4-Step Action Plan to Retire with Confidence

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Jordan Flowers
·
September 10, 2026

The final years before retirement can be some of the most important years in your financial plan. You are close enough to retirement that decisions about taxes, savings, healthcare, and future withdrawals can have a meaningful impact, but you may still have time to make adjustments. Think of it as the retirement red zone. Here are four areas worth reviewing.

1 – Maximize Tax-Advantaged Retirement Accounts

If you are still working, the years immediately before retirement may provide an opportunity to increase retirement savings. For 2026, the basic employee contribution limit for most 401(k), 403(b), governmental 457 plans, and the federal Thrift Savings Plan is $24,500. The general catch-up contribution for eligible participants age 50 and older is $8,000, while workers ages 60 through 63 may qualify for a higher $11,250 catch-up contribution (IRS). Those additional contributions can be particularly valuable late in your career. but deciding where to contribute is also important. Traditional and Roth accounts have different tax treatment, so the goal is not simply maximizing one account, it is creating a mix that fits your current and future tax situation.

2 – Review Your IRA and Roth Strategy

The 2026 IRA contribution limit is $7,500, with an additional $1,100 catch-up contribution for individuals age 50 or older. Eligibility for deductible traditional IRA contributions and direct Roth IRA contributions can depend on income and participation in workplace retirement plans (IRS). Roth accounts can be particularly useful for tax diversification because qualified withdrawals can be tax-free. A Roth conversion may also be appropriate in certain situations, but converting previously untaxed retirement assets generally creates federal taxable income in the year of conversion (IRS). That is why Roth planning should be coordinated with your tax bracket, Medicare considerations, other income, and long-term financial plan rather than treated as an automatic decision.

3 – Don’t Overlook the HSA

For eligible individuals, a Health Savings Account can be one of the most tax-efficient accounts available. Under IRS rules, eligible HSA contributions may be deductible or excluded from income, earnings are not included in taxable income while held in the account, and distributions used for qualified medical expenses are generally tax-free (IRS). That combination can make an HSA useful not only for today’s healthcare expenses, but potentially for healthcare costs later in retirement. The key here is understanding what qualifies as a medical expense. For example, ordinary gym memberships for general wellness generally do not qualify simply because they promote good health (IRS).

4 – Understand Required Minimum Distributions Before They Begin

One of the most common assumptions about retirement is that taxes will automatically go down, but that is not always the case. Traditional retirement accounts can eventually create required minimum distributions, or RMDs. Under current law, the applicable RMD age is 73 for many retirees and rises to 75 for individuals born in 1960 or later. Roth IRAs and designated Roth employer-plan accounts generally do not require RMDs while the original owner is alive (IRS). Large future RMDs can affect taxable income and interact with other areas of the retirement plan. That is why tax planning can be especially valuable before required distributions begin.

Bonus Step: Coordinate the Pieces

A 401(k) decision affects taxes, Roth conversions affects taxes, and taxes can affect Medicare costs. Healthcare planning affects how much income your portfolio needs to generate, and all of those decisions ultimately affect your legacy and long-term financial security. Retirement planning works best when these pieces are considered together. The goal is not just to grow your assets. It is to create a strategy for turning those assets into the income, flexibility, and lifestyle you want in retirement.

To hear more on this topic, watch the full video here!

Erin: Jordan, so good to see you. This video is for anyone who is nearing retirement. We have a four-step action plan for success. If you are close to retirement, you’re in what’s known as the retirement red zone. Every financial decision you make is crucial, which is why we are laying out four steps to help maximize tax advantages, manage future income, and avoid costly surprises. Step number one: max those tax-advantaged retirement accounts, including those catch-up contributions.

Jordan: Yeah, you said retirement red zone. It just made me think it’s Chicago Bears football season. Okay, I’m excited for this year, I hope. But just like the Bears offense, they’re not only running the ball, they’re not always throwing deep passes. They’re diversifying on where they put the ball.

Likewise, we need to diversify where we are putting the assets. Are we doing it in pre-tax accounts, post-tax accounts, non-qualified accounts? We need to be tax diversified. But really take advantage of those tax-advantaged accounts and 401(k)s and IRAs because that tax-advantaged benefit can far outweigh over time that long-term growth.

Erin: I’m glad you brought that up because step number two is to open and max out your IRA as well. And you’re suggesting to people consider adding all their money to the Roth side or even considering a conversion to make sure they are tax diversified.

Jordan: The question comes to you is, do you think taxes will be higher in the future? I do. Five to ten years—you think that, Erin. Ninety-nine percent of people think that. We have historically low tax rates. So if you think that, we want to probably put more money in tax-free Roth accounts because once it’s tax-free, it’s tax-free forever. And I’d rather pay taxes when they’re on sale, or pay now for the next three years.

That being said, this is where the planning comes into play. For most people, you probably still want to make a traditional contribution inside your 401(k), so then you don’t pay any Illinois tax on that contribution. But then before the end of the year, if your 401(k) allows this, you can then convert that in December to a Roth. So therefore you pay taxes while they’re on sale. You get that growing tax-free in the Roth forever. Oh, and by the way, we pay the state of Illinois 4.95% less in taxes on that money. So it’s a win, win, win. You just have to go a little bit deeper when it comes to planning to execute that strategy.

Erin: Yeah, I love it. You’re always thinking outside the box, Jordan. On that note, though, with tax diversification, leveraging health savings accounts—this is a really, I feel like, often overlooked strategy. They are uniquely triple tax advantaged.

Jordan: Yeah. It’s a tax deduction when you put it in, tax-free when you grow it, tax-free when you take it out for healthcare benefits. And there are so many easy ways to find things you can take out to use for healthcare, whether it be part of Medicare, whether it be different—even gyms you can use HSAs sometimes for—and different health equipment. Definitely will get a use in your lifetime because we all know we need some health benefits, whether it be for Medicare or things that come up in our life. So let’s capitalize on that opportunity and max those out if we can to get more tax-free growth and tax-free use in the future.

Erin: Next, understand required minimum distributions. We’ve talked about this one before in many of our other videos on YouTube. If anybody’s watching us online right now, go check them out. A lot of people assume they’re going to be in a lower tax bracket when they retire, but these required minimum distributions often throw people off and into a higher bracket.

Jordan: Yeah, I just want to go behind the scenes why. So when you reach the age of 73 or 75, if you’re born after 1960, the government just forces you to take money out of those IRAs because they want—they want you to go on vacation and spend time with your family.

Well, not actually true. What they really want is the money, right? It’s been deferred for 20, 30, 40 years. They force you to take that money out and pay taxes on that. And if you don’t plan for that, higher income from those required minimum distributions will put you in higher tax brackets. By the way, that might also put you in higher Medicare IRMAA brackets because it’s a domino effect. And a lot of people can be blindsided.

Now, for a lot of our clients, we try to have a diversified tax plan where, if we can, we minimize or maybe eliminate those. Because if you have money in a Roth IRA, there is no required minimum distribution. We’ve got to make sure we have a plan—not hopefully before you get to 73 or 75—but even if you’re there, we can still do some good planning for you.

Erin: And we do have a bonus step for everyone: consult an advisor. Why is that important?

Jordan: Yeah, because we provide financial leadership and we help coordinate all these different strategies. We actually have a roadmap that we give to our clients. You can see on the screen that tax planning is at the center of everything we do. Most advisors out there, they just focus on asset accumulation and asset growth. And although we take that seriously and want you to get competitive returns, we want to make sure you keep more of what you make.

Because it’s not what you make. It’s what you actually get to keep. And we coordinate that income plan with RMDs, healthcare, your legacy, and make sure you have that one-stop shop to give you that peace-of-mind feeling.

Erin: Yeah, well said. I do not want all of those pieces to be my job in retirement, but that’s just me.

Jordan: We want to do the heavy lifting for our clients.

Erin: Jordan, if somebody would like to sit down with you, if they’re getting close to retirement, if they’re in that red zone like the Bears, what’s the best way to reach you?

Jordan: Yeah, and I’ll just say a brief story. I talked to a client today. She’s like, “I was so intimidated coming and seeing you guys. This is such a nice feel. I feel at home.” Because we take the complex and make it simple. We have that nice environment. The first step would be to schedule that time so we can meet: 847-499-3454.

Erin: Yeah, no, it’s such a well-worth-it step. Well said. Jordan, thank you so much for your time today. Everybody, please stand by for that QR code at the end.

Jordan: Thanks, Erin.

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