Curious About a Roth Conversion Strategy? When It Actually Makes Sense (Or Not)

April 17, 2025

“Should I convert my traditional IRA or 401(k) to a Roth?”


If you’ve asked yourself this question lately, you’re in good company. Perhaps you’re a high-earner who makes too much to contribute directly to a Roth IRA but wants access to tax-free growth. Or maybe you’re concerned about future tax rates and want to ensure more tax-free income in retirement.


With market volatility and changing tax laws on the horizon, many of our clients are wondering if a Roth conversion could be a smart money move to save on taxes and provide more flexibility down the road.


While we think Roth conversions are a great strategy, they don’t make sense for everyone. Let’s break down when Roth conversions actually make sense — and when they don’t — in plain English.


Back to Basics: What is a Roth IRA?


Before we dive into strategy, let’s recap the differences between a Roth retirement account and a traditional one.


Traditional retirement accounts, such as a traditional IRA or 401(k), provide you with a tax deduction when you contribute. You save on taxes now, but you’ll pay taxes on that money in the future when you withdraw it as income in retirement.


A Roth IRA allows you to contribute money that you’ve already paid income taxes on. You don’t enjoy savings this year, but the interest you earn on that money grows tax-free, and the withdrawals are 100% tax-free in retirement once you meet certain eligibility requirements. 


For many people, these lifetime tax savings are significantly greater, which is why a Roth conversion is such an intriguing strategy.


What Is a Roth Conversion?


Imagine you’ve been making retirement contributions to a traditional 401(k) for the past 25 years. You’ve enjoyed income tax deductions each year as you squirrel away money for your future.


But as you’re scrolling through your newsfeed one night after dinner, you come across an article about the unexpected tax bills many retirees are faced with in retirement, significantly eating into their retirement income. The article suggests making contributions to a Roth account instead, in order to avoid this scenario in the future.


But you’ve already been making contributions to a traditional account for 25 years. 


Have you missed out?


Not necessarily. With a Roth conversion, you can move money from another retirement account, such as a Traditional IRA or 401(k), into a Roth IRA. Essentially, a Roth conversion allows you to “pre-pay” taxes so your future self won’t have to. For many people, this can be a smart move.


But there are caveats: Convert too much at once, and you might push yourself into a higher tax bracket this year. Convert too little over time, and you might miss opportunities to lower your lifetime tax bill. The challenge lies in finding the right balance.


When Roth Conversions Make Sense


In general, Roth conversions can make sense for individuals in the following circumstances:


1. You’re a High Earner

For 2025, direct Roth IRA contributions are phased out for single filers with incomes between $150,000-$165,000 and for joint files with incomes between $236,00-$246,000. If your income exceeds these thresholds, you can’t contribute directly to a Roth IRA.


However, Roth conversions have no income limits. This creates a powerful opportunity for high-income earners to still enjoy tax-free growth in retirement. By making non-deductible contributions to a traditional IRA (which has no income limits) and then converting those funds to a Roth IRA — often called a “backdoor Roth” — you can effectively circumvent the income restrictions.


2. You’re in a “Tax Valley”

You may be in a “tax valley” if you’re currently experiencing a period where your income is lower than you expect in the future. For example, you may be early in your career, taking a sabbatical from work, or starting a business. These can all be opportune years to make a Roth conversion.


New retirees may also find themselves in a temporary “tax valley.” For example, if you’re recently retired but haven’t yet started collecting Social Security or required minimum distributions (RMDs), this window from your early 60s to 70s could be a golden opportunity to convert portions of your traditional retirement savings into a Roth.


By strategically moving money over a few years, you can fill up the lower tax brackets and reduce your future RMDs, which might otherwise push you into a higher bracket later. This can also help reduce the tax burden on your Social Security benefits once you begin collecting them.


3. You Have a Long Time Horizon 

Younger investors in their 30s and 40s may benefit from a Roth conversion if they have decades for that money to grow tax-free. 


For example, $100,000 converted to a Roth at age 35 could potentially grow to over $1 million by retirement age — all of which could be withdrawn tax-free. That same conversion done at age 60 might only have time to grow to $140,000-$150,000 before withdrawals begin.


4. You Want to Leave a Tax-Free Legacy

Roth IRAs are powerful estate planning tools. Your spouse can treat an inherited Roth IRA as their own, allowing the assets to continue growing tax-free without requiring distributions during their lifetime, creating the potential for decades of additional tax-free growth.


Kids or grandkids who inherit a Roth IRA will also enjoy a tax-free inheritance, at least for a time. In contrast, inheriting a traditional IRA means your beneficiaries would pay taxes on every dollar they withdraw — potentially during their peak earning years when they’re in a higher tax bracket.


When Roth Conversions Don’t Make Sense


Of course, just because you can convert doesn’t mean you should. Here are a few situations when a Roth conversion strategy might not work in your favor:


1. You’re Currently in a High Tax Bracket

If you’re currently in your peak earning years and already paying taxes in the 35% or 37% federal tax brackets, converting could mean handing over a substantial portion of your retirement savings to the IRS.


For example, a $100,000 conversion for someone in the 35% federal tax bracket could trigger an additional tax bill of $35,000 or more. If you expect to be in a lower bracket during retirement — say 22% or 24% — waiting to pay taxes then might be more advantageous.


2. You Don’t Have Cash to Pay the Taxes

The most efficient Roth conversion strategy requires having cash outside your retirement accounts to pay the resulting tax bill. Here’s why this matters:


If you have to withdraw extra money from your traditional IRA to cover the taxes on the conversion, you’re reducing your future growth potential. For instance, if you want to convert $50,000 and are in the 24% tax bracket, you may need an additional $12,000 for taxes. If you take that $12,000 from your IRA too, you’d pay taxes on that withdrawal as well, creating a compounding tax problem. 


Even worse, if you’re under age 59½, you could face a 10% early withdrawal penalty on any funds used to pay the taxes, further reducing the effectiveness of your conversion. 


3. You’ll Need the Money Soon

In general, Roth IRAs have a five-year rule that states you must wait five years from the beginning of the tax year of your first contribution to make a withdrawal of the earnings. (You can withdraw contributions, not earnings, tax-free and penalty-free at any time.)


For Roth conversions, however, a new five-year rule starts separately for each conversion. While there are exemptions to this penalty, such as disability and turning age 59½, it’s worth considering if you plan to use the converted funds in the near future.         


Enter: The Roth Conversion Ladder


One strategy we often recommend to clients who want to implement a Roth conversion is the Roth conversion ladder. This approach helps work around the five-year rule while building a tax-efficient income stream, especially for those planning an early retirement. 


Here’s how it works:


Year 1: You convert a portion of your traditional IRA to a Roth (let’s say $30,000).

Year 2: You convert another $30,000.

Year 3: You convert another $30,000.

Year 4: You convert another $30,000.

Year 5: You guessed it — you convert another $30,000.

Year 6: Now the Year 1 conversion is available for withdrawal without penalties.

Each following year: A new “rung” of the ladder becomes accessible while you continue adding new conversions at the top.


Over time, you build a steady stream of tax-free income in retirement that you can predictably access. This strategy is particularly valuable for early retirees who need income before the traditional retirement age or for anyone looking to minimize RMDs down the road.


For example, a couple retiring at 55 might build a conversion ladder to provide $30,000 of annual tax-free income starting at age 60, giving them a bridge until they begin taking Social Security benefits at age 67. Meanwhile, they can use other savings for the first five years of retirement while the initial conversions “season.”


The ladder approach also allows you greater flexibility to manage your tax bracket each year by controlling exactly how much you convert, rather than converting a large sum all at once and potentially pushing yourself into a higher tax bracket.


Making Your Roth Conversion Decision


As you’ve seen, Roth conversions are far from a one-size-fits-all strategy. The right approach depends on your unique financial situation, current and future tax bracket, retirement timeline, and long-term goals.


When considering a Roth conversion, remember that it’s not just about the math. Many of our clients initially hesitate at the thought of writing a big check to the IRS today, even when they know the long-term benefits. That emotional response is completely normal.


This is where thoughtful financial planning comes in. At Five Pine Wealth Management, we help you look beyond the immediate tax bill to see how today’s decisions impact your retirement income, Social Security strategy, and even your legacy plans. Sometimes, what feels uncomfortable at the moment creates the greatest long-term benefit for you and your family.


So, should you do a Roth conversion? The answer depends on:



  • Your current and projected future tax brackets
  • Whether you’re above income limits for direct Roth contributions
  • Your retirement timeline
  • Whether you have cash available to pay the conversion taxes
  • Your estate and legacy goals
  • Your comfort with paying taxes now versus later


A Roth conversion can be either a powerful wealth-building tool or an unnecessary tax expense. The difference comes down to proper planning and timing.


The Next Step


If you’re wondering whether a Roth conversion makes sense for your situation, let’s talk. Our fiduciary advisors will help you evaluate your options and develop a conversion strategy that aligns with your comprehensive financial plan.


We’ll walk through different scenarios, look at the numbers together, and help you feel confident in your decision  — whether that means converting, waiting, or taking a gradual approach with a conversion ladder.


Ready to explore whether a Roth conversion is right for you? Give us a call at 877.333.1015 or send us an email at info@fivepinewealth.com to schedule a conversation.

Join Our Newsletter


Plan smarter with our monthly financial tips + insights

What’s the Best Way to Leave Money to Your Children?

June 17, 2026
Key Takeaways Teaching financial literacy and family values is often just as important as passing down money. A thoughtful estate plan can help reduce family conflict and support future generations. Starting your estate planning early, before you feel like you need to, puts you in the best position to protect your family and your legacy. A trust can help you control when and how your children receive inherited assets. At some point, the question stops being "do I have enough?" and becomes "what do I actually do with all of this?" For a lot of families, that includes figuring out how to pass wealth to their kids without creating a mess. Leaving money to your children doesn't have to be an all-or-nothing decision. A thoughtful estate plan can help you transfer wealth in a way that reflects your values while giving your children the support they need at different stages of life. The most effective plans usually combine smart legal structures with ongoing conversations about money, responsibility, and family goals. Will vs. Trust One of the first decisions many families face is whether to use a will or a trust. A will outlines how you want your assets distributed and who will oversee the process. It’s an important estate planning document and serves as the foundation of many estate plans. A trust, however, can offer additional control and flexibility. Assets held in a trust can often pass to beneficiaries more efficiently and allow you to establish specific instructions for how and when assets are distributed. Depending on your goals, a trust may also help provide privacy and additional protection for heirs. For example, rather than leaving a child a large lump sum at age 25, a trust could allow distributions over time or for specific purposes such as education, housing, healthcare, or starting a business. That doesn't mean a trust is automatically the right solution for everyone. Some families have relatively simple estates and may find that a will adequately accomplishes their objectives. If you have younger children or adult children who aren't quite ready to manage a large inheritance on their own, a trust gives you options that a will simply does not. The important thing to remember is that estate planning isn't just a decision about who gets what. It's an opportunity to decide how wealth is passed on and what guidance, if any, accompanies it. Structured Inheritance Strategies Many parents are uncomfortable with the idea of leaving a significant inheritance all at once. That concern is understandable. Most people can think of examples where a sudden influx of money led to poor decisions, strained relationships, or unrealistic expectations. Structured inheritance strategies can help address those concerns while still providing meaningful support. Some common approaches include: Distributing a portion of assets at specific ages, such as 30, 35, and 40. Allowing distributions for education, healthcare, or home purchases. Creating incentives tied to employment, entrepreneurship, or other personal goals. Establishing trusts that provide ongoing oversight from a trustee. Funding educational accounts for grandchildren as part of a multigenerational plan. These approaches allow wealth to be transferred gradually rather than all at once. There is no universally correct formula because every family is different. A child who is financially responsible at age 25 may require very little structure, while another may benefit from additional oversight for many years. Whatever structure you choose, the goal should be the same: to give your children a foundation, not a crutch. Legacy Planning is About More Than Money When people hear the phrase "legacy planning," they often think about legal documents, account balances, and beneficiary designations. Those items matter, but many families discover that the most valuable inheritance isn't financial. Your values, family traditions, work ethic, charitable priorities, and approach to money often have a greater impact on future generations than the dollars themselves. Consider this question: If your children received your wealth tomorrow, would they also understand the principles that helped create it? Many parents spend years teaching their children how to drive, prepare for college , choose a career, and raise a family. Yet conversations about investing, taxes, budgeting, and responsible wealth management are sometimes delayed until much later. Financial education doesn't need to be complicated. It can begin with simple discussions about spending decisions, saving goals, charitable giving , investing, and how money supports the life you want to live. The earlier those conversations begin, the more prepared future heirs often become. Preparing Heirs for Financial Responsibility Heirs are often better prepared when they understand both the opportunities and responsibilities that come with inherited assets. That preparation can happen gradually over time. Parents might involve adult children in family financial discussions, explain the purpose of trusts and estate plans, or share the reasoning behind major financial decisions. Some families even hold annual meetings where children learn about family values, charitable priorities, business interests, or long-term planning goals. These conversations are not about revealing every financial detail. Rather, they help create context and understanding. When children know why wealth exists and what it represents, they are often better equipped to manage it responsibly. For families with substantial assets, introducing adult children to trusted advisors can also be beneficial. Building relationships before an inheritance occurs can make future transitions smoother and reduce confusion during an already emotional time. Generational Wealth Transfer A successful generational wealth transfer involves much more than moving assets from one generation to the next. It requires balancing financial support with personal responsibility. Some parents worry about giving too much, while others worry about not giving enough. Most fall somewhere in the middle. The answer is rarely found in a single document or account balance. Instead, successful wealth transfers often combine: A well-designed estate plan. Appropriate use of wills and trusts. Clear communication among family members. Financial education for future heirs. A shared understanding of family values and priorities. When those elements work together, wealth has a much better chance of creating opportunity rather than confusion. Start the Conversation Now Many parents want their children to enjoy greater financial security than they had growing up. That's a worthy goal, but providing an inheritance is only part of the equation. The structure of the transfer matters, but so do the conversations surrounding it and the values passed along. A thoughtful plan can protect family relationships, reduce uncertainty, and increase the likelihood that your wealth will continue supporting future generations in meaningful ways. If you'd like help evaluating your estate plan, discussing inheritance strategies, or creating a comprehensive legacy plan, the team at Five Pine Wealth Management would be happy to talk it through with you. Call (877) 333-1015 or email us today to schedule a conversation.  Frequently Asked Questions (FAQs) Q: At what age should I leave money to my children? A: There is no universal answer, but many families use a staged distribution approach, releasing funds at specific ages or milestones, such as completing college or reaching age 30, to give heirs time to build financial maturity before managing larger sums. Q: How can I prepare my children to manage an inheritance responsibly? A: Start having age-appropriate conversations about money, investing, saving, and family values. Introducing adult children to your financial advisors before an inheritance occurs is also worth considering; it makes the transition smoother and gives everyone more time to prepare. Q: Do all families need a trust? A: Not necessarily. Some families can accomplish their goals with a will and beneficiary designations alone. A trust is worth considering if you want more control over how assets are distributed, if your estate is more complex, or if your heirs would benefit from some structure around when and how they receive inherited funds.

When Saving Money Starts Getting in the Way of Living

May 21, 2026
Key Takeaways Saving money is important, but constantly postponing meaningful experiences can leave you financially secure and personally unfulfilled. Fear, habit, and identity often play a bigger role in spending decisions than numbers do. A healthy financial plan should support both your future security and your ability to enjoy life along the way. Imagine you’ve saved diligently for decades. You have a healthy income, growing retirement accounts, manageable debt, and investment balances that continue climbing year after year. Yet, somewhere in the back of your mind, a voice keeps saying, “Not enough.” So you hold off on the vacation or skip the kitchen renovation. You tell yourself you will spend more freely later, once things feel more certain. You keep asking yourself the same question, “Can we really afford this?” Sometimes the answer is yes by every objective financial measure, but emotionally, it still feels uncomfortable. For years, personal finance advice has focused heavily on the dangers of overspending. Save more. Spend less. Delay gratification. Avoid lifestyle creep. That advice absolutely matters. Many people would benefit from stronger saving habits. But there is another side of the equation that does not get discussed enough. Some people become so good at saving that they forget what the money was for in the first place. Am I Saving Too Much?  This question sounds almost absurd, and many people feel uncomfortable asking it. In our culture, saving is viewed as responsible and disciplined. Spending often gets framed as careless or indulgent. So when someone continues accumulating wealth year after year, nobody really raises concerns. But over-saving can create its own problems. We have worked with people who consistently save large percentages of their income while postponing almost everything meaningful to them. They delay vacations. Put hobbies on hold. Continue working in stressful jobs long after they financially need to. They keep waiting for some future point where they will finally feel safe enough to enjoy what they built. The challenge is that “enough” can become a moving target. As portfolios grow, lifestyles usually grow too. Concerns about inflation, healthcare costs, market volatility, taxes, and longevity all start competing for attention. Even financially successful people can develop a persistent fear that one wrong decision could jeopardize everything. That fear is often emotional rather than mathematical. In many cases, the numbers support far more flexibility than the person believes. The Psychology of Saving Money Saving behavior is deeply tied to emotion, identity, and the stories we tell ourselves about security. Understanding why you save the way you do is the first step toward making more intentional choices. Fear of running out is one of the most powerful drivers. Even people with substantial assets can feel that their wealth is fragile, particularly if they grew up without financial stability or lived through a major market downturn. The brain tends to overweigh dramatic losses compared to equivalent gains, which means the emotional pain of imagining a depleted account is often disproportionate to the actual probability of it happening. Habit reinforcement plays a significant role as well. If you spent 30 years in accumulation mode, consistently saving and reinvesting and growing, your financial behaviors became deeply ingrained. Transitioning from saving to spending, even intentionally, and when the numbers support it, can feel wrong at a gut level. The habits that built your wealth can work against you when the time comes to use it. Societal pressure adds another layer. High-earning professionals are often surrounded by messages that equate financial discipline with virtue. Spending on yourself can feel indulgent or even irresponsible, even when it’s neither. There is a difference between careless spending and deliberate investment in your own well-being, but the cultural script often blurs that line. For business owners and dual-income households, there is also the identity piece. When so much of your sense of self is tied to building, growing, and accumulating, shifting toward enjoyment requires a genuine psychological reorientation, not just a new budget line. Values-Based Spending Over-saving isn't fixed by spending more randomly. What actually helps is spending with intention — putting money toward things that genuinely matter to you. This is what we mean by values-based spending : aligning how money flows with what you care about. The exercise starts with a conversation about what you want your life to look like. Not the life you think you should want, and not the life your parents had or your colleagues' project, but the experiences, relationships, contributions, and comforts that would make your days feel meaningful and full. From there, a good financial plan becomes a permission structure. When your advisor can show you, concretely, that your goals are funded and your risks are managed, spending stops feeling like a threat to your security. It starts feeling like money doing what money is supposed to do. Values-based spending also helps you stop spending on things that don’t matter to you. Many high earners discover that their default expenditures have drifted away from their priorities over time. Redirecting those dollars toward what genuinely matters often feels better than a raw increase in spending. Signs You May Be Under-Living Financially A few patterns tend to show up repeatedly among chronic oversavers: You feel guilty spending money even after careful planning. Your savings goals continue increasing without a clear reason. You postpone experiences you deeply want because you “might” need the money someday. You struggle to define what financial freedom would look like for you. Your net worth keeps growing, but your day-to-day life feels largely unchanged. You continue working at a pace that negatively impacts your health or relationships, despite already being financially secure. None of these automatically means you are saving too much. But they are often signals worth examining more closely. Practical Steps to Align Your Money With Your Life Making the shift from over-saving to purposeful living does not require a dramatic overhaul. It starts with a few honest conversations and a willingness to examine some long-held assumptions. Start by revisiting your retirement projections with a financial advisor. Ask specifically what your models say about your ability to spend, not just your ability to accumulate. Many clients are surprised to find that their plan supports significantly more lifestyle spending than they had assumed. Build a "permission budget" for discretionary spending. This is not a ceiling on enjoyment but a deliberate allocation toward experiences and priorities you have identified as meaningful. Giving yourself explicit permission to spend in certain areas, backed by a sound financial plan, reduces the guilt that often accompanies even well-deserved expenditures. Consider what you are waiting for. If the answer is a number that keeps moving, or a level of certainty that financial markets will never provide, it’s worth exploring whether the hesitation is financial or psychological. A good advisor can help you separate the two. A Healthy Financial Plan Should Support Your Life A strong financial plan should create confidence, not permanent deprivation. Saving diligently is important, but there is also value in recognizing when enough may already be enough. The goal is for your spending to reflect your values, your priorities, and where you are in life right now. Because eventually, there has to be a point where the money begins serving you instead of the other way around. If you’ve been wondering whether your saving habits still align with the life you want to live, we’d love to help you think through it. At Five Pine Wealth Management , we help clients build financial plans that support both long-term security and meaningful living today. Call us at 877.333.1015 or email us at info@fivepinewealth.com to start the conversation. Frequently Asked Questions (FAQs) Q: Why do I feel anxious spending money even when I can afford it? A: Spending anxiety is often tied to the psychology of saving money. Past financial stress, market downturns, family experiences, and years of disciplined saving can condition people to associate spending with risk, even when their financial plan supports it. Q: Can over-saving negatively affect your quality of life? A: Yes. Constantly delaying travel, hobbies, family experiences, or personal goals in pursuit of “more” can lead to burnout, stress, and missed opportunities. Financial security matters, but so does enjoying the life your money was meant to support.