2026 Changes You Can’t Ignore: Social Security, Tax Rules, and Withdrawal Realities, Ep #202

Welcome to 2026! A new year brings a fresh set of rules for your retirement savings, and not all of them are straightforward. With the turning of the calendar comes changes to contribution limits, Social Security adjustments, and new tax mandates that could catch you off guard if you aren’t paying attention.

In this first episode of the year, I break down exactly what is changing for 2026, from the “good news” of higher contribution limits to the “bad news” of Medicare premium hikes that might eat up your entire Social Security cost-of-living adjustment. I also dive into a controversial new rule from the Secure Act 2.0 that forces high earners to change how they save in their 401(k)s, removing the choice of pre-tax savings for many.

We also tackle some fantastic listener questions, including a look at why Target Date Funds had a “lucky” year in 2025 (and why I still don’t recommend them), and I dismantle a dangerous misconception about retirement withdrawals, the “Mayonnaise Jar” math that convinces retirees their money will last 20 years when, in reality, inflation and life have other plans.

You will want to hear this episode if you are interested in…

• (00:23) Intro to 2026 Changes.
• (04:36) Social Security COLA vs. Medicare Premiums.
• (06:40) New IRA and 401(k) Contribution Limits.
• (10:24) The New “Roth Catch-Up” Mandate for High Earners.
• (18:57) New Charitable Deduction Rules.
• (20:03) Listener Q: Target Date Funds Explained.
• (29:12) Listener Q: The “Mayonnaise Jar” Withdrawal Mistake.

The “Fake” Raise: Social Security vs. Medicare in 2026

We start the year with what sounds like a win: a 2.8% Cost of Living Adjustment (COLA) for Social Security recipients. However, before you start budgeting that extra cash, you need to look at the other side of the ledger.

Medicare Part B premiums have jumped by nearly 9.67%, rising to $202.90 a month. For many retirees, this increase will come directly out of their Social Security check, effectively wiping out the “raise” they thought they were getting. It is a reminder that healthcare inflation often outpaces general inflation, and your plan needs to account for that reality, not just the headline numbers.

The $150k Trap: New Mandatory Roth Rules

One of the biggest changes for 2026 comes from the Secure Act 2.0, and it impacts high earners. If you earned $150,000 or more in FICA wages in 2025, you no longer have a choice on how you make your “catch-up” contributions.

Uncle Sam now mandates that your catch-up contribution (the extra $8,000 you can save if you are over 50) must go into a Roth 401(k). This means you lose the immediate tax deduction on those dollars. It is a way for the government to grab more tax revenue now rather than later, and for many savers, it removes the flexibility to design a tax strategy that fits their specific needs. If your employer doesn’t offer a Roth option, you might be out of luck entirely.

Why “Cookie Cutter” Investing Still Fails (Even When It Wins)

A listener asked why their Target Date Fund performed so well in 2025. The answer lies in a rare alignment of international markets and bond performance that boosted these funds last year.

But one good year doesn’t change my fundamental problem with these funds: they are “cookie-cutter.” They treat every 65-year-old exactly the same, ignoring your personal goals, your risk tolerance, and your income needs. It’s like walking into a car dealership and being told you have to buy a minivan just because everyone else your age is buying one. You deserve a plan customized to your life, not a default setting based on your birth year.

The “Mayonnaise Jar” Math Mistake

Finally, I address a listener who believed he was set for 20 years because he could withdraw $50,000 a year from his $1 million nest egg until it hit zero. I call this “Mayonnaise Jar” math, assuming you can just pull cash out of a stagnant jar until it’s empty.

This logic fails because it ignores inflation. As we saw in 2025 with beef prices jumping 20%, the cost of living does not stay flat. $50,000 today will not buy $50,000 worth of goods in ten years. If you don’t have your money invested to grow and outpace inflation, you aren’t planning for a 20-year retirement; you’re planning to run out of purchasing power long before you run out of money.

Resources & People Mentioned

• 3 Steps to Retirement Planning
• Retirement Budgeting Tool