Time in the Market, Not Timing the Market

Monthly Money Man on April 17, 2026

One of the biggest mistakes I saw people make wasn’t about what they invested in. It was about when they started.

They’d wait for the “right time.” Wait for the market to drop. Wait until they understood everything. Wait until they had more money saved up.

And while they waited, years passed. And those years cost them more than any market timing strategy ever could have made them.

The Math That Changes Everything

Let me show you two people. Same income. Same investing goals. Different start dates.

Person A starts investing at age 22. Puts away $300 a month for 10 years, then stops completely at age 32. Never adds another dollar.

Person B waits until age 32 to start. Invests $300 a month for 30 years straight until retirement at 62.

Who ends up with more money at 62?

Person A: $1,072,000
Person B: $678,000

Person A invested for 10 years. Person B invested for 30 years. Person A put in $36,000 total. Person B put in $108,000 total.

Person A still wins. By nearly $400,000.

That’s the power of time in the market. (Assuming 10% average annual returns, which is the historical average for the S&P 500.)

Why This Happens: Compound Interest

Albert Einstein supposedly called compound interest “the eighth wonder of the world.” Whether he actually said it or not, the principle is real.

Your money doesn’t just grow. It grows on the growth. And then it grows on that growth. And then it grows on that growth.

The longer your money sits in the market, the more times it compounds. Early years are worth more than later years because they have more time to multiply.

That $300 Person A invested at age 22? It had 40 years to compound. The $300 Person B invested at age 32? Only 30 years.

Ten years doesn’t sound like much. But over decades, it’s the difference between over a million dollars and $678,000.

Time In the Market vs Timing the Market

Here’s what people try to do: wait for the market to drop, then invest when it’s “cheap.”

The problem? Nobody knows when that’s going to be.

I watched people sit on cash in 2013 waiting for a correction. The market kept climbing. They finally bought in 2015 after missing two years of gains.

I watched people panic-sell in March 2020 when COVID hit. The market recovered in months. They missed it.

I watched people wait for the “right moment” for years. The right moment never came. Or it came and they didn’t recognize it.

The data backs this up: A study by Charles Schwab compared different investing strategies over time. They looked at someone who invested at the absolute perfect time every year (the market bottom), someone who invested at the worst time every year (the market peak), and someone who just invested consistently regardless of timing.

The difference in returns after 20 years? Almost nothing.

The person who timed it perfectly beat the person who just invested consistently by less than 1% annually. But the person who waited on the sidelines trying to time it? They lost decades of growth.

Completion Not Perfection

I used to tell clients: completion not perfection. You don’t need to understand everything before you begin. You don’t need a PhD in finance. You don’t need to read every investing book ever written.

You need to understand enough to not make catastrophic mistakes, then start.

Here’s “enough”:

  • Know which account to use (we covered this last week)
  • Know what to buy (we’re covering this in two weeks – spoiler: index funds)
  • Know you’re investing for decades, not days
  • Know you’ll keep adding money regularly

That’s it. Start with that. You’ll learn the rest as you go.

The “But What If…” Questions

“What if the market crashes right after I invest?”

It might. It probably will at some point. Doesn’t matter. You’re not pulling the money out for 30 years. It’ll recover. It always has.

“What if I’m buying at the peak?”

Maybe you are. Or maybe this “peak” will look like a valley ten years from now. Nobody knows. That’s why you invest consistently over time instead of trying to nail the perfect entry point.

“What if I wait and invest more later?”

You just saw the math. Person B invested 3 times more than Person A and still ended up with almost $400,000 less. Waiting costs you more than you think.

The Best Time Was Yesterday

There’s an old saying: “The best time to plant a tree was 20 years ago. The second best time is today.”

Same goes for investing.

If you’re in your early 20s and reading this, you have the most valuable asset in investing: time. Use it.

If you’re 35, 45, or 55 and reading this, you’ve lost some time. You can’t get it back. But you still have years ahead of you. Don’t waste those too.

Here’s what I learned over the years: completion not perfection. Starting with good enough beats waiting for perfect every single time.

The biggest mistake isn’t starting at 32 instead of 22. The biggest mistake is being 42 and wishing you’d started at 32.

Your Action Step This Week

If you already have your investment accounts open: Make your first contribution this week. Even if it’s just $50. Get the account funded and pick what to invest in (we’ll cover what to buy in a couple weeks).

If you don’t have accounts yet: Go back and read last week’s article. Open a Roth IRA. It takes 15 minutes.

Don’t wait for perfect. Perfect doesn’t exist. Start now. Let time do the heavy lifting.

See you at the top.

Are You Ready to Start Investing?

Monthly Money Man on April 3, 2026

One of the most common questions I got as a financial advisor: “Should I start investing?”

My answer was always the same: “Show me your foundation first.”

I’d sit across from people who’d read about tax-free growth and compound interest. They were fired up and ready to open a Roth IRA or start buying index funds. But when I asked about their foundation—emergency fund, employer match, high-interest debt—the pattern was almost always the same.

No emergency fund. Leaving employer match on the table. Carrying credit card debt at 20%+.

They weren’t ready to invest yet. Not because they were doing something wrong, but because the foundation wasn’t there. And without the foundation, investing is just building on sand.

The Foundation Comes First

Before you put a single dollar into the market, you need three things in place:

First: Safety Net #1
 One month of expenses sitting in a savings account. Not invested. Cash.

This is your buffer against life. Car breaks down? Water heater dies? Unexpected medical bill? You handle it without going into debt or selling investments at the worst possible time.

Without this, the first emergency forces you to either take on high-interest debt or liquidate your investments—probably when the market is down.

Second: Employer match (if you have one)
 If your employer offers a 401k match of 50% or more, contribute enough to get the full match. That’s free money with an immediate guaranteed return you can’t get anywhere else.

This is the only exception to “build your cash reserve first.” Get the match, then finish building your emergency fund.

Third: High-interest debt under control
 Anything above 10% gets paid down before you start investing beyond the employer match.

Here’s why: if you’re paying 20% on credit card debt while trying to earn 8% in the market, you’re going backwards. You can’t invest your way out of high-interest debt. The math doesn’t work.

Why the Order Matters

I’ve seen people do this backwards. They start investing while sitting on $15,000 in credit card debt at 22% interest.

They feel like they’re “getting ahead” because they’re investing. But they’re actually losing ground every single month. The interest on their debt is growing faster than their investments.

Or they invest without an emergency fund, then something breaks, and they have to sell their investments to cover it. Now they’ve locked in losses and reset their investment timeline.

The foundation isn’t optional. It’s what makes investing actually work.

When You’re Actually Ready

You’re ready to start investing when you can check all three boxes:

✓ One month of expenses in cash
✓ Getting your full employer match (if available)
✓ No debt above 10% interest

If you can’t check all three, you’re not ready yet. And that’s okay.

Build the foundation first. It’s not as exciting as watching your investment account grow, but it’s what makes the growth sustainable.

What “Not Ready” Looks Like

If you’re not ready to invest yet, here’s what you should be doing instead:

Focus on Safety Net #1. Every dollar you were thinking about investing goes into your savings account until you hit one month of expenses. Use the pay yourself first system we talked about in March.

Get your employer match. Even if you’re still building your emergency fund, contribute enough to get that free money. Don’t leave it on the table.

Attack high-interest debt. If you’re carrying balances above 10%, that’s your investment right now. Paying down 20% debt is a guaranteed 20% return.

This isn’t glamorous. It doesn’t have the appeal of “I’m an investor now.” But it’s what actually works.

The Reality Check

Most people want to skip straight to investing because that’s where the exciting stuff happens. Compound interest, tax-free growth, building wealth—I get it.

But investing without the foundation is like trying to summit a mountain without the right gear. You might make it partway up. But the first storm hits and you’re in trouble.

The foundation is your gear. Build it first. Then climb.

Your Action Step This Week

Pull out a piece of paper and write down:

  1. Do I have one month of expenses in savings? Yes or no.
  2. Am I getting my full employer match? Yes, no, or N/A.
  3. Is all my debt below 10% interest? Yes or no.

If you got three yeses (or two yeses and an N/A), you’re ready. Next week, we start talking about where to actually invest and why time in the market beats timing.

If you got any nos, you’re not ready yet. And that’s fine. You know what to work on first.

See you at the top.

The 10% Line: When Debt Becomes a Problem

Monthly Money Man on March 27, 2026

I’ve sat across from more people with high-interest credit card debt than I can count. Medical professionals, teachers, engineers—high earners who felt broke every month and couldn’t figure out why.

The pattern was always the same: decent income, reasonable expenses, and thousands of dollars vanishing every month in credit card interest.

One pattern I saw over and over: someone carrying $15,000 to $20,000 in credit card debt at 20%+ interest rates. That’s $3,000 to $4,000 a year—gone. Not reducing the balance. Just interest.

That’s the 10% problem.

Why 10% Is the Line

Interest rates above 10% aren’t just expensive. They’re actively draining your monthly money before you even get a chance to use it.

A mortgage at 6%? That’s financing an appreciating asset. A car loan at 5%? You’re paying for transportation you need. Those rates are manageable.

But credit cards at 18%? Department store cards at 24%? Personal loans at 15%? That’s not financing. That’s bleeding.

Here’s the math that matters: if you’re carrying $10,000 at 20% interest, you’re paying $2,000 a year just to keep that debt. That’s $167 every month that doesn’t reduce your balance, doesn’t build equity, doesn’t do anything except disappear.

You can’t save your way out of that. You can’t invest your way past it. You have to stop the bleeding first.

The Hidden Cost

The real problem isn’t just the money you’re paying in interest. It’s what that money could be doing instead.

Someone paying $300 a month in credit card interest? If they redirected that money to a Roth IRA instead—at 8% average annual returns—they’d build $180,000 over 25 years.

But they can’t. Because the interest payments come first. Every single month.

This is why I tell people: high-interest debt gets fixed before almost anything else. You get your employer match in your 401k (that’s free money you can’t recapture). Then you attack this debt. Aggressively.

How to Know If You Have the 10% Problem

Pull out your credit card statements right now. Look at the interest rate. It’s printed right there on every statement.

If it says anything above 10%, you have the problem.

Don’t look at the minimum payment and think you’re okay. That minimum payment is designed to keep you in debt for decades. Look at the interest rate.

Common culprits:

  • Credit cards: 15% to 29%
  • Department store cards: 20% to 27%
  • Personal loans: 10% to 18%
  • Payday loans: don’t even get me started (often 300%+)

What This Looks Like in Real Life

Let’s say you have $5,000 on a credit card at 18% interest. Minimum payment is $125 a month.

If you only pay the minimum, it’ll take you 23 years to pay it off. You’ll pay $4,300 in interest. Almost as much as you originally borrowed.

But if you threw an extra $100 a month at it—$225 total—you’d pay it off in 2 years and pay only $900 in interest.

That’s the difference between bleeding slowly for two decades and fixing the problem fast.

The Fix

I’m not going to tell you to cut up your credit cards and live on cash. That’s not my style.

What I am going to tell you: this debt gets priority.

In August, we’re going to dive deep into avalanche vs snowball methods, balance transfer strategies, and exactly how to attack this systematically. We’ll use the debt payoff calculator I built for you. We’ll map out your complete plan.

But right now, today, you need to know where you stand.

Add up every debt you have with an interest rate above 10%. Write down the total. That’s your number.

That number represents money leaving your life every month that could be building your future instead. It’s like carrying a water bottle with a slow leak—you’re losing resources drop by drop on every climb, and by the time you notice, half of what you needed is already gone.

We’re going to deal with it. But first, you have to see it clearly.

What You Can Do Right Now

I’m not going to give you the full debt payoff strategy here—that’s coming in August with detailed methods and the calculator. But if you have high-interest debt, you can’t afford to wait five months doing nothing.

Three things to do this week:

First: Stop adding to it. If you’re still using the cards that are charging you 20%+, you’re pouring water into a leaking bucket. Put them away.

Second: Pay more than the minimum. Even an extra $50 or $100 a month makes a massive difference. On that $5,000 example I showed you? An extra $100 cuts your payoff time from 23 years to 2 years.

Third: Call your credit card company and ask for a lower rate. Seriously. Just call and say “I’ve been a customer for X years, I’d like a lower interest rate.” It doesn’t always work, but when it does, you just saved yourself real money with a 5-minute phone call.

We’ll get into balance transfers, refinancing strategies, and the complete battle plan in August. But don’t wait to stop the bleeding.

Your Action Step This Week

Pull your credit card statements. All of them. Look at the interest rates. Add up the balances on anything above 10%.

That’s your 10% problem.

Write it down. We’ll come back to it in August with a complete battle plan.

See you at the top.

Pay Yourself First: How to Build Wealth on Autopilot

Monthly Money Man on March 20, 2026

When I was managing money for clients, I saw a pattern that repeated itself over and over again.

The people who built real wealth weren’t necessarily the ones making the most money. They were the ones who had set up systems that worked automatically, without requiring daily willpower or discipline.

The most powerful system? Pay yourself first.

You’ve probably heard this phrase before. Maybe you’ve even tried it. But here’s what I learned watching hundreds of people succeed (and fail) at this: it’s not about intention. It’s about mechanics.

What “Pay Yourself First” Actually Means

It’s simple: before your paycheck hits your checking account and becomes “available” to spend, a portion of it goes somewhere else. To savings. To investments. To your future self.

Not what’s left over at the end of the month. Not “if there’s extra.” First.

I remember sitting with a couple in their early 30s. They made good money—combined household income over $120,000. But every month, they felt broke. Every single month.

“We just don’t know where it goes,” they told me.

I asked them to show me their savings rate. Zero. Because they were trying to save what was left over. And there’s never anything left over when you do it that way.

The Psychology Behind Why This Works

Here’s the truth about human behavior and money: we spend what we see.

If you have $3,000 in your checking account, you’ll find a way to spend closer to $3,000. If you have $2,400 in your checking account, you’ll find a way to live on $2,400.

The difference? That $600 that never showed up in checking went straight to savings the day your paycheck deposited.

This isn’t about deprivation. It’s about making the right choice the easy choice. You’re not fighting yourself every month trying to be disciplined. You made the choice once, set up the system, and now it runs on autopilot.

How to Set Up the System

Step 1: Decide on a percentage

Start with 10% if you’re new to this. Already saving? Push it to 15% or 20%. The exact number matters less than the fact that it’s automatic and consistent.

Step 2: Split your direct deposit

Many payroll systems let you split your direct deposit between multiple accounts—check with your HR department to see if yours does. This is the absolute best way to do it.

  • Option A: Have your employer deposit 10% directly into your savings account and 90% into checking
  • Option B: If your employer doesn’t allow splits, set up an automatic transfer on payday from checking to savings

Step 3: Make it immediate

The transfer should happen the same day you get paid—or before you even see the money. If you wait until the 15th of the month to manually move money around, you’ve already spent it in your head.

Step 4: Treat it like a bill

That 10% (or 15%, or 20%) isn’t optional. It’s not negotiable. It’s the first bill you pay every month. The bill is to your future self.

Where the Money Should Go

This depends on where you are in your financial journey. Use this priority order:

First priority: Build your Safety Net #1—one month of expenses in cash. Until you have this, every dollar you’re paying yourself first goes here.

Second priority: Get your employer match in your 401k or 403b (if it’s 50% or higher). This is the only time I’ll tell you to invest before paying off high-interest debt. Here’s why: if your employer matches 50 cents on every dollar you contribute, that’s an instant 50% return. You can’t get that anywhere else. You also can’t go back in time and claim matches you missed.

Even if you’re carrying credit card debt at 18%, you need to contribute enough to get that full match. Yes, you’re still paying interest on your debt. But you’re also getting free money that will compound for decades. We’ll talk more about balance transfers and refinancing strategies in August—there are ways to lower that interest rate on your debt. But there’s no way to recapture an employer match you let slip away.

Plus, getting that match forces you to learn to live on what’s left. That’s the system working.

Third priority: Pay off high-interest debt (anything over 10%). If you’re carrying credit card debt at 18% or 24%, paying that down is paying yourself first. You’re getting an immediate 18% return. In August, we’ll dive deep into avalanche vs snowball methods and strategies for tackling this.

Fourth priority: Max out your Roth IRA. Once you’ve got your cash reserve built and you’re getting your employer match, this is your next move. We’ll cover Roth IRAs in detail in April and May, but the short version: tax-free growth for the rest of your life. If you got a tax refund and you’ve checked the first two boxes, this is where that money should go.

Fifth priority: Go back to your 401k and increase your contribution beyond the match. Push toward 15% total retirement savings.

What If You Can’t Afford 10%?

Start with 5%. Or 3%. Or even 1%.

The amount is less important than the system. Get the mechanics in place now. A year from now when you get a raise, increase it to 6%. Then 8%. Then 10%.

I’ve seen people go from saving nothing to saving 20% of their income. It didn’t happen overnight. It happened by setting up the system and then adjusting the percentage every time their income increased.

The Backpack Check

Think of this as one of the most important items you’re carrying in your financial backpack: the habit of paying yourself first.

It’s not heavy. It doesn’t require daily attention. But it’s the difference between arriving at the summit with resources—or arriving exhausted and empty-handed.

Set it up once. Let it run. Watch what happens over the next five years.

Action step for this week: Log into your bank or payroll system today. Set up that automatic transfer. Even if it’s just 5% to start. Make the decision once so you don’t have to make it every month.

See you at the top.

Your Tax Refund: Freedom or Consumption?

Monthly Money Man on March 13, 2026

The Bottom Line Up Front: That refund hitting your bank account isn’t a windfall. It’s your own money coming back to you. And what you do with it in the next 72 hours will tell you everything about whether you’re still the old financial you, or the new one climbing toward the summit.

Let me guess what’s happening right now.

You filed your taxes. You’re getting a refund. And you’re already thinking about what to buy with it.

Maybe it’s that thing you’ve been eyeing for months. Maybe it’s a weekend trip. Maybe it’s just “treating yourself” because you feel like you earned it.

I’m not here to judge. But I am here to ask you one question:

Are you buying freedom, or are you consuming?

Because here’s the truth most people don’t want to hear: your tax refund isn’t bonus money. It’s not a gift from the government. It’s money you overpaid all year that’s finally coming back to where it belonged all along—in your hands.

And what you do with it in the next few days will show you exactly who you are financially.

The Consumption Trap

I’ve watched this pattern play out hundreds of times.

Someone gets a $2,000 refund. They’re excited. They feel like they just won something.

And within two weeks, it’s gone.

New TV. Night out. Online shopping spree. Upgrade the phone. Book a flight.

All consumption. Nothing invested in the climb ahead.

And here’s what happens next: three months later, that same person is stressed about money again. The emergency fund is still empty. The debt is still there. The financial anxiety is still crushing them.

Because they consumed the refund instead of using it to buy freedom.

What It Means to Buy Freedom

Freedom isn’t a vacation. Freedom isn’t a new purchase.

Freedom is waking up and knowing you have options.

It’s having one month of cash reserves so you’re not living paycheck to paycheck anymore.

It’s paying off that credit card so you stop hemorrhaging interest every month.

It’s maxing out your Roth IRA contribution so your future self doesn’t have to scramble.

Freedom is what you buy when you use money to reduce stress instead of create temporary pleasure.

And your tax refund—if you’re getting one—is the single best opportunity you’ll have all year to buy a significant amount of freedom all at once.

The Test of Who You’re Becoming

Last week we talked about emptying your financial backpack to see what you’ve been carrying.

This week, you’re making a choice about what to put back in.

The old financial you puts consumption back in. Stuff. Experiences that don’t build anything. Short-term pleasure that disappears.

The new financial you—the one who’s ascending this mountain—puts tools back in. Things that make the climb easier. Things that reduce the weight you’re carrying.

Your refund is the test.

Are you still the person who consumes windfalls? Or are you becoming the person who deploys them strategically?

Where Your Refund Should Actually Go

Here’s the honest answer: I don’t know where your refund should go.

Because I don’t know what your greatest financial weakness is right now.

But you do.

If you have no emergency fund: Your refund just became the foundation of your safety net. Put every dollar toward building that first month of cash reserves. That’s buying freedom from paycheck-to-paycheck panic.

If you’re carrying high-interest debt: Your refund just became a debt destroyer. Attack the highest-interest debt first. Every dollar you put there is buying freedom from interest payments draining your account every month.

If your foundation is solid but you’re not investing: Your refund just became your future. Max out your Roth IRA contribution for the year. That’s buying freedom for future you.

If you’re already doing all of those things: Then yes, enjoy some of it. But even then, consider using most of it to accelerate your climb. Freedom compounds. Consumption doesn’t.

The answer isn’t the same for everyone. But the question is: where do you need freedom most?

What to Do Right Now

If you’re expecting a refund, here’s your action step before it even hits your account:

Decide where it’s going before you have it.

Not “I’ll figure it out when I get it.”

Not “I’ll see how I feel.”

Right now. Today. Decide.

  • Is it going to your emergency fund?
  • Is it going to debt?
  • Is it going to your Roth IRA?
  • Is it going to finally fix that financial weakness you’ve been avoiding?

Write it down. Make the decision now, while you’re thinking clearly, before the money is sitting there tempting you.

Because once it hits your account, the consumption voice gets louder. The rationalizations start. The “just this once” thoughts creep in.

Make the decision now. Lock it in.

The New Financial You

You’re not the same person you were in January.

You’ve been tracking your spending. You’ve been building your safety net. You’ve been emptying your financial backpack and examining what you’re carrying.

You’re becoming someone different. Someone who’s climbing.

Your tax refund is the moment you prove it.

The old you would have already spent it in your mind.

The new you is buying freedom.

Which one are you?

See you at the top.

What’s in Your Financial Backpack? Start With Taxes

Monthly Money Man on March 6, 2026

The Bottom Line Up Front: Every experienced hiker knows you can’t climb efficiently with a backpack full of unnecessary weight. Tax season is when you empty that pack, examine every single item you’ve been carrying, and decide what actually needs to come with you. Here’s what three days of tax season reminded me about financial organization and the weight most people don’t realize they’re carrying..

I’m sitting at my desk at 5am on a Friday, three days deep into tax preparation, and I’ve just finished my second cup of coffee.

Spreadsheets are open. Documents are scattered across my desk. My digital files look like someone detonated a bomb in a filing cabinet.

And as I sort through another year of financial activity, I’m reminded of something every serious hiker learns the hard way:

You have no idea how heavy your pack is until you empty it out and look at every single thing you’ve been carrying.

That’s exactly what tax season is. It’s the mandatory moment every year when you dump out your financial backpack, spread everything on the ground, and confront the reality of what you’ve been hauling up the mountain.

And for most people, that moment is sobering.

The Backpack You Didn’t Know You Were Carrying

Here’s what I’m finding as I go through my own taxes this week—the same patterns I saw working with hundreds of clients as a financial advisor:

People are carrying subscriptions they forgot existed. As I comb through my credit card statements for deductible expenses, I found one monthly subscription I’d forgotten about and a couple of annual subscriptions I no longer need. None of them feel heavy on their own. But add them up over a year? That’s weight you don’t need to carry.

People are carrying tax bills they could have avoided. I’m watching people around me scramble because they owe money they didn’t budget for. Not because they did anything wrong. But because they didn’t look in their backpack throughout the year to see what they were actually carrying.

Tax season doesn’t add weight to your pack. It just forces you to see the weight that was already there.

And more importantly, tax season is when you reorganize your financial backpack—deciding what stays, what goes, and how to pack it better for the climb ahead.

Why Tax Season Matters More Than You Think

I know most of you would rather do literally anything else than think about taxes right now.

I get it. I’m a former financial advisor, and I still hate this part.

But here’s the truth: tax season is the one time every year when you’re forced to see your complete financial picture.

Every dollar you earned. Every deduction you took or missed. Every account you have. Every financial decision you made for the past twelve months.

It’s all right there in front of you, whether you want to see it or not.

And that clarity—as uncomfortable as it is—shows you exactly what’s been weighing you down.

What I’m Learning From My Own Financial Backpack

Three days into this, here’s what sorting through my financial backpack is teaching me:

When you’re married, you’re climbing together—and filing together. This morning I was going through credit card statements looking for deductible expenses, and I found several charitable donations my wife made that weren’t in my donation folder. If I hadn’t been thorough with the credit card review, we would have missed claiming those deductions entirely. When you file jointly, you’re carrying one combined backpack. You need to know what’s in it from both sides.

Organization doesn’t mean the work is easy—it means the work is thorough. Yes, my donation receipts are in the right place. Yes, my accounts are organized. But matching receipts to credit card statements and verifying every deduction still takes real time and attention. There’s no five-minute shortcut to doing this right.

I’ve been carrying subscriptions I don’t need. That monthly subscription I forgot about and those couple of annual renewals I no longer use? That’s money leaving my account every month that could have been going toward my safety net instead. Tax season is when you catch these things.

Every single one of these things is weight I didn’t need to carry. And I only found them because tax season forced me to empty the pack.

The Questions You Need to Ask When Reviewing Your Financial Backpack

As you prepare your taxes this month—and you need to be preparing them, not avoiding them—here are the questions you should be asking:

What am I carrying that I don’t need?

Look at every subscription charge. Every account. Every recurring payment. If you’re not actively using it, why is it still in your pack?

I guarantee you’re paying for something right now that you forgot you had. Tax prep is when you find it.

What deductions am I missing?

If you’re itemizing, you need to comb through your credit card statements with a fine-tooth comb. Charitable donations. Business expenses. Medical costs. Property taxes.

The people who get the most deductions aren’t the ones who spend the most. They’re the ones who keep the receipts and do the work to claim what’s theirs.

Where are my documents actually going?

Do you have a system for tax documents, or are you scrambling every March to find things?

I’ve watched people waste hours looking for a single W-2 or 1099 that got buried in email. That’s weight. Set up a folder—digital or physical—and put everything there the moment it arrives.

Am I giving the government a free loan?

If you’re getting a big refund, congratulations—you overpaid all year. That’s your money the government has been holding interest-free.

Adjust your withholding. Take that money home in every paycheck instead and put it to work building your safety net, paying down debt, or investing. Don’t let it sit in the government’s backpack when it should be in yours.

Why do I want to look broke by December 31st?

Here’s advisor language most people don’t know: you want to maximize your deductions by year-end. Make charitable donations in December, not January. Max out your retirement contributions before the calendar flips. Prepay property taxes if it makes sense.

The government doesn’t care what you earn. They care what you earned minus what you can legally deduct. The lower that number, the less you carry in taxes.

The System You Need to Build Right Now

Here’s what I’m doing differently this year, and what you should do too:

Create a tax folder today. Every W-2, every 1099, every receipt, every statement goes in one place the moment you get it. No exceptions. No “I’ll file it later.”

Review your withholding if you’re getting a refund. Use the IRS withholding calculator. Adjust your W-4 with your employer. Get your money in your paycheck, not in April.

Track deductible expenses as they happen. Don’t wait until March to figure out what’s deductible. If you make a charitable donation, file the receipt immediately. If you have a business expense, categorize it the same day. And if you’re married, make sure you’re both putting receipts in the same place so nothing gets missed when you file jointly.

Set a reminder for December 15th. That’s when you review what you can do before year-end to reduce next year’s tax bill. Max out retirement contributions. Make charitable donations. Harvest tax losses if you’re investing.

You can’t fix December in April. But you can fix next December right now by building the system.

What This Has to Do With Your Financial Journey

You might be wondering why we’re talking about taxes when we’ve been focused on emergency funds.

Because you can’t climb efficiently with unnecessary weight in your pack.

And taxes—how you handle them, how you organize them, how much you overpay or underpay—are weight.

If you owe money in April you didn’t budget for, that’s weight that crushes your emergency fund progress.

If you’re getting a huge refund, that’s money that should have been building your safety net all year instead of sitting uselessly with the IRS.

If your financial life is so disorganized that tax season causes you three weeks of stress, that’s mental and emotional weight you’re hauling up the mountain.

Tax season is showing you what’s in your pack. What you do with that information determines how efficiently you climb.

Your Action Steps This Week

File your taxes properly and on time. No extensions unless absolutely necessary. Do it right, do it thoroughly, and get it done.

As you prepare, track three things:

  1. What surprised you (subscriptions, accounts, expenses you forgot)
  2. What you wish you’d tracked better throughout the year
  3. What weight you’re carrying that you don’t actually need

If you’re getting a refund: Adjust your withholding and redirect that money monthly.

If you owe money: Figure out why and set up quarterly estimated payments if needed.

Start your tax folder for next year today. Every document that arrives from here forward goes in one place. No exceptions.

Tax season isn’t punishment. It’s the moment you empty your financial backpack, see what you’ve been carrying, and decide what actually needs to come with you on the rest of the climb.

Most of it doesn’t.

See you at the top.

Fun Money — Allow Yourself to Breathe and Take in the View

Monthly Money Man on February 27, 2026

In January, we built our basecamp. We mapped out the year, set our financial intentions, and committed to the climb. In February, we focused on building our safety net — the cash reserves that catch us when life, as it always does, throws something unexpected in our path.

But here’s something every experienced climber knows that the guidebooks don’t always tell you. The mountain will break you if you never stop to breathe. If you put your head down and grind every single day without a moment to look up and take in the view, you won’t make it to the top. Not because the mountain beat you, but because you forgot why you started climbing in the first place.

That’s what this week is about. Fun Money.

Why Fun Money Is Not Optional

I want to be direct with you. Fun Money is not a reward for when you’ve “made it.” It’s not something you allow yourself after you’ve checked every financial box. Fun Money is a required line item in your budget — as essential as your rent, your groceries, and your emergency fund.

Here’s why. One of the most common reasons people abandon their financial climb isn’t because they lack discipline or intelligence. It’s because the journey feels like punishment. Every dollar is accounted for, every purchase is scrutinized, every impulse is denied. That works for about three weeks before human nature wins and the budget gets thrown out the window entirely.

The most successful financial plans I’ve ever seen — and after nearly three decades of living, studying, and advising on personal finance, I’ve seen a lot of them — are the ones that build enjoyment into the system from the beginning. Not as an afterthought. Not as a cheat day. As a planned, intentional, guilt-free category in the budget.

At Monthly Money, we’re not just about reaching the top. We’re about enjoying the climb. Because what’s the point of summiting a mountain you hated every step of?

Where This Idea Comes From

I’ll be honest with you about something personal. I grew up in a home where money was a constant source of tension. I watched my parents argue about finances more times than I can count, and eventually that financial stress contributed to their divorce. I was eleven years old when our family split apart, and I made a promise to myself that day — I would learn everything I could about money so I would never feel that powerless again.

But I also made a quieter promise. That when I built my own family, money would not be the thing that tore us apart.

My wife and I have been together for a long time, and I won’t pretend we’ve never had financial disagreements. Every couple does. But one of the systems that has genuinely protected our marriage — not just our budget — is Fun Money. We built it into our financial plan from the beginning, and it has diffused more potential arguments than I can count.

How the System Actually Works

Here’s the practical framework my wife and I use, and that I recommend as a starting point for any couple.

We set aside 3% of our combined net income — that’s take home pay after taxes — every single month. That 3% gets split in half. Half goes into her individual savings account. Half goes into mine. It happens automatically through a scheduled transfer so we never have to think about it or negotiate it in the moment.

That money is earmarked for one purpose only — to spend on whatever each of us finds meaningful, no questions asked and no justification required. If she wants to buy a piece of art for the living room or a pair of earrings I’d never understand the appeal of, that comes from her Fun Money. If I want to book a fly fishing trip or a river rafting adventure, that comes from mine. We don’t debate it. We don’t negotiate it. We simply say “it’s Fun Money” and move on.

I cannot overstate how many arguments that three word phrase has ended before they ever started.

Now, 3% is a baseline and a starting point — not a rule carved in stone. The best percentage is the one that two spouses can genuinely agree on and actually afford. If 3% of your net income works out to $100 a month, that’s $50 each. That might not sound like much, but here’s the beauty of the system — you don’t have to spend it every month.

I am a natural saver. There have been stretches of six months or more where I didn’t touch my Fun Money account at all, just letting it accumulate quietly while I focused on other things. And then one day I’d look at that balance and book something that genuinely filled my soul — a day of fly fishing in a mountain river, a challenging hiking expedition, an outdoor experience that reminded me why I work as hard as I do. I don’t place much value on material possessions. What I value is experience, adventure, and time in the wild. My Fun Money account makes that possible without a single dollar coming out of our family budget or a single conversation that starts with “do we really need to spend money on that?”

My wife has her version of that same freedom. And because we both have it, we’ve never had to fight over it.

Tony fly fishing in a mountain river enjoying his Fun Money outdoor adventure
This is my Fun Money in action — a trip to a mountain river that I saved up for month by month. Worth every penny.

What This Looks Like in Your Budget

If you’re single, Fun Money still belongs in your budget — it just looks a little different. It’s the category that gives you permission to spend on what brings you joy without derailing everything else you’re building. It’s the concert ticket, the weekend trip, the dinner out with friends that doesn’t send you into a guilt spiral afterward.

The Monthly Money Method is built around capturing the difference between what comes in and what goes out, then deploying that difference strategically. Fun Money is a strategic deployment. It’s not waste. It’s not weakness. It’s the investment you make in your own sustainability as a person who is playing a very long financial game.

The climbers who make it to the top are not the ones who never rest. They’re the ones who know when to rest, how long to rest, and how to use those moments to come back stronger for the next section of the climb.

Your Assignment This Month

Look at your current budget and find Fun Money. If it’s not there, add it. Start with 3% of your monthly net income and divide it equally if you have a spouse or partner. Set up an automatic transfer to a separate savings account on the same day every month — payday works well. Name the account something that makes you smile. And then give yourself genuine permission to spend it on whatever matters most to you, without guilt and without explanation.

The climb is long. The view along the way is part of the reward.

See you at the top.

Expect the Unexpected. Plan for the Unexpected.

Monthly Money Man on February 20, 2026

Last year, I was hiking in Oregon with my family. I was leading the group — map in hand, eyes down, mentally calculating how far we had left before we lost the light. I was so locked in on our destination that I stopped paying attention to where I was actually stepping.

Then I tripped over a rock. Nothing serious — a small cut on my knee, a bruised ego, and a lesson I won’t forget.

I was so focused on where we were going that I forgot to focus on where I was.

Your financial journey works exactly the same way.

The Trail Is Never Perfect

By now, you’ve done the math. You know what your safety net needs to look like. You’ve set your goals — maybe it’s one month of expenses, maybe you’re pushing toward three. That destination is clear.

But here’s what every experienced hiker knows and what every seasoned financial advisor has seen firsthand: the trail is never as clean as the map makes it look.

Something will break down. The car. The furnace. A appliance that quits on a Tuesday with no warning. Someone loses a job. A medical bill arrives that you didn’t see coming. These aren’t worst-case scenarios — they’re just life. The only thing unpredictable about the unexpected is the timing.

This is exactly why your cash reserve exists. Not as a punishment for spending. Not as money you’re hiding from yourself. It’s your trail cushion — the thing that keeps one stumble from becoming a serious fall.

Look Around You

Take a honest look at your life right now. Is it just you? A partner? Kids? A house, a car, maybe two? A pet that just became very expensive?

Here’s the reality: the more responsibilities you carry, the more surface area you have for the unexpected to find you. That’s not pessimism — that’s math. More moving parts means more chances for something to need attention, and attention usually costs money.

This doesn’t mean you live in fear of what might happen. It means you respect the trail enough to be prepared for it.

The Mindset Shift That Changes Everything

Most people treat saving as something they’ll do more of when things get easier — when they earn a little more, when the bills slow down, when life settles. It never settles. The Ascenders who build real financial security don’t wait for perfect conditions. They decide that saving is non-negotiable first, and they build their spending around what’s left.

That means paying yourself first — a minimum of 15% toward your future, whether that’s your emergency fund right now or your retirement account once your safety net is solid. It means automating what you can so the decision is already made before temptation shows up. And it means accepting that some wants get delayed so that your future self has options.

This week isn’t about exact numbers. It’s about adopting a money mindset — one that expects the trail to get rough and plans accordingly.

Focus on the Journey

The hardest part of any long hike isn’t the elevation. It’s the mental discipline of staying present when you’re tired, when the destination feels far away, and when the path isn’t what you expected.

I learned that lesson on a trail in Oregon with a cut on my knee. The destination hadn’t changed. But I’d stopped respecting the journey that was going to get me there.

Set your goals. Know your destination. Then put your eyes back on the trail.

See you at the top.

The AI Avalanche: Keep Your Powder Dry

Monthly Money Man on February 13, 2026

The Bottom Line Up Front: AI is disrupting markets, industries, and jobs at a pace nobody predicted. While the world scrambles to react, the smartest financial move you can make right now isn’t buying AI stocks or panic-selling your portfolio. It’s building cash. Here’s why.

I want to tell you about a client I’ll never forget.

He was a financial advisor’s dream. Successful, motivated, and genuinely excited about investing. Over many years together, we built a diversified portfolio that any advisor would be proud of. Stocks, bonds, real estate, international holdings—the whole trail mapped out perfectly.

Then one day, during a bull market that seemed like it would never end, he called me.

“What’s your next best idea?” he asked.

I thought about it carefully. I looked at his portfolio. I looked at the market. And then I said something I don’t say very often:

“I know exactly what you need right now. And it’s not another investment. You need more cash.”

He went quiet for a moment.

“Cash?” he said. “Why cash?”

“Because when this bull market finally stumbles—and it will stumble—you’re going to want to keep your powder dry. You’re going to want the ability to scoop up quality assets at prices nobody believed were possible. And you can’t do that if everything you have is already deployed.”

He took my advice. And two months later, in September 2008, the market began to crumble. The real estate crisis exploded. The Great Recession had begun—a collapse that nearly brought our entire financial system to its knees.

My client didn’t predict it. He didn’t see it coming.

But he was ready. While others were scrambling to survive, he had cash. While others were forced to sell assets at devastating losses, he was quietly buying quality investments at prices that hadn’t been seen in decades.

Preparation didn’t require prediction. It just required building the base before the storm arrived.

I’m giving you the same advice today.

What’s Happening Right Now

Today, February 12th, 2026, the market had one of its worst days in months.

The Dow dropped 669 points. The Nasdaq fell nearly 2%. Software companies that were market darlings just weeks ago lost billions in value in a single session.

The culprit? Artificial intelligence.

Not because AI isn’t powerful. It is. But because markets are finally waking up to something the rest of us have been feeling for a while: AI isn’t just disrupting technology. It’s disrupting everything.

Jobs that existed for decades are disappearing. Industries built over generations are being rebuilt from scratch. Companies that looked untouchable six months ago are suddenly fighting for survival.

AppLovin—a company that just reported record profits—lost nearly 20% of its value today. Not because it did anything wrong. But because investors are asking a simple, terrifying question: what happens to your business when AI renders it obsolete?

That question is being asked across every industry right now. And nobody has a complete answer.

This is the AI Avalanche. It started as a rumble. It’s becoming a roar.

Why the Avalanche Matters to Your Financial Journey

You might be thinking: “I don’t own tech stocks. What does this have to do with building my emergency fund?”

Everything.

Here’s what history teaches us about periods of massive technological disruption:

They create winners and losers at a speed nobody expects.

The winners are the people who prepared. The ones who had financial stability when chaos hit. The ones who had cash reserves when others were scrambling. The ones who could make clear, rational decisions instead of panic-driven ones.

The losers are the people who were already stretched thin. One job disruption, one industry shift, one unexpected expense away from financial crisis.

Right now, AI is accelerating the pace of disruption faster than any technology in history. Jobs that seemed stable are being automated. Industries are consolidating. The economic ground beneath us is shifting.

This isn’t doom. It’s reality. And reality rewards preparation.

The Strategic Power of Cash Nobody Talks About

Here’s what Wall Street understands that most people don’t:

Cash isn’t just savings. Cash is a weapon.

When markets fall—and today is a reminder that they do fall—cash gives you options that nobody else has.

The wealthy don’t panic when markets drop. They go shopping.

When quality assets fall to prices that reflect fear rather than value, the people with cash reserves step in and buy. They acquire real estate when prices dip. They purchase stocks of solid companies at discounted prices. They invest in opportunities that only appear during periods of uncertainty.

The people without cash? They’re forced to sell at the worst possible time to cover expenses. They watch opportunities disappear because they have nothing to deploy. They make fear-based decisions instead of strategic ones.

My client understood this. That’s why “you need more cash” was the best advice I ever gave him.

It’s the best advice I can give you right now too.

Fortify Your Base Before You Climb Higher

Here’s the mountain climbing truth about where we are right now:

When conditions get unpredictable—when the weather changes and the trail becomes unstable—the smartest thing a hiker can do isn’t push harder toward the summit. It’s strengthen the basecamp.

Make sure your shelter is solid. Check your supplies. Ensure you have what you need to weather whatever comes next.

That’s exactly what building your cash reserve is doing right now.

I know some of you are reading this thinking about investing. About putting money into the market. About not “letting cash sit idle.”

I understand that instinct. But consider this:

If AI disruption continues to shake markets over the next 6-12 months, quality assets could get significantly cheaper. If you have cash reserves, you’ll be positioned to take advantage of those lower prices.

If you have no cash—if everything is already deployed and your emergency fund is empty—a disruption that hits your industry or your job puts you in survival mode, not opportunity mode.

Survival mode and opportunity mode are not the same place.

What This Means for Your February Mission

We’ve spent February building Safety Net #1: one month of cash reserves.

I want you to look at that mission differently now.

You’re not just building an emergency fund. You’re building strategic positioning.

Every $100 you add to your safety net is:

Protection against the job disruption that AI is accelerating across every industry

Stability that lets you make rational decisions when markets get volatile

Ammunition that positions you to take advantage of opportunities when they appear

Freedom from the panic that financial fragility creates

The people who will thrive through the AI avalanche aren’t necessarily the ones who understand AI best. They’re the ones who have the financial stability to adapt, pivot, and act when others can’t.

The Basecamp Principle

In hiking, you never abandon your basecamp until it’s solid.

You don’t push toward the summit with a leaky tent, insufficient supplies, and no safety rope. You prepare. You fortify. You make sure your foundation can support the climb ahead.

That’s what we’re doing right now in February.

The market is volatile. AI is reshaping the economic landscape faster than anyone expected. Industries are being disrupted. Jobs are changing.

This isn’t the moment to sprint toward the summit.

This is the moment to make sure your basecamp can handle whatever weather comes next.

Build your cash reserve. Strengthen your safety net. Fortify your financial base.

Because when the avalanche settles—and it will settle—the climbers who prepared will be the ones who reach the summit.

Your Action Step This Week

The market dropped today. AI anxiety is real. Economic uncertainty is real.

Here’s what you’re going to do about it:

Add to your safety net this week. Whatever amount you can. $50, $100, $200.

Not because you’re scared. Because you’re strategic.

You’re building the financial foundation that gives you options when others have none. You’re preparing your basecamp for whatever conditions lie ahead on this trail.

The AI avalanche is coming. Maybe it’s already here.

The question isn’t whether it will affect you. It will affect all of us in some way.

The question is whether you’ll be ready.

See you at the top.