app_store_button

google_play_button

DK - Details page - Device banner - 894x1036

Nyd den ubegrænsede adgang til tusindvis af spændende e- og lydbøger - helt gratis

Lyt når som helst, hvor som helst 

Paula Pant | Cumulus Podcast Network

You can afford anything, but not everything. We make daily decisions about how to spend money, time, energy, focus and attention – and ultimately, our life.
How do we make smarter decisions? How do we think from first principles?
On the surface, Afford Anything seems like a podcast about money and investing.
But under the hood, this is a show about how to think critically, recognize our behavioral blind spots, and make smarter choices. We’re into the psychology of money, and we love metacognition: thinking about how to think.
In some episodes, we interview world-class experts: professors, researchers, scientists, authors. In other episodes, we answer your questions, talking through decision-making frameworks and mental models.
Want to learn more? Download our free book, Escape, at http://affordanything.com/escape. Hosted by Paula Pant.

Afford Anything

#679: Will you still have a job in five years? Zack Kass, former OpenAI executive and 16-year AI veteran, joins us to tackle the question that keeps knowledge workers up at night. 

Most people worry about the economics — who can pay the bills if AI takes their job? Kass flips the question: What happens when work no longer defines who you are? He argues we're heading for an identity crisis bigger than any economic disruption.

In this conversation, Kass explains why everyone wants everyone else's job automated (faster legal services, cheaper healthcare) but nobody wants their own work to disappear. 

He shares why some jobs will vanish while others explode in demand, and which professions might actually benefit from AI disruption.

You'll discover why the real threat isn't job loss — it's that we've become addicted to our devices and forgotten how to live without constant work. 

Kass reveals how financial illiteracy keeps people trapped in debt cycles that AI could help break. 

He explains why housing, healthcare, and education costs stay high while everything else gets cheaper, and what might finally change that dynamic.

The conversation explores what happens when AI makes basic needs affordable for everyone. 

Kass predicts some people will pursue passion projects, others will double down on work, and many will struggle to answer a simple question: What do you actually want to do with your day?

We discuss practical realities like how a 53-year-old attorney might reinvent herself, why accountants face bigger challenges than lawyers, and which human skills will become more valuable as machines get smarter. 

Kass shares his theory about competing on kindness rather than intelligence when AI can outthink us all.

This isn't another doom-and-gloom AI prediction. Kass makes a compelling case that automation could free us to rediscover community, creativity, and purpose … if we can get past our addiction to both work and screens long enough to imagine what that life looks like.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(0:00) Introduction

(2:00) Zack's AI background at OpenAI

(3:15) Will knowledge workers have jobs

(4:52) Job automation is complex

(7:53) Longshoremen strike over automation

(9:06) Everyone wants others' jobs automated

(10:14) Identity crisis bigger than economics

(13:36) Lawyers might enjoy job loss

(21:42) Societal thresholds stop automation

(28:52) Bespoke services always find demand

(41:34) AI won't replace human therapists

(47:11) Dehumanization threatens physical connections

(54:55) Financial illiteracy costs billions

(1:03:21) Predatory lending traps explained

(1:11:51) Housing healthcare education stay expensive

(1:26:31) Screen time hides free time

Resource:

AffordAnything.com/financialgoals

Share this episode with a friend, colleagues, the Permabulls and the Permabears: https://affordanything.com/episode679

Learn more about your ad choices. Visit podcastchoices.com/adchoices

Why AI Taking Your Job Isn't the Real Problem, with Fmr. OpenAI Exec Zack Kass

#678: Anonymous (01:52): "Victoria" is 51, single, and still enjoying their W2 job while building a side business from a passion hobby. They’re thinking about heavy Roth conversions, planning for retirement, and wondering how much traditional money to leave untouched. Should Alex prioritize tax efficiency, or focus on growth and flexibility?

Anonymous (34:29): "Gwyneth" and her husband moved to the U.S. to start a sanctuary for senior dogs and cats. With $100,000 in debt soon paid off, two properties in hand, and a dream to buy land for their sanctuary, they’re torn: sell, refinance, or keep their rental property? What’s the best way to fund a long-term dream while building wealth?

Soyman (53:28): Soyman is 25, saving aggressively, and planning to take all of 2027 off to go backpacking. They see a rare tax opportunity to convert nearly $30,000 to a Roth at a negative tax rate—but is the strategy worth the small cash buffer and other risks?

Resource Mentioned:

 Interview with Charity: Water founder Scott Harrison

Share this episode with a friend, colleagues, your veterinarian: https://affordanything.com/episode678
Learn more about your ad choices. Visit podcastchoices.com/adchoices

Q&A: We Want to Save Senior Dogs … But Should We Sell Our Rental to Do It?

#677: Happy New Year! We're kicking off 2026 with a reality check on where your money stands right now.

The Good News: Gas prices dropped below $3/gallon. Inflation cooled to 2.7%. The Fed cut rates again. GDP grew 4.3% (surprisingly strong). Gold hit $4,500 an ounce. And 19 states raised minimum wages.

The Not-So-Good: Health insurance jumped 10-18%. Unemployment ticked up. Mortgage rates are stuck around 6.2%. And 80% of homeowners are unlikely to sell because they locked in rates below 6%.

The Big Picture: The stock market is outperforming the economy.

How It Affects You: I call it "millionaire malaise."

Your 401k looks great. Your home equity is through the roof (no pun intended). If you bought before 2022, your assets look good on paper.

Yet you're stressed out at the grocery store.

Everything costs more – insurance, groceries, everything except gas. Jobs are stagnant. People are stuck.

We're experiencing the difference between wealth and income.

This is 2026: Wealthy on paper. Broke at the checkout line.

Whether you're new to money management or a long-timer looking for clarity, this episode cuts through the noise to tell you what actually matters for your finances this year.

 Download the free resource: AffordAnything.com/financialgoals

Timestamps

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(01:33) Warren Buffett's retirement

(04:45) Unemployment at 4.6% in November

(06:11) JOLTS data and November jobs data

(08:04) Gold hitting record highs above $4,500/oz in December

(11:26) US inflation at 2.7% in December

(20:01) Commerce Department releases GDP numbers at 4.3%

(23:08) Gas prices hitting record lows

(25:20) Mortgage rates holding around 6.20% 

(30:26) Minimum wage increases in 19 states

(32:23) Health insurance premiums up 10% (employer) and 18% (individual)

(35:15) $12 billion USDA aid package for farmers

(37:16) Workers over age 50 listing more disruptive tech skills on resumes

(39:21) Consumer Sentiment rose in December

Share this episode with a friend, colleagues, and cohorts: https://affordanything.com/episode677
Learn more about your ad choices. Visit podcastchoices.com/adchoices

First Friday: What 2026 Means for Your Money

#676: Ally:How can I optimize my asset allocation and Roth contributions now that I’m over $1 million in assets?

I’m 45, single, never married, with about $1.2 million in assets. Roughly $100,000 is in stocks, which might scare some people. 

Here’s my breakdown:

 
Vanguard brokerage account: VTSAX $132,000, ISCV $5,000, VOO $5,000

 
Vanguard Rollover IRA: VTSAX $65,000, IVV $25,000, VOO $62,000

 
Vanguard Roth IRA: VTSAX $228,000, ISCV $6,000

 
Pre-tax 401(k): Active stock fund $218,000 (0.01% expense ratio), Equity dividend fund $55,000 (0.01% expense ratio)

 
Russell 1000: $270,000 (0% expense ratio)

 
HSA: $9,000 in the Russell 1000 and Russell 2000

 
ESPP: $90,000

 
Savings account: $12,000

I view my brokerage accounts as savings, where I can sell assets if I need cash, as well as sell my company shares.

My questions: How far am I from the efficient frontier? How efficient is my asset allocation? I’ve mostly been a “VTSAX and chill” type. If I rebalance, what’s the best way to do it without incurring taxes?

Next year, I’ll make more than $150,000, even after contributing $24,500 to my pre-tax 401(k) in 2026. Can I still do a backdoor Roth, given that I already have an IRA balance? I was told it could be complicated. Am I out of luck investing in a Roth next year?

Also, should I roll over my 401(k) into my existing Rollover IRA to gain more investment options, even though the 401(k) fees are very low?

I’ve reached over $1 million in assets, but I’m not confident my first million was invested efficiently. I want to correct it before reaching my next million.

Emma: Can We Split a Dependent’s Tax Status Midyear to Maximize Health Insurance Subsidies?

We’re a family of four with two adults and two children, ages 15 and 21. Our 21-year-old is a full-time university student and is expected to graduate in May 2026. The hope is that she’ll secure a full-time job after graduation.

Our health care broker told us that we could claim her as a dependent for half of the year and then have her claim herself for the second half. According to the broker, this would allow her to stay on our health insurance and help us qualify for a larger premium subsidy.

Is it actually possible to split a dependent’s tax status this way within a single year, or is this a misunderstanding?

Anonymous: Is It Wise to Hold Some Investments Outside the U.S. for Geopolitical Diversification?

I’ve always believed that “this time isn’t different,” but lately I’m feeling uneasy.

I’m increasingly concerned about what seems like a slow erosion of institutional trust in the U.S., especially regarding agencies and structures that support our financial system. From leadership changes at key government institutions to growing political influence over economic policy, I’m starting to wonder if it’s prudent to hold a small portion of assets physically and legally outside the U.S.

I’m not talking about exotic offshore schemes. I mean legitimate ways to invest in broad index funds or ETFs through a brokerage account based abroad—as a form of geopolitical diversification and personal contingency planning. I’d love to hear your perspective.

Share this episode with a friend, colleagues, your brokerage rep: https://affordanything.com/episode676
Learn more about your ad choices. Visit podcastchoices.com/adchoices

Q&A: Should You Keep Part of Your Money Outside the U.S.?

#675: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E.

Today’s letter E stands for Entrepreneurship. This episode originally aired in September 2018, at a moment when startup culture was loud, venture capital was abundant, and entrepreneurship was often framed as something that involves outside investors and rapid growth.

____

In this episode, we rewind the clock to 2018. Remember what entrepreneurship was supposed to look like back then?

Build a startup. Raise capital. Scale fast. Get rich.

That was the dominant story.

But our guest, Rand Fishkin, told a different story – a story about founder burnout, debt, and the downside of startup culture.

Rand, the founder of Moz, shares how he and his mother accumulated nearly half a million dollars in debt while running an early services business.

He talks about what it felt like to face creditors, negotiate settlements, and keep going under intense financial pressure.

From there, we move into one of the most misunderstood ideas in entrepreneurship: the difference between service businesses and product businesses.

Rand breaks down the trade-offs. Services generate income faster. Product businesses rely on outside capital. And founders often earn far less than people expect.

That leads to a deeper conversation about incentives.

Once venture capital enters the picture, priorities shift. Profits matter less. Growth matters more — and it affects both the business and your personal finances.

High revenue does not automatically translate into personal wealth.

We also talk about the side of entrepreneurship that rarely makes the highlight reels: Loneliness. Anxiety. Depression.

And the relief that comes from realizing that even the most successful founders often feel lost while they’re building.

This conversation feels less like startup advice and more like a long-term framework for thinking clearly about risk, money, and meaning.

If you’ve ever questioned whether entrepreneurship automatically leads to financial freedom, this episode offers a grounded and very honest answer.

Timestamps

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(00:00) Facing creditors and repayment negotiations

(08:50) How a services business really works

(11:40) From consulting to software

(15:00) Services vs. product businesses

(12:20) Why high revenue doesn’t mean personal wealth

(25:05) Venture capital incentives

(27:50) Founder salaries and financial reality

(30:40) Startup mythology vs. lived experience

(33:20) Loneliness and mental health

(36:15) Founder strengths and weaknesses

(39:50) Feedback and self-awareness

(42:30) Designing a business that fits your life
Learn more about your ad choices. Visit podcastchoices.com/adchoices

[E] The Myths We Believed About Startups [GREATEST HITS]

#674: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E.

Today's letter R stands for Real Estate. This episode originally aired in May 2022, but the insights on long-distance investing remain just as relevant for anyone feeling priced out of their local market.

We tackle the five biggest challenges of investing far from home – from fear of the unknown to managing contractors remotely – and reveal four compelling benefits that make it worth the effort, especially when you're competing in markets where million-dollar properties are the norm.

________

Remember when inflation was high and rates were rising? 

What were people saying about real estate back then? 

And with the benefit of hindsight, how much of what we thought at the time proved to be correct? 

If you feel unsettled, join the club. At this present moment – December 2025 – interest rates are falling, but not enough. Inflation is mostly under control, but not enough. 

The noise makes everything feel new.

When you only see the present moment, everything looks obvious. When you remember the past, patterns start to show. 

That's why we’re rewinding the clock back to May 2022 – when interest rates were rising and inflation was near its peak. 

So what was on our mind three years ago? 

We start with the basics. 

Why the Federal Reserve raises rates. What higher borrowing costs do to spending. Why falling stock prices often reflect fear – not proof that housing prices must fall next. 

We explain the difference between recession and deflation, and why the two are often confused.

We walk through what made the housing market in 2022 different from 2008. Inventory was tight. Builders had not overbuilt. Many homeowners held fixed-rate mortgages and record levels of equity. 

Those conditions mattered then. They still matter now.

That equity becomes the next focus. We talk about cash-out refinances, HELOCs, and reverse mortgages – and what happens when homeowners borrow against rising values. 

You hear how higher rates can slow borrowing, why that matters for inflation, and what risks appear if some borrowers struggle to repay.

From there, we outline four ways investors might encounter properties if foreclosures rise: bank-owned homes, short sales, “subject to” deals, and wraparound mortgages. 

The episode then shifts to long-distance real estate investing. You hear the real challenges. Fear of the unknown. Managing people you cannot see. Contractors who disappear. Agents who stop returning calls.

You also hear what makes distance workable: education, relationships, local investor networks.

We walk through how investors think when conditions feel unstable — and why looking backward sharpens how you see what comes next.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(0:00) Trade-offs and priorities

(07:41) Fed hikes rates

(09:16) Inflation drivers explained

(11:26) Recession vs housing

(13:21) Home equity surge

(15:21) Borrowing against equity

(17:11) Foreclosures and options

(18:26) Subject-to and wraps

(21:11) Shift to distance investing

(25:31) Education and networks

(31:36) Choosing markets

(36:11) Accountability challenges
Learn more about your ad choices. Visit podcastchoices.com/adchoices

[R] Remember When Inflation Was High and Rates Were Rising? [GREATEST HITS]

#673: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E.

Today's second letter I stands for Investing. This episode originally aired in April 2022, but the framework remains one of the most practical guides we've shared for building wealth at any age.

Nick Maggiulli joins us to reveal why most young investors obsess over the wrong metrics — and shares his Save-Invest Continuum that shows exactly when your savings beat your investment returns, and when that changes. 

_____

When Nick Maggiulli was in his twenties, he spent countless hours obsessing over his investment portfolio – tweaking his asset allocation, running net worth projections, and building complex spreadsheets. 

Meanwhile, he was blowing $100 every weekend partying in San Francisco.

It took him years to realize the absurdity. His annual investment returns on his tiny $1,000 portfolio might earn him $100 – the same amount he'd spend in a single night out.

Maggiulli joins us to explain why young investors focus on the wrong things and shares his framework for knowing when to prioritize saving versus investing. 

He introduces the Save-Invest Continuum, which compares your expected annual savings against your expected investment returns. 

When you're starting out, your ability to save dwarfs any investment gains. A $6,000 annual savings capacity beats a $100 investment return every time.

We discuss the math behind saving 50 percent of future raises, not for guilt or deprivation, but to maintain lifestyle balance while building wealth. 

This rule applies only to real raises above inflation. If you get a 3 percent raise during 3 percent inflation, you haven't actually gotten ahead.

The conversation turns to unconventional income-producing assets. Beyond stocks and bonds, Maggiulli explores farmland investing, which offers returns uncorrelated with traditional markets. 

He shares the story of someone who bought the royalty rights to Jay-Z and Alicia Keys' "Empire State of Mind" for $190,000. The song earned $32,733 in royalties the previous year — an 11 percent return if that income stays constant.

We examine why 85 to 90 percent of your portfolio should generate income through dividends, rent, interest, or business profits. 

Maggiulli keeps his speculative investments — cryptocurrency, art, and individual stocks — under 10 percent of his net worth. He admits his two individual stock picks are down 60 to 70 percent, proving his own point about avoiding stock picking.

The episode reveals that time remains your most important asset. Warren Buffett would likely trade his entire fortune — and go into debt — to be 35 again. 

This perspective shapes every financial decision, from choosing income strategies to deciding between assets that merely appreciate versus those that pay you while you sleep.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(00:00) Nick's mistake of obsessing over investments while partying away returns

(05:31) The Save-Invest Continuum explained

(08:11) When savings matter more than investment returns

(12:31) Focusing on both saving and investing in midlife

(13:11) Crossover point: when investment returns exceed spending

(14:11) The 2X Rule for guilt-free spending

(15:31) Save 50 percent of future raises

(20:41) Five ways to increase income

(26:31) Selling time versus selling skills

(28:11) Teaching and creating products for income

(30:11) Climbing the corporate ladder

(31:11) Converting human capital to financial capital

(32:31) Income-producing versus speculative assets

(36:11) Individual stocks and cryptocurrency allocation

(43:51) Farmland investing basics

(45:31) Royalty investing example

(49:31) Art and non-income producing assets

(51:11) Inflation and debt strategies
Learn more about your ad choices. Visit podcastchoices.com/adchoices

[I] Why Young Investors Focus on the Wrong Things [GREATEST HITS]

#672: Welcome to Greatest Hits Week — five days, five episodes from our vault, spelling out F-I-I-R-E.

Today's letter I stands for Increasing Your Income. This episode originally aired in August 2024, but the strategies are more essential than ever. 

Jeff Wetzler, Ed.D., reveals why the people around us withhold crucial information — and how asking better questions can transform your negotiations and net worth.

__________

You've mastered the art of asking for what you want — or have you?

Jeff Wetzler, Ed.D., a former education executive, joins us to reveal why most of us fail to extract crucial information from the people around us. 

Think about it: when was the last time someone told you what they really thought about your work? Or shared that game-changing idea they'd been sitting on? 

Wetzler discovered four categories of information people routinely withhold — and the cost runs deeper than you might expect.

We explore why people stay silent about their struggles, unpopular opinions, observations about us, and innovative ideas. 

The reasons range from fear to simple exhaustion, but one stands out: they don't think we want to know.

Here's a startling example from Harvard Business School research: investigators planted smudges on their faces and surveyed people. Less than three percent told them about the mark that they could wipe off in one second. But when asked later, 100 percent had noticed it. 

If people won't share something that simple, what else are they keeping from us?

Wetzler shares his Ask Approach — five steps that unlock hidden information in any negotiation or relationship. We walk through real scenarios, from salary negotiations to buying cars, showing how curiosity beats strategy every time.

One mechanic story drives this home. Facing a $2,000 air conditioning repair, Wetzler asked one question: "Do you have any other creative ideas?" The mechanic paused, then offered a $75 solution that worked perfectly. That five-second question saved $1,925.

We discuss practical listening techniques, including the "doorknob moment" — why therapists know the most important information comes at minute 49 of a 50-minute session. Wetzler explains why our minds process 900 words per minute while our mouths manage only 125, creating a massive information gap.

The conversation includes AI's surprising role in sharpening these skills, helping us frame conversations into content, emotion, and action. 

Wetzler demonstrates how technology can enhance rather than replace our uniquely human ability to connect and learn from each other.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(00:00) What's at stake in asking better questions

(02:33) Four categories of information people withhold

(06:33) The smudge experiment reveals our silence

(09:13) Why people don't tell us what they think

(12:53) The Ask Approach begins with curiosity

(14:48) Making it safe for truth-telling

(18:53) CEOs share how to get honest feedback

(22:13) Posing quality questions vs crummy questions

(30:58) Listening across three channels

(34:28) The doorknob moment phenomenon

(37:43) How to listen better in negotiations

(42:13) Reflect and reconnect strategies

(44:53) Applying the Ask Approach to car buying

(51:33) Working through a complete negotiation

(01:02:13) Using AI to sharpen your asking skills

(01:06:13) Why this approach is learnable
Learn more about your ad choices. Visit podcastchoices.com/adchoices

[I] The Hidden Information That's Costing You Money [GREATEST HITS]

#671: Welcome to Greatest Hits Week — five days, five episodes from our vault, spelling out F-I-I-R-E.

Today's letter F stands for Financial Psychology. And we're diving deep with a conversation that changed how thousands of our listeners think about money.

This episode originally aired in November 2022, but the insights feel more relevant than ever. Dr. Daniel Crosby reveals why your brain is your portfolio's worst enemy — and what you can do about it.

______

Money is the number one stressor in American lives. Every single year. Without exception.

That's what Dr. Daniel Crosby discovered when he looked at decades of research from the American Psychological Association.

In this rerun episode from our Greatest Hits Vault, Crosby joins us to reveal why your brain sabotages your investment decisions. He's both a clinical psychologist and behavioral finance expert. His findings will change how you think about money.

Your body hijacks your financial judgment in strange ways. For example:

People who need to pee become more risk-averse investors. It's called inhibitory spillover. When you're controlling your bladder, you also restrict your financial decisions.

Here's another one: judges give harsher sentences when they're hungry. Thousands of court decisions prove it. The best predictor of whether you get jail time? When the judge last ate.

We explore four behavioral risks that destroy wealth: ego, conservatism, attention, and emotion.

Crosby shares data that stock pickers rarely hear: 74 percent of individual stocks have a lifetime expected return of zero. Three out of four companies eventually go bankrupt. Yet people keep betting on single stocks, dreaming they'll find the next Apple.

Value investors suffer from depression and social isolation. Why? Because contrarian investing fights our deepest evolutionary wiring. Humans survived through cooperation. It's literally our only advantage over other animals. Bears have claws. Turtles have shells. We have teamwork.

Crosby shares the Ash experiment, which shows how peer pressure warps reality. When nine people give the wrong answer about line lengths, three-quarters of participants follow along. New brain scans reveal something darker: social pressure physically changes how people see the lines. Their perception actually shifts.

We discuss solutions through Crosby's "three E's": education, environment, and encouragement. Reading about biases won't fix them. You need systems and people.

One powerful study: people who saw their children's photo for five seconds before banking saved twice as much money.

The conversation reveals that money problems don't disappear with wealth. They just change form.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(00:00) Finance as America's top stressor

(02:33) Psychology moving from brokenness to wellness

(04:33) Money touches every part of life

(07:33) Income plateaus and happiness

(10:13) How hunger affects financial decisions

(13:38) We're wired wrong for investing

(17:28) Laziness and cognitive shortcuts

(23:43) Cooperation as human survival trait

(26:43) Four behavioral risks

(32:13) Ego and overconfidence

(37:48) Conservatism and familiarity bias

(46:38) Three E's of behavior change

(50:23) Attention risk and probability

(54:48) Emotion derails decisions

(58:28) When fear helps versus hurts

Learn more about your ad choices. Visit podcastchoices.com/adchoices

[F] Why Your Brain Sabotages Your Money [GREATEST HITS]

#670: As we close out 2025, premium credit cards are more expensive and more complicated than ever. It’s fair to ask whether the points game is still worth the effort.

We sit down with Chris Hutchins, host of All the Hacks, to talk about what’s changed in credit card rewards, and how to decide whether to stick with travel points, switch to cash back, or run a hybrid strategy that keeps your life simple.

We dig into the “value” problem behind all those new credits and perks. Instead of letting a card dictate our spending, we walk through how to price credits based on what we would genuinely pay for them, and when it’s smarter to downgrade, negotiate a retention offer, or product change and keep your credit history intact.

We also get tactical about booking travel in 2026: newer award search tools, how much flexibility matters, and a sneaky alternative most people forget, sometimes you can buy points directly and still get a strong deal without years of “earning.”

If you want to earn more points (or waste less time chasing them), this conversation will help you reset your credit card strategy for 2026 with a clearer definition of what “worth it” even means.

Key Takeaways

 “Credits” are not value unless we were already going to buy the thing, and we’d happily pay close to face value for that discount

 The points game is still powerful, but mostly through welcome offers, not micro-optimizing bonus categories

 Flexibility is the hidden lever in award travel, the best deals often show up when we loosen the date, airport, or destination constraints

 Cash back is having a moment, especially if we want simplicity and fewer mental tabs open.

 Before canceling a fee card, we can often negotiate, downgrade, or product change and keep the credit history we’ve built

 Sometimes the best move is to stop “maximizing,” take the trip, and protect our time for higher-impact work (or actual rest)

Resources and Links

 Chris Hutchins, All the Hacks (https://www.chrishutchins.com)

 Our deep dive on credit reports and scores, Episode 221

 YouTube video mentioned on why airline loyalty programs can be worth more than the airlines themselves

 FlyFlat.com

 Seats.Aero

 Point.me

 Rome Travel

 AwardTool.com

 
PointsYeah.com Daydream Explorer

Chapters

Note: Timestamps are approximate and may vary greatly across listening platforms due to dynamically inserted ads.

(01:22) The 2025 reset for premium credit cards

(06:18) How the points game actually works in 2025

(10:29) Rethinking economy flights versus business class

(16:37) Managing credit cards during major life transitions

(23:57) Simplicity versus optimization in the points ecosystem

(36:45) Luxury perks, rising fees, and who premium cards serve

(43:34) Buying points directly instead of playing the game

(58:44) Using AI and systems to build better money habits

Learn more about your ad choices. Visit podcastchoices.com/adchoices

Q&A: We Want to Save Senior Dogs … But Should We Sell Our Rental to Do It?

Lyt når som helst, hvor som helst

Other podcasts you might like ...