Copilot Money vs. Mint

While I was always a Mint purist (“And if it doesn’t work for you, you’re just not trying hard enough!” I’d say when people would tell me it just wasn’t working), the more my recommendation was met with hesitancy, the more I felt compelled to find a solution for budgeting that would do for spending what Betterment did for investing. I was on the hunt.

My friend Richard is a quintessential Silicon Valley tech buff (a 2x start-up founder, no less), and when I told him about Money with Katie, the first thing he said was: “Cool! Have you ever heard about Copilot? All my friends love it. The UI is fantastic—one of the founders was a software engineer at Google.”

I downloaded it so quickly, my App Store almost crashed. Then I saw it: the price.

“Aw, man. This costs money? Shit. Never mind.”

But I noticed the demo mode, and it was enough to pique my interest. I played around with the dummy data and immediately felt envious. Then, a few months passed, and curiosity finally got the best of me. I didn’t want Copilot Money to be the one that got away.

Now, five years later, I’m especially glad I didn’t let my cheapness get the best of me. Not to brag, but I’ve categorized 7,121 transactions (more on that below) since I began using Copilot Money in 2020:

And, as longtime budget freaks will know, Intuit shuttered Mint at the end of 2023.

How to budget, generally

While it may be obvious, I want to make sure we’re on the same page here: I don’t use the budgeting app to decide what my budget should be (though Copilot Money will analyze your spending and give you accurate estimates for each category, including recommendations about how you should reallocate funds based on your actual behavior).

I used my Wealth Planner to make my spending and investing plan for the year, and then simply create identical groups and subcategories in Copilot Money so the app will automatically track my every transaction. (Doing this manually would be nightmarish, as I have a metric shit-ton of credit cards and accounts, as pictured below.)

You could definitely create and manage your budget all in one place using Copilot Money, but I like to have my own records as well. At the end of the month, I record the category totals in my Wealth Planner for accountability and record-keeping. The Wealth Planner is built to give you end-of-month and end-of-year summaries, because data is sexy and makes you rich. Obviously.

The system, when working together, might look something like this. On the left, you’ll see my high-level goals for food spending in my big financial plan in the Wealth Planner, and on the right, you’ll see every restaurant transaction being captured.

A Quick Guide to Copilot Money Transactions

The software is very smart and can generally tell with ease what a transaction is—whether it’s a regular expense, income, an internal transfer (like when your checking account pays off your credit card bill; that’s money that’s already been accounted for as ‘spent’ by the credit card transactions), or a recurring bill.

• “T” — If you see a little “T” inside a square next to the transaction, that was an “Internal Transfer.” You moved money from one account to another.
• “I” — Income. This is interest earned, income earned, or else other money that came in that the software recognizes as net-new.
• “R” — Recurring bill (more on how to set those up below).

You can also Exclude purchases from being counted, which I do with business expenses. (Just tap the transaction itself, which will open a little drawer where you can see details—tap the Category, and on the far left, you’ll see “Exclude” as an option. If you choose that, it’ll vanish. If only actual spending were that easy.)

How to Set Up Your Copilot Money App

I had heard Copilot Money was really “smart”; that it was a budgeting app that understood real life.

But I have to admit, when I first started syncing all of my accounts (which, by the way, were all available in the app with the exception of my obscure HSA fund), I was a little overwhelmed. Months of unrefined data poured in, and I had a brief moment of panic: As someone who checked, categorized, and combed through her Mint data multiple times a day, seeing the last year of my life begin to populate willy-nilly in the app freaked me out and I almost aborted the mission.

I’m so glad I didn’t.

The first thing that I had to do (after syncing my accounts) was begin correcting or approving Copilot’s estimates. Most of them were freakishly spot-on, but some of them required additional tweaking on my part. I noticed that normally happened for categories where I paid for something and then got reimbursed for someone else’s half (think utilities, groceries, rent, etc.). The estimate would guess double my actual out-of-pocket cost because the transactions themselves were twice as big.

Because I had already built my overall spending plan into my Wealth Planner, setting it up in Copilot was as easy as adding new spending Categories (and grouping them). Here’s what some of mine look like now after many iterations, as of December 2025:

Copilot Money’s Venmo Integration

The good news? If you’re someone who gets reimbursed via apps like Venmo a lot, you can connect your Venmo account so transaction names and amounts will populate like they would in any other account. (Here are some FAQs about how the Venmo integration works; the TL;DR is that you set up email forwarding for Venmo receipts within the Copilot app and that’s how it pulls the data in.)

Recurring Transactions

Another nice feature is “Recurring Transactions,” which analyzes your data to determine (a) what your recurring charges are and (b) when they happen. Then, it builds it into your spending already at the beginning of the month as if the money has already been spent—that way you don’t go on your merry way through your month thinking you’re hella under-budget only to be surprised by your $160 electric bill on the 21st and blow your own lead.

While setting the actual budget amounts and making sure all the Recurring charges took a little time (probably about half an hour), I’ve been really impressed at how easy it’s been to keep up with and how little ongoing effort it takes. Each Recurring Transaction gets marked with a little “R” in the app. The only Recurring Transaction I use currently is for my rent payment, which happens on the 1st of the month:

Something silly that I’ll admit I loved about Copilot Money: Personalization

You can change category names, colors, and emojis really easily. And while it’s silly to admit, I really liked that aspect of the personalization. Everything works the way you expect it to: Want to change something? Just tap it. Options pop up. It’s not hard to operate, which is crucial for an app that facilitates something as painful for some as budgeting. There’s a level of whimsy to the product and nice haptic feedback (when you tap something, you get a gentle jolt of recognition) that makes regular use of this app a joy.

After You’ve Set Up Your Copilot Money App

Understanding the Tabs You Swipe Between

I quickly got to know the major sections of the app because they make really good use of all the real estate. You can move them around based on what you use most often, and my lineup is currently:

• Cash flow, where you’ll see your net income for the year (super addictive to check, if you’re a psycho like me), which you can easily compare to years prior
• Dashboard, which I’d consider the homebase, where you can see a visual for your spending month-to-date, your budget overview (overages are highlighted here), upcoming recurring payments, and income to date — this is where all new transactions that need to be reviewed will appear, so you’ll probably spend most of your time there
• Categories, which is where your budget categories are listed and the “Spent” amount is tracked against the budgeted amount
• Accounts, where you’ll see all your synced accounts and your assets and debt — this is also where you’ll see your net worth at a bird’s eye view
• Investments, where you’ll see your investment holdings by ticker — the cool thing about the “holdings” section of the Investments tab is that if you own the same security across five accounts, it’ll aggregate your total equity here (pictured below)
• Transactions, where it tracks each and every transaction in a simple ledger
• Recurrings, which we’ve already discussed
• Goals, which is actually a feature I haven’t personally used much because my savings goals are automated in my Wealth Planner and I don’t really think about them anymore

And because you pay for Copilot Money, they don’t have to advertise to you—so every section of their app is actually useful and “real,” with no noise from sponsors or ads.

How to Use Copilot Money in an Ongoing Way: iOS, MacOS, iPadOS, and Web

I might be a unique case study since I f***ing love tracking my spending, but I use Copilot like it’s Instagram now. I’m in that shit constantly. I checked my screen time report, and it’s consistently clocking in as one of my top 5. What can I say? I told you I liked data!

When you open the app, it pulls up the dashboard and highlights transactions that have happened since you last logged in, organized by day. You can click “Mark as Reviewed” to let the app know you’ve signed off on them. It’s pretty slick. I’d guess that about 20% of the time, I have to recategorize the transaction, but that takes all of 8 seconds to click the category and select a new one.

Copilot Money is available on…

• iPhone (where I use it most)
• iPad
• Mac (if I’m sitting down to update my Wealth Planner at the end of the month, I’ll usually use the desktop app since it’s bigger and you can see more at once)
• And, recently, web!

That’s something I appreciate about their team: They push new features thoughtfully, and when I get a notification something new is coming, I know they’re going to overdeliver.

Smart-Rebalancing of Your Budget: Why Copilot Money is Good for Beginners & People New to Budgeting

Let’s say you’re relatively new to the magical world of personal finance and you’re still getting your arms around what your typical spending looks like. The Rebalancing feature essentially uses your actual behavior to determine the most optimal way to shift your budgets, but without changing the total amount spent. It reallocates the dollars to the categories where you’re actually spending money, which improves accuracy over time.

To have Copilot Money rebalance for you, just tap the little magic wand icon in the lower righthand corner of the “Categories” tab, and you’ll see what it suggests based on your spending that month:

Notifications

I’m a freak about notifications most of the time (I turn most of them off), but with banking apps, I’m really paranoid ever since my identity was stolen in 2019. Copilot’s notifications will alert you to any suspected fraud activity right away. I went ahead and gave them full permission to send me whatever they wanted. Blow me up, Copilot. Give me your worst.

It was a “green checkmark” spree as I went through my notifications settings, and I’ve been pleasantly surprised at how respectful the notifications are—I actually don’t feel like I’m getting blown up at all. I tried to go back in my Notification Center to screenshot a sampling, and there weren’t any there…because I’ve clicked on every single one. Clearly, even in the fugue state in which I typically use my phone, I’m entranced enough with the notifications that I engage with them.

Usually, they pertain to spending updates, categorizing new transactions, or letting you know you got #paid.

Is Copilot Money Worth the Cost?

All right, people. Back to the elephant in the room. The original reason I was almost #out on Copilot Money was because it costs money. It’s $13 per month (or, as college Katie would say, two burrito bowls) if you subscribe monthly, or $7.92 per month if you subscribe for the year upfront.

Because I’m a #moneyblogger, I decided upfront it was market research (and therefore a #BusinessExpense! Thanks, IRS). But after using it, I wholeheartedly believe it’s worth the expense, especially if it finally gets you to interact with your spending and track your budgets on a regular basis.

Try Copilot Money for free—use the code KATIE2M at checkout to extend your free trial to two full months, so you can take it for a true test run, free of charge.

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Copilot Money has been a sponsor of the Money with Katie newsletter in the past. They had no input in this particular blog post or the opinions expressed herein.

As I was reminded repeatedly by TurboTax’s 2023 ad campaign called “Don’t Do Your Taxes,” most people would rather scale an icy mountain than file their taxes.

While I absolutely used to feel that way, too, I’ve come to love tax season as a time for reflecting on my financial progress, collecting forms like rare Pokémon, and poking around my tax software of choice, TaxAct (not a sponsor, but you should be!), for deductions I didn’t realize I qualified for. (The part where the software tells me I owe tens of thousands of dollars is my least favorite part, but it’s decidedly fun up until that point!)

So, we’re discussing three ways to lower your tax bill that I’ll highlight below, but I also wanted to cover a few bizarre forms you may encounter when you begin dabbling in the world of deductible contributions to qualified retirement plans. (This won’t be exhaustive, but they’re items Henah or I have personally come across after implementing our own strategies.) It can be scary the first time you hit a speed bump in the tax software that’s like, “Yo, you may have screwed this up!” 

Now, depending on how you earn and your access to retirement accounts and certain healthcare plans, it’s possible that all three of the options we cover today will be viable for you, but they all have one thing in common: 

They’re all legal ways to hold on to more of your income, instead of forking it over.

Crucially, these vehicles allow contributions made this year—in 2025—to be characterized as though they were made last year, in 2024. And at the risk of stating the painfully obvious: To take advantage of this, you have to have the cash available to invest. 

Which tax year should you select when making contributions in 2025 for 2024?

When you’re contributing to these investment accounts, they’re going to ask you which contribution year you’re electing. If you’re trying to ease your 2024 tax burden, be sure to select 2024! If you choose 2025, it’ll apply the contribution to next year’s tax bill.

The Traditional IRA and a few related fun formz

If you (and your spouse, if you have one) are not covered by employer-sponsored retirement plans at work (read: a 401(k) or 403(b), most likely), you can each contribute up to $7,000 to your own Traditional IRAs for the 2024 tax season. 

That’s up to $14,000 you can wipe right off the top of your taxable income, if both partners contribute the full amount to their respective IRAs.

A minor point of clarification for couples with combined finances: These are intended to be individual retirement accounts, so there’s no such thing as a “joint” IRA.

How do I calculate the tax savings I’ll score from contributing to the Traditional IRA?

For example, if you and your spouse are in the 24% marginal tax bracket after other deductions and you both contribute the maximum allowed, that’s a joint tax savings of approximately $3,360 (a calculation we arrive at by multiplying our contribution, $14,000, by our marginal tax rate, 24%). 

This means if you owed the IRS, say, $1,500, this one move would wipe out that tax liability, and probably generate a refund, too.

But here’s how your income may thwart your plan to deduct your contributions

Straight from the mouths of our boiz of the IRC, here are a few income limits and phaseout scenarios to be aware of for the 2024 tax season:

If you ARE covered by a workplace retirement plan…

• A single taxpayer (or head of household) begins to phase out of being able to take a deduction for their contribution when their MAGI (Modified Adjusted Gross Income) exceeds $77,000, and is totally ineligible for a deduction once they earn more than $87,000

• A married couple filing jointly begins to phase out of being able to deduct their contribution when their MAGI (We Three Kings, baby!) exceeds $123,000, and is totally ineligible for that sweet, sweet deduction once they earn more than $143,000 

If you are NOT covered by a workplace retirement plan, but your spouse is…

• A married couple filing jointly, where you are not covered by a workplace plan (but your spouse is!) begins to phase out at a MAGI of $230,000 and is totally ineligible once MAGI exceeds $240,000

And if you’re married filing separately, good luck—you can’t earn more than $10,000. (I know, I don’t get it, either.)

When this won’t work

To put a finer point on this one, this can only be leveraged to the hilt if you both aren’t covered by retirement plans at work. 

Also note that you’re only allowed to contribute a maximum of $7,000 across your Traditional and Roth IRAs, so this won’t work if you’ve already contributed the maximum for 2024 (even if you were contributing to a Roth IRA, not a Traditional—but if you contributed, say, $3,000 to a Roth IRA, you’d have $4,000 left that’s fair game to contribute to either). 

Fortunately, if you are covered by a plan at work and not eligible to consider a deductible Traditional IRA contribution, you can still contribute up to $7,000 to a Roth IRA (with some income limitations; here’s a video about how to get around those), though that won’t lower your taxes this year. 

You can open a Traditional or Roth IRA at pretty much all major brokerage firms; I prefer roboadvisors for ease of use (think Betterment, M1 Finance, etc.), but if you choose to take the DIY route, remember to invest the cash you contribute. I know way too many smart people who opened an IRA, funded it, and never invested the cash, so it just sat there…for years…uninvested. We have an episode about indices to consider when you’re building a diversified portfolio.

If you make excess deductible contributions, you’ll get prompted with a message (in TaxAct, at least!) that looks like this.

This screen grab is from the 2022 tax season.

Notice how TaxAct tells you what your maximum allowable deductible contribution is—in this case, the couple’s income, $213,789, was above the upper limit for a couple where both spouses are covered by plans at work in 2022. 

Form 8606 (I promise it’s not too scary)

All you need to do is file Form 8606, declaring that—oopsie daisy—you were totally just kidding, Uncle Sam, and your contributions were actually non-deductible all along! 

That looks like this: 

In this example, one individual in the couple accidentally contributed $2,400 to a Traditional IRA without realizing they couldn’t deduct the contributions. By classifying the entire amount as nondeductible, they’ve dodged the penalty bullet.

A quick jargon interlude: “Deduct” or “deductible” effectively translates to “wipe the amount off your taxable income as though it never happened.” Deductible contributions to pre-tax accounts are what allow us to save income tax in the present year. In this case, the couple became ineligible during the course of the year to deduct their Traditional IRA contributions, so the contributions become “non-deductible.” I.e., they’re no longer allowed to take the tax deduction.

So while you can easily fix excess deductible contributions by classifying them as “non-deductible,” you still won’t be able to deduct them (but they’re still tax-sheltered investments for the future, so all is not lost!).

And while we’re on the topic of Traditional IRAs, let’s talk about the 1099-R…

If you rolled over a 401(k) into an IRA in 2024, you received a form called the 1099-R. It’s a form your investment firm sends you whenever you take a distribution from a retirement account (yes, even a legal, unpenalized, run-of-the-mill rollover distribution!).

When I first received one a few years ago, I was convinced I was on a Pentagon watch list and had royally f***ed something up, but not to fear—this is a relatively straightforward declaration as well. 

For example, in the TaxAct software, in the “Income” section, you’ll see an option for “Taxable IRA Distributions.” When you click on it, you’ll have the option to add a 1099-R. If you fill out the form exactly, it should include a few things:

• The amount you rolled over

• The “code” for the rollover 

• The taxable amount (if it was just a direct rollover that didn’t change tax status, it should say $0.00)

…and that’s about it. Regardless of your rollover amounts, filing your 1099-Rs shouldn’t impact your tax bill, but you’ll still want to make sure you report ’em. The IRS is ~super serious~ about transparency, you know?

Next up: The SEP IRA

If you have any self-employment income (read: 1099 income), this last-minute Hail Mary might be a godsend. Side hustle girlies, #rejoice.

A few things to note:

• If you have a business with full-time employees, the rules are a little different; you have to contribute to their SEP IRAs, too, so if that’s your situation, you probably have a business CPA who can guide this choice—but if you’re just a solopreneur or side hustler, this is probably a fairly uncomplicated option for you. 

• You can contribute to a SEP IRA even if you’re also covered by, say, a 401(k) at a W-2 employer, since they’re accounts funded by two different sources of income.

The TL;DR on the SEP IRA for solopreneurs is that you can contribute up to 20% of your net business income, up to a whopping $69,000 for 2024. 

If you want to calculate a super precise contribution for the biggest deduction possible, you can always pay a CPA to do it for you—but a tax pro I befriended (yep, I love me some tax nerds) taught me a cool trick to make this a little easier. 

Since you deduct your self-employment taxes of 15.3% in order to get your “true” net business income on which the contribution is based, you can simply multiply your “self-employment income after write-offs” by 20%, rather than 25% (which is what you’ll see elsewhere online as the upper limit). This will give you a rough estimate of how much you can contribute to your SEP IRA.

So if your business earned $15,000 and you’re writing off $3,000 for expenses, leaving you with $12,000 of net business income before other deductions, you’d multiply $12,000 by 20%: You can contribute around $2,400 to your SEP IRA. 

For those with a lot of side hustle or self-employment income, this deduction can be quite significant.

When this won’t work

This won’t work if (a) none of your income came from self-employment or side hustle-type sources or (b) you’ve already contributed the maximum to a Solo/Individual 401(k). For the uninitiated, a Solo 401(k) is just a 401(k) you can open for yourself and use as a self-employed person. 

SEP IRA vs. Solo 401(k)

For example, if I had a Solo 401(k) in 2024 and I already contributed 20% of my net business income to it as “employer contributions,” I can’t then double-dip and contribute 20% more to a SEP IRA, too. 

If you had a Solo 401(k) but didn’t fund it, you could finish funding the Solo 401(k) (with “employer” contributions) in 2024 for the 2024 tax year. That’s totally fair game, too—no SEP IRA required.

The reason the SEP IRA is a more viable option for retroactive tax minimization? You can’t open a Solo 401(k) in 2025 and fund it for 2024. The Solo 401(k) has to be opened by Dec. 31, 2024 to be eligible for 2024 contributions. That’s why the SEP IRA is such a baller tool—you could have started a business in 2024, made absolutely no moves to invest in pre-tax self-employment vehicles, and decide on April 13, 2025 that you want to open and fund one for 2024.

You can generally open SEP IRAs at all major brokerage firms without much fuss; roboadvisors typically offer them as well.

Beware of a SEP IRA if you do the Backdoor Roth IRA (and one way around it)

One watchout: If you’re currently someone who dabbles in the Backdoor Roth IRA strategy because you’re over the Roth IRA income limit, you’ll want to weigh your priorities before opening a SEP IRA, as a SEP IRA “counts” as a Traditional, pre-tax IRA and will make executing a Backdoor Roth IRA more complicated. 

Sometimes, people opt for Solo 401(k)s instead for this reason. But if you’re down for a complicated workaround, you can open both a SEP IRA and a Solo 401(k) in 2025, fund the SEP IRA for 2024, and then—after you’ve filed and tax season is over—roll that shit over into your Solo 401(k) such that you have $0 balance in the SEP IRA again. Problem solved. Backdoor Roth IRA commence! Just note your business needs to be incorporated with an EIN number to open a Solo 401(k).

How to ~declare~ these glorious deductible contributions

Under “Deductions,” you’ll see a line item for “Self-employed SEP, SIMPLE, qualified plans.” That’s where you’ll tell the software how much you contributed, and “ooh” and “aah” as your tax bill lowers accordingly. As you can see, in 2021, my SEP IRA/Solo 401(k) contributions saved me an absolute boatload (yacht-load? We are talking about a billionaire’s game, after all).

And finally, the HSA—the consolation prize for our late capitalist healthcare hellscape!

If you have a high-deductible health plan (as defined by the IRS), you may be eligible for an HSA plan. The contributions and growth will be tax-free forever if you use the money for qualified medical expenses, so it’s a great place to rack up hella capital gains.

For 2024, the minimum annual deductible to be considered a high-deductible plan for self-coverage only is $1,600, and for family coverage is $3,200. The contribution limits vary on HSA plans for the 2024 tax year: If your health insurance plan just covers you, the limit is $4,150, and if your plan covers your family, it’s $8,350 for 2024.

You may already have an HSA set up through your work, or you may need to open one yourself, but once you surpass a certain amount of cash in the account (typically somewhere in the $1,000 to $2,000 range, but it varies by plan), you’re usually able to invest the funds—something you’ll do within your HSA account portal. 

You’ll have to go to your HSA provider and make a direct contribution (as opposed to a payroll contribution) to contribute one big, fat lump sum, which is technically suboptimal because direct contributions aren’t exempt from FICA tax the same way payroll contributions are. The good news is, an HSA contribution made in 2025 can be retroactively tax-deductible for 2024.

Moving forward, consider making your 2025 contributions through payroll deductions, because then your contributions won’t be subjected to FICA tax, either! Woohoo! Another 7.65% saved.

Any after-market HSA contributions (read: not payroll deductions, but new manual contributions) you make in 2025 for 2024 will be captured in the “Deductions” section:

When this won’t work

If you’ve already contributed the maximum to your HSA in 2024, unfortunately, this retroactive move isn’t an option (those contributions will be noted on the W-2 that your employer sends you). This also won’t work if you have a low-deductible plan.

The HSA is one of the best tax vehicles out there, because it’s effectively a second Traditional IRA that’ll never be subjected to required minimum distributions. 

If you hang onto your HSA until you’re 65, it’ll basically “convert” to follow the same rules as a Traditional IRA, and you’ll be able to make withdrawals for whatever you want (not just health expenses) without paying a penalty. You’ll pay taxes on your withdrawals like you would with a Traditional IRA if you don’t spend them on health-related expenses, but that’s about it. 

Someone who’s not covered by a retirement plan at work, has side hustle income, and has a high-deductible health plan could theoretically use all three methods.

Talk about a triple tax whammy! (I hate myself.)

It’s worth restating: I’m not a licensed tax professional. Please consult your CPA and do your own research before making big money moves. Hopefully this serves as a starting point for your pre-tax investing game this tax season if you haven’t made any decisions yet!

Generally, these colorful points weren’t new to me. He even mentioned a theoretical snag I’ve covered before—that it doesn’t scale—and that someone needs to keep clocking in and out for 40 years so the underlying companies fueling stock market returns will rise in value and produce that blessed 9%-per-year-before-inflation juice. Won’t someone think of the shareholders?!

What did unsettle my spirit, though, was his seemingly harmless description of the typical FI/RE devotee:

“Joe Millennial graduates from college and gets a job in the cube farm for $80,000 a year. He gets the cheapest apartment possible, rides a bike instead of driving, and eats ramen noodles. He does this for ten years, saving up to 70% of his income, and investing it in low-cost index funds. At the end of ten years, he has a million or so saved up, more if he is lucky. At that point, he retires to play the guitar or paint happy little trees, and gradually draws down his savings over time. If the stock market keeps going up as planned, he can stay retired for 50 more years, and get really good at guitar.”

This was, of course, the promise that initially drew me in like a moth to an open flame—you’re telling me I can compress my working life into one-quarter of the time then sail into the sunset, never to labor again? Where do I sign?! 

But for some reason, this recounting of the goal—the vision of 50 years of blank space—struck me as existentially fraught.

FI/RE lives somewhere in a tangle of Venn diagrams with hustle culture, productivity and business advice, and other maxims about creating a life of financial abundance. There are different sects: Some emphasize anti-consumption, as Jared noted, while others are more concerned with creating as much “passive income” as possible. 

One thing is true of all: In an effort to accelerate the path to not working at all, many adherents work a lot. 

Somewhere in my mainlining of these philosophies, my wires got crossed. I conflated being busy with being responsible; productive with being profitable. A sense of ambient hustle urged me forward toward an imaginary (or rather, quantified) finish line. I filled every spare moment with a podcast, newsfeed, or task, reflexively stuffing my day until it suffocated, removing any capacity for broader reflection. 

And with good reason! In school, this methodology worked: At the beginning of every semester, there was a syllabus prescribing a finite number of assignments, tests, and exams that, once finished, marked an endpoint that meant one to three months of uninterrupted downtime. One could get ahead, and the year was punctuated with long windows of respite between sprints.

But in the working world, “getting ahead” is an illusion. There is no point at which the semester ends, no natural stopping point. Instead, it’s week after week of that amnesiac delusion that “if I can just work extra this weekend and clear this to-do list, I’ll reach a point where I’m ahead and can take a breather.” Unfortunately, working “faster” usually just means working more.

In this context, FI/RE—the promise of a career finish line you can sprint past, into the land of compounding returns and endless summer vacation—was an irresistible dangling carrot. 

It’s important to recall, of course, that most people who “retire” early end up doing some other job or filling their time with something productive (otherwise, as Jared put it, your “visions of going to the beach, traveling, or visiting the grandkids” turn into spending your days “in the living room with the brown carpet with Fox News turned up to 11”). 

The point is, life is long, and if you’re just going to get another job—or otherwise devote your time and effort to something productive—in retirement, the thinking goes, What’s the rush? Why not just make money doing something you like, so you don’t have to rely on the fickle mistress of the public markets for 40+ years?

I was reminded of a conversation I had with a friend a few years ago who was self-employed working part-time. She only worked in the afternoons, took random days off, and approached work at a leisurely pace. As I worked four jobs simultaneously to produce as much margin as possible, I couldn’t understand why she wasn’t more interested in maximizing her income. When she asked me why I was working so hard, I scoffed at how silly the question was: “So I can get to the point where I can work however I want,” I explained. Duh! 

She didn’t seem to understand. “Oh,” she replied, “Well…I already work however I want.” Mic = dropped.

I’ve spent the better part of the last four years on a six- or seven-days-per-week schedule, putting in between eight and 10 bonus hours every weekend for maximum output. It began during the pandemic when I started working from home, and my personal and professional lives blurred inextricably together. Seeing my desk from the couch felt like an ever-present invitation; a reproach against my Sunday morning lazing. 

While at first I enjoyed the edge working all weekend gave me, somewhere along the line, it stopped providing an edge and became a necessity: In order to keep up with the pace I had set for myself (and the expectations that created!), I had to work every day. FI/RE, I figured, was the reward.

But this past weekend, I did an experiment: I avoided my laptop and phone entirely, knowing how even my purest attempts at good, old-fashioned doom scrolling had a tendency to drift mindlessly into Slack or my inbox, blacking back in two hours later and three folders deep in Google Drive. 

Hungry for the artificial sugar rush of infinite feeds and stimulation, my brain started flipping through a Rolodex of fragmented memories and ideas, not unlike the way I compulsively scroll my own Photos app when there’s no wi-fi on long flights.

But eventually, I read. I napped. I walked. I cooked and ate. After about 36 hours, I felt my nervous system beginning to unclench. Is this how people lived in the eighties?! I wondered, basking in the anachronistic glow of only having Large Screen, as Small and Medium Screens were safely shelved away. What a strange feeling to be so alone with your thoughts, I reflected, grasping at whatever memory floated to the surface and luxuriating in the sense of space.

With so much time on my hands, I thought a lot about what Jared wrote—how he prefers the 80-hour work week and his favorite time is Sunday night, because he’s always so excited to get up on Monday morning. After my weekend of nothingness, I felt a magical polarity I had long forgotten.

Paradoxically, I realized, FI/RE represented anti-hustle to Jared: a movement that suggested doing less. My interpretation was the opposite—that in order to ever do less, you must first do far more. 

But I wondered: Rather than resolving to live the life you actually want once you’ve surpassed a magic number, what if you tried living that way now? 

Whether that means more frequent vacations, a schedule with less pressure, or simply approaching day-to-day life differently, it’ll almost definitely mean it’ll take a lot longer to hit “the number”—but you’ll no longer be in any hurry to get there. 

How to do the Mega Backdoor Roth IRA

Ironically, the “Mega Backdoor Roth IRA” is not a Roth IRA at all: It’s technically an “after-tax” contribution to your employer-sponsored 401(k) or 403(b) plan, not to be confused with a Roth contribution, which is much more boring and akin to going through the “front door.” 

Unfortunately, not all 401(k) plans allow for after-tax contributions beyond the standard, employee elective deferral of the $23,500 contribution limit (of the four companies I’ve worked for, only two have allowed it). 

But in 2025, this strategy allows you to get another $46,500 of Roth dollars in the bank on top of your regular $23,500 contribution to a 401(k) or 403(b).

Bonus, albeit a potentially confusing one: You’re still in the clear to contribute $7,000 per year to a Roth IRA or Backdoor Roth IRA if you want to, as well. Your IRA activity is wholly separate from today’s discussion of juicing your employer plan for all it’s worth.

Why? Because the actual contribution limit for 401(k)s in 2025 is a whopping $70,000. 

Here’s how it works:

1. In your company’s retirement portal, you elect to contribute after-tax dollars above and beyond the $23,500 limit.

2. Your plan administrator then (a) converts them to Roth in-plan or (b) permits in-service distributions, allowing you to roll over the funds to a Roth IRA.

…and that’s about it. I pulled an old screenshot from a former employer’s contribution page so you can get a sense for what this might look like on the back end:

Since my base pay at the time was $128,000 and I wanted to contribute a pre-tax $22,500 as well as an after-tax $6,500 (I basically wanted to mirror a regular Roth IRA limit in 2023), my “percentages” were 17% and 5%, respectively. You’ll probably see some language around a “Roth In-Plan Conversion” that’ll ask if you want to “convert after-tax contributions” to Roth, and your answer is a resounding yes. 

Candidly, it might be more trouble than it’s worth if you have to manually roll over and convert the after-tax contributions every month, but if your plan converts them to Roth in-plan for you and you can afford it, it’s probably a no-brainer to get a few more tax-advantaged dollars working in your favor.

If you are faced with the manual-only option, some people like to wait until the end of the year to roll over a full year’s worth of their after-tax dollars to their Roth IRAs—but it’s worth noting you’ll pay additional tax at that point on the growth of those after-tax dollars at the point of conversion (assuming they grew, of course).

It’s also worth noting that your employer match counts toward the overall $70,000 limit. If you contribute $23,500 and your employer contributes $10,000 (#goals), your 401(k) bucket technically has $36,500 of “room” left ($70,000 – $23,500 – $10,000 = $36,500).

Importantly, there’s no income limit for this (yet!), so people who earn too much to contribute directly to a Roth IRA (or don’t want to bother with a regular Backdoor Roth IRA) may find this a more seamless way to get both pre-tax and after-tax/Roth exposure in one fell swoop. Now, to find a job with a tech company that offers this Mack Daddy benefit…

The impetus was the realization that my financial life was becoming increasingly complex. I was having a hard time wrapping my head around the wheels that were turning in the background, and I wanted to illustrate how money was flowing through the system.

At the time, I had four (sometimes unpredictable) sources of income, a maximum 401(k) contribution, and a lack of a true “emergency fund” savings account, thanks to a taxable brokerage account product from Betterment called a “Safety Net” that I used instead.

To help make my holistic financial picture a bit clearer, I envisioned a visual exercise to put it all to paper. Out came the colored highlighters, and on came the lightbulb above my head. 

I give you: The “money mapping” exercise. If your financial situation is complicated to the point that it becomes hard to keep up with (like how mine was), it’s worthwhile to take the time to streamline the way your money flows through your financial system. Here’s how to make your own, where the name of the game here is simplification. 

My 2025 Update

I didn’t re-draw my old system, but things have gotten progressively simpler despite adding another whole human to the mix in 2021 (hi, Thomas). We now have:

• Two sources of income (100%)

• …that first pay taxes (subtracts 23%)

• …and funds my 401(k) and HSA, and Thomas’s TSP (the 401(k)-style account that military members have) (subtracts another 10%)

• …then the rest flows into our joint checking account (the remaining 67%)

• …which pays our rent and our four primary credit cards each month (my business card, my AmEx Platinum, my AmEx Gold, and Thomas’s Chase Sapphire Preferred) (call it somewhere in the 22% of total ballpark)

• …and then funds our joint taxable brokerage account with what’s left (around 45% of total ballpark)

See? It’s way more fun with highlighters.

Start with income:

Sometimes we introduce more complexity slowly over time as our financial lives morph and grow around our habits. You know how it is: You start paying rent out of one specific checking account because it just so happens to be the one set up for withdrawals. Then, you open a new checking or savings account elsewhere, but still need to funnel money back to the old one to pay the rent, and, and, AND…it slowly becomes an unwieldy mess.

Of course, some people like to maintain a bunch of accounts for different things, but I’ve found personally that that becomes an unnecessary energy drain.

So, you’ll start by drawing the cash flowing from your income stream(s) into your central checking account (or accounts, if you maintain joint finances with someone in a “yours, mine, and ours” fashion).

The 401(k) contribution (or 403(b), or HSA, or…you get the picture) has to come directly from the paycheck, too, and that’s great—so make sure you’re demonstrating that on your money map somewhere. 

Illustrate your emergency fund: 

If you’re still growing your emergency fund, draw a dotted line from checking to savings to represent your monthly flow of cash. If your emergency savings are already funded, set it off to the side to visualize its “reserve” status—like an account waiting in the wings.

It’s there if you need it, but you aren’t actively funneling money into it. If you have a habit of “over”-saving (and therefore “under”-investing), this mental separation can help you see where it might be more helpful to reroute extra funds to a more growth-y destination. 

You may also have other savings or investing goals that you’re actively funding—like for a house down payment or future childcare—so you can draw those little metaphoric buckets as well.

Add in spending:

Most of my spending—necessary and discretionary—happens on credit cards, which I pay for out of the checking account. There are a ton of reasons to use credit instead of debit cards: security against fraud risk, cash back, points…the list goes on. 

But sometimes you have to pay something with a direct withdrawal (like my rent). I like to note that in my map where it makes sense.

You can think about the credit card as the first line of defense, or barrier, between your spending habits and your checking account. While you shouldn’t find yourself in a position where you need to be actively transferring money into checking from savings to pay your credit cards, I like to know when there’s a big-ticket item that’s going to be taken directly out of checking instead of funneled through a credit card with a “delayed” due date.

Draw post-tax investment accounts as offshoots from the checking account:

When you open a post-tax investing account like a Roth IRA or a regular taxable account, you have to deposit money directly into those accounts from checking or savings. Remembering to do this on an ongoing basis as you earn every month can be tedious, so I like to set up bimonthly auto-transfers that happen in the days following when I get paid (though in recent years as my income has become increasingly variable, I tend to manually check at the end of every month and make manual transfers, too).

What about taxes?

There’s a big missing piece of the visual puzzle above. Can you spot it? Taxes. Taxes will also be paid directly from your paychecks, so if you want to note it, you can (I did in my update above, just to twist the IRS knife). I recently sat down with a spreadsheet and listed our income, spending, and total tax burden, and was shocked at the pie chart that got spit out: We’ve paid more in taxes this year than we’ve spent on everything else combined.

That made me realize it probably makes sense to hire an accountant to double-check our tax strategy, vs. stressing about an incremental few hundred bucks spent here or there. (It also reminded me that now’s the time to invest in the business via #WRITEOFFS if anything comes to mind.)

Creating a sense of scale

You’ll also probably notice the percentages on the flow chart above. If I were really on my visual representation high horse, I would’ve drawn the boxes to scale (and actually, I low-key love that idea), but for the sake of my less-than-artistic first rendering, I just noted the percentages where applicable.

But drawing the boxes to scale can be helpful because it’ll help you see if you’re prioritizing investing (and doing so in an ideal way), or if there are a lot of leaky holes in your budget. For example, if only tiny offshoots are being sent to investment accounts or savings and the vast majority of your income is going right out the door in that spending bucket, it can help make your purchasing decisions a little more tangible.

It might also help you see where you’re prioritizing certain financial goals a lot more heavily than others—perhaps in a way you hadn’t realized. 

Why money mapping is a useful exercise

Besides the fact that you can whip out the highlighters and touch real paper for the first time in months, money mapping helps you diagnose large trends in your financial life.

It can also help reveal gaps in your own understanding. If you start filling in numbers and realize that you don’t actually know where part of your income is going every month, it can help visually guide you toward possible solutions.

For example, when I saw that 57% of my investing was going into a taxable investing account, it made me wonder if there were other tax-advantaged options I could—*ahem*—take advantage of first besides my 401(k) and Roth IRA. (Spoiler alert: I ended up contributing more to my HSA and opening a Solo 401(k) for my self-employment income.)

Happy mapping, nerds!

My new part-time job was at a gym’s daycare center, so I’d typically head there after school, do my four-hour shift until about 7pm, then venture upstairs (free gym membership, baby!) and walk on the treadmill for about 45 minutes. While I exercised, I’d review my notes for that day. I’d read through them as many times as I could over the course of the walk, and then head home and finish the rest of my homework.

In retrospect, this sounds like a pretty exhausting existence (or a testament to a 17-year-old’s boundless energy reserves). But this approach—spreading out the misery of my test prep with an hour of leisurely, low-pressure note review each day vs. panic-cramming for the 48 hours before each test—enabled me to start acing tests with very little “official” studying. My weekends before tests were (regrettably) spent running from the cops or (not-regrettably) hanging out with my parents instead of being holed up in Nina’s room practicing geometry.

The repetition of this daily routine paid dividends, literally and figuratively—while I did relatively well in school my freshman and sophomore year, my grades junior and senior year scored me an out-of-state college tuition scholarship that was worth, at the time, about $25,000 per year (and based on how the cost of college has risen since, I’ll assume it’s now worth $250,000 per year—#SadJokes). 

I didn’t have to sacrifice sleep, be a genius, or do anything exceptionally difficult: I just had to spread out the misery such that each day featured a little bit of work (no “off” weekdays), but no one day featured a lot of work.

Doing a little bit every day was more manageable than the alternative, and it generated better results—it didn’t require exceptional performance during high-pressure periods (i.e., in the days leading up to an exam), but instead took advantage of my regular ebbs and flows. I’m sure there were some afternoons when I retained more, and others when less material made it through my thick-ass teenage girl cranium, but I dollar-cost averaged my effort.

So often, I talk to young professionals earning above-median (in some cases, well above-median) incomes who feel as though there’s no point in investing in the stock market until they earn $X more (“X” is irrelevant for the sake of this example, but anecdotally, it’s usually about 20% more than whatever they’re currently earning). They’re delaying their misery until an unspecific point in the future that they assume will be less miserable, thanks to having more money on hand. But what does this often mean in practice? Forcing yourself to go above and beyond once you reach your forties and fifties. 

Part of the reason we have a tendency to do this, I think, is because we overestimate the struggle awaiting us—we assume we’ll need to turn the dial way up in order to make progress at all, and the idea of doing so seems unbearable (or flat out impossible) in our current state. 

But you don’t need to cram the misery into a single decade or two. You can spread it out. The thing is, spreading it out over time requires prioritizing it now—even if it’s just “a little every day.” 

Comparing these two strategies

Retirement is life’s ultimate financial pass/fail exam. 

Some people start paying more attention as they see retirement looming on the horizon—the metaphoric Tuesday before the Friday test—and spend the intermittent days (years) sick with an undercurrent of anxiety, aggressively cutting back on their spending at the exact moment when they’re probably most interested in letting loose, and realizing they may need to work for a lot longer than they realized. 

They’re forced to cram a lifetime of financial pain into a few short years. 

Compare this with the “spread it out” approach. Rather than struggling to dump 50% of your income into your 401(k) and IRA at the last minute and giving it very little time to compound before you’ll need it, diverting 10% earlier in life (a much smaller sacrifice!) means you’ll likely never need to save more than 10% at a time. This is true even in the years leading up to the big day, when you pull the ripcord and float away from Zoom calls and work alarms forever.   

The chart below illustrates the contribution patterns of the two “paths,” one wherein someone saves 10% for all 40 years of their working life, and the other where someone realizes in year 30 (about 10 years before retirement) that they need to kick it into gear. (This assumes two earners who both take home $50,000 per year after taxes in year 1, rising by 3% per year.)

The person making consistent 10% investment contributions never invests more than $15,800 per year over the 40 years. The “cramming” investor must start investing in year 30 with a $58,000 contribution.

The red investor gets to go balls to the wall with the AmEx for the first 30 years, but notice how similar their spending is for the majority of their working lives, despite how different their last decade looks:

It looks like a negligible difference in spending…until it doesn’t. The blue investor got to spend 90% of their income through all 40 years—whereas the red investor got to spend slightly more until year 30, but then had to drop down to a harsh 50% for the last 10 years. 

And of course, if you’re familiar with how exponential compounding works, you may already know that the 10% investor will skid into year 40 with more money. The chart below illustrates their respective account balances, using an average annualized rate of return of 7% in both cases:

The 10% investor will have almost $1.6 million in today’s purchasing power in year 40; the “cram” investor will have a little over $1.1 million. But with the red investor’s high save rate, they’d catch up to the 10% investor if they worked and saved 50% for an additional six years.

(In order for them to retire with the same amount as the 10% investor at the same time, they’d need to maintain a 70% save rate for the last decade.)

Is it easier to save 10% for 40 years or 70% for 10 years?

If you’re trying to retire early, a 10% savings rate probably won’t cut it (try 15% or 20% if that’s your goal). But if you’re happy to retire on time (which is no small feat!), a lifetime of investing $1 of every $10 you earn—spreading out your sacrifice—will do the job.

And while it depends on how your income changes (and maybe your personality, too), I’d wager that a consistent 10% savings rate is almost always going to be a walk on the treadmill compared to condensing all your sacrifice into one big sprint at the end.

Should I get a high-deductible health plan just so I can have an HSA?

Well, maybe. As with all things financial, it depends—but there’s a framework that might help. (And it’s worth stating explicitly: This discussion assumes your only concern when picking a plan is financial. If you have specific health concerns or doctors you need to make sure you can see in-network, then your health will of course be the number one priority!) 

If you’ve got an employer who will pay for all your medical expenses with no deductibles or premiums (shout-out to my past employer, Meta; Zuck, you’re the realest for the totally free healthcare), then yeah…I’d probably take that deal 11 times out of 10.

But what if you’re presented with a smorgasbord of confusing options? A PDF packet so thick it makes your eyes water? Then what?

You might have a few choices—some with high deductibles, and others with low ones. “High-deductible” is defined by our #BoizAtTheIRS as any health plan with a deductible higher than $1,650 for a plan covering just you, and $3,300 for a plan covering your family.

Moreover, the maximum out-of-pocket costs for these plans are $8,300 for plans covering just you, and $16,600 (gulp) for family plans. 

I don’t know about you, but I’d do some pretty questionable shit for a deductible as low as $1,650. Mine is $2,500 for a plan that just covers me, and my guess is that many of you will have access to a high-deductible health plan. (If you’re like, “What in God’s green pastures is a deductible?”, read this post for a healthcare primer about premiums, deductibles, copays, and more.)

More often than not, a high-deductible plan will have lower monthly premiums than your alternate options. You can calculate your total maximum costs each year by adding up:

• 12 months of premium costs (i.e., what’s being taken out of your paycheck to pay for the plan). If your insurance costs $200 per month, you know you’ll pay at least $2,400 per year in premiums even if you never set foot into a doctor’s office.

• Your out-of-pocket maximum (which is a limit that’s higher than your deductible, because the insurance companies are excellent at coming up with convoluted ways to continue passing the buck to you after you hit your deductible). The silver lining is that it should represent the most you’d possibly be on the hook for in a given year. (Key word: should. If you spend on services that your plan doesn’t cover, that’s not included in this limit.)

Then, when you’re debating between the low-deductible plan and high-deductible plans, you can ask yourself at a high level:

• Do I want to pay more per month but (probably) have a lower deductible and out-of-pocket maximum?

• OR, would I rather pay less each month but (probably) risk it with the higher deductible and out-of-pocket maximum?

Making matters more complicated (yay!), sometimes these plans involve varying “copays” or “coinsurance” that can make the analysis a little trickier.

For example, Henah and I were comparing health plan options the other night and noticed this:

The plan on the far left, “Empire PPO 1000,” is a low-deductible plan that costs $200/month, but with paradoxically higher out-of-pocket maximums ($5,000 single/$10,000 family) than the high-deductible plan’s ($70/month) out-of-pocket maximums ($3,425 single/$6,850 family). Huh?! (Because the nomenclature might be confusing, it’s worth clarifying that—in the plans shown—all three technically operate as PPOs, or preferred provider organizations. It’s a common misconception that high-deductible plans can’t be PPOs, but they aren’t mutually exclusive.)

What gives? Aside from the fact that someone needs a PhD in data science to make sense of this chart, notice the “Primary Care Visit,” “Specialist Visit,” “Urgent Care,” and “Emergency Care” rows. The low-deductible plan has copays—meaning you’ll pay $20 a pop at your primary care doc, $40 at a specialist, $40 for urgent care, etc. for all in-network visits.

And as a fun reminder, those copays don’t count toward the plan’s deductible—but they do count toward your out-of-pocket maximum.

The higher deductible plan in this example? Forget about copays altogether. You’re paying for everything out of pocket until you hit that deductible, honey (after which the listed 0% coinsurance kicks in). Best of luck to you and your wallet! The good news, of course, is that the maximum (again, as long as you stay in-network) you’ll be on the hook for in a given year with that example plan is $3,425 (just you) or $6,850 (family) after you pay your premiums. You’re probably just more likely to hit that deductible than if you’re using a low-deductible plan with copays for routine visits. 

For example, if Henah—who has the low-deductible plan—goes to see an in-network primary care physician, she’ll pay a $20 copay. If I go to see a primary care physician with the high-deductible plan, I’ll pay whatever they charge for an office visit (usually in the ballpark of $150).

That said, every plan is different, but please enjoy our Slack conversation, which became a flurry of confusion and numbers. Here’s a snippet of our Friday afternoon party in the DMs, where we panic-calculated cost-benefit analysis: 

As you can see, the cost calculation in this example is:

• High-deductible plan for an individual: $70/month + a $3,425 out-of-pocket maximum per year in costs (unless something major happens, you’re probably paying full price for everything out-of-pocket throughout the year) = Between $3,240 and $4,265 projected maximum cost

• Low-deductible plan for an individual: $200/month + a $5,000 out-of-pocket maximum per year in costs, but with copays that’ll likely cover routine stuff cheaply and a lower deductible ($1,000) you’d need to hit before insurance would begin kicking in and covering 70% of costs until you’ve spent $5,000 total = Between $3,400 and $7,400 projected maximum cost

This example illustrates why people often instruct those who are “young and healthy” or who have very few predictable health-related expenses to go for the higher deductible plan, assuming they won’t need to go to the doctor very often (or at all) and can use the insurance as protection against catastrophic health issues that would run up bills in the tens (if not hundreds) of thousands of dollars. Slowly gestures to the podcast episode about how backward the system is…

I digress.

But that’s not even close to where this analysis ends, because some high-deductible health plans have an ace up their sleeve, in the HSA.

The HSA can be a game-changer, thanks to the tax savings

Because you won’t pay any federal, state, or FICA taxes on payroll contributions to your HSA, you can pretty easily calculate the potential savings you’ll gain (read: money that stays in your pocket instead of being sent off to Uncle Sam for his next highway improvement project) based on how much you earn.

Assuming you’re able to invest the maximum amount in your HSA ($4,300/year for a health plan that covers just you, and $8,550/year for one that covers your entire family in 2025), your potential tax savings are #thicc. In case you’re like, “That seems like a lot of money, dude,” it’s roughly $165 per biweekly paycheck for the “single” coverage and $329 per paycheck for the “family” coverage. 

That still may sound like quite a bit, but I think of it like this: Would I rather pay more to an insurance company for a lower deductible, or pay less to them every month and pay myself more (in an HSA)? Depending on the difference in your monthly premiums and the shitty-to-decent gradient of your plan options, it may be pretty close.

Wondering how much you could stand to save in taxes from HSA contributions? I did the hard work for you; I took the marginal tax rate + 7.65% FICA tax to see how much you’d save on your annual tax bill:

• 10% bracket saves $759 on the singles plan, $1,509 on the family plan 

• 12% bracket saves $845 on the singles plan, $1,680 on the family plan 

• 22% bracket saves $1,275 on the singles plan, $2,535 on the family plan 

• 24% bracket saves $1,361 on the singles plan, $2,706 on the family plan 

• 32% bracket saves $1,705 on the singles plan, $3,390 on the family plan 

• 35% bracket saves $1,834 on the singles plan, $3,647 on the family plan 

• 37% bracket saves $1,920 on the singles plan, $3,818 on the family plan 

(If you’re not sure which tax bracket your taxable income falls into after accounting for deductions and such, you can check out the 2025 brackets here.)

For example, a family in the 24% bracket who contributes the full $8,550 each year will claw back $2,706 in tax savings, which can directly offset the costs of the insurance. Of course, it also means you have to be able to tie up that much money in your Health Savings Account, which isn’t always realistic.

This also doesn’t take state tax savings into account, which could add even more money back into your pocket; notably, California and New Jersey don’t recognize HSAs as pre-tax vehicles so you won’t save on state taxes in either of these places. Womp womp. Good thing taxes in those states are so low! Oh, wait…

Time to pull it all together for the grand finale.

The tax savings from investing in an HSA can help give the high-deductible plan an edge over the low-deductible plan

Let’s do a quick example to drive home the point and revisit our earlier options.

Things look pretty neck-and-neck, especially when I consider the fact that the low-deductible plan’s copays are likely to make each individual visit to the doctor very affordable (as opposed to being on the hook for $200 for a checkup wherein you accidentally ask one (1) specific question). 

• High-deductible plan has the potential to cost $840 in premiums + $2,500 deductible, or a combined $3,340 (with a worst case scenario of $4,265). We’ll assume it’s probably pretty likely I’ll be on the hook for at least the first $2,500 of my care in a given year.

• Low-deductible plan has the potential to cost $2,400 in premiums + $1,000 deductible, or a combined $3,400 (with a worst case scenario of $7,400). Thanks to the copays, though, we can assume I probably won’t be on the hook for routine care (beyond $20 or $40 here and there). 

But what if I’m in the 24% tax bracket, and I’m able to contribute the full $4,300 to an HSA that just covers me? That contribution gets added to the “assets” side of my balance sheet, increasing my net worth, and I save $1,361 on my federal tax bill, which means I’m “making” an additional $1,361 that year—lowering the net cost of paying for premiums and hitting the deductible in the high-deductible plan to $2,039 (again, we’re not counting the contribution to the HSA as a cost, since you’re keeping that money—it’s not as much a cost as a cash flow consideration).

Now, the difference between our two options is:

• High-deductible plan’s net cost to hit deductible: $2,039

• Low-deductible plan’s net cost to hit deductible: $3,400

So we’d save $1,361 over the other plan’s premiums and deductible—is that worth the hassle? Well, remember, it’s not just the up-front savings we’re considering: It’s the fact that these funds in your HSA are invested and will continue to grow tax-free over time, too. (As opposed to the low-deductible plan, where there’s no associated investment vehicle, just potentially lower up-front costs.)

Sometimes I feel like insurance plans are created by a bunch of MBAs in suits throwing darts at a spreadsheet, so it may not always work out this way—but this example is intended to illustrate the framework for determining how much the tax savings may offset the higher deductible of a high-deductible plan, based on your specific plan options.

Put another way: Depending on your tax bracket and single vs. family coverage (assuming you’ll contribute the maximum to your HSA), a high-deductible plan can cost more on the surface than a low-deductible plan, and still end up being net-cheaper.

As complicated as access to healthcare in the US is, if we can view these questions like math problems, it can help us make a decision

The reason choosing a health plan is complicated (aside from the obvious; see previous unintelligible charts) is because we often don’t know what type of medical expenses we’re going to incur ahead of time, making the choice process uncertain and stressful (USA! USA!). But by calculating the “absolutes” of maximum possible costs and factoring in our potential HSA tax savings, we can make a more informed decision. 

Or, we could move to Sweden. There’s always Sweden.

It wasn’t until I found myself in a peculiar economic position that a more helpful version of this rule emerged for me: Don’t live beyond your assets.

Once I found myself graduating from a median income to a higher one, I straddled the line between two worlds: Do I maintain my exact same lifestyle and invest everything extra, or do I recognize that I can afford a little lifestyle creep?

The hard part? There’s no rule of thumb for how to handle such a situation. I felt silly skimping on brand name orange juice, but I was also terrified of backsliding into the old, spend-y habits that used to drain my checking account every month.

Just because I was making more money didn’t mean I was wealthy, and I struggled to find balance.

When I made $50,000/year, these decisions were paradoxically easier: I didn’t have a ton of extra cash every month. I spent what I spent, saved what I saved, and the whole ordeal involved less than $3,100 per month of total inflows and outflows.

But what if you suddenly find yourself making 3x that? 5x? 10x? (Hey, dream big!)

Some suggest keeping your savings rate the same as you earn more (increasing the amount you’re saving proportionally with your income), but that introduces a new quandary: Your target is technically getting further away, and your financial independence date doesn’t actually get any closer despite your income rising.

If only there were a reliable metric we could add to the equation to help guide our decision…

Fortunately, there is: Your net worth.

Your income might look as though it justifies your spending—but would your net worth?

The big question mark for me was this: Sure, I have more disposable income now that could feasibly fund a more lavish lifestyle. But if you looked in my investment accounts—my larger financial picture—would my spending behavior still seem reasonable and justified?

An example

Let’s pretend I’m a beautiful 23-year-old TikTok star who suddenly found myself earning $400,000 per year thanks to lucrative brand deals and a sparkly personality. I’m making great money, no?! I’ve had my eye on the Mercedes-Benz G-Wagon for a while, a $140,000 car. Could I make the case for affording that vehicle, given my income? Well, I suppose so—it’s roughly ⅓ of what I earn in a year, right? That’s not too outrageous. 

But wait—my liquid net worth is only $50,000. Now does it make sense for me to buy a car that’s worth nearly 3x my entire life savings? Almost certainly not. 

By marrying these two metrics—our liquid net worth and our income—we can strike a better balance around the type of lifestyle that’s reasonable to live, as opposed to just looking at one number or the other. While income is the number most people use to determine what they can spend, it only tells half the story.

Here’s where I landed (and I’ll share how I formulated this below): Your reasonable annual spend is the average of 4% of your current invested assets—inspired by the 4% Rule—and your income.

For example, someone who has a net worth of $250,000 and an income of $250,000 (let’s pretend that’s after tax, for simplicity’s sake) would net the following annual spending that’s beneath both their income means and net worth means:

4% of your net worth: $250,000 * 4% = $10,000
Post-tax income: $250,000
$10,000 + $250,000 = $260,000

$260,000 / 2 = $130,000

In this example, someone who makes $250,000 per year and is worth $250,000 would find a reasonable “below their means” annual spend of $130,000 maximum. This allows them to enjoy their higher income without meaningfully disrupting their progress toward financial independence.

(Note: I’m using “post-tax” a little colloquially here; if you’re also tossing a giant chunk of money every month into something like a 401(k), HSA, 403(b), or other account sponsored by your noble corporate benefactor, don’t forget to include that in your income, too—it’s still your income, you’re just opting to save it before you see it like the wise Rich Girl you are.)

Here’s a table that takes incomes between $50,000 and $500,000 and net worths between $50,000 and $1,000,000 into account (our example is shaded in green).

How I came up with this part-art, part-science formula

The “4% of net worth” figure serves as a bit of an anchor: It reminds you of the type of spending that your current invested assets can support (thanks to the 4% rule), which can lend some perspective to how much progress you’ve already made and how far you have to go.

As you’ll see in the table, even someone who’s worth $1 million and earns $250,000 should spend no more than $145,000 per year—because while it sounds like a lot of money (in both cases, because it is!), the proportionality of financial progress means they’d need roughly $3.7 million invested to support their spending if they were to lose their income (rendering a net worth of $1 million still quite far from their goal). 

This formula keeps a tight leash on lifestyle inflation by grounding it in the reality of one’s net worth—never allowing the runaway freight train of luxury cars and Uber Eats (guilty) to derail one’s progress completely.

On the flip side of the equation, if someone found themselves on the opposite side of the income spectrum but with similar moolah in the bank—$50,000 income and $1 million net worth—you’ll notice that the recommendation is to spend nearly everything they’re earning, because they’re so close to financial independence so as to not need to be saving much more.

Widening the aperture in this way allows you to give weight to what’s arguably the more meaningful, permanent variable in your financial life—your net worth—as opposed to basing 100% of your spending decisions on your current, subject-to-change income. This guideline should also help high earners on their way to financial independence understand just how much they can indulge with their incomes—without going overboard.

Plus, I think you might be surprised to see how our revenue and expenses break down (hell, I was surprised). 

Moreover, my experience building a business within a business has been interesting since Money with Katie was “acqui-hired” in January 2022 by our parent company, Morning Brew. Prior to that acquisition, I was a solopreneur, and my revenue was roughly $250,000 in Year 2 (an infinite increase from Year 1, when I made $0). 

The acquisition meant that I would join the Brew to run the franchise and have access to part-time resources within a larger, more established media business, and…well, the results speak for themselves.

We don’t gatekeep in Money with Katie Land (if anything, we prefer gate-opening), so without further ado, here’s how the franchise made money last year, plus key takeaways () where applicable:

“Direct to Consumer” Revenue: $663,048

Affiliate revenue, merchandise sales, Wealth Planner sales, and educational products, like our Budget Like a Millionaire and Tax-Smart Investing master classes (though the second didn’t launch until 2023).

Affiliate revenue ($83,801): One of our revenue streams is affiliate links for credit cards that we recommend in our Travel Rewards content, but it’s really our only source of affiliate income. While affiliate revenue is a popular choice for many creators who organically plug products they believe in, it’s not part of Morning Brew’s broader sales strategy, which means it’s a smaller one for Money with Katie, too. 

I think of affiliate revenue like a double-edged sword—it can be truly passive, but I think it works best as a “quality over quantity” game. In our world, it was more beneficial to focus explicitly on a small handful (and now only one!) high-value affiliate relationship that was easy to build into content we would’ve been making anyway.

Merchandise sales ($107,318): Think our trademark RETIRED sweatshirt, Rich Girl Summer koozies, and the “Mom, I Am a Rich Man” line. We did a lot of testing and learning around product in 2022, and ultimately decided that while certain kitschy offerings are fun, we mostly want to focus our efforts on functional tools rather than branded merchandise.

Frankly, I was surprised this line of business did this well. Our best merchandise products played off something happening in real time within our community, like the My Qualifications mug, which spawned from a cold DM I received from someone who told me our feminine branding was “off-putting” and that we could reach more people if we’d drop it. The message closed with, “As a straight man, I can assure you my opinion carries weight.” I shared the DM on Instagram Stories and said I wanted to put it on a coffee mug—then we did, and it sold out overnight. On the flip side, merchandise that we developed in a vacuum sat on the shelves.

Wealth Planner sales ($407,750): This is our flagship, core product, and the apple of my eye. In the UX world, we did something called dogfooding (eating your own…dogfood? I don’t know, it’s a metaphor that leaves a lot to be desired), or using your own product in order to help make it better, and man, that’s been true for the Wealth Planner. I’ve been eating my own “dogfood” since Day 1, which means I think of new enhancements almost every month. We try to keep the price point accessible for this product, but also want to avoid making it so cheap that it inadvertently suggests it’s a low-value product. We just kicked off development for the 2024 Wealth Planner, which will launch in November, because it typically takes 5–6 months to get it right.

The Wealth Planner is by far our biggest single source of revenue, and it’s also the line of business that makes me proudest, because I know how impactful it can be in someone’s financial life. The pricing of a digital tool is always the tough part, and we’ve increased the price incrementally over the years, as we’ve had to invest more money in development and as we’ve made the functionalities more robust. Having a staple product that you know will work for most everyone in your community (because it directly addresses the reason they’re interested in your work) is nonnegotiable for a creator-led business (Thomas Frank addresses this in this week’s episode, too).

Educational products ($64,179): This is an area we’ve devoted more resources to in 2023, after assessing where we want to be investing more of our time and energy. It hadn’t historically been a major focus for us—probably because we give away the vast majority of the value we provide for free to our audience (made possible by an advertising model). Our courses focused on a deeper dive into budgeting and building a spending plan that actually works, as well as tax-smart investing philosophies that aggregate all the goodness of the tidbits you’d find strewn throughout our blog posts, podcasts, and social media into a coherent curriculum.

I struggle with courses, mostly because of the price point. It’s an area where I know we need to improve, because we get questions all the time about more advanced offerings. We tried a cohort-based course in early 2022 and ended up not moving forward with it because we didn’t have enough sign-ups to cover our expenses; this was a big surprise for me, as I figured live courses would be preferable to asynchronous learning. Turns out people don’t want to air their financial grievances to strangers—which, fair.

Advertising Revenue: $489,465

Ads sold for the newsletter, podcast, and social media (though our social media sponsorships are all part of our larger podcast sponsorship; we rarely do one-off social media campaigns that aren’t also part of a broader campaign).

It’s difficult to delineate advertising revenue by product because we don’t typically sell things à la carte (instead, a full package for a sponsor might entail coverage on all our properties), but we tend to work with fewer, large sponsors as opposed to a ton of smaller ones.

Total 2022 DTC + Advertising Revenue: ~$1.152m

Adjacent sources of revenue ($30,123)

On the side, I’ll sometimes do corporate speaking engagements or seminars for large groups, but this isn’t something I actively seek out, as running the business described above takes up most of my time. 

Expenses

Ah, yes—the non-fun part of the equation. How much does all of that cost? 

Merchandise ($31,280): When you sell physical product, you first must buy physical product. 

Delivery and production ($39,546): Software, tech products, and other production costs. 

Salaries, wages, healthcare, 401(k) matching, contractors, and payroll taxes ($502,113): The “people” costs side of the equation, and by far the largest line item.

We’ve also expanded in 2023, which means our staffing costs have increased—but in 2022, we were a one-woman show (read: me) until May, when we made our first full-time hire: Henah, my executive producer. (You know her! You love her! She’s…my Rich Girl Roundup costar and the wind beneath my wings.)

There are some other smaller costs—a few thousand dollars for travel, a couple hundred bucks in office supplies, some small licensing fees, etc.—that I’m not including here because they cumulatively don’t add up to more than $10,000 (1% of our budget, based on revenue).

And, of course, three big lessons learned

1️⃣ The importance of hiring well. Our first full-time hire, the aforementioned Henah, came directly from Rich Girl Nation—and her involvement in the business made a world of difference last year when I was drowning on my own. It’s hard to overstate how crucial proactive competence is in the early stages of a business (or how damaging it can be when you’re either understaffed or incorrectly staffed).

2️⃣ The challenges of a creator-forward business model. Sometimes your biggest strength as a creator brand (i.e., the ease of relying on your own personality and opinions) is also your biggest weakness. There are obvious issues with long-term scalability when the brand ethos is so dependent on one person, as well as the fact that—at any moment in time—everyone could decide they think my voice is annoying and my takes are bad and, well, that’s the end of that! We’re actively thinking through how to address the potential vulnerabilities this introduces.

3️⃣ Trying to do too much. It’s so easy to get distracted in an entrepreneurial landscape that’s constantly evolving, and I have to continuously remind myself that we need to focus on our core competencies and what actually matters for our bottom line and larger goals. Aka, not virality on TikTok or rapid “follower” growth on Instagram, but instead producing an incredibly high-quality show every single week and delivering enough value to our newsletter subscribers to make them feel as though the time they spend reading is well spent. I had to reevaluate where I was spending the bulk of my time at the end of 2022, and realized I was falling too often into the trap of petty metrics (How many plays did that Reel get?) and not enough time on the higher ROI activities, like researching and writing.

Looking forward

There’s a saying I like in business (and life, I suppose): “What got you here won’t get you there.” 

The pure relentlessness of my obsession and a truly serendipitous full-time hire helped us scale from $250,000 to $1m in annual revenue, but in order to reach more people with even better products (whether that be the podcast, the Wealth Planner, or something else entirely), we need to make sure we build systems that support us (vs. just brute-forcing our way through the week, every week). 

Part of this entails making sure each person in Money with Katie Land is operating in their zone of genius for the majority of their time spent working. And once we’re confident we can run our existing platform(s) excellently (and like a well-oiled machine!), we’ll be able to explore things like four-day work weeks, new lines of business, and more unique opportunities.