Betting on Red vs. Planning for Real Life: Why Retirement Money Deserves a Smarter Strategy

I talk to clients all the time about diversification.

And a lot of times, the response sounds something like this:

“Well, I got in and out of Bitcoin at just the right time.”

“I took a loan from my 457(b) during 2020 and invested it elsewhere - and I definitely made more money.”

And honestly? Sometimes that’s true.

But hindsight has a funny way of making us all feel like financial geniuses.

When things work out, we look back and think:

“Wow. I’ve got great instincts.”

“I knew something other people didn’t.”

“I really have this dialed in.”

But the flip side is also true.

Sometimes we look back and say:

“I knew that was going to happen and I didn’t act.”

Or worse:

"Every time I decide something, it’s the wrong choice - even when I do the opposite of what I was going to do.”

The truth is pretty simple (and humbling):

Sometimes we get it right. Sometimes we don’t.

Skill, Instinct… or Just Timing?

Now, to be fair - sometimes people are more educated.

Sometimes they do have better instincts.

Sometimes experience really does teach you which way to lean.

And sometimes?

It’s just timing. Plain and simple.

That’s why I’m very honest with my clients:

I am not a stock picker.

I might get it right.

I might get it wrong.

And because of that, I don’t like to put all my eggs in one basket.

As legendary investor Peter Lynch once said:

“Far more money has been lost by investors trying to anticipate corrections than lost in the corrections themselves.”

In other words, trying to be perfect usually costs more than being patient.

Retirement Money Is Not “Bet It All on Red”

I’m in this - and most of you should be too - for the long haul.

This is retirement money we’re talking about.

Not weekend gambling money.

Not “let’s see what happens” money.

The phrase “bet it all on red” might work at a roulette table, but it does not belong anywhere near your retirement plan.

That’s why my focus isn’t just on helping you save and invest for retirement - it’s also about how and where you take money from when you’re retired.

Because building the pile is only half the story.

Distributing it wisely - tax-efficiently, sustainably, and in the right order - is what makes that money actually work for you.

One Plan, Built for You

With your work plans and long-term savings, my goal is to help you build the most balanced plan for YOU - your goals, your timeline, your comfort level, your life.

That plan might include:

• Roth funds

• Pre-tax funds

• 529 plans

• Annuities

• Brokerage accounts with ETFs and mutual funds

• Life insurance

• Long-term care planning

• Power of attorney documents

• Wills and trusts

Not because you need everything - but because you need the right combination, and that combination looks different for everyone.

One Size Fits No One

I fully support talking with friends, coworkers, family members, and neighbors about money. Those conversations can be helpful.

But please don’t base what you do on what they are doing.

It’s a lot like medical advice.

Just because your neighbor had a certain diagnosis doesn’t mean you do.

But it does mean you might know what questions to ask your doctor.

Same with finances.

Other people’s experiences can help you ask better questions - but if something doesn’t fit your situation, don’t force it.

Appearances Can Be Deceiving

One last thing - and this one matters.

That person who looks incredibly financially stable?

The one you quietly envy?

They might be financed to the hilt.

Big house. New cars. Nice vacations.

And a mountain of debt behind the scenes.

You don’t know the whole story - and neither does Instagram.

Final Thought

Good planning isn’t about being right all the time.

It’s about building a strategy that can handle being wrong sometimes - and still get you where you want to go.

Your Next Step

Ask yourself this:

“If my best guess turns out to be wrong, does my plan still work?”

If the answer is no, that’s not a failure - it’s just a sign that it might be time to revisit your balance, your risk, and your long-term strategy.

If you’d like help with that, I’d love to sit down with you.

We can talk through where you are, where you want to go, and how to build a plan that not only gets you to retirement - but helps you use your money wisely once you’re there.

Real planning isn’t about perfect timing.

It’s about thoughtful decisions, made together, over time.