What Your Money Trail Is Trying to Tell You
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Next Week: What to Do When Your January Motivation Starts Fading (Spoiler: It’s not about willpower)
See you at the top.
