Will Igor Take a Gap Year? Wrestling with Dragons and Dreams

personal , gap-year , decision-making , life-planning , how igor ticks

Done right, a gap year isn’t a year off; it’s a year on — intentional investment in health, relationships, and mastery while you still have the capital to invest. Think of it as pursuing a PhD in Life Optimization, making deposits that compound for decades. A gap year is one of those uncharted spaces—seductive when discussed longingly over a beer, terrifying when holding a resignation letter outside your boss’s office. Early maps warned: “HC SVNT DRACONES.” Here be dragons. I’m mapping them in real time: the Scarcity Dragon whispering you can’t afford it, the Entropy Dragon promising you’ll decay without structure, and the Squander Dragon insisting you’ll waste this precious opportunity. But these dragons guard treasure — the chance to invest in what truly matters while you still have the capacity to do so. This is the map of how to tame them.

This sits next to the gap year paradox: same terrain, closer camera.

Loading (/gap-year)

Is Igor really gonna quit his job and take a gap year?

When I started at Meta in March 2020, my plan was to take a gap year after my Meta stock vested in 2024. After all, I had five job offers in hand, including competitive offers from Google, Meta, and several mid-sized companies. But today’s job market is much scarier than pre-COVID 2020 — it’s become downright dicey out there.

Life is more than money, and to remind myself to broaden my perspective it’s helpful to imagine things I may lose.

What if in 10 years:

  • My kids no longer live at home
    • 100% probable (or so I hope)
  • My health and cognitive abilities have declined
    • 100% probable (unless we get some awesome new drugs)
  • I have serious health problems
    • 30% probable (hymn, I should look for actual probability)
  • I am no longer alive

If Igor could retire today, would he?

I often repeat “I’d do 80% of my job for free, but I don’t get to do that 80% without doing the last 20%”, so retirement doesn’t especially excite me.

That said, I also repeat no one ever said they wished they worked more on their deathbed. Especially when family time is sacred, and work eats up a lot of energy. When there’s no incremental family time possible, I’m happy to (and probably prefer to) work, but I’m not there in this chapter of my life.

Looking ahead from 2025 (I’m 47 now), I see three distinct phases:

Phase 1: With Zach and Amelia Home (3 years, ages 47-50)

  • Both kids still living at home
  • Maximum family time opportunity
  • Work flexibility most critical

Phase 2: With Amelia Home (4 years, ages 50-54)

  • Zach off to college, Amelia still home
  • Transitional period with one child
  • Balancing independence and presence

Phase 3: Empty Nest (ages 54+)

  • Both kids launched into their own lives
  • Time to work intensively again
  • Different kind of fulfillment and focus

In Phase 3, I anticipate wanting to work extensively - but Phases 1 and 2 represent irreplaceable windows for deep family connection.

Hey you’re not talking about Tori, doesn’t time with her matter?

It certainly does, but Tori needs her own time, and our relationship is set up where we don’t need a ton of time together.

Loading (/tori)

Hey don’t you want to travel?

Not really my thing, I’m more excited by production and self improvement than consumption.

TODO: Add content on production vs consumption

Why Open the Dragon Box? The Treasure Worth Fighting For

The gap year isn’t about escaping work - it’s about making capital investments while you still have the capital to invest. At 47, I have a unique convergence of resources that won’t last forever:

Peak Family Opportunity: Both kids still at home for 3 more years. These aren’t just any three years - they’re the last three years. The difference between being deeply present versus peripherally available during their transition to adulthood is irrecoverable.

Peak Physical Capability: At 50, I still have the strength and energy to build health infrastructure that will pay dividends for decades. Every year I wait, the return on health investment diminishes. The difference between starting kettlebells at 47 versus 57 isn’t just 10 years of practice - it’s the difference between building strength versus managing decline.

Peak Cognitive Ability: The capacity to master entirely new domains - AI, content creation, building products - while neuroplasticity is still high. The gap between learning at 47 versus 57 isn’t just speed; it’s the difference between intuitive mastery and surface understanding.

This isn’t a year off - it’s a year ON. A year of intentional investment in three types of irreplaceable capital:

Health Capital: Building the habits, routines, and physical infrastructure while you have energy, not when you’re desperate. This is the difference between investing in prevention versus paying for treatment. At 50, you can still build muscle, improve cardiovascular health, and establish patterns that will carry you through decades. This window closes.

Relationship Capital: Being truly present for the finite time with family. Not just physically present while mentally at work, but fully available - emotionally, intellectually, spiritually. The kind of presence that creates memories, builds trust, and establishes you as the safe harbor your children will need as they navigate adulthood. You can always make more money; you can never make more time with your kids.

Mastery Capital: Deep diving into new domains without the surface-level learning that deadline pressure creates. Real mastery - the kind that lets you see patterns, make connections, and create novel solutions - requires sustained focus without arbitrary time constraints. The difference between “I played with AI” and “I mastered AI” is the difference between consumption and creation.

But dragons guard this treasure. They whisper fears to keep you from claiming what’s yours:

  • Scarcity says you can’t afford it (but you can)
  • Entropy says you’ll waste it (but you won’t with structure)
  • Squander says it won’t matter (but it will to the people who matter)

The real risk isn’t facing the dragons - it’s letting this window close unopened. In 10 years, you won’t remember the meetings you missed or the promotions you didn’t get. But you’ll remember whether you were there when your kids needed you, whether you built the health to enjoy your 60s and 70s, whether you took the shot at mastery when you had the chance.

The dragons are real. The fears are valid. But the treasure they’re guarding - the chance to invest in what truly matters while you still have the capacity to do so - is worth the fight.

Work will always be there. This window won’t.

The Three Ancient Dragons: What Work Kept in the Box

Work doesn’t solve your existential fears - it just keeps them locked away. The gap year opens the box, and three ancient dragons emerge to test you. These aren’t enemies to defeat but fundamental forces of the universe that must be understood, respected, and ultimately tamed.

The Scarcity Dragon

“There will never be enough”

This dragon feeds on resource anxiety. At work, the biweekly paycheck kept it sedated, letting you ignore its existence. Now it whispers constantly about market crashes, unemployability, and dwindling reserves. It makes every expense feel like bleeding out, every market dip feel personal, every purchase a threat to survival.

When you had a steady paycheck, market fluctuations were abstract background noise - you weren’t drawing from investments, so volatility didn’t matter day-to-day. But during a gap year, the dragon transforms the market from a distant abstraction into a daily anxiety generator, making you hyperaware of every percentage point change in your portfolio.

The Entropy Dragon

“Everything tends toward disorder”

This dragon embodies the second law of thermodynamics applied to your life. Without work’s external structure forcing order, everything naturally decays - your body, your habits, your relationships, your skills. It’s not just stagnation; it’s active degradation. Entropy always increases in a closed system, and without the energy input of external obligations, you are that closed system.

At work, deadlines create artificial scarcity that forces efficiency. Without external constraints, this dragon ensures tasks expand to fill available time - what should take 2 hours somehow takes all morning. It whispers: “You have all day, so why rush?” The result: a slow drift into inefficiency that makes you feel simultaneously busy and unproductive.

The Squander Dragon

“You will waste this precious opportunity”

This dragon feeds on the fear that you’ll misuse this rare gift of time and resources. Without external metrics of productivity, how will you know if you’re succeeding? It whispers about Netflix binges, aimless days, nothing to show for it. You’ve been given a winning lottery ticket - the convergence of health, wealth, and family presence - and you’re going to waste it on… what exactly? The dragon asks: “What if you look back in a year and realize you squandered the very opportunity you sacrificed so much to create?”

How Work Kept the Dragons Boxed

Work provided three critical pieces of dragon-management infrastructure that you never realized you depended on:

Free excuses for neglecting yourself and your relationships: “I’m too wiped out from that presentation to work out” or “I’ll start eating better after this crazy project ends” or “I’ll spend quality time with family once this deadline passes” - legitimate reasons to deprioritize personal growth and connection. These weren’t lies; work really does make it harder to maintain perfect health habits or nurture relationships. The excuses were completely valid, which made them perfect shields against the dragons.

Free urgency and structure: Deadlines, projects, crises that gave your days automatic momentum and meaning without you having to generate it from within. The Entropy Dragon couldn’t take hold because external forces constantly demanded order and progress. Scarcity felt manageable because the next paycheck was always coming.

Free metrics of productivity: Meetings attended, code shipped, presentations delivered - constant external validation that you were “productive.” The Squander Dragon couldn’t accuse you of wasting time when you had calendar screenshots and performance reviews proving otherwise. Even if the work was ultimately meaningless, it felt productive, and that feeling was enough to keep the dragon quiet.

The gap year opens the box. Suddenly there’s no meeting schedule to explain away poor health habits, no work exhaustion to buffer loneliness, no legitimate crisis to postpone difficult conversations with family. You need to create your own social connections, generate your own sense of urgency and purpose, and face your habits without the comfortable excuse of being legitimately exhausted.

The dragons are the same size they’ve always been. The difference is now you’re face-to-face with them in an empty room, and the uncomfortable truth emerges: some of your struggles weren’t actually about time or energy - they were about something deeper that work was helping you avoid.

The Dragon Spawn: How Each Ancient Manifests

Each ancient dragon breeds specific offspring that attack in different ways. Understanding these manifestations helps you recognize which dragon is currently testing you.

Scarcity’s Spawn

The Market Volatility Dragon: Every red day feels personal when you’re drawing down. This spawn makes you check your portfolio obsessively, turning market noise into existential threat.

The Employability Dragon: “You’ll never get hired again at this level.” Whispers that the job market has moved on, that your skills are stale, that younger people will work for less.

The Expense Surprise Dragon: “What if the roof needs $50K in repairs?” Manufactures anxiety about every possible financial catastrophe that could derail your plan.

The Lifestyle Creep Dragon: “Can you really live on 60% of what you used to?” Questions every purchase, makes you second-guess if you can truly adjust to a different financial reality.

Entropy’s Spawn

Parkinson’s Dragon: Named for Parkinson’s Law. Tasks expand to fill infinite time. This spawn is particularly vicious because it makes you complicit in your own time theft. What should be a productive day becomes a haze of half-completed tasks.

The Addiction Dragon: For me, this isn’t about alcohol (I gave that up for better sleep) - it’s social media. The endless scroll, the dopamine hits from notifications, the fear of missing out. During a gap year, without the structure of work, these digital sirens could easily consume entire days.

The Decay Dragon: A day missed at the gym turns into a week, turns into a month. Physical decline accelerates mental decline. At 50, you still have peak physical capability, but this window closes fast - and this dragon knows it.

The Drift Dragon: Boredom → Vegetating → Messing up sleep schedule → General lack of purpose. This spawn creates aimless days that become aimless weeks, leaving you wondering where the time went.

Squander’s Spawn

The Comparison Dragon: “Everyone’s achieving while you’re… what exactly?” Opens LinkedIn to show you former colleagues’ promotions. Makes you question if you’re falling behind while everyone else races ahead.

The Legacy Dragon: “What are you building that will last?” Questions whether your gap year creates anything meaningful or if it’s just expensive self-indulgence.

The Productivity Dragon: “Another day with nothing to show for it.” Without external metrics, how do you measure a successful day? This spawn makes every relaxed moment feel like theft from your future.

The FOMO Dragon: “You’re missing out on the best opportunities.” While you’re on gap year, others are getting promoted, building companies, making connections. You’re choosing to be absent during your peak earning and impact years.

Taming the Dragons: From Fear to Power

These dragons cannot be slain - they’re fundamental forces like gravity or time. But they can be tamed, managed, even transformed into allies. The goal isn’t to defeat them but to understand their nature and build structures that channel their energy productively.

The Scarcity Dragon Dialogs

Dragon: “What if the stock market tanks while you’re on your gap year?”

Me: “That would make me very uncomfortable to take money out of my stocks.”

Dragon: “See? You can’t afford this. One bad year and you’re done.”

Me: “Yes, and… the stock market will likely recover in the long term. I’ve built a 2× expense buffer specifically so I don’t have to sell in a down market.”

Dragon: “What if you can’t get a job after the gap year?”

Me: “Job market is MUCH worse than it was 4 years ago. Lots of experienced folks in the market. If applying to a job I’m overqualified for - they’ll be like you’ll leave as soon as you can. Ugh. Even though I have a network, doesn’t matter if companies not hiring.”

Dragon: “Exactly. You’ll be unemployable. Another year older, skills getting stale…”

Me: “Yes, and…”

  • I’ve got 25 years+ of experience at top tech companies on a ton of various projects
  • I’ll be heavily invested in professional development, so that makes me much more valuable
  • I’ll be doing content production, so people can see my skills
  • The gap year makes me MORE valuable, not less - I’ll have mastery others don’t

Dragon: “What if you end up with a lower income when you return? Meta pays at 90th+ percentile.”

Me: “This is very probable.”

Dragon: “So you’re throwing away peak earning years for… what?”

Me: “Yes, and…”

  • Meta lets you have a “short interview loop” if you boomerang in a year
  • I’ve always said if you won’t take a job for a pay cut, you shouldn’t take it
  • I guess that could be either the job is more fun, or cuz it’s the highest paid job you can get :)
  • Some things are worth more than maximizing income

Dragon: “What if you’re wrong about your expenses?”

Me: “It’s critical you get this right.”

Dragon: “One surprise medical bill, one major house repair, and your whole plan collapses.”

Me: “Yes, and…”

  • I’ve been tracking expenses for years in Monarch Money and Boldin retirement planning software and have good baseline data
  • I’m not forgetting the non-obvious things like health insurance ($40K/year - wow!) and taxes (even though drawing long term cap gains, it adds up, especially with WA 7% tax over $270K) and major house repairs
  • I can adjust spending during the gap year if needed (not locked into fixed costs)
  • I am conservative with estimates and build buffer for surprises

Taming Scarcity: Building True Security

The Scarcity Dragon will never fully trust that you have enough - that’s its nature. But you can build a relationship with it based on transparency and regular communication.

How do you know it’s time to execute the gap year through the scarcity lens

You should understand all the dragons in detail, but from the financial security dragon (again the other dragons might be equally if not more dangerous), but I’ll answer you anyways:

  • Money: Net worth exceeds “X” Million.
    • Beyond this the risk is negligible
  • Date: XX/YY if net worth is higher than “Y” million, where Y is much lower than X.
    • If you wait till after XX/YY, the value is negligible.

What are the actual dates and numbers?

  • A magician never reveals his tricks, and Igor’s gotta have some secrets.

Come on, can you at least give a formula?

I think the most conservative:

  • Baseline: Hold 2× annual expenses in cash-like accounts
  • Assumptions:
    • You can find a job in ≤ 12 months (possibly at lower comp)
    • Expense estimates includes taxes, insurance, repairs, college as required, and an emergency
    • You’re not forgetting hidden costs like $40K/year health insurance
    • Expense estimates include taxes, insurance, repairs, college, and emergencies
    • You’ve tracked expenses for years in Monarch Money and Boldin

The dragon’s wisdom (when tamed): From the Prophet: “What is fear of need but need itself? Is not dread of thirst when your well is full, the thirst that is unquenchable?”

And from my Bestie: “If you’re not gonna feel safe at 2 years × your expenses, it’s hard to imagine you’ll feel safe at 3 years × your expenses.”

When properly tamed, the Scarcity Dragon becomes your teacher in efficiency, showing you what actually matters versus what was just lifestyle inflation.

See my full money philosophy, retirement planning, and stock concentration for context on these financial triggers.

The Entropy Dragon Dialogs

Dragon: “What if you get lazy and lose all direction and discipline?”

Me: “Without work structure, it’s easy for me to drift without momentum AND lose discipline around health habits. At 50, I still have peak physical capability, but this window closes fast - health decline could undermine everything the gap year is supposed to accomplish.”

Dragon: “Exactly. You’ll sleep until noon, skip workouts, eat garbage. Within months you’ll be a shadow of yourself.”

Me: “Yes, and…”

  • I know my mental health practices and can recognize the warning signs early
  • Removing work stress eliminates a major barrier to consistent health habits
  • I can build structure into the gap year — it doesn’t have to be completely unstructured
  • Having control over my schedule means I can exercise at optimal times, get proper sleep, and meal plan
  • Physical health is the foundation for mental clarity, project energy, and relationship engagement

So: Create a “gap year structure” with daily routines, weekly goals, and regular accountability check-ins. Build in “safety clips” - personal trainer sessions, gym membership, kettlebell classes. Make health routines the cornerstone of gap year structure.

Dragon: “What if you get bored and start vegetating?”

Me: “I can get bored easily, which leads to vegetating - mindless scrolling, avoiding meaningful work. Vegetating leads to messing up my sleep schedule and general lack of purpose. A day missed at the gym turns into a week, turns into a month.”

Dragon: “You’ll waste the entire year on Netflix and social media. Nothing to show for it.”

Me: “Yes, and…”

  • AI evolves so rapidly there’s something genuinely new every 2 weeks — built-in novelty to prevent boredom
  • Using AI lets me focus on my mastery areas — less time on tedious tasks, more on what I’m uniquely good at
  • AI gives me huge leverage on bespoke software projects like my Kettlebells and Mortality software

So: AI provides both intellectual stimulation and productive outlets for creativity.

Dragon: “What if you get lonely without daily work social interaction?”

Me: “Loneliness could be a major factor - work provides daily social interaction.”

Dragon: “You’ll become isolated, disconnected. Your social skills will atrophy. Depression will follow.”

Me: “Yes, and…”

  • I know retired/gap year folks who are available during the day
  • These people are fascinating - they’ve chosen unconventional paths, unencumbered by society’s expectations
  • They have time to think deeply and even experiment with weird ideas (one person wanted to try turning cameras off every 7 minutes during conversations to see how it changes the dynamic - weird but interesting!)
  • I have friends and flexibility to hang out more regularly
  • I can have deep conversations with Tony, my AI life coach (tony_tesla project)
  • There are lots of people on the internet to meet — I’ve already started and it’s pretty cool
  • Many people would like mentorship, and I’ve got the time and experience to help them

So: Schedule regular time with retired friends and deepen existing relationships.

Dragon: “What if you get depressed and spiral into a dark place?”

Me: “Boredom → Vegetating → Skipping exercise → Depression is a well-established pattern for me.”

Dragon: “You know this pattern. You know how it ends. Why risk it?”

Me: “Yes, and…”

  • I have mental health support systems (therapy, medication, practices) that would continue
  • Without work stress, I can focus on mental health proactively rather than reactively
  • The gap year is about building health, not destroying it

So: Keep existing mental health infrastructure in place throughout the gap year.

The Family Paradox Dialog: When Dragons Attack What You Love Most

A key motivation behind my gap year is the desire to spend more meaningful time with my family. Time together is precious and fleeting; once gone, it cannot be reclaimed. However, the Entropy Dragon knows this and attacks precisely here.

Dragon: “What if you get resentful that your family won’t spend time with you?”

Me: “I’ll have lots of free time but family will still be busy with their schedules. Could lead to resentment when they can’t match my availability.”

Dragon: “You’re sacrificing everything for people who won’t even notice. They have their own lives. You’ll be sitting at home alone while they’re out with friends.”

Me: “There are two things that really worry me here…”

The dragon exploits two specific fears:

Seeing them in their natural state: When I’m working, I only see my family in short bursts - mornings, evenings, weekends. But during a gap year, I’ll be around all the time to observe their natural rhythms. Parkinson’s law is very real: for kids and folks who aren’t working, many things take longer than they could. What’s worse is when I’m judging myself for being inefficient during my gap year, seeing the same patterns in my family bothers me even more. It’s a mirror I don’t always want to look into.

The time investment mismatch: There’s an inherent asymmetry here: I’m giving up my career momentum to spend more time with family, but they can’t reciprocate that availability. Even though my gap year might give me an additional 50 hours per week, my family doesn’t have any more availability. Practically speaking, I may only gain 5–10 extra hours with them each week.

Dragon: “So you’ll resent them for not appreciating your sacrifice. The gap year will damage the very relationships you’re trying to strengthen.”

Me: “The real challenge isn’t the quantity of time but learning to appreciate the quality of whatever time we do have together.”

Me: “Yes, and…”

  • Relationships deepen like lifting weights — start light and gradually get heavier
  • I’ll have the flexibility to work around their schedules instead of forcing mine
  • Without work stress, I’ll have inner peace that lets me be more compassionate and patient
  • Time isn’t scarce anymore, so I have much more flexibility to accommodate their schedules
  • An abundance mindset with time means I’m not competing family time against “very limited” personal projects
  • Deepening family relationships is a huge part of what makes this gap year worthwhile

So: Schedule regular family dates and focus on quality over quantity, letting relationships develop naturally at their pace.

Taming Entropy: Structured Freedom

The Entropy Dragon requires constant energy input to keep at bay. This isn’t a bug - it’s thermodynamics. The key is building minimum viable structure that generates order without recreating the prison of work.

At 50, you have peak capital (time, energy, resources) to invest in your body, mind and relationship infrastructure. Every dollar spent on prevention now saves $10 in treatment later. Habits are the “dividend-paying stocks” of personal development - they keep generating returns without additional input.

Where Igor Finds the Strength: Igor will summon his best self, the 5am Igor who Begins with end in Mind, and sets future Igor to run on automatic. So here are some guard rails and spells to guide me and others on my journey.

Anti-Entropy Infrastructure:

Physical Health Anchors:

  • Daily kettlebell practice (non-negotiable morning ritual)
  • Weekly trainer sessions (external accountability)
  • Sleep schedule protection (10pm-6am sacred time)
  • See my kettlebell practice and broader physical health philosophy

Mental Health Practices:

Relationship Rhythms:

  • Weekly date night (scheduled like it matters)
  • Monthly 1:1 with each kid
  • Quarterly friend retreats
  • This connects to my broader thinking on relationship health

Addiction Prevention Metrics: For me, addiction isn’t about alcohol (I gave that up for better sleep) - it’s social media. The endless scroll, the dopamine hits from notifications, the fear of missing out. During a gap year, without the structure of work, these digital sirens could easily consume entire days.

  • Max 30 minutes/day on social apps
  • Phone set to grayscale; app timers enforced
  • One “no-screen” block after 8pm daily
  • Weekly screen-time audit and reset

Loneliness Prevention Metrics:

  • Deepened existing friendships - Regular scheduled time with retired/gap year friends
  • New connections with unique people - Meeting others who chose unconventional paths and think deeply
  • AI companionship - Deep conversations with Tony (AI life coach) and evolving AI tools
  • STRETCH: Appreciating solitude - Finding peace in being alone without feeling lonely
  • STRETCH: Mentorship at scale - Helping others with my time and experience
  • STRETCH: Online community building - Meeting interesting people on the internet

Measurable targets:

  • Two recurring daytime social blocks per week
  • One new person/group per month
  • One quarterly daylong/retreat with a friend

Family Investment Metrics:

  • Nothing is more valuable than family – the time together holds the greatest meaning
  • Fully engaged and present (free from work distractions and stress)
  • Available for spontaneous moments (no conflicts blocking connection)
  • Natural conversation happens regularly
  • Passive hangouts (e.g., coffee shop together doing our own thing)
  • Consistent date night approach
  • Acceptance with gentle influence where appropriate
  • Gracefully step back when peers join; facilitate logistics (driving, hosting)
  • Embrace the bittersweet nature of their growth
  • STRETCH: Multi-month project we do together

Measurable targets:

  • Monthly 1:1 with each kid; weekly spontaneous-time log
  • Weekly date night; monthly day date
  • One shared project per quarter

Successful parenting ultimately means my children know, deep down, that I’m always there for them — quietly in the background, offering steady support without pressure, ready whenever they need me.

You can probably look at my 2025 goals, which sadly look a lot like my 2024 goals, and will probably look like my 2028 goals if that’s when I actually get my gap year.

The AI Advantage Against Entropy:

  • AI evolves so rapidly there’s something genuinely new every 2 weeks — built-in novelty prevents boredom
  • Using AI for leverage on projects — you can build things that would have taken months
  • AI conversations with Tony (my life coach) provide intellectual stimulation

When tamed, the Entropy Dragon becomes your personal trainer, forcing you to actively maintain and grow rather than passively exist. It teaches you that freedom without structure is just another prison.

The Squander Dragon Dialog

Dragon: “Look at you - sleeping in, going to the gym, reading books. Is this what success looks like? Are you really setting a good example for your kids?”

Me: “One lens is that I’m being lazy and self-indulgent…”

Dragon: “Exactly. They’ll see you as someone who quit when things got hard. A cautionary tale about giving up.”

Me: “Yes, and… there’s another lens: I’m role-modeling that life isn’t just about grinding until you die. I’m showing them how to invest in health before crisis, relationships before regret, and mastery for its own sake.”

Dragon: “But what will you have to show for it? No promotions, no launches, no metrics…”

Me: “I’ll have a stronger body at 50 than most have at 40. I’ll have been present for my kids’ last years at home. I’ll have achieved mastery in domains I choose, not ones assigned to me. That’s not squandering - that’s investing.”

Taming Squander: Making Every Day Count

The Squander Dragon loses its power when you realize that “productivity” isn’t about external metrics - it’s about intentional investment in what matters. You’re not wasting time; you’re investing it in health, relationships, and mastery that compound over decades.

The Anti-Squander Reframe: Instead of thinking about it as a gap year (which sounds like absence), think about it as pursuing a “PhD in Life Optimization” - intensive research into health, relationships, and chosen mastery.

This aligns with my approach to continuous learning and overcoming resistance to change.

The key is creating tangible artifacts that prove the year was invested, not wasted. These artifacts serve as both daily accountability and lasting proof of productivity - just productivity YOU define, not what others measure.

Artifacts as Evidence of Investment:

AI Mastery Artifacts:

  • 12 PRDs, 6 shipped micro-apps
  • 12 technical posts, 4 talks/videos
  • Working notes repo for experiments/implementations
  • Each artifact proves deep learning and capability building

Content Creation Artifacts: Maybe no one will read/watch it but me and my Mom, but good enough for me.

  • Blog artifacts: Regular posts documenting the journey
  • Video artifacts: YouTube channel, Reels showing progress
  • These create a permanent record of growth and learning

Revenue Experiment Artifacts: Monthly recurring revenue would be minuscule vs. a tech salary, but that’s not the point.

  • Product: 1 paid template; 1 cohort workshop pilot
  • Revenue: Affiliate links; ad revenue experiments (goal: $100/month after 6 months)
  • These prove ability to create value independently of employment

New Sources of Meaning:

  • Being fully present for your family (they don’t care about your title)
  • Mentoring others with your 25+ years of experience
  • Building things because they’re interesting, not because they’re assigned
  • Going deep on problems without arbitrary deadlines

Anti-Squander Metrics:

  • Weekly artifact creation (tangible evidence of investment)
  • Monthly mentorship sessions (value created for others)
  • Quarterly learning milestones (measurable growth)
  • Daily intentional choices aligned with stated values

When tamed, the Squander Dragon becomes your guide to intentional living, teaching you that true productivity means investing time in what matters most.

Dragon Transformation: When Fear Becomes Fuel

The ultimate goal isn’t to eliminate these dragons but to transform them from adversaries into allies. Each dragon, when properly understood and tamed, offers unique gifts:

Scarcity → Resourcefulness: The dragon that made you fear every expense becomes your teacher in distinguishing needs from wants. It shows you that security isn’t about having millions but about knowing what “enough” really means.

Entropy → Evolution: The dragon that threatened decay becomes your catalyst for growth. Without external pressure, you must generate your own momentum - and this self-directed energy is far more powerful than any external deadline.

Squander → Stewardship: The dragon that accused you of wasting a precious opportunity becomes your guide to intentional living. You learn that productivity isn’t measured by external metrics but by alignment with your values. Every day becomes an investment in the life you actually want, not the life others expect.

The Dragon Keeper’s Daily Practice

Living with dragons requires daily attention. They’re not pets, but they’re not enemies either - they’re forces that must be acknowledged and managed through consistent practice. I have a long list

  • Entropy Check:

    • Get up before 5am
      • Anchor my day before I’m overrun by noise
      • Make a priority list
    • Physical/Emotional/Joy habits/practice
      • I have a log list, and need to create my own tracker, which needs to evolve to become humane

  • Squander Check:

    • Ensure I’m operating off my priority list
    • Creation block (writing/coding) - prove you’re investing wisely
    • What can I do to maximize my family time

Weekly Dragon Council:

  • Quick expense tracking (Fridays only) - stay aware without obsessing
  • Which dragon was loudest this week?
  • What triggered each dragon?
  • Which taming strategies worked?
  • What needs adjustment?

The Dragon Council: Monthly and Quarterly Reviews

Regular formal reviews keep you from being slowly overwhelmed by any one dragon. These aren’t performance reviews - they’re relationship check-ins with fundamental forces.

Monthly Dragon Council:

Scarcity Assessment:

  • Cash burn rate vs. projection?
  • Market anxiety level (1-10)?
  • Any surprise expenses?
  • Still on track for 2× expenses buffer?

Entropy Assessment:

  • Health/Habits adherence (exercise, sleep, nutrition)?
  • Project momentum maintained?
  • Relationships deepening or drifting?
  • Energy level trajectory?

Squander Assessment:

  • Artifacts created this month?
  • Intentional investments made (health/relationships/mastery)?
  • Alignment with stated values?
  • Feeling of meaningful progress (1-10)?

Quarterly Dragon Summit:

Strategic Questions:

  • Which dragon is currently strongest?
  • Which dragon have I successfully tamed?
  • Which dragon needs more attention next quarter?
  • Are any dragons starting to transform into allies?

Trip-Wire Assessment:

  • Health adherence < 50% for 2 consecutive months? (Entropy winning)
  • Cash buffer < 1.25× annual expenses? (Scarcity winning)
  • No artifacts shipped for 6 weeks? (Squander winning)
  • Family stress rising consistently? (All dragons winning)

If any trip-wire is hit, begin mitigation immediately. If it persists after one month, consider early exit protocol.

Pre-Battle Preparation: Knowing Your Dragons

Before you open the box and release the dragons, map out your specific vulnerabilities and strengths. This isn’t pessimism - it’s reconnaissance.

Personal Dragon Assessment:

My Scarcity Dragon is triggered by:

  • Market drops over 5%
  • Unexpected expenses over $5K
  • Reading about tech layoffs
  • Comparing net worth to others

My Entropy Dragon is triggered by:

  • Unstructured mornings
  • More than 2 days without exercise
  • Social isolation for 48+ hours
  • Lack of concrete deadlines

My Squander Dragon is triggered by:

  • Days without tangible output
  • Seeing others’ achievements on LinkedIn
  • Relaxing “too much”
  • Not having a “productive” day by traditional metrics

Pre-Mortem: How Each Dragon Could Win

Top failure modes and mitigations (mapped to the dragons above):

If Scarcity wins: I return to work prematurely out of financial fear, having learned nothing except that I’m controlled by money anxiety.

  • Mitigation: Pre-fund 2× annual expenses; monthly runway update; rules in “Taming Scarcity”

If Entropy wins: I drift into poor health, damaged relationships, and wasted time, proving that I need external structure to function.

  • Specific failure modes:
    • Drift/vegetating → Mitigation: Daily plan + weekly review; external structure (trainer/classes)
    • Isolation/loneliness → Mitigation: Pre-scheduled social slots; join clubs/classes; mentorship calendar
    • Scope creep on projects → Mitigation: WIP limit (max two active projects); define “done” for each artifact

If Squander wins: I look back after a year realizing I wasted the opportunity - no health improvements, no deeper relationships, no mastery achieved. Just expensive procrastination.

  • Mitigation: Weekly artifact creation; monthly investment audits; clear success metrics

The Voices in My Head: The dragons speak through internal voices - doubts, fears, and whispers that undermine confidence. Recognizing these as dragon-speak rather than truth is the first step to taming them.

Dragon-Taming Resources:

Allies in the fight:

  • Other gap-year/retired folks who’ve faced these dragons
  • Professional support (therapy, financial advisor, trainer)
  • Family members who benefit from your presence
  • AI tools that provide leverage and learning

Can 1 become 2? The Extend-to-Year-2 Test

At month 10, if you are so inclined, assess whether you’ve tamed the dragons sufficiently to extend the gap year. This isn’t about slaying them - they’ll always be there. It’s about whether you’ve built sustainable systems to live with them.

Extend to Year 2 if ALL are true:

Entropy Tamed:

  • Health adherence ≥ 80% (sleep, workouts, nutrition maintained)
  • Energy levels stable or improving
  • Relationships deepened not degraded

Squander Tamed:

  • 6+ meaningful artifacts shipped
  • Clear progress on health/relationship investments
  • Tangible evidence of growth in chosen domains

Scarcity Tamed:

  • Still hold ≥ 2× annual expenses in cash-like accounts
  • 5% portfolio return can replenish next year’s draw
  • No financial panic despite market volatility

Otherwise, use Year 2 as pre-funded job-search runway: plan in months 10-11, begin search at month 12.

The Dragons’ Final Wisdom:

The challenge of the gap year isn’t about defeating these dragons - they’re immortal forces that exist in everyone’s life. Work just hides them. The challenge is about learning to live with them consciously, transforming them from hidden fears into acknowledged teachers.

Master this, and you don’t just take a successful gap year - you learn to live with the fundamental forces that shape every human life. That’s the real treasure the dragons guard.

Appendix: How Work Boxed the Dragon Deep Dive.

I think this deserves more thinking, after all the better we can understand this the better.

Work boxing Scarcity

An easy observation: Work results in you getting a steady pay check, implies you don’t have to wrory about money so long as you’re not worried about being fired, or exceptional drops in the stock market, or growth in your expenses.

A harder observation: You are only thinking about scarcity in terms of money, not time! Of course, time is constant, so the scarcity of time available to non-work!

Critical Insight: Work slays the “Money Scarcity” dragon, but creates the “Non-Work Time Scarcity” Dragon

Work boxing Squander

Critical observation: “Gap year is an opportunity that can be squandered”, implies you can’t squander the time working, something is wrong with that logic, but we get back to that later.

The smaller version of squander, the idea that you can’t squander your work time when you’re working. How come?

  • Management!
  • Managmeent Chain!
  • Peers!
    • NOTE: OK this is much bigger then I imagined.
  • Performance Reviews!
  • Clear Expectations!
  • Accountabilities
  • Ceremonies!
  • Someone asking you OK what have you accomplished.

Work boxing entropy

HUGE Paradox. When we are working, our disposable time becomes scarce/precious, increasing its value, making us scrutinize how we spend it (when we have sufficient will power), which results in very high quality time allocation, often far better then if we’re on a gap year when we have more time. (Reframe - paradox of plenty) - Scarcity clarifies value. - Parkinson’s law

  • Entropy is stopped by various forces:
    • Explicit: I wake up every day at 5am because that’s my habit
    • Implicit: I wake up every day at 5am because I need to get to work at 6am.
    • Hybrid: I wake up every day at 5am so I’ll be ready to do something in the future.

By virtue of accomplishing things, having impact, providing value, you actively fight entroy.