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Exit 59 Advisory

Helping You Enjoy Your Wealth Today Without Having to Worry About Running Out Tomorrow.

09/30/2026

The tax work done before April 15th is mostly just reporting. Q4 is where you actually save money. Before December 31, here are five moves worth looking at for retirees:

Roth conversions

Harvesting capital gains at 0%

Staying below Medicare thresholds

Making charitable gifts directly from your IRA.

Funding a retirement account with your retirement side hustle.

Which of these are you already thinking about this year?

09/23/2026

Many people who inherited an IRA after 2019 don't know there's a 10-year clock ticking on it. The SECURE Act changed the rules. That money can't just sit there anymore. It has to be fully distributed within 10 years of the date of death for the vast majority of beneficiaries, and depending on when the original owner passed, annual withdrawals may be required along the way. The best distribution strategy is based on what your tax rates look like. High tax years typically mean you should take less. The opposite is true in years where your rate is low. If you inherited an IRA recently, do you know which rules apply to you?

09/16/2026

Most people don't realize their Medicare premium is based on income from two years ago. So, a home sale, a Roth conversion, or a consulting gig today could quietly raise your bill in 2028. The coverage doesn't change. Just the cost. And here's the part most people miss: you can appeal it for certain life-changing events. Note: Roth conversions or a home sale don't qualify but retirement does! Form SSA-44 exists for exactly this reason. Have you ever gotten an IRMAA letter and just... paid it?

09/09/2026

Most retirees who consult don't realize they can still shelter income in a retirement plan.

If you earn self-employment income, even part-time, you're likely eligible. There's one catch: your Schedule C has to show a profit. No profit, no contribution.

Once you're in the black, the options open up. A Solo 401(k) lets you contribute as both the employee and the employer, up to $72,000 in 2026, $80,000 if you're 50-plus, and weirdly, $83,250 between 60-63. That's a real tax deduction on consulting income you may not need day-to-day.

If your consulting practice really takes off, defined benefit plans go even further. It's not uncommon to fund those with a few hundred thousand dollars per year over about five years. That's a big lever for deferring taxes into later, hopefully lower, tax years.

The deduction is nice today. But you want to make sure you're not creating a bigger problem when the money comes out. Are you setting up future RMDs (required minimum distributions) that actually result in a bigger tax hit?

If you're doing any paid work in retirement, what does your Schedule C look like this year?

08/14/2026

SECURE 2.0 is fully phased in now, and I'm still chatting with folks who don't know their
RMD age changed.

If you were born in 1960 or later, you don't touch that pre-tax money until 75. That's not a small thing. It reshapes years of planning.

The missed RMD penalty dropped too. Still hurts, but less than it used to.

And Roth 401(k)s? No more RMDs. Same freedom Roth IRAs always had.

Which of these changes caught you off guard?

08/07/2026

Some retirees overpay taxes not because they made bad decisions, but because nobody told them about the other options. The gap between your last paycheck and your first Social Security check is the closest thing to a sale tag retirement has. Lower income, lower rates, real opportunity to shift money into accounts that won't get taxed again. Most people let it pass without knowing it existed.
What would you do differently if someone had told you sooner?

07/31/2026

The flight attendant said it before we took off: put your own oxygen mask on first.

Same rule applies to giving money to your kids in retirement.

Before you write a check, ask yourself (or your planner) these two questions? Can you actually afford it? That’s the oxygen question. After accounting for 30 years of expenses and a potential long-term care need, your balance sheet may not be quite as robust as it seems today. And, will the money help them? A financial gift can be a rope or it can be quicksand depending on the recipient.

What's the biggest factor your family would need to think through before making that call?

07/24/2026

I watched a couple walk away from selling their “forever home” because they were convinced the tax bill would wipe out too much of the proceeds.

Turns out, they would have owed taxes on about $40,000 of gain. On a $1.2 million sale.

The Section 121 exclusion lets most married couples exclude up to $500,000 of gain from their primary residence. But I've seen people freeze up over imaginary tax bills or, worse, sell without planning and leave money on the table.

If you're thinking about downsizing, have you run the actual numbers on what you'd owe?

07/07/2026

Downsizing in retirement but not sure whether you should sell or rent out your “forever home?” Most people frame it wrong from the start. Keeping it as a rental sounds great until you're fielding a 9pm call about a broken toilet from three states away. That's not passive income. That's a second job. The real questions: Does the rent cover 1% of what the home is worth today? What happens to your tax exclusion if you rent it out for too long? And honestly, is there any chance you move back? What's the one thing making this decision harder for you?

06/30/2026

Most people spend years planning the finances for retirement and about ten minutes planning the life. It’s like spending ten hours searching for flights to a destination but having absolutely no plan for once you get there.

Who are you when the job title is gone? What does Tuesday at 2pm look like? Who are you calling to grab lunch? I urge you to sit with those three questions before you hand in your keys. What's the first honest answer that comes to mind?

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