Most people think about taxes once a year.
Not because they do not care.
Because the system trains you to treat taxes like a yearly project.

Get the forms. File the return. Move on.

And when that is your approach, the outcome can feel like a surprise.

“I did not expect to owe this much.”
“Why did our refund drop?”
“How did we end up in a higher bracket?”

That is one downside of only looking at taxes through the lens of tax season.
It can turn taxes into a reaction instead of a plan.

Because in retirement, the biggest tax decisions are usually not about finding one more deduction.
They are often about how decisions stack together over time, and where your income comes from.

When you take income.
Which account it comes from.
How much shows up on your return in a given year.
And how that interacts with Medicare premiums, Social Security taxation, and future required distributions.

Your CPA is essential. Annual tax filing is essential.​
It tells you what happened and helps you file accurately.

Tax planning is different.​
It is more forward-looking.
It helps you evaluate upcoming decisions using today’s rules, thresholds, and tradeoffs.

So there are really two different conversations.

1) Annual tax filing: looking backward

This is what your CPA does, and it matters.

They take what happened last year (income, deductions, credits, forms, documents) and file an accurate return.
It answers questions like:

• What do we owe (or get refunded)?
• Did we withhold enough?
• Were there any missing forms or reporting issues?

Annual tax filing is a scoreboard.
Important. Necessary. But still a scoreboard.

2) Annual tax planning: looking forward

Tax planning is not focused on last year’s return.
It is focused on the years ahead.

In retirement, that longer view can matter because you are often managing multiple income sources and multiple account types over time.

Not in a “secret loophole” way.
In a coordination way.

It is the difference between paying what you owe and making decisions that may increase taxes or reduce flexibility later, without realizing it.

Here are a few common areas that are worth reviewing.

Taking withdrawals without coordinating the account mix

Retirement often comes with multiple “buckets” (pre-tax, Roth, taxable). If withdrawals are not coordinated, you can create higher taxable income in one year and limit options in future years.

The point is not “never touch pre-tax accounts early.” Sometimes that is the right move.
The point is that the order and timing can matter, and it should fit your broader plan.

Triggering higher Medicare premiums without realizing it

Medicare premiums can increase when income crosses certain thresholds (often called IRMAA). The frustrating part is timing. Premiums are generally based on income from a prior year, so the increase can feel disconnected from the decision that caused it.

A one-time event can do it.
A Roth conversion can do it.
A large IRA withdrawal can do it.
A capital gain can do it.

None of those are “bad” by default.
But they are usually better made with eyes open.

Letting required distributions become a future constraint

Required minimum distributions (RMDs) are not a problem for everyone. But for some retirees, they can push taxable income higher later in life, especially if pre-tax balances grow for years without a withdrawal strategy.

That can also affect other areas, such as:

• Marginal tax brackets
• How much Social Security is taxable
• Medicare premium tiers
• The number of lower-income years available for strategic planning moves

Again, not a crisis for everyone.
But often worth thinking about before RMDs begin.

Creating avoidable tax spikes because there was no plan for higher-impact years

Some years naturally have more planning “leverage” than others, for example:

• Retirement (income drops or changes shape)
• Starting Social Security
• Pension decisions
• A large home sale
• Inheritance
• Widowhood (often an overlooked tax change)

In many cases, planning is about smoothing income where possible instead of bouncing between low-tax years and high-tax years.

The real shift: stop viewing taxes as a yearly task

We prefer to look at taxes as part of a coordinated system.
Not just a return.

A system that connects:

• Withdrawals
• Investment cash flow
• Current tax rules and known thresholds
• Medicare premium tiers
• RMD timelines
• Social Security taxation

So decisions today can be evaluated in the context of the long-term picture.

And yes, the goal is often to reduce unnecessary taxes over time, when possible.
No guarantees. No crystal ball. Tax laws can change.

But you can still make more informed decisions using today’s known rules and thresholds, and by understanding the potential ripple effects before making a big move.

A simple way to think about it:

Annual tax filing asks: “What happened?”​
Tax planning asks: “What might happen next, and what options do we have?”

If you are already retired or close to it, that second question is often the one people overlook.

Because retirement is not one tax year.
It is a long series of tax years.
And small decisions repeated over time can add up.

If you want, reply and tell me which situation you are in right now:

• Still working, retiring soon
• Recently retired
• Retired for a while
• Unsure, but taxes feel messy

And I can share a few general planning topics people commonly review at that stage.

We’d love to hear your thoughts! Just reply to this email with any questions or feedback.
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Thanks for tuning in!
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​Keeping wealth in focus,

The MY Wealth Management Team