Creating an Early Retirement Strategy: Guiding Clients Through the Financial and Emotional Transition

Clients in St. Louis often find that this local connection creates a true partnership. A St. Louis financial advisor like Tim Schulze builds trust by listening, planning, and following through over time.

As wealth grows, finances get more complex. Investments, taxes, estate planning, and insurance often require more than one advisor to manage well.

This article provides an educational overview of how life insurance may be treated for tax purposes under current U.S. tax law. It does not provide tax, legal, or financial advice. Outcomes vary and require individualized review with qualified professionals.

The years just before retirement are typically your last chance to "supercharge" your 401(k). A proactive plan designed to help maximize 401(k) before retirement can make a big difference between a good retirement and a great one.

Today’s beneficiary planning doesn’t end with naming your spouse and children. Tax laws and IRS distribution rules have changed. Modern planning considers trusts, structured beneficiary hierarchies, and tax-aware strategies.

The right partnership provides more than portfolio management. It provides clarity, reduces stress, and gives you the confidence to make big life decisions. When you understand how to choose a financial advisor based on partnership, not just performance, you build the foundation for true, lasting security.

Healthcare is often one of the biggest and most persistent expenses in retirement. Even if you enter retirement healthy, costs can add up fast from insurance premiums, out-of-pocket medical bills, prescriptions and potential long-term care needs. Many retirees underestimate these expenses, especially before they are eligible for Medicare. This can put a strain on retirement savings if there is no plan in place. A thoughtful approach to healthcare planning can make a big difference in keeping you financially stable and at peace. By knowing where costs might arise and how to pay for them, you can plan for the future with confidence. In this article, we’ll look at all the healthcare costs a retiree can expect before, and after, Medicare. Keep reading to learn how to plan adequately for your retirement health expenses. Why Healthcare Is Often a Top Retirement Expense Healthcare is often a top retirement expense. According to Fidelity’s projections , an individual retiring at 65 in 2025 may need an estimated $172,500, up 5% from 2023, to cover medical expenses in retirement. This includes premiums, deductibles and out-of-pocket costs but does not include long-term care, which is often an additional and big expense. These costs can be higher for those retiring before Medicare eligibility. Without planning, early retirees could face higher premiums for private insurance or marketplace plans, especially if they have preexisting conditions or need more comprehensive coverage.  Remember medical inflation outpaces general inflation so healthcare costs may continue to rise faster than most other expenses. What Retirees Will Pay Before Medicare One of the biggest gaps in retirement healthcare planning is the period before Medicare kicks in at age 65. Retirees who leave the workforce earlier need to get their other coverage during these years. Options may include continuing employer-sponsored coverage through COBRA, buying an individual plan on the health insurance marketplace or exploring retirement health insurance options from a former employer. For couples that don’t retire at the same time, another potential solution is coverage under the working spouse’s employer-sponsored health plan. This can often provide more affordable and comprehensive benefits compared to individual plans. Each of these options has different costs and coverage details, so careful evaluation is key. Early retirees should factor these expenses into their pre-Medicare planning well in advance. This means knowing how premiums will fit into their overall retirement budget and how to balance them with other living expenses. Some retirees bridge the gap with part-time work and employer benefits while others may use savings or income-producing investments to help cover these interim costs. The key is to plan ahead so healthcare doesn’t become a financial burden during these years. Long-Term Care: Insurance or Self-Fund? Long-term care is often seen as the wild card of retirement healthcare. It’s help with daily activities, home health aides, assisted living or nursing home care. These costs aren’t covered by standard Medicare plans , except in limited circumstances, so retirees must either buy separate coverage or self-fund. Long-term care insurance can help offset some of these costs but comes with premiums that may increase over time. Policies vary in what they cover so be sure to review the details before committing. If you prefer to self-fund it’s essential to set aside assets specifically for future care needs. This may mean building a dedicated savings or investment account so funds are available when needed. A financial advisor can help determine which approach is right for your health outlook, financial resources and family support network. The choice is personal but having a plan is better than leaving it to chance. How to Use HSAs, Annuities and Income Buckets to Help Bridge the Gap For retirees looking to cover healthcare costs without depleting savings several financial tools can help. Here are just a few examples. A Health Savings Account (HSA) is one of the most tax-efficient ways to prepare for medical expenses. Contributions to an HSA are tax-deductible and withdrawals for qualified medical expenses are tax-free. You can’t contribute to an HSA once you’re on Medicare but the funds already in the account are available for healthcare expenses in retirement. Using an HSA strategically can create a dedicated pool of funds for medical costs. Annuities can also be a useful tool providing a steady stream of income that can be allocated towards healthcare. Not all retirees will need or want an annuity but it can be an effective way to create predictable income to help offset ongoing costs like insurance premiums. Another approach is to structure retirement assets into income buckets. This means dividing investments into different time segments with one bucket for short-to mid term needs like healthcare. By having a specific allocation for medical expenses, retirees can reduce the risk of having to sell long-term investments at an inopportune time to cover unexpected costs. These strategies require coordination but can provide a safety net. A knowledgeable advisor at Pioneer Wealth Management can help determine which options are right for your retirement plan. Final Checklist: Questions to Ask Your Advisor Retirement healthcare costs require open discussion and planning. Ask your advisor: How do I estimate my annual healthcare costs in retirement? How do I plan for the years before Medicare? What options are available to bridge the gap until I turn 65? Should I get long-term care insurance or self-fund? How might an HSA, annuities or investments help with healthcare expenses? What’s the most tax-efficient way to pay for medical costs in retirement? How do we adjust my income plan if healthcare costs go up unexpectedly? Once you discuss these questions, you’ll be able to create the healthcare strategy that aligns with your overall retirement strategy. Conclusion Healthcare costs can be a big deal in retirement and planning for them is key. From the years before Medicare to potential long-term care needs, retirees have a lot of potential expenses to plan for. By understanding the challenges and considering tools like HSAs, insurance, annuities and structured income strategies, retirees can create a safety net to help protect their lifestyle. Work with a trusted advisor at Pioneer Wealth Management to get clarity and confidence on these decisions. Talk to us today to begin creating a solid healthcare strategy for retirement. Investment Advisory Services offered through CreativeOne Wealth, LLC, a registered investment adviser. CreativeOne Wealth and Pioneer Wealth Management are not affiliated companies. Licensed Insurance Professional. We are not affiliated with or endorsed by any government agency, and do not provide tax or legal advice.Investing involves risk, including possible loss of principal. Insurance guarantees are backed by the financial strength of the issuing company. This material is for informational purposes only. Investment advisory services are provided in accordance with a fiduciary duty of care and loyalty that includes putting your interests first and disclosing conflicts. Insurance services have a best interest standard which requires recommendations to be in your best interest. Advisors may receive commission for the sale of insurance and annuity products.

Healthcare is often one of the biggest and most persistent expenses in retirement. Even if you enter retirement healthy, costs can add up fast from insurance premiums, out-of-pocket medical bills, prescriptions and potential long-term care needs. Many retirees underestimate these expenses, especially before they are eligible for Medicare. This can put a strain on retirement savings if there is no plan in place. A thoughtful approach to healthcare planning can make a big difference in keeping you financially stable and at peace. By knowing where costs might arise and how to pay for them, you can plan for the future with confidence. In this article, we’ll look at all the healthcare costs a retiree can expect before, and after, Medicare. Keep reading to learn how to plan adequately for your retirement health expenses. Why Healthcare Is Often a Top Retirement Expense Healthcare is often a top retirement expense. According to Fidelity’s projections , an individual retiring at 65 in 2025 may need an estimated $172,500, up 5% from 2023, to cover medical expenses in retirement. This includes premiums, deductibles and out-of-pocket costs but does not include long-term care, which is often an additional and big expense. These costs can be higher for those retiring before Medicare eligibility. Without planning, early retirees could face higher premiums for private insurance or marketplace plans, especially if they have preexisting conditions or need more comprehensive coverage.  Remember medical inflation outpaces general inflation so healthcare costs may continue to rise faster than most other expenses. What Retirees Will Pay Before Medicare One of the biggest gaps in retirement healthcare planning is the period before Medicare kicks in at age 65. Retirees who leave the workforce earlier need to get their other coverage during these years. Options may include continuing employer-sponsored coverage through COBRA, buying an individual plan on the health insurance marketplace or exploring retirement health insurance options from a former employer. For couples that don’t retire at the same time, another potential solution is coverage under the working spouse’s employer-sponsored health plan. This can often provide more affordable and comprehensive benefits compared to individual plans. Each of these options has different costs and coverage details, so careful evaluation is key. Early retirees should factor these expenses into their pre-Medicare planning well in advance. This means knowing how premiums will fit into their overall retirement budget and how to balance them with other living expenses. Some retirees bridge the gap with part-time work and employer benefits while others may use savings or income-producing investments to help cover these interim costs. The key is to plan ahead so healthcare doesn’t become a financial burden during these years. Long-Term Care: Insurance or Self-Fund? Long-term care is often seen as the wild card of retirement healthcare. It’s help with daily activities, home health aides, assisted living or nursing home care. These costs aren’t covered by standard Medicare plans , except in limited circumstances, so retirees must either buy separate coverage or self-fund. Long-term care insurance can help offset some of these costs but comes with premiums that may increase over time. Policies vary in what they cover so be sure to review the details before committing. If you prefer to self-fund it’s essential to set aside assets specifically for future care needs. This may mean building a dedicated savings or investment account so funds are available when needed. A financial advisor can help determine which approach is right for your health outlook, financial resources and family support network. The choice is personal but having a plan is better than leaving it to chance. How to Use HSAs, Annuities and Income Buckets to Help Bridge the Gap For retirees looking to cover healthcare costs without depleting savings several financial tools can help. Here are just a few examples. A Health Savings Account (HSA) is one of the most tax-efficient ways to prepare for medical expenses. Contributions to an HSA are tax-deductible and withdrawals for qualified medical expenses are tax-free. You can’t contribute to an HSA once you’re on Medicare but the funds already in the account are available for healthcare expenses in retirement. Using an HSA strategically can create a dedicated pool of funds for medical costs. Annuities can also be a useful tool providing a steady stream of income that can be allocated towards healthcare. Not all retirees will need or want an annuity but it can be an effective way to create predictable income to help offset ongoing costs like insurance premiums. Another approach is to structure retirement assets into income buckets. This means dividing investments into different time segments with one bucket for short-to mid term needs like healthcare. By having a specific allocation for medical expenses, retirees can reduce the risk of having to sell long-term investments at an inopportune time to cover unexpected costs. These strategies require coordination but can provide a safety net. A knowledgeable advisor at Pioneer Wealth Management can help determine which options are right for your retirement plan. Final Checklist: Questions to Ask Your Advisor Retirement healthcare costs require open discussion and planning. Ask your advisor: How do I estimate my annual healthcare costs in retirement? How do I plan for the years before Medicare? What options are available to bridge the gap until I turn 65? Should I get long-term care insurance or self-fund? How might an HSA, annuities or investments help with healthcare expenses? What’s the most tax-efficient way to pay for medical costs in retirement? How do we adjust my income plan if healthcare costs go up unexpectedly? Once you discuss these questions, you’ll be able to create the healthcare strategy that aligns with your overall retirement strategy. Conclusion Healthcare costs can be a big deal in retirement and planning for them is key. From the years before Medicare to potential long-term care needs, retirees have a lot of potential expenses to plan for. By understanding the challenges and considering tools like HSAs, insurance, annuities and structured income strategies, retirees can create a safety net to help protect their lifestyle. Work with a trusted advisor at Pioneer Wealth Management to get clarity and confidence on these decisions. Talk to us today to begin creating a solid healthcare strategy for retirement. Investment Advisory Services offered through CreativeOne Wealth, LLC, a registered investment adviser. CreativeOne Wealth and Pioneer Wealth Management are not affiliated companies. Licensed Insurance Professional. We are not affiliated with or endorsed by any government agency, and do not provide tax or legal advice.Investing involves risk, including possible loss of principal. Insurance guarantees are backed by the financial strength of the issuing company. This material is for informational purposes only. Investment advisory services are provided in accordance with a fiduciary duty of care and loyalty that includes putting your interests first and disclosing conflicts. Insurance services have a best interest standard which requires recommendations to be in your best interest. Advisors may receive commission for the sale of insurance and annuity products.

If you have changed jobs a few times, you are not alone. Most people end up with several 401(k)s scattered across old employers, each one quietly sitting in the background. It might not seem like a big deal, but over time, those forgotten accounts can make your retirement picture harder to understand. Every new job typically means a new retirement plan. When you move on, your old account often stays behind, still invested but no longer managed with your overall goals in mind. That setup can leave your money working in different directions, and the longer it goes, the harder it becomes to keep track of what you really own. That is why consolidating all your old 401(k)s into a single, professionally managed IRA is often the best move you can make. It helps you organize your savings, reduce fees, and create a unified strategy designed around your future. And with a 401(k) rollover advisor like Tim from Pioneer Wealth Management, the process is simple, secure, and completely tailored to your needs. Why So Many People Have Unmanaged 401(k)s It is completely normal to have more than one 401(k) from previous jobs. You start one plan, switch jobs, start another, and before long you have several accounts scattered across different providers. Many people delay rolling them over because it feels confusing or time-consuming. Others are worried about triggering taxes or making a mistake. Some just assume that as long as the accounts are growing, everything is fine. But those “out of sight, out of mind” accounts can lead to missed opportunities. Without active oversight, your investments may overlap, sit in outdated funds, or carry higher fees than you realize. And because you are not looking at them often, you might lose track of changes or forget to update beneficiaries. The result is a messy retirement picture that is harder to manage and less effective over time. The Hidden Costs of Multiple Retirement Accounts Leaving old 401(k)s unattended can quietly eat away at your growth. Each account has its own administrative fees, fund expenses, and possibly overlapping investments. When these costs are spread across multiple plans, you end up paying more without gaining any real benefit. Scattered accounts also make it difficult to measure performance. You might have some plans doing well while others lag behind, but without a consolidated view, it is nearly impossible to tell how your overall portfolio is performing. There is also the risk of neglect. Outdated addresses or lost login details can make it harder to access your money when you need it. And if you forget to update beneficiaries after major life changes, your retirement assets might not go where you intend. Consolidating into a single, managed IRA eliminates these issues. You can see your entire portfolio in one place, track your progress clearly, and make decisions based on the full picture, not just pieces of it. Why Rolling Old 401(k)s Into an IRA Is Often the Best Move When it comes to dealing with old 401(k)s, you generally have three choices: Leave them where they are Roll them into your current employer’s plan Move them into an IRA Leaving them in your old plans might seem easiest, but that means continuing to juggle multiple accounts, each with its own fees and investment lineup. 401(k) rollover could simplify things slightly, but many workplace plans limit your investment options or charge higher fees. By contrast, rolling your old 401(k)s into a professionally managed IRA gives you more flexibility, more control, and more opportunity to grow your money efficiently. With an IRA, you are not bound by your employer’s fund list. You can choose from a much broader selection of investments and design a portfolio that fits your specific goals and comfort with risk. A managed IRA through Pioneer Wealth Management takes that one step further. Instead of juggling multiple retirement accounts on your own, you get expert guidance, customized investment management, and ongoing monitoring to keep your plan on track. How Pioneer Wealth Management Simplifies the Process Many people hesitate to consolidate because they worry it will be complicated. But with the right guidance, it can be remarkably smooth. T im and the team at Pioneer Wealth Management specialize in helping clients bring all their old 401(k)s together into one clearly managed IRA. Here is what you can expect when you work with them: Step-by-step rollover support: The team handles every detail, from contacting providers to submitting forms. You never have to worry about making a wrong move or triggering unnecessary taxes. Transparent analysis of fees and investments: They compare your current plans to identify hidden costs and underperforming funds. Personalized investment strategy: Your new IRA is built specifically for your timeline, goals, and tax situation, not a one-size-fits-all approach. Continuous monitoring: Once your IRA is in place, the team continues to oversee your investments, rebalancing and adjusting as needed to keep everything aligned with your goals. With Pioneer Wealth Management, your money is no longer scattered or forgotten. It is organized, watched over, and working toward your future in a clear and coordinated way. How to Start Consolidating Your Accounts If you are ready to take control of your retirement savings, here is how to begin: Gather your information. List each old 401(k) you have, where it is held, and your most recent statement. Meet with Tim and the Pioneer team . They will review your current accounts, identify hidden fees, and pinpoint overlapping investments. Decide on your consolidation plan. Together, you will determine the best structure for your managed IRA. Let the professionals handle the transfer. Pioneer Wealth Management coordinates the rollovers directly with each provider to ensure everything moves smoothly and tax-free. Stay engaged with your plan. Once everything is in one place, you will receive ongoing updates, reviews, and recommendations to keep your portfolio performing at its best. With this hands-on support, you can move from scattered and uncertain to clear, confident, and organized in just a few simple steps. When It Might Make Sense to Keep a 401(k) While consolidating is the best choice for most people, there are rare situations where keeping a specific 401(k) could be beneficial. Some plans offer unique institutional funds or special withdrawal provisions that IRAs do not. That is why working with a fiduciary like Tim is so valuable. He reviews each plan individually to determine whether keeping it separate actually adds value or if rolling it over would be the smarter move. Why a Managed IRA Brings Real Peace of Mind Having one professionally managed IRA instead of several scattered accounts brings clarity, convenience, and confidence. You will know exactly where your money is, how it is performing, and what steps are being taken to keep it growing. At Pioneer Wealth Management, the goal is simple: to make your retirement planning easier while helping you get the most out of what you have saved. Tim and his team act as fiduciaries, meaning they always put your interests first. Their focus is on helping you make informed choices that strengthen your financial future. The Bottom Line If you have multiple 401(k)s from past employers, now is the time to take action. Consolidating them into a single, professionally managed IRA can help you simplify your finances, reduce costs, and make your retirement strategy more efficient. Pioneer Wealth Management has the expertise and tools to make that happen smoothly and safely. You will gain a clearer view of your entire portfolio and the confidence that comes from knowing your savings are being managed by professionals who truly have your back. Reach out to Tim and the team at Pioneer Wealth Management today to start consolidating your old 401(k)s into a unified, professionally managed IRA. It is one of the easiest and most rewarding financial decisions you can make for your future.