Five Pine Wealth Management

06/11/2026

One of the first questions we ask new clients about retirement income isn't what they're expecting:

"Which account are you planning to pull from first?"

It sounds like a small detail. But over a 20-year retirement, it's one of the bigger tax decisions you'll make.

The years before Social Security starts are often your lowest-income years. That window can be ideal for Roth conversions or drawing down your IRA at a lower tax rate.

Once Social Security kicks in, it pushes your taxable income higher. That changes how you want to draw from pre-tax accounts.

And a traditional IRA left untouched too long can trigger large Required Minimum Distributions at age 73, potentially bumping your tax bracket and adding Medicare surcharges you didn't plan for.

There's no universal answer here. The right withdrawal sequence depends on your specific accounts, timeline, and year-by-year income picture — which is exactly why this is something to plan before retirement, not after.

Have questions about your withdrawal strategy? Give us a call — we're happy to think through it with you.

06/05/2026

Most people spend 30+ years building their retirement savings.

But have you thought about what happens to those savings once the government starts taking its cut?

RMDs kick in at 73 (or 75 if born in 1960 or later).

Social Security becomes partially taxable.

Medicare starts charging higher premiums based on income from two years prior.

Most retirees know these rules exist. What catches them off guard is how many of them start stacking together, potentially pushing them into a tax bracket they never anticipated.

Where you saved matters just as much as how much you saved.

A portfolio built entirely in pre-tax accounts like a traditional 401(k) or IRA looks great on paper, but every dollar you pull out in retirement counts as taxable income — even if it’s income you don’t need.

Add Social Security on top of that, and suddenly your taxable retirement income may look very different from what you expected.

This is exactly why tax strategy conversations shouldn't wait until 65.

Roth conversions, diversifying across account types, and understanding how each income source gets taxed are decisions best made in the years before the triggers begin, not after.

Wondering what your retirement tax picture looks like?

That's a great question to bring to your next planning conversation.

Have a question about retirement tax planning? Give us a call — we're happy to help.

05/29/2026

Helping your adult child financially can feel like the right thing to do.

But what happens when it puts your retirement at risk?

Imagine this: A couple in their early 60s with decades of disciplined savings.

Their son owned a small business until COVID hit, and his clients disappeared almost overnight.

Work slowed. Debt piled up. The stress became overwhelming.

Eventually, he came to his parents for help.

Every instinct they had told them to step in. But the money he needed would have to come from the retirement savings they had spent 30 years building.

Suddenly, they found themselves sitting at the kitchen table with questions no parent wants to face:

If we don't help, who will?
If we do help, what does this mean for our future?
How do you say no to your child when you know they're hurting?

Before making a decision, they slowed down and worked through a few practical questions:

✨ How much can we realistically afford without putting our own future at risk?

✨ Is this a one-time situation, or could it become ongoing?

✨ Should this be structured as a loan, a gift, or something else entirely?

In the end, they chose to help, but with a clear plan and defined limits around what future support would look like.

Family and money can create some of the hardest decisions people ever face, because love and financial reality do not always line up neatly.

Have you ever faced a financial decision involving family that felt harder emotionally than financially?

Share your thoughts in the comments.

05/21/2026

Saving too much is a real problem.

We just don't talk about it enough.

We've worked with clients who had healthy portfolios, zero debt, and retirement accounts most people would envy, yet they hadn't taken a real vacation in years.

Every time they got close to booking something, the same thought stopped them: Not yet. I'll wait until things feel more certain.

But that feeling of "not yet" doesn't go away when the number gets bigger.

It just moves the goalposts.

The discipline that builds wealth can be the same thing that keeps you from enjoying it.

In our latest blog, we explore:

•Why some high earners struggle to spend money they've worked hard to build

•The psychology behind over-saving (and why it's more common than you'd think)

•How spending with intention, on things that actually matter to you, creates a better balance

If you've ever felt guilty spending money even when you know you can afford it, this one's worth a read.

Link in bio. Or reach out anytime — we'd love to talk through it with you.

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.

05/14/2026

You can afford the trip.

But that doesn't always mean you should take it.

We recently sat down with a couple planning a big international vacation. They'd had a busy stretch of life and felt like they'd earned it.

Early in the conversation, we asked them one simple question:

"How does this fit with everything else you want to accomplish over the next 10 to 15 years?"

They could afford the trip. But once they started thinking out loud, they realized it wasn't the only major expense on the horizon.

A second home. Helping their kids with down payments someday. Each goal made sense on its own, but together, they started to compete.

After thinking it through, they found a middle ground and made a few adjustments. They revised their travel budget and set a clearer timeline for buying the second home.

Short-term wants and long-term goals can be looked at together without competing for attention.

When was the last time you held a big purchase up against your retirement? Was it a green light or more of a reality check?

Let us know in the comments.

05/08/2026

How much wealth do you need before the financial anxiety goes away?

We see clients who have saved $750K, $1M, $2M, or more…and they still have their own worries:

➤ Running out of money in their 90s. A 65-year-old couple today has a reasonable chance that one of them will live past 90. That's 25+ years your money needs to work.

➤ A bad first few years of retirement wrecking an otherwise solid plan. If the market drops significantly right after you stop working, drawing income while your portfolio is down can do lasting damage. The sequence matters as much as the average return.

➤ Healthcare costs they didn't see coming. Medicare covers a lot, but not everything. Long-term care, dental, vision, and out-of-pocket costs can run tens of thousands of dollars a year. Most people underestimate this by a wide margin.

➤ Adult children who need financial help. Parents who've done everything right sometimes find themselves subsidizing adult kids — and wondering how to help without compromising their own retirement.

Having money solves some problems, but not all of them. The clients who sleep soundly at night aren’t always the wealthiest ones. Instead, they’re the ones with a plan that accounts for what keeps everyone else up.

Have a question about your retirement finances? Send us a DM!

04/30/2026

If someone asked you what your 457 was invested in, could you answer?

For many first responders, the focus (rightfully) has been on your WA LEOFF Plan 2 or ID PERSI.

But your 457 tends to get the “I’ll deal with it later” treatment.

Until later gets closer.

We’ve been having more conversations lately with first responders who are within 5 - 10 years of retirements and there’s a common theme:

👉They know the balance
👉They’re glad they contributed
👉They’re not completely sure how it’s invested

How your 457 is invested has a direct impact on your flexibility, your timing, and how comfortably you retire, and that impact grows the closer you get to hanging up the uniform.

If you’d like to learn more, check out this week’s blog post: What’s Inside Your 457? (And Why It Matters More Than You Think).

Take a few minutes and give it a read. It might answer a question you didn’t even know you had.

Send us a message or give us a call, and let’s talk about your 457 or any other retirement questions you might have.

#457

Like many first responders in Washington and Idaho, you probably have a pretty solid grasp of your "Plan A." Between the WA LEOFF Plan 2 or ID PERSI, you’ve spent your career earning a guaranteed monthly pension. It’s the foundation of your retirement — the steady paycheck that arrives regardl...

04/16/2026

She took care of everything.

She managed the investments, insurance, and estate planning. She knew where every account was, every policy number, and every password.

But at 61, she had a stroke.

Her husband was a successful business owner who trusted her completely with their personal finances. When the time came, he didn’t know where to start.

Here's a quick list of things every spouse should be able to find in 15 minutes or less:

✔️ Your will and trust documents — where they're stored physically AND digitally

✔️ All investment and retirement account names and numbers

✔️ Life insurance policies: carrier, policy number, and death benefit amount

✔️ Password access or written instructions for online accounts

✔️ The name and contact info for your financial advisor, CPA, and attorney

You don’t have to manage every part of your finances together, but both spouses should be able to easily access the information.

We’ve guided many families through this process. It all begins with a single conversation and a central place to keep everything organized. There are even tools like Nokbox made just for this purpose.

Be honest — which one would stump you? Share your answer in the comments.

04/09/2026

Have you ever felt the itch to "do something" after a big market drop? 😬

Move to cash, wait for things to "settle down," or maybe just pause and see what happens.

We see this all the time, especially after sharp declines or big rallies. When markets move, it feels like action is required.

This is the moment that often shapes the outcome.

Trying to time the market often leads to decisions driven by emotion, not strategy. And more often than not, it means missing the recovery that tends to follow.

A solid plan is built to withstand headlines, not react to them. 💪

Long-term success usually comes from staying consistent, not from getting in and out at the "right" time.

Staying the course doesn't always feel easy in the moment, but it's often what gives your plan the best chance to work over time.

What's your instinct during a market drop — stay put or make a change? Let us know your thoughts.

04/01/2026

Most first responders retiring at 55 don't realize they're about to make a costly mistake with their 457.

A firefighter retires, pension kicks in, deferred comp looks solid — so they roll everything into an IRA.

Clean, simple, organized.

Until they realize they just gave up penalty-free access to their money before age 59½.

A 457 plan works differently from most retirement accounts. Once you leave your job, you can withdraw without the 10% early withdrawal penalty, making it a powerful bridge for the early retirement years.

Instead of rolling over everything, some retirees:

-Keep a portion of their 457 for early-retirement cash flow

-Roll the rest into an IRA for long-term growth

-Let their pension cover the foundation

Different accounts. Different purposes. More flexibility.

You've spent your career protecting others. This is how you protect your retirement.

Check out our latest blog - to learn more about the best strategies for your 457 account.

Did your HR department or union ever explain how your 457 works in retirement, or were you just handed paperwork and left to figure it out? We'd love to hear from you.

Many first responders in Washington and Idaho can realistically retire early. Thanks to pensions like WA LEOFF Plan 2 or ID PERSI, disciplined savings, and a long career of service, retiring at 55 is common.