The Third Rule Of Financial Independence Could Also Be Your Biggest Regret

As someone who has been writing about financial independence and escaping corporate America since 2009, I’ve developed several rules that serve as the backbone for achieving FIRE and staying free. They are simple, but not easy. Ignoring any one of them can set you back years.

Below are the first two rules as a reminder, followed by the third rule that many people overlook until it’s too late. If you do not follow the third rule, you will have no way out when you've finally had enough.

Lucky for you, you're reading this post so you won't look back on your life with this financial regret if you’re under 40.

The First Rule of Financial Independence: Don’t Lose a Ton of Money

If you lose a ton of money through improper risk exposure, you ultimately lose time – the most valuable asset we have when trying to break free from work as soon as possible. A 50% decline in your portfolio requires a 100% gain just to get back to even. At a 10% annual return, that recovery takes 7.3 years.

You cannot afford to waste seven prime years of compounding because you chased the hot stock of the month, went on margin, or bought growth stocks at peak valuations with little savings buffer. In most cases, these “bets” aren’t really investments. They’re disguised gambles born out of impatience and a desire to YOLO invest.

To better protect yourself from financial destruction, estimate your risk tolerance by calculating your FS-SEER. Then stick to a disciplined asset allocation model throughout your earning career. When you’re trying to retire early, avoiding catastrophic losses is more important than hitting home runs. The same is true once you’ve given up your day job because you can’t go back to the salt mines.

The Second Rule of Financial Independence: Don’t Extrapolate Your Income to the Sky

Projecting your income forward in an upward curve indefinitely is how dreams get overextended and finances get destroyed. You start buying too much car, too much house, or too many nonessential luxuries because you assume tomorrow will always be richer than today.

Eventually, your income levels off, declines, gets disrupted by layoffs, or disappears entirely. When that day comes, you feel the crushing pressure of everything you bought, especially if you financed it.

Cars and homes come with endless recurring expenses: insurance, maintenance, taxes, repairs, fender-benders, natural disasters, the list goes on. Since overconsuming housing and cars are the top two personal finance killers, I created the 1/10th Rule for Car Buying and the House-to-Car Ratio to keep lifestyle inflation under control.

Staying disciplined here keeps your saving rate high and your path to financial independence clear. In fact, these are the two most important and relevant personal finance ratios to follow for financial freedom.

The Third Rule of Financial Independence: Build a Taxable Portfolio

The older generations were forgiven for not building large taxable portfolios. Many had pensions, affordable healthcare, and full confidence in Social Security. But if you want to break free from corporate America before age 59.5, you must build a sizeable taxable brokerage portfolio.

Your taxable portfolio is what provides liquidity and passive income to bridge the gap between when you leave your job and when you can access your tax-advantaged accounts penalty-free. For early retirees, this is the engine that keeps the fires of financial freedom lit.

Yet it is the chronic underbuilding of taxable accounts that leads to many of the modern FIRE complications we see today:

1. The rise of Coast FIRE

Coast FIRE is often a psychological coping mechanism – a way to claim “I’m financially independent” without actually being able to retire. In reality, there is little difference between someone who is Coast FIRE and someone who simply maxes out their retirement accounts while working.

The danger is acting like you're FIRE when you're not. It is better to face the truth, then to constantly tell yourself lies to make yourself feel better.

2. The need to constantly hustle after quitting your job

If you don’t have enough passive income from taxable assets, you replace the stress of your day job with the stress of entrepreneurship, inconsistent income, and no employer benefits. Suddenly, you’re running a FIRE podcast asking for donations during a pandemic. You're building online courses that don’t sell, or doing side hustles you never actually wanted.

And eventually, you consider going back to work because making your own money is harder than you thought.

3. Forcing your spouse to continue working

This may be the saddest outcome of not having a large taxable brokerage account. Because there isn’t enough touchable money to fund your lifestyle, your spouse keeps grinding long after they want to stop, simply to maintain healthcare and cash flow. Your dream of joint early retirement becomes a solo fantasy.

No Regrets If You Try

By now, you can see why ignoring the third rule of financial independence may become your biggest regret. Without a sufficiently large taxable brokerage account, early retirement stops being a choice the moment your job turns miserable. You are financially exposed precisely when you most want optionality.

That said, even if you fall short of your original target, there is still real value in the attempt. You made a conscious decision to design your future instead of sleepwalking through it. You forced yourself to save, invest, and think several moves ahead while others stayed trapped in comfortable routines that quietly became cages.

But let’s not kid ourselves. Financial independence is not a mindset or a label you get to claim. It is a condition. If you still have to tolerate a micromanaging boss, a toxic culture, or colleagues who undermine you because you need the paycheck, you are not financially independent.

FIRE demands real change, not theoretical freedom.

Why You Must Build a Taxable Portfolio: Practical Reasons

A large taxable portfolio funds the life you want after you retire early but before age 59.5. That gap must be provided for if do not have enough passive income to cover your basic living expenses.

Even with a disciplined, frugal mindset, FIRE should allow room for joy, especially if you have kids or plan to have kids post-retirement. Living like a monk to live like a monk in retirement may not be ideal.

Your taxable portfolio becomes the funding source for your largest post-FIRE expenses:

1. A Nicer Home

Sure, you can live in a camper van or move to Thailand if you're Lean FIRE. But eventually, most people want stability, community, and a permanent home base. Take it from me, someone who lived in six countries growing up, worked in international equities for 13 years, and has visited about 60 countries. Traveling gets boring after a while.

If you haven’t purchased a primary residence yet, your taxable portfolio is what will give you the down payment flexibility. This is why some readers pushed back on my article about record-high housing affordability: your gains inside tax-advantaged accounts are inaccessible without penalties if you're younger than 59.5.

Exactly. And that’s the point.

If you want to climb the property ladder while working or during FIRE, taxable assets are your only practical source of housing capital.

With a large taxable portfolio, at least you won’t be forced to move away from your friends and family to save money either.

2. A New Car

The average new car now costs nearly $50,000, and eventually every car breaks down and needs to be replaced. If you no longer have strong cash flow in retirement, you will have to tap your taxable brokerage account. It can be painful, but if you need personal transportation, it is unavoidable.

Just like with home buying, liquidity equals leverage. You can easily save 1-5% off the price of a house or car if you pay cash thanks to your taxable brokerage account.

3. Independent School Tuition

If you want the option to pay back-breaking $20,000–$75,000 a year for private school when you're FIRE, you need cash flow or a large taxable brokerage portfolio to draw from. Otherwise, public school or homeschooling are the only options.

I’m a supporter of public schools, having attended them since immigrating to America in 1991. There’s tremendous character-building value in navigating challenges early. The real world is a harsh place to operate.

But I also understand the advantages of independent schools: more customization, smaller class sizes, better support, and, in some cases, greater safety.

The challenge is that the ROI of education is declining due to technological disruption, especially from AI. Many kids will finish 17 years of schooling only to find themselves underemployed or mismatched with the job market.

Still, if your cash flow can support grade school tuition, spending money on children’s education is one of the best ways to decumulate in retirement.

For working parents, as written in my WSJ bestseller, Buy This Not That, I recommend earning 7X the net annual tuition per child before enrolling – an upgrade from my original 5X rule due to declining educational returns. Your finances must be solid before taking on such a luxury expense.

4. Unsubsidized Health Insurance Premiums

Sadly, many people are afraid to retire before 65, when Medicare kicks in, because healthcare can be unaffordable before then. Medicare costs about $250 or less a month on average, usually with 20% coinsurance. Having a large taxable portfolio helps you overcome this fear of breaking free and keeps you free despite egregious 7%+ annual premium increases on average.

The reality is, even low digit multimillionaires are qualifying for healthcare subsidies that were originally meant for the elderly or less wealthy. As long as your income is below 400% of the Federal Poverty Limit for your household size, you will receive some level of subsidy.

Because maxing out all your tax-advantaged accounts is the baseline recommendation for anyone pursuing financial independence, you can use this baseline to determine your target taxable portfolio size. The larger you can build your taxable portfolio, the better.

If you want a specific objective, aim to max out your 401(k) and build your taxable portfolio to at least the same size of your 401(k) or the combined total of all your tax-advantaged accounts. Once you get to 1X, keep going! Hitting this ratio puts you in a strong position to retire before 59.5 without stressing about early withdrawal penalties.

Yes, I know this financial target isn’t easy. But the most worthwhile goals rarely are. Even if you fall short, simply aiming for it ensures you’ll accumulate far more in your taxable portfolio than if you never tried at all.

Since there is no annual contribution cap on taxable investing, your main limiting factor is your income. Therefore, not only should you continue pushing for raises and promotions at your day job, but it’s also extremely helpful to take on side work outside your normal hours. Every additional dollar earned can be funneled directly into building the freedom-producing portfolio you’ll rely on once you leave corporate America.

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Don’t Look Back With Financial Regret

Nobody wants to reach their 60s or 70s wishing they had worked a few more years, saved a little more, or built that taxable portfolio when markets were cheap and compounding was on their side. Regret doesn’t show up early. It shows up late – quietly at first, then all at once while you're alone with your thoughts.

The biggest regrets I’ve seen over 16+ years of writing about financial independence fall into three categories:

  1. “I didn’t start investing early enough.”
  2. “I spent too much when times were good.”
  3. “I wish I had more flexibility now.”

All three regrets trace back to the same root cause: an insufficient taxable portfolio. Yes, you can use Rule 72(t) to withdraw early from your IRA, but doing so feels awful because it truncates compound growth unless you absolutely have no other choice.

Your Taxable Portfolio Is Your Freedom Engine

Tax-advantaged accounts help you retire by 60. A taxable portfolio lets you retire before 60.

If you want true autonomy – the ability to walk away from a bad boss, spend more time with your kids, pursue passion projects, relocate when you want, or simply protect your spouse from unwanted work – your taxable portfolio is the key.

Build it deliberately. Build it consistently. And build it large enough that it becomes impossible for your future self to feel regret.

If you follow the three rules – avoid catastrophic loss, don’t extrapolate income forever, and aggressively build your taxable portfolio – you’ll reach financial independence not by luck, but by design.

Readers, are you actively building your taxable brokerage portfolio? If not, why not?

Get Your Year-End Financial Checkup

One tool I’ve leaned on since leaving my day job in 2012 is Empower’s free financial dashboard. It remains a core part of my routine for tracking net worth, investment performance, and cash flow.

My favorite feature is the portfolio fee analyzer. Years ago it exposed that I was paying about $1,200 a year in hidden investment fees – money that’s now compounding for my future instead of someone else’s.

If you haven’t reviewed your investments in the last 6–12 months, now’s the perfect time. You can run a DIY checkup or get a complimentary financial review through Empower. Either way, you’ll likely uncover useful insights about your allocation, risk exposure, and investing habits that can lead to stronger long-term results.

Stay proactive. A little optimization today can create far greater financial freedom tomorrow.

Empower is a long-time affiliate partner of Financial Samurai. I've used their free tools since 2012 to help track my finances. Click here to learn more.

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Markw
Markw
1 month ago

The more I read about this fire concept, the less I understand it. Why just not keep working but build safety nest so large you can actually find the job you want or are able to work stress free knowing you can live years if you get laid off?

Markw
Markw
1 month ago

I dont think there is a dream job. Instead, its easier to try to learn to love whatever brings bread to your table.

ryan thurston
ryan thurston
1 month ago

Something really important to consider…long term cap gains on brokerage accounts is ZERO percent if your TOTAL taxable income falls below certain limits. In 2025 the limit is $96,700 (married filing jointly). Add to that your $31,500 standard deduction and you can walk away making $120,000+ paying ZERO FEDERAL TAXES!!!

Marina
Marina
1 month ago

This is a great topic as bridging financial needs before retirement age is often overlooked. My husband and I retired early and were hit with health insurance premiums of ~$1600/month. Retiring early was a bit scary at first, but then I realized it was largely an exercise in managing cash flow. We had assets but not enough cash. I rearranged our finances to boost monthly cash flow as follows:

We sold one rental property and a piece of land. We used the proceeds and some savings to pay off 4 rental properties. We also paid off our primary home before that. This boosted cash flow since we don’t have to pay mortgages. The rental income (with no mortgages) provides a good supplement to my husband’s pension. I’m finding that we don’t need to withdraw anything more from our savings /stock funds.

I realized that we will face a different problem once we get social security and RMDs: more income with heavier taxation. And further, once one of us dies, the remaining spouse will be in a much higher tax bracket. Due to this, I am now starting to convert my IRA to a ROTH, which will not have RMDs. But, I wish that I started this earlier in my lower income years before full retirement age. I wasn’t prepared for this… it would be a great topic for a future article.

We live frugally, and its an adjustment to begin spending down our savings. We have decided to start gifting more $ to our adult children to help with launching their lives.

Marilia
Marilia
1 month ago

Would you suggest to prioritize the taxable portfolio over mega backdoor contributions? Both partner and myself can add up to $70k per person to our 401k thanks to mega backdoor contributions. We have been doing that and deprioritizing our taxable portfolio. Should we change strategies? If so, when?

Brent
Brent
1 month ago

Interesting article.

Something in your table seems very off though if you are saying a 40 year old with $1.5MM in net worth and $1MM in post tax assets can retire (seems quite risky!) but a 60 year old would require $10MM net worth and $7MM in post tax assets!?!

Last edited 1 month ago by Brent
Brent
Brent
1 month ago

I’m well familiar the concept of compounding. I’m still working full time at age 48 but feel reasonably well positioned for retirement by 60ish if not sooner. As I’ve been the single earner of a modest salary ($140Mish) for the family the past 13 years with 2 kids it hasn’t always been easy though. Net retirement assets combined with wife about $1MM with $300 of that in roth and about $500M in post-tax “liquid accounts.” House worth about $900M and has $180M left of mortgage locked in at a low rate as the only debt. Net worth somewhere around $2.2MM. Live in a modestly expensive area (Portland, OR) but not high expense.
I still am questioning how a 40 year old could retire with that level of NW in your chart compounding including or not. Is that assuming just a $40M yearly expense level indefinitely after 40? If so, seems unrealistic.

Denys
Denys
1 month ago

Sam, thank you for the interesting article. I was wondering if you were planning at some point to provide readers with an update on how your private real estate investment portfolio is doing. I recall you mentioned that you had ~800K invested in private real estate deals either directly thru crowdfunding platforms or syndicate funds, but i am curious to hear your perspective on how your investments have been doing so far as of the end of 2025. Thanks!

Denys
Denys
1 month ago

As far as the topic of your post is concerned, while i agree that having taxable accounts are important, there are a few alternatives that people also can rely on when funding their needs, such Health Savings Accounts (HSAs) , roth conversions which can provide penalty-free access under certain conditions, 72(t)/SEPP withdrawals with early access to retirement funds without penalty or smth like laddered bonds or cash reserve strategies for bridging liquidity needs. Your lifestyle cost examples may be too subjective. For instance, things like a new car or independent school tuition feel anecdotal and subjective: these are lifestyle choices, not universal necessities, and framing them as obligations can unnecessarily broaden the FIRE goalposts. Not everyone planning FIRE has children or aspires to a high-spending lifestyle. From a pure planning standpoint, backward engineering expenses (e.g., using a safe withdrawal rate and spending projection) often yields a more consistent model than adding examples that may not apply to every reader. You implicitly assume that most people want a relatively high-liquidity lifestyle and expensive goods rather than lean retirement lifestyles. Many folks in the FIRE community embrace lean FIRE or barista FIRE (part-time work + portfolio income) precisely to avoid large taxable portfolios. In other words, you frame coast FIRE as almost an illusion rather than a valid intermediate strategy for some. This lack of nuance fails to recognize diverse personal circumstances and spending philosophies.
As far as my curiosity about your passive real estate investment portfolio is concerned, i was mainly wondering whether your conviction bet that properties in Sunbelt region such as Texas, Florida, Arizona and such are going to do meaningfully better than NE and California bore the fruit for you or you have reasons to believe that it did not pay off and which RE asset classes based on your experience fared relatively better (multifamily, storage, hospitality, industrial, office, etc). I think readers would be definitely interested in your follow-up on this given that your net worth had a significant exposure to this asset class compared to many of other readers.

WC
WC
1 month ago

Great article Sam! I too am stuck with large amounts in my tax advantaged accounts and very little in my taxable account. What are your thoughts on doing using a 72t or SEPP to access funds in a tax advantaged accounts. Why is this not talked about more? Would love your thoughts?

WC
WC
1 month ago

The goal of using a 72t would be so I could retire or at least slow down around 10 years prior to 59.5. I get that it feels bad to draw down your hard earned savings. Like you have said I’m not afraid to go back to work and I’ll save a dollar before I will spend it. I just want the option to slow down as well. I guess I feel a bit hesitant to use the 72t because it just seems like an option that no one talks about. Are there hidden risks other than you can stop the withdrawals until 59.5. What am I missing? It seems like a great tool for someone who wants to FIRE or Coast FIRE!

Bridget
Bridget
1 month ago
Reply to  WC

This is the best breakdown I have read about the advantages/disadvantages of various methods of getting to your retirement money ahead of 59.5. https://www.madfientist.com/how-to-access-retirement-funds-early/ It really got me thinking. There truly are a lot of factors in your personal situation to consider. I, myself, generally follow simpler strategies even if I know I might lose money in the process. :) My taxable accounts are fairly low, too, so I spend a lot of time thinking about this like you.

SG
SG
1 month ago

Sam is your table for taxable portfolio goals per person or per household (ie 2x if both spouses work) ?

SG
SG
1 month ago

Sam – quick question. Is your table of net worth and taxable portfolio per household, or is it per person (ie double if both spouses are working in a typical West Coast household with 2 teenage kids). In general it’s something I get confused by in online articles since both of us are working and contributing to retirement accounts and networth, but the tables don’t clarify whether the numbers are per household or per person

RetireSoon
RetireSoon
1 month ago

Have 250k taxable account, 750K Roth IRA, $2M 401K 60%Roth401K 40%Trad401K. 55 yo, wife retired 12 years ago. No debt and kids college, first cars, and two weddings paid for. Moved from high stress medical job after Covid to digital health remote job management position. Thinking of flexing rule of 55 since taxable is low and out in next year or so. $120k a year expenses LCOL Midwest. Can see myself falling into “one more year” but Boldin type calculators thought to get an answer and even a fiduciary review seems to weight towards working until 65 (no thank you). I don’t think 56 is considered FIRE but hoping can make numbers work.

RetireSoon
RetireSoon
1 month ago

Not really saving for anything, our youngest will go to college next year and then we’ll be empty nesters. The retirement models/monte carlos always have me confused if I have enough, and the financial planner we met with wasn’t helpful, I might try the Empower overview since my retirement accounts are there and I and have done my net worth tracking there (since the personalcapital.com days). Your website has been such a blessing to my family in my DIY journey and I have passed it along (along with your book) to my two married children and their spouses. Hang in there with raising the small children, it’s stressful on the marriage, but so worth it. The days are long but the years fly by. I envy your position, men with young children have such a real and singular purpose and having them all under one roof is so fleeting you won’t believe how fast it goes by! Cheers and have a wonderful holiday season!

Todd
Todd
1 month ago
Reply to  RetireSoon

Hey Sam,

Great stuff as usual!

I retired 6 months ago (at age 59) when I finally realized I didn’t need to work anymore. The PE firm that bought my company was morphing into all the worst cliches and it was just not worth the grind anymore.

That being said, one of the most important financial pitfalls I became aware of is IRMAA and RMDs. Fortunately I have plenty of time to convert my Traditional IRAs to Roths at controlled tax rate over the next 3 years.

My Trad IRA balance in NOV25 was $477K which doesn’t seem terrible, but I ran some numbers and realized that if I never converted I’d be facing significant tax hits in my 70s due to RMDs and also Medicare IRMAA surcharges since I wouldn’t be able to avoid an income in the 28% bracket (or maybe higher).

This is because I won’t need to the IRA principle due to a healthy taxable account position, and PE investments that will mature over the next 3 to 5 years. I was forecasting $800K to $1000K in additional taxes and IRMAA surcharges over a 15 year period, that are avoided by converting Trad IRAs to Roths while my income is relatively low for the next few years.

Have you ever dug into this potential time bomb?

WannaFire
WannaFire
1 month ago

Well, I maxed out my pre-tax, roth first then my taxable – in that order. I don’t have enough income to make the ratio to be 3 x.

What I have now at 50 is 3 m pre, 1 m roth and 1 m taxable. Should I re prioritize taxable now?

Jamie
Jamie
1 month ago

This makes a lot of sense. Out of all of my accounts, my after tax investment account is the largest. For me it’s because of the contribution limitations on my retirement accounts and my own choice to “pay myself first” in my investment account before spending on random things with my disposable income. Even though it’s not actually forced savings, I try to treat it that way. It’s helped a lot!

PNWGuy
PNWGuy
1 month ago

So true, building a taxable portfolio is critically important to financial independence. I figured that out a bit later than I should have, starting in my mid 40s. Fortunately, I did accumulate sufficient after tax assets, allowing my pretax assets grow my first years of retirement. I continue timing starting to pull pre tax assets, it’s almost like playing whack-a-mole with so many variables to consider. Good problem to have, but challenging to manage.

You might consider a fourth rule of financial independence: Marry well and do not get a divorce. That one cost me few years to a later FIRE, among other things.

PNWGuy
PNWGuy
1 month ago

There was more than one contributor to the marriage failing. We mutually agreed the marriage was over. Money wise, sense of entitlement was a big issue, and a belief that what we had was never enough, though it certainly was plenty. Divorce is a huge financial and emotional drain, whatever the reasons.

Joe B
Joe B
1 month ago

Sounds like you may need a period to detox Sam, digital detox is interesting as well as vacant time of not doing but just to be! Nature also heels, getting ones feet in the sand and to take walk in the forest. Hard to always keep moving within society, taking a pause is important to align and allow renewed energy.

PNWGuy
PNWGuy
1 month ago

Sam, thanks, things are way better now. Divorce is the best $1.4M I’ve ever spent. . Best to you and your family.