How Your Pay Grows: Raises, Promotions, and Changing Jobs
In this episode of Money Lessons, Andy takes up the three ways your pay grows — a raise, a promotion, and a new job — and the one lesson that runs through all three: starting pay is the base every raise after it is applied to.
He clears up the difference between a merit increase and a cost-of-living adjustment, explains why a promotion usually pays more than a raise, and puts numbers on changing jobs with the Atlanta Fed's Wage Growth Tracker, including the stretch in 2025 when people who stayed put saw more wage growth than people who moved.
He tells the story of asking his mentor and boss, the late Roger Leithold, for a raise at 22 — and the four words Roger gave him instead. He closes with the fourteen states that now require a pay range in every job posting.
Staying Relevant: Treating a New Skill as an Investment
In this episode of Money Lessons, Andy treats a new skill the way he'd treat any other investment: what it costs, what it returns, and when to make it.
He defines skill gap, upskilling, and reskilling; explains why skills go stale, with the World Economic Forum's finding that workers can expect 39 percent of their skills to be transformed or outdated by 2030; and works through a $3,000 certificate step by step, counting the money, the hours, and the years the skill will keep earning.
Fun fact: an employer with an educational-assistance plan can pay up to $5,250 a year toward your education — or, since the 2025 tax law, your student loans — with no tax on it.
Purpose at Work: What a Job That Doesn't Fit Costs You
In this episode of Money Lessons, Andy asks whether the work you're paid for fits the purpose you have — and what it costs you when it doesn't.
He defines purpose, alignment, misalignment, and golden handcuffs, then prices misalignment three ways in dollars: disengagement that lets your skills fade, golden handcuffs that make leaving a calculation instead of a feeling, and drift that keeps your human capital from growing.
Gallup's newest numbers are here, including the fun fact that low engagement cost the world economy about $10 trillion in 2025.
Human Capital: Your Earning Power Is Your Biggest Asset
In this episode of Money Lessons, Andy turns from what you earn this year to what you can earn over a working life.
He defines human capital — the competence, experience, and health an employer or customer will pay for — and measures it against the asset most families count as their largest, home equity.
Drawing on the Federal Reserve's survey of family finances, Georgetown's lifetime-earnings estimates, and the World Bank's wealth accounts, he shows why earning power is the largest asset most people will ever own, even though it never appears on a personal balance sheet.
He explains why a raise compounds the way investment returns do, why that makes skills built early worth more, and why only skills that last keep compounding.
Earning Without a Pay Stub: Self-Employment Tax, Estimated Payments, and the Side Gig
In this episode of Money Lessons, Andy turns to the earners the pay stub episodes left out: the self-employed, the independent contractor, and the side gig.
He defines the five terms that matter — self-employed, the 1099, net earnings, self-employment tax, and estimated payments — and works through the tax bill on the same $50,000 last week's employee earned, so listeners hear what happens when both halves of Social Security and Medicare land on the self employed.
A trip back to 1943 explains why the self-employed still pay the way every American once did, and why the IRS wants four payments a year instead of one. The episode closes with Andy's rule for anyone earning without a pay stub: set the tax money aside the day the payment arrives, and put the four dates on the calendar.
Benefits Are Pay: Total Compensation and the Employer Match
In this episode of Money Lessons, Andy adds up what a job is worth beyond the salary: the employer's share of the health premium, the employer's half of Social Security and Medicare, and the retirement match.
He follows one employee earning $50,000 and shows that total compensation comes to $63,100, and $750 less when a default contribution rate leaves half the match uncollected. Along the way he defines vesting, points to the one line on a W-2 that shows what your health coverage costs, and shares the Bureau of Labor Statistics finding that benefits are 30 percent of what private employers spend on pay.
Your Income Tax: Brackets, Withholding, and Your Refund
In this episode of Money Lessons, Andy explains how the federal income tax is calculated, starting with four definitions every taxpayer needs: taxable income, the tax bracket, the marginal rate, and the effective rate.
He works a single filer's 2026 tax one bracket at a time to show why someone in the 22 percent bracket pays about 13 percent, and why a raise never leaves you with less after tax.
From there he explains how an employer estimates withholding every payday, why a refund is your own money coming back without interest, and how the Form W-4 lets you change that estimate at any time.
Special Edition: Forty Trillion Dollars — What the National Debt Means for Your Household
In this special edition of Money Lessons, Andy takes the national debt's crossing of forty trillion dollars on August 18 and explains what the number is made of — the debt held by the public, and the money the federal government owes its own trust funds.
He shows why interest now takes eighteen and a half cents of every dollar the government collects, and why "we'll grow our way out" and "inflation will take care of it" are the same answer. Ray Dalio's three-percent deficit target anchors the arithmetic, and the 2026 Trustees Reports show where the pressure lands next.
Andy closes with what the debt means for your mortgage, your savings, and your benefits across three time horizons, and what you can do about it through three of the six jobs your money has.
Anatomy of a Pay Stub: The Deductions You Chose, the Ones You Didn't, and the Pay You Never See
In this episode of Money Lessons, Andy reads a pay stub for the lines most people skip past.
He sorts every deduction into two types — the ones the law requires and the ones you elected, usually in the paperwork on your first day — and explains why a health premium, an HSA, and a retirement contribution come out of your pay before your taxes are figured, and why the federal taxes don't all treat those deductions the same way.
Along the way he clears up the most common misunderstanding on the stub: the Social Security line is a tax paid to today's retirees, not a deposit into an account with your name on it, and the story of the first person ever to collect a monthly check shows why.
He closes on the pay that never appears on the stub at all — the employer's share of the premium and the retirement match — and why two jobs with the same salary can pay very different amounts.
Nudge and Sludge: The Vocabulary of Everyday Money Decisions
In this episode of Money Lessons, Andy supplies the vocabulary behind three weeks of teaching on habits, defaults, and friction.
Herbert Simon — who was never an economist — challenged his era's assumption that buyers decide with complete information, and won a Nobel Prize for finding those limits inside companies before anyone thought to look for them in customers.
Richard Thaler named the arrangement of options in front of you choice architecture, and a decade after publishing Nudge with Cass Sunstein, he coined sludge for friction pointed at the person who has to get through it.
Defaults and Friction: The Money Machinery Someone Else Built for You
In this episode of Money Lessons, Andy turns from the money machinery listeners build themselves to the machinery that gets installed before they arrive.
He starts with the default — what happens if you do nothing — and shows how much of a household's money moves according to settings that somebody at a company chose in advance. The workplace retirement plan serves as the rare example of a default that works in the saver's favor, along with a caution that plenty of employers are still exempt from it.
From there he takes up friction, the effort standing between wanting something and having it, and traces how the same business will strip every step out of a purchase and then build steps into the exit.
The Same Old Songs: What Musical Taste Reveals About Financial Change
In this special edition of Money Lessons, Andy takes on a question that sits underneath most of personal finance: why change is so hard.
A complaint about his band's setlist leads to the research on why musical taste is set around age fourteen — and to the study showing that appetite for financial risk locks in the same way, set by whatever the markets were doing when a person first had money in play.
Neither one was a decision. Both feel like one.