Success is the one thing we say we all want.

We see successful people: their lifestyle, their family, their wealth, their reputation, and we want those things for ourselves. These people live lives we only dream about, so it’s no surprise we feel a sting of jealousy when we look at them.

What we don’t consider is what it actually took to get there.

If given the opportunity to trade places with any of these people on an hour-by-hour basis, most of us would say no.

They’re up early when we’re sleeping in. They’re staying up late when we’re catching up on rest. They’re in the gym when we’re having a drink with friends. They’re working on interesting problems while we’re on vacation. They’re having difficult conversations with the people they love when we’re choosing the path of least resistance.

Success in multiple areas of life creates the perception of a wonderfully simple existence, but the opposite is usually true. The more impressive someone looks from the outside, the harder their life tends to be behind closed doors.

We see the outcomes, but we don’t see the years of effort required to produce them.

What we’re actually willing to do

Before we measure ourselves against anyone else, we need to ask ourselves: what are we willing to endure?

If we’re not willing to exercise every day, then we can’t expect to be fit. If we’re not willing to have challenging conversations with the people we care about, then we can’t expect to have deep relationships. If we’re not willing to work harder than everyone else around us, then we can’t expect to be better than average.

None of this means we need to sacrifice everything to achieve something meaningful. Different levels of ambition are fine. Different commitments are okay. What we can’t do is expect outcomes that our effort doesn’t support.

Pairing expectation with reality

Instead, we need to adjust our expectations to match our willingness to work in each area of life

We need to be honest about how much we’re willing to give of ourselves. Once we know that, we can set realistic expectations for our outcomes. If we want more, we need to do more. If we’re not willing to do more, we need to make peace with wanting differently.

Some say the key to happiness is low expectations, but it’s really honest expectations. Expectations that reflect what we’re willing to do.

The most useful version of jealousy isn’t the kind that poisons how we see ourselves. It’s the kind that tells us something true about what we value, and asks us whether we’re willing to pay for it.

Prompts

1. Think of someone whose success makes you feel envious. What exactly is it about their life that you want?

2. If you could trade places with that person on an hour-by-hour basis for one week, what would that actually look like? Which parts of their daily life would you be unwilling to live?

3. In one area of your life where you want better results, how much are you genuinely willing to work? What does that look like on a daily basis?

Deep Dive

• Wanting: The Power of Mimetic Desire in Everyday Life - Luke Burgis

  • An exploration of why we want what we want, and a toolkit for freeing ourselves from chasing unfulfilling desires.

Thanks for reading! I’ll see you next Sunday.

Kevin

The grass is greener where you water it.

Sometimes things really do suck. Projects get mismanaged. Jobs are a bad fit. Relationships run their course. Not everything deserves our continued investment.

But most of the time, things suck because we stop investing in them.

If we skip the oil changes and ignore the check engine light, our car doesn’t suck; we do. The same principle applies to the worthwhile pursuits in our lives: our jobs, our relationships, our creative work, etc.

The less we invest, the worse things get. And the worse things get, the easier it is to shift blame externally.

It’s a self-defense mechanism. The more reasons we create that something is broken, the less responsible we are for its failure, and the less work we need to do. If we convince ourselves that something is unsalvageable, we don’t have to try harder. When we can blame something else, we don’t have to make any changes to ourselves.

It’s a natural instinct to protect our ego and conserve our energy, but if we don’t realize we’re doing it, we become insufferable, entitled, and chronically disappointed. We believe the whole world is rigged against us and nothing is worth investing in.

Skin in the game

To live a fulfilling life, we have to invest in things that matter to us.

That means accepting risk. It means rolling up our sleeves, doing the work, and taking ownership of the outcomes regardless of whether they are good or bad.

It’s much harder than externalizing responsibility. When things go wrong, and we’ve committed fully, there’s no one else to blame but ourselves.

But when we take ownership, we’re not only accepting the risk of failure. We’re building equity. We get to participate in the upside when things go well.

If we play the blame game, we rarely lose, but we can’t win.

The upside of equity

When we commit to making meaningful progress on the pursuits we care about despite their flaws, we will inevitably face failure and embarrassment. But we also give ourselves the chance to succeed and enjoy our lives.

A funny thing happens when we shift our effort from finding imperfections to fixing them. Things get better. The more we believe in something, commit to it, and invest in it, the better it becomes.

The only way to truly participate in the upside is to commit despite imperfections. Nothing is perfect. Nothing is ever fully ready. But if we don’t commit, it only gets worse.

When our jobs, relationships, or any pursuit feel like they’re failing, we need to resist the urge to find all the reasons that it’s not our fault and try to improve things ourselves before giving up.

The grass is greener where we water it, so we should consider where we’re investing our efforts before we shift blame to everyone and everything else.

The only way to win is to have something to lose.

Prompts

1. Where in your life does it feel like the deck is stacked against you? Why?

2. Have you taken ownership of the situation, or are you focused on shifting blame externally?

3. What does taking ownership look like? How will you decide if it really is out of your control?

Deep Dive

• Extreme Ownership by Jocko Willink

  • A simple and powerful message from a Navy Seal.

Thanks for reading! I’ll see you next Sunday.

Kevin

We all know what we should be doing.

We’ve set goals. We’ve read the books. We’ve made the plans. And yet, we still find ourselves doing everything except the work that matters most.

We know exactly what we need to do and how to do it, but the most important work never gets done, creating an infuriating gap between what’s important to us and how we spend our time each day.

In most cases, our procrastination or lack of focus is not a knowledge or motivation problem. Instead, it’s a specificity issue.

Psychologist Peter Gollwitzer spent decades studying the gap between what we want to do and what we actually do. He found the biggest predictor of follow-through isn’t motivation, willpower, or how much we care about a goal. It’s how specific we are about executing it.

Make it concrete

When we say “I want to exercise more” or “I’m going to work on my side project,” we’re aiming ourselves in the right direction but setting ourselves up to struggle. These types of commitments are too vague. What kind of exercise? Is the side project a hobby or a business? What time? Where?

When we start to work on one of these vague goals, our brain doesn’t know what to do next. Go on a run? Drive to the gym? What exercise first? What if that machine is taken? Now or later?

This ambiguity turns into anxiety and indecision, so we push it off until later and never get it done.

Gollwitzer’s research found that turning ambiguous goals into concrete “I will do X at Y time in Z place” statements nearly doubles follow-through rates. Specificity gives our brain clear marching orders and eliminates the anxiety that comes from ambiguity and decision fatigue. When the time comes, there’s nothing left to figure out. We just execute.

So if we want to get something done, we can double our chances of following through by proactively defining exactly what we are going to do and where and when we’re going to do it.

But what if, after all this, we’re still stuck in a rut of procrastination and dread?

Know your why

If we’ve gotten militant about our planning and still find ourselves procrastinating, the problem probably runs deeper. We need to revisit why we’re pursuing this goal in the first place.

Accomplishing something truly worthwhile is incredibly challenging. Optimizing our schedules and planning precisely can help us stay consistent, but if we don’t believe in what we’re working on, we’ll never be able to last long enough to make meaningful progress.

Our “why” needs to be compelling enough to pull us forward on the boring days. If thinking about the outcome genuinely excites us, we’ll find a way to do the work. If it doesn’t, that pursuit isn’t worth our time.

Not all lack of motivation and existential dread can be solved with to-do list optimization. If we consistently give something our best efforts and never get excited or energized, we should call it quits instead of doubling down.

Not everything is aligned with who we are, and the more time we can focus on pursuits with a strong why, the easier it will become to get things done each day.

Prompts

1. Pick the most important thing you need to do this week and define what specifically you need to do, when you will do it, and where you will do it.

2. Why are you pursuing this project or goal? Does it genuinely excite you?

3. Are you dreading work because it’s ambiguous or because it’s unimportant?

Deep Dive

• Getting Things Done by David Allen

  • A simple and powerful system to organize our lives and get things done.

Thanks for reading! I’ll see you next Sunday.

Kevin

If we simplify performance in a given area of life, each of us exists in one of four categories:

1. Beginner

2. Arrogant

3. Undervalued

4. High Performer

Our levels of confidence and competence determine which category we fall into.

We’re at our best when our confidence is congruent with our confidence, so in a perfect world, we would move directly from Beginner to High Performer.

If these two factors aren’t balanced, we’re either Arrogant or Undervalued. Both of which will hold us back.

If we’re Arrogant, we might be able to open up doors by talking the talk, but when we can’t walk the walk, we’ll damage our reputation and won’t be able to deliver the results we want. In this situation, we need to focus our energy on developing concrete skills so we can actually deliver on the promises we make.

If we’re Undervalued, we’re not able to open doors by talking the talk, even though we’re able to walk the walk. In this situation, we need to develop the skill of selling ourselves. Getting ourselves into positions to leverage our skills is just as important as the skills themselves.

And if we’re Beginners or High Performers, we can pat ourselves on the back for aligning our confidence and competence correctly, but we must continue to push ourselves forward. As we improve our skills, we need to continue expanding the requisite self-confidence to go along with them.

Along the way, our confidence and competence will inevitably fluctuate, and we’ll become arrogant or undervalued, so we have to remain self-aware enough to identify these gaps and course correct along the way.

Ultimately, we want to continue improving in every area of life so we can talk the talk to open up any door we want and then walk the walk right through them.

Prompts

1. What quadrant do you fall in when you think about your life?

2. When you consider each of the most important areas of your life, which quadrant are you in in each?

3. What do you need to do to ensure your confidence is congruent with you comeptence in each area of your life?

Deep Dive

• The Confidence Gap by Russ Harris

  • A guide to overcoming fear and self-doubt using principles from Acceptance and Commitment Therapy.

Most decisions aren’t that hard. We choose the best option and move on.

But big decisions, like where to live and which job to take, are paralyzing in a way that daily decisions aren’t. These decisions touch every area of our lives, and once we make them, they’re extremely difficult to reverse.

Big decisions become even harder when we have all the options lead to great outcomes.

When one path is clearly better, the choice is still consequential, but it’s easier when we know what the “right” path is. When all of our options are promising, the choice is not only consequential, but we agonize over which path is the “right” path. There’s always something to wonder about, always a reason to second-guess whichever we choose.

Making big decisions is about making the “right” choice, but how we think about that choice afterwards is just as important.

Go Deep

The most costly error when making a life-altering decision is not going deep enough.

If we don’t carefully consider our options and what’s important to us, we risk going down the wrong path and living with the regret of making a big decision carelessly.

Deeply considering our options comes down to two things: defining the life we want to live and evaluating how each path will move us closer to or farther from our ideal lifestyle.

These questions are nearly impossible to answer in our heads.

Different options will impact different areas of our lives and create countless dependencies and scenarios that we can’t process and compare at once. To go deep and properly consider the consequences of each option, we have to get our thoughts on paper.

Writing down our thoughts (aka journaling) allows us to capture the complicated and incomplete ideas in our heads and transform them into concrete and meaningful words on the page. Writing forces clarity.

Once the pen starts moving, ambivalent feelings and inexplicable anxiety become clear and organized statements that we can review, compare, and understand.

Journaling lets us consider our options at a deeper level and gives us the information and understanding we need to choose the “right”path.

Commit and Accept

But, our job isn’t over when we decide. It’s just beginning.

The decision may work out, or it may not. It may unfold as expected, or look entirely different. Regardless of the outcome, we have to commit fully and accept what we chose.

This is especially hard when all our options were promising. Even small disappointments feel like evidence we that picked wrong path. When every option seemed like a great choice it’s easy to imagine parallel lives where the grass was greener on the other side.

As soon as we make the decision, we have to close the door on alternatives. Not because we definitely chose right, but because second-guessing is its own kind of losing. If we spend our energy on “what if,” we never fully commit to the life we chose, even if it was the right one.

Every big decision is made with incomplete information. We owe it to ourselves to go as deep as we can before choosing, but equally as important is accepting our decision with grace, committing to our new direction, and embracing whatever comes next.

Prompts

1. Think of a big decision you’re facing or have faced recently. Did you go as deep as you could before deciding? If not, what held you back?

2. Is there a past decision you’re still second-guessing? What would it feel like to fully close the door on the alternative?

3. When you’ve made a decision and things didn’t go perfectly, how did you respond? What does it look like for you to accept a choice with grace?

Deep Dive

• Thinking in Bets by Annie Duke

  • A guide to making decisions under uncertainty from a professional poker player.

Thanks for reading! I’ll see you next Sunday.

Kevin

It takes decades for one person to discover something new, but only a moment for millions to use it in their own lives.

What were once novel discoveries become common knowledge. Problems are solved not just for the person who did the work, but the solutions become instantly accessible and valuable to everyone else.

We face hundreds of problems in our lives every day, but most of them have already been solved.

Despite this, we choose to do the hard work of solving the problems from scratch instead of leveraging solutions that already exist.

Blazing our own trail

Our instinct is to assume our struggles are unique and forge our own path instead of following in someone else’s footsteps.

Many of the challenges we face, like losing weight, progressing our careers, parenting, or mastering hobbies, have all been solved by someone else before.

There are existing blueprints that have worked for countless others, but we start from scratch and accept the struggle because leveraging someone else’s solution to solve our own problems feels like cheating.

Our brains confuse effort with progress. If something is hard, it feels like we’re making progress, but we need to differentiate between problems that are worth our time and those that are not.

The only time we should be blazing our own trail is solving problems that are truly groundbreaking or unique to our individual situation.

If we’re chasing something that has already been accomplished by someone else, our best option is to use what they’ve learned and accomplish the same thing with significantly less work.

It may not feel as rewarding, but this frees up our time to work on the problems that only we can solve.

Evolving the problems we solve

There should be no shame in leveraging existing knowledge or systems.

We shouldn’t be worried that we’re not working hard enough. We should be worried that we’re not working on the right problems.

Software engineers don’t write code if they don’t have to. If an existing library or product accomplishes what they need, they copy and paste that code and move on.

They are ruthlessly efficient, so they can focus on the one thing that truly matters: writing code that solves a problem no one else has solved before.

There is nothing noble or admirable about making things harder than they have to be.

Once a problem is solved, it creates a new block of human knowledge that anyone can leverage. This knowledge is more accessible today than ever before. We should use it.

If we want to become better and make an impact on the world, we need to leverage existing solutions to maximize the time and energy we spend on problems only we can solve.

Prompts

1. What solved problems are you working on from scratch?

2. What unique problems are you solving that will help those around you?

3. If all of your current problems were solved, what would the next level of problems look like?

Deep Dive

• The 4-Hour Workweek by Tim Ferriss

  • The manifesto for eliminating and outsourcing unimportant work.

Thanks for reading! I’ll see you next Sunday.

Kevin

There is a common story arc among high-performing and business influencers.

They spent decades grinding to become the top of their field, only to realize everything they were sacrificing to accomplish this was making them miserable and slowly killing them.

Eventually, they have a moment of clarity and dramatically quit what they’ve dedicated their entire lives to. Then they have a crisis of identity and need to reinvent themselves. Ultimately, they learn from their mistakes and share lessons from their personal enlightenment about pursuing what they love, embracing a slower pace of life, saying no more, and making up for lost time with everything they sacrificed earlier in their lives.

Their stories are undoubtedly inspiring, and their advice is undeniably valuable, but it’s a lot easier to take things slow and pursue passion projects after spending decades becoming massively wealthy and building a reputation that opens up doors only the 1% can access.

It’s harder to embrace a slower pace of life without life-changing wealth or exclusive opportunities, but taking a sustainable and diversified approach to our lives doesn’t require the irreversible sacrifices that growth-at-all-costs does.

Our goal shouldn’t be to maximize growth that we know we can’t sustain. Our goal should be to become better without doing irreparable damage to ourselves or those we care about.

Quiet progress

Neither extreme is purely right or wrong, but going all in on one pursuit is certainly riskier. There is guaranteed sacrifice, but no guaranteed reward.

When we bet our entire lives on one thing, we drastically increase not only our risk of failure but also the likelihood we burn out.

Pursuing excellence in this way is like investing in one stock that’s returned 50% every year for the last 10 years. It seems like a sure thing, but that can change at any time.

Pursuing a well-rounded and slower life is like investing in diversified index funds: it’s boring and simple, but if we get started early and remain consistent, the returns from the compound interest after decades of focused effort are mind-boggling.

We can create the life we want without sacrificing everything and working ourselves to the bone, but creating this life will be slower, more intentional, and a lot less glamorous.

The hard part is not grinding through endless hours of work, battling depression or addiction, losing touch with family or friends, or any other catastrophic outcome common with an all-in approach. The hard part is staying patient, staying on the path, and avoiding the temptation to go all-in or blow all our hard work on a big bet.

This approach is hard to stick with because there’s no external validation. Everyone lauds the risk taker who doubles down when they have nothing left and miraculously comes out on top, but no one praises the quiet pragmatist slowly creating a life they love.

Maximum sustainable growth

The ironic part is that pursuing the slower path is just as, if not more, extraordinary than sacrificing everything to chase success.

The discipline, focus, and intentionality required to relentlessly pursue becoming better without sacrificing other areas of our lives are incredibly rare.

Investors care about “risk-adjusted returns” above everything else when considering investment strategies. The higher the return and the lower the risk, the better the investment.

Pursuing excellence, without leaving everything else behind, has lower returns but less risk. Selling out and sacrificing everything for a chance to be the best has a chance for much higher returns, but also much more risk.

We all have an insatiable desire to grow and progress our lives forward, but growth at all costs creates a high risk for burnout and requires irreparable sacrifices.

A slower approach eliminates these risks while still providing healthy returns.

We should not be chasing maximum growth at all costs in the hope that we might be able to cash in and relax one day.

Instead, we should pursue maximum sustainable growth. We should be pushing ourselves as hard as we can while still enjoying our day-to-day lives and maintaining a reasonable sense of balance.

We won’t be on the front page of the newspaper, but we will be happy.

Prompts

1. What is the pursuit in life that you’re betting the most on?

2. How are you diversifying your identity? Will you be left with nothing if your main pursuit fails?

3. What are you unwilling to sacrifice in the pursuit of becoming better?

Deep Dive

• The Case for Diversifying Your Identity

  • A quick read from Brad Stalberg on becoming more resilient.

Thanks for reading! I’ll see you next Sunday.

Kevin

We spend most of our time on autopilot doing things that are functionally important, but cosmically insignificant.

Every day we rush through meals, work, errands, TV shows, and scrolling on our phones until we realize it’s time go to bed and do it all again tomorrow.

We don’t really “do” anything, so it’s no surprise that we struggle to remember how we spent our time. We move through most days letting life happen to us without ever doing anything meaningful.

When we’re not intentional with our time, it feels like life is passing us by (because it is).

We all have a voice screaming in our heads saying, “do stuff! do something! do anything!”. That voice is suppressed by the convenience of consumption and socially acceptable platitudes like “there aren’t enough hours in the day”.

Every day, it becomes easier to do nothing, but inaction breeds anxiety. The more we suppress the voice urging us to “do stuff”, the more anxious we feel.

Inconveniencing ourselves

Our typical reaction to anxiety is stepping back and giving ourselves time to rest. Instead of going out and doing stuff, we retreat, build a plan, and try to think our way out of the problem.

Despite our instinctual reaction, inaction only digs us deeper into the same hole. The best way to take control of our lives and overcome anxiety is to do stuff.

We need to snap out of autopilot and do things that are meaningful and memorable.

A lunch with friends, a walk in a park, reading a great book, tending to a garden, or making a home-cooked meal are all that’s needed to add texture and meaning to our day.

In a world of routines where the path of least resistance is sitting on the couch with an endless supply of highly entertaining and personalized content, doing stuff is undoubtedly inconvenient by comparison.

We have to leave work early, go to bed late, or disrupt our routines in some way to replace what’s easy and safe with something worthwhile and memorable.

However, inconveniencing ourselves to engage in these simple, but meaningful experiences proves that we’re in control of our lives and doing things that are worth our time.

Doing stuff is what separates drifting from one day to the next from creating a life filled with rich and rewarding experiences.

If we’re not careful, we can live our entire lives without doing anything, but to enrich our lives and become better, we need to do stuff!

We need to get up and go places. We need to learn new skills, get outside, talk to people, create something, do something hard, and make progress on things that are important on the scale of weeks, months, or even years.

Become an author, not an actor

The key to a fulfilling life is doing stuff.

We owe ourselves more than clocking in and out of work just to sit around and wish there was more time in the day. We have to take advantage of the time we have by making intentional efforts to do stuff.

Our lives are nothing more than a culmination of what we’ve done. We can’t experience anything if we don’t do anything.

We need to do stuff that we’ll remember. Do stuff we’re proud of. Do stuff we don’t have time for. Make an effort to do something worthwhile and take action. We’ll remember it. It will feel good, and it will give us the push we need to do it again and again until we feel like we’re the authors of our own lives instead of supporting characters in a story we didn’t write.

Prompts

1. What is something you always dread and want to cancel but are always grateful for afterwards?

2. What meaningless activity can you give up this week to make time for doing something meaningful?

3. If you were the author of your own life, what “stuff” would you spend your time doing? How is that different than what you did last week?

Deep Dive

• The Art of Making Memories by Meik Wiking

  • How to Create and Remember Happy Moments

• Drink Coffee Do Stuff

  • A coffee shop in Tahoe and an incredible mantra to keep things simple and do stuff that we’ll remember

Thanks for reading! I’ll see you next Sunday.

Kevin

The Indiana University football team held the record for the most all-time losses to start this season.

Tomorrow, they are heavily favored to win the National Championship.

Indiana has gone from arguably the worst college football team in the country to making history because of one man: Curt Cignetti.

Cignetti is Indiana’s head coach. This is only his second year coaching Indiana, but he’s left a healthy resumé of successes in his decades-long career.

Throughout his time as a wide receivers coach, recruiting coordinator, assistant coach, and eventually as a head coach, Cignetti has always produced incredible results, but he’s never played by the rules.

Ignoring speculation

Indiana’s roster only has 4 top-ranked recruits compared to oppenents which often have more than 50, and yet, they are still winning by margins of 30 points or more.

Cignetti doesn’t care about vanity metrics or a player’s potential; he only cares about results.

Rather than focusing on the standard ranking system and metrics like 40-yard dash times, which project players’ potential, Cignetti focuses on on-field production.

He doesn’t gamble on the highest-ranked recruits coming out of high school. Instead, he finds unranked players who have quietly produced incredible results at smaller schools from the transfer portal. These players have more than potential, they have years of experience playing at a high-level and a proven track record of concrete results.

In addition to heavily weighing on-field performance, Cignetti focuses on unique characteristics for the players he recruits. Most coaches obsess over a player’s height, weight, and speed, but Cignetti cares more about ankle, knee, and hip flexibility. This ensures players can actually use their speed and size effectively.

Finally, he considers players’ character and conduct off the field. He is not willing to recruit an incredible player if they will cause problems in the locker room or elsewhere.

Cignetti’s approach is producing incredible results in the realm of college football, but it also provides us with a framework to create asymmetric results in other areas of our lives.

Obsess over outcomes

We will gain access to better opportunities and accomplish more in the long run if we focus on “production” instead of predictors of “potential”.

When we’re choosing between paths in our lives, we should always lean towards the opportunities that give us the best chance to produce meaningful and measurable outcomes.

It’s better to be a big fish in a small pond than a small fish in a big pond.

An all-star quarterback on a DII football team will have far more opportunity produce concrete results than a backup at a big-name DI program. A talented professional will make a huge impact at a small firm, but might not get a chance to contribute meaningfully at a large multinational firm.

Signals like rankings, prestige of a school or firm, and credentials or degrees are leading indicators that tell us we have the potential to create meaningful outcomes. Producing real work in the real world, even if it’s in a smaller environment, are lagging indicators that undeniably prove we have already created the outcomes that matter most.

Name brands and expensive degrees can open doors, but they don’t guarantee we can do the work. Rankings and titles sound impressive, but when the stakes are real, no one cares what our potential is; they care about what we’ve created, what problems we’ve solved, and what outcomes we’ve been responsible for.

Outcomes are the only thing that matter.

Chasing signals and status can open doors, but we have to produce measurable results to walk through them. Talking the talk doesn’t matter if we can’t walk the walk.

To craft the life we want and become a bit better each day, we can’t chase status or signals of potential. Instead, we must focus ruthlessly on developing valuable skills and using them to create an undeniable track record of results.

Prompts

1. What is one area of your life in which you’ve produced undeniable results?

2. Where do you see yourself falling into the trap of over-indexing on potential instead of production?

3. What is one skillset you can focus on in the next 6 months to create outcomes that will unlock new opportunities?

Deep Dive

• So Good They Can’t Ignore You by Cal Newport

  • Why Skills Trump Passion in the Quest for Work You Love

Thanks for reading! I’ll see you next Sunday.

Kevin

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I recently bought a record player.

It’s in my office, and I listen to records while I work. Unlike Spotify, which serves an uninterrupted stream of music, the record player scratches and the music stops every few songs.

Every time this happens, I walk away from my computer to flip the record. When I return to my desk, I realize I’m working on something unrelated to the project I started a few minutes prior, and switch my attention back to the original project

After repeating this pattern countless times, it’s become clear that the “inconvenience” of the analog experience is actually helping me overcome distraction and refocus my attention on what is most important.

The record player interrupts my flow, but it’s a flow of distraction. Without something to physically pull me away from my computer, I get lost in the frictionless distraction of the digital world.

Don’t fight a futile battle

When we step into the digital world, we’re immediately exposed to trillion-dollar companies and millions of people who have very different objectives than our own.

They are fighting to pull our attention to their content, their advertising, and ultimately use us to improve their bottom line.

There is no amount of discipline or willpower that can compete with the directed forces of millions of people and billions of dollars.

Trying to fight against the digital world with willpower or discipline is like showing up with a knife to a gunfight. Our brains can’t comprehend how powerful these forces are, so we’re wasting energy fighting against them.

An environment that’s one keystroke away from switching tasks and one click away from an army of people who want us to focus on their priorities instead of our own is not convenient; it’s counterproductive.

Instead of trying to overcome digital distractions, we should embrace analog experiences.

Friction creates focus

We can spend our energy trying to create friction in digital environments (screen time limits, grayscale filters, turning off wifi, etc.), but analog experiences already have the friction required for focus built in.

Journals and pens don’t buzz when a news article is published. Typewriters are for writing prose, not emails. Going on a phone-free walk forces us to think for ourselves instead of consuming ideas from others.

When we don’t have an endless supply of apps to check or content to consume, we’re forced to be present and direct our attention to the task at hand. We learn to sit with the discomfort of boredom and redirect our attention back to our work instead of seeking comfort by redirecting our attention to something else.

The more friction required to switch tasks or redirect our attention, the easier it is to stay focused and think deeply.

Going analog is the easiest way to create the friction needed to produce our best work and remove distractions.

If it’s important, make it analog.

Prompts

1. What is the most important work you do? How can you make it analog?

2. What digital distractions are you fighting against? How can you remove them instead?

3. Where can you introduce friction in your life to create more focus?

Deep Dive

• Stolen Focus by Johann Hari

  • An explanation of why we can’t focus and a guide to think deeply again.

• Freewrite

  • A modern-day typewriter for distraction-free analog writing.

Thanks for reading! I’ll see you next Sunday.

Kevin

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The biggest mistake we can make is pursuing the goals.

If we choose the wrong pursuits, success will move us farther away from the person we want to become, and failure will waste our time.

If we choose the right pursuits, even failure will move us closer to the person we want to become.

It’s easy to get caught up in exciting goals, but accomplishing something on its own is often hollow and disappointing. It brings us a fleeting moment of joy and pride, but once the achievement wears off, we’re left with the sinking feeling of what to do next.

Goals are useful for directing our actions, but they are not worthwhile on their own. The point of goals is not to accomplish an arbitrary objective. The point of goals is to move us closer to living our ideal lifestyle and becoming a better person.

Beginning with the end in mind

A life well lived is not a random collection of trophies, titles, and accomplishments. Nor is it a checklist of daily habits or routines.

A life well lived is doing what we want, when we want, with whom we want, for as long as we can, while becoming a bit better each day along the way.

When planning for the upcoming year, we should start with the life we’d like to live instead of starting with goals we’d like to accomplish or habits we want to maintain.

We might want a promotion at work, only to realize that after we “accomplish” our goal, we’re working more hours, with more stress, and spending less time with our family. If we begin with our ideal lifestyle instead, we could have negotiated a raise with the same title, so we can progress our career forward without sacrificing the quality of our day-to-day lives.

Focusing on goals and habits before defining our ideal lifestyle is like getting in the car and driving for hours before we decide where we want to go.

A framework to become better

Goals and habits are still powerful tools to become better in the upcoming year, but they shouldn’t be our starting point.

Instead, we should start with our vision for a random Tuesday.

This allows us to define and understand what our ideal lifestyle looks like. The more detailed we are about what we’re doing, who we’re spending time with, and how we feel, the more likely we are to make this vision a reality.

Visualizing our ideal lifestyle forces us to start with our desired result and use goals and habits as tools to build the life we want, instead of chasing goals and implementing habits that create a lifestyle we never considered.

To create our ideal lifestyle, we should define the following in each area of our lives:

1. Desired Outcome - a detailed vision of our ideal lifestyle in a specific area of life

2. Measurable Goals - quantifiable milestones that are met if we’re living our ideal lifestyle

3. Daily Habits - actions that contribute to achieving our measurable goals

For example, if our desired outcome is to feel effortlessly strong and energetic, then our goals would be squatting 2x our bodyweight and sleeping for an average of 8 hours each night. Our habits to achieve these goals would be weightlifting 3x per week and getting into bed before 10pm every night.

This framework makes everyday life our north star, not accomplishments or external titles. It transforms goals from hollow check boxes to meaningful milestones so we can measure meaningful progress and stay motivated.

If we’re not careful, we can optimize our entire life around high-performance habits and exciting goals, only to realize we sacrificed all our time and energy to trap ourselves in a life we don’t want to live.

Creating the perfect routine and accomplishing exciting goals only matter if they create a life we’re excited to live every day.

Prompts

1. Consider a random Tuesday a few years into the future. If everything goes right, what does your ideal Tuesday look like? What time do you wake up? What do you do during the day? Who do you get to spend time with? The more detail you provide, the better.

2. What measurable goals need to be true in each area of your life to live out your ideal lifestyle?

3. What habits do you need to integrate into your daily routine to make meaningful progress on these measurable goals?

Deep Dive

• Start with Why by Simon Sinek

  • A compelling case for focusing on why we’re doing things instead of what we’re doing.

Thanks for reading! I’ll see you next Sunday.

Kevin

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91% of New Year’s Resolutions fail.

The reason is not a lack of motivation or time. We all have an innate desire to become better, and even when we’re at our busiest, we make time for what’s most important.

The number one reason we fail is that we set unrealistic and vague goals.

We become excited and idealistic when we’re building a vision for the upcoming year, but when it’s time to take the first steps, we don’t know where to start. Within a few weeks, we’re left feeling frustrated and hopeless and abandon our goals altogether.

The perils of “should”

We gravitate toward unrealistic and generic goals because we’re lazy.

Instead of taking time to consider what we want to pursue, we’re caught in the easy trap of chasing what we feel like we “should” accomplish. Our list of resolutions becomes indistinguishable from the next person: “lose weight”, “more time with family”, “travel”, and “eat healthy”.

We struggle to follow through because they’re not personally meaningful. They sound good, but we don’t know where to start, and we don’t care if we achieve them or not.

Goals like this are about as exciting as bland corporate mission statements and quarterly objectives. They are good goals in an abstract and generic way, but they mean nothing to us, so we’re not willing to invest the energy required to see them through.

This pattern is particularly insidious when we repeat it over and over again each year, effectively teaching ourselves that we can’t accomplish anything, making it harder and harder to achieve something worthwhile each year.

To break the cycle, we need to look back and review the past year before looking forward and creating goals for the upcoming year.

The annual review

Review comes from a Latin word that means “to see again”.

When we take the time to “see” the previous year again, we learn things about ourselves. Reflecting on how we spent our time gives us the perspective we need to identify our patterns, values, and identity.

With a better understanding of ourselves, we can create better goals. Instead of blindly choosing goals based on what it feels like we “should” be pursuing, we can align our goals for the upcoming year with who we are and what’s important to us.

We’re much more likely to accomplish goals that are personally meaningful than goals that sound good at a cocktail party.

Trying to become better is an innate human pursuit, but if we don’t review and reflect on the past year, then we’ll be choosing generic goals and setting ourselves up for failure.

To become better in 2026, we must start with an honest and structured review of 2025 to create goals that inspire us to take action.

Only after we understand ourselves can we make meaningful progress on the pursuits in our lives that actually matter.

Prompts

1. What did I enjoy most last year? How can I do more of it this year?

2. What did I hate most last year? How can I remove that from the upcoming year?

3. When I was at my best last year, I was usually…

4. When I was at my worst, it was usually because…

5. What did I continually gravitate towards without external pressure?

6. What did I continually avoid that I believed was important? Were there consequences for avoiding it?

7. What did I do last year that aligned with my values?

8. What did I do last year that was out of alignment with my values?

Deep Dive

• Conducting an Annual Review - Tim Ferriss

• Annual Planning Guide - Sahil Bloom

Thanks for reading! I’ll see you next Sunday.

Kevin

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When I was 13, I used to play ping pong against my Dad every night.

After dinner, we would head out to the garage and buckle down for a 3-game series that would inevitably extend into at least 5 or 7 games as we kept playing.

For years, I would always lose. I felt like I was the better player, but could never come out on top. As a sore loser, I channeled all my frustration into trying new strategies to win. I tried different serves, crazy spin shots, and hitting it as hard as I could into the corners, but I still couldn’t beat him.

Finally, I stopped trying to win and lightly hit the ball back into the middle of the table every shot as a form of protest. After a few volleys, my Dad hit it into the net, and I won the point. I did it again, and he hit it off the back of the table.

After a few points, I was ahead and eventually won the game. I did the same thing the next game and won that one too.

Minimizing mistakes > maximizing winning

I accidentally stumbled across a strategy that would allow me to dominate my Dad in ping pong for years to come: just don’t lose.

Instead of trying to hit crazy shots and make my Dad miss, all I had to do was get the ball over to the other side of the table and let him make a mistake. I didn’t have to “win” a single point to win the game; I just couldn’t lose.

There are no style points or bonuses for hitting a “better” shot. The only thing that matters is not losing. The fancier I got, the more likely I was to lose the point.

This would never work if I were playing competitively, but it gets the job done against 90% of the ping pong playing population and most other games in life.

A winning record with worthwhile pursuits

The worthwhile pursuits in our lives don’t require high-level excellence. The harder we try, the more likely we are to make mistakes or burn out.

Staying fit, eating healthy, nurturing relationships, and progressing our careers are not games that we need to win. They are games we just can’t lose. All we need to do is show up every day and do the equivalent of hitting the ball over the net.

It doesn’t have to be pretty, it doesn’t need to be impressive, and it’s probably not all that exciting on a day-to-day basis, but if we consistently dink the ball back over the net for every day, we will have a winning record in all of the most important areas of our lives.

Prompts

1. In each of the worthwhile pursuits in your life, what does simply hitting the ball back over the net look like each day?

2. Where is trying to win backfiring for you?

3. In what ways have ordinary, but consistent actions created extraordinary results in your life?

Deep Dive

• Tiny Habits by BJ Fogg

  • Advice from a Stanford behavior scientist on building lasting habits with small changes.

Thanks for reading! I’ll see you next Sunday.

Kevin

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Fighting for control is a losing battle.

No matter how hard we try or how many variables we remove, we cannot control what happens to us.

We can (and should) plan how we want to navigate our lives, but as soon as we take our perfectly crafted plan into the real world, the unpredictability of everyday life will thwart any chance of executing it as we expected.

How we deal with this lack of control determines how we feel about our lives and what we can accomplish.

Thriving in the ocean

When we realize we don’t have control, it’s easy to give up entirely. If life is going to knock us down no matter how hard we try, what’s the point of trying at all?

Apathy and nihilism are logical but dangerous responses to the lack of control we have in the world, but perfectionism is equally as damaging. Obsessing over things we can’t control leads to chronic stress and disappointment.

Navigating the world is a lot like navigating the ocean. It’s unpredictable and dangerous, but there are patterns and best practices that make a huge difference. They don’t let us control the water, but they let us swim without drowning.

Trying to control the ocean leads to over-exhaustion and drowning. Giving up means we’ll float out to sea.

To thrive in the ocean, we need to accept and respect what happens to us while maintaining control of how we respond.

We have to surf

No one embodies this combination of personal responsibility and acceptance better than surfers.

Surfers do not try to overpower the ocean or sit around letting the current take them.

They meticulously observe their surroundings and diligently paddle themselves into the right place at the right time so they can ride the waves the ocean gives them.

Surfing is not exerting control over the ocean or passively waiting for waves to come. It’s a deliberate and focused effort to find the best position to take advantage of something that’s completely out of our control.

This is how we should navigate our lives. We have to surf. We can’t control what happens to us, but we can’t give up.

Instead, we need to put ourselves in the best position to take advantage of the opportunities that come our way.

Some days, the waves will be small. Others, they’ll be huge. Some days, we’ll be the only ones out there catching all the waves for ourselves. Others, it will be so crowded we can’t even catch one. Some days, we’ll get pounded into the sand over and over again. Others, we’ll effortlessly glide across the waves.

We’ll never be able to control what happens to us, but we can control the position we put ourselves in.

Life is random and uncontrollable, but the more effort we spend on putting ourselves in the right position, the more opportunities we’ll have to do something great.

Prompts

1. Are you more likely to give up or try to control everything? What are the consequences of this?

2. What’s something outside of your control that’s been frustrating you? How can you focus on putting yourself in a better position instead of trying to take control?

3. What does surfing through life mean to you?

Deep Dive

• Antifragile by Nassim Taleb

  • An investigation of things that thrive in chaos and uncertainty.

Thanks for reading! I’ll see you next Sunday.

Kevin

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Many cliches are true. That’s why we keep saying them over and over again.

Missing the forest for the trees, working in the business instead of on the business, or getting stuck in the weeds are all timeless cliches that capture a serious problem: daily minutiae getting in the way of important long-term pursuits.

We can become so focused on our day-to-day responsibilities that we completely forget the reason we’re doing them in the first place. These daily actions start as a concrete way to make progress in an important area of our lives, but over time, the inputs diverge from the outputs.

In many cases, actions that once created meaningful progress are now preventing us from moving forward. Common examples include

• Being so busy working, we don’t have time to focus on our careers

• Spending countless hours with our spouse, but never truly communicating

• Doing the same workout every day, without considering what our long-term health goals are

There are countless different ways we can miss the forest for the trees and get so focused on the specifics that we completely lose sight of the bigger picture.

To avoid this trap, we need to create space to reflect and plan. We need to zoom out and recalibrate.

Zooming out

If we don’t create time and space to zoom out, it’s only a matter of time before we get lost in the weeds. We become so focused on our actions that they begin to obscure our true objectives.

To make sure our actions are serving our long-term objectives, we need to zoom out beyond our day-to-day habits and responsibilities and consider two things. First, we need to define (or redefine) what our goals are in each area of our lives. Second, we need to decide if the actions we’re taking today are supporting this vision or holding us back.

This ensures what we’re doing today is aligned with where we want to go and who we want to be tomorrow, but when we stop to reflect, it feels counterproductive.

It’s uncomfortable when we’re not actively working on anything, but we need to periodically stop to recalibrate our vision for the future and make sure our actions are aligned with our objectives.

We need to create regular space in our lives to ignore our to-do lists and think about the future instead.

Creating space

Saying that we need to reflect and consider a longer time horizon is one thing, but actually doing it regularly is much more challenging.

When life is busy, and we have a million things to get done, ignoring everything urgent to sit down and ponder the future doesn’t feel very helpful. It ends up being the first thing we skip to make time for everything else.

But to ensure everything we’re doing is actually worthwhile, we need to create space to zoom out and protect that time fiercely. It doesn’t matter how much we get done unless the work that we’re doing is actually moving us closer to the person we want to become.

Being busy feels productive, but if we don’t align our activities with our objectives, then we’ll never make any meaningful progress on the things that matter most.

Prompts

1. What everyday activities have started to hurt your long-term objectives instead of helping?

2. How can you create space in your week to reflect on a longer time horizon?

3. What is the cost of being busy?

Deep Dive

• Stillness Is the Key by Ryan Holiday

  • Holiday argues that the common trait amongst all great thinkers, artists, athletes, and visionaries is stillness.

Thanks for reading! I’ll see you next Sunday.

Kevin

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Did you make meaningful progress on a worthwhile pursuit today?

This question cuts through the noise and forces us to be honest about how we spend our time each day.

If we’re not intentional with our time, we default to moving through the day on autopilot, filling idle time with mindless scrolling or consumption. Letting days slip through our fingers leaves us feeling guilty and frustrated for wasting the limited time we have.

We should ask ourselves this question each day to keep us honest, force us to reflect on how we spend our time, and decide if our routines and habits are progressing us forward or holding us back.

Asking this question also forces us to define what a worthwhile pursuit is and what it means to make meaningful progress.

Defining worthwhile and meaningful

What makes a pursuit worthwhile isn’t how we feel about it or what area of life it’s focused on. A worthwhile pursuit is something that helps us become a better person.

Worthwhile pursuits can never be accomplished, and we would still invest our time in them if no one else were watching. Becoming a better parent is a worthwhile pursuit, but getting a promotion at work is not.

Defining these pursuits is important, but we also need to make sure we’re progressing ourselves forward within the context of each pursuit.

If all we do is clock in and clock out, it will eventually lead to some improvement, but the progress will be trivial. We can make progress just by showing up, but it won’t be meaningful.

Meaningful progress is taking intentional action to achieve specific and non-trivial advancements in our abilities.

Showing up at the gym each day is a step in the right direction, but to make meaningful progress, we need to intentionally execute a training plan that delivers the specific results we’re looking for.

With a better understanding of where and how we should be spending our time, we can audit each day to spend more time on intentional efforts to become better instead of letting each day slip by in a deluge of mindless consumption.

Accumulating purposeful habits

When we first start incorporating these intentional efforts into our day, it will be difficult to pull ourselves out of the rut of our normal routines.

But if we continue to ask ourselves if we’ve made meaningful progress every day, this prompt will catalyze us to take actions that create meaningful progress a part of our daily routine.

If we stay consistent, our default behavior will turn from mindless consumption to intentional improvement. Over time, we can accumulate new routines and habits in all the different areas of our lives until our autopilot behavior makes us a better person.

The more we can track these efforts and reward ourselves for progress, the more it will stick. Our days will stop feeling wasted and start feeling inspiring.

Instead of lying in bed at night, wondering how we wasted another day, we can sleep soundly knowing that we’re becoming better.

Prompts

1. Create a list of 5 things that count as “making meaningful progress on a worthwhile pursuit”. How can you make time to do at least one of them every day?

2. What are your status quo habits that help you make meaningful progress on worthwhile pursuits?

3. What is one new intentional daily action that you’re working on incorporating into your daily routine to make meaningful progress on a worthwhile pursuit?

Deep Dive

• Atomic Habits by James Clear

  • The best-selling book on habits and behavior change.

Thanks for reading! I’ll see you next Sunday.

Kevin

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We can’t change what we won’t accept.

The most damaging character flaws are the ones we’re most likely to ignore, but we can’t change them until we accept reality.

Cal Newport, the author of Deep Work and Slow Productivity, frequently discusses the phenomenon of frantic knowledge workers desperately trying to optimize elaborate task management systems or blame external forces instead of facing the reality that they have too much on their plate.

To overcome endless busyness, Newport encourages what he calls “facing the productivity dragon”. He suggests taking a step back from the day-to-day grind to take stock of everything that’s on our plates and make a complete list of our responsibilities and how long everything will take.

There’s usually not enough time in the day to do everything we’ve agreed to. Facing the productivity dragon means pausing to understand and accept the reality that we can’t continue with the same approach. We must make a change.

This stark reality is scary, disappointing, and discouraging, but identifying it and creating a realistic plan to deal with it is necessary to do our best work.

Newport speaks of this idea in the context of professional productivity, but we all have dragons we need to face in different areas of our lives.

Accepting reality

We all have something we need to fix in our lives, and we know how to do it, but we don’t.

In today’s world, a lack of information or understanding is no longer an excuse.

In moments, we can find all of the information we need to improve any area of our lives. We can even find or create personalized step-by-step guides and tutorials, or connect with a real person who has done what we want to do with a few clicks.

The reason we don’t address these things is that trying to fix them requires that we accept the fact that our approach isn’t working. To make a change, we need to face our dragon, accept that what we’re doing today isn’t working, and admit that it’s our fault.

Only after we face reality and accept ownership can we begin to implement all of the information and guidance we have available to fix it.

Becoming better

In most cases, the hardest part of facing our dragons is not adding or removing the one behavior required to fix the problem. The hardest part is adapting all of the other areas of our lives to make sure that change sticks.

Improving our diet isn’t as simple as eating different foods. It requires that we reevaluate our exercise routine, social calendar, daily schedule, and emotional relationship with food. What seems like a simple habit change on the surface is actually a deep and complicated web of transformation.

We’re not just changing our lifestyle, we’re changing our identity.

The reason we don’t fix these problems even though we’ve known about them and dealt with the consequences for years is that it’s easier to maintain our identity and live with the consequences of a damaging habit or character flaw than it is to change our identity and become a better person.

To make meaningful progress towards becoming a better person, we have to accept that we’re not the best person we could be today. That’s a difficult thing to admit.

Facing our dragons is intimidating. It’s an incredible amount of work for an uncertain outcome, but it’s the only option to become better.

We can continue to ignore the glaring holes in ourselves and accept the consequences, or face our dragons, accept reality, and do the work to become better.

We all have something we need to fix. We don’t need a better plan, better timing, or more information; we need the courage to face it and accept the person we become.

Prompts

1. What does facing your dragon look like? What is the reality you need to accept?

2. What’s the one thing you need to fix?

3. How will your life improve if you fix it? What happens if you continue to do nothing?

Deep Dive

• Facing the Productivity Dragon - The Deep Questions Podcast

  • A guide to “facing the productivity dragon” and fixing what’s broken in our lives.

Thanks for reading! I’ll see you next Sunday.

Kevin

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Endurance athletes obsess over their pace.

Minutes per mile, miles per hour, pedal strokes per minute, and many others are critical metrics for judging effort and performance.

When an athlete has a complete understanding of their capabilities, they know how long they can sustain different paces. This knowledge gives them the ability to run their own race and pace themselves to get the best performance given their current level of fitness.

Pacing is powerful information in the world of endurance sports, but we don’t always have the same knowledge and understanding of how to pace other areas of our lives.

Without a clear understanding of what we’re capable of, it’s harder to run our own race, and we fall back on comparing ourselves to others, giving up before we reach our potential, or burning out too soon.

To properly allocate our talent and effort, we need a deep understanding of what pace we’re capable of in each area of our lives.

Too fast or too slow

Our default tendency when searching for the right pace is to look at what others are doing.

Invariably, the pace others are performing at will be different than what’s optimal in our own lives. More than likely, the people we choose to emulate are blindly following someone else who also hasn’t thought critically about their pace for their pursuits.

Copying someone else’s pace in life is as likely to succeed as showing up to a marathon and choosing someone at random to follow for the whole race. They may have a similar level of fitness to us, but in all likelihood, we will end up running much faster or slower than we should.

Just as detrimental is pushing ourselves too hard too soon. Whether rooted in excitement or insecurity, if we come out too hot, it’s only a matter of time before we burn ourselves out.

There are no trophies for completing the first half of something faster than everyone else if it burns us out and prevents us from finishing the initial objective.

The most insidious pace is not moving fast enough or not moving at all. Often rooted in fear or uncertainty, if we never push hard enough, we’ll never see what we’re truly capable of.

Not pushing hard enough or never trying something at all is such a common regret at the end of our lives that it’s become a cliché.

If we can’t push too hard and we can’t take things too slow, then the best thing we can do for ourselves is find a pace somewhere in the middle. The ideal pace is one that we can maintain for a long period of time, but also pushes us to create results we’re proud of.

Sustainably aggressive

Two people with the same talent and effort will produce different results if they work at different paces.

Developing talent and learning to work hard are prerequisites for creating incredible results, but the pace at which we pursue these results is what really matters.

In the worthwhile pursuits we choose for ourselves, we should aim for a pace that is aggressive but sustainable. It should be something we feel confident we could continue indefinitely, but if we pushed a little harder, we would begin to burn ourselves out.

As we become more comfortable with this pace and get closer to our objectives, we can begin to push harder and slowly improve our optimal pace of performance.

The worst things we can do are push too hard too soon or never push ourselves at all, but if we can continuously maintain a pace that’s sustainably aggressive, we will be able to achieve incredible things for decades to come.

Prompts

1. In what areas of your life are you moving too fast? In what areas are you moving too slow?

2. What is a sustainably aggressive pace for you in your most important pursuit?

3. Which areas of your life are worth a sustainably aggressive pace? Are there any areas in which you’re allocating too much energy?

Deep Dive

• Slow Productivity by Cal Newport

  • A guide to finding a sustainable pace to create incredible results.

Thanks for reading! I’ll see you next Sunday.

Kevin

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Hard work is required to create a fulfilling life, but if we never stop to enjoy it, there’s no point in working so hard. Similarly, if all we ever do is relax, we won’t have anything worth enjoying.

We know we need a foundation of balance between hard work and leisure, but choosing the right path at the right time and feeling confident in our choice is much easier said than done.

When we choose to push ourselves to create the life we want, it feels like everyone else is sitting around enjoying themselves, and we’re missing out.

When we choose to enjoy ourselves and relax, it feels like everyone else is outworking us and getting ahead.

There is no one-size-fits-all balance of hard work and leisure, but we can become smarter about when we choose to push forward and pull back by identifying which season of life we’re in.

Seasons of life

If we’re young and single, we’re in a very different season of life than if we’re middle-aged with kids, but seasons of life occur on multiple timescales. There are macro-seasons of life that occur at the scale of years or decades, and there are micro-seasons of life that affect us on shorter time scales like injuries, breakups, moving, or the weather.

In the face of all this complexity, it’s tempting to choose a simple time-based heuristic for balancing hard work and leisure like “lock in Mon-Fri and enjoy the weekends” or “Dry January”, but these fail us in the long-term because they can’t adapt to the variance we experience from overlapping timescales.

Seasons layer on top of each other and push us in different directions at the same time. This makes it impossible to predict or plan when we should push hard to create the life we want and when we should step back to enjoy the fruits of our labor.

Instead, we should assess what season of life we’re in every day and adapt our long-term plan based on how we’re feeling, the same way athletes adjust their training plans to how their body feels on a given day.

To make meaningful progress toward worthwhile pursuits, we need to adjust our plan to our season of life, and we need to define what “enough” means for us.

Defining enough

Defining what “enough” means to us is one of the core challenges in deciding when to push forward and when to pull back. We can define “enough” as simply as meeting our basic needs or as grandly as creating a lasting legacy.

No definition is right or wrong, but if we don’t understand our version of “enough”, comparison clouds our judgment. If we’re unclear about what’s important to us, when we see others working harder than or relaxing more than us, we always feel like we’re making the wrong choice.

Understanding when to work hard and make sacrifices and when to relax and enjoy ourselves makes life more fulfilling. It allows us to work hard without burning out and enjoy our downtime guilt-free.

Prompts

1. What is “enough” for you? Do you need to raise your bar? Or lower it?

2. What season of life are you in right now? Does it make sense for you to push harder or pull back?

3. When you’re firing on all cylinders, what does a day look like where you’re pushing yourself forward? When you’re not at your best or you’ve earned time to relax, what does a day to recharge and enjoy the fruits of your labor look like?

Deep Dive

• The 5 Types of Wealth by Sahil Bloom

  • A simple guide to defining and measuring what’s important in your life.

Thanks for reading! I’ll see you next Sunday.

Kevin

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Effort only matters if it’s applied to the right things.

If we’re not focused with our action, it’s easy to waste our time and energy on things that feel impactful but don’t move us forward in a meaningful way.

Optimizing wastes our time in a uniquely insidious way; it makes us feel good and earns us praise, but it doesn’t make us any better. Building an elaborate task management system is fun and challenging, but it doesn’t help us complete the tasks on our list. The basics are boring but impactful, and optimizing is fun but inconsequential.

Building an elaborate training plan and buying new sneakers are way more fun than waking up early to run in the rain, but they still make us feel like we’re making meaningful progress as a runner. Rather than focusing our efforts on the difficult and boring work of building foundational skills, we’re often caught in a cycle of chasing fun but ultimately useless optimizations.

Optimizing before we master the basics is like polishing a car without an engine. It might look great sitting in the driveway, but it can’t accomplish the only thing that matters.

We want results but we chase dopamine

Professionals shouldn’t build elaborate workflows or AI agents to automate their work before they master the work themselves.

Golfers shouldn’t waste time and money on expensive club fittings and new technology before they learn to strike the ball correctly.

Authors shouldn’t obsess over marketing, formatting, and cover art before they sit down and write a book.

Avoiding seed oils isn’t going to change anything if we’re eating cookies and candy all day.

How we exercise doesn’t matter until we do it consistently.

If we step back to think about becoming better in the context of worthwhile pursuits like our careers, families, exercise, or hobbies, it’s obvious consistent effort directed at mastering the basics is the only way to achieve the results we want.

But in the busyness of everyday life, the bigger picture fades away and the temptation of spending our time on something that provides a quick hit of dopamine outweighs the often boring and grueling work required to make meaningful progress. We end up getting stuck in the same spot because we’re spending all of our time trying to run before we’ve learned to crawl or walk.

Optimizing a broken system gives us the feeling of making progress without the results.

Earn the right to optimize

Rather than viewing optimization as just another piece of any worthwhile pursuit alongside the foundational actions that progress us forward, we should treat optimization as a reward for ourselves once we’ve mastered the basics.

Before we go down the rabbit hole of endless optimization, we need an unshakeable foundation of skills and expertise.

It doesn’t matter how elaborate or elegant our optimizations are if we’re not capable of the basics that move the needle.

Once we’re consistently making meaningful progress towards a worthwhile pursuit, then we can begin to optimize our process, strategy, and systems to make more meaningful progress.

If we treat optimization as a reward for mastery, then we can ensure our efforts aren’t wasted.

Prompts

1. What optimizations are you focused on that are wasting your time?

2. What are the foundational actions you need to take every day to move the needle forward on what matters most?

3. What fun optimizations can you use as a reward for hitting your next big milestone?

Deep Dive

• Chop Wood Carry Water by Joshua Medcalf

  • A story about falling in love with the process.

Thanks for reading! I’ll see you next Sunday.

Kevin