The Funeral Procession of Life

Do you ever find yourself feeling like the shadow of your former self has lingered in a certain space?

You probably encounter some version of this when you visit your parents’ home. Pictures of your younger self mock you from their frames with insults about who you’ve become. Or maybe you hear it in the whispers of crushed childhood dreams, calling out from you within the walls of your bedroom from long ago.

“Remember who you once aspired to be!” The voices feebly cry.

We leave a littered trail of former selves behind us when we advance on new horizons.

Maybe that’s part of growing up. That maturity isn’t so much about “becoming” an adult, as much as it is about killing the remnants of your childish self. Perhaps we’re born adults and childhood is a protective outer shell that wears away with time.

Still, I can’t help but feel the presence of that forgotten youth from time to time.

In certain spaces. 

In the melody of certain songs.

In the scent of certain seasons.

In the memories inspired by certain pictures and dust-covered trophies.

I cannot escape who I once was. Nor who I once aspired to become. Even if I wanted to, their voices cry out at me from their graves.

But I often wonder, are their voices getting stronger the farther I travel? Are my ears becoming more attuned to their cries as I age?

Sometimes I think it’s not that the ghosts of my former self are angry for dying. They just don’t want to be forgotten. They want their deaths to have meant something. 

And maybe we owe our own ghosts that much. To make this life mean something more than it would have meant, that we might bring meaning to their deaths.

How to Cope with Career Uncertainty, Boredom, and Professional Angst

Several years ago I reached all the goals I’d been aiming for professionally (at the time).

I’d climbed to the highest possible rank in the company for my respective skillset – a company whose mission I believed in. I had autonomy to choose which big problems to work on in the business. I was making great money. I’d gained respect and confidence and a robust skillset.

In other words, I had achieved everything I thought I’d been working to accomplish. 

Still, something felt off.

In spite of reaching what felt like the pinnacle of my career, I encountered a surprising feeling. 

It was not happiness. It was not excitement. Nor pride. Nor contentment. But boredom.

The feeling surprised me. I thought once I achieved my goals everything would sort itself out. Like the attainment of my goals warranted some kind of enlightenment.

But instead I found myself questioning everything about my station in life.

Should I leave my “dream job” to venture out on my own?

Should I find a new job?

Is it possible to reignite the fire I felt while I was working toward my goals?

Am I in the right place?

Does this make me ungrateful?

Am I missing something?

And on and on the second-guessing and uncertainty was overwhelming.

Because I needed to have certainty. I craved it. Still, I found myself staring down a path obscured by fog.

In the months and years that followed I would learn several big lessons about facing down uncertainty, boredom, ambition and professional angst.

I’ll spare you all the gory details of that journey and instead just get to the hard-earned advice.

If you’ve ever felt uncertainty about what to do next in your career, or uncertainty as a byproduct of boredom, or professional angst springing from impatience…then these tips might hit home with you.

How to Stare Down Uncertainty, Boredom, and Professional Angst

1. Don’t look to your job to satisfy every dimension of your curiosity. 

If you’re relying on your job to provide all of your personal and professional development, then you’re doing it wrong.

We’re all multi-dimensional individuals with ranges of curiosities that would be impossible to satisfy through a single job. Find a way to prioritize your own interests beyond your day-job. Lean into those interests. Cultivate your creatives capacities outside the office.

Reserve a part of you just for yourself and your own passions. This will recharge you; offer you a cathartic outlet; and make you an overall more interesting, well-rounded person.

2. Aim for clarity, then challenge.

Before you know what you want to do, it’s okay to go into information-gathering mode. I called this  “Your Quest for Clarity.”

Try stuff. Eliminate options that don’t seem interesting. Then double-down on the skills / career path / interests that really light your fire. Mainly, don’t do stuff you hate.

If you iterate enough, worst case you’ll find something tolerable and best case you’ll find something that excites the hell out of you – anywhere in between those two poles is still a win. But a word of caution – not long after you “find your thing” you’ll eventually get good enough that the job becomes easy. This is a danger zone.

Continue to seek out challenges that will force you to grow and develop (even if they are outside your job). When things get too easy, it’s an early warning sign of impending stagnation. 

3. Don’t burn down everything you’ve built on an impulse.

It can feel exciting to think about exiting a situation in the name of adventure. You could leave it all behind today to go chasing some other big hairy audacious goal. Maybe you’ll start your own thing. Or land an awesome new job at another cool company, and then everything will be great!

Sadly, the new adventure will probably lead you to the same spot you’re in eventually. Because the truth is, sometimes you will feel bored in your career. We live in a world of in-your-face instant gratification. There’s always a new shiny object that seems like a better path.

Patience and focus can be superpowers in your life and career. If you can find a way to trudge through the boredom, and still do your best work in the meantime, you’ll unlock the true power of uninterrupted compound interest in your career. Which means more options, not fewer. Don’t leave a job you don’t hate just because you think there may be some hypothetical better option out there. The situation you’re in may offer you more upside than you realize. 

4. Give yourself permission to daydream about your options

When you find yourself unsure about what to do next, or bored in your current situation, allow your imagination to go to work. Keep a journal of ideas. Daydream. Allow your creative capacities to run wild.

It’s okay to explore those options mentally. It can offer a release. But the brainstorming time can also lead to actual tangible developments – which can take time, energy, and focus. It’s rarely immediately obvious what steps you should take next. Give yourself some room to visualize the multiple future possibilities.

5. Target universally good actions.

While you’re in the “ugly in-between” of boredom or uncertainty, there are still positive steps you can take to build momentum.

First, you can take universally-good actions. Like saving money, paying off or paying down debt. Expanding your network. Building an audience. Creating content around your areas of interest. Writing regularly and publishing your work. Etc. The list goes on and on.

But these kinds of positive actions will expand your option set as you gain clarity; and ultimately make it easier for you to say yes once you figure out your next step. 


These are just a few suggestions from my own lived experience dealing with uncertainty, professional angst, and boredom.

You owe it to yourself to take your personal and professional development into your own hands. Don’t settle for a life that bores you. Channel your energy into your own interests and creative capacities.

Keep iterating and working hard. Even when you may not know where it’s leading.

Eventually, those positive behaviors will lead you to a place of more clarity than you have today.

Habits and Luck

Luck tends to seem spontaneous. But it’s more likely the direct average of your choices over time.

Good habits enable you to absorb the shock of negative anomalies and to enjoy the benefits of positive anomalies.

Bad habits keep you vulnerable to negative anomalies and endow positive anomalies with superstitious characteristics.

You’re likely to discount your personal agency over your life if you’re incapable of drawing the connection between your actions and your outcomes.

Positive habits increase the likelihood of advancing in the direction of your desired goal – and thereby the likelihood of success. Negative habits decrease the likelihood or eliminate the possibility altogether of success — while often directly contradicting your aims, and causing regression [away] from your goals.

The same principles are at play when people point to luck as an agent for their outcomes. People with positive habits tend to have “good luck”. Whereas people with negative habits tend to have “bad luck” more frequently.

2021 Reading List in Review

“What really knocks me out is a book that, when you’re all done reading it, you wish the author that wrote it was a terrific friend of yours and you could call him up on the phone whenever you felt like it. That doesn’t happen much, though.”

– J.D. Salinger


My 2021 reading list by the numbers

A Year of Great Books

2021 was a deep and wide year when it comes to content.

I dove into quite a few new topics, but mostly continued my deeper investigation into categories that really interest me.

This year held true to popular themes – like personal finance, careers, business, education, wine, economics, and of course, fiction.

But within most of those, I took my query deeper.

My 2021 reading list by topic and frequency (bigger words = more books on this topic).

Personal Finance

Within finance, I immersed myself in content about financial planning, building wealth, estate planning, and legacy planning. I also spent a fair amount of time reading about debt, buying debt, and privatized banking.

Several big themes have emerged from this that I’ll continue to explore in 2022:

  1. In general, I’m fascinated by the idea of leverage. Not only financial leverage, but all forms.
  2. The idea of deliberately setting out to build generational wealth has become a new goal – and learning obsession.
  3. I took my book smarts to the streets in several categories, as well. I officially set up my family’s own private bank using whole life insurance, and we’ve begun funding this. We also purchased our first residence using a combination of non-traditional financing and traditional financing (designed my deal from tenets I picked up through several books). Lastly, we also completed a cash out refinance on our rental property portfolio (using the BRRRR strategy).
  4. Plus, I also published over 100 newsletters (specifically on money, education, and career advice for young adults) – and I’m particularly proud of this 6,000+ word essay about credit card advice for teens and young adults.

Education & Careers

I continued to take the plunge down the rabbit hole here. Several notable books stand out in this category –

  1. Mastery by Robert Greene – a truly phenomenal book that lays bare the fundamentals of apprenticeship, learning, and the pursuit of mastery. I cannot recommend highly enough.
  2. Dumbing Us Down by John Taylor Gatto – if you’ve ever taken issue with schooling, then this is a must-read. JTG breaks down the root cause of schooling via government institution.
  3. The Almanack of Naval Ravikant – first half about building wealth is truly phenomenal. It articulates a lot of what I believe (and thereby what we believe at Praxis). But also lays a strong framework for thinking about education + skill building as a form of leverage.

Business

I learned so much about business in 2021 – again. Now officially wrapped up my second year owning and operating a business (technically two businesses, I suppose, though honestly, the real estate thing is still small and will be more hands-off this year).

This year I spent a ton of time thinking (and reading) about branding, positioning, thinking and building long-term, as well as finance.

My business reading list has begun to swing between “directly applicable today” and “big picture”. I also spent a fair amount of time considering the role of entrepreneurship as a conduit for building generational wealth, which also influenced my reading list.

The best business book I read this year, hands-down has been Seeking Wisdom – From Darwin to Munger.

Wine, Food, & Culinary Arts

I love reading about wine and food almost as much as I enjoy partaking. While I only dipped my toe into books here, I spent a lot of time testing out my learnings in the real world.

We tasted and rated over 100 wines this year (more on this here), and cooked hundreds of new recipes. I conducted the Whole 30 Diet during the month of September, and also tested out a hybrid Carnivore diet.

I’ve modeled out several wine + content business models, and have also continued to investigate the relationship between diet + lifestyle + peak performance.

Here’s to another fun (and tasty) year of trying new things.

Economics, History, Philosophy, Psychology,

I spent a ton of time with JBP this year (Jordan B. Peterson). I started and finished 12 Rules for Life and Beyond Order; and started Maps of Meaning. I also listened back through his Biblical podcast series.

His books are exceptionally powerful if you read them with the intent of extracting action items – rather than getting caught up in lofty ideas. It’s potent stuff. And it may seem self-evident.

He presents axioms like: “You have personal agency over your life” and “Don’t ignore your problems” and such. All which probably seem cliche. But rather than giving you life advice like some self-help guru, he’s extracting this wisdom from history, symbology, psychology, Biblical stories, mythology, and more.

Beyond JBP, I also dove into a fair amount of history, economics, and political philosophy. I revisited some of the greats, like Frank Chodorov, Harry Browne, and Thomas Paine. And I also got a bit more acquainted with thinkers I’ve been meaning to explore (like Deirdre McCloskey, though I haven’t made the time for the Bourgeois series yet).

I’m most proud of being invited to speak at The Objective Standard Conference this past summer about a lot of the ideas I believe. I gave a talk called How to Forge a Meaningful, Self-Directed Career which encapsulates much of my personal life + education + career philosophy.

I’m looking forward to more of this in the year ahead.

Fiction

What’s a year without a little Vonnegut, Salinger, and Hemingway? I peppered in a decent amount of fiction throughout the year. Revisited Orwell, hung out with Heller, flirted with some Kafka, and bought far more literature than I can read any time soon.

Stay tuned though. Maybe someday I’ll take a long vacation and knock out more of these!

My 2021 reading list by my personal book rating.

Recapping 2021’s Content Consumption

You can check out my full 2021 reading list + ratings here (and see all the books I bought but haven’t started yet).

I’m proud that I managed to explore nearly 60 books. I probably browsed through quite a few more, and reread half as many. But I got acquainted enough to take away something important from quite a few.

One thing I’m proud of myself for in 2021 is getting better at quitting. I don’t want to read books that don’t interest me. I used to feel compelled to finish every book. And that would drive me to stall out. This past year I did a much better job at quitting once a book bored me. This means I’m usually reading anywhere from a handful to a dozen books at any given point in time. Though I tend to only finish cover-to-cover the ones that really captivate me.

I budget exactly $100 per month for books. Which is funny though, because I never check. My book budget is the one thing I never care if I go over on. Yet somehow for two years running it’s managed to come in just below $1,200.

Here’s to another year of expanding the mind!

How (And Why) to Build Social Capital

Let’s talk about social capital – and why it’s one of the most valuable resources you can build for your long-term professional goals.

Social capital is basically the value of “goodwill” you’ve accumulated across your entire network.

In other words, how confident are you that you could pick up the phone and call somebody in your network who could actually help if you were in need of skills, advice, capital, an introduction, etc. ?

I don’t want to imply that the value of social capital is tied to charity. Or that it’s limited to transactional relationships. It’s much more than that.

Social capital is the store of value you’ve created for others.

Similarly to a bank account, it accumulates the more deposits you make. And it dwindles as you make withdrawals.

Here’s why it’s valuable:

As you go through your career, it’s useful to have people you can call on to help you out.

For instance, when you’re trying to win a new opportunity and you need a reference. Or an introduction. 

Or when you launch your own business and need an attorney or banker or CPA or expert marketer but you can’t yet afford to hire out for it.

Or when you’re trying to put a deal together and need one more check to raise the funds to buy a business or property.

And countless other scenarios.

When you’re in need is hardly the time to ask for favors – especially favors you haven’t earned. You can’t expect for people to help you out if you have zero social capital on deposit.

The value of building social capital

The purpose of social capital isn’t about building a list of people who owe you favors. 

But if you focus on creating value for other people, social capital will be a natural byproduct. People you’ve been valuable to will want to be valuable in exchange.

It’s not a given. Social capital isn’t exactly a debt to be repaid. (And if you treat it this way, you’ll surely find yourself running low on people who can help you out when you need it most.)

Personally, I like to think of social capital as a warehouse of value stored in my personal network. And when I have a particular need, I know I can turn to my network first.

For example, currently I have a variety of “social capital” on deposit across my network:

Everything from graphic designers, copywriters, and sales people whose careers I helped launch; investment bankers I’ve made introductions for; founders and CEOs I’ve built sweat equity with; and hundreds of former co-workers with plenty of unique skill sets with whom I’ve built a strong reputation.

At any point in time, I know I could reach out (or those people could reach out to me) and we’d help one another out. 

That’s the value of social capital.

How to build social capital

The best way to build social capital is by offering value to other people (whether or not you get anything tangible in return).

Social capital isn’t something you have to build for free, though. It’s possible to accumulate it even on-the-job.

For instance, you could build social capital with a boss or your peers – even though you’re being paid to perform a job. You could do that by going above and beyond in your role, always exceeding expectations, always being the first person to volunteer to help, and so on.

In short, you can start building social capital wherever you are today by becoming reliable and indispensable.

Over time, that “excess value” you create above and beyond your pay will begin to accumulate. First in the form of your reputation among others, and eventually in the form of social capital – that you can draw on down the road, should you need a letter of recommendation or the like.

Another useful and easy way to build social capital is by helping people reach their own goals.

For example, you could help someone promote a new book or product they’ve launched. Or make an introduction between two mutual connections. Or create marketing collateral for an entrepreneur or business owner.

There are countless ways you can be valuable to other people. And if you focus on being valuable first, eventually, that value will accumulate across the network you build.

Go be valuable today.

Goals as Sustenance

I remember this group of girls at my high school who seemed to want nothing more from life than to date a good-looking guy and win homecoming queen.

At least one of them got everything she ever wanted (only one person can win homecoming queen per year, yanno?).

But it never made much sense to me to shoot so low.

If goals are already within your reach, then what’s the point? Where is the meaning to be found from life?

Goals as a forcing function

Instead, I think it’s more useful to choose goals that force you to change.

Goals, by very definition, are about manifesting a different future state. But there’s a big difference between bringing about a future state that’s already a forgone conclusion and in manifesting something you’re not yet capable of creating.

Only chasing forgone conclusions snubs your own potential – your potential to become something more than you already are.

And goals that require you to cultivate that potential – to become who you are not yet but could be – those are the best kinds of goals.

Because it is the process of metamorphosis that enables us to reach new heights.

And we’re all equally free to pursue and prioritize the cultivation of our highest potentials. Even if it’s an unequal distribution in people who actually do that.

In other words, we all have the opportunity to manifest a better future than our present circumstances. If we really desire it, we have the option to escape the life we were born into, and to turn the hand we were dealt into a winning one.

The Cycle of Goals

The process of setting and working toward a goal has restorative and regenerative properties.

It’s half therapy and half fertilization.

The therapy part requires us to examine who we are – who we were in the past – and contrast that against an ideal future state.

The fertilization aspect takes the seed of an idea (our idyllic future) and grants it what it needs to grow – motivation, inspiration, resolve, a plan of action, etc.

In that sense, the undertaking of choosing a goal then moving toward it is a form of self-transformation.

It is the process of continuous evolution. Of correcting errors in your past by improving your behavior in the present, in pursuit of an further improvement still in the future.

And without a continuously ascending target above the horizon to aim at, then we’ll probably get everything we ever wanted.

Which means we probably aimed lower than our potential could have allowed. And I can hardly imagine a fate worse than that.

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.”

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.