We are biologically wired to survive by fighting, fleeing, or freezing. When a predator attacks, these ancient evolutionary reflexes keep us alive. But when the stock market dips or a complex financial decision looms, these exact same instincts actively destroy our wealth. We fight market shifts by clinging to our biases, flee by panic-selling into cash, or completely freeze in paralysis.

This week on the podcast, I sat down with someone who has seen every iteration of financial self-sabotage. Barry Ritholtz is the co-founder and Chief Investment Officer at Ritholtz Wealth Management, where he oversees more than $9.4 billion in assets. He’s also the host of Bloomberg’s Masters in Business and the author of a brilliant new book, How Not to Invest: The Ideas, Numbers, and Behaviors That Destroy Wealth and How to Avoid Them.

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What I love about Barry’s approach is that he doesn’t focus on picking the next unicorn stock or chasing legendary, lottery-ticket wins. Instead, he looks at investing like amateur tennis. You don’t win the match by hitting blistering aces; you win by simply keeping the ball between the lines and waiting for your opponent to hit the net. Long-term wealth is about minimizing unforced errors, recognizing your skill limits, and staying strictly within your performance envelope.

You might think a guy managing billions has a flawless track record, but Barry was incredibly candid with me about his own expensive tuition in the markets. He shared the painful story of buying Apple shares for around 28 cents (split-adjusted) in the early 2000s, only to sell them at $45 to “teach brokers a lesson” about holding assets. He tripled his money, sure—but he missed out on an 8,000% run-up over the next two decades because he made the classic unforced error of behaving like a short-term trader with a long-term investment.

He also introduced a concept I haven’t mastered myself: epistemic trespass. In 2014, venture capitalist Howard Lindzon pitched Barry on a new app for millennials to trade stocks for free. Barry dismissed it as a terrible idea, wrongly assuming his deep expertise as an equity trader made him an expert in venture capital. That app was Robinhood. Lindzon turned his investment into $100 million, while Barry sat on his hands.

During our conversation, we dug deeply into the psychological traps that catch so many of us. We talked about the danger of starting out on the peak of “Mount Stupid”—that precarious Dunning-Kruger intersection of high confidence and low actual skill—before inevitable market losses tumble you into the valley of despair on the slow climb toward wisdom.

We also pulled back the curtain on the financial media machine. As Barry bluntly puts it, financial news is practically reality TV. It relies on sensational graphics, urgent music, and constant drama to keep you anxious and engaged. They aren’t fiduciaries; they exist to sell advertising. It’s why you always have to ask yourself what the person on the screen is actually selling, and why you should only follow experts who display a chill temperament, a repeatable process, and experience across multiple market cycles. (Or, as Barry noted, quoting neurologist Bill Bernstein: we only use the word “guru” because charlatan is too hard to spell).

So, how do we actually protect ourselves from our own worst impulses? We discussed the exact frameworks you need to stop self-sabotaging:

• Why Index Funds beat Stock Picking: Just 1.2% of public stocks have created all the net wealth in the stock market. Because identifying those needles in the haystack in advance is nearly impossible, buying the entire market via broad index funds is the only surefire way to capture those gains.

• Tailoring Your Bonds: We broke down how to stop blindly following rules of thumb. Young investors with a 30-year horizon might skip bonds entirely to maximize equity compounding, while high-net-worth pre-retirees need highly tailored municipal bond portfolios to stabilize income and manage volatility.

• The “Cowboy Account”: If you still have that burning itch to speculate on individual stocks or crypto, Barry shared his favorite behavioral hack. Cap a separate account at 3% to 5% of your liquid net worth, put it at a completely different brokerage, and let yourself play without ever endangering your core wealth.

My biggest takeaway from this conversation goes far beyond the portfolio. It comes down to acting with clear, deliberate intention. Whether we are navigating our relationships, our careers, or our finances, intention is our ultimate shield against unforced errors. When you align your daily decisions with your true, long-term identity rather than fleeting FOMO or fear, you simply stop getting in your own way.

If you want to stop fighting, fleeing, and freezing your way through your financial life, you do not want to miss this conversation.

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In my years as a hospice physician, I’ve sat at hundreds of bedsides watching families navigate the final chapters of life. Beyond the emotional weight of medical illness, there is another tragedy I see play out far too often: the sudden, overwhelming chaos that unfolds when aging intersects with a lack of intergenerational financial planning.

We spend decades optimizing our 401(k)s, tweaking asset allocations, and tracking net worth on spreadsheets to guarantee our own financial independence. Yet, sitting right in the middle of almost every FIRE plan is a silent, unexamined variable: our aging parents.

For this week’s Earn & Invest Rewind—a foundational episode recorded back when the show was called What’s Up Next—my co-host Paul Thompson and I brought together a panel of experts to confront a question most people avoid until it’s too late: Will your parents complicate your financial future?

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When Theory Meets Unfiltered Reality

What makes this episode so essential isn’t just the statistics—it’s the raw, first-hand stories shared by our panel:

• Doug Nordman (The Military Guide): Doug spent over six years managing his father’s finances after his dad developed Alzheimer’s without a Power of Attorney in place. Because no disability planning had been completed, Doug was forced into a grueling court-ordered conservatorship costing over $14,000 in legal fees—all while managing care facility bills reaching $8,000 a month.

• Jen Smith (Co-host of Frugal Friends): Jen shared the shocking discovery in 2017 that her mother had secretly defaulted on her refinanced mortgage for nine years following her father’s death, resulting in a sudden foreclosure notice that rocked the family.

• Cameron Huddleston (Author of Mom and Dad, We Need to Talk): Cameron navigated assisted living costs ranging from $4,500 to $6,000 per month after her mother was diagnosed with Alzheimer’s at just 65 years old—forcing her to balance heavy caregiving demands while raising her own young children.

• Steve Chen (Founder of Boldin / NewRetirement): Steve revealed how helping his own mother navigate financial turbulence and credit card debt near her retirement was the very catalyst that led him to create retirement planning software.

The Hidden Costs of Caregiving

The numbers surrounding elder care in America are staggering, and they directly threaten the financial security of the “sandwich generation”—those supporting both aging parents and growing children:

• The Out-of-Pocket Drain: Over 40 million Americans act as family caregivers, with 68% contributing an average of $7,000 annually out of their own pockets.

• The Lifetime Cost: A MetLife study estimates that the total financial hit to working caregivers—when factoring in lost wages, reduced Social Security, and missed pension contributions—ranges between $280,000 and $320,000.

• The Long-Term Care Myth: More than half of adults over 65 will require long-term care (averaging three years), yet Medicare does not cover non-skilled long-term care.

Where Do We Go From Here?

Navigating this crisis isn’t about stripping away your parents’ autonomy; it’s about mutual protection and dignity. In the episode, we break down actionable steps you can take today:

1. Start Early & Frame with Empathy: Talk to your parents while they are still young and healthy. Frame discussions around love, respect, and peace of mind—or initiate the conversation by sharing your own estate planning steps first.

2. Secure Essential Legal Documents: Ensure your parents execute a General Durable Power of Attorney (POA) and an Advanced Healthcare Directive while mentally competent. This single step prevents nightmare conservatorship court battles down the road.

3. Prioritize Your Own Hierarchy: As difficult as it sounds, your personal retirement savings must take priority over funding children’s college or parents’ care—unless supporting parents was explicitly built into your long-term budget from day one.

4. Enlist Local Experts: Consider hiring a Geriatric Care Manager. These professionals understand local community resources, facility inspection records, and complex Medicare/Medicaid qualification rules that can save families tens of thousands of dollars.

5. Break the Cycle: Use these lessons to ensure your own adult children never have to play detective with your finances during a crisis.

Listen to the Episode

Whether you are currently in the thick of elder care, anticipating it in the coming decade, or trying to protect your own children from future burden, this conversation offers a compassionate, pragmatic roadmap.

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How have you navigated financial conversations with your aging parents? What boundaries or systems have worked for your family? Reply to this post or jump into the comments—I’d love to hear your story.

Wealth and achievements are often viewed as purpose and yet, they won’t fulfill you. In fact, they will most likely trap you. We often operate under the backward assumption that we can use purpose to finally feel fulfilled, but purpose is actually something you engage in only after you are fulfilled. After you feel enough.

We constantly try to prove our worthiness through a net worth number, the concept of financial independence, or by reaching a specific goal. The problem is that if you feel unsettled, lack fulfillment, or are unhappy in the first place, making a certain amount of money or hitting an achievement will not make you happy. This approach fails because of hedonic adaptation. Whether we are spending money for a quick burst of joy or chasing a milestone for a fleeting hit of satisfaction, the result is the same: we immediately trap ourselves on an endless treadmill. Ultimately, you cannot fill an internal void with external wealth and accolades. No matter how hard you run.

That feeling of not being enough does not come from a lack of achievement; it usually stems from your past and your trauma. You must come to terms with your own enoughness and deal with being unfulfilled first. Once you do that, you can jump joyfully into your purpose, knowing that purpose was never meant to prove your worthiness.

When we look through this lens, we start to truly understand hustle culture. People hustle and achieve more and more because they believe it will fill their emptiness, justify their existence, and bring fulfillment. It often doesn’t. We reach one plateau, feel good briefly, and then adaptation kicks in, forcing us to look toward an even higher, more difficult peak. If you get caught up in endless side hustles to make more money, you will face one of two outcomes. You will either succeed and realize you still aren’t fulfilled, or you will never reach your goal and end up burning out, feeling down and like a failure.

I suggest we let go of hustle culture entirely. We should replace it with the concept of persistence culture. Persistence culture is about doing things you actually enjoy the process of doing, regardless of whether you hit the ultimate goal or not. It requires you to be more goal agnostic. You can still work hard, but if you are not enjoying the day-to-day process, you will likely burn out and quit. Conversely, when you embrace persistence culture and do what you enjoy, you can do it forever.

Fulfillment comes before purpose. And purpose, through the lens of persistence, is simply doing the things you love to do.

The Happiness Code Pre-Sale Raffle My next book, The Happiness Code, officially drops on March 9, 2027. If you pre-order your copy now and email me the receipt (docg@diversefi.com), you’ll be entered into a raffle to win 50 copies (a $1,000 value) to donate or gift to your favorite organization, library, or community group.

We spend our entire adult lives dreaming of the day the financial tension finally disappears. We imagine that crossing the ultimate wealth finish line will automatically unlock a state of permanent bliss.

Jeremy Schneider thought the same thing. As the founder of the tech startup Rent Links, Jeremy paid himself a modest $36,000 a year, purposely making himself the lowest-paid employee in his own company so he could pay his team well and keep the business growing. His frugality and business building paid off. He sold the high-growth company for $5 million, handed out massive five- and six-figure payout checks to his employees, and walked away with a $2 million post-tax share.

By age 36, with a net worth of $3 million, he was fully retired. He had won the game.

His reward was an intense existential crisis. After spending a year traveling and playing video games, Jeremy realized that solving his money problem hadn’t solved his human problem. A life entirely devoid of tension and meaningful pursuits left him feeling completely unfulfilled.

He uninstalled his video games cold turkey and went back to the drawing board to find a new identity. What started as informal financial coaching over beers with friends eventually became Personal Finance Club, a massive educational platform built on pure content integrity, completely free from the survival-driven stress and corporate funding of his previous startup.

In this week’s podcast rewind, Jeremy and I sit down to dismantle the complex, panic-driven way pop culture portrays investing. We get into the actual mechanics of building wealth, starting with his two famously simple rules: live below your means, and invest early and often.

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We cover a lot of ground in this conversation, including:

• The 90/10 Index Fund Rule, and why 10% of your portfolio can be used as a speculative “safety valve” to cure your FOMO.

• Why you must keep insurance and investing completely separate (and why you should run from salesmen pushing high-commission whole life policies).

• The truth about estate taxes, and why 99% of people are wasting their time agonizing over complex tax-optimization schemes for their heirs instead of letting their kids make their own way in the world.

• Why getting past your fear of investing is as simple as opening a Vanguard or Fidelity account and clicking a button with just $50.

If you’ve ever felt paralyzed by the sheer complexity of the financial industry, or if you’re wondering what actually happens in your brain after you hit your magical FIRE number, this conversation is required listening.

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What is the very first thing you would do if you woke up tomorrow and the financial tension in your life was permanently gone?

One quick community update before I go:

1. The Happiness Code Pre-Sale Raffle My next book, The Happiness Code, officially drops on March 9, 2027. If you pre-order your copy now and email me the receipt (docg@diversefi.com), you’ll be entered into a raffle to win 50 copies (a $1,000 value) to donate or gift to your favorite organization, library, or community group.\

We spend a tremendous amount of time building a financial framework where wealth is the ultimate finish line. We calculate our net worth, track our investments, and aim for a magic number that promises freedom. But what happens when you finally arrive? Often, it’s a profound feeling of being lost, wondering what comes next.

After a recent podcast conversation with Kristy Talorico about human resources, I started reflecting deeply on my own financial self-care. I am not talking about how others care for us, but the internal mindset we use to govern our own money. On this week’s episode, I lay out ten essential practices that have helped me reframe my financial life.

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Here is a glimpse into how I practice financial self-care:

Remember that money is just a tool. The real outcomes we are shooting for are time freedom, deep connections, and the ability to pursue our hobbies. If your money isn’t actively helping you build that life, you need to rely on other tools like your intelligence and friendships.

Forgive your past indiscretions. I have bought life insurance policies I had no business buying and chased stocks high only to sell low. Every highly successful investor makes mistakes; the key is to forgive yourself, rebound, and move forward rather than dwelling on the loss.

Put your blinders on. You are running your own personal race. When you look left and right at the crypto windfalls or massive business successes of others, you risk veering completely out of your lane.

Reframe your enoughness. This might be the most critical step. You have to separate your internal self-worth from your external net worth metrics. You are already enough, exactly as you are, freeing you from the endless chase.

In the full episode, we dive much deeper into the mechanics of financial self-care—including how to intentionally size your speculative risks, why generously giving your money away moves the needle on happiness, and how to truly understand your financial baseline before hiring advisors. Listen to the complete breakdown on the Earn & Invest podcast.

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If you are local to Chicago, I would love to talk about these concepts with you in person. The Wealth with Purpose Mastermind is hosting a meetup this Saturday, October 3rd, at 7 PM at the Duke of Perth (2827 N Broadway).

Also, my upcoming book, The Happiness Code, is available for pre-order. Email your receipt to docg@diversifi.com to enter a raffle to win 50 copies to give away to your friends, family, or favorite organization.

There is a quiet, pervasive anxiety humming beneath the surface of the personal finance community. We are perpetually stressed about spending money. Some of us are terrified we are spending too much, while others worry we aren’t spending enough. Both extremes are problematic.

The root of this anxiety is simple. We spend far too much time obsessing over the actual sum in our bank accounts and not nearly enough time thinking about what that money is actually doing for us.

When we shift our focus from the math to the meaning, spending falls into four distinct categories. The first three are straightforward, but the fourth is the secret to a well-lived life.

First, there is necessity. We have to keep the lights on. This is the money we allocate for shelter, heat, and food. It also includes the basic requirements of modern life, like your smartphone or your watch. These are the absolute non-negotiables.

Second, there is generosity. When we find ourselves with a surplus, giving back is one of the most reliable ways to generate joy. Whether it means supporting family and friends or donating to a philanthropic cause, generosity makes us feel good. It is deeply connected to our happiness.

Third, there is frivolity. Frivolity gets a bad reputation, but it shouldn’t. This is the money spent on things that make life immediately more enjoyable. It is the upgraded house, the beautiful meal at a nice restaurant, or the random impulse buy that brings a smile to your face. The catch with frivolity is that its benefits are fleeting. It makes us happier in the short term, but it rarely moves the needle on our long-term fulfillment.

Then we arrive at the fourth category. This is the one that matters most.

We should be spending the bulk of our extra money on identity.

Identity is who we are. It is also who we hope to be when we are living as our best, most authentic selves. When you have a clear sense of your identity, it naturally gives birth to a set of intentions. Those intentions then drive your actions in the real world. This process of taking action is what I call your “little p” purpose. It is the act of bringing your internal identity to life, and it is the most reliable path to genuine happiness.

Let me give you an example.

Part of my identity is being a writer. My intention is to create works that resonate with people and affect their lives. The actions I take to support this are writing books, publishing blog posts, and recording podcasts.

So, where does the money come in?

Spending on identity means directing your resources to support those exact actions. For a writer, that might mean hiring a writing coach. It might mean paying for classes, enrolling in an MFA program, self-publishing a project, or buying a ticket to a writing conference. You are using your capital to fund your intentions.

When you look at your finances through this lens, the old debates start to lose their edge.

It really does not matter if you subscribe to the philosophy of dying with zero. It also does not matter if you die with millions of dollars sitting in the bank. The final math is just a distraction. What actually matters is how you spent those resources along the way.

If you want to spend correctly, you need to hit all four categories. You spend on necessity to survive. You spend on generosity and frivolity to feel good in the moment. Most importantly, you spend on identity to become the best version of yourself.

If you can do that, you are moving closer to true happiness. You are finally using your money to support a better life. At the end of the day, it does not matter how much you spend. It only matters how you spend it.

Two quick community updates before I go:

1. Chicago Meetup! I’m hosting an in-person Earn & Invest meetup on Saturday, October 3rd at 7:00 p.m. We’ll be hanging out at the Duke of Perth (2827 N. Broadway St., Chicago). I’d love to see you there to talk money, purpose, and everything in between.

2. The Happiness Code Pre-Sale Raffle My next book, The Happiness Code, officially drops on March 9, 2027. If you pre-order your copy now and email me the receipt (docg@diversefi.com), you’ll be entered into a raffle to win 50 copies (a $1,000 value) to donate or gift to your favorite organization, library, or community group.

See you in Chicago,

Did you know chronic financial strain is as damaging to your heart as smoking?

A Mayo Clinic study of 280,000 adults showed that the perpetually raised cortisol levels from money stress actually cause premature cardiovascular aging. As a doctor, that stops me in my tracks.

But when an employee is stressed about money, what does traditional HR offer? Usually, a 401(k) match and a referral to a retirement coach. That’s great if you have the luxury of planning 30 years out. It’s completely useless if you’re among the 70% of Americans living paycheck-to-paycheck, or the 53% with less than $500 in emergency savings. Traditional HR departments usually act as “finances light,” pointing people toward administrators who often have competing interests rather than focusing on the employee’s immediate, holistic well-being.

This massive disconnect is exactly what we tackle on the newest episode of Earn & Invest.

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I sat down with Kristy Talorico. She used to lead enterprise sales at Apple and Microsoft, but today she’s on the team at Brightside—a platform fundamentally changing how employers handle financial care.

During our conversation, Kristy breaks down the staggering hidden cost of financial distress. Employers are bleeding $3,000 to $4,000 a year per employee through absenteeism, sick days, safety incidents, and unwanted turnover.

Instead of slapping a band-aid on the problem, Brightside actually treats the root cause. Rather than hiring traditional finance bros, they recruit Financial Assistants (FAs) with backgrounds in social work, therapy, nursing, and teaching—people actually trained to motivate behavioral change. They don’t make commissions, so there’s zero conflict of interest.

Kristy shared an incredible story on the show about a healthcare worker named “Daisy.” Daisy had just escaped an abusive relationship, was homeless, and asked for an $1,800 loan to secure an apartment. A traditional system would have just issued the debt or turned her away. Instead, her FA secured emergency shelter and food, enrolled her in free EAP therapy, found an overlooked $1,800 non-repayable grant from her employer’s hardship fund, and put her on a debt management plan that saved her over $38,000 in interest and fees.

They also use AI to instantly match employees with hidden, underutilized benefits—like legal care, estate planning, and backup childcare—connecting people to these lifelines at the exact moment they need them.

Even if you’re already financially independent, this episode is a must-listen. We all have family members, friends, or employees who are quietly struggling. Understanding what real financial care looks like equips us to actually help them.

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Two quick community updates before I go:

1. Chicago Meetup! I’m hosting an in-person Earn & Invest meetup on Saturday, October 3rd at 7:00 p.m. We’ll be hanging out at the Duke of Perth (2827 N. Broadway St., Chicago). I’d love to see you there to talk money, purpose, and everything in between.

2. The Happiness Code Pre-Sale Raffle My next book, The Happiness Code, officially drops on March 9, 2027. If you pre-order your copy now and email me the receipt (docg@diversefi.com), you’ll be entered into a raffle to win 50 copies (a $1,000 value) to donate or gift to your favorite organization, library, or community group.

See you in Chicago,

Doc G

Have you ever hit a massive financial or career milestone, only to wake up the next morning feeling exactly the same?

If you’ve spent your life on the achievement treadmill, believing that reaching a certain net worth, job title, or download number will finally make you feel “enough,” you’ve probably encountered the Achiever’s Paradox. I certainly did. We tell ourselves that once we arrive at our goal, everything will feel good. But the satisfaction is fleeting.

I’ve spent the last few years unpacking why high achievers struggle to find lasting joy, and the result is my upcoming book, The Happiness Code, officially releasing on March 9, 2027.

To give you a sneak peek, I just dropped a special solo “10 Things” episode on the Earn & Invest podcast. In it, I break down the ten core concepts from the book on how to cultivate true happiness, meaning, and fulfillment.

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Here is a quick breakdown of what you’ll discover in the episode:

1. You can’t purpose your way to happiness. Happiness requires two distinct components: meaning (how we process and integrate our past) and purpose (our present and future actions). You cannot use future accomplishments to fill an emptiness caused by unresolved past trauma.

2. The Arrival Fallacy. Hitting arbitrary goals provides only a short dopamine hit due to hedonic adaptation. Believing the next milestone will fix everything is a trap.

3. Spend on “becoming,” rather than things. Emotional well-being plateaus around $100,000 annually. Instead of buying material goods for a quick rush, spend your money on activities and growth that align with your desired identity.

4. Become a “Rosebud Detective.” Inspired by Citizen Kane, your “rosebud” is a core childhood trauma or event that split your life into “before” and “after.” You must interrogate your inner demons using tools like the “Three Whys and a When” technique to trace bad feelings back to their root.

5. Persistence culture beats hustle culture. Hustle culture relies on extreme, burnout-inducing effort to prove self-worth. Persistence culture focuses on the sustainable daily enjoyment of doing things you actually love.

6. You can rewrite your neurons. Repeating negative stories (”I’m bad at math”) hardwires those neural pathways. Through conscious awareness and visualization, you can leverage neuroplasticity to build a new inner narrative.

7. Cognitive grounding vs. sensory grounding. Sensory grounding connects you to nature, but cognitive grounding places you in environments or routines that reconnect you to the heroic parts of your identity—like how I feel working in a hospital cafeteria or listening to classical music by Lake Michigan.

8. The real cure for burnout. You can’t cure burnout with a vacation. You cure it by stepping off the achievement treadmill, resolving your rosebud, and shifting from obsessive “Big P” purpose to finding joy in “Little P” daily processes.

9. Decouple money from happiness. Many in the FI community just trade “saving anxiety” for “spending anxiety.” True happiness relies on meaning, not portfolio size. There is no shame in dying with money.

10. Unlocking the people around you. Once you understand your own rosebud, you start recognizing the underlying traumas driving your spouse, kids, and colleagues. It makes you a radically more empathetic partner, parent, and leader.

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The Pre-Sale Book Raffle

The Happiness Code drops March 9, 2027, but pre-orders matter immensely in the publishing world. To say thank you to this community, I’m hosting a massive giveaway.

If you pre-order a copy of the book from any retailer before October 15th, you will be entered into a raffle to win 50 copies ($1,000 value) of the book to donate to your favorite conference, organization, or group of friends. I may even throw in some early digital access for the winner.

Here is how to enter:

1. Pre-order The Happiness Code here

   Pre-order The Happiness Code

2. Email a screenshot or forward your receipt to docg@diversefi.com before October 15th to enter the raffle.

I can’t wait to share this work with you. Tune into the podcast this week, grab your pre-order, and let’s start decoding what actually makes us happy.

I’ve been working on my fitness lately, and it taught me a surprising lesson about money.

For the last 12 weeks, I committed to lifting weights. I’ve been a cardio guy for a lifetime, but it’s been a good thirty years since I seriously lifted. Knowing that I’m in my fifties and need muscle mass for stability and a longer healthspan, I decided to go all in. I started aggressively lifting six days a week, progressively overloading my muscle groups exactly the way the YouTube fitness gurus recommend.

At first, it felt great. My muscles were getting bigger and I was getting visibly stronger.

But about six weeks in, the wheels started coming off. I developed a new injury every single week. First it was my shoulder. Then my back. Then my pecs. My joints throbbed constantly. On top of the physical pain, I was completely exhausted, to the point where I was spontaneously falling asleep at six or seven o’clock at night—something I had never done before.

I was hobbling through my days feeling significantly worse than before I started.

I realized my approach was completely unsustainable. The goal of lifting was to feel good and improve my health, but I was making myself miserable. So, I changed the routine. I cut back from six days a week to every other day. I switched to full-body workouts just three or four days a week.

The result? The injuries healed. The constant aching stopped. I felt stronger than ever, and my body actually continued to change the way I wanted it to. I was simply overtraining, and taking my foot off the gas was the cure.

It hit me a few weeks ago: we do the exact same thing with our money.

We go completely down the personal finance rabbit hole. We use frugality as a weapon. We track every single cent we spend. We obsess over our investments, constantly maximizing the tax code, and agonizing over the minor differences between traditional and Roth accounts. We become so hyper-focused on the efficiency of our financial machine that we forget why we built it in the first place.

You’ve probably seen the symptoms. It’s the person who makes a great living but feels acute stress over buying a cup of coffee. Or the millionaire who checks their portfolio balance three times a day, terrified that they haven’t optimized their safe withdrawal rate.

I know people who are totally on top of their money, worth millions of dollars, yet they are visibly stressed all the time. They are financially secure, highly optimized, and entirely unhappy.

Financial overtraining happens when we get so deep in the woods that the process itself becomes a source of pain. We get so efficient with all the tips and tricks that, instead of getting the results we actually want—peace of mind, freedom, security—we just feel worse. We become penny-wise and pound-foolish with our own well-being.

Most of our financial journeys follow a similar arc to my fitness journey. In the beginning, we need to do the heavy lifting. We need to put the spreadsheets together, learn to save, and build the foundation.

But eventually, you have to accept good and “good enough” over perfect.

If your financial plan is causing you daily anxiety, you might not be failing because you lack discipline. You might be overtraining. The solution is to take a step back. Take some time off from checking your balances. Put the spreadsheets down. Let your compounding do the work, and give yourself permission to actually enjoy the life you’ve been saving for.

Pre-orders now Available

There is a terrifying concept in financial history known as Ferguson’s Law.

Coined by the brilliant financial historian Niall Ferguson, the law is brutally simple. It states that an empire reaches a critical, irreversible inflection point of decline the exact moment it spends more money servicing the interest on its national debt than it spends on its own national defense. It is the ultimate tipping point. It is the moment the bill truly comes due.

Depending on how you measure the math, the United States of America is currently in violation of Ferguson’s Law.

This staggering reality is exactly how we kick off the newest episode of the Earn & Invest podcast. I sat down with Robin Wigglesworth, the editor of FT Alphaville and the author of the incredible new book A Fabulous Debt: The Epic Story of How Bonds Built the Modern World.

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I know what you are thinking. Bonds. They are boring, right? They are the sleepy, passive safe assets we stuff into the 20% of our 80/20 portfolios just to make sure we don’t lose our shirts when the stock market throws a tantrum.

Robin completely shattered that illusion for me.

He describes the bond market not as a sleepy safe haven, but as the absolute “dark matter of finance.” It is the invisible, massive foundation that secretly ties the entire global financial system together. It is significantly larger—and vastly more powerful—than the stock market and the banking system combined.

The history of this dark matter is absolutely wild.

It all started in 12th-century Venice. The original bond, known as the Prestiti, wasn’t an investment tool at all—it was a forced tax to fund a war. But when Venice lost the war and couldn’t pay its citizens back, they made the interest-bearing receipts tradable at the Rialto market. That pure, accidental innovation birthed the world’s first liquid bond market.

From there, debt literally built the modern world. The Dutch built a wildly successful bond market because of a strict cultural ethic to always pay their debts—so much so that some of those ancient 400-year-old Dutch bonds are still paying interest today. Great Britain leveraged its massive console bond market to out-fund its rivals during the Napoleonic Wars. When the wars ended, the ensuing bond rally provided the massive influx of wealth that single-handedly capitalized the Industrial Revolution. Even Alexander Hamilton took frantic notes, realizing the U.S. desperately needed to copy British finance if it wanted to survive.

But with massive power comes massive, systemic risk.

We completely forget that the 2008 financial crisis was not a stock market crash. It was fundamentally a bond market crash. Financial engineers in the 70s and 80s figured out how to package individual mortgages, student loans, and credit card debt into tradable bonds through securitization. When the underlying due diligence on those securitized mortgages completely failed, the entire global banking system keeled over.

And when traditional interest rate cuts failed to stop the bleeding in 2008—and again during the 2020 pandemic—central banks turned to Quantitative Easing. QE is nothing more than massive, unprecedented bond buying by the Federal Reserve to inject liquidity into a dying system. It created wild financial excesses, yes, but Robin argues it successfully prevented a total global economic collapse.

Human nature never changes. We continuously invent complex, highly leveraged debt products. We take excessive, ridiculous risks until the entire system shatters. We learn our lesson, exercise temporary caution, and then repeat the exact same cycle a generation later.

Bonds aren’t boring. They are the terrifying, magnificent engine of the world.

You absolutely have to listen to this conversation with Robin. It will completely change how you view your portfolio, global politics, and the money sitting in your bank account right now.

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A Quick Note for My Chicago People

Before you go, I want to invite you to hang out with me in person! On Saturday, October 3rd at 7:00 p.m., we are hosting an informal Earn & Invest meetup and mastermind gathering at The Duke of Perth right here in Chicago. Come grab some incredible fish and chips, have a pint, and let’s build some real community. I would love to see you there.

Early in my investing journey, I took some very common financial advice to heart: “Invest in what you know.”

At the time, my grandmother was living at a Sunrise Assisted Living facility. I visited her often and was absolutely blown away by the care she received. The staff was incredible, the facility was top-notch, and the business seemed booming. It felt like a sure thing. So, I proudly bought $1,000 worth of Sunrise stock.

Fast forward over two decades. That stock had barely moved, and once you account for inflation, I actually lost money.

It was a tough lesson, but an important one: Just because you like a company—or even if they provide world-class service—doesn’t mean you understand their financial fundamentals or market position.

On the heels of my recent conversation with Alex Edmans about market inefficiencies, I decided to record a solo “10 Things” episode of the Earn & Invest podcast. In it, I break down exactly why I choose boring, broad-based index funds over picking individual stocks—even when chasing “alpha” sounds incredibly tempting.

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Here is a quick look at why I’ve permanently hung up my stock-picking hat:

1. “Invest in what you know” is a trap. My Sunrise Assisted Living experience taught me that loving a product doesn’t give you an informational edge in the market.

2. Good companies don’t always win. A business can have happy customers and great service, yet its stock can still stagnate or collapse (remember Sears, Enron, or Arthur Andersen?).

3. A few big winners drive the entire market. The S&P 500’s annual returns are usually carried by a tiny handful of top-performing stocks. If you pick stocks and miss just one of those key drivers, you underperform. Index funds guarantee I own the winners.

4. I don’t want to study balance sheets. Tracking CEOs and analyzing trends takes massive amounts of time. I’d rather spend my time writing, podcasting, and being with my wife.

5. I concentrate risk elsewhere. We build wealth through concentration (in our careers, our W-2 jobs, or our businesses) and we preserve it through diversification. Stock picking flips this model, concentrating risk in a place meant for wealth preservation.

6. The Dunning-Kruger effect is real. It’s easy to get lucky early on and think stock picking is easy. That overconfidence almost always leads to long-term underperformance.

7. Money is a tool, not the goal. I refuse to spend all day thinking about money. Obsessively checking tickers in retirement creates anxiety and steals time away from purpose and relationships.

8. Perfect is the enemy of good enough. Capturing the market average (“beta”) through index funds has historically delivered strong returns that easily beat inflation. Chasing “alpha” adds massive risk for a minimal potential reward.

9. I hate volatility stress. Broad index funds lower my anxiety. I don’t have to watch daily market swings because I know I own a slice of the entire global economy.

10. I am not a power hitter. Stock picking requires hitting home runs to consistently beat the market. I prefer hitting a steady stream of singles and doubles—accumulating wealth reliably without the risk of striking out.

The 80/20 Rule of FIRE

At the end of this episode, I also dive into an awesome email from a listener named Gareth. He proposed a fascinating framework: viewing “FU Money” (having roughly 5 years of living expenses saved) as the 80/20 rule of the FIRE movement.

Essentially, you get 80% of the freedom benefits of financial independence for only 20% of the effort and cost.

Historically, I haven’t focused much on the concept of FU money, mostly because I believe we should start living purposeful lives immediately, regardless of our net worth. But Gareth’s framing really got me thinking, and I’m hoping to bring the godfather of FU money himself, JL Collins, on the show soon to discuss it.

Want to hear the full breakdown of my index fund philosophy and the FU money debate?

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We are terrible at spending money. We really are.

Even those of us who are hyper-accumulators—maybe especially those of us who are hyper-accumulators—struggle with this miserably. We accumulated wealth because we were incredibly frugal. We earned, we invested, and it served us perfectly. But eventually, we hit a net worth where our earnings compound, giving us the ability to spend a heck of a lot more than we do... and yet, we still struggle to pull the trigger.

The Time vs. Money Trap

It all relates back to our changing relationship between time and money. When we are young (say, 20 years old) money is infinitely more precious than time.

Would you give up a year or two of your life to make a million bucks at 20? Absolutely! Would you work 60, 70, even 80 hours a week? Yes, you would. You have decades ahead of you. You are energetic, probably not married, no kids, and no mortgage. It is completely necessary and required that you trade your time, an resource you have in abundance, for money, an asset you desperately lack.

But as we get older, and as we develop wealth and skills, the entire equation flips. Suddenly, time becomes infinitely more precious than money.

Enter The Warren Buffett Spending Test

If you doubt that time is your most precious asset, I want you to perform what I call the Warren Buffett Spending Test. Ask yourself this: How much money would Warren Buffett—a guy in his 90s with unimaginable, astronomical wealth—spend to be you right now?

If we are talking about me, a guy who is 53 years old, how much of his wealth would he give up to be 53 again?

The answer is obvious: most likely all of it. He would give away every single penny of his billions.

Are You Failing the Test?

As we get older, money becomes less important, and time becomes absolutely everything. Yet, some fail this test every single day in their own lives.

• The One More Year Syndrome: If you have enough money to retire and you hate your job, but you stick around for just “one more year” because you want a slightly higher net worth, you are failing the Warren Buffett Spending Test.

• The DIY Trap: If you have the wealth to hire someone to clean your house, mow your lawn, or do the chores you absolutely loathe doing, but you refuse to pay for the luxury out of sheer stubbornness, you are failing the test.

Most people reading this Substack or listening to the Earn & Invest podcast are hyper-accumulators. For us, this isn’t a savings problem. It is a spending problem.

How are you going to spend your money to maximize your most precious asset, your time, which is going to pass no matter what you do? Perform the test. Realize that Warren Buffett would trade everything to have your time, and maybe, just maybe, you should spend a few hundred bucks to have someone else clean your house.

What is one task you absolutely hate doing that you could afford to outsource this week? Are you trapped in the “one more year” syndrome?

Pre-orders now Available

Of course you can beat the market.

At least, that’s what the finance industry wants you to believe. For years, we’ve been told that financial markets are perfectly efficient machines, rationally pricing in every piece of news the second it hits the wire. But what if that’s completely wrong? What if the market is actually just as emotional, irrational, and biased as we are?

On the latest episode of the Earn & Invest podcast, I sat down with Alex Edmans, a finance professor at London Business School and author of The Madness of Markets: Why Smart Investors Make Crazy Decisions and How to Exploit Them.

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I went in expecting a standard academic defense of the efficient market hypothesis. Instead, Alex completely dismantled it.

Here are a few of the fascinating—and frankly, wild—things we discussed on the show:

1. The Market is Deeply Emotional

If markets were perfectly rational, stock prices would only move based on fundamentals. But Alex’s research shows something entirely different. For instance, when a country gets knocked out of the World Cup, its national stock market systematically declines the very next day. Why? Because investors are in a bad mood.

Similarly, it turns out the market dramatically underreacts to positive fundamentals. When a company is named to Fortune’s “100 Best Companies to Work For,” it takes four to five years for the stock price to fully reflect the financial value of having satisfied employees.

2. Corporate “Poker Tells”

This was my favorite part of the interview. Just like a poker player with a bad hand, nervous executives give off behavioral tells.

Alex explained how some CEOs deliberately schedule their Annual General Meetings in incredibly inconvenient locations—think McAllen, Texas, or Lahore, Pakistan—specifically to avoid aggressive questions from shareholders. The data backs it up: a strategy of shorting or selling companies after they announce these abnormal meeting locations generated 6% to 12% excess returns over six months.

3. The Dunning-Kruger Trap

It is tempting to hear about these inefficiencies and think, “Great, I’m going to go pick stocks and make a fortune.”

But Alex warns against the Dunning-Kruger effect. Smart professionals often fall into the trap of overconfidence. Unless you have deep, day-to-day access to corporate supply chains and executive management, you don’t have an informational edge. You just have a narrative. And buying a great company with a great story (like AI or electric vehicles) at an inflated price still makes for a terrible investment.

4. How to Actually Exploit the Madness

During the episode, Alex breaks down five specific levels of how investors can apply this knowledge, depending on their actual skill and time commitment:

• Level 1 (Index Funds): Acknowledge you lack a stock-picking edge, ignore the crypto/NFT hype, and buy the whole market.

• Level 2 (Equity Premium): Exploit the historical outperformance of stocks over bonds by simply holding a higher equity allocation.

• Level 3 (Factor ETFs): Use low-cost rules-based funds (like momentum or dividend ETFs) to capture behavioral trends without having to pick individual winners.

• Level 4 (Active Management): Entrust your capital to highly skilled, research-driven managers.

• Level 5 (Stock Picking): Doing the heavy lifting yourself—a path Alex admits he rarely takes himself because of the immense time required.

My Takeaway: Beta is Good Enough

Talking to Alex was incredibly eye-opening, but as I reflected on the episode, I came back to a core philosophy we talk about all the time on Earn & Invest.

Just because market inefficiencies exist, doesn’t mean you have to be the one to exploit them.

For the everyday investor, your primary edge isn’t inside information—it’s your time horizon. Professional fund managers get forced to sell off great long-term investments because their clients panic and withdraw cash during downturns. As an individual investing your own permanent capital, you can simply ride out the storm.

We build wealth through concentration—pouring our time and energy into our W-2 jobs, our careers, or building a business. But we safeguard that wealth through diversification—putting our money into broad, boring index funds.

Unless investing is your primary profession, spending hours trying to squeeze out a few extra percentage points of “alpha” usually just adds unnecessary risk and stress to your life. For the vast majority of us, market beta is more than good enough.

Want to hear the full conversation about corporate poker tells and market madness?

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Let me know what you think in the comments—are you trying to beat the market, or are you happy riding the wave?

I’ve noticed a shift over the last few years. We work on our screens, we socialize on Zoom, and we watch our kids retreat to their bedrooms to scroll YouTube. It’s efficient, sure, but it is incredibly isolating.

A few days ago, I sat down with Mark Trautman at CampFI Midwest 2026, and the energy in that room was a literal jolt to the system. It reminded me of something crucial about the financial independence movement: you can’t spreadsheet your way to courage.

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The Danger of Isolation

For Mark, returning to this specific CampFI was deeply sentimental. Back in 2021, he showed up shortly after his wife passed away. He had been financially independent for six years, but without her, he felt completely lost. As a former hospice doctor, I know exactly how dangerous that moment of grief is—the instinct is almost always to shut down, hide, and isolate.

Instead, Mark leaned into this community. It kept him from retreating into the dark. Twenty CampFIs later, he hasn’t just survived his grief; he’s built a vibrant network of lifelong friends.

From Knowledge to Courage

We talk a lot on Earn & Invest about the math of FI. You can read Jim Dahle, you can scour Mr. Money Mustache’s forums, and you can map out your whole life on a Reddit thread. That gives you knowledge.

But making the leap? Quitting the job, changing your life, or actually spending the money you saved? That takes courage. Being in a room with people who actually get it is like running a marathon and finally hearing the crowd roar during those brutal last miles. That in-person encouragement is usually the exact push you need to take the leap.

In this live collaborative episode, you’re going to hear exactly what that courage looks like in practice. We sat down with some incredible people:

• Amber Smith: A 29-year-old repeat attendee who completely transformed her life. Five years ago, she was a burnt-out corporate worker. Today, she is a self-employed influencer who bumped her net worth from under $100k to $450k. She’s hit Coast FI and credits this community for genuinely pushing her to succeed.

• Ryan B: A first-timer who literally reached the end of the r/personalfinance flowchart and thought, “Now what?” He joked that he came with a zombie-apocalypse exit plan just in case we were a cult performing ritual sacrifices. What he actually found was an openhearted space to figure out his next steps.

The After-Show

Make sure you stick around for the after-show. We opened the mics to the room, and the stories were amazing. You’ll hear from introverts who finally found a group that doesn’t drain their energy, a single mom who met real-life travel hackers, and friends whose parents are still convinced we are a cult buying timeshares.

If you have the math figured out but are terrified to take the next step, this episode is for you. Hit play on your favorite podcast app, and come join the room.

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There are basically two things in my life I’ve been good at: practicing medicine and talking about personal finance. Interestingly enough, I’ve found that the exact same philosophy governs both.

It comes down to the 80/20 rule. Or, as I like to frame it: Simplicity always trumps the last 20%.

The Medical Optimization Trap

For the first two decades of my career as a general internist, and now in hospice and palliative care, I’ve watched the health and wellness space become paralyzingly complex.

If you listen to modern medical influencers, you’d think surviving the week requires a two-hour morning routine. We are bombarded with endless podcast debates about intermittent fasting windows, the exact minute to get morning sunlight, maximizing VO2 max, and micro-managing gut microbiomes.

But the truth is, 80% of your health comes from the painfully simple stuff:

• Wearing your seatbelt.

• Limiting your alcohol intake.

• Eating reasonably healthy foods.

• Getting standard, age-appropriate health screenings.

• Moving your body regularly.

• Connecting with others to lower your stress.

Chasing that last 20% of peak medical optimization takes a massive amount of energy. Even worse, it can actually cause harm. Over-training leads to bone and joint damage. Extreme dietary restrictions cause unexpected micronutrient deficiencies. The sheer anxiety of tracking every single biometric marker drives up your stress levels.

The Personal Finance Parallel

Personal finance is the exact same beast. You get 80% of the benefit just by following a few boring, foundational rules:

• Earn more than you spend.

• Invest the difference in low-cost index funds.

• Keep your money in the market for the long haul.

• Use a basic, diversified asset allocation.

• Utilize standard tax-advantaged accounts.

Yet, just like in medicine, we obsess over the last 20%. We fall down the rabbit hole of complex Roth conversions, obscure tax loopholes, and alternative investments we don’t fully understand.

The Hidden Cost of “Perfect”

Trying to squeeze out that final 20% of financial optimization often backfires. Overcomplicating your tax strategy can lead to IRS penalties or losing out on healthcare subsidies. Constantly tweaking your portfolio usually results in lower returns than if you just left it alone.

In both health and wealth, the pursuit of perfection demands an enormous tax on your time and mental bandwidth. You end up running on a treadmill, burning precious energy for minimal, if any, real-world gains.

Stick to the simple 80%. It is the most reliable path to being healthy, wealthy, and wise.

Pre-orders now Available

We all have that one expensive bottle of wine, that box of artisan chocolates, or that luxury spa gift certificate we’re saving for the perfect occasion.

And what usually happens? The wine collects dust, the chocolate goes stale, and the certificate expires.

Researchers at Cornell University call this the “precious cargo” effect. We become so afraid of consuming something valuable too early or wasting it on an ordinary Tuesday that we often end up never using it at all.

As it turns out, we do the exact same thing with our life savings.

For decades, the financial industry hammers into our heads exactly how to save, invest, and max out our workplace accounts. But when it’s time to stop working, they leave us completely blind. No one teaches us how to actually decumulate. Because of this massive information gap, our portfolios turn into precious cargo. We become terrified to touch them. In fact, a recent Morningstar study showed that 20 years into retirement, many retirees have only spent down 12% of their principal.

This week on the podcast, I sat down with Jean Chatzky to figure out how to break this cycle. You likely know Jean as the award-winning personal finance author, founder of Her Money, and the former financial editor for NBC’s Today Show.

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Her new book, The Forever Paycheck, tackles the psychology of the decumulation dilemma head-on. As Jean explains it, under-spending isn’t a math problem—it’s a brain problem. When you have to manually liquidate volatile stock market shares every few months to fund your life, every withdrawal feels like a loss.

Her solution is to short-circuit that fear by replacing it with a “forever paycheck”—a regular, anticipated deposit that lands in your checking account automatically.

We talked through the exact mechanics of how to build this, and Jean surprised me. After years in traditional finance media where annuities were largely treated as a scam—she admits she once shut down her own mother’s advisor for recommending one—the data forced her to completely change her mind. She breaks down why academic economists are essentially the “Swifties” of simple immediate annuities, and how converting just one-third of your nest egg into a guaranteed income stream can free up the psychological bandwidth you need to actually enjoy the other two-thirds.

We also get into the weeds on the “lopsided smile” of retirement spending, the uncomfortable reality that over 90% of US homes aren’t physically suitable for aging in place, and how tools like reverse mortgages are being standardized to help.

In the after-show, we discuss a concept I call “escape velocity.” I’ve realized lately that the primary purpose of a massive net worth isn’t actually to fund your retirement—most of us will never spend it all anyway. The real purpose of a massive net worth is simply to give you the guts to leave a job you dislike. Once you make that leap, behavioral strategies like Jean’s forever paycheck are what actually grant you the peace of mind to enjoy the life you’ve built.

It’s a fantastic conversation about the shift from the math of money to the behavior of money.

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For years, I had a very specific fantasy about what my life would look like once I hit financial independence. I pictured a state of perfect nirvana. No alarm clocks. No medical pager going off in the middle of the night. No difficult charting or administrative headaches. I assumed FI meant endless free time and permanent peace of mind.

Then I actually got there.

In my latest “10 Things” solo episode of the Earn and Invest podcast, I pulled back the curtain on the emotional and psychological realities of reaching financial independence. Leaving my full-time medical practice was a beautiful, life changing pivot. But it did not cure my human condition.

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Here is a glimpse at what actually happens when you cross the finish line.

Money Stress Does Not Disappear

Money is a phenomenal tool. It puts a roof over your head, buys your groceries, and gives you the leverage to walk away from a draining nine-to-five. But let me be perfectly clear. Money only solves money problems.

It will not cure your internal feelings of inadequacy. It will not fix a struggling marriage. It will not magically grant you self confidence. FI gives you the emotional time and energy to finally address these deeper issues, but the money itself cannot fix them.

Surprisingly, the financial stress does not disappear when you hit your magic number. The anxiety simply shape shifts. Instead of worrying about covering the rent, you start obsessing over loss aversion. You worry about market drops, the terrifying reality of spending down your assets, and the mind numbing complexity of taxes.

You FI Exactly How You Live

There is a dangerous myth in the personal finance community that reaching FI will somehow flip a switch in your brain and turn you into a relaxed, joyful person.

The reality is that happy people tend to stay happy in retirement, and unhappy people tend to stay unhappy. You carry your pre-retirement temperament right into your post-work life. If you are a high achiever, that relentless drive does not just vanish because you hit a net worth goal.

Instead, retirees often transfer their achievement addiction to new arenas. Suddenly, they are obsessing over longevity optimization or treating neighborhood pickleball matches like the Olympic finals. It is only healthy if you actually enjoy the process, rather than just obsessing over the outcome. Do not wait for retirement to start enjoying your life. Start building connection, meaning, and purpose right now.

The Liberating Reality of Free Time

Pre-retirees constantly ask me if I miss the office or the prestige of my career. The truth? The vast majority of successful retirees do not look back.

Within six to twelve months, most people transition smoothly into new hobbies and social connections. In fact, retirees frequently find their days so full of slow-paced routines and multiplying passions that they wonder how they ever fit a 40-hour work week into their schedule in the first place.

Regaining complete agency over your time without a boss making you feel guilty is incredible. But it also shifts your priorities. While aggressive world travel sounds great on paper, many retirees dial it back after a year or two. Constant travel destroys your daily routines, making it incredibly difficult to pursue the other parts of your identity, like keeping a garden, working out regularly, or eating well.

And speaking of identity, you do not lose yours when you retire. Your hard earned achievements are permanent. Leaving a career simply gives you the space to develop the neglected parts of yourself. And the best part? If you hate being retired, you can always go back to work. With a secure financial foundation, you can volunteer, update your credentials, or return to your old field with absolutely nothing to lose.

Why You Should Want a Massive Tax Bill

During the community segment of the episode, a listener named Jim sent in a fascinating email.

Jim pointed out that because of income taxes and IRMAA Medicare surcharges, pulling money from his IRA to buy a $100,000 Corvette would actually require him to withdraw $140,000.

Taxes in retirement are a massive pain. I will be the first to admit that the cognitive load of navigating quarterly estimates, accountants, and bookkeeping is a persistent headache. But Jim offered a brilliant reframe.

You actually want taxes to be your largest expense in retirement. Why? Because if taxes are not your biggest expense, it means your biggest expense is healthcare.

Paying taxes means things are going well. It is a small thorn in my heel that serves as a constant reminder of how fortunate and painless this phase of life actually is.

If you want to hear my full breakdown of all ten realities, check out the newest episode of the Earn and Invest podcast right now on your favorite player.

What is the one thing you are most afraid of losing when you eventually step away from your career?

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In the personal finance world, we spend a massive amount of time discussing net worth in relationship to our careers, financial independence, and retirement. Today I want to flip the script. Instead of obsessing over net worth, let us consider the concept of margin.

The Space Between Safety and Peril

Margin is simply the buffer between having enough and not having enough. It represents the gap between safety and peril. Throughout our careers, we steadily build this margin with the expectation of one day retiring and not actively making any more income.

During those younger working years, your margin is the gap between what you make and what you spend. We invest that safety valve to build our net worth. As you approach retirement, your margin essentially becomes your net worth. It transforms into the safe amount of money you have saved up to support your lifestyle without running out.

The Anxiety of the Drawdown

A safe withdrawal rate is just a way of hitting a specific safety margin of net worth so you can stop making new money. But a serious psychological problem emerges once we reach this finish line. We prefer to maintain that same or greater margin, and we become incredibly anxious when it goes down.

Retirees currently find themselves caught between two very different streams of thought regarding this dilemma:

This creates a heavy emotional burden. We simply do not know what the real goal for our margin should be. The Die With Zero approach provokes anxiety for many, while the traditional approach leads to hyper-accumulation because we make overly conservative assumptions.

The Reverse Margin Equation

Here is the truth. It is mathematically logical for your margin to decline as you age.

• Understand the timeline: If you step away from work at age 55, your safety margin might need to last for 30 or 40 years.

• Acknowledge the math: As the years pass and you support less lifespan, the heavy lifting required by your savings decreases.

• Allow the creep: Once your safety margin gives you the emotional strength to leave your job, allow that amount to slowly creep downward over time without expanding it.

When we stop viewing net worth as an emotional burden and start viewing margin as a mathematical equation, we relieve our financial anxiety. Forget money. Think margin.

Buy The Healthcare Heist (My latest book)

Years ago, I gave a presentation on hospice care to an audience in San Antonio. I walked into the room wearing a standard button down shirt and slacks. No tie. No sport coat. I assumed my medical expertise and the gravity of the topic would carry the day.

I was completely wrong.

The audience took one look at my casual attire and immediately dismissed my message. Before I even opened my mouth to talk about end of life care, my physical presence had already spoken for me, and it told the crowd I was not someone they needed to take seriously.

That painful memory came rushing back to me during my latest podcast conversation. I sat down with Gina London, an Emmy award winning former CNN anchor, CEO of Language of Leadership, and the author of Amplify You. We dug deep into the mechanics of human connection, the paralyzing fear of public speaking, and why every single interaction we have is a performance.

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We Are Always on Stage

Gina pointed out a truth that made me rethink how I communicate. Public speaking is not just about standing behind a podium with a microphone. All of life is a performance.

This does not mean we need to be fake or manipulative. It simply means people are constantly reading our cues. Whether you are presenting on a massive stage, discussing medical rounds with your peers, or just talking to a barista, you are telegraphing a message. Gina believes communication training is never about changing who you fundamentally are. It is about stacking good habits to amplify your natural self.

We also tackled the pervasive myth that body language and tone make up 100% of communication while the actual words do not matter. Gina calls this the “three-legged stool” of connection. To truly impact an audience, you need perfect balance between your specific word choices, your vocal energy, and your physical posture. If your voice is flat while you tell a passionate story, your message falls apart.

The Human Superpower

We are entering an era where technical tasks are being automated away. Gina shared a fascinating story about her daughter. Her college video game creation course was recently canceled because “vibe coding” can now build games instantly.

AI can generate data and write robotic copy in seconds. But it cannot look someone in the eye, ask deeply empathetic questions, or tell a human story. To survive and thrive, we have to lean into the things a machine cannot fake.

During our after-show segment, we discussed exactly how to do this. We talked about a medical executive who decided to ditch his dry, data heavy slides. Instead, he painted a vivid picture of a specific child whose life was saved, right down to the color of the child’s hair. That is the kind of sensory storytelling that commands a room.

Actionable Steps for Better Connection

Gina offered some incredible, practical exercises to build muscle memory and quiet the butterflies:

• Strategize your memory: Stop trying to memorize your entire speech word for word. You will sound wooden and panic if you drop a sentence. Memorize a killer opening and a strong closing. Use mental bridges to navigate the middle.

• Use the “again” trick: If you stumble, do not apologize profusely. Just say the word “again” and repeat the line cleanly.

• Record yourself: Read a poem out loud on camera. Get comfortable hearing your own voice and pushing the boundaries of your volume and enthusiasm.

• Hide the nerves: Emotional authenticity is great. Visible nervousness is not. Audiences do not want to feel embarrassed for you, so use lighthearted pleasantries when you first walk out to settle your breathing.

At the end of the episode, I also spend some time pulling back the curtain on the professional speaking circuit itself. The heavy travel, delayed flights, and extreme energy demands make it an exhausting lifestyle. For most of us, speaking is best used as a powerful tool to support another passion, rather than the entire career itself.

You can listen to the full conversation with Gina London right now on your favorite podcast player.

When was the last time a speaker completely captured your attention, and what specifically did they do to pull you in?

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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.

Listen Now

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?