Trailhead Planners

06/17/2026

Consistency is so important in investing.

There are a lot of different investment approaches than can work in the long run.

But none of them work if you don’t stick with it.

06/12/2026

There are many reasons why we love owning our own financial planning practice.

But we have one clear-cut favorite aspect to it:

We get to choose our own clients.

We're not meeting someone else’s growth objective.

We're not an expense on someone else’s P&L.

And no one else is forcing clients onto our plate to meet their objectives.

Why is this so important?

Because it allows us to be selective and only work with clients that we're genuinely excited to serve.

The result?

We can genuinely say that we love working with each of our clients.

Which sets the foundation for longevity in the relationship.

06/10/2026

There are so many tools to minimize estate taxes:

- Credit shelter trusts
- Lifetime gifting
- Discounted valuation using minority interests
- Discounted valuation using lack of marketability
- Irrevocable life insurance trusts
- Grantor retained annuity trusts
- Intentionally defective grantor trusts
- Spousal lifetime access trusts
- Charity remainder trusts
- Family limited partnerships to leverage valuation discounts

Business owners in particular have the opportunity to leverage several of these strategies.

But you have to start planning early.

You have to be surrounded by the right team of skilled professionals.

And you have to coordinate your estate plan with your personal financial plan, your income tax strategy, and your business exit plan.

06/08/2026

The most important question to ask for any portfolio:

“What is the goal it is intended to fund?”

The second most important question:

“What is the appropriate asset allocation for accomplishing that goal?”

Start with the end in mind, and work backwards from there.

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.