Category: Budgeting & Spending

Welcome back, Ascenders.

It’s Week 4 of January. If you’ve been following along since the beginning of the month, you’ve been tracking your spending, analyzing your data, identifying your leaks, and making commitments for February.

And if you’re being honest with yourself, you’re probably feeling one of these things right now:

“I was so motivated three weeks ago. What happened?”

“I fell off the wagon already. I missed a few days of tracking and now I feel like I failed.”

“This felt exciting at first, but now it just feels like work.”

“I’m not sure I can keep this up for a whole year.”

If any of that sounds familiar, good. You’re right on schedule.

Let me tell you something I learned watching hundreds of people attempt to change their financial lives: the ones who succeeded weren’t the most motivated—they were the ones who knew what to do when motivation disappeared.

Because motivation always disappears. Always. It’s not a character flaw. It’s not weakness. It’s biology.

And today, I’m going to show you how to keep climbing even when you don’t feel like it anymore.

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The Motivation Myth Nobody Tells You

Here’s what most personal finance advice gets wrong: it assumes motivation is a permanent state.

“Just stay focused on your goals!”

“Remember your why!”

“Keep yourself inspired!”

That’s terrible advice. And it’s why most people quit.

Motivation isn’t a permanent state. It’s a spark. It gets you started, but it doesn’t sustain you. Thinking you need to stay motivated for twelve months is like thinking you need to stay excited about brushing your teeth every single day for the rest of your life.

You don’t brush your teeth because you wake up each morning excited about dental hygiene. You brush your teeth because it’s a habit, a system, a non-negotiable part of your routine.

Your financial climb works the same way.

The people I worked with who actually reached their financial summits didn’t rely on motivation. They built systems that worked even when they felt like giving up. Especially when they felt like giving up.

So if your January fire is burning out, that’s not a problem. That’s just the signal that it’s time to switch from inspiration to infrastructure.

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The Four Walls You Need When Motivation Crumbles

When motivation fades—and it will fade, over and over again throughout 2026—you need walls to hold you up. Not inspiration. Not willpower. Walls.

These are the four walls that keep climbers moving when they don’t feel like climbing anymore:

Wall #1: Automation

The Principle: If it requires a decision every time, you’ll eventually decide not to do it.

Remember those three commitments you made for February? The ones about saving money, cutting subscriptions, redirecting spending?

If executing those commitments requires you to manually remember and act every single time, you’ll fail. Not because you’re weak, but because decision fatigue is real.

What to do instead:

Set up automatic systems this week—right now, today—before motivation fades completely:

• Employer retirement contributions (THE BIG ONE): If your employer offers a 401(k) or 403(b) match and you’re not contributing enough to get it, you’re literally leaving free money on the table. Set your contribution to at least the match percentage. This happens automatically from every paycheck, and it’s the single most valuable automatic system most people have access to. If you’re not sure what your match is, check with HR this week.
• Automatic savings transfers: Schedule them for the day after your paycheck hits. You never see the money, so you never miss it.
• Automatic bill payments: Every bill that can be autopaid should be autopaid. One less decision to make.
• Automatic subscription cancellations: If you committed to canceling subscriptions, do it right now. Don’t wait until “later this week.” Later becomes never.
• Automatic tracking syncs: If you’re using an app, make sure it’s syncing automatically. If you’re using a spreadsheet, set a daily phone reminder.

The goal is to remove yourself from the equation. Your motivated self makes the decision once. Your unmotivated self just benefits from it on autopilot.

I’ve watched this play out hundreds of times. The clients who automated everything in January were still saving in December. The ones who relied on “remembering to transfer money” weren’t.

Wall #2: Accountability

The Principle: You’re more likely to follow through when someone else knows what you committed to.

This doesn’t mean hiring a financial advisor (though you can if you want). It means telling one person—just one—what you’re doing and asking them to check in on you.

Who to tell:

• A friend who’s also working on financial goals
• Your spouse or partner (if you have one)
• A family member who won’t judge you
• An online community of people on the same journey (like the Monthly Money Ascenders)

What to tell them:

“I’m working on [specific goal] this year. Can you check in with me once a month and ask how it’s going? I don’t need advice, I just need someone to know I’m doing this.”

That’s it. You’re not asking for coaching. You’re not asking them to fix your problems. You’re just creating a forcing function—a scheduled moment where you have to look someone in the eye (or screen) and report on your progress.

When I worked with clients, the ones who succeeded almost always had some form of external accountability. The ones who tried to do it completely alone? They usually didn’t make it past March.

Not because they weren’t capable, but because humans are wired to care more about social commitments than private ones.

Wall #3: Friction

The Principle: Make the bad behavior harder and the good behavior easier.

When motivation is high, we can resist temptation through sheer willpower. When motivation is low, willpower doesn’t work. You need to change the environment.

Examples of adding friction to bad financial behavior:

• Delete shopping apps from your phone (if impulse buying is your leak)
• Remove saved credit card info from online stores
• Freeze your credit cards in a bowl of water (seriously—you can still use them, but you have to wait for them to thaw)
• Unsubscribe from promotional emails that tempt you to spend
• Block certain websites during work hours if online shopping is a procrastination habit
• Leave your wallet at home when going for a walk (so you can’t impulse buy at convenience stores)

Examples of removing friction from good financial behavior:

• Keep your budget spreadsheet bookmarked and open in a tab
• Put a whiteboard with your financial goal somewhere you see it daily
• Set your savings account as the default transfer destination in your banking app
• Have your meal prep containers washed and ready every Sunday (if eating out is your leak)
• Keep your tracking method in the most accessible place possible

The easier it is to do the right thing and the harder it is to do the wrong thing, the less motivation you need.

Wall #4: Micro-Commitments

The Principle: When you can’t climb the whole mountain, just take the next step.

This is the wall that saves people when everything else fails.

When you’re tired, overwhelmed, or just done with the whole financial journey, you don’t need to recommit to the entire year. You just need to recommit to today. Or this week. Or this one small action.

How to use micro-commitments:

Instead of: “I’m going to track my spending perfectly for the rest of 2026”

Try: “I’m going to log today’s expenses before I go to bed tonight”

Instead of: “I’m going to stick to my budget no matter what”

Try: “I’m going to meal prep this Sunday so I don’t eat out next week”

Instead of: “I will save $10,000 this year”

Try: “I will transfer $200 to savings when my paycheck hits on Friday”

You shrink the commitment down to something so small it feels stupid to not do it. And then you do just that thing. And then tomorrow, you do the next small thing.

This is how every summit is reached—one small commitment at a time, even when you can’t see the top anymore.

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The Two-Minute Rule for Bad Days

Let me give you a tool that saved more people than I can count.

It’s called the Two-Minute Rule, and here’s how it works:

On days when you absolutely do not want to engage with your finances, commit to just two minutes.

That’s it. Two minutes.

• Two minutes to open your tracking spreadsheet and log one transaction
• Two minutes to check your bank balance
• Two minutes to review yesterday’s spending
• Two minutes to transfer $10 to savings (even if you planned to transfer more)

Two minutes is not enough to make progress, right?

Wrong.

Two minutes does three things:

1. It keeps the habit alive. The hardest part isn’t doing the work—it’s starting. Once you’re in motion, you usually keep going. Many times, the “two minutes” turns into ten or twenty because you realize it’s not as hard as you thought.
2. It prevents the shame spiral. When you skip a day, it’s easy to skip two days. Then three. Then you feel like you’ve already failed, so why bother? Two minutes means you never fully stop.
3. It proves to your brain that this isn’t optional. Even on bad days, even when you’re tired, even when you don’t care—you still show up. That builds identity. You become someone who does this, not someone who tries to do this.

I’ve watched people maintain their financial progress through job changes, family emergencies, health crises, and burnout—all because they had the Two-Minute Rule in their back pocket.

You don’t need to be perfect. You just need to not quit.

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What I Learned Watching People Quit (And What Separated the Ones Who Didn’t)

I’m going to be honest with you about something.

Most people who sat in my office and made financial plans didn’t follow through. Not because the plans were bad. Not because they didn’t want it. But because they expected motivation to last, and when it didn’t, they thought they’d failed.

The ones who succeeded? They all had one thing in common: they expected to struggle, and they had a plan for what to do when they did.

They didn’t think “I’ll never feel like quitting.”

They thought “When I feel like quitting, here’s what I’ll do.”

That’s the difference. They planned for the hard days before the hard days came.

So here’s what I want you to do right now:

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Your Week 4 Assignment: Build Your Struggle Plan

This week, you’re not learning new information. You’re building your safety net for the weeks and months when everything feels hard.

Step 1: Identify Your Most Likely Breaking Point

Think about past attempts to change your financial habits. When did you quit? What triggered it?

Common breaking points:

• Something unexpected comes up (car repair, medical bill, etc.)
• You have one “bad” spending day and feel like you failed
• You get bored or tired of tracking
• Life gets busy and this feels like one more thing on your plate
• You don’t see results fast enough

Write down your most likely breaking point: _______________

Step 2: Create Your “When This Happens” Plan

Now, create a specific if-then plan:

“When [my breaking point happens], I will [specific action].”

Examples:

• “When I have an unexpected expense, I will log it in my tracking, adjust next week’s budget, and keep going—not treat it as failure.”
• “When I miss two days of tracking, I will use the Two-Minute Rule: spend two minutes catching up on just those two days, nothing more.”
• “When I feel overwhelmed, I will text [accountability person] and ask them to remind me why I started.”

Write your if-then plan: _______________

Step 3: Set Up At Least One Automation This Week

Pick the lowest-hanging fruit from Wall #1:

• Schedule automatic savings transfers
• Cancel one subscription you committed to cutting
• Set up automatic bill pay for one recurring expense
• Schedule a recurring calendar reminder to track spending

Do one. Just one. Right now, before motivation fades even more.

Step 4: Tell One Person

Text, call, or message one person this week and tell them what you’re working on. Ask them to check in on you in February.

Just one person. It takes five minutes.

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The Truth About February (And Why This Week Matters)

Next week, we’re moving from January’s basecamp mission (tracking and analysis) to February’s mission: building your emergency fund.

But here’s the thing: if you don’t have systems in place before February starts, you won’t build the fund. You’ll have good intentions, and you’ll think about it, but you won’t actually do it.

This week—Week 4, the week when motivation starts to fade—this is the most important week of the entire month.

Because this is the week where you decide: Am I going to rely on feelings, or am I going to rely on systems?

The climbers who reach the summit aren’t the ones who feel motivated every day. They’re the ones who built a system that works even when they don’t feel like climbing.

So build your walls this week. Set up your automation. Tell your person. Write your struggle plan.

Because motivation will fail you. But your systems won’t.

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A Final Word: You’re Not Behind

If you’ve already missed days, skipped tracking, broken a commitment, or feel like you’re failing—you’re not behind.

You’re exactly where most people are at Week 4. The only difference between people who quit and people who succeed is what they do next.

Quitters think: “I already messed up, so what’s the point?”

Climbers think: “I stumbled. Now I take the next step.”

That’s it. That’s the whole difference.

You don’t need to be perfect. You don’t need to be motivated. You just need to take the next step.

And then the one after that.

See you next week when we start building your emergency fund. I’ll be there. Will you?

See you at the top.

Welcome back, Ascenders!

If you’ve been following along, you’ve spent the last two weeks doing something most people never do: tracking every single dollar you spend.

And if you’re like most people, you’re probably sitting there looking at your numbers thinking one of two things:

“Well, that’s not as bad as I thought.”

Or…

“Holy crap, where did all my money go?”

Both reactions are completely normal. But here’s what matters: you now have something incredibly powerful that most people don’t have—the truth.

You know where your money is actually going. Not where you think it’s going, not where you wish it was going, but where it’s really going.

Now comes the part that separates people who track their spending from people who actually change their lives: doing something about it.

This week, we’re going to take that data you’ve collected and turn it into decisions. Real ones. The kind that will set you up to crush February’s mission and keep climbing toward your 2026 summit.

Let’s go.

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The Three Questions That Change Everything

Before we dive into the numbers, I want you to grab whatever you’ve been tracking with—your app, your spreadsheet, your notebook, your envelopes—and answer these three questions honestly:

Question 1: What surprised you most?

When I worked with clients as a financial advisor, this question always revealed the biggest blind spots. Someone would say, “I had no idea I was spending $400 a month eating out” or “I didn’t realize that gym membership I never use costs me $720 a year.”

The surprises aren’t about judgment. They’re about awareness. Write down what surprised you. That’s where your money has been disappearing without your permission.

Question 2: What would you change if you could do this month over?

Not everything. Don’t make a list of 47 things you’d do differently. Just pick the top 3-5 expenses that, looking back, you wish you hadn’t made. Not because they were “bad,” but because they didn’t add real value to your life.

Maybe it’s the subscription you forgot you had. Maybe it’s the impulse Amazon order. Maybe it’s the takeout on a night when you had food in the fridge but were too tired to cook.

Write those down. These are your action items for February.

Question 3: What brought you real value, joy, or necessity?

This one’s important because cutting spending isn’t about deprivation. It’s about alignment.

Some of your spending is working for you. The coffee shop where you meet a friend every week? That’s relationship maintenance. The gym membership you actually use three times a week? That’s health. The quality groceries that make you feel good? That’s taking care of yourself.

Write down what’s worth keeping. These are your anchors—the spending that stays because it genuinely improves your life.

Now you’ve got clarity. Let’s use it.

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Your Financial Leaks: Where the Ship Is Taking On Water

Remember last week when I mentioned that every financial ship has leaks? Now it’s time to find yours.

Pull out your spending data and look for these five common leak patterns:

Leak #1: The Subscription Graveyard

This is the easiest leak to spot and the most satisfying to fix.

Go through your statements and highlight every recurring charge—streaming services, apps, memberships, subscription boxes, software, anything that auto-renews.

Now ask yourself: Did I use this in the last 30 days?

If the answer is no, cancel it. Today. Right now. Don’t wait until “later” because later never comes.

I’ve seen clients spending $200-500 a month on subscriptions they barely remember signing up for. That’s $2,400-6,000 a year just… gone. For nothing.

Cancel the dead weight. You can always resubscribe later if you actually miss it. (Spoiler: you won’t.)

Leak #2: The Convenience Tax

This leak is sneakier. It’s all those small purchases that feel insignificant in the moment but add up to shocking totals over a month.

Gas station snacks. Vending machine drinks. Coffee shop stops when you have coffee at home. DoorDash fees when you could have picked it up. Paying for express shipping when standard would’ve been fine.

Look at your tracking data and add up all the purchases under $10 that you made for pure convenience, not genuine need or joy.

I’m not saying never buy convenience. I’m saying be conscious about it. Because $5 here and $8 there turns into $300-400 a month real fast.

Leak #3: The Weekend Bleed

Most people’s spending looks reasonable Monday through Friday, then explodes on weekends.

Add up just your Friday, Saturday, and Sunday spending for the month. For a lot of people, weekends account for 40-50% of their total spending despite being only 28% of the days.

This isn’t about not having fun on weekends. It’s about realizing that your “normal” spending and your weekend spending are two completely different patterns, and the weekend pattern is probably the one sinking your ship.

Leak #4: The Emotional Spending Spiral

Look at your biggest impulse purchases this month—the ones that weren’t planned, weren’t necessary, and honestly, you could’ve done without.

Now ask yourself: What was I feeling right before I bought this?

Stressed about work? Bored? Sad? Celebrating? Avoiding something?

In my years as an advisor, I saw emotional spending patterns constantly. One client would “reward” herself after stressful work days by shopping online—$300-400 a month she didn’t even remember spending. Another would hit the grocery store when he was anxious and come home with $200 of food that went bad in the fridge. Someone else bought things late at night when she couldn’t sleep, racking up purchases she’d forgotten about by morning.

Identifying your emotional spending pattern is like finding the source of the leak. Once you see it, you can patch it.

Leak #5: The “Just This Once” Lie

Go through your tracking and look for expenses you justified with “just this once.”

Eating out “just this once” because you had a long day. Buying something “just this once” because it was on sale. Upgrading to the nicer option “just this once” because you deserved it.

Now count how many times “just this once” actually happened this month.

If “just this once” happened six times, it’s not once. It’s a pattern. And patterns are leaks.

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The Reality Check: Your Big Three Numbers

Alright, time for the moment of truth.

Pull out your calculator (or just use your phone) and let’s calculate your Big Three numbers. These three numbers are your financial GPS—they tell you exactly where you are and exactly what you need to do next.

Number 1: Monthly Take-Home Income

This is what actually hits your bank account after taxes, retirement contributions, health insurance, and any other deductions.

Don’t use your salary. Use what you actually receive. If you get paid every two weeks, multiply one paycheck by 26 and divide by 12. If you get paid twice a month, multiply by 2.

Write this number down: $_______

Number 2: Total Monthly Expenses

Add up everything you spent this month. And I mean everything—rent, groceries, gas, subscriptions, eating out, shopping, debt payments, the random $3.47 you spent at a convenience store, all of it.

This number might hurt to see. Write it down anyway: $_______

Number 3: The Gap

Take Number 1 minus Number 2.

If this number is positive, congratulations—you have a surplus. This is your fuel for climbing. This is what you’ll use to build your emergency fund in February, pay off debt, and reach your summit.

If this number is negative, you’re spending more than you make. This is not a moral judgment, it’s just math. And math can be fixed.

Write down your gap: $_______

Now you know exactly where you stand.

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The Decision Matrix: What Stays, What Goes

Here’s where we turn awareness into action.

You’ve identified your leaks. You’ve calculated your Big Three. Now you need to make actual decisions about what changes starting February 1st.

But here’s the key: you can’t fix everything at once.

When I worked with clients who tried to overhaul their entire financial life overnight, they’d last about two weeks before everything fell apart. Too much change, too fast, creates too much resistance.

Instead, we’re going to use what I call the Decision Matrix. It’s simple:

Draw two lines to make four boxes. Label them:

• Keep (High Value): Expenses that genuinely improve your life
• Cut (No Value): Expenses you don’t care about and won’t miss
• Reduce (Some Value): Expenses you want to keep but could scale back
• Replace (Better Option): Expenses where there’s a cheaper alternative that gives you the same benefit

Now go through your spending and sort everything into these boxes.

Examples:

Keep: Gym membership you use 3x/week, quality groceries, coffee meetups with friends, therapy, car insurance

Cut: Subscriptions you don’t use, apps you forgot about, memberships to places you never go, things you bought on impulse and don’t care about

Reduce: Eating out 12x/month → 6x/month, Premium streaming plans → Basic plans, Brand name everything → Generic for some items

Replace: Eating out for lunch daily → Meal prep Sundays, Buying coffee out → Making it at home except for friend meetups, Cable → Streaming (if you haven’t already)

The goal isn’t to cut everything. The goal is to be intentional about everything.

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What I Learned Watching People Make (and Break) This Moment

Here’s the thing about having financial data: it only matters if you actually do something with it.

Over the years as an advisor, I watched hundreds of people sit in my office, look at their numbers, nod seriously, and say “I’m definitely going to fix this.”

Some did. Most didn’t.

The ones who succeeded had something in common: they made specific commitments before they left my office.

Not vague promises like “I’ll spend less eating out.” Specific decisions like “I’m canceling Netflix tonight, meal prepping on Sundays starting this week, and limiting restaurant meals to twice a month.”

The ones who failed? They left with good intentions and no plan.

Don’t be that person.

Right now, before you close this article, you’re going to make three specific commitments for February. Not ten. Three.

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Your Three Commitments for February

Look at your Decision Matrix. Look at your leaks. Look at your gap.

Now write down three specific changes you’re committing to starting February 1st.

My Three February Commitments:

Make them specific. Make them measurable. Make them realistic.

Bad commitment: “Spend less money eating out”

Good commitment: “Meal prep every Sunday, eat out maximum 2x per week, budget $100/month for restaurants”

Bad commitment: “Cancel some subscriptions”

Good commitment: “Cancel Netflix ($15), Spotify Premium ($11), and that app I don’t use ($5) by February 5th = $31/month savings”

Bad commitment: “Save more money”

Good commitment: “Automatically transfer $200 from checking to savings on the 1st and 15th of every month”

See the difference? Specific commitments give you a clear target. Vague intentions give you an excuse to do nothing.

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Setting Up Your February Mission: The Emergency Fund

Here’s why all of this matters.

In last week’s map, February’s mission is building your emergency fund. But you can’t build an emergency fund if you don’t know where the money is going to come from.

That’s what this exercise was about.

Your three commitments? Those are creating the breathing room in your budget. Those cut subscriptions? That reduced eating out? That replaced expensive habit with a cheaper alternative? That’s your emergency fund fuel.

Let’s do some quick math:

If you found three leaks that each save you $50/month, that’s $150/month.

Over the course of 2026, that’s $1,800 that was disappearing into nothing but is now working for you.

In February alone, that $150 either gets you halfway to your first $500 emergency fund milestone, or it adds a month of expenses to your existing fund.

This is how you climb. Not with dramatic sacrifices or miserable deprivation, but with conscious decisions about where your money goes.

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The Week 3 Assignment: Lock It In

You’ve done the analysis. You’ve made the commitments. Now you need to lock them in before motivation fades and old habits creep back.

Here’s your assignment for this week:

1. Execute your cuts immediately

If you committed to canceling subscriptions, do it today. Don’t wait until “later this week.” Go to the websites right now and cancel. Set a 10-minute timer if you need to—it doesn’t take long.

2. Set up your automation

If you committed to automatic savings transfers, log into your bank right now and schedule them. If you’re going to meal prep on Sundays, put it on your calendar as a recurring event.

Systems beat willpower every time.

3. Calculate your projected February surplus

Based on your three commitments, how much more breathing room will you have in your budget next month? Write that number down. That’s what you’re aiming at for your emergency fund.

4. Check in here next Friday

I’ll be back next week with Week 4: What to Do When Your January Motivation Starts Fading. Because it will. And that’s okay. We’re going to be ready for it.

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The Real Point of All This

Let me be straight with you.

The point of tracking your spending wasn’t to make you feel bad about where your money went. The point wasn’t even really about the money.

The point was to wake you up.

Right now, you’re awake. You can see clearly. You know where the leaks are. You know what needs to change. You have a plan.

This feeling—this clarity, this sense of “okay, I can do this”—this is the feeling you need to act on.

Because here’s what I’ve learned after watching thousands of people work through this process: the clarity doesn’t last.

A week from now, when you’re tired and stressed and someone suggests getting takeout, your brain is going to whisper “just this once.”

A month from now, when you see something you want on sale, your brain is going to rationalize “but it’s such a good deal.”

That’s normal. That’s human. That’s why most people never make it past basecamp.

But you’re not most people. You’re an Ascender. And Ascenders don’t quit when motivation fades—they rely on the systems they built when motivation was high.

So lock in your three commitments. Set up your automation. Make the cuts while you still have the clarity to do it.

Your February self will thank you.

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Next Week: What to Do When Your January Motivation Starts Fading (Spoiler: It’s not about willpower)

See you at the top.

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.

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.