The Challenge of Progress

It’s incredibly difficult to feel consistently drawn to the same future goal. 

When you want something really bad and go after it with everything you have, it changes you.

As you change, your goals do too.

Goals that once seemed so big, hairy, and audacious they’d eat you alive now seem tame, familiar, and small.

As you approach your goals, you will often outgrow them, or lose interest in them for want of a novel and more interesting goal.

You grow. Your goals grow. 

It took me awhile to recognize this pattern. At first I mistakenly assumed my goals would continue to expand in proportion to my own growth.

But that’s not really how it happens.

It’s more like you begin to converge more with your goals. Rather than growing in size or stature, you and your goals begin to grow in harmony.

At least, if you take the process seriously.

It’s not that your goals grow in magnitude. But that they grow in unique and interesting ways you never before imagined.

Goals are more like ivy than trees. Both start as small sprouts, then take different trajectories.

Trees ascend vertically. Ivy expands in every direction.

Curiosity and action are like photosynthesis. 

You may start out fixated on a particular point. That particular point takes apical dominance over everything else.

But something else catches your fancy, and you divert resources in a new interesting direction.

You are not a tree. You’re like ivy. 

You start by thinking you want to grow in one general direction. But as your interests, experience, relationships, and curiosity expand in that direction, it opens up new horizons for growth.

Suddenly, growth becomes non-linear. Both directionally and in magnitude

Your growth offshoots in a new direct. Your path branches. You grow into a new patch of soil where the sun shines a little brighter, where the water is more abundant, and growth explodes.

What started as incremental growth becomes exponential.

And if you’re persistent, this process repeats itself until it becomes impossible to identify the origin point of that first little sprout.

It’s a messy but beautiful process. 

Indeterminate Growth and Your Environment

Did you know some species of plants and animals continue to grow until they die? It’s referred to as indeterminate growth.

Indeterminate growers do not have a genetically predetermined growth apex. So long as conditions in their environment remain favorable, they will survive and continue to increase in size.

Some popular examples include tomato plants, grapevines, lizards, goldfish, and a wide variety of other plants and animals.

But the conditions for their growth must remain favorable – otherwise, these species will stop growing or die.

Take goldfish, for instance. If you’ve ever had a pet goldfish, maybe you’ve witnessed this.

Assuming favorable conditions – i.e. food, water quality, etc. – a goldfish will grow in line with the size of its container.

Small bowl? Small goldfish. Large pond? Large goldfish.

Environment matters. But so does innate potential.

Not all species are indeterminate growers. Put a terminate grower into a larger pond, and once it reaches its natural biological size, it will stop growing.

The environment may impact its longevity. Or its quality of life. Or its likelihood to thrive.

Terminate growers have a fixed growth potential, regardless of their environment. But indeterminate growers will continue to expand to the size of their environment.

That feels like a layup for an inspirational message:

If you want to thrive, plant yourself in an environment with favorable conditions and enough space for your growth.

Scope of Impact

Would you rather help 100 people make their lives 10x better or help 1,000 people make their lives 1x better?

That’s a challenge you’ll have to wrestle with if you ever start a business. Whether you put it in those terms or not.

Every business has natural constraints.

Your constraint might be time. For someone else’s business, it might be talent or expertise. For another business, it might be an economic equation. Or a combination of all of the above.

Constraints provide the limiting function of your ability to make an impact.

Because resources are limited, you must make decisions about where you allocate them. You must accept some tradeoffs as favorable compared to others, and accept the opportunity cost.

But when it comes to scope of impact, it’s also a matter of more than resources. Your disposition also matters.

Would you prefer to have a sizable impact on a small group of people, or a modest impact on a large group of people?

Something to ponder if you’re motivated by making an impact.

Gratitude and Giving Back

Have you ever heard this idiom?

Like a turtle on a fence post – you didn’t get there by yourself.

Does anyone really get where they’re at by themselves? I’m not sure.

What I do know is that I’ve had a long line of benefactors whose investment in my life of their time, knowledge, and resources have helped put me on my path.

It’s definitely a dopamine hit to acknowledge gratitude for my own selfish benefit. But I’ve found it’s even better to give back.

Sure, there’s a sort of self-interested-ness in helping others in need. I’m not sure it’s possible to voluntarily help someone without benefiting yourself. (Queue your best SBF Effective Altruism joke.)

But the benefit can go both ways.

Recently I reached out to a few major influences on me in high school to let them know how much I appreciated their impact on my life. The small act provided a sense of conviction that I can – and therefore should – do more to give back.

Which is something I’ve struggled with in recent years.

I’ve always aspired to [be able to] give back in a meaningful way. In a way that makes a monumental positive impact. Not to be showy. But to improve the world we inhabit.

Except I’ve struggled with the idea because I’m not at a point in my life or financial journey where I can donate libraries or schools or hospital wings. Maybe I never will be.

But it begs to question – what’s the threshold for generosity in order to make an impact?

I doubt it’s as high it sometimes seems to me. Maybe you can make a meaningful difference giving only a few bucks or a few hours of your time.

As I’ve been pondering this a memory resurfaced from high school.

We had a big convention out of state for a school organization. The school had a budget for only a fixed amount of students. So not everyone could go, unless they could raise the extra money to cover their way.

Somehow a few alumni caught wind of a couple of students who were going to miss out. So they cut checks to cover the costs.

No questions asked. No grand gestures. Just a clearly identified need within their capability, and a desire to fill it.

It probably didn’t require more than a few hundred bucks. But their generosity was timely and maximally impactful for the couple students it directly benefitted.

Indirectly, the story stuck with me. So that small gesture is still paying dividends.

Perhaps it’s easier to have a big impact than it often feels. Identify a need within your capabilities and fill it.

Advice in a Vacuum

When most people ask for career advice, they’re really asking for happiness advice.

They’re rarely only trying to ascend a professional hierarchy. Most people usually want to know how to succeed professionally, and be happy in their personal lives.

It’s important when you’re approached for advice to understand what people are looking for before spewing generic nonsense.

What gets you to the top of the mountain quickest (professionally speaking) may bear a cost you’re not worth paying.

Similarly, the balanced equation of “What will make me happiest, on net?” likely requires some small tradeoff between your personal professional life.

In other words, people rarely seek advice in a vacuum.

Most people are trying simultaneously to win – or at the very minimum, compete – at all the various game of life they play.

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.


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.


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.