have anyone bail us out of our monetary or mental messes created by acting from this flawed, zero-sum game mentality. 

Last week I found out our friends who own another local coffee shop were moving in right across the street from our newest, largest, and most expensive to build location. A location we just opened two weeks before COVID hit and turned everyone’s business upside down.

My immediate response: "Time to throw some block parties."

I believe everyone has a gift - a unique contribution that only they can make and I think as leaders it’s our responsibility to create environments that help people discover those gifts.

When people can see themselves in their work — when they’re in their sweet spot, everybody benefits.

People get a space to do their best work which makes their experience more fulfilling.

Enthusiastic, engaged employees pass on that energy to other employees, customers, and guests.

It’s not hard to see why this is great for the organization.

So it’s in everyone's best interests if we, employers, can help identify what moves someone's soul. Again, I believe it’s our responsibility. It’s one of the most important things we will do.

It’s also our responsibility to recognize when a person's gifts and highest contribution don’t align with the Mission, Vision, or Values of our organization.

Cultural fit is important to the health of an organization. Bad cultural fits will become toxic, and ultimately unhappy and frustrated at work.

Discouraged employees pass on that negativity to other employees, customers, and guests.

It’s not hard to see why this is problematic for the organization.

It’s important to note that identifying a bad cultural fit is not the same as identifying a bad person. It doesn’t mean you don’t like them, it’s not a mark on their character, and it doesn’t mean you don’t care about their well being.

It’s actually the opposite. It means you value them enough to be open and honest with them so they can find a place where they truly shine. Keeping people in a place where they can’t use their gifts or do their best work is selfish.

We avoid these conversations because they make us feel uncomfortable. We feel scared, ill-equipped, or even guilty because maybe this person has been struggling for a while and we’ve never brought it up before.

But these conversations are important - for the individual, for your team, for you. We don’t all fit in everywhere and that’s ok. It works both ways. Not only are they a bad fit for your organization but your organization is a bad fit for them.

This is written from the perspective of a business owner but this applies to friends and family as well. Get to know the people around you. Be a source of honesty for them. It might feel uncomfortable but sometimes the most important conversations are the ones we don’t want to have.

We’re all individual pieces to a larger puzzle.

Just as any one piece in a puzzle doesn’t connect with every other piece of the puzzle, we also won’t fit in everywhere.

We all have our subcultures and niches we resonate with — places we fit in and feel most like ourselves.

While we might not directly connect with certain people, we are all connected.

A puzzle isn’t complete without all the pieces, and no one piece is more important than another. Each piece works together to create a beautiful picture.

If you're feeling alone or lost it doesn’t mean you have no value or contribution to make, it just means you haven’t found your place in the puzzle yet.

Keep searching. We need you.

It's 11:53 pm the night before this gets published. I spent most of my free time this week making a video and didn't do any meaningful writing.

I made a trade. Writing time for video time.

Could I have carved out time for both of them? Sure. It just required another trade.

I could have spent less time with family and friends, slacked off at work a bit, or cut back on what I ultimately decided on trading: sleep.

I'm not a fan of killing yourself for the grind or the hustle or whatever the fuck they're calling it these days but it's important to note that sometimes we'll need to inconvenience ourselves for the things we care about.

Is it annoying to pick your friend up at 2 am when their car breaks down 20 miles outside of town and they need a ride? Sure. But you're happy to do it, not because they'd do the same for you, but because you care about them and that care outweighs the inconvenience.

Partnerships, friendship, work, your passions projects — none of these exist in a vacuum. They will all require making trades at some point. The trick is not to keep score or look for balance but to be incredibly clear on what is worth making a trade for.

It seems as if the purpose of social media would be to create connection. To share slices of who we are with other people to find common ground, or discover and share new ideas.

The catch is that social media is not designed to create connection but to keep us plugged in.

A never-ending hamster wheel of getting more followers, likes, and shares.

Getting more followers, likes, and shares makes us feel like we’re part of a community, and being part of a community feels good.

So we water down our point of view in hopes of not offending anyone. When hot button issues pop up instead of digesting information, checking in with ourselves, and moving forward in a way that feels true to us, we simply parrot back the loudest voice.

We do these things because it’s nice to fit in and it makes us feel safe. No one can judge us if we don't let them know us. Plus maybe we’ll get some more followers. Maybe more people will like us.

Being left out sucks. But being someone you’re not sucks even more.

To experience true connection with others we must first connect with ourselves.

This requires the courage to be honest with ourselves and then the courage to share that honesty with others. It’s scary. I struggle with it every day. But the times I find the courage to push through the fear of not being accepted always seem to be the places I find the deepest connection.

There's a job to do. It needs to get done. But within that job are infinite possibilities. How we look at those possibilities directly affects what we put into our work and of course, what we get out of it.

When I worked in cafes, I never thought of my job as prepping and shipping units of coffee. If I had, I probably would have been a barista for 6 months instead of 10 years. Every day was an experiment. Here are a few nuggets that made each day interesting:

• Any given morning I was likely the first person someone would interact with outside of their family. I had the opportunity to make that interaction awesome and set the tone for their day.

• Getting someone's drink to them by the time they got to the register instead of waiting for the order to come through. It's a game — if you're on time, you're behind. It made people feel special.

• Buying someone coffee when they're having a shitty day. For less than a tenth of my tips for the day, I could buy someone coffee and brighten their day. (Baristas note: this is different than giving out free coffee, you have to pay to play.)

• I'm naturally shy. Each day gave me the opportunity to experiment socially and build my confidence. No matter how awkward I was feeling, I got a fresh start with a new guest every 30 seconds.

• You can learn a lot in small chunks compounded over time. Pushing past generic greetings and pleasantries opened up a whole new world of learning and exposure to interesting subcultures. I tried to learn something new every day.

The list could go on and on. When I zoom out, it's clear to me that I saw my time behind the counter as an opportunity to spark joy in other people and to push through personal barriers — much more engaging than putting brown water into tiny cups.  

All of these things allowed me to have some autonomy and works towards a bigger purpose while staying in the lane of "doing my job."

Of course, we will all grow out of jobs, have the desire to try different things, and at some point probably have a job that we hate. But if we're clocking in for eight hours, we might as well make it count.

How do you view the work you're doing? What possibilities can you tap into right now to make work more rewarding for yourself and others?

If you've ever had a job you know the importance of taking inventory.

If you don't take inventory you can't order properly, you sell shit you don't actually have, and it makes planning for the future impossible because you never know where you're at.

So you take inventory. It sucks. It feels so extra. But you do it because if you don't, you get fired.

Taking our emotional inventory often feels much the same way. We know we should carve out time to reflect and ask ourselves important questions:

"How do I really feel?"
"Are my actions aligned with my goals?"
"What truly makes my heart sing?"
"Am I doing this for me, or to meet other people's expectations?"
"I'm going somewhere — is it where I want to be going?"

It's easy to ignore taking emotional inventory because we have a little bit more work to finish here, or we want to get ahead on a project there. Maybe we have a pretty solid idea of what the result of sitting with our emotions might be and we don't really want to face it because it feels easier to not.

But just like inventory at our job, if we ignore it, it's going to bite us in the ass at some point and when it does, it's going to hurt way more, and take more time, energy, and effort to correct than it would have if we would have simply gotten ahead of the game.

So take some time out today. Take your emotional inventory. Turn it into a regular thing to be celebrated and not something to be ignored and feared. You deserve it. 

Too often I find myself running away.

Running away from shit I don’t like. Running away from something that’s causing me pain. Running away from something that makes me feel uncomfortable, drained, or scared.

I run and run and run, and never seem to get anywhere.

This is because running away, while sometimes necessary, is only a short term strategy.

Running away provides no direction.

If we spend all our time running away, all we’ll ever think about is what’s behind us — the very thing we are trying to get away from.

A better strategy is to run toward something.

“I hate this job and need to leave.” is a less powerful statement than “I want to work somewhere that values my individual contribution.”

“I need to get away from my current friends.” says less about what you actually want than “I want to be around people who push me and hold me accountable to chase my dreams.”

Framing things in the context of what we do want is more powerful than framing things in the context of what we don’t want.

Once we know what we want, we can use our energy to run toward it. Each day can bring us closer to something we love, not just further from something we hate.

There's no escape from getting it wrong. 

Getting it wrong provides an inflection point for growth if we're willing to step back, recognize our mistakes, and push forward again. 

It often feels like there's safety on the sidelines. That we can spare ourselves the shame of getting it wrong by avoiding things that make us uncomfortable. 

Starting a new journey is intimidating. A personal project, a business, or educating yourself and speaking out against social injustices that are so deeply woven into the fabric of society that it makes you cringe to even think about it. 

While certain journeys are definitely more weighty than others, they all begin in the same place: Taking the first step knowing that sooner or later, you're going to get it wrong. 

What's far worse than getting it wrong is waking up one year, five years, ten years later to discover that you haven't grown at all, that you haven't done anything. 

Skateboarding was where I found my first home. A group of people that accepted me even though I was, well, me. 

Skate culture at the time was a safe haven for misfits. It drew people from all walks of life and even though it was a pain in the ass it was somehow enchanting to get yelled at by jocks, kicked out of places, and be harassed by the police. 

As entertaining as all that was, I do remember being upset about the label that was put on me and my friends: that we were stupid, lazy, and destined for failure. It made me angry. 

Because of this, I used to think I could relate to others who were systemically marginalized.

But there's a difference. I can choose to leave my skateboard at home. The cops gave us shit but our lives weren't in danger. Jocks were just having fun with us but didn't really want to cause any serious harm. Being judged negatively for being a skateboarder is not even on the same planet as dealing with systemic racism.  

This all probably sounds painfully obvious, and it should be. But for a lot of people, including myself at one point, it isn't. There's a cultural disconnect. 

For people who grew up in my shoes, this is where doing the work comes in. Trying to understand as much as we can knowing we will never understand. Being willing to listen to other people's perspectives, take them seriously, and act on them — not simply dismiss them because "It doesn't feel like that for me." Being willing to see what is so easy to ignore.

I am so small, so imperfect, and so ignorant about what needs to happen to start steering the ship in the right direction. So here I am sharing an experience. Owning a mindset I had that was completely wrong in hopes that someone who sees this will be able to share it with someone who can benefit from it.

Today I'm attending a workshop on how to build a strong culture. I imagine a world in which work deepens the connection between us and the things we love. I need tools to further my cause so I seek help.

Today I also have a call helping two passionate business owners build a strong culture of their own. They have big ideas about what a business can be and are intent on bringing their dream to life. They need tools to further their cause so they seek help.

I like to imagine that this continues all the way up and down the spectrum. That those I'm helping are helping others. Those helping me are reaching out for help. An unbroken chain of students and teachers.

Today offers one literal example of this chain but here's the great part:

We don't need to sign up for a formal class to learn.
We don't need a huge platform or following to teach.
We learn just as much helping others as we do seeking help.

But only if we approach each moment with intention.

Every day each of us has the opportunity to be both a student and a teacher. If we don’t embrace both paths, we're selling ourselves and those around us short.

Your good intentions can't inspire someone, give someone hope, or make them more equipped to tackle the challenges they face. 

Only your actions can do that.   

It's recently become clear that the picture of myself I have in my head and the actions I take don't match up. At least not as much as I'd like them to. 

As much as I want people to see me for what I believe, I must accept that they can only judge me based on what I do. 

Finding the courage to act isn't always easy. Putting a flag in the ground means you're going to piss some people off. People who might be close to you. People you value.

But your road is yours to travel, and standing up doesn't mean standing alone. 

You gain the opportunity to find people who feel the same way as you. To inspire others to take action of their own. To help others who need you.

But only if you send the signal. Only if you act.