How To Be A Rich Old Lady

January 12, 2026

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For the next 3 weeks, friend of TFD and investing expert, Amanda Holden will be taking over our newsletter in celebration of her new book, How To Be A Rich Old Lady. We’re excited to have Amanda share her expertise with our community, and even more excited that she’ll be hosting our next Society workshop on January 22nd [full details to come later this week]!

And, as always, make sure to read through the entire newsletter so you don't miss anything! Thank you for being a part of this special little corner of our community!

❤️ TFD

By Amanda Holden

Hello, TFD Readers! 

I’m Amanda Holden (you may know me as @dumpster.doggy) and it has been a great joy to teach many of TFD’s investing workshops and courses over the years. And I am beyond excited to share with you my book publishing tomorrow (!!!), called How to Be a Rich Old Lady.

In the book, I am up-front about my goal: I want you to achieve financial independence.

Those two magic words get thrown around a lot, so let’s be clear about what I mean. For women especially, financial independence is often interpreted as not relying on a man or partner for money. It is a form of financial independence I ask that you take seriously, especially right now. In the investing world, though, financial independence has a somewhat different meaning: not needing to rely on a job for money. It means having enough invested that the income your investments generate can cover your spending.

Back in Grandpappy’s day, retirement was tied to an age. Many workers (but certainly not all) labored until sixty, collected a pension, and lived out their golden years. That world is gone. With the death of the company pension and the ongoing assaults on Social Security, retirement timing is no longer dictated by age — it’s dictated by how much and how well you invest. You’ll retire when you have enough money to retire. It all depends on your investments.

For what it’s worth, I don’t think it should be this way. I fight for collective solutions and believe every person deserves to retire. But, I also come from the gatekept world of finance where I observed something very peculiar: Every single one of my wealthy clients, with these big, life-sustaining portfolios? They were all men. It was men who enjoyed the agency, security, and options that flexible wealth brings. And I wasn’t having that — it’s why I wrote this book. 

And with that, here are four steps you can take to meet your Rich Old Lady.

#1: Visionboard your Rich Old Lady

First, I ask you to summon your inner Rich Old Lady. I know what you’re picturing: a crusty old broad in a big hat being mean to the waiter at the country club. That’s not what this is. (Well, except for the big hat.)

Being a Rich Old Lady is about the freedom to imagine a future that is wild, weird, and uniquely you. Maybe it’s quitting your tech job at fifty to run a sanctuary for rescued farm animals with your three best friends. Maybe you’re the grandma who’s neighborhood-famous for both her cheesecake and her right bicep, still beating guys at arm wrestling at sixty-five. Maybe, for your eightieth birthday, you’re going naked rollerblading down the Venice Beach Boardwalk. 

No, really — do it! Picture her! Where does she live? Who is she with? What does she spend her days doing? Write it down. Say it out loud. Don’t be scared of what you want.

My Rich Old Lady is an artist, never without her statement cane (I have bad knees). Financial independence allows her to stay in New York City while doing low-paid work that matters to her, like advocating for labor rights. But sometimes she throws on her most obnoxious jewelry and jets off to Italy to meet up with her significantly younger lover to slurp down the business end of spaghetti noodle, Lady-and-the-Tramp–style. But mostly, she’s laughing with her friends, because that’s the whole point. 

To be a Rich Old Lady is to be rich in life, options, experiences, and especially love. Nothing is more important in life than our relationships — and I want you to have plenty of time for yours. Your people won’t be here forever, after all. Neither will you. 

#2: Build your financial foundation

Our success in personal finance really comes down to one thing: what I call The Gap.

The Gap is the space between what you earn and what you spend. It’s the money left over after your bills are paid. And this surplus is the single most important financial tool you have. The Gap is where the magical shit happens. The Gap represents your financial possibility. The Gap is what allows you to save, pay down debt, and invest. The Gap buys the investments that will someday pay for your electricity bill and that Eurotrip with your bestie when you’re 70. 

If you don’t have a Gap — for example, if you’re overdrawing your checking account or watching your credit card balance creep up — that’s okay! But it does tell us exactly where we need to start. We can increase our gap by (1) decreasing our spending, (2) increasing our income, and (3) both. 

Once you have a Gap, hell yes. Let’s put that Gap to work. The first order of business is to use your Gap as a tool to build your financial foundation. And for most people, a financial foundation consists of (1) saving an emergency fund and (2) paying off high-interest debt. 

#3 Integrate retirement investing 

Savings alone don’t keep up with inflation. Investing lets you end up with more than you put in — even after rising costs are accounted for. Investing is what gives you a real shot at covering the biggest expense of your life: living for decades without a paycheck.

Consider how much it costs to live for one year. Now multiply that by twenty or thirty. (Add your custom zebra-print Rollerblades to that and that number is getting big!) Many of us will live into our nineties, and I was sent here by your future self to remind you of this.

Get started with whatever amount you can. Compound returns reward time more than any other factor. The job of saving enough for retirement is scary, but here’s a reframing I like: hopefully it’s the biggest expense of my lifetime! Hopefully we get twenty-plus years off the clock with our Rich Old Lady biker gang, wind in our grays.

#4 Keep learning, but don’t forget to live

Money can be very painful. It’s the ache of uncertainty; the fear that you’ll never get it right. And here’s the thing: you might not figure it all out. You might never feel like you’ve “won” at money. And that’s okay.

If you postpone living your life until you feel good about your finances, you risk not only your joy now but the future joy you’re purportedly working toward. You don’t need to reach any financial milestone to enjoy your year, or to take note of the sheer metaphysical wonder that is being you, and being alive. Nor do you need a maxed-out retirement account to be a good neighbor or parent to enjoy the rush of laughter between friends. (Your community, too, can be thought of as a source of wealth.) 

And anyway, being a Rich Old Lady is about more than just investing money for the (admittedly tenuous) long term. It is about gifting yourself the psychological relief of knowing you’re doing what you can, right now.

Yes, take the next step. Continue learning — perhaps especially about investing, as this skill will directly translate into better and more options. But also, don’t wait until you know everything — because that will never happen. Invest, yes. But don’t forget to live.

Let’s be rich old ladies together!

— Amanda

If you would like to learn more about investing and building wealth from Amanda, How to Be a Rich Old Lady is an essential step-by-step roadmap to financial independence.

A reminder as we are currently in peak ~financial goals~ season, this is what we here at TFD personally endorse and use ourselves to reach all of our financial goals!

FINANCIAL ADVISORY — Advisor.com: Dozens of people in the TFD community already trust and use Advisor! They’re one of the only financial advisory companies offering their services for a fixed, flat annual fee. Their team of advisors work for you, not commissions, and help you to achieve your financial goals through planning, investing, and more, no matter where you’re starting from.

INVESTING — Betterment: If you’ve been wanting to start investing but feel overwhelmed by where to begin, Betterment makes it super simple—even if you’re not a financial expert. With automated investing and goal-based planning tools, they’ll help you grow your money responsibly and sustainably over time. It’s a great option if you want to take control of your financial future without having to become a full-time market expert.

BUDGETING — Monarch: Our recommended Mint replacement! As we already shared in the main section of this newsletter, we highly recommend using Monarch to take the guesswork out of managing your money — use it to budget, set goals, and actually understand where your money’s going. Even better: there’s no ads, no selling your financial data to third parties, and no "premium only" upsells — just a clean, secure app that makes managing money feel way less overwhelming (and actually kinda fun?).

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