Trailhead Planners

06/03/2026

What is one of the biggest risks to a successful retirement?

A bad market during the earliest years after you stop working - also called "sequence of return risk".

Without a thoughtfully determined portfolio distribution strategy and asset allocation that are prepared to handle such a scenario, it could put your retirement goals and lifestyle at risk.

For our clients, we use a "dynamic distribution" approach with pre-determined guardrails that guide our portfolio distribution decisions.

Then we set a target asset allocation that is tied to each client's financial plan and risk capacity, rebalancing back to this target through any downturns.

Having a pre-determined plan for handling bad markets - supported by evidence-based strategies and a personal financial plan - is the way.

06/01/2026

Did you know summer is one of the best times to reduce your tax bill?

About two weeks ago, we wrapped up spring meetings for all of our clients.

Up next?

Summer tax planning.

For each of our clients, we review their prior year tax return and run tax projections for the current year. This helps us identify planning strategies to reduce their lifetime tax bill and ensure they have no unpleasant surprises next April 15th.

Excited to keep building out our processes to add more value for our clients!

05/29/2026

Financial planning should be comprehensive — not just investments.

We help clients tackle every key aspect of their financial life:

✅ Retirement timing & savings targets
✅ Minimizing lifetime taxes
✅ Which accounts to save into (and draw from in retirement)
✅ Social security & pension decisions
✅ Retirement spending & cash management
✅ Debt, investments, insurance & estate planning

If you'd like to talk through where you stand, schedule a free exploratory call below!

Not sure if your current advisor is giving you everything you need? This call is your chance to get a straight answer. We'll talk through your situation, what you're looking for, and whether Trailhead Planners might be a better fit. No pressure, no obligation.

05/27/2026

Where should you be saving your money?

We love the framework in this chart.

Start by building your cash reserves and gettting the employer match on your 401(k).

Then pay down higher interest debt... especially at today's higher rates!

After that, focus on tax-advantaged accounts. This can help lower taxes today and also set you up for lower taxes in retirement.

Very few people appreciate the tax benefits of Health Savings Accounts, but it should be one of your top priorities.

Other common tax-advantaged accounts include:
- 401(k) plans
- Deferred compensation plans (including 457s)
- Roth IRAs
- 529 plans
- Employee stock purchase plans
- Self-employed retirement plans
- Cash balance pension plans

Once you have the basics down - building your cash reserves, getting the employer match in your 401(k), and paying down debt - and you have enough cash flow to fund multiple savings strategies, it is important that you start thinking about longer-term tax planning.

You should be saving at least 20% per year to stay on track for retirement.

But it's also important that you are thoughtful about WHERE you are putting your savings.

Getting the order right can make a big difference.

Start at the bottom of the list and work your way up!

05/25/2026

Tax planning in the different stages of retirement:

Pre-retirement 👉 Fund tax-favored accounts

Early retirement 👉 Manage Social Security/Medicare taxation + fill brackets in low income years

Middle retirement 👉 RMDs + charitable bunching

Late retirement 👉 Tax efficiency for estate plan

05/22/2026

Things money can be traded for:

- Time
- Energy
- Experiences
- Assets that grow in value
- Assets that decline in value

Financial planning is the process of being intentional with these choices.

05/20/2026

Be prepared for volatility.

It's one of our core investment principles.

If you are retired or near-retirement, our rule of thumb is to hold enough bonds in your portfolio to cover the next 5-10 years of distributions. And those bonds should be either short-term or match the duration of your cash flows.

Why?

Because this helps protect your portfolio - and retirement income - from a severe market downturn.

We love stocks. And our clients know well that we regularly preach the virtues of holding them for the long run.

But they are volatile.

And sometimes they have steep declines and extended stretches of poor performance.

05/18/2026

The best financial plans are simple.

▫️Know what you spend

▫️Have an annual savings or portfolio withdrawal goal

▫️Use all of the tax reduction strategies available to you

▫️Build a cash reserve

▫️Hold diversified stocks for a long time

▫️Know when you need to cut back portfolio withdrawals in a bad market

The sign of a good plan isn’t COMPLEXITY…

It’s CONSISTENCY.

05/13/2026

Want to gain an investing edge over your neighbors?

Here’s one: Stop looking at your portfolio.

The time horizon for our portfolios is measured in years and decades. Meanwhile, market prices can swing wildly day-to-day, and market pundits make you feel like there’s always something to do.

It may seem counter-intuitive, but research has shown that the more frequently we look at our investment accounts, the more likely we are to make poor investment decisions. With our portfolios, the enemy isn’t the market. It’s our own behavior.

So what should you do? Have a clearly defined investment plan, laid out in a written investment policy statement, built around a goal-based financial plan.

Avoid the noise. Stick to your plan.

05/11/2026

The honest (and slightly surprising) answer to how much you need to retire.

Most retirement calculators have us chasing a massive "finish line" number that feels impossible. But honestly? Life isn’t linear, and the math usually misses some big factors.

Between the reality of Social Security and the "spending smile," your goal might be a lot lower than you think and you’re likely closer to "enough" than the headlines lead you to believe.

Check the comments for the link to read more! 👇