A year and a half ago, my wife and I crossed a massive financial threshold. She officially retired, and because my part-time income only covers about a third of our living expenses, we finally entered the “decumulation” phase.

For the first time in our lives, we started actively drawing down our assets to pay for our daily lives. Fortunately, thanks to the compounding power of our portfolio, our net worth could still continue to grow, but the psychological shift of selling off equities is very real.

I recently recorded a solo episode of the Earn and Invest podcast to reflect on this exact transition. Here are the ten biggest things I have learned after eighteen months of spending down our retirement money.

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1. The fear wears off. Transitioning from a lifetime of strictly accumulating wealth to actually liquidating it can produce an incredible amount of anxiety. I was definitely nervous at first. However, I found that once I started executing our quarterly liquidations to cover expenses, the fear vanished. The process simply became our new normal.

2. Decumulation is lumpy. Real world spending is naturally uneven. You will have unexpected emergencies (like a sudden $4,000 car air conditioner repair) or spontaneous purchasing decisions. Trying to strictly white-knuckle a rigid monthly budget will only cause unnecessary anxiety. It is far better to accept that some months will be expensive and others will be quiet. It all evens out over the year.

3. You have to get used to the unknown. Life is full of unpredictable costs and opportunities. Recently, we made a sudden decision to purchase first-class flights abroad for an international conference. If you fear the unknown, you run the risk of becoming miserly and saying no to unique experiences that won’t actually bankrupt you.

4. Anxiety is just a YouTube video away. Having ample free time in retirement can tempt you to obsessively over-optimize your finances. It is easy to fall down internet rabbit holes researching endless Roth conversions, tax hacks, and asset protection. Deciding to accept a plan that is “good enough” rather than perfect is a conscious, healthy decision to protect your peace of mind.

5. We are spending less than we thought. Despite being high spenders who do not restrict ourselves on luxuries like new cars or premium travel, we are naturally spending less than our conservative retirement models predicted. We spend to optimize our happiness rather than spending just to hit an arbitrary target.

6. Spending more hasn’t made us happier. Consistent with the decreasing marginal utility of wealth, spending beyond a certain baseline does not provide an incremental boost to our overall happiness. Our most joyful quarters have proven to be entirely unrelated to how much money we actually spent.

7. You think less about money. In the accumulation phase, a lot of emotional energy is spent obsessing over spreadsheets and net worth tracking. Once you retire and put a solid plan on autopilot, the fear of “not getting there” completely disappears. This frees up your mind to focus on the things that actually matter.

8. The dips are not scary. Despite recent market volatility, I have found myself far less anxious about market dips than I anticipated. To maintain my peace of mind, my strategy during market downturns is to simply avoid checking our net worth and focus on living life instead.

9. Optimization loses its appeal. The thrill of optimizing every tax loophole and finding extra yield fades once you have already won the financial game. When you have enough wealth to last the rest of your life, squeezing out an extra dollar loses its utility. It simply is not worth the effort anymore.

10. Taxes are still a massive pain. The one major downside of this phase is the ongoing burden of complex tax planning. Without an employer to seamlessly withhold taxes, managing quarterly estimated payments, capital gains on liquidations, and complicated tax filings remains a persistent headache.

If you are approaching retirement or are already in the thick of it, I highly recommend checking out the full podcast episode where I dive much deeper into all of these insights.

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Community Update: A Special Coaching Offer

Before I sign off, I want to share a unique opportunity. As many of you know, my next book, The Happiness Code, is slated for release in March 2027.

To help drive early momentum and pre-orders, I am offering a very special promotion. I normally charge $2,000 for a package of five one-hour Zoom sessions where we dive deep into purpose, career, and “enoughness” coaching.

Right now, if you purchase 50 paperback copies of The Happiness Code on Amazon (which totals roughly $1,000) and email me the receipt, I will give you the entire five-session coaching package for free.

It is a great way to get the coaching at half price while receiving 50 books to share with your friends, family, or colleagues.

Let me know in the comments: what is your biggest fear about the decumulation phase?

I am about to take a highly unpopular stance.

If you spend any time in the financial independence community, you know the stories of those who successfully pulled themselves up by their bootstraps. We all know someone whose parents had terrible financial habits, gave them zero guidance, and yet, they figured it out, taught themselves to invest, and became financially independent.

When we see these success stories, no one ever credits the parents. We understand that it was the child who took personal responsibility. It was internally driven. The child chose to be extraordinary.

So why do we flip this logic completely upside down when we talk about wealthy families?

The “Shirtsleeves to Shirtsleeves” Myth

There is a pervasive belief that wealth is automatically squandered by the third generation—the whole “shirtsleeves to shirtsleeves” phenomenon. The argument goes like this: wealthy parents give their children too much, which makes them lazy, and eventually, the grandchildren blow whatever is left.

We immediately blame the parents. We say the parents failed to model the correct behavior or spoiled the kids.

But if we don’t give poor parents credit for a child’s success, why do we automatically blame wealthy parents for a child’s failure? Whether a child becomes financially independent or squanders a fortune, I believe the driving force is exactly the same: the child’s own personal responsibility.

The Flaw in “The Millionaire Next Door”

This brings me to Thomas J. Stanley and William D. Danko’s classic book, The Millionaire Next Door.

In the book, they coin the term “Economic Outpatient Care” (EOC) to describe the financial gifts wealthy parents give to their adult children. The authors show data suggesting that children who receive EOC tend to be under-accumulators of wealth (UAWs). Their conclusion? Giving your children money causes stunted independence and financial failure.

I think all of this sounds perfectly logical, but there is a massive problem with the data: it only shows correlation, not causation.

Stanley and Danko never proved that giving a child money caused them to fail. They just noticed that adult children who received money from their parents generally weren’t wealthy on their own.

I want to propose the exact opposite causation. What if the child isn’t failing because they received money? What if they are receiving money because they were always going to fail?

Being a millionaire and achieving financial independence requires extraordinary discipline. Very few people actually accomplish it. Why should we expect the children of the wealthy to automatically be just as extraordinary as their parents?

If an extraordinary, wealthy parent has an ordinary child who does not have the personal drive to build a massive net worth, what happens? The child struggles, and the wealthy parent naturally steps in to provide Economic Outpatient Care. The money didn’t make the child ordinary; the child’s ordinary nature necessitated the money.

Why I Believe in Giving Freely

I am not presenting this as scientific fact, but as my own personal belief: I think we are tiptoeing around the next generation too much.

We are so terrified of ruining our kids that we withhold our wealth and hide our financial reality from them. I think we have it all wrong. We need to model the behavior that helps them understand exactly what is going on with our finances.

More importantly, I think that when we have enough money, we should gift it to our kids.

We should give them every chance to get into the stock market. We should support them so they have a safe buffer to build the skills they need. What is the point of working so hard to become wealthy if we refuse to make sure our children are also financially secure?

It is still their individual responsibility to decide what they want to do with that foundation. Will they build an extraordinary life and career with it, or will they squander it? That is ultimately up to them.

But I am not going to withhold my support just because a book interpreted correlation for causation.

A Safety Net, Not a Snare

By the way, if you need further proof that The Millionaire Next Door is oversimplifying, just look at how money behaves outside of wealthy bubbles. When sociologists study these exact same financial transfers in low-income and working-class families, they find the complete opposite result: parental financial support doesn't stunt a child's independence, it actually creates it. In those households, a financial safety net is exactly what keeps kids from dropping out of college and helps them safely transition into stable careers.

If the simple act of handing a child money was the root cause of laziness and financial failure, it would destroy working-class kids, too. Instead, it gives them a fighting chance. Let's stop treating our own generosity like a disease, and start trusting our kids to build their own extraordinary lives with the foundation we have worked so hard to give them.

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There is a sharp divide in the personal finance world right now. While many of us in the financial independence space are obsessing over how to maximize our portfolios and “die with zero,” a massive segment of the country is simply trying to survive. They are living paycheck to paycheck, praying a basic emergency does not wipe them out.

This week on the Earn and Invest podcast, I sat down with bestselling author Anthony O’Neal to discuss this disconnect and his book, Stop Living Paycheck to Paycheck.

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Anthony strongly critiques the traditional path most of us were handed by our parents. You know the one. Take on massive student loans, work for forty years while maxing out a retirement account, buy a house, and retire at 65 just to enjoy a few years before passing away.

Anthony calls this a “whack” dream.

His own financial awakening happened on a summer night in 2004. He was hanging out with friends who were all driving heavily financed luxury cars like Range Rovers and S-Class Mercedes. But when one of those friends had to ask to borrow five dollars just to eat at McDonald’s, it hit him. They looked incredibly successful on the outside, but they had absolutely no freedom.

If you want to break that cycle and build real wealth, Anthony shared a few core principles we all need to revisit.

Stability Before Strategy

Anthony shared a brilliant parable about an ER doctor. When a critical patient arrives in the emergency room, doctors do not immediately try to fix them based on a guess. A wrong guess could be fatal. The first job is simply to get the patient stable. The same applies to your wallet. You have to stabilize your life before you can build wealth. This means writing down a clear vision, saving a one-month emergency fund, and setting up a basic estate plan.

Margin Matters More Than Income

Did you know that nearly half of six-figure earners still live paycheck to paycheck? Wealth is not built by the size of your salary. It is built by your margin. If you actively manage your spending to ensure less goes out than comes in, you create the surplus necessary for long-term investing.

The Power of Generosity

Anthony is a firm believer in giving away the first ten percent of his income, noting that generosity often returns to you in unexpected ways. I completely second this. In my career as a hospice doctor, I have consistently observed that generous individuals tend to have much more peaceful, happy, and appreciative deaths.

Passing the Torch

To build multi-generational wealth, Anthony recommends holding annual “family legacy meetings.” One of his mentors even takes his extended family to a cabin once a year (with NDAs signed by spouses) to discuss family struggles, long-term wealth goals, and the eventual transition of assets. A good inheritance is not just about money; it is about passing down financial literacy.

If you are already financially independent, you might think an episode about living paycheck to paycheck does not apply to you. But I urge you to listen anyway. You likely have children, siblings, or parents who desperately need these core principles. Plus, revisiting the basics is an excellent way to audit your own financial plan and ensure your strategies have not gotten too loose.

What is one foundational financial rule you wish someone had taught you when you were eighteen?

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I recently had a fascinating conversation on the podcast with personal development trainer Michelle Masters. We talked about the deep, often hidden psychological forces that drive how we handle our finances. That discussion struck such a chord with me that I decided to record a solo “10 Things” episode to unpack the emotional and psychological underpinnings of behavioral finance.

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What I have learned over the years is that our financial outcomes have very little to do with math. They have everything to do with how our brains process fear, safety, and self-worth.

Here is a sneak peek at the ten core insights I break down in the new episode.

1. Behavioral finance is about the mind, not the spreadsheet. We often convince ourselves that building wealth requires complex calculus. The truth is that the numbers are actually quite simple. The real hurdle is the human mind, which constantly pushes us to make emotional mistakes like buying high and selling low.

2 & 3. Our money behaviors are intimately tied to trauma. Bad financial decisions rarely stem from a lack of intelligence. They are usually coping mechanisms built around childhood wounds. That trauma generally comes in two flavors: lived and generational. I experienced lived trauma when my father died. I was seven years old, and I watched my mother constantly worry about money after his passing. Even though I am now wealthy and financially independent, that experience left me with enduring anxiety around spending.

Generational trauma, on the other hand, is passed down through modeling or even epigenetics. My grandmother was an orphan during the Great Depression who hoarded food and money. She passed those scarcity behaviors down to my mother, who then modeled them for me.

4 & 5. Your mind will drive you to extremes. A spreadsheet will not lie to you, but your brain certainly will. A negative mindset can shut down wealth accumulation before it even begins. Take children of divorce who saw their parents use money as a weapon of manipulation. They often grow up believing money is inherently evil and compulsively spend it as soon as it hits their bank accounts.

On the flip side, an anxious mind can trap financially independent people in an ultra-conservative scarcity mindset. They obsess over lowering their safe withdrawal rates and agonize over losing Social Security. This completely prevents them from using their wealth to live joyful, well-adjusted lives.

6. Getting good with money often requires therapy. Because childhood coping mechanisms are deeply ingrained in our subconscious, they are incredibly difficult to fix on our own. Think of your mind like a building. Sending experts to the penthouse to fix an electrical problem that is actually located in the basement will never work. To resolve subconscious money blocks, you have to go down to the basement through professional therapy.

7 & 8. The double-edged sword of financial advisors. If you are unable or unwilling to work through your trauma, handing your portfolio to a competent advisor can act as a great stopgap. A good professional will keep you from making impulsive moves during a market downturn. But remember that advisors are human too. During severe market panics, some lose their cool out of fear of losing clients and actually allow investors to sell at the absolute bottom.

9 & 10. The ultimate weapon is a written plan. We spend far too much emotional energy on money. Yes, it is a necessary tool to support basic life functions. But treating it as the ultimate goal, a measuring stick, or a definition of our self-worth only breeds anxiety and actively destroys our happiness.

One of the best weapons you have to fight this is a written financial plan. Drafting a clear, long-term plan when you are calm and the market is quiet provides a critical lifeline. It helps subtract your temporary emotions from the equation when market turbulence or personal anxieties inevitably strike.

I dive much deeper into all of these concepts in the latest episode. If you have ever felt like your brain is working against your bank account, you will want to tune in right now.

Community Update: Coaching and The Happiness Code

I want to share a quick update with you regarding my purpose-oriented coaching. I am currently raising my prices from $1,500 to $2,000 for a package of five one-hour Zoom sessions.

However, I am offering a special discount to listeners right now to help promote pre-orders for my upcoming book, The Happiness Code, which is slated for release in March 2027.

If you purchase 50 paperback copies of the book on Amazon (which costs roughly $1,000) and email me the receipt, I will give you the five-pack of coaching sessions for free. This essentially gives you the coaching at half price, plus you get 50 books to share with your friends, family, or colleagues. It is a true win-win.

Let me know what you think of the new episode in the comments!

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This is a historic day in our household.

I’m about to leave this morning with my wife to take my daughter to college. We are officially going to be empty nesters. I have a 21-year-old and an 18-year-old, and they will both be away at school this year.

Because both of my children are now adults and leaving the house, we decided it was time to hold our very first family financial meeting. My wife and I have always managed everything on our own, and while we’ve talked openly about money with our kids since they were little, they had never actually seen our accounts.

That changed this morning. I wanted to tell them exactly what we have, where it is, and what they need to do if something ever happens to us.

Laying Everything on the Table

We sat down, and I showed them every single one of our financial accounts.

I walked them through our banking at USAA, our brokerage accounts, and all of our business accounts. I showed them exactly where to find our passwords and how to access my password keeper. I opened my computer and introduced them to our ICE (In Case of Emergency) binder, showing them where the digital copy lives and where to find the physical safety deposit box key.

But I didn’t stop at the numbers. I explained the “why” behind the accounts. We discussed:

• Insurance: We reviewed our long-term care insurance, the life insurance policy attached to it, and the philosophy behind why we need it. I also explained why we decided to get rid of most of our life insurance policies once we became financially independent, as well as why we don’t need disability policies anymore.

• Asset Allocation: I walked them through the specific amounts in our brokerage and bank accounts. We talked about the philosophy behind our asset allocation, what we needed during our accumulation phase, and my plans for drawing those accounts down in the future.

• Estate Planning: My wife and I have an estate plan and trusts in place, which are all stored in our safety deposit box. Even though our kids know they are the beneficiaries and eventually receive everything on death, we use designated beneficiaries and transfer-on-death forms to bypass most of our trusts entirely. I went through each account with my kids to show them exactly how to access those funds directly.

This was the easy part.

The Real Reason for the Meeting

Next, I told them exactly what to do if something happens to my wife and me.

I outlined the kind of funeral and burial I want, and my wife did the same. We assured them that we’ve lived good, full lives, and if tragedy strikes, we don’t want them to panic. We gave them explicit instructions on what we want them to do with their lives and our money. We have wills and trusts to handle the legalities, but because those bypass the probate process via transfer-on-death forms, we wanted them to have absolute clarity on what to do with those assets.

But the point of this family meeting wasn’t just to hand over a morbid checklist. It was to help them understand exactly where we are, so they know what to do for themselves.

Up until now, my wife and I have managed our wealth—and the wealth our kids enjoy, like paying for college and their living expenses. It’s very clear to me that this phase is ending soon. They are going out into the world to make their own money.

I want them to know how to set up their own accounts, build their own lives, and secure their own financial futures. This meeting wasn’t just about informing them of our information; it was a way to model the exact financial behavior I think they truly need.

I plan to repeat this meeting once a year to update our information, review passwords, and check the ICE binder. We’ll have this conversation every August or September before they go back to school. It’s going to be a family habit that we carry out for the next few decades so we are always on the same page.

I don’t know if you are having these family meetings or not. I certainly hadn’t before today. But as I prepare to drop my children off and let them fly on their own, doing this has given me a massive amount of peace of mind.

Did you catch this week’s episode of Earn & Invest (Click to listen)?

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Over the years, I’ve spent a lot of time thinking about the anatomy of happiness. In my own life—and in my conversations with hundreds of guests on the Earn and Invest podcast—I’ve found that true fulfillment usually boils down to two distinct components: Purpose and Meaning.

Purpose is active. It’s the present and future-focused things we do that light us up and bring us joy.

Meaning, on the other hand, is cognitive. It’s the story we tell ourselves about our past. I’ve noticed a stark difference in how people frame these stories. Happy people tell heroic tales of overcoming trauma, ultimately arriving at a place where they feel they are “enough.” Unhappy people tend to hold onto victim stories, trapping themselves in narratives where they feel permanently stuck.

But what happens when you want to change your story, but no matter how hard you try, you keep falling into the same self-destructive financial or emotional patterns?

That is exactly what we explore in the latest episode of the podcast. I sat down with Michelle Masters, an internationally acclaimed personal development trainer and the author of Wired for Money. What followed was a fascinating look into the intersection of neuroscience, generational patterns, and personal finance.

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Michelle uses a brilliant analogy to explain why traditional therapy and our best conscious efforts to change our money habits often fail. Imagine your mind as a building. Your conscious mind is the penthouse, but your subconscious is the basement. If you have faulty wiring in the basement, sending a bunch of experts up to the penthouse to talk about it will never turn the lights back on. You have to physically go down into the dark and rewire the system at the source.

Our most deeply held (and often destructive) behaviors are driven by subconscious beliefs that were fully formed between the ages of three and six. During those early years, your brain was making about a million neural connections a second, absorbing your entire worldview based on your environment, your sense of safety, and how you experienced love.

If you absorbed the deeply ingrained belief that “you have to work hard to deserve money,” you’ve been carrying around a toxic joy-killer your entire adult life. And if you want to know what your hidden blocks are, Michelle suggests simply looking at your predictable life patterns. Do you always get ahead just to immediately lose it? Are you paralyzed when it comes to asking for what you’re worth? Your circumstances are perfectly describing what your subconscious actually believes.

In the episode, Michelle breaks down exactly how to rewire those neural pathways. We discuss:

• Family Constellation Work: How trauma and losses repeat across generations. (As a physician, I was fascinated by the modern epigenetics she shared—like how measurable PTSD markers can be found up to three generations down from D-Day survivors).

• Neuro-Linguistic Programming (NLP): How the brain encodes and stores meaning.

• Sensory-Based Visualizations: Why the oldest, survival-focused parts of our brain don’t understand English, and how to use pictures, sounds, and feelings to build a new “road” between your wise adult brain and your raw childhood experiences.

When people finally release these blocks, they often experience what feels like sudden financial windfalls or “money magic.” We talk about why this happens—both through the lens of Confirmation Bias (suddenly seeing opportunities that were always there but filtered out) and the Quantum Lens.

Ultimately, this episode is about generational growth. It’s about doing the hard, messy “meaning” work to stop generational trauma in its tracks, so we can model a healthy relationship with wealth and self-worth for our kids.

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I’ve been thinking a lot lately about the line between managing our own money and handing over the reins to a professional.

After a recent and incredibly insightful conversation with financial planner Dana Anspach, I decided to sit down and record a solo “10 Things” episode of the Earn and Invest podcast to tackle this exact dilemma.

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In the personal finance community, there is a loud, persistent narrative that you should always manage your own money to save on fees. But the truth is much more nuanced than that. The skills required to build wealth are fundamentally different from the skills required to safely spend it down.

To help make sense of it all, I split this new episode into two distinct halves: five insights for the accumulation phase, and five insights for the de-accumulation phase.

Here is a quick look at what I cover.

The Accumulation Phase (Things 1–5)

During your younger, wealth-building years, managing your own financial plan is actually fairly straightforward. In the episode, I explain why DIYing is so manageable early on:

1. It is easier during accumulation. When you are building wealth, your main goal is simply to heavily allocate your savings into broad-based equity index funds. It is actually quite difficult to make a catastrophic mistake here.

2. Emotions trump knowledge. The hardest part of this phase isn’t the math; it’s managing your own psychology. If you find yourself panic-selling when the market drops, hiring an advisor is a wise choice, not a failure.

3. Just keep buying. To borrow a phrase from financial writer Nick Maggiulli, continuously buying equities over decades is highly likely to result in long-term success.

4. Market beta is good enough. Chasing market-beating returns (”alpha”) through active stock-picking is incredibly difficult. Accepting standard market returns (”beta”) through index funds makes DIY investing highly manageable.

5. Bonds and cash are less important. When you have a reliable job (your “sweat equity”), you don’t need to drag down your long-term returns by holding excessive cash. You want equities to do the heavy compounding.

The De-accumulation Phase (Things 6–10)

Once you retire and stop earning a regular income, the financial landscape changes drastically. This is where safely DIYing becomes significantly harder:

6. De-accumulation is a different ballgame. Transitioning to spending down your wealth is highly complex. Mistakes with taxes, health insurance credits, or Medicare premiums (IRMAA) can cost you dearly.

7. Returns become less important. In retirement, your focus shifts from maximizing growth to risk mitigation. The goal is no longer pure financial efficiency; it’s preserving enough wealth to decrease your anxiety and let you sleep at night.

8. There are more decisions to make. How do you draw down taxable accounts vs. Traditional IRAs vs. Roths? How do you manage conversions and the Net Investment Income Tax? The sheer volume of decisions multiplies.

9. Cognitive slowing happens. As we age into our 70s and 80s, our decision-making abilities naturally decline. This makes retirees vulnerable to missing critical payments or falling for scams. Having a trusted professional or family member in place before this happens is vital.

10. You should think less about money. The ultimate goal of retirement is to focus on purpose, identity, and connection. If DIY administration causes you stress, paying for professional help to take that burden off your shoulders is a priceless investment.

Listen to the Full Episode

Are you struggling with the transition from building wealth to spending it? Do you wonder if you should finally hire an advisor to look over your drawdown strategy?

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Tune in to the full episode to hear me unpack each of these ten concepts in much greater detail, and learn how to build a financial plan that supports your life—rather than a life that revolves around your finances.

Join the Conversation I would love to hear your thoughts on DIY planning versus hiring an advisor. Send me an email and let me know how you are handling your own accumulation or de-accumulation phases.

Also, a quick reminder about our schedule here at The Purpose Code Substack: you can expect companion articles and show notes every Monday and Thursday, with traditional blog posts and community polls going live every Wednesday.

Thank you for being part of this community!

If you are part of the personal finance and financial independence community, you may have noticed a brouhaha brewing between two of our leading voices.

On one side is Karsten Jeske, who writes the incredible blog Early Retirement Now (and often goes by the moniker “Big Ern”). On the other side is Frank Vasquez, host of the wonderful podcast Risk Parity Radio.

The disagreement they are both facing revolves around one core idea: what is the best decumulation asset allocation? Specifically, they are debating the concept of risk parity.

The Great Decumulation Debate

I won’t dive too deeply into the weeds of explaining exactly what risk parity is. If you aren’t deeply embedded in these communities, you don’t need to know the nitty-gritty to understand the broader lesson here.

You see, Frank Vasquez is a big proponent of using the risk parity model for spending down our asset allocation in order to spend the most money. Karsten Jeske, however, believes that risk parity actually does the exact opposite—that it can cause us to have a lesser amount of money to spend down.

Let me start by saying that I am a fan of both of these thought leaders and content creators. In fact, when I am alone with Frank, he can totally convince me that risk parity is the way to go. On the other hand, when I am alone with Karsten, he can completely convince me that risk parity isn’t the way to go.

Why? Because they are both experts. They both use important data, and they are both able to fashion that data to prove their points.

But here is my problem with both of their approaches.

The Trap of Predicting the Future

Predicting the future is impossible. It is a fool’s errand.

When you look at people trying to make a point in personal finance, they typically rely on one of two things to predict the future:

• Backtesting: We look at the past and consider it prologue. But we all know that none of us can truly tell the future, and we certainly don’t know if the future is going to perfectly mirror the past. If you winnow down enough information from the past, you will eventually find variables that ran together historically. That doesn’t mean one caused the other, and it doesn’t mean they will happen together in the future.

• Simulations: We use Monte Carlo simulations to model possible future markets. The problem with simulations is that they are only as good as their inputs. You can fudge those inputs—change inflation slightly, tweak a specific return estimate, alter any small variable—and your simulation will be wildly off.

So, who is right? Is Frank right? Is Karsten right?

The truth of the matter is, none of us know. The future is a leap of faith. Spending down your portfolio and retirement decumulation are leaps of faith.

What Actually Matters

I don’t think predicting the future matters. I think what Frank and Karsten are doing is very brave, but I don’t think it answers the real question.

Instead of deciding which strategy is mathematically “better,” I suggest you ask yourself two completely different questions about your asset allocation:

1. Which plan are you more likely to stick with? (Could you actually manage a risk parity portfolio without getting overwhelmed?)

2. Which one will allow you to sleep at night? (If the answer is a traditional 75/25 asset allocation like Karsten often talks about, then go with that!)

We don’t know whether Frank or Karsten is going to be mathematically “right” in the end and that’s perfectly fine.

Why? Because you are not going to make an asset allocation decision today and blindly live the rest of your life that way, no matter what happens. You are going to see what happens in the present and the future, and you are going to pivot.

The Mark of a Wise Investor

Pivoting is more important than whether you start in the “right” place. Whether you decide to go with risk parity or not, whether you choose any specific decumulation strategy or not, isn’t nearly as important as paying attention every year and adjusting as necessary.

Predicting the future is a fool’s errand. But acting in the present to make a better future? That is what a wise person does.

And don’t you want to be wise?

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I have spent years working as a hospice physician. I have sat at the bedsides of hundreds of dying patients, holding their hands and guiding their families through the most difficult transition of their lives. Because of this, I often tell myself that I am inoculated against the fear of aging.

But I have a confession to make: this week on the podcast, I got shaken.

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I was interviewing Dana Anspach—a brilliant certified financial planner, retirement management adviser, and the author of Living Off Your Acorns. While preparing for the episode, I read her description of the final phase of retirement. Despite all my medical training, the reality of my own eventual aging hit me like a ton of bricks. We had a profound conversation in the after-show segment about this, reflecting on how our respective careers—hers as a financial planner, mine as a doctor—have granted us a privileged window into hundreds of lives. We get to see in real-time who ages gracefully, and who struggles.

Dana’s core philosophy is that retirement is not a single, static event where you simply flip a switch and stop working. It is an evolution. She breaks this down into an incredible framework called the Four Seasons of Retirement.

Here is what that journey actually looks like:

1. The Pre-Go Years

This is the decade leading up to retirement, and ironically, it is often the most financially stressful. The transition is finally a visible horizon. This is the phase where we obsessively run our numbers through every possible Monte Carlo simulation to combat a very specific, deep-seated anxiety: the terror of losing our regular paycheck.

2. The Go-Go Years

These are the early, active years of retirement—usually lasting through your early 70s—where energy is high and the world is open. You will likely spend more money here, funding travel, home renovations, and new hobbies. But it also introduces massive new complexities. Suddenly you are navigating private health insurance, COBRA, Medicare, quarterlies for the IRS, and setting aside cash for lump-sum home repairs.

3. The Slow-Go Years

Eventually, the travel bugs fade. You naturally begin to slow down and find a deep, quiet contentment in a comfortable home routine. As your personal spending declines, your focus often shifts outward toward legacy: gifting to children, funding grandchildren’s education, or supporting charitable causes. Crucially, this is the time to start using your wealth to hire help for household chores to protect your physical safety.

4. The No-Go Years

This is the phase that got to me. This is the final season, where physical and cognitive health concerns take center stage. Because cognitive decline can subtly strip away the self-awareness you need to recognize your own limitations, Dana stresses one absolute necessity: you must establish a trusted relationship with an advisor or bring family members into your finances before this phase begins. When the time comes, they act as the critical guardrails against financial mismanagement, missed insurance premiums, or elder scams.

The Leap of Faith

What I love about Dana’s approach is that it forces us to admit a hard truth: retirement is far more than a math problem.

In the financial independence community, we have a terrible habit of stacking overly conservative assumptions on top of each other. We project historically low market returns, pair them with sky-high inflation, and model for worst-case scenarios until we are completely paralyzed by fear.

We act like rigidity is a superpower. It isn’t. Rigidity is a planning weakness.

Life is wildly unpredictable. As Dana realized during a two-week vacation in Colorado that changed her own trajectory, you eventually have to stop “powering through” burnout and start intentionally following your energy. You have to embrace a looser, more optimistic framework.

At the end of the day, leaving the safety of the workforce is a leap of faith. You cannot spreadsheet your way to courage. You simply have to build a flexible plan, take the jump, and trust your ability to pivot as the seasons change.

I want you to hear this conversation. It is a masterclass in bridging the gap between the math of wealth and the emotion of aging.

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Let me know which of the four seasons you might struggle with, and how you are preparing for the future.

Chautauqua is gone, but its greatest lesson remains: The math of financial independence is easy. Figuring out who you are on “day plus one” of early retirement is the hard part.

I still remember how isolating it felt when I first discovered financial independence.

I was burning out in my medical career, quietly devouring blogs and podcasts, running the numbers in my head on a loop. But I had a massive problem: I didn’t have a single person in my real life I could actually talk to about it. If you tell your friends or colleagues that you are planning to walk away from a high-paying, prestigious career in your forties to do nothing, they look at you like you have two heads.

That all changed for me in 2018. I finally took a leap of faith and attended an in-person financial community event.

Being in a room with people who just understood changed everything. It gave me the mental fortitude and the courage I desperately needed to finally let go of my identity as a traditional doctor. Blogs and podcasts are incredible for sharing information. But in-person events? They change what you believe is possible.

For our Earn & Invest rewind this week, we are opening the vault to revisit a classic 2022 conversation about a legendary event that embodied this magic better than almost any other: Chautauqua.

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While Chautauqua has since closed its doors and no longer holds retreats, its impact on the Financial Independence (FI) movement is permanent. In this episode, I sat down with a powerhouse panel of FI leaders—JL Collins (The Simple Path to Wealth), Bryce and Christie (Millennial Revolution), and Alan and Katie Donegan—to pull back the curtain on these intimate, week-long gatherings.

If you aren’t familiar with Chautauqua (an old Native American word meaning a gathering of people to share stories and ideas), you might assume a week-long financial retreat was just spreadsheets, tax optimization, and withdrawal rate debates.

The surprising truth? We spent very little time actually talking about money.

As Bryce points out in the episode, achieving FI is just a math problem. The math is the easy part. But figuring out how to live a happy, fulfilling life after leaving the rat race? Dealing with the terrifying transition of “day plus one” of retirement? That is much, much harder.

Even though you can no longer buy a ticket to Chautauqua, the lasting truths we discussed in this episode are exactly what anyone pursuing financial independence needs to hear today. We talk about:

• The Power of Environment: How stepping out of your daily routine and into a beautiful, completely managed environment frees up your mental bandwidth. When you stop worrying about logistics, you finally have the space to think, write, and figure out your actual purpose.

• The Intimacy of Shared Goals: Chautauqua was strictly capped at 30 people. By Tuesday or Wednesday, the surface-level small talk evaporated, and a group of “outliers” formed a tight-knit family. We need to intentionally seek out and build these micro-communities in our own lives.

• The Internal Transformations: We share stories of the “dragged-along” skeptical spouses who ended up becoming massive champions of the movement, the introverts who found their voice, and the attendees who sat down for a 1-on-1 session only to realize they were already wealthy enough to quit their jobs—they just needed permission to believe it.

In this 2022 time capsule, we were preparing to head to Colombia, and I was getting ready to speak about what my dying hospice patients taught me about living a good life.

While the event itself belongs to FI history, the message is timeless: You cannot do this alone, and your spreadsheets won’t save you if you don’t know who you are without your job.

If you have ever felt misunderstood by your peers, or if you are struggling with the emotional weight of transitioning out of your career, you need to hear this conversation.

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Have you ever attended an in-person FI event or meetup? Did it change your trajectory? Hit reply or let me know in the comments.

Last week, I wrote a post detailing exactly why I despise bucket systems and complicated drawdown strategies. I shared my dead-simple approach: starting with a 70/30 portfolio and simply selling off the bonds over time.

The reaction from the personal finance community was swift and predictable.

Time and again, the pushback centered on a single word: efficiency. People jumped into the comments to tell me that bonds are a lost cause, that my strategy was woefully inefficient, and that I was leaving equity returns on the table. Why are you doing this? they asked. You could make so much more money if you just optimized.

My answer to them is simple, though it flies in the face of everything we are taught as investors: You are looking at the wrong thing.

I believe the relentless pursuit of financial efficiency is making us miserable. Here is why.

The Myth of the Depleting Portfolio

If you look at the EBRI research study released in May 2026, the data paints a fascinating picture of modern retirement. It showed that one in three retirees reach their mid-80s with their original savings completely intact—or even greater than the day they first retired.

This gets to the heart of a massive behavioral trap. In the financial independence community, our net worth goals are rarely based in absolute reality. Instead, they are built by stacking conservative assumption on top of conservative assumption. We build in massive margins of safety because we need that high valuation to give us the “escape velocity” required to confidently leave our jobs and walk away from an income.

That behavior isn’t mathematical. It is deeply emotional.

But here is the catch: once a retiree crosses that finish line, they almost always have too much money. Based on the EBRI data and countless conversations I have had with financial advisors, the vast majority of these diligent savers are going to die with millions. They will enter their mid-80s with the same, if not more, wealth than they started with.

Yet, instead of enjoying that security, they are spending their golden years crippled by undue stress. They obsess over their asset allocation. They agonize over squeezing out a slightly higher return. They are desperately trying to be perfectly efficient with money they aren’t even spending.

The Emotional Tax of Optimization

When we talk about happiness, we usually agree that it isn’t directly correlated with the numbers in your bank account. True happiness comes from a sense of purpose, deep connections, and a solid sense of identity.

But while money might not create happiness, it can absolutely destroy it by introducing anxiety and stress.

Some people spend hours of their precious time worrying if their retirement strategy is efficient enough. But if happiness is tied to purpose and connection, and anxiety actively detracts from that happiness, then the stress of being “efficient” is a net negative.

In other words: the anxiety of optimization is actively decreasing your happiness. The marginal economic gains you might get from a perfectly efficient portfolio are entirely unnecessary, and they are costing you your peace of mind.

Permission to Be Inefficient

We need to purposefully let go of efficiency.

When we talk about decumulation and drawing down our portfolios, we have to stop worrying so aggressively about our returns and how “perfectly” we are managing our investments.

Perfect is the enemy of good. In personal finance, 80% is enough.

The people criticizing my dead-simple asset allocation aren’t doing it because optimizing will actually help me live a better, more fulfilling life. They are doing it because of a deep-seated anxiety caused by the need to be mathematically perfect.

This anxiety is exactly why books like Die With Zero have become massive cultural phenomena. We have become so overly conservative and worried about our net worth estimations that we literally need a multimillionaire author to lambast us into spending our own money.

The easier solution? Stop worrying so much about the spending, and stop worrying about accumulating more.

If you aren’t going to shoot for a lower net worth number because you need that psychological escape velocity to retire, then you must at least do this: allow yourself to be less efficient in retirement.

Let go of the financial anxiety. Accept a “good enough” yield. Use the money for exactly what it was meant to do for you in the first place—allowing you to relax, have a little fun, and worry just a little bit less.

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The hardest part about getting rich? Staying rich.

When I sat down with Victor Haghani on a recent episode of the Earn & Invest podcast, he shared an old adage passed down from his father: It is harder to hold onto money than to make it.

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In the personal finance community, we spend an incredible amount of energy talking about how to build our net worth. But making a fortune usually requires taking massive, asymmetric risks over a long period. Keeping that fortune requires something entirely different—disciplined risk mitigation. And because wealth decisions happen over decades, maintaining that discipline over a lifespan is incredibly challenging.

Victor knows exactly what happens when risk gets out of control. Today, he is the founder of Elm Wealth, but back in the 1990s, he was a co-founding partner of the hedge fund Long-Term Capital Management (LTCM).

For years, LTCM enjoyed spectacular success, averaging annual returns of 40%. Then came October 1998. Through leveraged positions, the fund lost 92% of its capital, ultimately requiring 14 banks to step in and inject $4 billion just to liquidate the portfolio.

Victor took that brutal experience and wrote The Missing Billionaires: A Guide to Better Financial Decisions. In our conversation for Earn & Invest, he broke down why so many of us are looking at risk the wrong way.

Here are a few concepts from the episode that completely shifted my perspective:

Risk Eats Compound Return

Victor pointed out that average annual returns can be highly misleading. Imagine you make 50% one year and lose 50% the next. Your average return is technically zero, but your actual compound loss is 25%. During LTCM’s run, the average annual return remained positive (around 20%), but an investor who left their money in the fund finished with a compound return of -100% once they lost everything.

The biggest takeaway here is diversification. Never concentrate too much of your wealth in your own business—a painful mistake also made by employees at Enron and Lehman Brothers.

The Gummy Bear Problem (Expected Utility)

Instead of striving to amass as much nominal wealth as possible, Victor argues we should focus on maximizing expected utility—the happiness and welfare we get from spending and giving money away. Wealth is subject to decreasing marginal utility. Earning an extra dollar doesn’t bring nearly as much joy as losing a dollar brings pain. Victor compares it to eating gummy bears: each additional one brings a little less incremental happiness. Because we are naturally risk-averse, the rational goal of investing is actually to maximize risk-adjusted wealth.

Your Spending and Investing Are Inseparable

Victor highlighted the lifetime consumption models developed in the late 1960s by MIT economists Paul Samuelson and Robert Merton. Their work proved that an individual’s spending policy and investment policy are inexorably connected. It is highly suboptimal to maintain a fixed spending policy (like a rigid “4% rule” adjusted for inflation) while holding a highly volatile, risky investment portfolio. To avoid bankruptcy, you have to be willing to adjust your spending when your portfolio declines, basing your de-accumulation on a portfolio’s risk-adjusted, after-tax, inflation-adjusted expected real return.

Sizing Over Selection

Turn on the financial news, and 99% of the coverage is about what to buy—hot stocks, index funds, or crypto. Active stock picking is a highly competitive, zero-sum game where you must beat institutional giants.

Victor asserts that how much you invest (bet sizing) is far more critical. Sizing is a non-competitive, positive-sum decision tailored strictly to your own risk tolerance. You can survive getting the “what” decision wrong as long as your sizing is correct. But if you get your sizing wrong, you can be completely ruined—even if you picked the right assets.

We also talked about how DIY investors can use this exact framework for practical everyday decisions without needing complex math. It can be as simple as intuitively determining how much guaranteed return you would accept to give up a volatile equity portfolio, or opting for the highest possible deductible on health or home insurance to save on premiums while taking on a tolerable level of personal risk.

If you want to stop obsessing over what to buy and start mastering how much, check out the full episode on your favorite podcast player. Let me know what you think in the comments!

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In a recent episode of the Earn and Invest podcast, I had a profound conversation with Dr. Santi Tanikella about a very specific, modern affliction: the deep, “guttural loneliness” so many adults feel today.

It is that hollow feeling that creeps in even when you’ve done everything right on paper. You have the job, the house, the savings rate—but something is still fundamentally misaligned.

That conversation stuck with me. It inspired me to sit down behind the mic for a solo “10 Things” episode to share some of the life advice I’ve gathered over my 53 years on this planet. Drawing from my own experiences as a hospice physician, a podcaster, and a coach, I wanted to outline ten ways we can step out of that loneliness and back into our own lives.

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Here is a quick look at the ten things I break down in the episode:

• Thing 1: Forgive yourself. You’re better than you think. Most of us walk around blinded by our own feelings of inadequacy. Take a step back. You are actually quite smart, capable, and financially savvy. Give yourself some grace.

• Thing 2: Most people are less happy than you. Social media is a toxic facade where everyone appears to be living a flawless life. Stop playing the comparison game. Behind closed doors, most people are privately struggling just as much, if not more, than you are.

• Thing 3: Attempts are more important than success. I have sat at the bedsides of the dying for years. I can promise you this: people at the end of their lives do not regret their failures. They regret the deeply important things they never had the courage to try. True contentment comes from intentionally putting yourself in the arena.

• Thing 4: Put purpose and identity first, money second. This is a massive flaw in the Financial Independence community. We prioritize net worth and frugality over meaning. If you accumulate wealth without knowing what lights you up, you will just end up with a lot of money and a very “little life” devoid of connection.

• Thing 5: When it comes to money, be less efficient. Perfect is the enemy of good. Stop wasting hours obsessing over the perfect tax hack or stressing over the highest possible safe withdrawal rate. A “good enough” financial plan leaves you more time to actually go out and live your life.

• Thing 6: Authentic vulnerability rarely backfires. Artificial vulnerability will draw criticism, but sharing your genuine truths with good intentions is an absolute superpower. It fosters deep human connection and opens the door to new opportunities.

• Thing 7: Displaying your Achilles heel strengthens it. Hiding your weaknesses and keeping secrets creates a life of constant fear—it is death by a thousand cuts. Openly exposing your vulnerabilities completely removes the power others have to use them against you.

• Thing 8: Humility and confidence can (and should) coexist. Confidence without humility breeds arrogance. Humility without confidence prevents you from sharing your talents with the world. You need the self-awareness to carry both.

• Thing 9: Life is long. You won’t miss out. There is a panicked “carpe diem” mindset that tells us we have to do everything right now. But life is abundant. It is full of different seasons and rich with second chances. Don’t stress over missing out on any single opportunity.

• Thing 10: Love lifts you, and it will always hurt. Loving anything—a spouse, a friend, a passion—inevitably ends in loss and pain. You cannot protect yourself from it. Pain is the inevitable reward for a life well-lived, so you must choose to love anyway.

A Note on Who This Is For

In the after-show segment of this episode, I read a fantastic, anonymous email from a listener. They pointed out that my content tends to resonate much more heavily with a higher net-worth demographic rather than FI beginners who are just trying to scrape together their first million.

I completely agree with this assessment.

There are countless incredible creators out there teaching the basic mechanics of investing, budgeting, and safe withdrawal rates. I intentionally leave those topics to them. My goal with Earn and Invest has always been to facilitate “next level” discussions. I want to talk to the people navigating the complex, often messy reality of post-FI life—the people trying to figure out what comes after the spreadsheets.

If you are ready to move beyond the math and start doing the deep work of aligning your money with your purpose, this episode is for you.

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If you read almost any modern personal finance book, you will eventually stumble across the exact same advice for managing your money in retirement: use a “bucket” strategy.

The strategy is designed to protect you from sequence of returns risk—the very real danger of experiencing a market crash during your first few years of retirement, which can decimate your portfolio before it has a chance to compound.

To prevent this, the bucket strategy divides your assets into three distinct categories:

• A long-term bucket: Exclusively for equities.

• An intermediate bucket: Filled with bonds, CDs, and treasuries.

• An immediate bucket: Kept in cash to fund your day-to-day lifestyle for the next year or two.

It sounds incredibly smart in theory. But I have a confession to make: I hate buckets.

Here is exactly why I think this popular strategy is flawed, and the experimental, radically simplified approach I plan to use for my own decumulation phase instead.

3 Reasons the Bucket Strategy Fails

1. It discounts the equity premium Over long periods of time, equities simply perform better than almost everything else. In fact, studies show that an all-equity portfolio in retirement regularly outperforms almost every other asset allocation over the long haul. When you take a massive chunk of your portfolio out of equities just to fill your cash and intermediate buckets, you are actively choosing to accept lower returns.

2. It is dangerously conservative In the Financial Independence community, we already start with highly conservative assumptions. The standard 4% safe withdrawal rule already accounts for some of the worst sequence of returns scenarios in modern history. When you force a bucket strategy on top of the 4% rule, you are layering a conservative strategy over an already conservative baseline. This guarantees you will have less money to spend. If you want to protect yourself, you are much better off using a 5% withdrawal rate and implementing simple guardrails—like deciding to skip an inflation adjustment or cutting your spending by 10% during a down market year.

3. It is a logistical nightmare Bucketing sounds incredibly simple until you actually have to manage it. You are constantly forced to calculate exactly how and when to move money from the high-risk bucket down to the intermediate and low-risk buckets. It introduces massive decision fatigue. There are so many moving parts that most people end up hiring a financial advisor just to execute the strategy properly. Worse, the complexity creates a high likelihood that you will eventually lose your courage, panic during a downturn, and abandon your own plan.

My Solution: The “Never-Rebalance” Glidepath

I want to avoid the decision fatigue of buckets entirely. While I haven’t back-tested this with historical data yet, I have been working on an experimental strategy for my own decumulation phase that removes the guesswork.

When I entered the decumulation stage last year, I naturally let my portfolio settle into a 70/30 allocation—70% in equities and 30% in bonds. Going forward, I plan to draw my “paycheck” quarterly using one incredibly simple metric: the S&P 500.

• If the S&P 500 is higher than it was last quarter, I will draw my cash from the equities side of the portfolio.

• If the S&P 500 is lower than it was last quarter, I will draw my cash from the bonds side of the portfolio.

Here is the absolute most important rule of this system: I am never going to replace my bonds.

If I drain bonds during a down quarter, they stay drained. If, following this rule, I eventually end up with a bond-weighted portfolio, only then will I rebalance to equities.

By following this rule, over the course of eight to ten years, I will eventually spend down more and more of those bonds. My portfolio will naturally glide into a 100% equity allocation.

This makes perfect logical sense. Sequence of returns risk is primarily a danger during those first six to seven years of retirement. Once you survive that initial window, the risk drops dramatically. Gliding your equities up as your sequence of returns risk goes down is exactly what you want to happen.

Yes, depending on whether you are selling from a Traditional IRA or a taxable brokerage, there is some tax arbitrage you have to figure out along the way. But the overarching philosophy takes the anxiety out of the equation. There are no buckets to refill, no complex formulas to track, and no constant second-guessing. You simply look at the market once a quarter, make your withdrawal, and get back to enjoying your life.

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Have you ever reached a point where you looked at your life, realized you had checked all the right boxes, and yet felt a profound, guttural loneliness?

It is a specific type of exhaustion that you can’t just sleep off. My guest on this week’s episode of the Earn and Invest podcast, Dr. Santi Tanakella, calls this a “burnout of the soul.”

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Dr. Tanikella is a board-certified pediatrician, an integrative medicine specialist, and a certified life coach. In our conversation, we dug into why so many successful adults feel this deep disconnect, and more importantly, how we can begin to realign with our true selves.

If you are feeling the heavy weight of modern burnout, this episode is a must-listen. Here is a look at what we discussed.

The Eight-Year-Old Test

In the heavily siloed American medical system, we are taught to separate physical ailments from emotional ones. If your stomach hurts, we look at your stomach.

Dr. Tanikella practices integrative medicine, drawing heavy inspiration from her Ayurvedic roots, which treats the mind, body, and spirit as one cohesive unit. A core tenet of this philosophy involves taking a hard look at who you fundamentally are.

To do this, she suggests comparing your current adult self to the pure, intensely curious kid you were at seven or eight years old. When those two versions of yourself are profoundly misaligned, it results in that guttural loneliness we so often feel in adulthood. And here is the hard truth for those of us in the personal finance space: you cannot fix that misalignment simply by getting a better job or making more money.

The Trap of the Modern Treadmill

This internal misalignment is massively exacerbated by the noise of modern life. We are constantly tethered to our cell phones, managing the guilt and tug-of-war of family obligations, and battling the relentless creep of a career that always asks us to do just a little bit more.

When I asked Dr. Tanikella how finances play into this, her answer struck a chord.

Money is undeniably essential. It meets our basic needs and builds a necessary safety buffer between us and disaster. But when we let money rule our decisions, it almost always pulls us away from our authentic path. She shared a deeply personal story of the anger she felt when mentors advised her to abandon her dream of becoming a physician for a “more convenient” career in computer programming—simply because she was a woman who might want to be a mother someday.

She didn’t listen. She chose alignment over convenience.

Redefining Success in Life and Love

A major theme of our conversation was shifting how we measure success.

• In Relationships: A successful marriage does not require a 100% overlap in hobbies or interests. It means being able to truly see, accept, and appreciate your partner’s differences without losing your own identity or slipping into toxic codependency.

• In Your Career: True success isn’t measured by quantity. It is not about the hours you logged or the sheer number of patients you saw. It boils down to one simple question: “Did I help someone today?”

Leaning Into the Discomfort

So, how do we step out of this loneliness? According to Dr. Tanikella, the biggest stumbling block is a lack of self-compassion.

We guilt-trip ourselves endlessly and create elaborate excuses to avoid making difficult changes. To break the cycle, she urges us to deliberately lean into discomfort. Stay late at that community event to make friends even if you feel awkward. Admit a mistake to a client or a patient. Navigating that vulnerability is exactly how true trust, healing, and community are built.

A Personal Reflection on Coaching

In my solo wrap-up for this episode, I reflect heavily on this idea of self-alignment.

Back between 2010 and 2012, I was drowning. I was working 80-hour weeks in traditional medicine and losing myself in the process. Desperate, I hired an executive physician coach. I credit that coaching with helping me improve my marriage, hone my writing skills, and ultimately giving me the courage to question my assumptions about my own identity.

That single decision to look inward is what eventually led me to discover financial independence and gave me the permission to walk away from traditional medicine.

Make sure you stick around for the post-credits chat, where Dr. Tanikella discusses her recent work coaching families through the lingering social regression and disrupted dynamics caused by the COVID-19 pandemic. It is a fascinating add-on to an already incredible conversation.

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We don’t budget, we spend a lot, and we aren’t dying with zero. Here is a look at how we actually manage our money, and why I recently walked away from a massive career milestone.

If you spend enough time in the Financial Independence, Retire Early (FIRE) community, you start to hear the same rigid rules repeated over and over. But the truth is, my wife and I manage our wealth in ways that completely defy the traditional rules of the personal finance and FIRE communities.

In the latest solo “10 Things” episode of the Earn and Invest podcast, I decided to pull back the curtain and outline exactly how we do things differently.

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Here is a breakdown of the ten things we do differently with our finances:

• Thing 1: We don’t budget. Despite the popularity of budgeting tools, my wife and I have never maintained a formal budget. During our wealth-building years, we simply lived off one spouse’s income and saved the other.

• Thing 2: We spend a lot. I completely reject the common FIRE goal of living on an artificially low budget like $40,000 a year. For example, our family’s COBRA health insurance alone currently costs $36,000 annually. We embrace high spending, and the massive tax bills that come with it, because money is ultimately meant to be spent.

• Thing 3: We continue to make money. Even though I consider myself retired, I still earn an income from my part-time hospice work, podcasting, and speaking engagements. If you are doing purposeful work that you love and people are willing to pay you for it, there is no reason to turn that money down.

• Thing 4: We say yes. To completely eliminate decision fatigue, we default to saying “yes” to major purchases. As long as an expense is below a certain threshold—which I currently anchor as high as a $100,000 for a once-a-year purchase—we buy it without stressing over the math.

• Thing 5: We spend for ease. A core tenet of our philosophy is using money to remove friction from our lives. Rather than doing chores to save a few dollars, we enthusiastically hire nannies, house cleaners, and grocery shoppers to eliminate the daily tasks that cause stress and anxiety.

• Thing 6: We don’t worry about spoiling our kids. I do not buy into the “shirtsleeves to shirtsleeves in three generations” fear. I freely gift my children money, believing that modeling excellent financial behavior and investments is a far better teacher than artificially making their lives difficult.

• Thing 7: We are open about our wealth. My children know the exact details of the family’s net worth and business investments. I want to be entirely transparent about my financial successes and failures so my children understand how to take maximal agency over their own lives.

• Thing 8: We still live below our ability. Despite our comfort with spending heavily on convenience, we do not push our spending to its maximum potential. We could easily buy nicer cars or bigger houses, but we choose not to because those upgrades wouldn’t remove any remaining friction from our lives.

• Thing 9: We will not die with zero. Pushing back against the popular “Die with Zero” philosophy, I have no interest in the anxiety-provoking task of perfectly spending down my portfolio. I find that expensive “memory dividends” from lavish vacations are fleeting compared to the sustained joy I get from my daily, purposeful work.

• Thing 10: Money rarely makes us happy. Recognizing the decreasing marginal utility of wealth, I’ve noted that once a person reaches a few million dollars, additional millions do absolutely nothing to increase their baseline happiness. I actively divorce money from happiness, realizing that true joy comes entirely from relationships and purpose.

Stepping Off the Achievement Treadmill

In the episode’s after-show segment, I also reflect on a very personal struggle: the “achievement treadmill”.

I recently secured a highly successful blogging gig for a third party that netted over a million views and international media attention in less than a year. However, because I lacked editorial control and didn’t genuinely enjoy the writing process, it only brought me anxiety.

Despite the negative impact on my brand, I walked away from the gig.

I am finally finding peace by abandoning the need to endlessly prove myself through professional achievements. I prefer to just be “Jordan”—a calm, happy person who goes on walks and spends time with his wife.

If you want to hear the full breakdown of our financial philosophy and my thoughts on letting go of the need to constantly achieve, be sure to listen to the full episode of the Earn and Invest podcast.

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I have argued previously that the Maslow pyramid is completely wrong. The different psychological levels—physiological, safety, love and belonging, esteem, and self-actualization—are traditionally presented as a pyramid, but the truth of the matter is that to be truly happy, we usually want to be doing some of all of them at the exact same time.

I have been thinking about this for a long time, and I believe the pyramid is either upside down or just entirely backward. If you want proof, look no further than the Financial Independence, Retire Early (FIRE) community.

The Trap of the Bottom Layers

Let’s look at the base of Maslow’s pyramid. The beginning consists of the basic things you need:

• The first level is physiological, which includes breathing, food, water, sleep, homeostasis, and excretion.

• While mostly physiological, things like food and water obviously cost money.

• The second level is safety, encompassing the security of your body, employment, resources, morality, family, health, and property.

• This second level is much more financial; we are talking about having enough money and safety.

It is only after we get past these highly financial physiological and safety levels that we reach the higher-level stuff:

• Level three covers love and belonging, including friendship, family, and intimacy.

• Level four is esteem, which includes self-esteem, confidence, and achievement.

• Level five is self-actualization, focusing on morality, creativity, spontaneity, and problem-solving.

The fundamental problem with this pyramid is that the first two levels are where most people spend their time struggling. We build up this financial importance to such an extreme point that many people decide making enough money to be safe is actually the entire point of life.

Exhibit A: The FIRE Community

The FIRE community is a perfect example of this trap. We get so wrapped up in financial independence and the idea of having enough money that it becomes our overall goal.

But what happens when financially independent people reach our goal at age 35, 40, or 45? Many of us actually find ourselves anxious and worried because we didn’t work on the upper parts of the pyramid—love, belonging, esteem, and self-actualization.

Instead of going out and working on those higher-level things, a lot of the FIRE community just spends more time doubling down on the money. I certainly did at first.

• We argue endlessly about safe withdrawal rates.

• We argue that the 4% rule is not good enough and that it should really be 3% or 5%.

• We suffer through one more year syndrome, deciding it is easier to just keep working rather than move out of the financial part to tackle the bigger things like love, esteem, and self-actualization. The rationalization? We might not have enough money! Our plan might fail.

We talk about financial metrics ad nauseam.

Flipping the Pyramid

This is exactly why I think Maslow has it completely wrong. We should not be thinking about physiological needs and safety first. We should be thinking about self-actualization, esteem, love, and belonging.

We need to decide who we want to be, what is important to us, and who the people are that we should be connected to. Those things should actually come first, and our finances should be somewhat of an afterthought.

Yes, you absolutely need enough money to have some kind of shelter and food. Let’s be honest, though: most people reading this or listening to my material are not struggling at that baseline physiological level; they have all far surpassed that. Even people globally and in the US who aren’t in the FIRE community aren’t always struggling at that level.

So why are we getting so caught up in the financial layer that we fail to move on to the other things?

The bottom of the pyramid is holding a lot of us in the FIRE community back. It is keeping us in an immature state where we never get past the money issue, simply because the money issue is the easy issue. It is something you can argue about, fall prey to for one more year, and get completely stuck on.

If we truly want to fix things, we have to stop looking at our spreadsheets. We need to start looking at our lives first, and then build our spreadsheets around that big, beautiful life.

Jesse Mecham built an empire on the word “budget.” Now, he wants us to abandon it. Here is why you need to listen to this week’s episode.

If I told you that the founder of the most popular budgeting software on the market—literally named You Need A Budget (YNAB)—wanted you to stop using the word “budget,” you would probably think I was joking.

But I’m not.

In this week’s episode of the Earn and Invest podcast, I sit down with Jesse Mecham to discuss his upcoming book, Never Worry About Money Again. What unfolds is one of the most fascinating conversations we’ve had on the show about the psychology of spending, the scarcity mindset, and how to finally take the anxiety out of our finances.

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If you have ever felt like managing your money is a restrictive chore, this episode is going to completely change how you view your bank account. Here is a sneak peek at what we dive into.

The Problem with the “B” Word

Despite building a massive, fiercely loyal brand with “budget” right in the name, Jesse realized a hard truth: the word itself acts as a psychological ball and chain for most people.

Society inherently views budgeting as a mandate to restrict, scrimp, and suffer through a scarcity mindset. We view it as a punishment for our financial sins. But Jesse argues that the true goal of financial planning is never deprivation. Instead, it is about figuring out exactly what you want to use your money for and building a system that allows you to do it guilt-free.

A Radical Mindset Shift: “Your Money is You”

To fix our relationship with spending, we have to fundamentally shift how we view a dollar. Jesse introduces a beautiful concept: “Your money is you.”

When you earn a paycheck, you aren’t just receiving paper or digital digits. You have traded your literal time, your physical energy, your education, and your intellect for it. Money represents your actual life force.

When you elevate money to represent your life energy, you stop viewing financial management as an annoying chore. Instead, it empowers you to spend it on things that reflect your true identity, allowing you to put pieces of yourself into the world.

What is Your Money For?

Once you respect money as an extension of yourself, Jesse suggests asking one simple, powerful question: What is the money for?

In the episode, we break down his five distinct areas for answering this question:

• For Now: Covering immediate, present-moment needs like groceries or the electric bill.

• For Later: Preparing for upcoming expenses, like an insurance premium due next week.

• For Ease: Building a buffer between earning and spending to optimize your system and eliminate day-to-day timing stress.

• For You: Spending that brings you personal joy and fulfillment in the present moment.

• For Change: Using money to alter your present reality, whether by funding personal health goals or making a broader impact on the world.

By answering these questions, you regain agency over your life. Asserting this control drastically reduces financial anxiety, whether you are a chronic over-spender or a fearful hoarder.

My Own De-cumulation Irony

This conversation hit incredibly close to home for me, and I spend some time in my solo wrap-up reflecting on a deep, personal irony.

During my wealth-building years, I never actually used a budget. My family simply invested my wife’s entire salary while living exclusively off mine. We spent freely until the checking account ran low, and that was that. It was remarkably hands-off.

However, now that I am in the “de-cumulation” phase of semi-retirement, I am suddenly forced to meticulously track my spending to determine exactly how much of my portfolio I need to liquidate each quarter. I admit on the show that I intensely dislike this new reality. It is a stark warning to anyone pursuing FIRE: early retirement often requires you to think more about money and budgeting than you ever did while working.

The Ultimate Truth About Your Nest Egg

Stick around for the after-show segment, where Jesse and I discuss a blunt, uncomfortable reality for many early retirees: money ultimately only has one use—to be spent.

Even money designated for “saving,” “taxes,” or “charity” is just delayed or delegated spending. If you are an early retiree who struggles to crack open your nest egg, you need to recognize that unspent money loses its entire purpose. You have to learn how to enjoy the wealth you worked so hard to build.

I have immense respect for Jesse’s courage in pivoting his company’s core messaging away from the traditional idea of “budgeting.” He is prioritizing what genuinely helps people over short-term marketing convenience, and it makes for an incredible conversation.

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If you spend enough time in the personal finance space, you’ll eventually bump into a pervasive modern ethos: Die with Zero.

The argument goes that if you die with money left in the bank, you’ve essentially wasted precious life energy working for dollars you never got to enjoy. Lately, I’ve noticed this philosophy creating a profound sense of anxiety and even guilt among early retirees when they realize they’ve accumulated far more money than they could ever realistically spend.

Inspired by my recent post, Escape Velocity, I wanted to dedicate a solo “10 Things” episode to pushing back on this narrative. Let me be clear: There is absolutely no shame in dying a millionaire. In fact, for many of us, it’s the most natural outcome of a well-planned life.

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Here is why you need to let go of the guilt of over-accumulating, broken down into ten things you should keep in mind.

Things 1 & 2: You will likely die a millionaire (and that’s a fantastic outcome)

If you are dedicated enough to your finances to listen to personal finance podcasts or read this newsletter, you are probably going to die a millionaire. Why? Because we are planners. We stack conservative assumption on top of conservative assumption. We model for historically low market returns, historically high inflation, and worst-case scenarios.

When you build a plan designed to survive the apocalypse, you will inevitably overshoot your actual financial needs in normal times. And you know what? Leaving wealth behind for your children or to causes you care about is a beautiful, fantastic outcome. It is not a failure.

Things 3 & 4: Saving money often brings more happiness than spending it

The personal finance world constantly insists that spending money on experiences is the ultimate key to joy. I’m going to push back on that.

While experiences are wonderful, those memories are fleeting and the immediate high fades quickly. Conversely, watching your savings grow provides a deep, structural, and lasting sense of safety. It significantly reduces your daily life anxiety. That underlying peace genuinely increases your baseline happiness in a way that a two-week vacation to Europe simply cannot.

Thing 5: Dying rich does not mean you didn’t spend

There is a massive misconception that if you die with millions, you must have lived a life of deprivation. It ignores the absolute magic of compound interest.

Wealthy retirees often spend far more in retirement than they ever did during their accumulation phase. It’s just that once a portfolio reaches a certain critical mass, its growth simply outpaces their increased lifestyle spending. You can live large and still die rich.

Things 6 & 7: Accumulation is really about “Escape Velocity”

People rarely save massive portfolios just to fund their baseline retirement needs. What we are really saving for is Escape Velocity.

We save to reach a specific, psychological number that gives us the courage to finally walk into our boss’s office and leave a job we dislike. This “escape velocity” number is almost always vastly higher than what the math dictates we actually need to survive. Because we are buying courage, we guarantee that we will drastically overshoot our financial needs.

Thing 8: Give your money away now

Since most diligent savers will overshoot, my advice is to start giving your money away now. Give it to your children in their 20s and 30s when they are trying to buy a house, start a family, or pay off education debt. That is when the money is transformative. Waiting until you pass away, when they are already established in their 60s, misses the window of maximum impact.

Thing 9: Long-term care likely won’t bankrupt you

The bogeyman of retirement planning is the nursing home. We are terrified of end-of-life medical costs wiping us out.

However, the data tells a different story. Roughly 86% of people will spend $100,000 or less out-of-pocket on long-term care. Yes, it’s an expense, but if you have over-accumulated millions, this will not derail your financial legacy or bankrupt your family.

Thing 10: Happy people think about money less

The ultimate benefit of dying with millions isn’t the number on the balance sheet; it is the fact that you get to spend your final decades completely free of financial anxiety. Having excess money means you simply stop worrying about it. You get to focus entirely on purpose, identity, and connections—which is a massive boost to your overall mental health and longevity.

A Word from the Community: Letting Go of the Sunk Cost Fallacy

To wrap up, I want to share a message I received from a listener named Lee.

Lee recently retired early and immediately felt immense anxiety. He realized he had worked too long and saved far too much, leaving him stressed about how he was ever going to “spend it all down” to align with the Die with Zero philosophy. He was trying to force himself to spend money on lavish experiences that weren’t actually bringing him joy.

Lee wisely realized he was suffering from the sunk cost fallacy. Just because you traded years of your life to build a massive pile of money doesn’t mean you are obligated to exhaustively spend it to validate the effort. Lee decided to stop forcing it.

I want to applaud Lee for this realization. I want to remind you all of the same thing: Your “escape velocity” number is never objectively too high or too low. It is simply the exact number you personally needed to feel safe enough to change your life for the better.

If that number leaves you with millions in the bank at the end of your life, take a deep breath, smile, and consider it a job well done.

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In a recent post, I explored the concept of “escape velocity.” In the personal finance space, we often think of this as our accumulation number—the net worth that allows us to safely leave our jobs or retire.

But here is the reality: that number is rarely based on how much we actually need to survive. Instead, our escape velocity is the amount of money it takes to give us the courage to leave work.

Because it takes so much to make us feel secure, that number is almost always much higher than what we actually need to fund our lives. This is exactly why most people who achieve financial independence die with millions left in the bank, and why the “Die with Zero” ethos has become so massive—and paradoxically, so anxiety-provoking—for those who have more money than they know how to spend.

Given this tension, it got me thinking: what does financial freedom really mean?

What Financial Freedom is NOT

To understand what true financial freedom is, we first need to strip away what it isn’t.

• It is not strict Financial Independence: The standard FIRE movement relies on highly conservative assumptions. As a result, our target number is usually way too aggressive, leading us to endlessly over-accumulate just to feel safe.

• It is not “Die with Zero”: The idea of perfectly spending every single cent until your dying day is an interesting thought experiment, but the reality of actively trying to run out of money is deeply stressful for many people. Sometimes, having money sitting in the bank is less stressful than being forced to spend it.

• It is not just buying happiness: Using our money purely to create experiences that we hope will make us happy is a flawed equation. Money does not automatically equal happiness, and forcing yourself to spend it won’t change that.

The Core of Financial Peace

If financial freedom isn’t endless accumulation, perfectly timed spending, or buying happiness, what is it?

Financial freedom is the ability to navigate your life without worrying about money one way or another. It is the freedom to go to a restaurant, take a vacation, or build the life you want without constantly running the math in your head.

It is the profound absence of financial worry.

True financial peace means you aren’t terrified that you aren’t saving enough, but you also aren’t stressed that you aren’t spending enough. Money simply becomes a tool in the background. We use it when it makes our lives better, and we don’t spend much time thinking about it when it’s unnecessary.

It is easy to dismiss this concept as a luxury reserved only for the ultra-wealthy or the highly privileged. But financial indifference does not require infinite resources. You do not need a massive trust fund or an eight-figure net worth to stop worrying about money. Instead, indifference comes from a deep, intentional alignment between what you actually value and how you live. When you clearly define what "enough" means for your specific life, you free yourself from the exhausting treadmill of constant comparison and artificial needs. True peace is found not in having everything, but in holding on. to what serves you and

confidently letting go of the rest.

The Ultimate Goal: Financial Indifference

We have spent far too much time in this community obsessed with the math. Whether it’s the traditional financial independence movement telling you to hoard, or the new wave of thought telling you to spend, both keep your mind entirely focused on your bank account.

We need to free ourselves from that mental trap. What we are really striving for isn’t a specific net worth.

We are striving for financial indifference.

When you reach a state where you simply don’t have to think about the money at all—that is when you are truly free.