The Stacking Benjamins Show

You build a plan around a goal, the goal changes, and the spreadsheet keeps marching toward the old one. Joe Saul-Sehy and a roundtable of regulars, joined by Financial Bliss Coach Kelley Long, CFP, ask what happens when the house, the career, or the family you saved for stops being the life you want. They play a game of keep it, kill it, or change it, then get practical about the real invoice for changing course: cash runways, taxes, selling while markets are down, and the stubborn pull of sunk costs. You’ll also hear why staying put has a price of its own.
What You’ll Walk Away With
A three-card game (keep it, kill it, change it) applied to a house the kids have outgrown, a plan built around children that no longer applies, and a career plan with a countdown
Why people regret never questioning a goal far more than missing it, and what a story from base camp has to do with it
How to tell whether you want to stop working or just want out of a job you’ve outgrown, a lot like mistaking thirst for hunger
The “invoice” for changing course, and the fixed expenses worth covering for a year while you figure it out
A test-drive trick that lets you feel a change before you make it
A way to compare a big decision by taking the money out first and asking what you’re really trading
What to do when you need cash and your investments are down
Why a big tax bill can be worth paying, and what happens when a rule of thumb swallows the reason behind it
Sunk cost versus switching cost, and why only one of them is a feeling
The “too small blanket” problem, and the flexibility you can build in from the start
Why This Matters Now
Most of us spend plenty of energy checking whether we’re on track, and very little asking whether we still want to go where the track leads. If you worry about a change you can’t undo, or you’ve outgrown a plan you built with good intentions, this conversation treats changing your mind as a cost you can plan for. Getting good with money was never about living yesterday’s life more efficiently. It was about having more choices tomorrow.
From the Basement
Joe reports that his new tendon came from an Olympian, at his request, and that standing up is now a major athletic event. Doug’s trivia is a cautionary tale about the worst side hustle ever pitched, and the Detroit Lions provide a live demonstration of a plan with an Achilles heel.
Resources Mentioned
Financial Bliss Coach: Kelley Long’s coaching practice, with links to her podcast and book
But Who Will Take Care of You When You’re Old? Financial Planning for People Without Kids by Kelley Long: her forthcoming book on planning without children
Lynda Gratton: What If You Live to 100? Here’s How to Actually Plan For It: our conversation on the hundred-year life

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Most of us are optimizing a number, whether it’s a retirement balance or a job title, and almost never stop to ask what it’s for. Wharton economist Corinne Low measures how people really trade time, money, and love, and she has a short exercise that shows how little of your ideal life depends on that number. Joe Saul-Sehy and guest co-host Anna Allem, CFP, put her ideas to work on careers, partnerships, and the awkward conversations in between. You’ll hear why a house can act as insurance in a marriage, why your job won’t love you back, and how to walk into a hard conversation holding real leverage.
What You’ll Walk Away With
A two-minute exercise that shows what your money is actually for
Why almost nobody in that picture is working long weeks, and what that says about your calendar
What economists mean by “utility,” and why it’s richer than happiness
The case for “having it almost,” and why dropping perfect can raise satisfaction
BATNA, a negotiation term worth knowing, and how to build yours before a hard conversation at work or at home
The coin flip study: why people nudged out of a stuck situation ended up happier
Why buying a home can act as insurance in a partnership, and who that lets take a step back
Why your job is a tool for converting time into money, and why that’s good news
Quick-fire answers on splitting bills 50/50, who gets the last word on big purchases, and whether prenups are only for the wealthy
One thing to put on your calendar this week that makes you richer without earning a dollar
Why This Matters Now
Most of us are working hard toward a finish line we’ve never described out loud. That makes it easy to keep climbing, keep saving, and keep wondering why the finish line keeps moving. If you worry about making a move you can’t undo, or you feel like everyone else got a rulebook you missed, this conversation is a friendly way to decide what you’re building before you build more of it.
From the Basement
Doug reveals that Mrs. Neighbor Doug exists, which stuns everyone in mom’s basement, and then explains why Joe’s mom’s negotiating style involves a threat to cancel the shrimp appetizer at The Sizzler. Joe also shares a story about a rare Venetian grape that only thrives because of stress.
Resources Mentioned
Corinne Low at Wharton: faculty page with her research
Having It All: What Data Tells Us About Women’s Lives and Getting the Most Out of Yours: Corinne Low’s book, in paperback
“Collateralized Marriage” and “Winning the Bread and Baking It Too”: two of her research papers discussed in the interview

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Some of the best money moves of the year come with a deadline most people never notice. A student loan rate can drop by a full percentage point with one setup step. A window may be open to move retirement money with little or no tax. A gap in your income protection can sit unnoticed until a claim gets denied. Joe Saul-Sehy and guest co-host Anna Allem, CFP, sort the urgent from the merely interesting, using a caller’s real insurance dilemma, a family college decision, and a ringside look at the market’s worst Mondays. It takes a free hour before the calendar flips and no finance degree.
What You’ll Walk Away With
The deadline that got pushed back, and the one setup step that trims a student loan rate by a full point
Why one point off a rate is a bigger win than it sounds
What to check first if your repayment plan changed without you doing anything
A simple way to show a student what a college choice will cost after graduation, using real salary data
The question one family asked a kid before agreeing to the pricier school
Why a year-end Roth conversion deserves a look from some savers, and the Medicare premium surprise to understand before you try it
What an insurer does when a condition is already on your record, and why shopping around won’t change it
How to map the “crater” a lost income would leave, and when that math says you can skip the policy
The employer route that can quietly solve a coverage problem
Which of three famous Black Mondays hit hardest, and when a mutual fund trade really happens
A starting point for someone new to saving, military families included, that begins small
Why This Matters Now
Year-end is when quiet deadlines pile up and good intentions slip. You don’t need to master everything on the list. You need to know which items are time-sensitive, which can wait, and which you can cross off. If you worry about making a move you can’t undo, or feel behind because you haven’t looked at your plan lately, this is a low-pressure way to catch up.
From the Basement
Doug turns the trivia into a title bout, with boxing legends and a bowl of queso that did not survive the match. He also makes a Trans Am joke that nobody else in mom’s basement gets.
Resources Mentioned
Education Department Extends 1% Student Loan Auto-Pay Cut: The College Investor on the extended deadline
Stacking Benjamins Guides: HR and benefits, college planning, and taxes
Occupational Outlook Handbook: Bureau of Labor Statistics salary and job data for comparing majors
The MILMO Show: Lacey Langford’s podcast on money for military families
Get a Financial Life by Beth Kobliner and The Simple Path to Wealth by JL Collins: the two books recommended for new savers
Ask a question for the show

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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ask a room of young adults what they want most from life and about eight in ten will say “get rich.” The longest scientific study of adult life, now following the children of its original participants, found something different about what pays off. Dr. Robert Waldinger leads the Harvard Study of Adult Development, and he explains why one kind of spending keeps making people happier long after a flashy purchase fades, why career achievement doesn’t predict a good life, and the habit he now treats the way he treats the gym. Along the way come a rundown of what SECURE 2.0 changed and a listener question about saving for retirement from overseas.
What You’ll Walk Away With
What a generation named as its top life goal, and what the data says about chasing it
The kind of discretionary spending that keeps paying off in happiness, and the kind that doesn’t
Where money really moves the needle on wellbeing, and the point where it stops
Why “happiness” is the wrong target, and what the researcher measures instead
What a couple from one of Boston’s poorest neighborhoods can teach about a rich life
Why introverts aren’t at a disadvantage, and whether purposeful friendships beat casual ones
The subway experiment: why strangers who were told to talk ended up happier than they predicted
“Social fitness”: the weekly habit that works like exercise
A quick gratitude exercise for a bad mood, built around one question: what if I hadn’t had this?
Why money you’ve set aside is retirement money even if the account doesn’t say so

Why This Matters Now
Most of us keep score with a number. Waldinger’s research points to a more useful scoreboard: who shows up when it matters and whether your days have a purpose. If you’re saving diligently and quietly wondering whether you’re chasing the wrong things, or you feel behind every time you scroll past someone else’s highlight reel, this is permission to build the plan and the life at the same time, not one after the other.
From the Basement
This one comes out of the basement vault for Greatest Hits week. Doug’s trivia is about the first photograph ever taken of a person, a Paris street so busy that only two men holding still, a customer and a shoe shiner, made it into the picture. OG is also accused of being a curmudgeon, and he does not enjoy it.
Resources Mentioned
Robert Waldinger: Dr. Waldinger’s site and TEDx talk
The Good Life: Lessons from the World’s Longest Scientific Study of Happiness: the book by Waldinger and Marc Schulz
Lifespan Research Foundation: the nonprofit Waldinger co-founded, with more on the study

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