Welcome back, Ascenders!

Last week, I handed you the map for 2026—all 12 months laid out, one clear mission per month, a complete trail to your financial summit.

And if you’re here this week, that means you’re serious. You didn’t just read it and move on. You’re actually doing this.

So let’s talk about January’s basecamp mission: tracking your spending.

I know, I know. It sounds about as exciting as watching paint dry. But here’s the truth—this one boring task is the difference between people who make real financial progress and people who spin their wheels for years wondering why nothing ever changes.

You can’t reach a summit you can’t see. And right now, if you don’t know where your money is actually going, you’re climbing in the fog.

Let’s clear that fog.

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Why Tracking Feels Impossible (And Why You’re Going to Do It Anyway)

Let me guess what you’re thinking:

“I already know where my money goes. Rent, groceries, bills. I don’t need to write it all down.”

Or maybe it’s this:

“I tried tracking once. I lasted three days, forgot to log something, felt like a failure, and gave up.”

Or this one:

“I’m barely keeping my head above water as it is. Now I have to add homework?”

I get it. I’ve heard every excuse because I’ve heard it from hundreds of clients over the years.

But here’s what I learned watching people finally commit to tracking for 30 days: Most people are spectacularly wrong about where their money actually goes.

They think they’re spending $200 a month eating out. It’s $487.

They think their “miscellaneous” spending is insignificant. It’s $340.

They think they have their finances under control. They don’t. They’re just really good at staying unconscious.

Tracking doesn’t show you you’re bad with money. It shows you where you’ve been blind with money. And you can’t fix what you can’t see.

So yeah, tracking is annoying. It’s tedious. It requires you to pay attention.

But it’s also the single most powerful financial tool you have. And you’re going to do it for 31 days, because that’s what Ascenders do.

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The Four Ways to Track (Pick the One That Won’t Make You Quit)

There’s no “right” way to track spending. There’s only the way that YOU will actually stick with for a full month.

Here are your four options. Read them all, pick one, and commit.

Method 1: The Spreadsheet (My Personal Method)

How It Works: Create a simple spreadsheet with columns for Date, Description, Category, and Amount. Every time you spend money—and I mean every time—you log it. End of month, you add it up by category.

This is what I use. Always have, probably always will. There’s something about manually entering each transaction that makes you stay conscious of your spending in a way automation doesn’t.

How to Set It Up: Open Google Sheets (free) or Excel. Create these column headers:

• Date
• What I Bought
• Category (Rent, Groceries, Eating Out, Gas, etc.)
• Amount

That’s it. Don’t overcomplicate it.

Pros:

• Total control over categories
• No account linking required
• Works for cash, cards, everything
• You can customize it however you want
• The manual entry keeps you aware of every purchase

Cons:

• Requires discipline to log everything manually
• Takes more time than apps
• Easy to forget if you don’t make it a daily habit

Who This Is For: You like control, you don’t trust apps with your bank info, or you want to stay actively engaged with every dollar you spend.

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Method 2: The App (Best for Multiple Accounts)

How It Works: Download a spending tracker app, link your bank accounts and credit cards, and let the app automatically categorize your transactions. You just review and correct categories as needed.

I’ve tested one of these. If you use multiple credit cards or bank accounts, an app like Monarch Money does a solid job of pulling everything together in one place so you’re not juggling spreadsheets.

Other Popular Options:

• YNAB (You Need A Budget) (paid, but powerful if you want to budget too)
• PocketGuard (free version available)
• Copilot (paid, designed for Apple users)

Research which one fits your needs—features and pricing vary.

Pros:

• Mostly automatic once you set it up
• Creates charts and reports for you
• Great if you have multiple accounts to track
• Harder to “forget” to track since it syncs daily

Cons:

• Requires linking bank accounts (some people aren’t comfortable with this)
• Cash transactions still need manual entry
• Can be overwhelming with too many features

Who This Is For: You’re comfortable with technology, you use multiple cards or accounts, and you want automation to do the heavy lifting.

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Method 3: The Notebook (Best for People Who Hate Screens)

How It Works: Carry a small notebook in your pocket or purse. Every time you spend money, write it down immediately. Date, what you bought, how much. At the end of the month, add it up by category.

Pros:

• No technology required
• Forces you to be present with every purchase
• Surprisingly effective because the physical act of writing makes spending feel more “real”
• Can’t be hacked or glitch out

Cons:

• You have to carry a notebook everywhere
• Easy to lose or forget
• Requires manual adding at the end
• Harder to create reports or analyze trends

Who This Is For: You’re a pen-and-paper person, you want to feel every dollar you spend, or you’re trying to reduce screen time.

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Method 4: The Envelope System (Best for Cash-Heavy Spenders)

How It Works: Withdraw your monthly spending money in cash. Divide it into envelopes labeled by category (Groceries, Gas, Fun Money, etc.). Spend only what’s in each envelope. When it’s gone, it’s gone.

How to Track It: Keep receipts in each envelope, or just write on the envelope every time you take money out. At the end of the month, you’ll know exactly what you spent because the envelopes will tell you.

Pros:

• Impossible to overspend in a category
• Makes spending tangible and “hurt” a little (in a good way)
• Great for people who struggle with card overspending

Cons:

• Doesn’t work well if you pay most bills online
• Carrying cash everywhere isn’t always practical or safe
• Harder to track non-cash transactions

Who This Is For: You overspend with cards because money doesn’t feel “real,” or you want a built-in spending limit that’s impossible to cheat.

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The Non-Negotiable Rule: Track EVERYTHING for 31 Days

Here’s where most people mess up: they track for a week, think they’ve got the picture, and stop.

Don’t do that.

You need a full month. Here’s why:

Week 1 – You’re hyper-aware and probably spending less than normal because you’re being watched (by yourself).

Week 2 – You start to forget. You miss a transaction here and there. This is where most people quit.

Week 3 – You’re back in real life. This is where the truth shows up—the impulse Target run, the forgotten subscription that auto-renewed, the “just this once” takeout that happens three times.

Week 4 – You see patterns. You realize your “one coffee a day” is actually costing you $120/month. You notice you overspend every weekend. You start to understand your money personality.

One week gives you a snapshot. One month gives you the truth.

So commit to 31 days. Put it on your calendar. Set a daily reminder on your phone. Make it non-negotiable.

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What to Do With Your Data (The Part That Actually Matters)

Okay, you’ve tracked for a month. You’ve got numbers. Now what?

Step 1: Add It All Up by Category

Whether you used an app, spreadsheet, notebook, or envelopes, organize your spending into categories:

• Housing (rent/mortgage, utilities, insurance)
• Transportation (car payment, gas, insurance, Uber)
• Food (groceries AND eating out—track these separately)
• Debt payments
• Subscriptions
• Entertainment
• Shopping
• Miscellaneous (the junk drawer of spending)

Step 2: Calculate Your Big Three Numbers

Remember these from the map? Now you can actually calculate them:

1. Monthly Take-Home Income – What actually hits your bank account after taxes
2. Total Monthly Expenses – Add up everything you spent
3. The Gap – Income minus expenses (this is your surplus or deficit)

Write these down. These three numbers are your financial GPS coordinates.

Step 3: Ask Yourself the Hard Questions

Now comes the part that separates Ascenders from people who just collect data and do nothing with it.

Look at your numbers and ask:

• Where did I think I was spending money vs. where I actually spent it? (The gap between perception and reality is where your money disappears.)
  
• What purchases brought me real value, joy, or necessity? (These are your anchors—the spending that aligns with your life.)
  
• What purchases do I barely remember? (This is the spending that’s robbing you. It’s not making your life better; it’s just making you broke.)
  
• If I could do this month over, what would I change? (This is your roadmap for February.)
  

Step 4: Find Your Leaks

Every financial ship has leaks—places where money drains out without you realizing it. Common ones:

• Subscriptions you don’t use ($10 here, $15 there adds up to $200/month you forgot about)
• Eating out more than you thought ($50/week = $2,600/year)
• Convenience purchases (gas station snacks, vending machines, impulse buys)
• “Just this once” spending that happens weekly

You’re not looking to judge yourself. You’re looking to see clearly.

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What I Learned Watching Thousands of People Avoid This (A Former Financial Advisor’s Observation)

Here’s what I saw over and over when I was a financial advisor:

Successful people—doctors, lawyers, small business owners making six figures—would sit across from me, and I’d ask them to tell me where their money was going.

They’d confidently rattle off the big stuff: mortgage, car payment, maybe some retirement contributions.

Then I’d ask them to track everything for 30 days and come back.

And they’d be shocked. Nearly every single one discovered they were spending $400-800/month on things they couldn’t even remember buying. Subscriptions they’d forgotten about. Eating out “just this once” that happened twelve times. Amazon orders that showed up like surprise packages because they’d already forgotten ordering them.

It wasn’t that they were bad with money. They were just unconscious with it.

Me? I’ve been tracking since I was that kid counting money on my bedroom floor. When you grow up without much, every dollar has a name and a purpose. I couldn’t afford NOT to know where my money was going.

But I learned something powerful working with clients: you don’t have to grow up broke to benefit from tracking. You just have to be willing to turn the lights on and see clearly.

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Your Assignment for Week 2

You’ve got the map. Now let’s take the first real step on the trail:

1. Choose your tracking method (app, spreadsheet, notebook, or envelopes) by Sunday.

2. Track every single dollar you spend for the rest of January. Not most dollars. Every dollar.

3. Set a daily reminder on your phone for 8pm: “Did I log my spending today?”

4. Don’t judge yourself. This month is about gathering data, not being perfect. If you spent $80 on takeout this week, write it down. If you bought something ridiculous on Amazon at 2am, write it down. The truth is the only thing that helps you climb.

5. Check in next Friday. I’ll be back with the next step—how to take this data and actually do something with it.

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The Real Reason This Matters

Here’s what tracking really does: it wakes you up.

Right now, money is slipping through your hands like water, and you don’t even notice. You work hard, you earn a paycheck, and somehow it’s gone by the end of the month and you’re not sure where it went.

Tracking turns the lights on. You start to see every dollar as a choice, not just as money that disappears.

And when you see your choices clearly, you get your power back.

That’s what this month is about—not guilt, not shame, not restriction. It’s about awareness. It’s about taking back control of something that’s been controlling you.

You’re not just tracking spending, Ascenders. You’re setting your basecamp. You’re getting honest about where you are so you can figure out how to get where you’re going.

This is the work. This is the climb.

Let’s do it together.

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Next Week: What to do with all this data (and how to start making real changes in February)

See you at the top.

Here we are – the final stretch of 2025. If you’ve been following along with Monthly Money this year, you’ve checked your accounts, reviewed your spending, maxed out what you could for retirement, and tied up those loose ends that always seem to multiply in December. You’ve done the work.

Now? Now it’s time to step off the trail for a moment.

The View from Here

You know what experienced hikers do when they reach a good vantage point? They don’t immediately forge ahead to the next mile marker. They stop. They take in the view. They pull out their map and plan the next leg of the journey while their legs recover and their perspective expands.

That’s exactly where we are right now, and that’s what I’m asking you to do this week.

Take time with your family. Put the spreadsheets away. Close the banking apps. You’ve prepared your finances for 2026 – that foundation is solid. What you need now isn’t another optimization strategy or one more financial tweak. What you need is space to dream.

Your Assignment (The Fun Kind)

Between now and the New Year, I want you to do something that might feel unfamiliar: spend time envisioning what 2026 could actually look like. Not just financially – holistically.

• What does your family want to experience together?
• What’s one thing you’ve been putting off that deserves your attention?
• Where do you want to be this time next year – not just in net worth, but in life?
• What would make 2026 feel like a year you truly lived, not just survived?

Talk about this with your partner. Include your kids in age-appropriate ways. Dream a little. Maybe dream a lot.

Why This Matters

Here’s something I learned as a former financial advisor and wealth manager and most importantly-a dad: the families who built real wealth weren’t the ones obsessing over every basis point. They were the ones who knew why they were climbing in the first place.

Your money is a tool. It’s there to help you build the life you actually want, not some theoretical perfect financial statement. But you can’t build that life if you haven’t taken time to imagine it.

What’s Next

When we reconvene on January 2nd, we’re going to take everything you’ve envisioned this week and create your 2026 map. Think of it as your trail guide for the year ahead – practical, achievable steps that connect today’s reality with the summit you’re working toward.

But that mapping exercise only works if you’ve done this week’s work. You can’t chart a course to somewhere you’ve never imagined going.

So go. Enjoy your family. Rest. Reflect. Dream.

The climb continues in January, Ascenders – and it’s going to be your best year yet.

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What are you envisioning for 2026? Drop a comment below – I’d love to hear where you’re headed.

Hello there, I’m Tony, and welcome to a very special Financial Friday.

You might notice things look a little different around here. As we continue our climb together, I’m officially transitioning this weekly update to Financial Friday. It’s a small change that reflects our growing community of professionals dedicated to mastering their Monthly Money and reaching the summit of their own Financial Ascent.

Now, as we head into the final week of the year, I can’t help but think of that old Christmas song. Santa is busy making his list and checking it twice—and if you want to end 2025 on the “Nice List” for your future self, you need to do the same.

While everyone else is rushing to the mall, we’re sprinting toward the December 31st hard deadline. These are the final, irreversible actions to maximize your wealth before the clock strikes midnight.

1. The 401(k) and 403(b)Catch-Up Sprint

If you haven’t maxed out your contributions yet, this is your final call. For 2025, the base limit is $23,500.

The Power Move: If you are age 50 or older, you get a “catch-up” bonus of $7,500, bringing your total to $31,000. And if you’re between 60 and 63, 2025 introduced a special “super catch-up” of $11,250 (for a total of $34,750).

• Actionable Step: Check your last pay stub. If you’re short, contact HR immediately to see if you can squeeze one last contribution into your final 2025 paycheck.

Pro-Tip: The 403(b) “15-Year” Secret

If you work for a nonprofit, hospital, or public school and have been with the same employer for 15 years or more, you might have a hidden gift waiting for you. Many 403(b) plans allow a “special catch-up” of up to $3,000 extra per year (with a $15,000 lifetime cap), regardless of your age. If you’re over 50, you can often “stack” this on top of your standard catch-up. Check with your plan administrator—this is a high-level move to supercharge your ascent in these final days of the year!

2. The “Use It or Lose It” FSA Sweep

Unlike your HSA, the money in a Flexible Spending Account (FSA) is often a ticking time bomb. If you don’t spend it by December 31st (or your plan’s specific grace period), that Monthly Money goes back to your employer.

• The Move: Don’t leave money on the table. If you have a balance, now is the time to buy those extra pairs of prescription glasses, stock up on high-end sunblock, or schedule that last-minute dental cleaning. Think of it as a pre-paid Christmas gift to your health.

3. The Hard Deadline Trio: RMDs, Roth Conversions, and Gifts

There are three moves that have zero “grace periods.” Once the ball drops, the window for 2025 slams shut.

• Required Minimum Distributions (RMDs): If you are 73 or older, or have an Inherited IRA, you must take your RMD by December 31st. The penalty for missing it is a staggering 25% of the amount you should have withdrawn. Check those accounts twice!
• Roth Conversions: If you’re looking to convert traditional IRA funds into a Roth IRA to lock in current tax rates, the paperwork must be completed by December 31st to count for the 2025 tax year.
• Annual Gift Exclusion: You can give up to $19,000 per person in 2025 without triggering a gift tax return. If you’re helping children or grandchildren, make sure the checks are cashed or the transfers are initiated now.
  

Tony’s Final Thought for 2025

Discipline isn’t just about saying “no” to bad habits; it’s about saying “yes” to the final actions that protect your progress. By checking these items off your list now, you can head into Christmas morning knowing your financial house is in perfect order.

Actionable Step: Spend 15 minutes today reviewing your FSA balance and your 401(k) and 403(b) totals. It’s the best “gift” you’ll give yourself all year.

Next Week: We move from the sprint to the blueprint. I’ll be sharing the 2026 Financial Roadmap to help you start the New Year at full speed.

Hello there, I’m Tony, and welcome back to Financial Friday!

In the last few weeks, we’ve covered the defensive plays—from shielding your budget against Black Friday debt to making tax-smart donations of your winners. You are in control of your spending and maximizing your charitable impact.

Now, we focus on the final, advanced investment move for the year: Tax-Loss Harvesting.

It sounds a bit silly, doesn’t it? As disciplined investors, we want to buy low and sell high. But right now, we need to look at our losses not as mistakes, but as opportunities to minimize the taxes due in three months. This strategic move is all part of making the most efficient ascent to the top of our Wealth Mountain.

This simple action—Tax-Loss Harvesting—is the final power move to keep more of your hard-earned Monthly Money working for your family’s future.

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1. The Big Idea: Turning Lemons Into Tax Savings

The concept is simple: The IRS allows you to use your investing losses to offset your investing gains.

If you have realized capital gains this year—say, you sold a successful position or received a large distribution from a mutual fund—the IRS will tax you on that profit. Tax-Loss Harvesting uses your portfolio’s losses to offset those profits.

The Math: A Simple Opportunity to “Hide” Gains

• The Problem: You have $10,000 in realized gains (taxable profit).
• The Opportunity: You find a stock or ETF that you bought but is currently worth $8,000 less than what you paid for it.
• The Action: You sell that losing position before December 31st to “realize” the $8,000 loss.
• The Result: You only report a net gain of $2,000$ ($10,000 – $8,000) that is subject to tax. You just used your losses to “hide” $8,000 of your gains from the IRS!

The Extra Bonus: The $3,000 Deduction

If your losses exceed your gains, you get an extra gift:

• You can use up to $3,000 of any remaining net loss to offset your ordinary income (your salary). This is a direct deduction that lowers your taxable income.
• Any losses beyond that $3,000 can be carried forward indefinitely to offset future gains. Your loss never expires!

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2. Don’t Get Caught in the Year-End Market Noise

You are right to notice that the market can get a bit volatile right now. This is a common phenomenon driven by larger investors and institutional fund managers making massive, time-sensitive tax moves.

• The Effect: You might see disproportionate selling in certain sectors where big funds are “cleaning house”—selling their losers to realize tax losses before the deadline. This can cause brief, strange dips in a stock’s price, creating market “noise.”
• Your Strategy: The Ascender’s job is not to react to this noise, but to use it. This is simply the market executing a strategy you should be executing, too. Have your plan ready, identify your target losers, and don’t let temporary dips or volatility scare you out of making your own calculated tax move.

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3. The Decisive Action: The “Sell and Swap” Rule

This is where the strategy moves from simple to smart. You can’t just sell a loser and buy it back immediately; the IRS is watching!

The Wash-Sale Rule prevents you from claiming a tax loss if you buy the same stock or a “substantially identical” security in the 61-day window (30 days before the sale, the day of the sale, and 30 days after the sale).

The rule is designed to stop people from getting a tax break while never leaving their position. But as Ascenders, we don’t want to leave the market! We want to stay invested and growing.

The Solution: The “Sell and Swap”

You must sell the loser and immediately buy a similar, but not identical, replacement.

If you sell…	You can immediately buy…	Why it works
A major S&P 500 ETF (e.g., VOO)	An S&P 500 ETF from a different company (e.g., SCHX)	You stay invested in the U.S. stock market without violating the “substantially identical” rule.
A specific tech stock (e.g., Intel)	A different stock in the same sector (e.g., AMD)	You maintain your exposure to the technology market.

The key is to remain invested so your money is always working for you, but to avoid buying the exact same ticker symbol for at least 31 days. This single, disciplined move protects your deduction and your compounding.

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4. Your Actionable Plan Before December 31st

The clock is ticking on 2025. You must execute this transaction before the market closes on December 31st to claim the loss this year.

1. Run the Report: Log into your taxable brokerage account. Pull the realized gains data for the year. See how much profit you have locked in.
2. Identify the Target: Scroll through your holdings and find any investment with an unrealized loss.
3. Plan the Swap: Before you click “Sell,” know exactly which similar-but-different stock or ETF you are going to buy immediately afterward. Write down the ticker symbols.
4. Execute the Trade: Sell the loser and execute the buy order for the replacement immediately.

This is a true Monthly Money power move. It’s proactive, efficient, and ensures you keep more of your money working to fund your freedom and your family’s future.

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Your Next Action: Run that report today and make a list of your “Sell” and “Swap” targets.

Hello there, I’m Tony, and welcome to another Financial Friday!

Last week, we deployed our Black Friday Shield and focused on defensive spending—setting clear limits to protect our Monthly Money from holiday debt.

This week, we shift to offense.

As established professionals on the journey of The Financial Ascent, December isn’t just about shopping; it’s the critical deadline to execute tax-smart strategies that can save you thousands.

Charity is a core value for many of us. But for high-earners like you, simply writing a check is often the least efficient way to give. Let’s make sure your generosity achieves a powerful double benefit: making a great impact and cutting your tax bill.

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1. The Power of Paperwork: Don’t Forget the Basics

Before we dive into the advanced strategies, let’s nail the simple stuff, because every dollar counts on your tax return.

• Cash is Simple: If you make an outright donation of cash or use your credit card, you get a direct itemized deduction (up to 60% of your Adjusted Gross Income, or AGI). But remember, you need to itemize your deductions for this to matter. If you do use a credit card, at least make sure it’s a cash-back rewards card to get some money back!
• Non-Cash Deductions: That old couch to Goodwill or those clothes to the Salvation Army? You can deduct the fair market value of those items.
• Actionable Step: For any non-cash gift, you must get a receipt and itemize the donation. For itemizers, those receipts are worth real money. The most common mistake I saw as an advisor was people throwing out these receipts. Hold onto those records!

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2. The Double Benefit: Donating Appreciated Stock

This is the single most powerful and overlooked strategy for Ascenders with taxable brokerage accounts. If you have any stocks that have gone up significantly since you bought them (appreciated assets)—which is likely after a strong market year—you should almost never sell them to get cash for charity.

The Problem with Selling

If you sell a stock to donate the cash, you immediately trigger capital gains tax on the profit. That tax bill shrinks the amount of money you have left to give—and it costs you. Do yourself and your charities a favor and be efficient!

The Tax-Smart Solution

Instead of selling, donate the stock directly to a qualified charity.

• Benefit 1 (Deduction): You get an immediate income tax deduction for the full fair market value of the stock, just as if you had donated cash.
• Benefit 2 (Avoidance): You completely avoid paying the capital gains tax on the profit you never realized.

This is a Monthly Money masterstroke: the IRS lets you deduct the gain without ever taxing you on it. It maximizes your giving power and frees up more money for your investment portfolio.

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3. The High-Earner Play: Charitable Bunching with a DAF

For high-earning households, a major challenge is that the Standard Deduction is so high, many struggle to clear the bar to make itemizing worthwhile. This is where bunching comes in—it’s the perfect blend of tax strategy and consistent giving, and it’s why the Donor-Advised Fund (DAF) is your new best friend.

What is Bunching?

Bunching is when you consolidate two or more years’ worth of charitable giving into a single calendar year.

• Year 1 (The Bunch Year): You make a large donation that—when combined with your mortgage interest and state taxes—pushes your total itemized deductions above the Standard Deduction threshold. You itemize and take the massive tax break this year.
• Year 2 & 3 (The Standard Years): You revert to taking the Standard Deduction, which is now the more efficient choice.

The Role of the Donor-Advised Fund (DAF)

The DAF is a simple, low-cost account housed at a public charity (like Fidelity, Schwab, or Vanguard). It makes bunching possible and flexible:

• Immediate Deduction: You contribute the bunched amount (cash or appreciated stock) to the DAF in your “Bunch Year” (e.g., 2025) and receive the full tax deduction now.
• Consistent Giving: The money in the DAF is invested tax-free. You then recommend grants from that DAF to your favorite charities monthly or annually over the next two or three years.

This allows you to achieve the massive one-time tax saving you need, while maintaining the consistent, life-changing support your charities rely on. It’s the ultimate expression of the Monthly Money philosophy applied to giving.

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Your Actionable Step Before December 31st

The clock is ticking on 2025. If you want to use these strategies, the transactions must settle by the end of the year.

• Actionable Step: Review your brokerage account. Identify any long-term holdings (held for more than one year) that have significant unrealized gains. Contact your financial institution today about making a direct transfer of that stock to a charity or a new DAF.

This single move can easily net you a triple-digit deduction on your tax return. That’s more Monthly Money in your pocket, ready to fund your own ascent.

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Your Next Action: If you don’t already have one, start the paperwork to open a Donor-Advised Fund (DAF) today, and identify a position in your investment account with high appreciation that you could donate.

We see a flash sale, and our brain just shuts off, fixated on the “deal.” The truth is, that high of saving money now quickly becomes the stress of having less money for the next six months. We can’t let a weekend sale jeopardize our long-term goals of achieving financial freedom.

Right now, you are laser-focused on conquering your Dual Ascent—saving for college and retirement simultaneously. That’s a serious, focused climb. But what’s the single biggest rock that can trip you up this weekend?

It’s the sheer force of uncontrolled spending that starts right now.

This Friday is Black Friday. For retailers, it’s the starting gun—a race to grab everyone’s money as fast as they can. For us, who are on a decisive quest for financial freedom, clarity, and control—what I call The Financial Ascent—this needs to be the starting bell for the most intentional spending season of the year.

The core of our “Monthly Money” philosophy is simple: consistent action over time. And the most critical action you can take today is defining your limits. Don’t let your wallet run the show.

The Zero-Debt Christmas Challenge: Your Path to Financial Freedom

The “Zero-Debt Christmas Challenge” is your absolute, non-negotiable commitment for the entire holiday season:

You will not acquire a single penny of new, high-interest credit card debt this month, especially for gifts.

Think about it. If you drop $1,000 on a new TV and put it on a credit card, you have effectively told your future self: “I am willing to pay extra for this gift, and I am willing to sacrifice my January savings goal to do it.” That’s not a deal; that’s a contract with complexity.

A responsible Ascender views their paycheck as a series of obligations: Future Savings first, then current needs. Passing the Zero-Debt Challenge means walking away from a purchase that forces you to use borrowed money, securing your peace of mind and accelerating your climb toward financial freedom.

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The Monthly Money Black Friday Action Plan

To ensure Black Friday moves you closer to financial freedom, not further from it, here are the three concrete steps you need to take before you see your first email flyer.

1. The 15-Minute Budget Freeze (The Hard Cap)

Before you log onto a single website, open your bank account and look at the actual cash you have right now. The clock is ticking toward the new year, and you need a hard line.

• Your Action: Set a firm, non-negotiable Monthly Holiday Cap based only on the cash you have on hand. This is the only money available for everything this season (gifts, food, travel, decorations, etc.).
• The Clarity: If your cap is $1,500, that’s the hard limit. Don’t look at available credit; look at available cash. Staying under this cap is the only way to successfully complete the Zero-Debt Christmas Challenge.

2. The Two-List Strategy (The Non-Negotiable Filter)

The most common trap is buying a “great deal” for something you never needed in the first place. You are not buying things; you are buying against your list.

• Your Action: Create two simple lists:
  1. Needs: Specific gifts for specific people that you know you will buy regardless of a sale.
  2. Wants: Non-essential items, upgrades, or things you wish you could get.
• The Clarity: Stick exclusively to the Needs List. If a purchase will force you to use a credit card and break the Zero-Debt Christmas Challenge, it doesn’t matter how good the deal is—you must walk away.

3. The Savings Power Move (The Dual Ascent Reinvestment)

We need to shift the emotional reward from buying to saving. This is the ultimate move for building financial freedom.

• Your Action: Identify a high-pressure, tempting purchase that you successfully rejected because it would have broken your No-Debt rule (e.g., that $400 tablet you almost bought). Now, take the money you were going to spend (the $400) and immediately redirect it.
• The Result: Make an extra deposit: $400 into your 529 college savings account, or perhaps an extra payment toward an existing debt. You get the same rush of instant action, but this time, it moves you toward your goals instead of away from them. This is how you reclaim control of the Dual Ascent.

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Confidence, Not Consumption

You don’t need things; you need financial freedom.

Black Friday is designed to create a sense of urgency and scarcity, but as an Ascender, you know better. This holiday season, you are building a legacy of clarity for your family. Complete the Zero-Debt Christmas Challenge this month, and I promise you will feel proud, purposeful, and ready for your ascent in the new year.