Honing Your Craft

I don’t feel much like writing today. Which makes it all the more important that I sit down and bang on my keyboard.

Discipline matters more than creativity, inspiration, or motivation.

Especially if your goal is mastery.

When you’re just starting out – regardless what your craft – getting started is often the most difficult part.

As you mature in your craft and begin to develop some actual skill, starting gets easier. But sticking with it can be a challenge.

Once you’ve developed some level of mastery, it’s not necessarily getting started or sticking with it that you’ll have trouble with. No.

Once you get to a certain level, it’s far more likely that you’ll use “your standard” as an excuse for consistently working on your craft.

“You should not attempt anything unless you can do great work,” the voice of Resistance teases.

But that’s not how ideas transform into great work.

If you truly want to hone your craft, set aside time every single day.

Do not allow yourself to develop the bad habit of believing your own press. No matter how good you get, you still need practice to stay fresh.

Even if that means some off days. Even if that means missing your mark. And even if that means starting back over as a beginner in order to reinvent yourself all over again.

On the path to true mastery, discipline matters more than almost everything – including talent.

As they say, “The world is run by people who show up.”

The 400th Thanksgiving

It’s incredible to think just how far we’ve come in the past 400 years.

The good, the bad, and the ugly.

A bunch of incensed Pilgrims boarded a ship to a new world, seeking respite from an overbearing church and state. They made their sojourn to Zion.

Many died. Those who didn’t nearly starved to death.

But those who survived discovered the bedrock upon which to build a new civilization: freedom (and property rights).

You’ve got to think those early colonists understood the price of their newfound freedom.

It cost many their lives. But even those who outlived famine-like conditions, disease, high infant mortality, brutal weather, bouts with wildlife, and countless other challenging conditions…they all paid their pound of flesh for their freedom.

During that chapter of the American experiment, freedom didn’t equal material comfort.

It was impossible to escape from the reality of responsibility.

Even while the early colonists experimented with commune-style living and production, if enough people didn’t produce, everyone would starve.

How’s that for responsibility staring you in the face?

“He who does not work, neither shall he eat.”

John Smith

Modern Abundance

It’s a tall order to imagine what it really must’ve been like in the earliest chapters of America.

I imagine people were brutally aware of their own mortality. Even those who still wanted to mooch off the labor of producers.

Quite unlike the world we live in today. Abundance outflanks us all in this modern chapter.

The standard of living has risen at least ~1000x over the past 400 years.

We’ve continued to innovate our way through challenges (in spite of those who’d still prefer to mooch off the labor of producers).

But with so much abundance, it’s often easy to forget the imperative of responsibility.

Abundance is not a given.

It’s the byproduct of men and women who’ve (metaphorically speaking) boarded ships to a new world, sojourning to Zion.

People who’ve taken radical responsibility for breathing life into their own visions for a better world. In so doing, they’ve put their shoulder to the plow, and produced a windrow of abundance.

What will my grandchildren be thankful for?

Sometimes as a thought experiment, I like to imagine what the world will be like several generations from now. (Especially for my family, if I have the good fortune of having kids and living long enough to witness grandchildren.)

Two generations from now, will people look back at think, “Wow, I’m thankful for the sacrifices previous generations made to build the world into something better.”

Who knows. Most of us will be long dead.

But I have to think, if enough of us today do our damndest to live out the best version of ourselves, and build the best “now” that we can, then the future ought to end up a little brighter and better than it is today.

We have such an advantage in building the future today. Especially compared to the harsh conditions of the past.

Sure, plenty of opportunity for progress remains. But so long as we don’t completely burn the American experiment to the ground, then maybe, just maybe, every future generation can continue to find it a little bit easier than the previous one had it to make a start.

That’s the true miracle of the past 400 years, in my opinion.

Practicing Gratitude

Gratitude is a strange, but necessary thing.

On one hand, gratitude poses a challenge. Because there’s a fine line between admitting circumstances beyond control played out favorably and discounting actual effort put into creating favorable circumstances.

Practicing gratitude is not the same thing as self-sacrifice. It doesn’t have to be some pompous pretend show.

“I’m feeling so blessed by God right now for all these things He provided for me.” (While casually alluding to the lifestyle you deliberately set out to create.)

That’s not gratitude in my book. It’s deceitfully ascribing the results of your own choices to some power outside yourself.

Not to say that we haven’t each been blessed with unique gifts and talents to create better circumstances – and free will to choose how to apply our gifts and talents in the world.

But I always feel a phony any time I catch myself pretending I feel blessed for the results of using my talents. Because what I feel in those moments is not gratitude – it’s pride.

Which is why gratitude can be such a complicated emotion and action. If for no other reason than that I like to overcomplicate things.

Gratitude As Seeking Joy

On the other hand, I often like to think about the object of gratitude. What am I grateful for? When I boil it down, this “object” of gratitude is more or less the margin between an idyllic present and worst case scenario.

Even if present circumstances aren’t perfect, it’s possible to idealize them. And that’s where gratitude really shines. Especially contrasted against how much worse things could be. Because inevitably, things could always be much, much worse than they are.

It’s almost as if gratitude is the practice of deliberate excavation of joy from the details of our life – imperfect as they may be.

We practice gratitude when we deliberately seek joy over other possible attitudes.

Which is the beauty of it. That gratitude is a choice, not a given.

Things I’m Grateful For

It’s the day before 2021 Thanksgiving. Tomorrow I get to spend the whole day cooking, feasting, and fellowshipping with family.

I have not done this in years. For the past decade, I lived nearly a 1,000 miles away, and rarely came home for Thanksgiving. Now that I live close again, it would seem like a wasted opportunity not to take advantage of proximity to family.

I’m grateful for the maturity and wisdom that comes from reflection on past experience.

I’m also grateful for the agency to redirect my time, resources and attention as I navigate through different eras of life, and my priorities shift.

I imagine joy would be such a difficult state to achieve in the absence of choice. I’m grateful for the power to choose, for free will, and for the cognitive ability to evaluate different possible choices, then act out those choices.

I’m also grateful for people. It would surely be a lonely, miserable existence without others in our lives to accompany us on our journey through time. How diminished joy would be without others to share in its revelations.

I’m grateful for family. For Friends. For freedom. Good business. Life. Health. And a long list of other things.

What would the best version of yourself be like?

Here is a useful tip I’ve discovered whenever I encounter unknown situations:

Just ask yourself, “What would the best version of myself be like in this moment?”

(This is particularly useful for robots, like that Facebook founder, who are only pretending to be humans. Just a joke. Chill out. Don’t put me on some list.)

Anyway, it’s a useful tip because it’s an open-ended question. Which forces you to flip on the ol’ imagination. Rather than asking yourself silly, self-doubting (or self-loathing) closed- ended questions. Like, “Should I do X?”, “Should I have said Y?”

This question is not meant to encourage you to shut off in the middle of real-life scenarios, so you can brainstorm how to behave. Don’t do that, psycho. Just be authentic.

It’s really meant more for reflection. Especially if you ever find yourself putting your foot in your own mouth. Or wishing you’d have handled a situation differently.

You’re going to botch it all up quite a few times in your life. Shrug it off. Then reflect.

How could that have gone differently?

“How would the best version of myself handled that moment?”

Asking these kinds of questions creates the semblance of an ideal for you to strive for in future scenarios. That, paired with the critical self-knowledge of your own past uncomfortable failures, gives you some good guardrails for future interactions.

“What’s the worst than could happen?” and “How would the best version of myself handle this?”

Aim to end up somewhere in the middle of those. Reflect. Move on with your life. Improve in the future.

Good Destination, Bad Directions

I turn 30 today (happy birthday to me, right?). Aging tends to force reflection. It gives cause to think back on decisions – the good, the bad, and the ugly. If we’re smart, that reflection offers lessons to help us improve ourselves over time.

Here’s one big lesson I’ve been meditating on:

Having the proper destination in mind does not validate your route to it.

Life is a series of goals. We make subsequent decisions in relation to our goals. Often we do the best that we can with the information we have.

But we don’t always have the best information. Nor do we always have the best of intentions. (Thought even when we do have good intentions, sometimes we’re bad at selecting the proper means.)

Still, with our limited knowledge, we aim at the highest, best goals we can fathom (if we are wise), and we dedicate ourselves to manifesting those into reality.

Except we’re not always great at bringing our ideas to life. Not to the level of perfection we all likely aspire to.

We choose our goals. Then we choose the route that we believe is most likely to get us there. Hopefully, most efficiently.

Sometimes, though, we choose the right goal but the wrong route. Which makes it incredibly difficult to see our own errors.

It can often feel like “selecting your goal” is the most difficult part of personal development. But that’s rarely true. Choosing a target is easier than hitting it.

But when you take special care in selecting which targets to aim at with your scarce resources, and you finally determine one that’s worthwhile – it can give you a sense of absolution about the means you select for getting there.

Choosing a good destination does not let you off the hook for using bad directions, though.

Even honorable goals are overshadowed by unworthy means.

The work isn’t done once you choose your target. You must also take special care as you work toward it, to ensure that you’re not allowing a desirable “end” is to justify bad means.

Radical Generosity is Good for the Soul

If you’re looking for a quick remedy to improve your life, look no further than generosity.

Generosity changes your orientation.

It opens up your purview to think instead about how to be useful, valuable, or of service to other people.

(Which is not necessarily the opposite of selfishness, properly defined. Nor am I advocating for selfless altruism. But that’s for another blog post.)

Being radically generous is a great way to restore yourself. To freely give of the best that is within you to the loved ones in your life – and even pure strangers – without any expectation of repayment.

But it’s not a one-sided transaction. Because in order to give, someone must also receive.

Be radically generous with the people in your life, with your resources, with your gifts and talents, and your time. If for no other reason than to improve your own happiness and quality of life (and the others around you, too).

Age and Perspective

The older I get the more sentimental I become. Especially about the time I get with family.

You never really know how much time you have left. I don’t say that to be morbid. But to remind myself of the importance of prioritizing what matters.

There’s a really jarring post about this from a blog I enjoy, The Tail End from Wait But Why. Illustrating your life in dots based on the average human lifespan, it forecasts “how many times left” the average person might have based on where they are in their journey.

I think a lot of us grow up fearing our own mortality, and so naturally, we avoid thinking about it at all costs. But I’m not afraid to die. What scares me much more is getting to the end and realizing I took things for granted.

This is, in part, I think, why I get more sentimental with time. The people and things in our life that make us who we are – they matter. They’re worthy of our affection, admiration, and gratitude.

It doesn’t all have to be captured and shared on social media, either. We can savor experiences without sharing them with the world.

It makes those moments more intimate. If for no other reason than scarcity. When there are no pictures or videos or archives to reflect on later, only the catalogue of our own memories.

We never know when we’re going to do our last something. So it warrants being present. We’ve got to show up for our own lives.

I don’t know when will be the last time I’ll read Salinger’s Catcher in the Rye. Or when I’ll uncork my last bottle of wine shared with family and friends. Just like I don’t know the last time I’ll take a walk holding hands with my wife.

But I want to be there for every one of the times I do get. I want to savor all of those precious moments, big and small alike – and as Thoreau once said, “to suck out all the marrow of life.”

Knowledge Proxies

The world continues to increase in complexity. On average, we’re poorly equipped to handle this.

Our iPhones and Google empower us to “fact check” and “research” on the fly. While non-stop streams of propaganda (oops – I mean social media) color our opinions.

I often wonder if our perception of knowledge deludes us to our ignorance.

For instance, I know that I’m still fascinated on a regular basis about how abysmally little I know about the world around me. Even the simple stuff. Including things I feel like I know a lot about.

It’s honestly incredible people don’t regularly break down from the sheer overload of complexity in our world.

But beyond my ability to ask other people and observe, I’m limited to my own experience. Maybe other people are much smarter than me. (If I was a dick, I’d add a line here, like “But I doubt it.”) Or maybe most people find bliss in ignorance.

Regardless of how other people experience the world, what chance does a guy like me (who wants to “win” at life) stand at maneuvering through all the complexity? Without wasting my best years sticking my nose inside every textbook within reach.

Facing Down Ignorance

One thing I’ve learned is that I don’t know much about much – even the stuff I think I know a lot about. Re-reading that sentence reminds me of the infamous Mark Twain quote:

“What gets us into trouble is not what we don’t know. It’s what we know for sure that just ain’t so.”

Mark Twain

But nobody likes to be a know-nothing (especially not me). So we do our best when we face situations where we risk exposing our incompetence.

There’s the “fake-it ’til you make it” crowd. Which I now consider myself expatriated from. Basically you just feign competence. Some people do this for posture’s sake. They’re not bothered by the truth of their own ignorance. Others do it to survive – believing firmly in their own ability to hustle and learn so fast they overcome their ignorance before they’re found out (this was me).

Either way, you can only fake it so many times before you’re eventually found out. This isn’t a long-term winning strategy, even if offers temporary gains.

Of course, there are other options too.

The abhorrent “I don’t know” camp comes to mind. This camp accepts the truth of reality agnostically. Whenever you encounter something novel, you admit the truth. “I don’t know.” Of course, that “I don’t know” could mean blind acceptance of your ignorance. Or it could be the fuel to your fire to acquire new information (this is the part of the camp I prefer to inhabit).

But we just can’t learn about everything. There’s simply not enough time.

So, how do we cope with an ever-increasingly complex world, with our ever-finite base of knowledge?

Here’s one potential solution: I like to call it the “knowledge proxy.”

The Knowledge Proxy

I want to tell you a story first before I tell you about knowledge proxies.

For those who don’t already know, one of my guilty pleasures is wine. I love it. Every aspect. I love to drink it. Smell it. Read about it. Learn about it. The history surrounding it. The drama of it. The scandals. The culture. The traditions. The formality. And maybe most of all is that wine demands its own pound of flesh from you before you can truly appreciate all that it has to offer. It’s one of those rare few things left in life that has an extremely high barrier to entry that even money can’t overcome.

Anyway, when I first fell in love with wine I knew very little about the subject. Which can be daunting. And expensive. But when you don’t have much money and you want to learn about something relatively pricey, you’ve got to learn how to place your bets effectively.

Which is exactly what I did when I made an accidental discovery. I take pictures of every bottle I drink that I enjoy. I take notes (even if only mental). At some point I noticed that two bottles I drank both carried the same note on the back – “Imported by Kermit Lynch.” (Who is a famous wine merchant, though I didn’t know it at the time.)

This became a beacon for me. When I didn’t know about a bottle and there was nothing around to help, rather than relying on my own limited supply of knowledge, I looked to the label. If I saw “Imported by Kermit Lynch” I read it as an endorsement – almost like insurance against buying a bad bottle.

It was not a perfect solution. But it did act as a filter. When you’re facing thousands of possible choices, sometimes all you need is a good filter. Rather than picking from among thousands, I found myself picking among dozens.

That’s a knowledge proxy.

Using Proxies to Navigate the World

Proxies, by definition, are simply a substitute. They do not fully protect you against your own ignorance. But they certainly can offer a hedge.

We all use them all the time already. Anytime we take a recommendation from someone. Or even when we rely on our own biases – after all, that’s really what biases are, anyway. They’re just shortcuts. Proxies for actual knowledge.

Proxies by themselves do not perfectly describe or define the world around us. But they can be useful in reducing the complexity enough that our simple ape brains can more effectively manage it.

But, just like anything else, proxies can be prone to error – especially if you’re using some other person’s opinion as a proxy for your own decision-making.

So tread with caution. Though here’s one tip, if I may.

Avoid Single Points of Failure

Having insufficient knowledge of a subject does not get you off the hook for making decisions. But it sure does increase the danger to you.

This is how people get taken advantage of. And if you’re a stupid person, I pity you. Unless of course, you’re stupid by choice. In which case, half of me envies you. And the other half wonders how you’ve survived this long.

Anyway, back to the point here.

Whenever you have insufficient knowledge, relying on a single proxy increases the risk of a bad decision. Because you’ve created a single point of failure.

I’ll repurpose the wine scenario to illustrate what I mean by this.

Let’s suppose for a moment that the “imported by” feature had been a bad proxy for selecting wine. Maybe I’d gotten lucky the first few times. What if I’d been wrong though, and more often than not it represented low-quality wines? That sure would’ve been sour grapes, huh?

While I my knowledge was limited, it sufficed. But as I learned more, I began to add additional layers of proxies.

Rather than rely solely on the “Imported by” proxy, I also began to catalogue the particular regions, grape varietals, and producers I enjoyed.

So I could confidently navigate a wine shop or wine menu by looking for multiple data points – multiple proxies.

If a bottle boasted, “Imported by” + “Desirable grape varietal” + “Region I’ve enjoyed”, then I could be reasonably confident about my selection – and thereby increase the bet I was willing to take (i.e. My willingness to spend more money on a particular bottle increases as my confidence in the selection does.)

The same thing is true in our day to day lives. This is the power of second opinions at work.

Proxies, by themselves, do not excuse us from responsibility for making decisions. They simply help us catalog the world around us when we don’t have all the information.

The more proxies you have, the more boldly you can navigate into uncharted territory. Of course, you can always supplement proxies with your own learnings, too.

But learning how to use proxies – and then layer multiple levels – that can be a true super power in an increasingly complex world.

The First Part of Your Career as a Tour of Duty

I read this quote the other day, and I haven’t been able to stop thinking about it.

In a word, it’s one of the best summaries about the value of apprenticeship. Especially if you’re still unsure what you want to do.

Here it goes:

“Working for others is a reconnaissance expedition; a means and not an end unto itself. It is an apprenticeship and not a goal.

You should have no long-term, or even medium-term, requirements of the first two or three companies you work for. Promotion is always welcome and brings with it the opportunity to learn more, but you are there to be sure you take every opportunity to suck out the marrow of what you need to know, to understand it and place it within a greater context for a future purpose.”

– Felix Dennis, How to Get Rich

If you’re not sure what you want out of your career, then your first priority should be the discovery process itself.

Go out and explore. Try things. Test different types of jobs in different industries. Take notes about what you’re good at, what you enjoy, and what you can’t bear. 

But don’t get caught in the trap of a safe job.

You’re not on a mission to be employed. You’re on an expedition – to discover what makes you come alive.

That’s hard work. And it might require a few failed attempts along the way as you narrow down options.

But, as Felix suggested, think of it as a reconnaissance expedition, not just the daily grind. You’re in your present job to gather strategic information. For yourself.

It’s not a job. It’s a reconnaissance expedition.

Reframe your thinking about the early part of your career as an expedition to gain clarity and context, rather than as a series of jobs you can access now. This allows you to keep the broader goal in mind.

It’s not about climbing the ladder. Or getting a raise. Or landing a job at a company so well known it’ll make your friends and family blush.

The early part of your career is about equipping you with the foundational knowledge, skills, experience, and context so that once you do find your thing, you can go all in on it.

And that’s exactly what apprenticeships are all about – helping you make the strongest possible start while you undergo your discovery process.

Ideation Versus Execution

Ideas are abundant but execution is rare.

Imagine if the opposite were true.

Ideas by themselves would be worth a fortune.

But they’re not. Because ideas don’t make themselves.

Somebody’s got to donate the blood, sweat, and tears to nurture an idea through infancy and adolescence into a full-blown reality.

Plus, there’s the matter of ownership.

You cannot own an idea the same way you can own a piece of property. For instance, both you and I could hold claim to the same idea simultaneously, without either one of us being any the wiser.

What really matters is who can make the better mousetrap.

If you and I both hold the same idea, which one of us can offer it to the world better, faster, cheaper?

In a world where ideas remain plentiful, execution will always be in high demand (and deliver a better return).

You don’t even need a great idea if your execution is great. Just a decent idea will do.

Be wary of great ideas. Unless you also obsess over bringing them to life.

Ideas are only useful in proportion to your ability to carry them out.