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.

Running Experiments in the Real World

As much as I felt like I had my entire life planned out from age six, from ages 17 – 25, the older I got the less certain I became.

During that stretch of time my plan changed at least a couple dozen times.

My first dozen-ish years of jobs.

I tried a bunch of different things. Mostly with no particular aim in mind. Other than to avoid staying too long at jobs that made me feel dead inside.

From age 6-20, I thought I wanted to be a pediatric neurosurgeon. No other goal mattered. But by the time I spent a couple years in college, I had a complete identity crisis.

I felt like I only ever wanted to achieve “that goal” because it was the most prestigious sounding goal I could imagine. That would surely impress others.

Except when I had this realization, it was earth shattering to say the least. In part because I’d tied my identity up in this goal. But probably more so because I realized I didn’t know what the hell to do if not that.

I didn’t have a framework for figuring out what to do, either.

So I rolled my sleeves up and got to work. I said yes to a ton of opportunities. And the more I said yes to, the more opportunities came my way.

I’ll be honest, several of those early jobs were brutal. But each one taught me an important lesson + gave me useful experience to carry me forward.

Over time, I found a groove.

Me, finding my groove.

Eventually, all those experiments delivered some semblance clarity. Each new opportunity became a bit more recognizable as a distinct step on a path – rather than just one more job in an erratic indeterminate sequence.

Over time, the path emerged – by trying things, identifying what worked and what didn’t, leaning into the things I had a knack for (and away from things I didn’t.

It’s not always clear how the story will play out. But if you’re unsure, just get started. You can always adapt as you gain more information.

Forward Locomotion When Lacking Information

It’s a challenge making decisions when you don’t have all the facts.

The old adage, “Do the best you can with what you’ve got”, is a nice, but hardly comforting sentiment.

After all, not just any decision will do. We want to make decisions that advance us toward something – some idealized future state or goal.

Some things that help me:

First, gain as much clarity as you can about the end destination. Describe this better state intimately if you can.

Use that description to imagine your path forward from where you are.

Who must you become to achieve this vision?

What must you do?

And equally important – who must you avoid becoming? What must you not do?

The answers to those questions determine your guardrails.

On one hand, you’ve defined your ideal and components of it.

On the other, you’ve defined a set of activities and behaviors which will either increase the difficulty of or altogether disqualify you from reaching your goal. Which is often easier than listing out the activities and behaviors that will help you.

In between those two states are behaviors and activities that could help you advance – or not – but won’t hurt your progress.

Sure, that might be useful at the abstract planning level. But what about decisions in isolation?

Here’s another tip that works for me:

When considering a decision, don’t ask “Will” this help me? Rather, ask “Could” this help me?

Language matters. “Will” offers determinate outcomes. It closes off your mind from possibilities. While asking “could” activates your creative faculties.

The truth of the matter is that you’ll almost never be able to predict definitively how one choice might play out over time. (Within reason, of course, you can safely assume how eating a bottle of rat poison might impact your fate.)

Occasionally, you’ll be forced to choose among two options. Both may seem positive. But you may be uncertain which one will help you more.

Here’s what I recommend:

Don’t lose too much sleep over the decision. Early in your life and career, say yes to everything that’s not a hell no. If one decision excites you more (or challenges you more), pick that.

As you gain more leverage, you can adapt this to say no to everything that’s not a hell yes.

Rather than fret over the relative value of two decisions, focus more on avoiding stuff you hate.

So long as you are moving in a direction away from what you hate – and away from behaviors that disqualify you from your “end prize” – then you can safely advance with confidence.

Find Your Leverage

Everything in life comes easier if you can find a leverage point.

Archimedes once famously said, “Give me a lever long enough and a fulcrum on which to place it, and I shall move the world.”

The same holds true for our own lives.

It’s not always obvious what we have to leverage. Especially when we’re just starting out.

We lack knowledge. And experience. And money. So we set out to learn, to work, and to earn.

Over time we accumulate resources. But the value of those resources are not always obvious.

It’s easy to comprehend the accumulation of wealth. We can quantify it. It’s divisible, and a medium of exchange.

But what of our knowledge and experience? These presumably hold value, too – at least, they must, because they’re the basis for our ability to earn.

Over time, our accumulated knowledge and experience appreciates in value. Except most people only tap into its potential through transactional exchanges of their time – a certain number of hours converted into a certain number of dollars.

Likely because it’s the easiest to quantify and exploit – our average, collective understanding of leverage tends to be limited to money.

So people gravitate toward accumulating money – and using leverage – to achieve financial freedom. But how much faster could you go if you made use of all forms of leverage – knowledge, experience, capital?

What if every new lesson you learned made you twice as productive?

What if you could figure out how to bottle and harness your knowledge and experience – without additional inputs of time or labor?

How To Change Your World

When you recognize your own power to influence your immediate surroundings, you can make a big difference in your world fast.

You can rearrange rooms to make them more beautiful.

You can speak more respectfully to others.

You can laugh more, and invite others to join in.

You can leave things — and people — better than you found them.

You can get your life in order — personally, professional, financially.

Of course, you can do the opposite of all those things, too.

The same power that creates can destroy.

But, given the choice, what would you choose?

Will you make the world uglier?

Or will you make it more beautiful?

Today, and every day, I choose to make the world a more beautiful place.