Trailhead Planners

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Trailhead Planners Tax-smart wealth strategies for business owners, multi-generational families, and legacy-minded retirees. We simplify your life. We help you rest easy.

With offices in Portland, Oregon and Minneapolis, Minnesota,Trailhead Planners guides individuals seeking thoughtful change toward new strategies for financial well-being. And we help you achieve sustainable financial well-being.

Is a Roth conversion worth paying more for Medicare?It's one of the questions we hear most from folks nearing retirement...
10/16/2026

Is a Roth conversion worth paying more for Medicare?

It's one of the questions we hear most from folks nearing retirement. A bigger conversion can push your income over an IRMAA threshold and bump up your premiums, so it's natural to want to steer clear.

But in one scenario we modeled, crossing that line actually came out well ahead. The difference was bigger than you might expect.

Of course, every situation is different, and there are times when it's not worth it. Morgan walks through two client examples, the timing detail that can work in your favor, and when it makes sense to hold back.

See how the math plays out: https://www.trailheadplanners.com/blog/is-a-roth-conversion-worth-a-higher-medicare-premium

10/14/2026

Here are the 5 (Simple) Steps to Financial Success:

1) Spend less than you earn.
2) Save the difference.
3) Invest in the great companies of the world.
4) Never sell.
5) Seriously, no matter how bad things look, never sell.*

People can argue that it's more complicated than this, but this is really all that is required.

*The only exception here is selling to provide for an income in retirement or for something that you have already planned for. Other than that, never touch it.

10/12/2026

Many families view 529 plans as a way for parents to save for their child’s education.

But these plans are actually one of the most flexible tools for family gifting.

Grandparents, aunts, uncles, godparents, and close family friends can all contribute to the same account or open separate accounts for the same beneficiary.

There’s no rule that the account owner must be a parent, and contributions can come from multiple people. This means a child’s education fund can gather gifts from several family members, each using their own annual gift exclusion to support the same long-term goal.

In practice, a child’s 529 plan might receive regular contributions from parents, both sets of grandparents, extended family, and others who want to help with future education expenses.

For families spreading educational support across generations, the 529 plan remains one of the most tax-efficient and flexible options.

**Remember, contribution limits, deductions, and tax rules vary by state and plan. Always review your specific plan’s details and consult a qualified tax professional before making decisions.**

We thought it might be fun to share a few questions that some of our clients have found truly impactful. - What's the be...
10/09/2026

We thought it might be fun to share a few questions that some of our clients have found truly impactful.

- What's the best money you've ever spent? Not the most expensive thing you've bought, but the spending that brought you the most joy. The trip. The experience. The thing you'd buy again tomorrow if you could.

- What's the worst money you've ever spent? The thing you'd take back if given the chance. The purchase that felt important at the moment and feels foolish from where you sit today.

- What would you not be willing to give up to make more money? Time with your family? Your morning routine? The ability to step away when you need to? The thing you'd refuse to trade away is probably the thing you value most, and maybe, the thing you should orient your life around.

- What's something you've been telling yourself you can't afford that, on reflection, you might actually be able to afford if you got clear about your priorities?

- What would your spouse or kids say you cared most about, based on how you've spent your money during the last ten years? This one might be an answer you won't like to hear, but they say a checkbook never lies, so you should at least prepare yourself for some tough truths to emerge.

It's important to note that there are no right or wrong answers to these questions. Just answers that are right, and true (maybe hard to hear, but true) for you.

While this may be a fun (or not so fun) exercise depending on the question, we do believe questions like these can help you better align your money with your purpose, so we hope you find them helpful!

10/07/2026

According to J.P. Morgan research, 53% of American households don’t retire all at once.

Many choose partial retirement, continuing some form of paid work even after officially retiring.

Common forms include:
- Reduced hours or roles with the same employer
- Consulting or freelancing in the same field
- Working retail in places like home improvement or garden centers
- Teaching or coaching in an area of expertise
- Seasonal work, allowing most of the year to be fully retired
- Turning a hobby or passion project into income

Partial retirement offers clear financial benefits. Continued earnings ease portfolio pressure during early retirement, employer benefits can help bridge to Medicare, and working reduces the need for perfect financial timing.

Beyond finances, partial retirement provides structure, social connection, purpose, and a smoother transition into full retirement.

Many pre-retirees find this gradual approach more fulfilling than retiring all at once.

10/05/2026

Many families worry that gifting too much too soon will spoil the next generation. This concern is understandable, but it helps to make a key distinction.

Smaller gifts within the annual exclusion limit (currently $19,000 per person) are unlikely to spoil anyone. They’re meaningful but modest enough to fit responsibly into the recipient’s financial life.

These gifts usually support the recipient’s existing path rather than change it dramatically.

Problems more often arise from large, sudden transfers, like surprise inheritances or unstructured windfalls, that come without preparation or context.

Consistent annual gifting, by contrast, tends to have the opposite effect and can promote healthier financial habits.

10/02/2026

A strange thing sometimes happens in retirement:

People who spent decades saving and investing to be sure they have enough still end up worrying about spending too much.

Even when their financial plan shows they’re well within their means.

It turns out the hardest part of retirement planning is often learning to trust the plan.

Americans have been calling the American Dream dead for over 200 years. So if money stress feels new, it isn't.Historian...
09/30/2026

Americans have been calling the American Dream dead for over 200 years. So if money stress feels new, it isn't.

Historian Joseph Moore joins Morgan to unpack what "getting rich" really looked like across 250 years of U.S. history, and why a lot of today's popular financial advice is younger and shakier than it sounds. The good news: he makes a real case that your odds of building wealth are better now than almost ever before.

Catch the full episode:

09/28/2026

What’s the best money you’ve ever spent?

Not the priciest purchase or the one that impressed others.
We mean the spending that, when you think back, truly brought you the most joy.

For most people, it’s not a thing. It’s an experience. A trip with someone special, a class that shifted their perspective, a meal that turned into a lasting memory.

Sometimes, it’s a wedding, a honeymoon, a surgery that eased pain, or a year of therapy that reshaped how they see themselves.

This pattern is clear: the most meaningful spending tends to be about relationships and experiences, and often, it’s surprisingly modest in cost.

We ask this question because it reveals what really matters to you, without confusion.

Most people haven’t been asked to reflect this way. They’ve talked about goals, risk, and timelines, but rarely about the spending that brought the most joy.

It’s a simple question—and one of the most insightful you can ask yourself.

09/25/2026

For married couples, one Social Security choice stands out above all others: when the higher earner decides to claim benefits.

This decision is crucial because when one spouse passes, the survivor receives the larger of the two benefits, while the smaller one ends. A bigger survivor benefit means stronger financial security for the surviving spouse, often for many years.

That’s why we always recommend couples evaluate their options together, considering both their lifespans and household income as a whole.

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5151 Industrial Boulevard #200
Edina, MN
55439

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