Aside from some necessary outdoorsy items in Vancouver Island, I haven’t purchased any new clothes since 2019. I shop at Goodwill and the Dollar Store.
Here’s where my money tends to go:
Tech (which are usually business expenses)
I’d love a Tesla as much as the next American. But if I had $1m to get a new car, I’d still probably get a used 2016 Honda Civic. Paid in full.
In short, I don’t care about “living luxuriously.” I don’t have an Instagram. Humbly bragging about my income on this blog is all the dopamine I need.
There’s a piece of advice from Tim Ferriss that’s stayed with me over the years:
For things you use on a daily basis, bite the bullet and pay for high quality.
I don’t count a car in this category, because a new car payment can simply bleed us of money. But this week, I bought a new mattress and a new pair of headphones.
I figured a week of Covid isolation was the perfect time to invest in these things. My mid-grade mattress was super firm and I was waking up several times a month with neck and back pain. My old wired earbuds were itchy and didn’t keep the noise out.
Were these purchases absolutely 100% necessary? No.
But my God am I happy with them.
I melt into this new mattress. I’m wearing these headphones right now. I can’t even hear my fingers type on the keyboard. They keep the world away and I’ve never felt more focused.
The best thing? Both these items will hopefully last me several years. I don’t have to think about them for a while.
The next plan is to buy a new desk and desk chair when I move to NYC. Stay tuned.
I got to ask one of my favorite questions yesterday.
In a session, a client told me he wanted to take more action toward his career. When I asked him what his next steps were, he said he needed to learn more and be better prepared.
I thought, prepared for what? The apocalypse?
“So you’re telling me that you want to get into action, but before you can do that, you need to learn more?” I thought, How much more have you decided you have to learn? On what date will you know enough to start taking action?
But instead, I asked a more direct question:
“If I told you I’d give you and your father each $10,000,000 if you got one customer to pay you for a service in the next week…how would you spend this week?”
His eyes got big and he smiled. “I’d reach out to as many people as I could and offer my services to them. Every day. I wouldn’t care about how many rejections I got because I’d only need one person to work with me.”
“Fuck yeah,” I replied. “So what’s stopping you from doing that now?”
His mouth opened and closed. “You know what, I don’t have a good answer for that.” We laughed.
The power of this question is that it removes the barrier of “I don’t know how.” When so much is on the table, our brains go right toward a version of: I’d do whatever it took.
The action is there. The creativity is there. It’s often just the drive that’s lacking.
When I asked another client that same question last week, she said, “Jesus. Hypothetical money is a powerful motivator.”
So let me ask you:
What’s something you really want in your life right now?
If I told you I’d give you $10 million if you created it this week, how would you spend your time?
Is it possible to be our genuine selves around other people?
That may sound a little woo woo but it’s the question I mulled over yesterday. I connected with a coaching friend and she told me about a lesson from the book Mastery of Love by Don Miguel Ruiz.
In it, he talks about the performance we put on in each of our relationships. Let me explain.
When we’re with another person—friend, partner, family member, colleague, stranger…there’s three versions of us:
Our true, authentic selves.
The version of us we’d like the other person to see—knowingly or unknowingly.
The person they actually see with their own lens.
That happens for both parties. Six people total. This blew my mind.
I’ve always been fascinated by how we can be completely ourselves but in different ways. As in, I’m “myself” when I’m with my mom, my best friend, my clients, etc. But they all get slightly altered versions of me.
I put myself in quotes because I’m beginning to wonder what that word even means. Does it mean comfortable? Does it mean I feel aligned with my words and actions?
It feels like our “true selves” are constantly changing based on our environments and social settings.
Even in my conversation yesterday. She’s a newer coach in our community and we connected over all the lessons she’s been learning as she’s been taking more action.
At no point did I feel like I was putting on a show. But right when she shared this six-people concept, I realized I was on the call trying to be more helpful than usual. It hit me that I logged onto the Zoom thinking, “Be as valuable as you possibly can.”
My takeaway from this?
It can be insightful to ask: Do I want this person to perceiveme in a certain way?Would that feel like I’m putting on a show?
I wrote a blog yesterday about being financially transparent.
One friend commented: “When we talk about money more casually, we can share insights into career moves, upward mobility, investing, debt, etc!! It’s just so helpful to be transparent with others you want to succeed. “
To continue that train, I want to share what I’ve been doing the past two days: my taxes.
I’m having a blast. Here’s why.
This is my first time doing taxes as a business owner. So I hired an accountant. He gave me a to-do list.
Auditing and investigating my 2021 has been wildly insightful and fun. I texted that to my friend and he responded, “Only you would enjoy doing taxes…”
What I love is that it’s a story that’s told through my spending and earning. Going through my account statements and going, Oh yeah, I can’t believe I used to pay for that service!
The income chart makes me laugh. I can remember earning my first $500 in April and feeling like I made it. I remember not sleeping and shaking at my desk in June from anxiety. And I remember the euphoria and peace in September when I finally started making more than my monthly expenses.
I can’t believe how much I spent on bills, coaching, and food. We always know it’s a lot but it’s wild to see it all added up.
I’m pleased with my story. And I’m excited to see how 2022’s unfolds.
There’s this age-old taboo that says we shouldn’t talk about money or ask people about theirs. I think we should step away from that.
But first, why does money make us so uncomfortable?
The number one reason is that it’s an enormous source of comparison. I’ve fallen victim many times to what I call “travel glamor shame.”
That’s when we see our friends—or enemies—in some beautiful foreign country and then we immediately hate ourselves.
How much money a person makes can be hard to dismiss. I say I treat every single human being with the same humor and respect as the next. But the difference between someone making $25,000/year and $250,000/year doesn’t go unnoticed.
And that’s the thing. I don’t think it should go unnoticed. I just think we shouldn’t care.
We can have both. We can talk about the discrepancy of a person’s income without treating them any differently.
I’ve been talking about money frequently with other coaches in my community. How to value our services. How to make more of it. Why it’s not this evil thing.
2021 was the year of building my business. By September, I had gotten it to be highly profitable and sustainable. But the months before that were riddled with uncertainty, doubt, and anxiety.
All that to say: I’ve learned so many lessons about making money that I want to share. But I usually feel bad talking about them because I don’t want to come off as arrogant or like I’m gloating.
What’s funny is, whenever I do share about my finances with other coaches, they tend to find it inspiring. “It makes it seem more real and possible,” one coach told me.
That’s the point.
When I talk about my money, the vibe isn’t, “Look at how cool I am.” It’s, “Hey, I’m an idiot. And if I can do this, you can too if you want!”
I know people who make six figures who either love talking about money or despise it. I know people who make less than $30k who either love talking about money or despise it.
This blog was a tad rambly but I’ll end with this statement.
If we treat money like Voldemort, like this unspeakable thing, I think it just causes more stress and pressure around it.
When I had a job, I always thought it must be pretty challenging to be someone’s boss.
I expected them to…
Be a confident and competent leader.
Express kindness and care toward their employees.
Maintain an organized system.
That’s a lot to do all at once.
I’ve worked in restaurants, at a home remodeling company, and on a farm. I’ve had phenomenal bosses. I’ve had terrible ones.
A good leader can be the difference between dreading going to work and looking forward to it. A strong captain can make us feel safe. They can even become a mentor to us. I still keep in touch with the best bosses I’ve worked with.
The #1 reason people quit their jobs is because of poor leadership. Here’s a graph that paints the picture.
Luckily, I’ve never really experienced any of this. I’ve just had some bosses who had no ability to build connections with employees. It just felt like they were kind of…there. They didn’t light anyone up and it felt like they were easily replaceable.
I’ve learned how to lead from the great bosses I’ve had. While I’ve never hired anyone, I use their lessons on a weekly basis with my team and community. I still remember how they made me feel.
The way things are going, I’ll never have another boss in my lifetime. But I’m quite pleased with my track record.
I’ll end this with a statistic.
Of the highest performing and most fulfilled people in the workforce, 91% of them answered “Yes” to this question:
Do you feel like your boss cares about you as a person?
I played in my second chess tournament this weekend. It didn’t go well.
My first competition was in December. That one went much better.
In typical fashion, I showed up an hour early. I was the first one there. I met the head of the Waldorf Chess Club and we chatted about chess and sandwiches.
The other players piled in and we got sectioned into quads: groups of four. We would play each person in our quad once for a total of three rounds. I took math in college so I put this together quickly.
To spoil the whole thing, I lost all three of my games.
Here’s how each of them went:
Neck and neck until he ruined my pawn structure (weakened my position). Beat me in the endgame because of my bad position.
I tried to be crazy flashy and sacrificed two pieces for a fancy checkmate. I miscalculated and was then just down two pieces.
A super even game that went down to the last few minutes. He was up a pawn and used that to beat me in a King and pawn endgame.
Here’s what I took from all this.
But it is valuable. For many reasons.
After a strong performance in my first tournament, I thought I was hot shit. I needed to be humbled to snap back to reality. Mom’s spaghetti.
As I learned in Brazilian Jiujitsu, being humbled, getting your ass kicked…It makes us kinder and more patient people. It gets us out of our heads. It destroys our egos. Our wellbeing stems not from our success, but our willingness to grow.
Only when our armor is damaged can we begin to make repairs to it. Otherwise we just walk around thinking we’re invincible.
I barely remember the winning moves I made during my first tournament. But the losing moves in this last one are engrained in my psyche. I can envision them right now as I’m typing this.
It’s an unfortunate truth, but losing is the best (only) way to get better at chess. That’s probably true in any endeavor: business, relationships, instruments.
When I meet with my chess coach next, we’ll have plenty to analyze.
The people I played this weekend were much stronger than those I played in December. It was a reminder that I must consistently go against better players.
The first competition pumped me up to improve at chess. It was a Winning is fun! I want to do more of it kind of motivation. This one energized me even more. But this time it’s a Losing is awful! I want to do less of it sort of thing.
The losing will never stop. It’s part of leveling up. It’s out of my control.
The only thing I can control is what these losses mean for me.
But I’m not even close to an expert. And that’s the point.
We don’t need to have more information (or even more skill) than others. Most of the time, the people who are “successful” are just the ones willing to put themselves out there.
Did I just call myself successful? Well, I certainly feel like I’ve had success. But I felt that way when just three people were reading my stuff.
I’ve had blogs with over a thousand unique readers. Some of those posts include my thoughts on death, my trip to Canada, and my move to NYC. I’ve had people I don’t know email me talking about their favorite pieces.
I don’t say this to brag. I say this because I never set out to be a “great writer.” I just wrote one of these almost every day for three years. It took a year and a half for people to really start giving a shit.
We can get really good at things if we have two things…
Consistency and the willingness to be messy.
I can’t even read my earlier writing. Most of it makes me cringe. But if I worried too much about that early on, I wouldn’t have written anything and I wouldn’t have improved.
It’s not sexy advice. But to get good at anything, we just have to do it a lot and be okay with doing it poorly.
We don’t need to read “one more” book. We don’t need another course. We just need more practice.
Keep that up…and maybe you’ll build yourself a mediocre blog like me.
I’ve been working on my book for five months now. Most of that time has consisted of two things.
Interviews and procrastination.
Early on, I was worried I wouldn’t have enough content to write more than a pamphlet. Once I began actually writing and transcribing my recorded conversations, I realized I actually had to cut some folks out. That was a relief.
There were some interviews that, while I’m incredibly grateful for them, just didn’t hit as hard as others. “Trimming the fat” sounds cold. But writing this book felt like less of a chore once I decided to only include chapters that lit me up. I narrowed it down to seven people—including duos.
My last interview was a dream come true. I had a long conversation with James and Anthony Deveney—the hosts of one of my favorite shows, Raiders of the Lost Podcast.
They started their movie podcast in June of 2020, in the middle of quarantine. Since then, they’ve gained half a million followers and have grown arguably the best film podcast to date.
Their story was captivating and inspiring. They were also two of the nicest dudes I’ve ever met.
They took me through their journey of pursuing their dream: being full-time content creators. It’s one thing to see people doing something cool. It’s another thing entirely to hear about what they had to do to get there.
James just quit his full-time job a few months ago once the podcast was able to totally support both of their lives. I’m thrilled to tell their tale.
As for my process of writing, so far it’s looked like this:
Come prepared with strong questions to ask.
Play the interview back with a Google Doc up.
Transcribe the major bits of conversation while playing and pausing the interview.
Use willpower to not immediately edit my writing (i.e. write shitty).
When a story or concept of my own comes to mind, make a note of it in the doc so I can come back and write about it later.
Use the Pomodoro technique for productive time management: 25 minutes on, 5-minute break.
Finish this first run-through before hiring my editor.
Right away, I’ve recognized the necessity of an organized system. If I were winging it every time I sat down at my keyboard, it would be chaos. With this structure, it’s actually pretty easy to write this damn thing.
The only thing getting in my way is initially sitting down to start. It’s the Resistance which gives me all these reasonable-sounding excuses for why I don’t have to start typing just yet.
Luckily, I eventually brush that voice aside and begrudgingly begin writing. Without fail, I enter a flow state in five to ten minutes.
What’s my biggest challenge now?
First, it’s making the time to actually write. I need three to four hours of deep work in order to make meaningful dents in this. Unfortunately (or fortunately), I run a full-time business that’s doing well. That means I have a lot of client calls. Sessions require a ton of mental energy, so I refuse to write for four hours in the morning and then do calls in the afternoon. My brain would be fried.
Second, the debate is creeping in on whether I get a publisher or I just publish it myself. But I’m trying not to focus too much on things that are farther away.
Regarding the first challenge, it’s highly likely that I push back the release date. The plan was my birthday, March 2. The new plan is probably my mom’s birthday, May 5.
Since I don’t have half a million followers like James and Anthony, I doubt anyone will make a fuss about this.
Following the breath. Focusing on each physical sensation. Noticing thoughts and images that appear and vanish.
Within a month of consistently doing three, five, or ten-minute meditations, I felt a shift in my emotional state. It wasn’t that I was less emotional per se, but the default response to my emotions became slowed down and lightened.
Someone does something shitty ➡️ I’m pissed off!
Someone does something shitty ➡️ Sensations of heat and tingling in my neck and face ➡️ Thoughts of me telling this person off ➡️ Noticing that all of that is just in my head ➡️ Deciding not to react in a shitty way.
The second process slowly became a habit.
By adding a simple and short mediation practice to my mornings, the rest of my days were drastically improved. I was kinder, more patient, and more appreciative.
Since I’ve been doing this almost every day for four years, one would expect me to be floating in the lotus position on the cusp of enlightenment.
But instead, I’m just a dude.
Half of my meditations consist of me forgetting I’m meditating. I’ll plan my day, get chaotically lost in thought, or worry about one of a thousand things coming up. Clearing my mind feels impossible.
Because it is impossible.
I now use the Waking Up app for my guided meditations. In it, Sam Harris provides a useful model:
“If someone had a gun to your head and told you not to think about anything for 15 seconds, or they would shoot you…you’d be dead in two seconds. If need be, you could probably keep your hand in fire for that long. But we can’t help but think.”
I hear people bash meditation all the time. “I’m not good at it…My mind is too jumbled…It doesn’t work for me…”
Welcome to the club.
Aside from severe mental health issues, every single person has something to gain by trying some kind of meditation practice. Even if it’s just three minutes of noticing what’s going on around them.
It’s not about doing more; it’s about doing less. Less reacting, more noticing.
My mentor often reminds me of a piece of advice he was given years ago:
“Don’t fit meditation into your life, fit your life into your meditation.”
For me, when I don’t have a ton of time in the morning, meditation is the first thing I skip in my routine. I regret it every time.
Conversely, when I don’t feel like doing it (which is most days) but do it anyway, I’m grateful 100% of the time.
It was a raffle for subscribing to The Hustle, an extraordinary newsletter on the worlds of tech and business. I’m a sucker for those things…
“For each person you refer, you both could win a billion free socks!” Or something like that. My friends often roll their eyes. But look who’s laughing now.
The $1K comes in the form of an Airbnb gift card. This is phenomenal because it feels like I’ve won free experiences, as opposed to the less-sexy prize of $1K in my savings account.
I’d be grateful either way. And this blog is about that ‘g’ word.
Lol jk. It’s about being grateful.
Something happened five minutes after I saw we won. Something I’m embarrassed to share.
I started thinking about all the trips I have planned in 2022 and about how nice it would be to have my lodging paid for. Brooklyn in February, road trip to Florida in April, NYC again in May, European road trip in July…
Then I thought, Ah man…There’s no way $1K is going to cover all of that. If only it were $5K…
I actually thought that. It took five minutes for me to feel like a free $1K wasn’t enough! Am I insane??
I immediately laughed at myself. “Yeah Dill, some people really have it awful. What ever are you going to do?” Silliness.
Unless I’m a sociopath, the point of sharing that is to highlight the human tendency to always want more. That’s why conditional happiness (or the hedonic treadmill) is a dead end.
Conditional happiness: “I will be happy/fulfilled/satisfied once I have or do this thing.”
Then we get whatever that thing is and we are happy…for five minutes. Then we go right back to our default state.
One of my clients got his dream job, his dream car, and is financially set for life. He told me that none of that brings him sustainable fulfillment. Robin Williams was loved by the world, made millions of dollars, and pursued his dreams successfully. And he hung himself. I got free God damn money and got upset it wasn’t more.
It’s up to us to build a default state of gratitude and appreciation.
I’ve decided to forgive The Hustlefor only sending me $1K. Please send your condolences directly to my email.
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.
I had him write out a typical, average day in his life—morning routine, workflow, diet/exercise habits, fun, partner/friend time, evening winddown…
Then he had to answer a question: If you lived this exact day every day, would it allow you to accomplish your goals in six months? A year? Three years?
In other words: If you change nothing about the way you live your life, will you get to where you want to go?
He gave me an image for it. He told me it’s like his life is a garden. “I know what plants I want to thrive in my garden. Are the seeds I’m planting and leaves I’m watering today going to grow those plants?”
“Not even close,” he said.
“Awesome,” I replied. “What would need to change? Where are the discrepancies?”
We talked about him putting himself out there more socially, delegating more responsibilities at work, and spending more time on side projects and hobbies.
He committed to going to an event: a meetup or a swing dance club, to hiring out more roles, and to dedicating an hour a week to something non-work-related.
A simple plan was made. But it all came from the question…
If you change nothing about the way you live your life, will you get to where you want to go?
Yesterday, my mom took me and my uncle to a Washington Football game.
The only sports I care for are MMA and soccer, but I always say yes to a live sporting event for three reasons:
I’ll enjoy any event if I’m with people I care about.
It’s always fascinating to see people who are at the highest level perform (in this case, NFL players).
The people-watching is golden.
Today, I want to talk about that third one.
Growing up, football was my favorite sport (sorry, Bow Wow). Then around high school or college, I noticed something that turned me away from it.
People truly treat it like a religion.
Don’t get me wrong, I love how a sport can bring people together and evoke powerful emotion in millions of people. I enjoy listening to folks passionate about a sport discuss the business and inner workings of what makes the game tick. I enjoy the roars of crowds at games like the one I went to yesterday. Depending on the UFC bout, you can find me standing and screaming at the TV.
But what leaves a sour taste in my mouth is hatred—disgust for other players or fans (i.e. human beings) because of the jersey they’re wearing.
I’m not saying every single football fan is filled with rage, but it’s not uncommon.
When I was in high school, I would go see my team play against our rivals. I despised them. I wanted them to lose every game. I was convinced I didn’t like them as people without ever speaking to a single player.
For no other reason than the arbitrary fact that I attended my school. If circumstance led me to attend the rival school, I would’ve felt the same about my school. If I grew up in another state, I wouldn’t have even known either of these high schools existed.
Thus the religious context comes into play. When I see babies or toddlers with Steelers jerseys on, I doubt those kids chose to be Steelers fans. Likewise, if we’re born into a Muslim or Hindu family, we’re unlikely to be raised as Christians.
At the game yesterday, I saw fans flipping other fans off, telling them to “stop fucking talking,” and ironically clapping in their direction when their team did something good. There was an essence of mob mentality, meaning I saw people do things they would never do if they were in a living room with just one opposing fan.
There was no genocide, but in what other contexts do we act this aggressively toward other people?
I’m probably being overly dramatic. I just think it’s odd to see people feel so identified with a group of people they’ve never met. And it’s not even that group of people; it’s the shirts they’re wearing.
This blog likely triggered a few football fans. Apologies.
This blog won’t be much different than the one I wrote last year on how I read 64 books in 2020. Well…the difference is about six books.
In my coaching conversations, I’ve heard many people say they want to work on their reading habit.
Let’s start with that last word.
1) I make a habit out of it. (i.e. I read every day.)
Even if it’s just two pages.
In a session yesterday, my client said, “.1 is more than 0.”
Something is better than nothing. Let’s put that into perspective.
If we read 10 pages a day, every day for a year, that’s 3,650 pages.
That means we could read Infinite Jest, Moby Dick, five 200-page novels, five 100-page stories…and still have 408 pages left.
I like reading for 10-30 minutes as part of my morning routine. Sometimes I’ll read as I wind down before bed.
Not everybody has the luxury of working for themselves like I do. People have jobs and families. But I find it hard to believe a person never has ten minutes to themselves for a bit of reading.
In short, it’s about consistency, not speed. I’m a wildly slow reader. Reading practically every day compensates for that.
2) I don’t read shit I don’t like.
If continuing to read something feels more like a chore or an obligation, I put it down.
I’m not saying other people should do this. I have friends who feel accomplished when they stick with dense and challenging reads all the way through. That’s great.
But personally, that’s not why I read. I want to enjoy myself. I’m not in school anymore and I’m not looking to challenge my brain. I want to be entertained, to be intrigued, and to learn things I can use in the real world.
Time reading something I don’t like is time away from something I could possibly love.
3) I keep book notes.
In my Notes app, I keep simple, bulleted takeaways from what I read.
I try to put them in my own words to make it easier for me to remember and apply them.
I’m not certain this allows me to read more, but it definitely makes me feel more engaged with what I’m reading. It also allows me to go back a year from now and revisit what I got out of a book.
4) I log what I read on GoodReads.
To anyone who cares about a reading habit, I strongly encourage making a GoodReads account.
There, one can…
• set reading goals • see what their friends are reading/have read • get recommended new books • keep track of everything they’ve read
Back in October, I visited a few coaching friends in Vancouver Island, meeting them in person for the first time.
While at one friend’s house, we were discussing the things we felt incredibly grateful for. The same thought popped into my head that always does when I ponder what I appreciate most: my tribe of friends, family, and colleagues.
But this time, I had an insight.
Rather than vaguely trying to express this more to the people in my world, I decided I would be as intentional as possible.
I would craft hand-written letters to those who matter most. I would thank them and explain as best I could why they mean so much to me. Then, I would read the letter to them.
I’m not even close to totally completing this task (which I think is a good sign). But I have done several and would like to share what I’ve learned.
1) Expressing gratitude is euphoric.
Let’s get the selfish stuff out first.
Anyone who’s ever done a metta (loving-kindness) meditation knows the immediate rush of joy that comes from truly wishing someone well. We imagine someone we love and we picture them being free from harm and fear. We envision them being totally fulfilled. We see them laughing with the people they love.
This felt more impactful because I was sitting five feet from each person I read a letter to.
I could see their smiles and tears. I got to hug them afterward. I got to hear them stumble to find words that match the moment.
The idea of the exercise is to leave nothing up to the imagination. “Here are the specific reasons why I love you.”
Once that message gets across, the powerful connections I had with each person felt twice as strong.
2) This exercise is the easiest thing to do that brings life-changing results. Low input; very high output.
That sounds kind of businessy. Let me explain.
Each letter takes about 20 minutes to write. I type it out in a Google Doc first. This only takes about five to ten minutes because it’s effortless to write words that are sincere.
Then it takes another ten minutes for me to put pen to paper and transcribe the Doc.
The next time I would see the person, I would: tell them what I did, grab the paper as they panicked, and start reading it aloud.
In less than 40 seconds, our relationship would become wildly stronger.
I even gave this as a Christmas gift to my aunt and uncle. I have no idea if that’s just a cop-out from getting a “real” gift. But they both absolutely loved it so I think I’m off the hook.
3) There are a lot of things we keep to ourselves.
Here’s what I mean.
I’m lucky to have candid and loving relationships with my friends, family, and colleagues. But no matter how open and communicative we are with one another, there will always be thoughts and emotions we feel that the other person isn’t 100% aware of.
That’s also why I suggest doing a feedback exercise with those close to us. It paints a clearer picture of the lens our friends use to look at us.
We can let our actions tell the story. That’s a lovely thing.
But we can also remove the middle-man and get right at the heart of things. I’ll end with an example.
I wrote one of these letters to my dad.
In it, I told him what he did that meant the world to me. Last year, when I decided to not go back to school, quit my full-time job, and start my own business, I thought he’d be furious.
I was out front of my mom’s house, pacing on the sidewalk, when he told me on the phone I had his full-fledged support.
When I relayed this to him in my letter, he had no idea about the impact of that moment.
All this to say: We can always express our love and admiration for people more than we normally do. There’s always more to know.
I highly encourage anyone reading this to write just one letter to someone they appreciate. Tell them why they’re loved. Tell them what they mean. Tell them how much they’re needed.