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.

Context: The Proper Target For New Adults

Because of the work we do at Praxis, I get the good fortune of speaking with thousands of young adults all over the country each year.

Most of them are at the stage in their journey where they’re still uncertain about who they are – and perhaps more importantly – who they want to become.

It can be a confusing time. I certainly know I was confused at that stage in my life.

But it doesn’t have to be as confusing or stressful as many of us make it.

Missing Context

When we’re just starting out, we still lack a ton of important context about the world around us. So it’s highly unlikely we’ll correctly choose “the one thing” we want to spend the rest of our lives doing.

First off, because the idea that there is “one perfect path” is mostly a myth. 

Second, because we just don’t know what we don’t know. 

Those can be tough things to come to grips with. Both are true.

It’s tough to decide what you want to do and who you want to become against a backdrop of limited knowledge about what’s possible.

I believe this is at the heart of many decisions to default to college. Because it’s almost as scary to not have a plan as it is to admit you don’t know what you’re doing.

I mean no disrespect when I say this. But at 18 years old, most people don’t have enough context to lock themselves into a decision that will cost them years of their lives and hundreds of thousands of dollars.

Without context, it’s difficult to imagine all the possible paths you could go down.

Gaining Context

To no fault of their own, many young adults lack context simply because they lack experience.

So one of the first hurdles to overcome is to gain context about the world around you.

How can you do this? Simple. Try stuff.

In particular, try stuff that allows you to explore in the direction you’re hoping to advance.

Gaining context means enriching your perspective about the topic you’re interested in. You may imagine a path as suitable or exciting. But with a little context, you may quickly discover that a path is not all it’s cracked up to be.

For instance, I thought I wanted to be a lawyer. Then I spent half a year as a legal aid for a law firm. Which made me quickly realize being a lawyer wasn’t all I thought it was. 

The missing context enriched my perspective.

Context Clues

You are likely interested in many things. It can feel stressful to pick just one. You don’t want to feel limited – or one dimensional. I get it.

But often, one of the best things you can do to gain context and clarity about the path forward, is to choose one dimension of yourself to cultivate.

As you cultivate one interest, it can enrich your life – by giving you a craft to master, by helping you build momentum and gain experience, and by lead to surprising opportunities.

For instance, when I quit my law firm job, I went all-in on photography. I didn’t know where it would lead. But it was the most interesting thing I had going at the time. Eventually, I landed a job as a photographer. While working that job, I met the founder of Praxis, who later introduced me to another entrepreneur who ended up offering me a job.

What may look like a series of happy accidents was actually the byproduct of cultivating one interest, and allowing it to lead the way. Leaning into one interest (photography) didn’t mean I gave up all the other interests I had. 

Following one dominant interest gave me a path forward, that ultimately led to new, exciting opportunities I could not have anticipated.

This same context clues can help you discover your path forward, too.

Discovering Your Thing

You don’t have to have it all figured out right now. It takes time, context, effort, and courage to discover your thing – or the multiple “things” you’re interested in that can define how you build your life and career.

If you’re not sure what you want to do – or who you want to become – then take inventory of your interests. Ask yourself how you could explore those interests more deeply. Look for opportunities to gain context. 

You don’t have to default to a boring or unfulfilling path just because you’re not sure how things will work out.

There are tons of exciting options out there waiting to be discovered. 

(And it just so happens that our apprenticeship program at Praxis can help you start your own discovery process.)

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.

Succeeding Along Specific Dimensions

Very little in life is as fulfilling as achieving success along a specific dimension you set out to conquer . But the flip side is that this is also one of the most challenging things.

Defining Success Is Only Half the Battle

For example, let’s say you set out to grow your business.

Growing a business in and of itself is challenging. Choosing to define that as a goal is only a fraction of the battle. Defining how much growth, and along what metrics will move you ever so slightly closer, as well.

But what makes this infinitely more difficult is figuring out the required levers to pull in order to actually achieve the desired growth.

Chances are even if you hit your desired growth target the metrics you defined probably didn’t line up perfectly the way you thought they should in order to succeed.

Nebulous Success & Happy “Accidents”

To some degree, success along any dimension you specify will always be somewhat nebulous.

Not because it’s impossible to figure out what currently known activities may lead to your success. But because it’s entirely impossible to predict all possible contributors to your success that are currently unknown.

These “unknown contributors” will feel like happy accidents when they happen. But they rarely happen through inertia alone.

In fact, they often seem to spring forth only after, and as a direct byproduct of, exhaustive effort toward a goal. Even when those happy accidents seem to appear entirely out of the blue, independent of your efforts.

Which only increases the level of satisfaction when you begin to experience initial success.

The Combined Power of Labor + Intellect

When happy accidents begin to occur, it can feel like the universe is participating in a grand conspiracy on your behalf.

And the truly beautiful thing about this is remembering that it’s not actually random. But the byproduct of your deliberate progress toward a definite aim.

When you set your sights on a specific target, and do everything in your power to advance toward it, you can be confident that your success is not accidental at all. But through your own agency – the combined power of your labor and intellect to shape the world into your vision for it.

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!

Best Wines of 2021

We tasted many incredible wines this year. I keep a running catalog with pictures and notes from our favorites.

This year, I wanted to publicly share the simple version of this list with my quick ratings. I assigned each wine a score out of 10. I guess you could say my score represents how much I enjoyed. But more realistically, it’s a relative value of a particular wine versus my mental catalogue of other wines of the same varietal / type. To an extent, the circumstances of when and where we drank the wine likely also influence my score.

For example, when I score 2006 Dom Pérignon a perfect 10 out of 10, it’s worth noting that I opened this the night of our wedding. I searched for this particular vintage for months because my wife and I first met in 2006. This was also our first tasting of Dom Pérignon. We have since tasted the wine on two other occasions. We drank the 2006 again on our honeymoon, and drank the 2010 vintage this year after finishing the remodel of our house. The first tasting of 2006 was phenomenal. The second bottle of 2006 was not nearly as well preserved. By all means, it was still enjoyable, but likely closer to a 8-9 out of 10. The 2010 was also showing well, and remains among my top champagnes for the year.

I reconstructed this list more or less in the order which we drank the wines throughout the yet.

Okay, onward to the wines. (I will update this as we finish our remaining wine tastings for the year.)

Notable Wines from the List

A few exceptional wines stand out among the list, and these deserve a special additional note.

I already paid homage to the Dom Pérignon vintages.

We tasted through many other truly phenomenal champagnes, Bordeaux blends, burgundies, barolos, as well as a number of notable rieslings.

Top Champagnes & Bubbles:

When you can’t (yet) afford to drink Dom Pérignon, Cristal, or La Grande Dame every night, you’ve got to find a nice middle ground. Heading into 2021, our go-to champagne has been Moet & Chandon Imperial Brut for quite some time. But there are a couple new kids on the block.

In the “more affordable” category, may I introduce Schamsberg Blanc de Noirs. This beautiful blend of ~80% pinot noir and ~20% chardonnay is a sure crowd-pleaser. Especially when you consider the average retail price of $35-$40.

In the “Best under $100” category, I’ve got to go with Louis Roderer Estate Brut Premier. At an average retail price around $67, you probably won’t want to pop this baby every night. But the pure freshness, silky bubbles, vibrant flavor, inviting finish will leave you inventing special occasions to splurge. I’d also recommend Bollinger Special Cuvee, too, at a still slightly higher price point.

Top Bordeaux & Cabernet Sauvignon:

Anyone who knows me well knows how much of a sucker I am for “Magic Marker Reds” and we definitely hit our quota this year.

Many of these came from France, though a few American entries certainly snuck in.

It would be impossible to rank these in order. Instead, I’d recommend trying all of them yourself. 😉

  • Château D’Issan Grand Cru Margaux 2015
  • Alta Gracia Napa Valley Cabernet Sauvignon 2014
  • Château de Lescours Saint-Emilion Grand Cru 2015
  • Château La Tour De Mons Margaux
  • Mira Napa Valley Cabernet Sauvignon 2013
  • Caymus Vineyards Napa Valley Cabernet Sauvignon 2019
  • Keenan Napa Valley Cabernet Sauvignon 2017
  • Blackbird Vineyards Arise Bordeaux Blend 2015
  • Chateau Rauzan-Segla Margaux 2015
  • Barons de Rothschild Saint-Emilion Légende Bordeaux 2016
  • O’Shaughnessy Napa Valley Cabernet Sauvignon 2018
  • Château Malescot St. Exupéry Margaux 2018
  • Château De Sales Pomerol Bordeaux 2018
  • Justin Savant Red Blend 2018
  • Johndrow Vineyards Napa Valley Forum Confidential Reserve 2006
  • Justin Justification Red Blend 2016
  • Stony Hill Cabernet Sauvignon 2015

Top Barolo:

We drank a lot more barbera and tuscan wine than we did barolo this year. But we made the most of the ones we did sneak into the list. Here are a few of the hits:

  • Parusso Barolo 2014
  • Damilano Lecinquevigne Barolo 2016
  • Massolino Serralunga D’Alba Barolo 2015
  • Pio Cesare Barolo 2016 (If picking something from piedmont intimidates you, Pio Cesare is an excellent, reliable top producer. Always a crowd favorite.)
  • Guido Porro Barolo Vigna Lazzairasco 2015 (If I had to pick my top selection, this one takes the cake for the year.)

Top Burgundian / Beaujolais / Châteauneuf-du-Pape

If 2020 was the year I fell in love with burgundy, then 2021 was the year I ran away on a lover’s affair with it. We drank so many truly incredible wines from the region – and within a surprising budget, given Burgundy’s reputation for breaking the bank. Here are a few of those memorable selections (with a few other delightful wines from nearby regions thrown in for good measure):

  • Gevrey-Chambertin Chanson Bourgogne 2016
  • Henry Natter Sancerre
  • Gevrey-Chambertin Magnien Premier Cru Cazetiers 2013 (<–this one was truly incredible, drank on our honeymoon)
  • Chateau Fortia Châteauneuf-du-Pape Cuvée du Baron 2017
  • Pierre-Marie Chermette Fleurie Poncié 2016
  • Pierre-Marie Chermette Fleurie Les Garants 2017
  • Aegerter Jean-Luc & Paul Bourgogne Pinot Noir Reserve
  • Louis Latour Bourgogne Pinot Noir 2017 (Great value buy)
  • Domaine Antonin Guyin Gevrey-Chambertin La Justice 2018 (<–also phenomenal)
  • Louis Jadot Bourgogne Pinot Noir (Great value buy)
  • Domaine Pierre Guillemot Savigny-les-Beaune Aux Serpentières Premier Cru 2018 (<–truly fantastic, drank for my 30th birthday)
  • Charles Audoin Bourgogne 2016
  • Louis Latour Les Pierres Dorées Pinot Noir

A Few Beautiful White Wines

After being forced to forego our trip to Alsace in 2020, Riesling and
Gewürztraminer were a touch on the bittersweet side. We did not venture as far into this region of the world as typical, but still tasted several delightful wines. The value-to-quality ratio for these wines is nearly unmatched. Here are a few I’d recommend:

  • Holy Cross Abbey Winery Riesling (<–surprisingly good, especially for a wine made in Colorado)
  • Alkoomi Franklin River Australia Riesling 2017
  • Kuentz-Bas Alsace Riesling 2018 (<–one of my favorite rieslings, esp. for the price)
  • Trefethen Oak Knoll District Napa Valley Dry Riesling 2020
  • Domaine Specht Mandelberg Alsace Grand Cru Riesling
  • Dönnhoff Riesling Nahe 2019 (<–exceptional)
  • Trimbach Riesling & Gewürztraminer (<– these are two of my go-to wines, though I favor the Gewürztraminer)

The Top Wines I Tasted in 2021

This is by no means a comprehensive list, but I tried to include any wine that I would definitely drink again if given the chance. Then, of course, there are plenty of wines that did not make these list. Though I will say, I don’t think we encountered a single wine this year that was so bad we couldn’t finish it. Yay us.

Without further ado, here’s the entire list:

Moet & Chandon Imperial Brut 9/10

Gaston Chiquet Premier Cru Champagne 8/10

Veuve Clicquot Champagne 9/10

Dom Pérignon Champagne 2006 10/10

Château D’Issan Grand Cru Margaux 2015 10/10

Schramsberg Blanc de Blancs 7.5/10

Schramsberg Blanc de Noirs 8.5/10

Alta Gracia Napa Valley Cabernet Sauvignon 2014 9.5/10

Groth Napa Valley, Oakville Cabernet Sauvignon 2016 8/10

Gevrey-Chambertin 2016 Chanson Bourgogne 8.5/10

Henry Natter Sancerre 9/10

Gevrey-Chambertin Magnien 2013 Premier Cru Cazetiers 10/10

Belle Glos Pinot Noir Dairyman 7.5/10

Ripassa Valpolicella Ripasso Superiore 2013 7.5/10

HG III Napa Valley Proprietary Blend 2018 8/10

Erba Napa Valley Cabernet Sauvignon 2011 7.5/10

Château De Pizay Morgon 7.5/10

Holy Cross Abbey Winery Riesling 7.5/10

Château Fortia Chateauneuf-du-Pape Cuvée du Baron 2017 8/10

Alkoomi Franklin River Australia Riesling 2017 7.5/10

Pierre-Marie Chermette Fleurie Poncié 2016 9/10

Pierre-Marie Chermette Fleurie Les Garants 2017 9/10

Algodon Argentina Estate Pinot Noir 2015 8.5/10

Left Coast Cellars Blanc de Noir 8.5/10

Parusso Barolo 2014 8.5/10

Château de Lescours Saint-Emilion Grand Cru 2015 9.5/10

Blackbird Vineyards Arise Bordeaux Blend 2015 9.5/10

Aegerter Jean-Luc & Paul Bourgogne Pinot Noir Reserve 8/10

Louis Latour Bourgogne Pinot Noir 2017 9/10

Château La Tour De Mons Margaux 8.5/10

Mira Napa Valley Cabernet Sauvignon 2013 8.5/10

Bollinger Special Cuvee Champagne 9/10

Marques de Fiscal Rioja Reserva 7/10

Caymus Vineyards Napa Valley Cabernet Sauvignon 2019 8/10

Keenan Napa Valley Cabernet Sauvignon 2017 8.5/10

Poliziana Vino Nobile di Montepulciano 7.5/10

Veuve Clicquot La Grande Dame 2008 Champagne 9.5/10

Etude Estate Grown Pinot Noir 2018 7/10

Dom Pérignon Champagne 2010 10/10

Hearst Ranch Winery Cabernet Franc 7/10

Bussi Piero Barbera D’Astia Superiore 7.5/10

Louis Roederer Cristal Champagne 2009 10/10

Chateau Rauzan-Segla Margaux 2015 10/10

Domaine Antonin Guyin Gevrey-Chambertin La Justice 2018 10/10

Louis Jadot Bourgogne Pinot Noir 8.5/10

Damilano Lecinquevigne Barolo 2016 8.5/10

Le Cigare Volant 2018 7/10

Louis Jadot Beaujolais-Villages Gamay 7/10

Barons de Rothschild Saint-Emilion Légende Bordeaux 2016 9/10

Massolino Serralunga D’Alba Barolo 2015 8.5/10

Banfi Rosso di Montalcino Chianti 2016 7.5/10

Nicolas Feuillatte Reserve Exclusive Brut 8.5/10

Louis Roederer Brut Premier Champagne 10/10

Domaine Pierre Guillemot Savigny-les-Beaune Aux Serpentières Premier Cru 2018 10/10

Pio Cesare Barolo 2016 10/10

O’Shaughnessy Napa Valley Cabernet Sauvignon 2018 10/10

Kuentz-Bas Alsace Riesling 2018 8.5/10

Trefethen Oak Knoll District Napa Valley Dry Riesling 2020 8/10

Louis Roederer Collection 242 Champagne 9/10

Charles Audoin Bourgogne 2016 8/10

Château Malescot St. Exupéry Margaux 2018 10/10

Château De Sales Pomerol Bordeaux 2018 8.5/10

Champagne J. Lassalle “Preference” Premier Cru 8.5/10

Justin Savant Red Blend 2018 10/10

Domaine Specht Mandelberg Alsace Grand Cru Riesling 9/10

Veuve Clicquot Rosé Champagne 9/10

Johndrow Vineyards Napa Valley Forum Confidential Reserve 2006 9.5/10

Louis Latour Les Pierres Dorées Pinot Noir 9/10

Justin Justification Red Blend 2016 9.5/10

Guido Porro Barolo Vigna Lazzairasco 2015 9.5/10

Dönnhoff Riesling Nahe 2019 8.5/10

Stony Hill Cabernet Sauvignon 2015 9/10

Secondhand Smoke

I like to joke that “secondhand Taylor Swift” is the leading reason I’m familiar with most of her songs. My wife keeps her music on repeat.

Similarly, my wife claims she’s listened to enough of my podcast episodes through the wall to host my show.

While these make for a good laugh, there’s also an important truth at work under the surface:

We passively consume what others around us do.

The famous motivational Jim Rohn once put it this way, “You are the average of the five people you spend the most time around.”

The same thing holds true for ideas. For music. Health. Habits. Money. And nearly every other aspect of life.

Negative vs. Positive Externalities

In economics, the concept “negative externalities” describes the incidences of an unavoidable cost to a third party based on your production or consumption.

Put in simple terms, a negative externality is an unavoidable bad consequence of your decisions. For instance, maybe you signed a lease at an apartment and you got randomly assigned to a unit next to a neighbor who smokes (or plays music at all hours).

Similarly, positive externalities also exist. For instance, let’s say you spend a lot of time at the local coffee shop, and it just so happens that your favorite band plays open mic night. Or that a book club regularly meets there that discusses ideas you are interested in.

While you can’t always control the externalities, you can control your decisions. If you’re deliberate enough, perhaps you can begin to spot the potential of negative externalities before you’re stuck with them.

Secondhand Consumption of Good Ideas

You can’t control what other people do. But you can control your choices.

One sure-fire way to improve your likelihood of success along a specific dimension is to limit your exposure to other people whose habits contradict your aims.

For instance, if you’re highly ambitious, but all your friends are broke, drug-addicted burnouts, it’s time to find new friends.

But it goes both ways.

You can also seek out to surround yourself with people (and books and ideas, etc.) that support you in your aims.

For example, if it’s important to you to maintain a positive outlook, actively avoid pessimists and actively seek out optimists.

You have the ability to change your location, and to replant yourself in better soil. Take advantage of this.

Secondhand smoking might kill you. But secondhand success never hurt anybody.

13 Rules for Writing

Writing is one of the highest-leverage skills you can carry in your toolkit.

Anyone can learn how to do it. And with the technology available at our fingertips today, anyone who can masterfully craft an argument can win an audience.

Writing improves thinking. Better thinking improves your ability to get the results you want from life.

With enough effort and practice, writing can change your life for the better.

So to that end, I offer you my “13 Rules for Writing Better”.

Rule 1. Write. A lot.

You won’t get better at anything if you don’t practice. You must practice to triangulate your own voice. Until you find your voice, you’re just an imitator. When you’re just imitating, you’re not thinking critically. Until you can think critically, you’re at a disadvantage when you encounter new challenges. Write. A lot. So you can survive the challenges of life.

Rule 2. Begin with the end in mind. 

What are you trying to accomplish? Starting at a blank page will steal hours of your life. That’s amplified when you don’t have an aim.

Rule 3. Copy good writing.

Find good writing. Physically copy it down by hand. Get acquainted with what if feels like to write masterfully. Borrow great writers’ voices until you find your own.

Rule 4. First sentence. Second sentence. 

Writing should flow. The goal of your first sentence is to get someone to read your second sentence. And so on.

Rule 5. Consume as much as you create. 

Keep your head full of ideas. You can’t pour out from an empty vessel.

Rule 6. Less is more. 

Great writing removes the unnecessary parts. You jump into the story no earlier than necessary. You get right to the action. You eliminate fluff. You make powerful points without excess bluster.

Rule 7. Master the rules before you break them. 

Just like any great athlete, if you want to write well, you must learn the fundamentals first.

Rule 8. Perfect your process. 

Find what works best for you. Do you write best in the mornings? Evenings? In a coffee shop? Facing a blank wall in a quiet room? Until you build the discipline to sit and write at will, remove any barriers to your creative process. 

Rule 9. Write drunk. Edit sober. 

Figuratively speaking. Unless you’re Ernest Hemingway. Don’t wait for inspiration to write. But when you do *feel* it. Sit down and get it out on paper. It’s impossible to manufacture authentic desire – so when you’re in the moment, write while your muse is smiling. Because most days you probably won’t feel like it.

Rule 10. Find a sponge bullet. 

Find someone you can bounce ideas off without ridicule. To get better, you must write a lot. Which means you’ll have plenty of duds. Find a trusted confidant who can help you navigate through your own ideas and improve them.

Rule 11. Write stuff that moves you. 

Write about what you know and care about. Especially while you’re building the muscle. Over time you can expand your horizons. But you’ll make it more difficult on yourself if you try only writing about things that bore you.

Rule 12. Do your homework. 

Get beyond the limits of your own experience. Ask questions. Read books. Draw on other sources. Color your writing with the experience and insights of others.

Rule 13. Write like you talk. 

Nobody wants to read boring academic-speak filled with thesaurus replacement words. Be real. Triangulate your authentic voice. Remove barriers to clarity from your writing.

Winning in Different Domains

Some of us are born with a competitive spirit. Some of us are not. Then others among us are born with a double-dose of it.

I got the double dose.

When you grow up with a competitive spirit, you view the world as a game board to be dominated.

You don’t care about the game. You only care about winning.

That kind of spirit to win will drive you to win at all costs. But it won’t help you figure out which games are worth playing.

Because, it’s true, some games are not worth playing at all. It’s only the games that are worth playing that are worth playing well.

And figuring out which games are worth playing is perhaps the most important game of all.

Discarding Games

If you’re anywhere near as competitive as I am, eventually you’ll come across games that bore you.

Perhaps because you’re not naturally gifted at them. Or perhaps because you encounter a worthier-than-usual foe who absolutely decimates you to the point of forfeiting all future exhibitions in a particular domain. Or probably more likely because you grow bored in some games as your interest in other games expands.

When any of the above happen, if you stand any chance at achieving longevity as a competitor in any domain of interest, it’s worthwhile to discard some games – in the interest of increasing your fitness in the new game.

Because you can’t be “the best” at everything, discarding games that you no longer care to play (for whatever reason), allows you to allocate your attention and resources to higher-priority games. This reallocation of resources will allow you to compete more seriously.

And in fact, becoming a more serious competitor in one domain often increases your fitness in other domains, as well.

So, you should take seriously the idea of discarding low-priority games. In the interest of winning more games overall. Make a game of it, if you must.

Games Worth Playing

As you grow older, you’ll carry with you an internal sense of your win record.

On net, you’re either a winner or a loser in your own eyes. (If you view yourself the latter, I’d encourage you to find a domain you can win in fast.)

You’ll also likely have a good sense of the domains you excel in – and a particularly strong lingering soreness about those domains which you do not excel in.

But hopefully, you’ll also gain a sense about those games which carry the highest stakes.

Therein lies the first clue about which games to play.

Games carry different stakes.

High-stakes games can be thrilling. They often present major upside for winners, too. But be warned. Because some high-stakes games offer minimal upside (if any at all), though certain major downside for losers.

Which is the second clue.

Avoid high-stakes games with minimal upside and major downside risks.

For instance, grabbing an uncaged tiger by its tail is a form of a high-stakes game with major downside risk. And unless you happen to be attacked by a tiger, you’re probably best avoiding the encounter altogether. If it’s unavoidable, then fight like hell.

You’ll receive many invitations to many games in many different domains. You can’t play them all. But you can’t avoid them all forever either.

So you’ve got to choose. Here’s another clue.

Figure out which games you certainly want to avoid.

Here’s a short list of examples.

If possible, avoiding playing games with the criminal justice system. Or with the legal system altogether. And the IRS. Don’t play dice with war lords, drug dealers, or loan sharks. Avoid boxing matches you can’t win. Don’t challenge a cheetah to a footrace. And never, never battle wits with a Sicilian when death is on the line.

It’s also worth taking inventory of the games you’re A) already playing and B) cannot avoid.

Which is the next clue:

Some games are unavoidable.

You’ve got to learn how to stay alive. That is maybe the most fundamental game. Though there’s really no winning in this game so much as there is only losing. And it’s a game we’ll all inevitably lose. But best to play as a worthy competitor while you can.

Still, in order to avoid losing (for as long as you can), you’ll also be forced to engage in other games. Like learning how to provide for yourself, how to earn an income or to hunt, kill, grow, and prepare your own food. And so on.

Some games are absolutely necessary in order to continue playing at all.

Which brings up the last clue (for now):

Some games necessitate others.

If you get married, for instance, you’ll have to learn how to co-exist peacefully. If you go into business, you’ll have to figure out how to manage finances. (Of course, you could avoid both of those. But recognize that some games necessitate others.)

As you go continue through the game of life, it behooves you to learn the fundamentals of the games you’re aware of. And always be mindful of the games within the games – the new domains you’re forced into as a result of necessity of other games you’ve engaged in.

Recommended Reading

Finite and Infinite Games by James P. Carse

Games People Play by Eric Berne, M.D.

The Inner Game of Tennis by W. Timothy Gallwey

Metaphors We Live By written by George Lakoff and Mark Johnson

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.