When people reach out to me, they usually want the answer to one fundamental question: "Can I retire, or do I need to change my strategy?"

In most cases, once we dig into the numbers, the answer is a resounding "Yes." You can retire. The problem isn't the math; it’s the "Complexity Infinite Loop" that traps retirees before they even get started.

Today, I want to show you how to break that loop by looking at the only two things that actually matter in retirement: Time and Money. You can watch my YouTube video on this topic here.

The Complexity Infinite Loop

Does this sound familiar? You start thinking about retiring at 62, but then you hit a wall:

1. Healthcare: "What do I do for insurance before Medicare at 65? It's expensive."

2. IRMAA: "But wait, if I retire, I need to look out for IRMAA (Income Related Monthly Adjustment Amount). If my portfolio spits off too much income, my Medicare premiums spike."

3. Taxes: "If I'm in a low tax bracket before Social Security kicks in, I should do Roth conversions. That’s smart, right?"

4. The Loop Closes: "But if I do Roth conversions, that spikes my income, which triggers the IRMAA penalty, which takes me right back to... Healthcare costs."

You can spend months spinning in this circle. To get out, we have to simplify.

1. The Strategy for Time: Guarding Your 118 Hours

We all have 168 hours in a week. If you sleep 50 of them, you have 118 hours awake. For the last 30 or 40 years, about 50 of those hours were consumed by working, commuting, and thinking about work.

When those 50 hours suddenly become "free," well-intentioned people will try to fill them for you. You’ll get asked to join the HOA board, help with a neighbor's project, or volunteer for things you aren't passionate about.

To avoid becoming "busier than when I was working," you need two tools:

• The Power of "No": This should be your default response. It’s hard to do firmly and with grace, but it is the only way to protect your retirement.

• The "Misogi" & Kevin’s Rule: Borrowing from entrepreneur Jesse Itzler, try a "Misogi"—one big, difficult endeavor each year that defines your calendar. Combine this with "Kevin’s Rule": schedule one adventure every six weeks. If you have these on the calendar first, it’s much easier to say, "I can’t help with that HOA project; I’m already booked."

2. The Strategy for Money: Top-Down vs. Bottom-Up

Most of the financial industry uses a "Bottom-Up" approach. They ask for your goals, throw them into a "Monte Carlo" simulation, and tell you that you have an "83% chance of success." These models are highly sensitive—garbage in, garbage out.

Instead, I recommend a "Top-Down" approach to find immediate clarity:

1. The 4% Check: Take your total investment portfolio (all accounts) and multiply it by 4%. (Use 3% if you are conservative, 5% if you are aggressive).

2. The 1040 Comparison: Take that number and compare it to Line 11 of your last Form 1040 (your Adjusted Gross Income).

For many people I talk to, that 4% number is significantly higher than what they were actually living on while employed. If that’s you, take a breath. You are going to be okay. We don't need to reinvent your life; we just need to optimize the "tweaks"—like Roth conversions and IRMAA—to make sure you don't run over a tax cliff.

Breaking the Loop

Retirement planning shouldn't feel like a rabbit hole. It should feel like a transition into the most valuable use of your time. If you find yourself spiraling in the complexity loop and need a human to help you find the "top-down" view, let's talk.

At Barrett FP LLC, we offer expert financial planning on an hourly basis, focused entirely on helping you achieve goals based on what is truly important, not just what is urgent.

Ready to get out of the loop? See if we’re a good fit.