Dre Griggs, Investment Advisor Representative with Obsidian Wisdom

Dre Griggs, Investment Advisor Representative with Obsidian Wisdom Wondering if your retirement strategy is truly tax-smart? Take the Tax-Smart Retirement Stage Assessment at https://obsidianwisdom.com/assessment

06/24/2026

Your third bucket is your later bucket.

This is where we focus on growth.

If we're going to focus on growth, we need to have eight plus years before we actually need to touch that money.

Historically speaking, every decade there's like one recession.

That means eight or nine years are growth.

We don't want to be so conservative that we're missing eight years of growth.

But we also need to protect ourselves from the recession years because those can significantly impact success in retirement.

This bucket is where we focus on equities.

Real estate.

Your own personal business.

Even commodities for those who like gold or crypto.

In a normal environment, we spend from the cash bucket.

At the end of the year, we look at how the portfolios are doing.

If bucket number three is doing well, we sell and replenish bucket number two.

And replenish bucket number one.

That's the process.

That's the plan.

06/23/2026

Let me show you two retirees.

The first retiree has one giant blender portfolio.

The market crashes.

Income is needed.

Stocks get sold.

Stress increases.

Fear increases.

The second retiree has a bucket strategy.

Two years of spending already set aside.

Not worried about the recession.

A refill process already established.

A plan already written.

When the market crashes, spending continues uninterrupted.

No panic.

No guessing.

No emotional decisions.

The difference is preparation.

The bucket strategy does not guarantee higher returns.

It does something much more important.

It creates a system designed to prevent bad decisions during bad markets.

Because retirement is not about predicting the future.

It is about preparing for multiple versions of the future.

06/19/2026

Let's say you retire with $1,000,000.

The market declines.

Your $1,000,000 falls to $830,000.

You cross the lower guardrail.

The rule says you reduce your spending by about 10%.

So your spending drops from $50,000 to $45,000.

That's it.

No panic.

No emotions.

No freezing in place.

The decision was already made ahead of time.

Now let's look at the other side.

The market crushes it.

Your withdrawal rate falls well below your original 5%.

Maybe it drops to 3%.

Now you've crossed the upper guardrail.

The rule says give yourself a raise.

Often around 10%.

The same discipline that told you to spend less during bad times now gives you permission to spend more during good times.

Most retirees never talk about this side.

Many retirees underspend out of fear and sacrifice quality of life.

The best part?

Most years require no adjustments at all.

The guardrails only activate when your portfolio drifts too far from the original plan.

The goal is simple.

Stay right between the lines.

06/18/2026

Let me show you the bigger picture.

The bucket strategy is my favorite withdrawal strategy.

It answers one question.

Where does this year's spending come from?

The cash bucket.

The income bucket.

Or the growth bucket.

The guardrail strategy answers a different question.

How much can I actually spend this year?

When you put them together, they solve two different retirement problems.

One solves portfolio management.

The other solves spending management.

But the real value of guardrails is not the math.

It's the psychology.

Retirement is full of uncertainty.

The market is uncertain.

Inflation is uncertain.

The government is uncertain.

Healthcare costs are uncertain.

But your response does not have to be.

The retirees who feel the most freedom are not the ones who predict the future.

They are the ones who build a plan for multiple futures ahead of time.

You do not need a crystal ball.

You need a process.

Because when the market throws you a curveball, the plan has already decided what happens next.

That is where confidence comes from.

06/09/2026

When I think about inflation, I ask a simple question.

What goes up in cost with inflation?

Real estate.

If I charged you rent, that goes up with inflation.

The value of my property goes up if I want to sell it, and the rent I can charge goes up because of inflation.

The stock market goes up with inflation.

If your investments grew by 3% but that was all inflation, then you didn't really get a gain.

You just maintained your exact same lifestyle.

And then there's your own personal business.

Some businesses can raise their prices.

Apple can raise prices.

Jordan's can raise prices.

Other businesses sell commodities.

If I sold oranges, there's not much I can do to differentiate my oranges.

They're orange, they're sweet, and they're round.

If you're investing in assets like these, you're not worried about inflation.

06/02/2026

The way I think about spending money is like playing Monopoly.

When I'm playing Monopoly, my goal is to get as many income producing assets as I possibly can.

If I land on a railroad, I'm buying it.

If I land on a property, I'm buying it.

If I land on free parking, I'm upset because I wasted my turn.

Passing Go and collecting $200 is our time for our money.

That's our paycheck.

But if we don't buy assets that start generating more money than the time it takes us to go around the board, you will lose in Monopoly.

No matter how much money you have.

No matter how lucky you've been.

The only way to win is to have something generating money for you that is quicker than you going around the board with your time.

That's how Monopoly works.

And that's how I think about retirement.

06/02/2026

I find that maybe our lifestyle is relatively expensive because we have a bunch of debt.

We are conditioned to get the job and then get the house to celebrate the fact that we got the job.

Then you get the car because you've been struggling, you've been trying to make it, and you finally made it.

But now we've built a lifestyle that requires us to keep working.

If you didn't have the debt and you were able to allocate more of your money towards your freedom fund and your separation of your time from your money, we would feel much different.

A lot of us are spending our money that is to purchase our freedom on semblances of freedom.

Things that make us feel like we're free.

But we're actually indebting ourselves to the system for another two years, another three years, another five years.

06/01/2026

When I use the word retirement, most people are like, "No, I'm not gonna retire for at least 10, 15, maybe 20 years. Dude, I got plenty of time."

But if retirement is separating your time from your money, what age do you think it's important to separate your time from your money?

You'd probably say, "As soon as possible."

You don't have to stop working.

You just don't have to work for money.

When wisdom equals freedom, now I work and volunteer and I travel and I do all the things I've always wanted to do.

Now all that time is mine.

That's freedom.

That's what the game is about.

That's what we're playing for.

And we're playing to win.

06/01/2026

I meet people all the time who are investing like they are 35.

But they are actually retiring in 10 or 15 months.

And that always leads to the same question.

How do we feel about the risk?

Because there are a handful of reasons people run out of money in retirement.

Some people are not invested aggressively enough.

So they are not outpacing inflation.

Some people are not planning for healthcare costs.

Some people outlive their money.

Some people pay too much in taxes.

And some become too dependent on Social Security.

The challenge is finding the balance.

Too much risk creates one problem.

Not enough risk creates another.

Think about a carton of eggs.

In 2001, a carton of eggs cost about $1.

Today, that same carton of eggs may cost $5 to $10.

If your retirement plan was built around $1 eggs.

How do you afford $5 to $10 eggs twenty years later?

That is why inflation matters.

That is why risk matters.

And that is why your retirement plan needs to address more than just investment returns.

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