The Tax Time Bomb in My Retirement Plan: How an Epiphany from Urban Planning Led Me to the Roth IRA

For the first decade of my career as a financial professional, I thought I had it all figured O.T. I followed the playbook to the letter: I diligently contributed the maximum amount to my employer-sponsored 401(k) to capture the full company match, and every year, I faithfully funded a Traditional IRA.

The immediate tax deduction felt like a victory, a tangible reward for my discipline.

Watching my taxable income drop each year was satisfying, and my retirement accounts grew at a steady clip.

On paper, I was building the perfect nest e.g.¹

But beneath the surface of those reassuring quarterly statements, a quiet anxiety began to grow.

It was a vague, persistent feeling that I couldn’t quite name, a sense of building a beautiful house on a foundation I didn’t fully trust.

The larger my portfolio became, the more this unease intensified.

My savings, I realized, were inextricably entangled with a future, unknowable variable: the United States tax code.

The breaking point came one Tuesday evening.

I was running a new set of retirement projections, and for the first time, I modeled the future tax liability on my “perfect” plan.

The number that stared back at me was staggering.

A huge portion of what I considered “my” money was, in reality, a deferred liability owed to the IRS. It was a tax time bomb, ticking silently at the core of my financial future.

This wasn’t just a number; it was an “emotional tax”.³

Research has long shown that economic uncertainty and deferred financial obligations create significant psychological distress, leading to cognitive misperceptions where we systematically underestimate future burdens.⁴

That night, I felt the full weight of that burden.

I was saving for a future I couldn’t clearly see, shackled to a tax bill I couldn’t predict.

My perfect plan felt like a trap, and I knew I had to find a better Way.

The Illusion of the Standard Path — Why My 401(k) Felt Like a Hidden Trap

The conventional wisdom surrounding retirement savings is seductive for a reason.

The core argument for tax-deferred accounts like the Traditional 401(k) and Traditional IRA centers on a simple premise: get a tax break now, when you’re in your high-earning years, and pay the taxes later in retirement, when your income—and thus your tax bracket—is presumably lower.⁷

This strategy of paying tax on the large “harvest” rather than the small “seed” seems logical, and the immediate gratification of a lower tax bill today is a powerful motivator.²

However, as my own experience showed, this path is riddled with hidden complexities and frustrations that erode a saver’s sense of control.

My 401(k), the supposed cornerstone of my retirement, began to feel less like a secure vault and more like a system designed for the benefit of others.

The investment options were often limited to a small, curated list of funds, a stark contrast to the universe of choices available in an individual account.¹

Worse, these plans are often laden with layers of hidden fees—administrative fees, investment management fees, 12b-1 fees—that silently eat away at returns.

A U.S. Government Accountability Office study found that 41% of American workers don’t even know they’re paying fees in their 401(k).¹⁰

A seemingly small 1% difference in annual fees can reduce a final retirement balance by as much as 28% over a 35-year period.¹²

This lack of transparency is compounded by administrative complexity.

Plan documents are often dense and confusing, making it difficult to understand the rules for eligibility, loans, and distributions.¹³

Furthermore, the employee is entirely dependent on the employer’s competence and integrity.

If an employer is late remitting contributions from payroll, for example, employees can miss out on market gains through no fault of their own.¹⁶

These frustrations, however, were merely symptoms of the deeper, core flaw in the tax-deferred model.

Every dollar of growth in my 401(k) and Traditional IRA wasn’t a pure gain; it was simultaneously expanding my future tax liability.

I was diligently building a bigger and bigger tax problem for my future self.

The system that promised security was, in fact, built on a foundation of profound uncertainty, leaving me with responsibility for my retirement but without full control over the outcome.

The Epiphany — A Surprising Lesson from Urban Planning

My search for a solution led me to an unexpected place: the world of urban planning.

While reading about the challenges of modern infrastructure, I stumbled upon a powerful analogy that instantly clarified the problem with my retirement strategy.

It reframed the entire debate from a simple question of tax timing to a profound choice between risk and certainty.

Here is the epiphany that changed everything:

A Traditional IRA or 401(k) is like building a magnificent city on top of old, unmapped, and decaying utility pipes. From the street level, the city—your retirement portfolio—looks impressive.

The skyscrapers of your stock funds and the solid municipal bonds all contribute to a picture of wealth and stability.

But underneath it all lies a foundation of deferred tax liability, a network of pipes whose true condition is unknown.

You don’t know what the repair costs (future tax rates) will be in 10, 20, or 30 years.

You don’t know if the system can handle the strain of your retirement needs.

Every time you want to tap into the city’s resources—making a withdrawal—you risk digging into a corroded main, triggering a catastrophic and expensive failure in the form of a massive, unexpected tax bill.

The city’s true, usable value is an illusion.

A Roth IRA, by contrast, is like building a modern city where you make a massive, upfront investment in the infrastructure. Before the first building is erected, you pay the full cost to install the most advanced, durable, and perfectly mapped foundation imaginable—fiber-optic cables, high-capacity water mains, a resilient power grid.

The initial cost is higher and more painful; you pay your taxes today, with after-tax money.

But once that foundation is paid for, it is yours.

It is solid, predictable, and fully under your control.

Now, your city can grow and expand for decades.

The skyscrapers can reach incredible heights, and you can tap into any of its resources at any time, for any reason, with absolute confidence that the system will work.

There is no fear of a hidden, systemic collapse.

All future use is effectively “free” because the fundamental cost has already been paid.

This analogy was a revelation.

It shifted my entire perspective.

The question was no longer, “Will taxes be higher or lower in the future?” The question became, “Do I want to build my future on a foundation of certainty or a foundation of risk?” The true power of the Roth IRA, I realized, wasn’t just about tax-free withdrawals.

It was about de-risking my entire retirement plan by surgically removing the single largest, most unpredictable variable: the future of U.S. tax policy.¹⁸

The Roth IRA Blueprint — Building a Retirement on a Solid Foundation

Armed with this new “urban planning” framework, I began to see the features of the Roth IRA not as a random list of benefits, but as the deliberate design principles of a superior system.

Each element contributes to a structure of unparalleled strength and predictability.

Paying for the “Pipes” Upfront (After-Tax Contributions)

The foundational principle of the Roth IRA is that contributions are made with after-tax dollars.²⁰

You don’t get an upfront tax deduction.

This is the primary “con” of the Roth model and the price of admission.²²

It is the conscious decision to pay for your financial infrastructure today to secure a tax-free future.

A Resilient, Tax-Proof Grid (Tax-Free Growth)

Once your contribution is inside the Roth IRA, it enters a protected ecosystem.

All potential growth—from capital gains, dividends, and interest—accumulates completely free from federal taxes.²²

This is the financial equivalent of the snowball effect, where your money makes money, and the money that money makes also makes money, all without the drag of annual taxation.²⁵

The story of tech investor Peter Thiel, who reportedly grew a small Roth IRA into a multi-billion-dollar fortune by investing in private shares of companies like PayPal and Facebook, is an extreme but powerful illustration of what is possible when explosive growth happens within a tax-free wrapper.²⁷

Predictable Utilities (Tax-Free Qualified Withdrawals)

This is the ultimate payoff.

After age 59.5, and as long as your account has been open for five years, every dollar you withdraw—both your original contributions and all the accumulated earnings—is 100% tax-free.²³

This provides a level of predictability that is impossible with tax-deferred accounts.

The number you see on your statement is the number you actually get to spend.

This transforms retirement income planning from guesswork into a clear, manageable calculation.

Flexible Zoning (No Required Minimum Distributions)

Unlike Traditional IRAs and 401(k)s, Roth IRAs have no Required Minimum Distributions (RMDs) during the original owner’s lifetime.¹⁸

The government cannot force you to start liquidating your assets and realizing income on its schedule.

This gives you complete control over your financial city.

You decide when and how to use your assets, allowing them to continue growing tax-free for as long as you live.

This feature also makes the Roth IRA an exceptionally powerful estate planning tool, as you can pass the entire account to your heirs, who can then take tax-free withdrawals.¹⁸

Emergency Access Hatches (Flexible Contribution Withdrawals)

The Roth IRA is designed with a unique layer of flexibility.

You can withdraw your direct contributions (not the earnings) at any time, for any reason, without paying taxes or penalties.³²

While you should always view retirement funds as sacrosanct, this feature effectively allows your Roth contributions to serve as a final-tier emergency fund, providing a level of liquidity and peace of mind that traditional accounts lack.

This combination of features creates a strategic advantage that goes far beyond the simple “pay taxes now” analysis.

In retirement, your income is not static; you have some control over it.

RMDs from traditional accounts are mandatory, forcing you to take taxable distributions that can push you into a higher tax bracket, trigger taxes on your Social Security benefits, or increase your Medicare premiums.³⁵

A Roth IRA provides a pool of tax-free capital.

This allows you to engage in “tax-rate arbitrage” in retirement: you can withdraw from your taxable 401(k) or Traditional IRA just enough to fill up the lower tax brackets, then draw any additional income you need from your Roth IRA, completely tax-free.¹⁸

The Roth IRA becomes a strategic tool for actively managing your tax liability throughout your retirement, a sophisticated benefit that a portfolio of purely tax-deferred accounts simply cannot offer.

A Tale of Two Cities — Roth vs. Traditional in the Real World

Choosing between a Roth and a Traditional IRA is fundamentally a choice between two different city plans.

The traditional plan offers an immediate benefit—the tax deduction—but builds a future liability.

The Roth plan requires an upfront cost but delivers future certainty.

The classic question is whether to pay tax on the “seed” (your initial contribution) or the “harvest” (your withdrawals in retirement).⁸

The traditional model bets that the harvest will be taxed at a lower rate.

But this is a significant gamble on an unknown future.

Unless you are highly confident that your tax rate in retirement will be substantially lower than it is today, the more prudent, risk-averse strategy is to pay the known tax on the smaller seed now, rather than an unknown tax on the much larger harvest later.

Your personal situation dictates which plan is more suitable:

• For the Young Professional: You are likely in the lowest tax bracket of your career. Your income and tax rate will almost certainly rise in the future. For you, the Roth IRA is the clear and obvious choice. Paying taxes now at a low rate to secure decades of tax-free growth is an unparalleled financial opportunity.³¹
• For the Peak Earner: Your income may be too high to contribute to a Roth IRA directly. The immediate tax deduction of a Traditional IRA is very tempting. However, the benefits of tax diversification and having a tax-free bucket of money in retirement are immense. High earners can still access the Roth IRA through the “Backdoor Roth IRA” strategy, which involves making a non-deductible contribution to a Traditional IRA and then immediately converting it to a Roth.³⁷
• For the Pre-Retiree: The years between stopping work and starting Social Security or RMDs present a golden opportunity. In these “gap years,” your taxable income may be very low. This is the ideal time to execute strategic Roth conversions, moving money from your Traditional IRA or 401(k) to a Roth IRA and paying taxes at a temporarily low rate. This “fills up” your lower tax brackets and reduces the size of your future RMDs, lowering your lifetime tax bill.³⁵

To make the choice clearer, here is a direct comparison:

Table 1: Roth IRA vs. Traditional IRA: A Head-to-Head Comparison

Feature	Roth IRA	Traditional IRA
Tax Treatment of Contributions	After-tax; no upfront deduction 7	Pre-tax; contributions may be tax-deductible 7
Tax Treatment of Growth	Tax-free 22	Tax-deferred 7
Tax Treatment of Qualified Withdrawals	100% tax-free 30	Taxed as ordinary income 7
Required Minimum Distributions (RMDs)	No RMDs for the original owner 18	RMDs required starting at age 73 23
Income Limits for Direct Contribution	Yes, based on MAGI 23	No, anyone with earned income can contribute 42
Withdrawal of Contributions	Can be withdrawn anytime, tax-free and penalty-free 32	Taxed and penalized if withdrawn before age 59.5 23
Best For…	Those who expect to be in a similar or higher tax bracket in retirement; those who value tax certainty and flexibility.7	Those who are certain they will be in a significantly lower tax bracket in retirement and need the tax deduction now.7

Navigating the City Limits — Understanding Roth Rules and Boundaries

Every well-designed city operates under a set of zoning laws and building codes.

The Roth IRA is no different.

To ensure your financial city is built to last, you must understand and adhere to the rules set by the IRS.

Contribution Limits

For the tax years 2024 and 2025, you can contribute up to $7,000 per year to an IRA.

If you are age 50 or older, you can make an additional “catch-up” contribution of $1,000, for a total of $8,000.⁴⁴

It’s crucial to remember that this is a combined limit that applies across

all of your IRAs, both Roth and Traditional.

You cannot contribute $7,000 to a Roth and another $7,000 to a Traditional IRA in the same year.⁴³

Income “Zoning” (MAGI Limits)

The IRS restricts who can contribute directly to a Roth IRA based on their Modified Adjusted Gross Income (MAGI).

These limits exist to prevent the Roth from being used as a tax shelter primarily by high-income individuals.⁴⁷

If your income falls within a specific “phase-out” range, your maximum contribution is reduced.

If it exceeds the range, you cannot contribute directly at all.

Table 2: Roth IRA Contribution & Income Limits (2024 & 2025)

Filing Status	2024 MAGI	2024 Contribution Limit	2025 MAGI	2025 Contribution Limit
Single, Head of Household	< $146,000	Full ($7,000 / $8,000)	< $150,000	Full ($7,000 / $8,000)
	$146,000 – $161,000	Reduced	$150,000 – $165,000	Reduced
	≥ $161,000	$0	≥ $165,000	$0
Married Filing Jointly	< $230,000	Full ($7,000 / $8,000)	< $236,000	Full ($7,000 / $8,000)
	$230,000 – $240,000	Reduced	$236,000 – $246,000	Reduced
	≥ $240,000	$0	≥ $246,000	$0
Married Filing Separately*	$0 – $10,000	Reduced	$0 – $10,000	Reduced
	≥ $10,000	$0	≥ $10,000	$0
*Source:.43	Applies if you lived with your spouse at any time during the year.

Building Permits (Withdrawal Rules)

The rules for withdrawing money from a Roth IRA are precise and depend on whether you are withdrawing contributions or earnings.

Table 3: Qualified Roth IRA Withdrawals: The Rules of the Road

Type of Money Withdrawn	Taxable?	10% Penalty?	Conditions / Notes
Direct Contributions	No	No	Can be withdrawn at any time, for any reason. The IRS treats withdrawals as coming from contributions first.32
Conversion Contributions	No	Yes, if withdrawn within 5 years of conversion, unless you are over 59.5.	Each conversion has its own 5-year holding period to avoid the 10% penalty.22
Earnings (Growth)	Yes, unless it’s a “Qualified Distribution”	Yes, unless it’s a “Qualified Distribution”	A withdrawal of earnings is “Qualified” (tax- and penalty-free) ONLY if BOTH conditions are met: 1. The account has been open for at least 5 years. 2. You are age 59.5 or older (or meet other exceptions like death or disability).30

The “5-Year Rule” for the account begins on January 1st of the tax year for which you made your very first contribution to any Roth IRA.⁴⁰

This is a crucial point: once that clock has started, it applies to all your Roth IRAs.

Common Pitfalls — Avoiding the Sinkholes in Your Financial City Plan

Even the best-laid city plans can fail if you’re not careful.

I’ve seen many well-intentioned savers make costly mistakes that undermine the integrity of their Roth strategy.

Here are the most common sinkholes to avoid.

Mistake 1: The Empty Lot (Not Investing Contributions)

This is the most basic yet surprisingly common error.

You open a Roth IRA, diligently contribute money…

and then do nothing.

The cash sits in a money market or settlement account, uninvested.

The primary power of the Roth IRA is tax-free growth.

If the money isn’t invested in assets like stocks or funds, there is no growth to be shielded from taxes, completely defeating the purpose.53

Mistake 2: Ignoring the Pro-Rata Rule (The Backdoor Roth Trap)

For high-income earners using the Backdoor Roth strategy, this is the most dangerous pitfall.

The IRS “aggregation rule” requires that when you convert money from a Traditional IRA to a Roth IRA, you must consider all of your pre-tax IRA assets (including Traditional, SEP, and SIMPLE IRAs) as one giant pool.55 The conversion is then taxed “pro-rata,” or proportionally.

If you have a large pre-tax IRA balance and try to convert a small, non-deductible contribution, a large portion of that conversion will be taxable, turning your clever tax-free maneuver into an unexpected tax bill.37

Mistake 3: Accidental Over-Contribution

If your income unexpectedly rises during the year, or you simply misunderstand the limits, you might contribute more than you’re allowed.

This excess contribution is subject to a 6% penalty tax for every year it remains in the account.

You must withdraw the excess amount, plus any earnings it generated, before the tax filing deadline to avoid the penalty.53

Mistake 4: Misunderstanding the 5-Year Rules

The 5-year rules are a common source of confusion.

There are two distinct rules to track.

First, there is the single, overarching 5-year clock on the account itself, which must be met to withdraw earnings tax-free.

Second, each Roth conversion has its own separate 5-year clock.

If you withdraw converted funds before that specific 5-year period is up (and you are under age 59.5), the withdrawal could be subject to the 10% early withdrawal penalty.33

Mistake 5: Forgetting to Name Beneficiaries

One of the most powerful features of a Roth IRA is its ability to pass wealth to the next generation tax-free.

However, if you fail to designate primary and contingent beneficiaries, your account may have to go through the costly and lengthy probate process upon your death.

This can completely derail your estate planning intentions and create a major headache for your loved ones.51

Conclusion: The Peace of Mind of a Well-Built Future

My journey from the nagging anxiety of the “tax time bomb” to the quiet confidence of a predictable retirement plan was transformative.

It led me to understand that the Roth IRA is more than just a type of account; it’s a financial philosophy.

It is a conscious choice to favor certainty over ambiguity, control over dependency, and clarity over complexity.

The process of saving for retirement is deeply emotional.

It is a decades-long journey filled with hope, discipline, and no small amount of fear.⁵⁸

By eliminating the “emotional tax” of future tax uncertainty, the Roth IRA clears away one of the biggest psychological hurdles.

It allows you to plan with confidence, knowing that the money you’ve saved is truly yours.

This mental freedom allows you to focus on what retirement is really about: finding new purpose, deepening relationships, and pursuing a life of well-being.⁶¹

Adopting the “urban planning” mindset means proactively designing a financial future built on a resilient and predictable foundation.

It means refusing to leave your security to the shifting winds of future politics and tax policy.

A famous proverb says that the best time to plant a tree was 20 years ago.

The second-best time is now.⁶⁴

The same is true for laying the foundation of your financial city.

The sooner you start building on solid ground, the more magnificent and secure your future will be.

Works cited

1. IRA vs. 401(k): What’s the difference and how to choose one – Citizens Bank, accessed August 7, 2025, https://www.citizensbank.com/learning/ira-vs-401k.aspx
2. IRA vs. Roth IRA vs. 401k: Key Differences – SmartAsset.com, accessed August 7, 2025, https://smartasset.com/retirement/ira-vs-roth-ira-vs-401k-key-differences
3. The Emotional Tax of Deficit Thinking – Stanford Social Innovation Review, accessed August 7, 2025, https://ssir.org/articles/entry/the_emotional_tax_of_deficit_thinking
4. Effect of Expanding the Earned Income Tax Credit to Americans Without Dependent Children on Psychological Distress: The Paycheck Plus Health Study Randomized Controlled Trial – Oxford Academic, accessed August 7, 2025, https://academic.oup.com/aje/article/191/8/1444/6292354
5. Essays on the Effects of Deferred Taxation and Tax Audit Negotiations – Repository of Leibniz Universität Hannover, accessed August 7, 2025, https://www.repo.uni-hannover.de/bitstream/handle/123456789/10385/Dissertation_Milde.pdf?sequence=1&isAllowed=y
6. How does income affect mental health and health behaviours? A quasi-experimental study of the earned income tax credit | Journal of Epidemiology & Community Health, accessed August 7, 2025, https://jech.bmj.com/content/75/10/929
7. Roth IRA vs. Traditional IRA: Differences and Rules – Charles Schwab, accessed August 7, 2025, https://www.schwab.com/ira/roth-vs-traditional-ira
8. Which is Better: Roth IRA or Traditional IRA? – Morrissey Wealth Management, accessed August 7, 2025, https://www.morrisseywealthmanagement.com/blog/which-is-better-roth-ira-or-traditional-ira
9. I Absolutely Prefer a Roth IRA to a 401(k) for Retirement Savings. Here’s Why., accessed August 7, 2025, https://www.fool.com/retirement/2025/03/09/i-absolutely-prefer-a-roth-ira-to-a-401k-for-retir/
10. Changing Jobs? How to Protect Your 401(k) from Hidden Fees | The Motley Fool, accessed August 7, 2025, https://www.fool.com/retirement/2025/07/30/changing-jobs-how-to-protect-your-401k-from-hidden/
11. 401(k) Fees: Everything You Need to Know – Investopedia, accessed August 7, 2025, https://www.investopedia.com/articles/personal-finance/061913/hidden-fees-401ks.asp
12. A Look at 401(k) Plan Fees – U.S. Department of Labor, accessed August 7, 2025, https://www.dol.gov/sites/dolgov/files/ebsa/about-ebsa/our-activities/resource-center/publications/401k-plan-fees.pdf
13. Five common 401(k) compliance issues and how to avoid them – BPM, accessed August 7, 2025, https://www.bpm.com/insights/401k-compliance-issues/
14. Five Most Common IRS Red Flags for 401(K) Plans – Langan Financial Group, accessed August 7, 2025, https://langanfinancialgroup.com/fix-401k-five-common-irs-red-flags/
15. Three Common Problems With 401(k) Plans | EVOadvisers, accessed August 7, 2025, https://evoadvisers.com/three-common-problems-with-401k-plans/
16. The 4 Most Common Retirement Plan Errors – First Business Bank, accessed August 7, 2025, https://firstbusiness.bank/resource-center/the-4-most-common-retirement-plan-errors/
17. Ten Warning Signs That Your 401(k) Contributions Are Being Misused – U.S. Department of Labor, accessed August 7, 2025, https://www.dol.gov/sites/default/files/ebsa/about-ebsa/our-activities/resource-center/publications/ten-warning-signs-that-your-401k-contributions-are-being-misused.pdf
18. 9 compelling Roth IRA benefits – Fidelity Investments, accessed August 7, 2025, https://www.fidelity.com/learning-center/personal-finance/retirement/nine-reasons-roth
19. Rethinking the Roth IRA | Creative Planning, accessed August 7, 2025, https://creativeplanning.com/insights/taxes/rethinking-the-roth-ira/
20. www.schwab.com, accessed August 7, 2025, https://www.schwab.com/ira/roth-ira#:~:text=A%20Roth%20IRA%20is%20a,your%20money%20grows%20tax%2Dfree.
21. Roth IRA: What It Is and How to Open One – Investopedia, accessed August 7, 2025, https://www.investopedia.com/terms/r/rothira.asp
22. What is a Roth IRA? | Charles Schwab, accessed August 7, 2025, https://www.schwab.com/ira/roth-ira
23. Roth IRA vs. traditional IRA: Eligibility, rules, and tax benefits – Vanguard, accessed August 7, 2025, https://investor.vanguard.com/investor-resources-education/iras/roth-vs-traditional-ira
24. What is a Roth IRA: Tax Benefits and How it Works – TIAA, accessed August 7, 2025, https://www.tiaa.org/public/retire/financial-products/iras/roth-ira
25. What is compound interest? Understand the snowball effect – Unividual, accessed August 7, 2025, https://unividual.co.uk/news/faq/what-is-compound-interest/
26. Analogies to help understand investing – Raiz, accessed August 7, 2025, https://raizinvest.com.au/blog/investing-analogies/
27. The Peter Thiel Roth IRA Strategy: How He Built a $5 Billion Tax-Free Retirement Account, accessed August 7, 2025, https://equifund.com/blog/peter-thiel-roth-ira/
28. Choosing The Right Investment Strategy With A Roth IRA – Prime Capital Financial, accessed August 7, 2025, https://primefinancial.com/choosing-the-right-investment-strategy-with-a-roth-ira/
29. Invest in a Company the Peter Thiel Way with a Self-Directed Roth IRA – IRA Financial, accessed August 7, 2025, https://www.irafinancial.com/blog/invest-in-a-company-the-peter-thiel-way-with-a-self-directed-roth-ira/
30. Roth IRA Withdrawal Rules – NerdWallet, accessed August 7, 2025, https://www.nerdwallet.com/article/investing/roth-ira-withdrawal-rules
31. Unlocking the power of Roth IRAs – Merrill Lynch, accessed August 7, 2025, https://www.ml.com/articles/unlocking-the-power-of-roth-iras.html
32. investor.vanguard.com, accessed August 7, 2025, https://investor.vanguard.com/investor-resources-education/iras/ira-withdrawal-rules#:~:text=Withdrawals%20of%20Roth%20IRA%20contributions,earnings%20portion%20of%20the%20withdrawal.
33. Roth IRA withdrawal rules | Empower, accessed August 7, 2025, https://www.empower.com/the-currency/life/roth-ira-withdrawal-rules
34. Roth IRA vs. 401(k): What’s the difference? – Fidelity Investments, accessed August 7, 2025, https://www.fidelity.com/learning-center/smart-money/roth-ira-vs-401k
35. I’m a Financial Professional: This Is the Roth Conversion Mistake Too Many People Make, accessed August 7, 2025, https://www.kiplinger.com/retirement/roth-iras/the-roth-conversion-mistake-too-many-people-make
36. Should I open a Roth IRA? – BenefitsLink, accessed August 7, 2025, https://benefitslink.com/boards/topic/34518-should-i-open-a-roth-ira/
37. Backdoor Roth: Standard and Mega – The White Coat Investor, accessed August 7, 2025, https://www.whitecoatinvestor.com/backdoor-roth-standard-and-mega-430/
38. Five Things to Consider Before Rolling Your 401(k) into a Roth IRA – Kiplinger, accessed August 7, 2025, https://www.kiplinger.com/retirement/roth-iras/what-to-consider-before-rolling-your-401k-into-a-roth-ira
39. I Have $640k in a 401(k). How Do I Avoid Paying Taxes When Converting to a Roth IRA?, accessed August 7, 2025, https://smartasset.com/retirement/640k-401k-avoid-taxes-convert-to-roth-ira
40. Roth IRA Withdrawal Rules – Investopedia, accessed August 7, 2025, https://www.investopedia.com/roth-ira-withdrawal-rules-4769951
41. Roth IRA Income Limits for 2025 – SmartAsset.com, accessed August 7, 2025, https://smartasset.com/financial-advisor/roth-ira-income-limits
42. Roth comparison chart | Internal Revenue Service, accessed August 7, 2025, https://www.irs.gov/retirement-plans/roth-comparison-chart
43. Roth IRA income and contribution limits for 2025 – Vanguard, accessed August 7, 2025, https://investor.vanguard.com/investor-resources-education/iras/roth-ira-income-limits
44. www.schwab.com, accessed August 7, 2025, https://www.schwab.com/ira/roth-ira/contribution-limits#:~:text=In%202025%20your%20MAGI%20must%20be%20under%20%24236%2C000%20to%20make,re%20age%2050%20or%20older.
45. Roth IRA contribution and income limits for 2024 and 2025 | Fidelity, accessed August 7, 2025, https://www.fidelity.com/learning-center/smart-money/roth-ira-contribution-limits
46. Roth IRA Contribution Limits for 2024-2025 – Charles Schwab, accessed August 7, 2025, https://www.schwab.com/ira/roth-ira/contribution-limits
47. Why IRA, Roth IRA, and 401(k) Contributions Are Limited – Investopedia, accessed August 7, 2025, https://www.investopedia.com/ask/answers/082515/why-are-ira-roth-iras-and-401k-contributions-limited.asp
48. Roth IRA income limits for 2024 and 2025 – Fidelity Investments, accessed August 7, 2025, https://www.fidelity.com/learning-center/smart-money/roth-ira-income-limits
49. Amount of Roth IRA contributions that you can make for 2024 | Internal Revenue Service, accessed August 7, 2025, https://www.irs.gov/retirement-plans/plan-participant-employee/amount-of-roth-ira-contributions-that-you-can-make-for-2024
50. Traditional and Roth IRA Contribution Limits Calculator – TIAA, accessed August 7, 2025, https://www.tiaa.org/public/tools-calculators/ira-contribution-eligibility
51. 15 Common Roth Conversion and Savings Mistakes People Make – Boldin, accessed August 7, 2025, https://www.boldin.com/retirement/roth-ira-mistakes/
52. IRA withdrawals and RMDs | Vanguard, accessed August 7, 2025, https://investor.vanguard.com/investor-resources-education/iras/ira-withdrawal-rules
53. Are You Making These Common Roth IRA Mistakes? – District Capital Management, accessed August 7, 2025, https://districtcapitalmanagement.com/3-common-mistakes-with-roth-iras/
54. Dumb Roth IRA mistake, but is the fix as simple as I think? : r/personalfinance – Reddit, accessed August 7, 2025, https://www.reddit.com/r/personalfinance/comments/1j31ed1/dumb_roth_ira_mistake_but_is_the_fix_as_simple_as/
55. 25. Q&A: Roth IRA 101, Backdoor Roth IRA Contributions, Lifestyle Creep – Apple Podcasts, accessed August 7, 2025, https://podcasts.apple.com/us/podcast/25-q-a-roth-ira-101-backdoor-roth-ira-contributions/id1689450299?i=1000645578504
56. 11 Mistakes to Avoid With Your Roth IRA – Investopedia, accessed August 7, 2025, https://www.investopedia.com/articles/personal-finance/041015/top-10-mistakes-avoid-your-roth-ira.asp
57. Retirement topics – IRA contribution limits | Internal Revenue Service, accessed August 7, 2025, https://www.irs.gov/retirement-plans/plan-participant-employee/retirement-topics-ira-contribution-limits
58. The Emotional Side of Retirement: What to Expect – Brentwood Growth, accessed August 7, 2025, https://www.brentwood-growth.com/blog/retirement-planning/the-emotional-side-of-retirement-what-to-expect/
59. Retirement – My Journey From “No, Never” to “Maybe One Day”, accessed August 7, 2025, https://www.theretirementmanifesto.com/retirement-my-journey-from-no-never-to-maybe-one-day/
60. Preparing for retirement: More than money in the bank – American Psychological Association, accessed August 7, 2025, https://www.apa.org/topics/aging-older-adults/preparing-retirement
61. Your Next Assignment: Embracing the Emotional Journey of Retirement | by Michelle Ogden, accessed August 7, 2025, https://michelle-truewealth.medium.com/your-next-assignment-embracing-the-emotional-journey-of-retirement-964370eccdf3
62. The Emotional Journey: Mentally Preparing for Retirement – SGL Financial Advisors, accessed August 7, 2025, https://www.sglfinancial.com/blog/the-emotional-journey-mentally-preparing-for-retirement/
63. The Psychology of Retirement | Coldstream, accessed August 7, 2025, https://www.coldstream.com/insights/the-psychology-of-retirement/
64. 10 brilliant compound interest quotes that will motivate you to save – Unbiased, accessed August 7, 2025, https://www.unbiased.co.uk/discover/personal-finance/savings-investing/10-brilliant-compound-interest-quotes-that-will-motivate-you-to-save