Anyone else a little tired of hearing about ‘retirement?’ It can feel like this vague, far-off finish line that we're told to obsess over for decades. But here's the thing: when you look at the research, a surprising number of people who are retired—or about to retire—are anxious. They've got regrets. Some of those regrets are financial. But many have nothing to do with money at all. So if we're going to spend years working toward retirement, we should probably make sure we're aiming for one we'll actually enjoy. Joel has known Wes Moss for a long time. They worked at the same radio station for well over a decade. He's still there because, believe it or not, terrestrial radio is still alive and well. His show, Money Matters, has helped countless listeners make smarter decisions about their money, their investments, and, yes, their retirement. Wes has a new book out that challenges a lot of conventional thinking about what makes retirement successful, and today we're diving into the financial and non-financial choices that can help you avoid the regrets so many retirees have. Today we discuss: Why his new research updates his earlier work on happiest retirees rather than replacing it entirely. Fear around retirement is often amplified by nonstop media coverage. Wes says more money alone does not erase anxiety, even for people with $3 million or more. Wes defines happiness in a more Aristotelian way, focusing on fulfillment and purpose rather than pure pleasure. He introduces “money green zones” for investable assets, income, and years left on a mortgage, arguing that happiness rises when retirees land in those ranges. A major theme is core pursuits, which Wes describes as hobbies on steroids. The happy retiree group tends to have 5 or more, and they spend about 20 hours a week on them versus about 13 for less happy retirees. Wes warns that purpose does not just appear in retirement. It has to be built intentionally well before leaving work. They talk about the “friendship recession” and how it gets harder to make close friends with every decade, making community a key retirement asset. The conversation also covers the emotional power of being able to say you could retire now, even if you choose not to. Wes says that confidence correlates with a 21% jump in happiness. On the financial side, Wes explains why a retirement plan, safe assets, and a flexible withdrawal strategy can reduce fear and improve spending confidence. They discuss Social Security timing, with Wes leaning toward using it sooner if doing so helps someone retire a year or two earlier and live better. How much of a remaining mortgage leads to higher levels of happiness And much more!   Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances: Cashback credit cards: Check out our favorite credit cards that we use to maximize rewards and optimize our spending. Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group! Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical. Money Gears: knowing what to do with your money is crucial to your personal finance journey. MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.   And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!   Best friends out!See omnystudio.com/listener for privacy information.

We’re kicking off the week by answering your listener questions! And if you have a question that you’d like for us to answer on the show, we’d love for you to submit your own via HowToMoney.com/ask , send us your voice memo. Regardless of how random or bizarre you might think it is, we want to hear it!   1 - Extra cash: Should we use our savings to pay down a mortgage that’s at 2.8% for 30 years? 2 - Brokerage taxes: How do I prepare for paying taxes on dividends and could you explain ‘tax drag’? 3 - Credit card apps: Am I crazy for feeling hesitant to enter my credit card information into card maxing apps? 4 - Hot and tired: Our window units aren’t keeping up with the heat so is it OK to finance central air?   Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances: YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE! Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending. Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group! Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical. Money Gears: knowing what to do with your money is crucial to your personal finance journey. MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense. During this episode we enjoyed a Forgotten Lake by Lake of the Woods Brewing… thank you David S for sending this one our way! And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!   Best friends out!See omnystudio.com/listener for privacy information.

Time for a Friday Flight- our little sampling of the week’s best financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and helpful stories like: Matt’s big reveal Slick deals lingerie America’s debt debacle Job hopping superpower Quick responses “Leave the workforce” clause in prenups Joint back accounts and happy couples Is buy now pay later all that bad? Perpetual shopping Mystery vacations to save Travel e-sim boom   Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances: YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE! Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending. Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group! Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical. Money Gears: knowing what to do with your money is crucial to your personal finance journey. MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense. And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!   Best friends out!See omnystudio.com/listener for privacy information.

“There’s nothing new under the sun.” That comes from Ecclesiastes. But it’s a piece of wisdom we tend to neglect. It's often said that those who forget history are doomed to repeat it. But what if a poor understanding of history does something else too: leaving us less grounded and giving us unrealistic expectations about how life used to be? It’s time for a history lesson today, but not just for the sake of memorizing names, dates, and events. Drawing on countless examples from history, national bestseller Joseph Moore argues that while we're constantly looking back with nostalgia at the "good old days," we may actually be living through the greatest era of prosperity. The books is How To Get Rich In American History, and today we unpack: Why Americans misunderstand the past and over-romanticize earlier eras The American Dream has been declared dead for centuries Optimism and an internal locus of control matter financially Why “stocks for the long run” is a modern idea Early Americans were often told not to save money Real estate myths: it does not always go up and it is not passive FIRE as the CrossFit of personal finance Women’s income has long been central to family wealth Five takeaways from history: solve problems, take risks, move, marry well, believe you can do it And much more! Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances: Cashback credit cards: Check out our favorite credit cards that we use to maximize rewards and optimize our spending. Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group! Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical. Money Gears: knowing what to do with your money is crucial to your personal finance journey. MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.   And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!   Best friends out!See omnystudio.com/listener for privacy information.

We’re kicking off the week by answering your listener questions! And if you have a question that you’d like for us to answer on the show, we’d love for you to submit your own via HowToMoney.com/ask , send us your voice memo. Regardless of how random or bizarre you might think it is, we want to hear it!   1 - HSA: I don’t see how investing money in a Health Savings Account is going to move the needle for me? 2 - Dividend stocks: I keep buying individual stocks, but maybe it’s time to cut bait? 3 - Renovate/rent: We’re interested in getting into single family housing but how do we go about it? 4 - Cash reserves: What steps do I take to have 1-3 years of cash on hand for retirement?   Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances: YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE! Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending. Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group! Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical. Money Gears: knowing what to do with your money is crucial to your personal finance journey. MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense. During this episode we enjoyed a Lakeside Kolsch by Lake of the Woods Brewing… thank you David S for sending this one our way! And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!   Best friends out!See omnystudio.com/listener for privacy information.

Time for a Friday Flight- our little sampling of the week’s best financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and helpful stories like: Friends and money in The Guardian Ubiquitious sports-betting Friendly financial advice Whole Foods on the cheap Suveillance grocery pricing Student loan pause = mostly bad outcomes Goodbye Grad and Parent Plus Home equity piggy banks Monitoring for fraudulent credit card charges Checks are for chumps (Jay Z on the power of cash) Vans are back baby! “Dumb” cars Flock cameras… good or bad?   Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances: YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE! Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending. Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group! Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical. Money Gears: knowing what to do with your money is crucial to your personal finance journey. MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense. And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!   Best friends out!See omnystudio.com/listener for privacy information.

What’s harder: parenting… or the cost of it? We’re huge fans of having kids. They teach you so much, force you to become less self-absorbed, and – let's be real – it’s incredible to watch little mini versions of yourself running around bringing so much joy, purpose, and chaos to your daily life. But financially? Raising a family can feel more daunting than ever. Between housing, childcare, activities, and expenses that seem to multiply overnight, many parents are left asking: How do we make this work? That’s why we’re joined today by Kristy and Bryce of Millennial Revolution. They’ve written a practical new book, Parent Like a Millionaire (Without Being One), on raising kids thoughtfully and confidently without needing a seven-figure bank account. Today we discuss: The impact of money on birth rates Myths and facts of the cost or raising a child “Big Baby” Living smaller and avoiding unnecessary life upgrades Nanny sharing and childcare alternatives Teaching kids financial autonomy and independence Joys of parenthood Gift of financial independence while parenting And much more! Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances: Cashback credit cards: Check out our favorite credit cards that we use to maximize rewards and optimize our spending. Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group! Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical. Money Gears: knowing what to do with your money is crucial to your personal finance journey. MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.   And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!   Best friends out!See omnystudio.com/listener for privacy information.

We’re kicking off the week by answering your listener questions! And if you have a question that you’d like for us to answer on the show, we’d love for you to submit your own via HowToMoney.com/ask , send us your voice memo. Regardless of how random or bizarre you might think it is, we want to hear it!   1 - House poor: What to do when all your money goes towards your mortgage? 2 - Aldi: Is it true that the best budget grocery store isn’t taking the AMEX Blue Cash Preferred anymore? 3 - Expensive babies: Should I plan to carry newborn delivery costs on a credit card? 4 - Car dealership: How can I avoid fees and cut other costs when I shop for a car at the dealership?   Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances: YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE! Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending. Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group! Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical. Money Gears: knowing what to do with your money is crucial to your personal finance journey. MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense. During this episode we enjoyed a Juicy A by Flying Monkey Brewing… thank you David S for sending this one our way! And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!   Best friends out!See omnystudio.com/listener for privacy information.

Time for a Friday Flight- our little sampling of the week’s best financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and helpful stories like: Thoughts on the $20 burrito Real wages rise a little Cash hoarding Big banks are still sticking it to you Spendy sports Shot-through shirts WFH fees Pension-ification of your 401k Gen Z investing in WHAT?! Mandated self checkout WhatNot to buy   Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances: YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE! Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending. Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group! Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical. Money Gears: knowing what to do with your money is crucial to your personal finance journey. MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense. And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!   Best friends out!See omnystudio.com/listener for privacy information.

Frugality is a cornerstone of personal finance advice: cut back, spend less, reduce waste. And for the average American drowning in debt, that’s often solid advice. But money isn’t meant to just sit there untouched—it’s also meant to be spent, experienced, and enjoyed. In fact, even the money you save is really just deferred spending. And let’s face it: money isn’t easy to come by. We work hard for every dollar we earn. So maybe the answer isn’t simply spending less. Maybe it’s spending with more intention. Our guest today wants you to worry less about money, and he argues that the path there isn’t endless deprivation—it’s changing the way you think about spending altogether. Jesse Mecham is a best-selling author and founder of YNAB, the beloved budgeting app that’s helped millions take control of their finances. Today we discuss his brand new book, Never Worry About Money Again, and dive into concepts like: Financial worries are a low grade hum Money as an expression of self Why Jesse believes we should love money Aligning money with life goals and values Influence of interior work and self-awareness Practical tips for simplifying money systems Kids as a status symbol What it means to be a “rec league” family And much more! Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances: Cashback credit cards: Check out our favorite credit cards that we use to maximize rewards and optimize our spending. Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group! Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical. Money Gears: knowing what to do with your money is crucial to your personal finance journey. MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.   And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!   Best friends out!See omnystudio.com/listener for privacy information.