Your Money Guide on the Side

Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠⁠tylergardner.com/book⁠⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st!

And as always, a MASSIVE thank you to this week's sponsors:

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A spreadsheet can tell you which decision might leave you richer. It’s less useful at explaining why you still want to pay off the house.

In this episode, Tyler explores five money questions whose answers depend on values and obligations as much as arithmetic. Starting with a client whose priorities he once misunderstood, he examines the tension between building wealth and building a life, including his own habit of saving for a future that keeps getting preferential treatment.

You’ll learn:

Why paying off a mortgage can answer a different question from maximising returns.

How your relationship with your future self can encourage both saving and excessive sacrifice.

Why support for adult children needs a clear purpose and an agreed endpoint.

How family conversations about inheritance can address expectations before surprises arrive.

Why “enough” keeps moving when it’s attached only to a number.

Better decisions begin with what the money is for—and an honest answer about the life it should support.

If this episode helped, please consider leaving a review on Apple or Spotify.

Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠⁠tylergardner.com/book⁠⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st!

And as always, a MASSIVE thank you to this week's sponsors:

DeleteMe⁠ → joindeleteme.com/tyler20⁠ Use code Tyler20 for up to 20% off!

Facet⁠ → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer!

⁠Copilot Money⁠ → ⁠www.copilot.money/tyler⁠ — use code TYLER2 for two free months.

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And on to the show notes!!

You’ve reached your retirement number. Now what’s going to get you out of bed on Monday? A healthy account balance can fund your freedom, but it can’t give your days a shape.

In this episode, Tyler explores five needs behind a happy retirement: autonomy, relatedness, competence, desire and marked time. Drawing on psychological research and his own experience, he asks what happens when work stops supplying the people, progress and structure you barely noticed it provided. Even the colleague you found irritating may have been doing you some good.

You’ll learn:

Why autonomy means choosing worthwhile obligations, rather than having none.

How everyday acquaintances provide connection your closest relationships can’t replace.

Why getting better at something matters more than already being good.

How an unfinished bucket list keeps anticipation alive.

Why distinct experiences and annual rituals help make the years memorable.

Build the life your money makes possible before your last working Monday arrives.

If this episode gave you something to think about, please consider leaving a review on Apple or Spotify.

Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠⁠tylergardner.com/book⁠⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st!

And as always, a MASSIVE thank you to this week's sponsors:

Thrive Market⁠ → Use link thrivemarket.com/tyler to get $30 off your first two orders. You cannot get this deal on the website — it's only through my link. And that right there covers your membership fee, so sign up now before this exclusive offer ends.

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Gelt → ⁠⁠joingelt.com/tyler⁠ because Q2 is where strategic businesses make game-changing tax moves. If you're a business or a high-net worth individual, you might want to check this one out today.

And on to the show notes!!

The “safe” part of a portfolio can still deliver a nasty surprise. Bonds have a job to do, but protecting against everything isn’t in the contract.

In this episode, Tyler revisits his earlier argument against bonds with a sharper distinction between growth and ballast. He explores what fixed income actually protects, what it leaves exposed, and when certainty matters more than chasing a higher return.

You’ll learn:

How interest rates, inflation and opportunity cost challenge the idea that bonds are automatically safe.

Why a bond fund is not a bond, and what duration reveals about potential price swings.

The different jobs money markets, bond funds and TIPS can perform.

When matching maturities to expenses and holding a retirement spending buffer make sense.

Why pensions and other steady income belong in your whole financial picture.

The useful question is safe from what? Judge each holding by the job it needs to do, rather than a reassuring label.

If this episode helped, please consider leaving a review on Apple or Spotify.

Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠⁠tylergardner.com/book⁠⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st!

And as always, a MASSIVE thank you to this week's sponsors:

Bilt → ⁠⁠joinbilt.com/tyler⁠⁠ So you can choose the card that fits your lifestyle without missing out on points and exclusive benefits.

Fabric → ⁠⁠meetfabric.com/tyler⁠⁠ Made for busy parents like you; all online, on your schedule, right from your couch. You could be covered in under 10 minutes, often with no health exam required.

LMNT → ⁠drinklmnt.com/tyler⁠ Get a free 8-count Sample Pack of LMNT’s most popular drink mix flavors with any purchase at drinklmnt.com/tyler.

Facet → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer!

And on to the show notes!!

Most of the biggest money questions aren’t really about what to buy. They’re about how to think when the answer isn’t obvious.

In this episode, Tyler answers the five questions listeners have asked most in 2026 — from pensions and politics to healthcare, market concentration, and long-term care — with an emphasis on what you can actually control.

You’ll learn:

How a pension and Social Security can change the way you think about portfolio risk

Why being right about markets or politics still doesn’t mean you can time them

How the return of the ACA subsidy cliff changes early-retirement planning

What today’s S&P 500 concentration does — and doesn’t — tell you

The four main ways to prepare for long-term care, including the risks of each

The recurring lesson is that good planning rarely comes from predicting the future. It comes from understanding the whole picture, knowing what you own, and preparing for the decisions you can control.

If the show’s been helpful, please consider leaving a review on Apple or Spotify.

Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠⁠tylergardner.com/book and be eligible for all monthly incentives between now and December 1st!

And as always, a MASSIVE thank you to this week's sponsors:

Momentous⁠ → ⁠⁠livemomentous.com⁠ Use code Tyler for up to 35% off your first order!

Gelt → ⁠⁠joingelt.com/tyler⁠ because Q2 is where strategic businesses make game-changing tax moves. If you're a business or a high-net worth individual, you might want to check this one out today.

Caldera+ Lab⁠ → If you've been meaning to take better care of your skin, head to CalderaLab.com/TYLER and use code TYLER for 20% off your first order.

And on to the show notes!!

Most people spend decades learning how to make and save money.

Far fewer learn how to spend it well.

In this episode, Tyler shares two very personal lists: five things he’ll happily overpay for, and five things he refuses to spend money on again.

Not because one list is objectively right.

Because the point is figuring out your own list.

In this episode, Tyler covers:

Why many well-funded retirees still struggle to give themselves permission to spend

Five things Tyler believes are genuinely worth the money, from generous tipping to buying back time

Why a capsule wardrobe, books, house cleaning, and even leasing a car can make sense when they solve the right problem

Five purchases he’s done with—including short-haul first class, expensive wine, and other versions of “luxury” that don’t actually improve his life

Why outsourcing tasks you hate can increase happiness—but outsourcing things you enjoy can do the opposite

How to separate spending that buys time, health, peace, or connection from spending that mostly buys an audience

The exercise of building your own “worth it” and “never again” lists

The core idea:

The money was never the finish line. It’s a tool for buying more of what you already value.

Spend generously where it meaningfully improves your life.

And stop paying for things you only thought you were supposed to want.

If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps.

Hope this gives you something to think about this week.