Retirement Income Planning: Building a Plan That Can Last 30 Years

RUNTIME: 10:54

Key Takeaways

About the Webinar

Retirement used to be a short chapter. Today, it can be a third of your life. In this webinar, Troy Fore, CFP®, Director of Client Engagement at Aspen Wealth Management, walks through what retirement income planning looks like when the plan needs to hold up for 25, 30, or more years. The session is designed for families nearing retirement or already retired and focuses on four areas that often have the greatest impact on retirement outcomes: income, taxes, portfolio structure, and long-term flexibility. 

The starting point is simple math with big consequences. If one spouse retires at 65 and lives into their nineties, the portfolio isn’t just funding today’s lifestyle. It may need to absorb decades of inflation, multiple market cycles, rising healthcare expenses, and evolving family priorities. A longer timeline magnifies both the opportunities and the risks. 

Retirement Risk Is Bigger Than Market Volatility 

Most people equate retirement risk with the stock market. Markets matter, but several other risks tend to grow in importance over time: longevity risk, inflation quietly eroding purchasing power, taxes becoming more impactful later in retirement, healthcare costs, and emotional decision-making during difficult markets. Troy also breaks down sequence of returns risk, the reason two retirees with similar average returns can end up in dramatically different positions. Withdrawals taken during down markets reduce the assets available to participate in a future recovery, which is why the first several years of retirement carry outsized weight and why thoughtful income planning and proper liquidity matter so much. 

Intentional Retirement Income Planning 

Once the paycheck stops, income may come from several coordinated sources: Social Security, portfolio withdrawals, pensions where available, and other assets. What you want to avoid is pulling money from accounts at random. Troy shares a framework Aspen often uses: assigning different jobs to different dollars. Near-term dollars support spending over the next several years. Intermediate assets focus on stability and income. Longer-term assets stay growth-oriented to help offset inflation. This structure can reduce the need to sell growth assets during down markets, and the peace of mind it provides may help families stay disciplined when volatility inevitably arrives. 

On withdrawal rates, the honest answer is that there’s no universal magic number. The appropriate strategy depends on spending needs, flexibility, taxes, legacy goals, market conditions, and the structure of the household balance sheet. Two families with similar levels of wealth may need very different approaches, which is why retirement income planning works best when it’s personalized rather than formula-driven. 

Taxes: The Account You Withdraw From Matters 

Not all retirement dollars are taxed the same way. Taxable brokerage accounts may offer flexibility and favorable capital gains treatment. Traditional IRAs and 401(k)s generally create ordinary income. Roth accounts can provide tax-free qualified withdrawals. Thoughtful distribution sequencing across those account types can create meaningful tax savings over time. Timing matters too. The years between leaving work and required minimum distributions often bring a temporary reduction in income, opening opportunities for partial Roth conversions, tax bracket management, and Medicare IRMAA planning. Many retirement tax problems, like large RMDs or a surviving spouse facing single-filer brackets, are created years earlier. Proactive tax planning beats reactive tax planning, and the earlier the conversation starts, the more options exist. 

The Portfolio’s Job Changes in Retirement 

During accumulation, the portfolio’s main job is growth. In retirement, it has several jobs at once: generating income, maintaining growth potential, providing stability, creating liquidity, and helping you feel confident enough to stay invested through volatility. Cash plays a misunderstood role here. It won’t maximize long-term returns, but not every dollar needs to. Some dollars need to maximize flexibility, support spending needs during difficult markets, and reduce forced selling. Ultimately, discipline matters far more than prediction, and consistent decision-making matters more than short-term forecasting. 

A successful retirement plan has less to do with finding the perfect investment and more to do with building the right structure, where income strategy, tax strategy, investment management, risk management, and legacy and estate planning all work together. 

If you’re nearing retirement, already retired, or simply wondering whether your current plan could be improved, watch the full webinar above. If you’d like a second set of eyes on your plan, we’d be happy to have a conversation and see whether Aspen may be a good fit. Schedule a free consultation to start the conversation. 

[00:00] Hey everyone, Troy Four here with Aspen Wealth Management.
[00:03] I appreciate y’all taking the time to join me.
[00:05] Today we’re going to talk about retirement planning, but specifically what it looks like to build a plan that can realistically support decades of life beyond your working years.
[00:14] For many people, retirement’s no longer a short chapter.
[00:17] It may last 25, 30, or even more years.
[00:21] And because of that, the planning process has changed quite a bit.
[00:25] What I’d like to do today is walk through some of the biggest planning considerations we see for families nearing retirement or already retired, particularly around income, taxes, portfolio structure, and long term flexibility.
[00:38] The goal here isn’t to overwhelm you with technical detail.
[00:42] It’s to provide a practical framework for thinking about how all these moving pieces fit together over time.
[00:48] So, with that in mind, let’s start with the big picture.
[00:51] Retirement today looks very different than it did.
[00:54] For previous generations.
[00:55] People are generally living longer.
[00:57] Retirement years are often more active and experience driven.
[01:02] Healthcare costs continue to rise, and there are simply more financial decisions to coordinate over time.
[01:08] For many households, pensions are less common than they used to be, which means retirees are increasingly responsible for managing their own assets and creating their own income structure.
[01:17] At the same time, retirement itself has evolved.
[01:21] People want to travel more, spend time with family.
[01:24] Support children or grandchildren, give generously, stay active, and stay engaged.
[01:30] All that’s wonderful.
[01:31] But it also means retirement planning has become more complex than simply accumulating assets and flipping on income.
[01:39] And one of the biggest reasons for all that complexity is simply time.
[01:43] someone retires around age sixty five today, there’s a very real possibility one spouse lives into their nineties.
[01:49] That means retirement itself could last thirty years or more.
[01:53] And when you really stop and think about that, it changes the equation quite a bit.
[01:57] You may spend nearly as much time in retirement as you did building the assets for it.
[02:02] That means your portfolio isn’t just supporting today’s lifestyle.
[02:05] It may need to support decades of inflation.
[02:08] Market cycles, healthcare expenses, and evolving family priorities.
[02:12] And that longer timeline tends to magnify both opportunities and risks.
[02:17] Which leads us into something we talk about often with clients.
[02:20] Retirement risk isn’t just about the stock market.
[02:24] When most people think about retirement risk, they naturally think about market volatility.
[02:29] And of course, markets matter.
[02:31] But in reality, there are several risks that often become just as important over time.
[02:35] Longevity risk, simply living longer than expected.
[02:39] Inflation gradually reducing purchasing power.
[02:42] Taxes becoming more impactful later in retirement, Healthcare costs, and emotional decision making during difficult markets.
[02:52] A strong retirement plan should help prepare for market volatility, but also help investors stay disciplined during periods of uncertainty.
[02:59] Because in many cases, some of the most damaging financial decisions happen emotionally, not mathematically.
[03:06] And one risk in particular becomes especially important during the early years of retirement.
[03:12] This slide illustrates what’s known as sequence of returns risk.
[03:16] Two retirees may earn very similar average returns over time, but if one experiences weaker market returns early in retirement while simultaneously taking withdrawals, the long-term outcome can look dramatically different.
[03:30] That’s because withdrawals during down markets reduce the assets available to recover later.
[03:36] That’s one reason retirement planning is fundamentally different from accumulation planning.
[03:40] Withdrawals change the equation.
[03:43] And it’s also one reason the first several years of retirement tend to matter so much.
[03:47] It doesn’t mean markets need to be predicted perfectly, but it does reinforce the importance of thoughtful income planning, proper liquidity, and maintaining flexibility.
[03:57] Because once the paycheck stops, income planning becomes one of the most central parts of the conversation.
[04:04] One of the biggest transitions in retirement is moving from accumulation to distribution.
[04:10] During working years, income largely comes from employment.
[04:13] In retirement, income may come from several coordinated sources Social Security, portfolio withdrawals, pensions if available, and potentially other assets or income streams.
[04:25] What we want to avoid is simply pulling money randomly from accounts as needed.
[04:29] Instead, retirement income should be designed intentionally.
[04:34] For many higher net worth households, withdrawal strategy also becomes heavily intertwined with taxes, legacy planning, charitable goals, and long-term flexibility.
[04:44] And ideally, the structure evolves over time as circumstances change.
[04:48] One framework we often use when thinking through that structure is assigning different jobs to different dollars.
[04:55] We often think about retirement assets in terms of time horizon.
[04:59] Near-term dollars may support spending needs over the next several years.
[05:04] Intermediate assets may focus more on stability and income generation.
[05:08] Longer-term assets can remain growth-oriented to help offset inflation and support later retirement years.
[05:14] This approach can help reduce the need to sell long-term growth assets during difficult markets.
[05:20] It can also provide psychological comfort.
[05:22] Because clients know shorter term spending needs may already be accounted for.
[05:26] And sometimes that peace of mind may help people stay disciplined when markets inevitably become volatile.
[05:33] Now, naturally, one of the next questions people ask is how much can I safely spend?
[05:39] A lot of retirement conversations eventually come back to withdrawal rates.
[05:43] And while there are certainly helpful frameworks and guidelines, there really isn’t a universal magic number that applies to everyone.
[05:50] The appropriate withdrawal strategy depends on a number of factors spending needs, flexibility, taxes, legacy goals, market conditions, the overall structure of the household balance sheet, too.
[06:03] Two families with similar net worth may require very different strategies depending on their goals and circumstances.
[06:09] It’s why retirement planning tends to work best when it’s personalized rather than formula driven.
[06:15] And one of the biggest variables within that planning process is taxes.
[06:21] Not all retirement dollars are taxed the same way.
[06:23] Taxable brokerage accounts may offer flexibility and potentially more favorable capital gains treatment.
[06:29] Traditional IRAs and 401ks generally create ordinary income when distributions are taken.
[06:35] Roth accounts can provide tax-free qualified withdrawals.
[06:39] So the account you withdraw from can matter just as much as the amount you withdraw.
[06:44] Over time, thoughtful distribution sequencing.
[06:47] among the various accounts can create meaningful tax savings and greater flexibility.
[06:52] And timing can matter quite a bit as well.
[06:55] For many retirees, the years between leaving work and required minimum distributions can create especially valuable planning opportunities.
[07:04] Income is sometimes temporarily lower during this period.
[07:07] That can create opportunities for partial Roth conversions.
[07:11] At lower marginal tax rates before future RMDs potentially increase taxable income later.
[07:16] It may also create opportunities for tax bracket management and Medicare IRMA planning.
[07:22] Often these years are more valuable from a planning standpoint than people initially realize, because many retirement tax problems aren’t created overnight.
[07:32] A lot of tax challenges we see later in retirement are actually created years earlier.
[07:37] Large IRA balances can eventually create sizable RMDs.
[07:41] A surviving spouse may face higher marginal tax brackets filing single.
[07:46] Medicare surcharges can become more significant over time, and concentrated appreciated assets can create flexibility issues.
[07:54] That’s one reason proactive planning tends to be much more effective than reactive planning.
[07:59] The earlier these conversations begin, the more options generally exist.
[08:04] Now shifting away from taxes for a moment, let’s talk about the portfolio itself.
[08:10] During accumulation years, the portfolio’s primary responsibility is often growth.
[08:15] In retirement, the portfolio usually has several jobs simultaneously.
[08:19] Generating income, maintaining growth potential, providing stability, creating liquidity, helping clients feel confident enough to stay disciplined through volatility.
[08:29] That’s a much more nuanced role than simply maximizing return.
[08:33] And in many cases, retirement portfolio construction becomes much more about balance, coordination, Then aggressiveness.
[08:40] And one piece of that balance that often gets misunderstood is cash.
[08:45] Cash generally won’t maximize long-term returns.
[08:48] But in retirement, not every dollar needs to maximize return.
[08:52] Some dollars need to maximize flexibility.
[08:54] Cash reserves can help support spending needs during difficult markets.
[08:59] They can reduce the need for forced selling, and they often provide emotional comfort during periods of volatility.
[09:05] Sometimes having liquidity available helps clients stay disciplined with the rest of the portfolio.
[09:10] And ultimately, discipline tends to matter much more than prediction.
[09:15] We don’t believe successful retirement planning requires perfectly predicting markets.
[09:20] It often requires maintaining discipline through changing environments, rebalancing after strong runs, staying steady during declines, and following process instead of reacting emotionally to headlines.
[09:32] Because over long periods of time, consistent decision making tends to matter far more than short-term forecasting.
[09:39] And ultimately, all this planning is meant to support something bigger than numbers on a statement.
[09:45] For most families, wealth itself isn’t ultimate goal.
[09:49] It’s what wealth allows them to do.
[09:51] Freedom, security, supporting family wisely, giving generously, creating opportunities, having peace of mind.
[10:00] Those are usually the things that matter most.
[10:03] And ideally, a financial plan aligns assets with those broader life priorities.
[10:08] So let me leave you with one final thought.
[10:12] A successful retirement plan usually has less to do with finding the perfect investment and more to do with building the right structure.
[10:19] Income strategy, tax strategy, investment management, risk management, legacy planning.
[10:26] When those pieces are coordinated thoughtfully, retirement often feels much more manageable and much more intentional.
[10:32] If you’re nearing retirement, already retired, or simply wondering whether your current plan could be improved, it’s a good time to revisit it.
[10:41] I appreciate y’all spending time with me today.
[10:44] Hope this was helpful.
[10:45] And we’d be honored to be a resource if we can help in any way.

Webinar Speakers:

Troy Fore, CFP®, Senior Financial Planning Associate

Troy Fore, CFP®

Director of Client Engagement
Troy Fore, CFP®, joined Aspen Wealth Management as a Senior Financial Planning Associate in 2023. An experienced professional with a background in investment, risk management, tax planning, and estate and legacy planning, Troy is dedicated to serving his clients and today he is our Director of Client Engagement.

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