That’s the cliche part. However I have a secret theory on why imagination works the way it does, why it’s a powerful and sticky force, and therefore why I think analogue will always stick around.

I stumbled on this insight playing a game of chess years ago. I remember the game was close, it was tense, it felt interesting, engaging, expansive. We notated the moves so we could go back and analyze a position if we wanted, and the game only lasted 28 moves.

Wait, 28? That means I only played 14 moves. That can’t be right, this game felt like it’s own world while I played, it was epic. My experience of the game felt way bigger than it actually was. And that was curious to me.

The insight is this: the game felt bigger to me, because it was bigger to me. For every move I made, I considered 2 or 3 or 5 other options. Then for each of those considerations I wondered what my opponent would do. If he moved here then I could do this or this, no that won’t work. What if I did this instead, then he might move here and I could counter with that. No no, he would take my piece in that case, I can’t do that. Or COULD I?

Every single move was a spiral of options, possibilities, that I considered and tinkered with internally. I played way more chess in my head than was represented on the board. That’s why it FELT like a much bigger experience. Because it actually was.

However, this isn’t a guaranteed trait of analogue. The magic is choice. Imagination is in the possibility. The things that aren’t yet, but could be. This is the code line that activates the super computer in your head. Choice. Options.

If you do a basic study of game design, you’ll see this as a recurring truism. Interesting player choice is THE THING that makes a good game. To break that down even further, the player needs a real choice, in other words a game can’t be a series of obvious decisions. Tic-tac-toe becomes boring when you realize there’s a perfect set of X’s or O’s: the first mover can always win.

Additionally the choice can’t be so opaque the player doesn’t understand the consequences. If I can’t imagine the short to long term implication of my actions, there’s no consideration needed. I may as well play randomly, at which point it’s not a game, it’s an activity.

The sweet spot is a series of interesting choices that aren’t obvious, I can IMAGINE the potential outcomes and meaningfully choose different things. But not so non-obvious I CAN’T imagine any outcomes so I just shuffle some pieces around like I’m blindly fumbling in the dark.

But I don’t think this principle applies only to games. Stories follow a similar structure, with perhaps some more nuance. I argue that a good story is also about interesting choices.

A story is boring when it’s predictable. I think the nuance is, the reader (or viewer) isn’t given interesting choices. The characters are given interesting choices, and the reader is given the opportunity to engage. They can imagine what the character would do when presented with an interesting choice, and consider the decision they made after. I’ll try and show you why the nuance matters.

One of my favorite movie going experiences of all time was watching Toy Story 3 in theaters. Warning: mild spoilers.

Woody, Buzz and crew find themselves at the climax of the movie in a dump yard, slowly slipping down a quicksand of trash towards an incinerator.

Now, you may be asking, “What’s the choice here?” The toys are stuck, the odds are insurmountable. They can’t do anything, right?

The interesting choice here, at this specific moment, is: “What do you do in the face of death?”

Do they keep crawling up the quagmire, refusing to give up until the very end? Do they give in to depression? Do they become hysterical? I think you could imagine at least a small list of how someone, or perhaps specifically Woody and the other characters, would respond in this situation. Because the toys are well developed characters, you can imagine, I’m sure, multiple different possibilities for each different toy. However, the toys make the choice to hold each others hand and go through whatever comes together (which is a running theme in the Toy Story series.)

But once that moment passed, and they made their choice, as the viewer my response was, “Wait, that can’t be the choice. They can’t die here, right?” I tried to imagine what was going to happen sitting in the theaters on that first viewing. And I couldn’t. And that was interesting. In stories I love trying to imagine what could happen, and then being wrong, but it still feeling right. The story isn’t obvious, it’s textured with a rich imagination space.

I won’t spoil how this scene ends, other then they do claw their way out of the jaws of defeat, and it’s perfect. (Because of course they can’t die. We have a franchise to continue!). When the scene ended, I thought, “Ah, I could have imagined that, but I didn’t. What a great story.”

There’s lots of directions I could run with this, talking about deus ex machina, or Chekov’s gun and how those fit into my little theory, but I’ll end with this:

Imagination is the art of possibility. Good art, whether it be a board game or story (or otherwise!) invites participation through interesting choices. And this participation (can, when done well) create something that’s much bigger, more expansive, than the thing itself.

As long as our brains can imagine things, stories and board games giving us interesting choices will always be able to compete with the AAA video games and youtube shorts.

The most recent time I visited her she kept calling me “Alex,” my brothers name (her other uncle). Her mom (my sister) insisted she knew my name, and tried to correct her, but Livy kept calling me by the wrong name. When pressed, she finally said my brothers name was easier to say, so she decided to just call me by that. We’re both uncles, close enough, right? (Why “Alex” is easier than “Evan” I’m still perplexed by)

As the good uncle I am I started calling Livy by her brothers name, “Zeke” (short for Ezekiel). She got frustrated at first. “That’s not my name,” she said, then quickly realized what was happening, and a sly smile on spread her face. She got the joke, she’s a smart cookie. She started calling me uncle Evan after that (for now).

Livy just met my Aunt (her great Aunt?) for the first time. Livy demonstrated she could say “Tracy,” but then proceeded to say “Shishi” instead. Again, when pressed, she just said it was easier. To rectify the situation Livy approached her Aunt Tracy and simply asked her, “Can I call you Shishi?” which Aunt Tracy thought was incredibly cute, and said, “Yes please.”

The Brevity Law (originally called Zipf's law of abbreviation, some irony there) states that the more frequently a word is used, the shorter the word tends to be.

The most common words in the english language are: the, be, of, and, to, a. About as short as a word can get. The law applies to both written communication and also the spoken word. (Some studies show this rule even applies to animal communication. Fascinating.)

This isn’t too ground breaking, right? Or at least it intuitively makes sense. We tend towards efficiency, the path of least resistance. From infants, like my niece, we are wired towards the efficient path, including with language. Why say “Tracy,” when “Shishi” will do?

The more we use words as a person and as a society, the more likely that word will get shortened, be made more efficient. This law doesn’t just apply to how often a word is used by percentage. It also applies to how much a word has been used over time. Or perhaps to simplify: the more total surface area of use a word has, the more efficient it will be made. Like a stone monument worn down through wind and rain, the softer stone wearing away and the stronger stuff lingering.

This happens with phrases too. I’m sure you’ve heard the phrase, “Speak of the devil.” Did you know this isn’t the whole phrase? Which is: “Speak of the devil and he shall appear.”

Over time, people understood the meaning, and it become less necessary to say the whole phrase. So it was shortened, unconsciously by millions of people over time, to the most efficient amount of words to communicate the meaning without losing the meaning.

How about “Scot-free?” This originated from a line in the Shakespeare story, Macbeth: “we have Scotched the snake, not killed it.” Scotch, meaning “scratch,” in Shakespearean. Over time “Scotch,” shortened to “Scot.” and “Free” was added to shorten the rest of the meaning: “There should have been bad consequences, but were escaped without a scratch.”

OK, great. What does this have to do with story telling?

A story should show situations, dialogue, and characters in a way that seems real and truthful, despite those things are, literally, a fiction.

Using the “lie” of a made-up story to show underlying truths is the great tool of story. In order stay in a story and not be “pulled out,” a reader needs to accept that the story matches their own experience of how the world works on some fundamental level.

This truism of story telling is often called Verisimilitude.

How we use the made up names and terms and language in our story have to also abide by verisimilitude.

Epic fantasy stories have a certain reputation for long, complicated, made up names for cities and characters and places. Would people really use these long names in common practice? After considering the Brevity Law, probably not.

I think some interesting questions to ask as you write and build a story are things like:

Is this old?

Is it culturally significant?

Is it common?

Do people talk about this all the time?

If the answers are “yes,” than perhaps a good follow-up question could be: “How would people shorten this word/phrase/name over time? What nicknames and short-hand would people produce?” How would the Brevity Law wear down the words so only the most basic and true meaning remains?

That’s not to say don’t also create the original long complicated name. But if you have the original and show how people interact with it, shorten it, make it more efficient to communicate with each other, that shows movement and history. It shows a living, dynamic, cultural ecosystem. It shows you have real people and real society doing what they really do in real life. It adds a little spice of verisimilitude into the concoction that is your story.

The reverse is also true. If something is secret, if it is rarely talked about, if it is largely unknown, perhaps keep the long complicated name that’s hard to pronounce.

It’s an interesting tool in the writer’s tool belt to communicate history and texture and meaning. What do you think?

We all have greater wisdom inside of us than we think we do, so just to hop straight into it, this is a practice that’s helped me unlock the right answers to whatever I feel stuck on, whether it’s a fight with a loved one, the next project to focus on, or simply how to have a productive day.

It’s all some variation of asking yourself, “What would X person do at this moment?”

This is a short list of who I think about, and versions I’ve seen come up over and over, but certainly not exhaustive.

1. “What would my 80-year-old self tell me to do right now?”

This is a great question to ask if you feel you might need a broader perspective on a situation. I find if my wife and I are in an argument and I take a beat to ask this question, and Evan at 80 comes onto the scene, he says, “Look at how beautiful and young she is. I wish I could be there to hold her and experience our younger years together again. Why are you wasting your time fighting? Go over and hold that woman! Talk about meaningful things like what you want the next 10 years to look like. Not ‘if I said what I thought you said, and my reaction to your reaction to my reaction…’”

My 80-year-old self also tends to want me to start things today. He usually says, “One of my regrets is waiting. If I didn’t wait 10 years to start writing that book, I could have written 10 years more worth of books!”

2. “What would I coach myself to do right now?”

I, and I’m assuming you, really like thinking about what we think other people should do. We’re so good at it! If only more people would take our advice, right?

But we, and especially I, don’t tend to turn that super-power inward as often as we should, perhaps. I’ve been practicing this one more and more, but if I simply imagine I’m not myself, and I’m giving advice to someone else in my situation, and I simply follow that advice, my days are much more life-giving and productive.

3. “What would (insert smart person you follow and respect) say to me?”

I’ve often felt stuck and taken the time to write an email to someone I respect who has a certain skill-set, or who is farther along than me in an area I want to improve in, to ask for advice.

And I’ve found if I take the time to read that email, and imagine what they would say in response, the answer has actually been fairly obvious.

I used to send these emails without too much introspective when I was younger, but the older I get, the more and more I delete these emails after some thought and have a clear path forward.

I noticed many people use one of these variations. This has been interesting to me to observe and practice. Often we have a lot more wisdom locked up inside of us that goes unused. These are just a couple of tactics to get out of our own way and unlock what we already know.

I normally score in the 90-100% range on my apple watch for my sleep so I thought I’d include my top practices for the best sleep. (and I only don’t score 100% if I don’t follow 1 or more of these 5 things).

And these ARE listed in order of importance, 1 being the most impactful.

Bonus Tip #1: Track your sleep. This is really the tip to rule them all. I won’t count this as an actual tip because it doesn’t directly affect sleep. But it truly is eye opening to see what things affect your sleep and to what level. Each person has their own unique quarks. Something that works for one person might not work for another, and data and experimentation is the only way to know for sure what works for you.

Bonus Tip #2: Heart rate is king. The best metric to look at (and most sleep tracking apps prioritize) is your heart rate. It’s the #1 indication your body is shutting down and resting properly. Most of these tips work because they help your heart slow down or reduce activities that speed your BPM up artificially.

1. Don’t drink alcohol, or if you do, as far away from bed as possible. Most people think, because alcohol is a depressant, it serves as a calming function on the body. But in actuality alcohol increases your heart rate quite a bit, and stops your body from shutting down at night. Hangovers are primarily a factor of bad sleep.

2. Eat your last meal as early in the day as possible. Food in your stomach causes your heart to pump extra blood to the stomach to do its digestive thing. This causes your heart rate to go up until all that food is processed. This is especially true if you have a carb heavy diet that spikes your insulin. I can usually get away with a small protein heavy snack close to bed, but not much else. If you do intermittent fasting consider dinner the meal you skip (most people skip breakfast). I try and eat my last meal by 5pm at the absolute latest if I get dinner with someone, but my ideal time is 2pm. Feeling hungry 1-2 hours before bed is a good indication for me I’m eating at the right time and my stomach won’t be digesting anything (and raising my heart rate) while I sleep.

3. If you want to supercharge your sleep take a hot shower, as hot as you can stand without burning yourself 60-90 minutes before bed. Your body associates cooling down with shutting down. Heating your body up causes it to start up it’s cool down processes so counterintuitively, heating yourself up before bed causes your body to go into shutdown mode. And of course the inverse is true. If you want to wake up taking a cold shower causes your body to go into heat-up mode, causing a greater sense of wakefulness.

4. Watch the sunrise and sunset outside. I got this from Andrew Huberman, a neuroscientist who posts a lot of great content on youtube. He talks about this a lot, but the reason why this works is our body, just like most of the animal kingdom, is very attuned to the sun. Having triggers for your brain in both the morning and evening to tell your brain “The sun is rising” and “The sun is setting” tells your body it’s time to wake up or time to shut down respectively. The sunrise and sunset specifically aren’t necessary, but our brain can recognize the different light waves the sun makes in the morning and evening, so the closer you can view those events, the better. 3-10 minutes is about all it takes for a minimum effective dose, the cloudier it is, the longer, the clearer the sky, the shorter.

5. Hydrate well on the front end of the day so you can stop drinking liquids 3 or more hours before bed (this pairs nicely with tip #1). This stops you from waking up in the middle of the night (which often happens subconsciously ). It’s both important to hydrate well on the front end of the day, because hydration makes it easier for your heart to do its thing, and also to stop before bed so your bladder isn’t working when your body should be sleeping.

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Would you be happier if you were richer?

The answer to that question is: probably, to a point. Previous studies have found that as people make more money, they do become happier. However, this happiness boost from money fades off at about $75,000/year.

Or it did. I’m sure that number would be higher now if studied again given inflation. But even back then that number was by no means a complete picture. $75,000/year means vastly different things depending on where you live.

If you lived in NYC or LA on $75,000 you were below the poverty line. You were comfortably middle class in a small to mid-sized city in the South East on that same salary.

So it’s not an absolute dollar amount that matters. But what does?

Choice and control. How dependent are you on other people and how much agency do you have over your time?

For me personally, the most unhappy I’ve ever been is when I’ve felt stuck. I’m a fairly stoic, content person. But I’ve worked at desk jobs I didn’t like and felt I couldn’t leave which gave me chest pain and anxiety. And they were pretty cushy jobs. Not hard, I didn’t have a bad boss, co-workers were fine, made decent money. I just felt stuck, not in control, like I didn’t have a choice.

Achieving a certain amount of money or cash flow can give you that control over your life. You don’t have to work at something or for someone you dislike just because you need it. You can pursue purpose-filled work only you could do.

However, that’s only true if you have enough at the end of the month to give you more choice and control. This is why “absolute income” is not a complete picture. The cost of living is higher in certain parts of the country and lower in others, so the same amount of money doesn’t buy you the same choice and control.

The irony and danger of money is buying more stuff that adds drag to your life, not freedom. And every new thing can unnecessarily reduce what stays in your bank account. Even more insidious, every new thing you buy and add to your life creates a tiny fractional complexity. It is one more thing you need to clean/organize/consider/maintain. It takes physical care and takes up mental bandwidth. But as these things add up and accumulate over time, they turn into a complex life that distracts from what you could do with your life. Now you’re spending hours as a caretaker of your own estate instead of time that could be spent as an active agent in the world.

Additionally, if you aren’t “there” yet in terms of choice and control, a focus on purchasing things can keep you stuck where you are longer. Or indefinitely.

Similarly, if, as you earn money, you spend more money at a similar rate, you really aren’t advancing yourself in any way. The more you have stuff that requires a certain income level, the more chained you are to that income level. A “rich” person with a mansion that is at the top end of their means can ironically be in just a dead-end stressful position as a Mcdonald’s worker. Neither feels like they have a choice to leave. This is basically the premise of the book “Rich Dad Poor Dad.”

In so far as money can earn you choice and control, I think it can buy happiness. But beware of the dark side of building yourself a new prison of things and lifestyle.

The main litmus test for all of this is: how much of your time do you own? Our only non-renewable resource in this world is time. What does it matter if you make a lot of money but work an 80-hour week most of the year? Or… a 40-hour week? That might hit a little harder.

Don’t get me wrong. I’m not anti-work. On the contrary, if you read my last post, I’m very pro-work. Hard work with long hours. But work on your terms building something towards your big thing in this world.

My wife and I left everything behind and left on a 6-month road trip, living all over the US (mostly out west). This is still an experiment for us, and I hope to learn a lot, but so far not having much “stuff” hasn’t impacted my life or happiness. It’s put the things that actually matter to me in focus. And we can do this because we’ve focused on earning our time back, and we can spend it working on what we want, where we want, when we want.

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Brandon Sanderson is one of my favorite authors, though not because any of his books are one of my favorites. Don’t get me wrong, I think he’s a good writer (I’d recommend checking out Mistborn if you aren’t familiar with Sanderson’s work), but that isn’t why he’s my favorite author.

There’s a myriad of reasons such as his unprecedented community engagement and free writing resources, but the main reason I continue to follow him is his work ethic. If you don’t know, he launched the most successful Kickstarter of all time last year, raising a staggering $41 Million in 30 days.

There are certainly many factors that led to this success, such as the trust and community he’s built up over the years. But his previous Kickstarter “only” raised $6 Million (obviously still a great success). What caused his sequel fundraising campaign to nearly 10x?

The “X” factor I believe was the (quite literally) unbelievable amount of work he put in. The premise of the Kickstarter campaign: he wrote 5 EXTRA full-length novels during the pandemic. I emphasize extra because the man was previously infamous as a prolific writer and wrote these novels on top of his already break-neck release schedule.

It was so audacious it felt like magic.

How did he do this? To use his own words, Brandon Sanderson writes like an accountant. He shows up, clocks in, and puts in the work. Something that is perhaps uncommon in the creative space that’s filled with “muses” and “writers’ block.” And during the pandemic when everyone was shut inside, he just did more of that accountant work than anyone reasonably would.

This is the simple truth: great things take hard work. And hard work isn’t such a mystery, it simply means putting in the time and doing the thing for an unreasonable amount of time.

Malcolm Gladwell popularized the idea that it takes 10,000 hours to become a master (which is about 3 hours a day for 9 years) in his book Outliers. He found that talent was not a shortcut or a predictor and that lack of talent was not a hindrance. You just have to put in the time.

Mr. Beast, the uber-viral youtube creator, has pushed this idea further and asks himself the question, “What if I put in 100,000 hours?”

This is something I keep coming back to for myself. How can I orient my life and remove distractions so I can put in the time?

Two of my favorite proverbs sum this up for me:

“Where there are no oxen, the manger is clean, but abundant crops come by the strength of the ox” -Hebrew Proverb

This is (in my mind) an ancient tongue-in-cheek way to say: if you don’t put in the work your life is clean easy, but if you want to make something in this world, you gotta shovel the shit out of that manger every day.

and

“The best time to plant a tree was 20 years ago. The second best time is now.” -Chinese Proverb

If you have something you want to do in this world, someone you want to be, you have to put in the work. And to be significant it needs to be 10x more time (or more) than everyone around you. It’s a long road and the best time to start is now.

The good news/bad news is we live in a world where distraction is easy. The bad news is to orient your life in a way to avoid distraction and put in the time can be hard. The battle to stay focused is real.

The good (but unsexy) news is most people lose this battle, and if you can be the outlier who puts in the unreasonable amount of time, 10x or 100x others, you can wield magic too.

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I was reading a newsletter from one of my favorite creators, a board game designer, and publisher, who talked about a recent experiment he ran creating a product many of his fans had asked for. And almost no one bought it.

This reminded me of the famous quote from Henry Ford, “If I asked people what they want, they would have said faster horses.”

I spent a lot of time thinking about product design in my old company Tokyn.

One of the core tenants of product design is: don’t take direct solutions from your users. Your job is to hear people’s feedback and understand the underlying problem. People often are bad at coming up with a solution, but they are really good at talking about their problems. Which Henry Ford understood over a century ago.

People wanted to go faster, and all they knew was horses. His product solved the pain point, but not the recommended solution.

Product design follows this loop. Find a pain point → try to solve pain point → test with users → learn your solution kind of sucks → iterate → test with users → it sucks a little less → iterate, and on and on forever. At some point in there, you have a product that sucks little enough you can launch into the world, but the iterative process never stops.

What does product design have to do with purpose?

When I think of purpose, I think, “What do I want to build in this world that has a meaningful impact?” And even more personally, “Who do I want to become to have a meaningful impact?”

Our life and our work are products: things we want to impact others around us in meaningful ways. And what we do and who we are doesn’t just need to be meaningful to others, it needs to be meaningful to ourselves (otherwise why would we be doing it?) therefore we are also consumers of that product.

And we have the opportunity to impact the design.

Or put more bluntly, we’ll have a bad product of our life if we don’t intentionally test with ourselves and others to learn, and iterate.

You’ve probably heard this referred to as different flavors, something like “Lifestyle design.” I think what’s often missed in the conversation is that, in a product design cycle, BOTH the designer and the consumer are wrong in the beginning. It takes testing something in the real world and it takes iteration to arrive at a product that doesn’t suck.

Writers know this: your first draft always sucks.

Game designers know this: your first prototype is shit.

Product designers know this: people never use your thing the way you think they will on the first iteration.

Movie and TV studios use test audiences.

But I think most people have an idea of what some big thing they want to do is and are waiting for this perfect moment when they are free to do it. However, if it isn’t something you’ve tested, it’s only your first iteration, your first draft, your first prototype, it’s probably actually going to suck and it won’t live up to the ideal you have in your head.

So my caution is: the longer you wait to try, the longer you’re delaying those first cycles of it not being that great. Or even worse, you realize it’s the wrong thing and have a (insert your fraction here) life crisis.

Here’s an example of how I’m doing this:

I like having 1 on 1 conversations. Put me in a room full of people I don’t know and I will last about 15 minutes before I peace out. Get me in a conversation with any 1 person we can have an enjoyable, meaningful conversation for an hour.

I've always loved interview-style podcasts, thought I’d enjoy trying it myself, get to meet interesting people and uncover interesting insights for others along the way.

Before I started Tokyn, I experimented with interviewing publishers in the board game space about new games they released. Pretty quickly I realized I hated it. I realized I didn’t like this iteration because I was more covering new information like a journalist, not really as a conversation.

A couple of years later I tried again interviewing real estate investors. The second time around I liked it! I had great conversations, met great people, but realized I wasn’t doing anything new. There’s A LOT of real estate content out there. And there were a lot of people I wanted to talk to but wouldn’t quite fit in the box I put myself.

My next iteration is a podcast focused on interviewing people on how they successfully found creative freedom: meaning how they orient their life in such a way they could meaningfully focus on a craft and build cool things in the world.

You’re probably smarter than me, but I never seem to get it right on the first try. But I get closer with each iteration.