Retirement Planning
Retirement planning where your investments and your taxes finally work together.
You have saved diligently. Now the hard questions start: when to retire, how to turn a lifetime of savings into steady monthly income, when to take Social Security, and how to avoid handing the IRS more than necessary over the next 30 years. Those questions do not have textbook answers. They depend on your accounts, your tax brackets, your health, and what you actually want the next chapter to look like.
At Shetland Financial, the person managing your investments is also a CPA. That is unusual, and it matters more in retirement than at any other stage of life. Your withdrawal strategy, your tax plan, and your portfolio get built as one thing instead of three, by one person who sees all of it.
The decisions that shape your retirement income
Which accounts you draw from, and in what order. Most retirees hold some mix of taxable, tax-deferred, and Roth money. Pulling from them in the wrong sequence can cost tens of thousands of dollars over a long retirement, and it is invisible while it is happening. We map the order and revisit it every year as your income and the tax law change.
When to convert, and how much. The window between the year you stop working and the year required minimum distributions begin is often the cheapest tax opportunity you will ever have. Converting the right amount in the right years can lower your lifetime tax bill and shrink the RMDs that would otherwise push you into a higher bracket at 75. Converting too much, in the wrong year, does the opposite.
When to claim Social Security. Claiming early, claiming at full retirement age, and waiting until 70 produce very different lifetime outcomes, and the right answer depends on your other income, your spouse’s benefit, and your tax picture. We run the comparison with your actual numbers rather than a rule of thumb.
What the plan costs you in taxes. Medicare IRMAA surcharges, the taxation of Social Security benefits, and capital gains stacking all turn on your reported income. A plan built without a CPA in the room tends to miss these until the bill arrives.
Why one roof changes the answer
Most people keep their investments at one firm and their accountant at another, and the two never speak. In your working years that costs you a little. In retirement it costs you a lot, because nearly every retirement decision is simultaneously an investment decision and a tax decision. A withdrawal is a tax event. A Roth conversion is a tax event. Rebalancing a taxable account is a tax event.
We are a CPA firm and a registered investment advisor in the same office. When we adjust your portfolio, we already know what it does to your bracket. When we plan your return, we already know what is in your accounts. Nothing gets handed off and nothing falls between two firms.
Rolling over a 401(k) on the way in
Most people arrive at retirement with money still sitting in one or more former employer plans. Consolidating it is usually sensible, but a rollover is a tax event waiting to be handled either well or carelessly. Direct trustee-to-trustee transfers avoid withholding entirely; taking a check does not. Appreciated employer stock inside a plan has its own treatment that is easy to forfeit by rolling everything over reflexively. Our 401(k) rollover page compares the four options and the mistakes that cost real money.
The costs that are driven by your reported income
Retirement income planning is not only about the tax rate on the withdrawal. Several other costs key off the same number, and they tend to surprise people the first time.
Medicare surcharges. Premiums for Parts B and D rise in steps once income passes certain thresholds, and the determination looks back at a prior year’s return. A single large Roth conversion or capital gain can raise your premiums two years later, which is a genuinely unpleasant way to learn about the rule. It is manageable if it is planned around, and cliff-edged if it is not.
How much of your Social Security is taxable. The taxable portion of your benefit depends on your other income, so an additional withdrawal can raise your tax bill by more than the withdrawal alone would suggest.
Capital gains stacking. Long-term gains sit on top of your ordinary income for rate purposes. The same gain can be taxed at very different rates depending on what else you took that year.
None of these are exotic. They are simply invisible unless someone is looking at the whole return while making the investment decisions, which is the argument for having one firm do both.
Who this is for
Most of the people we do this work for are within five to ten years either side of retiring, with meaningful balances in a 401(k) or IRA and a real question about how to turn that into income without overpaying tax. If that is roughly where you are, our pre-retirees and retirees page walks through what the years around retirement look like and the order the decisions come in.
You work directly with Kevin Dodgson, CPA, CFA, CFP®. Not a call center, and not a junior advisor you meet once.
What it costs
Fee-only and flat-fee. You see the price before we start. We do not sell annuities, we do not earn commissions, and there are no products in the background. Our only compensation comes from you, which means our advice has nothing riding on it except whether it is right.
What you get
Tax-efficient retirement income and withdrawal sequencing. We decide which accounts to tap, and when, to stretch your savings further.
Roth conversion and Social Security timing. Small timing decisions now can save a great deal over a 30-year retirement.
One fiduciary for investments and taxes, not two firms guessing. Your portfolio and your tax plan are built by the same person.