I have admitted a few times the sins of my investing past. Today’s post is another one of those “confessions”—the kind where I describe exactly what I should do, while simultaneously struggling to actually do it. For any new Padawans joining the journey, you can click on my previous moments of weakness here:

• The ‘Rabbit Investor’: My Path to Early Retirement
• The Price of (Toilet) Paper Wealth
• The Single Decision That Ends Stock Market Obsession

 A few weeks back, I sat down to write my IPS. In the world of finance, that stands for Investment Policy Statement.

Think of it as a “Business Plan” for your money. It’s a formal document that outlines the rules of the game for your portfolio. Its purpose is to hold your hand during times of severe market volatility. When the crap is hitting the fan, you read it to remind yourself why you invest the way you do. It can even advise you on what to buy during a downturn.

Think of it as a blueprint for the thermal exhaust port map on your Death Star. It outlines the specific weaknesses you are trying to protect. The goal is to ensure one lucky shot from an emotional impulse doesn’t blow the whole thing up.

Since I don’t use a financial advisor (I can hear a few of you screaming at me already), the IPS is my only anchor. I struggle mightily to have faith that the market always goes “up and to the right.” The “Lost Decade” of the early 2000s scarred me deeply. Retiring into a market like that scares the absolute bejesus out of me.

An advisor would just tell me what I already know I should do. 60/40. 50/50. Bucket approach. Pick one.

They would be there to help talk me off a ledge, sure. But at the end of the day, it’s still my decision. Paying someone to move the pieces is no different than me doing it myself—I still have to sign on the dotted line.

I need a psychiatrist, not an investment advisor. The Dark Side is strong in this one.

I digress.

Why the IPS?

Without an IPS, Vader is a dangerously emotional investor on both the up and the down. When the market dips, the Dark Side whispers “Panic Sell.” When a trendy tech stock rips, it whispers “Performance Chasing.” The IPS is supposed to be my Jedi Code, my anchor—ensuring every decision aligns with long-term goals rather than short-term impulses.

But writing it? That was easy. But I struggle to stick to it.

The goal is easy: 5% return, tax-advantaged. Done. Simple. My nature is to Protect the Precious (the nest egg). We don’t need to conquer the galaxy; Padme’s some day pension means a 4% to 5% return is all we need to retire. Why risk the fleet chasing larger returns? Why keep playing the game if you have already won.

But I have a hard time with that goal because of:

The FOMO Menace

But then… the market goes on a huge tear. ( FOMO = Fear of Missing Out)

• 2020: +18.4% (during a pandemic?!)
• 2021: +28.7%
• 2022: -18%
• 2023: +26%
• 2024: +25%

I made my 4% or 5% each year. I technically hit my goal over the last five years. But I’m looking at a 27% personal gain vs. a market benchmark of nearly 100%.

Holy $%#^. (Insert many more colorful, non-Jedi words here).

FOMO hits, and it hits hard. When I see those numbers, I want to forget my conservative nature and put it all on black. Or Nvidia. Or Tesla—the stock I love to hate, but one that is still way, way up on a five-year chart.

Vader = Idiot. Just. Get. In. More. In Anything. Bonus points if it’s the index.

The News is a Trap

My attitude over the last seven years has been “Protect the Precious” instead of “Grow the Empire.” If I had just let go of the fear, the “Precious” would be PRECIOUS by now.

But the news sways me. If you read investing clickbait every day, Doom is always just around the corner. It started for me in 2017 with the volatility of the US election. The talking heads promised a collapse, I couldn’t ride through it, and my returns suffered. Don’t always believe what you hear.

Now, the doom-meter is cranked past 11. AI bubbles, Software stocks collapsing, layoff due to AI coming soon, tariff hell, global wars, no Valentine’s Day present—there is always a Death Star on the horizon.

I cut my investment “teeth” in the 2000 bubble. I watched the money disappear and realized the S&P didn’t surpass that peak until 2014. Fourteen years. That’s the “Nuclear Winter” I’m trying to protect against as I approach retirement. It’s likely stupid. The odds are 99.9% against it. But I treat it like roulette, fearing that one event that sinks us for a decade.

As the market approaches new highs, I freeze. I know it’s always at new highs because it’s always going up, but when it goes down, buying the dip isn’t any easier.

I think I’m okay being a conservative investor until FOMO takes over. The emotional side—the Dark Side—is angry and itching to jump in just as we touch these peaks. But the Dark Side is fueled more by fear than anger. In this case, I actually need the anger to win so I’ll finally invest more aggressively. To make my IPS more aggressive.

I need to figure out the portion I don’t need for five years, close my eyes, and just put it in the market. If I had just done that any time in the last five years, I’d be miles ahead. Just Dollar Cost Average. Pick six months, hell, pick a year, and just spread it out.

So, do I chase the returns or stick to my nice, boring 5%? My brain says the 5% is fine, but man, my emotions want to party with everyone else.

The stopped clock waits. 4 to 5% it is. Now, where is that IPS? Maybe if I pair it with an IPA or two, I can finally get through this.

The S&P for the first time in a while has a been almost flat for a month or two. As usual it feels weird.

All downhill from here? Or is it?