Five Pine Wealth Management

11/03/2026

Where were you in October of 1987?

If you were investing back then, you probably remember Black Monday.

It’s one of several October market drops that gave this month its distinctly spooky Wall Street reputation, sometimes called the “October Effect.” 🎃

We can save the screams for Halloween, though.

The long-term data is much less scary; October hasn’t historically been the market’s worst month. At times, it’s even been the turnaround point for down markets.

Still, we don’t make investment decisions based on the calendar. A good plan, built around your goals and timeline, doesn’t change with the seasons (or their reputations).

Go ahead and enjoy pumpkin everything and handing out candy this fall. And if the headlines start getting too spooky, reach out anytime. We’re happy to talk it through with you.

10/27/2026

“I’ll make sure that if something happens to me, you’ll be okay.”

Many married couples make this promise to each other. They save and plan diligently while keeping all the paperwork up to date.

Still, many of those plans don’t account for what happens when the surviving spouse has to file their taxes alone.

In 2026, $260,000 of taxable income falls into the 24% bracket for joint filers. For a single filer, that same income falls in the 35% bracket.

And for many surviving spouses, income doesn’t drop all that much.

👉 Required minimum distributions continue
👉 The larger of their two Social Security benefits stays in place

Couples can plan for this together, though. The years between retirement and RMDs are often a prime window for Roth conversions under more generous joint tax brackets.

Those conversions can also leave your kids Roth money they can generally withdraw tax-free.

If you want to learn more, this week’s blog post walks through how your tax return changes after a spouse passes and the bridge-year conversion strategy.

What’s one money conversation you think every couple should have before retirement?

If you asked married couples what they want their retirement savings to do, most would agree something like this is a top priority: if anything happens to one of us, the other will be okay, and so will our kids.

10/15/2026

A $25,000 gift for your grandchild’s future could end up funding something you never intended.

Before you decide how to give it, ask yourself:

•What do I want this money to help my grandchild accomplish?
•Do I want to control how it’s used?
•When do I want them to have access to it?

Your answers can help determine which gifting option makes the most sense.

If your goal is to help pay for education, a 529 account could be a good fit. You maintain control of the account, and the money can grow tax-free with tax-free withdrawals for qualified education expenses.

If your grandchild doesn’t need all the money, you may also be able to change the beneficiary to another qualifying family member.

Want to give them more flexibility?

A custodial account (UGMA or UTMA) can provide that, but the money legally belongs to your grandchild. Once they reach the age set by state law, they take control and decide how to spend it.

There’s another consideration if college is in their future. Because the money is considered the grandchild’s asset, it could reduce the amount of need-based financial aid they qualify for.

Maybe you want to help with something specific instead, such as a car or down payment on their first home.

A direct gift may be the simplest option. But once you give them the money, they decide what happens to it.

And before you give a significant gift, there’s one more question worth asking:

Can you make this gift without changing your own retirement plans?

We love seeing grandparents in a position to help their families. We also want to make sure that generosity works with the retirement you’ve spent years building.

If you’re considering a significant gift to your grandchildren, talk with us before you make it. We can help you choose a gifting strategy that matches what you want the money to accomplish.

09/30/2026

Planning to let your Medicare coverage automatically renew? You could end up paying more for a plan that no longer fits your needs.

Medicare Open Enrollment begins October 15, making this a good time to review what’s changed over the past year:

•Are you taking different prescriptions?
•Are your preferred doctors still in network?
•Has your plan changed its costs or benefits?
•Is your current drug plan still available in your area?

If you find another plan that better fits your needs, there’s no fee to switch during Open Enrollment.

Your income is also important to keep in mind during your Medicare review.

IRA withdrawals, Roth conversions, or realized investment gains can increase your income for Medicare purposes. For some retirees, that can mean paying more for Medicare Part B and Part D.

If you have questions about how your retirement income could affect your Medicare costs, give us a call. We’d be happy to help you think it through.

09/23/2026

You’ve built $1.5 million for retirement.

But eventually, the IRS may have a say in when you start taking some of it out.

If that $1.5 million is sitting in a traditional IRA, required minimum distributions (RMDs) will eventually force you to begin withdrawing money.

A Roth IRA works differently.

As the original owner, you don’t have to take RMDs during your lifetime. If you don’t need the money at 73, 75, or 80, you can leave it invested and continue giving it the opportunity to grow tax-free.

This gives you more control over your taxable income later.

Let’s say your traditional IRA balance was $1.5 million at the end of the year before you turn 73. Your first RMD would be about $56,600.

That amount is generally added to your taxable income and could also affect what you pay for Medicare through IRMAA.

This is one reason we talk about Roth conversions before RMDs begin.

Moving money from a traditional retirement account to a Roth means paying taxes on the conversion today. But in the right situation, it can reduce future RMDs and give you more flexibility later.

Of course, converting to Roth means paying taxes sooner. The question is whether doing that strategically before RMDs begin could put you in a better tax position later.

If you have significant assets in traditional IRAs or 401(k)s, it may be worth looking at what future RMDs could mean for your retirement income and taxes.

At Five Pine Wealth, we can help you determine whether a Roth conversion belongs in your retirement strategy.

09/17/2026

You spent your career building significant wealth with the goal of traveling, helping your family, and giving generously in your golden years.

But even with a substantial portfolio, spending freely doesn’t feel easy.

That anxiety usually comes from not having a clear retirement withdrawal strategy to tell you exactly how much you can direct towards those discretionary priorities.

A strategy like that accounts for your:

↪ Account types (taxable, tax-deferred, Roth)
↪ Tax bracket and income thresholds
↪ Guaranteed income
↪ Overall flexibility in case of a rough market

With that strategy in place, traveling and giving as you’ve always wanted stop relying on leftover cash flow. Instead, they’re factored into your plan intentionally so you never have to wonder.

We wrote about building a retirement withdrawal strategy that lets you spend with confidence.

Check it out on our blog:

https://www.fivepinewealth.com/how-much-can-you-spend-on-travel-and-giving-in-retirement

Not sure about how much you can spend in retirement? Give us a call, and we’ll help you find out.

They call it your “golden years” for a reason. It’s the long stretch you’ve dreamt of for years: leisurely trips with your spouse, helping your kids with a down payment, and finally writing that big check for a cause you’re passionate about.

09/11/2026

You’ve saved $3 million for retirement, yet spending $15,000 on a family trip still makes you feel uneasy.

After 30 or 40 years of saving, that hesitation makes sense. You’ve spent most of your adult life watching the account grow, so taking money out can feel like you’re undoing some of that hard work.

It also doesn’t help that, for years, retirement advice was pretty straightforward:

Save as much as you can, retire, live on the interest, and don’t touch the principal. That advice can be hard to let go of.

The rule that helped you save doesn’t explain how much you can safely spend in retirement. To figure that out, you need to consider the income you have coming in, what you want to spend, and how much you hope to leave behind.

If leaving $2 million to your children is important to you, that affects how much you spend. Having a pension and Social Security that cover most of your regular expenses also makes a difference.

What you want your retirement to look like matters too. Traveling a lot in your 60s, helping your kids or grandkids, or leaving money to the next generation all place different demands on your retirement savings.

Put those pieces together, and you can start answering the much more useful question: “How much can I comfortably spend?”

That $15,000 family trip might fit easily within your plan. When you see the numbers, it can be easier to enjoy the trip without worrying you’ll regret spending the money later.

After decades of tracking your progress by how much you’ve saved, it can take time to feel comfortable taking money out. A retirement plan can give you a clear number to work from instead of relying on the old rule about never touching the principal.

If you have questions about how much you can comfortably spend in retirement, feel free to give us a call.

09/03/2026

You can have $1 million, $2 million, or more saved for retirement and still have no idea what that means for your day-to-day life.

Can you comfortably spend $5,000 a month? $7,000? More?

Your account balance alone can’t answer that.

What you can actually afford in retirement depends on your expenses, Social Security, pensions, taxes, investments, and how long your money needs to last.

That’s why we created the Retirement Reality Check.

In about 15 minutes, you’ll use your own numbers to:

💲Estimate your monthly spending in retirement
💲See whether you’re ahead, behind, or on track
💲Identify any gap between what you’ve saved and what you’ll need

Maybe the numbers will show you where a few adjustments could make a difference.

Or maybe they’ll give you the confidence to enjoy a little more of your wealth.

Either way, you’ll have a much better idea of where you stand and what to do next.

If retirement is 5–15 years away, take 15 minutes to run your numbers and see what they say.

Start your Retirement Reality Check here.

08/27/2026

What's the point of saving for retirement if you never actually spend it?

A client of ours had spent decades doing everything "right." She saved diligently, watched her spending, and built a healthy nest egg.

When her granddaughter got the chance to study abroad, she wanted to give her $8,000 to help cover the trip.

But she almost didn't call us.

She felt guilty even considering it, like spending on something joyful instead of "necessary" was somehow irresponsible.

That guilt had followed her for years, making it hard to use the money she'd spent decades working so hard to save.

Once we walked through her plan together, she realized she'd been carrying a fear that didn't match her financial reality.

She could give her granddaughter the $8,000 and still have more than enough to support the retirement she had planned.

So she said yes.

And she still calls it one of the best decisions she's made in retirement.

That's what a good retirement plan is for.

Yes, it should help answer, "Will my money last?"

But it should also help answer, "What can I do with it?"

Have you ever held back from spending on something meaningful because it felt "irresponsible," even when you could afford it?

If guilt is the thing standing between you and the life you saved for, let's talk about it.

08/19/2026

A retiree does a $90,000 Roth conversion two years before enrolling in Medicare.

Two years later, once that income lands on the return Medicare looks at, their premium can jump from the standard $202.90 a month to $649.20 or higher, depending on their total income that year.

That tax return with a one-time higher income is two years old, but it now sets the price.

That's IRMAA, the Medicare surcharge most people don't know about until they get their notice in the mail.

It's triggered by income, not your health or your coverage.

A large IRA withdrawal, Roth conversion, or selling appreciated stock can all set it off.

These are all things you can plan for. Timing a conversion, spreading a withdrawal across two tax years, or coordinating an asset sale with the rest of your income for that year can keep you clear of a threshold.

At the very least, it can tell you exactly what crossing it will cost.

Wondering how a decision you make this year could show up on your Medicare bill in 2028? Give us a call.

You open the mailbox, and there's a letter from Medicare. Your Part B premium is going up, and not just by the usual few dollars. For retirees who saved diligently and built a solid portfolio, it can feel less like a routine adjustment and more like a penalty for doing everything right.