Trailhead Planners

Directions Website Contact the business

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.

The 2027 Social Security COLA is in: 3.6%.That's the largest adjustment since 2023 and adds about $75 a month for the av...
10/23/2026

The 2027 Social Security COLA is in: 3.6%.

That's the largest adjustment since 2023 and adds about $75 a month for the average retiree starting in January. Here are three planning notes we're sharing with the families we work with:

1. Look at the net, not the gross. Medicare Part B premiums for 2027 haven't been announced yet, and they're deducted directly from benefits.

2. A COLA keeps pace with inflation, but it doesn't get you ahead. It's designed to protect purchasing power, so it's worth reviewing whether the rest of your income plan is keeping up with your real spending.

3. Waiting doesn't mean missing out. If you're 62 or older and haven't claimed yet, COLAs still apply to your future benefit. Delaying your claim doesn't cost you these increases.

If you're within a few years of claiming and want a second set of eyes on timing, we're glad to help.

https://www.trailheadplanners.com/get-started

10/19/2026

There's interesting research showing that Social Security's share of income replacement varies dramatically by household income*.

For a household earning $40,000 before retirement, Social Security is estimated to cover 53% of its income-replacement needs. Meaning more than half of the pre-retirement lifestyle is funded by Social Security alone.

But for a household earning $300,000 before retirement, Social Security is likely to cover just 14% of its income-replacement needs. Meaning the vast majority of the pre-retirement lifestyle has to come from personal savings and investments.

The reason is pretty straightforward. Social Security benefits are capped, regardless of how much you earned. For lower earners, the capped benefit represents a large percentage of pre-retirement income. For higher earners, the same capped benefit represents a much smaller percentage.

For high-earning pre-retirees, this has practical implications: First, you shouldn't assume that Social Security will provide more than it actually will. And second, the more reasonable your standard of living is, the more of your lifestyle Social Security will provide for.

The key, as always, is running the numbers—both what you can expect from Social Security and what you plan to spend. That way, your expectations should, hopefully, align with reality.

*From J.P. Morgan's Guide to Retirement

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.

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:

Address

5151 Industrial Boulevard #200
Edina, MN
55439

Website

Alerts

Be the first to know and let us send you an email when Trailhead Planners posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to Trailhead Planners:

Shortcuts

Share

Category