What’s in Your Financial Backpack? Start With Taxes
The Bottom Line Up Front: Every experienced hiker knows you can’t climb efficiently with a backpack full of unnecessary weight. Tax season is when you empty that pack, examine every single item you’ve been carrying, and decide what actually needs to come with you. Here’s what three days of tax season reminded me about financial organization and the weight most people don’t realize they’re carrying..
I’m sitting at my desk at 5am on a Friday, three days deep into tax preparation, and I’ve just finished my second cup of coffee.
Spreadsheets are open. Documents are scattered across my desk. My digital files look like someone detonated a bomb in a filing cabinet.
And as I sort through another year of financial activity, I’m reminded of something every serious hiker learns the hard way:
You have no idea how heavy your pack is until you empty it out and look at every single thing you’ve been carrying.
That’s exactly what tax season is. It’s the mandatory moment every year when you dump out your financial backpack, spread everything on the ground, and confront the reality of what you’ve been hauling up the mountain.
And for most people, that moment is sobering.
The Backpack You Didn’t Know You Were Carrying
Here’s what I’m finding as I go through my own taxes this week—the same patterns I saw working with hundreds of clients as a financial advisor:
People are carrying subscriptions they forgot existed. As I comb through my credit card statements for deductible expenses, I found one monthly subscription I’d forgotten about and a couple of annual subscriptions I no longer need. None of them feel heavy on their own. But add them up over a year? That’s weight you don’t need to carry.
People are carrying tax bills they could have avoided. I’m watching people around me scramble because they owe money they didn’t budget for. Not because they did anything wrong. But because they didn’t look in their backpack throughout the year to see what they were actually carrying.
Tax season doesn’t add weight to your pack. It just forces you to see the weight that was already there.
And more importantly, tax season is when you reorganize your financial backpack—deciding what stays, what goes, and how to pack it better for the climb ahead.
Why Tax Season Matters More Than You Think
I know most of you would rather do literally anything else than think about taxes right now.
I get it. I’m a former financial advisor, and I still hate this part.
But here’s the truth: tax season is the one time every year when you’re forced to see your complete financial picture.
Every dollar you earned. Every deduction you took or missed. Every account you have. Every financial decision you made for the past twelve months.
It’s all right there in front of you, whether you want to see it or not.
And that clarity—as uncomfortable as it is—shows you exactly what’s been weighing you down.
What I’m Learning From My Own Financial Backpack
Three days into this, here’s what sorting through my financial backpack is teaching me:
When you’re married, you’re climbing together—and filing together. This morning I was going through credit card statements looking for deductible expenses, and I found several charitable donations my wife made that weren’t in my donation folder. If I hadn’t been thorough with the credit card review, we would have missed claiming those deductions entirely. When you file jointly, you’re carrying one combined backpack. You need to know what’s in it from both sides.
Organization doesn’t mean the work is easy—it means the work is thorough. Yes, my donation receipts are in the right place. Yes, my accounts are organized. But matching receipts to credit card statements and verifying every deduction still takes real time and attention. There’s no five-minute shortcut to doing this right.
I’ve been carrying subscriptions I don’t need. That monthly subscription I forgot about and those couple of annual renewals I no longer use? That’s money leaving my account every month that could have been going toward my safety net instead. Tax season is when you catch these things.
Every single one of these things is weight I didn’t need to carry. And I only found them because tax season forced me to empty the pack.
The Questions You Need to Ask When Reviewing Your Financial Backpack
As you prepare your taxes this month—and you need to be preparing them, not avoiding them—here are the questions you should be asking:
What am I carrying that I don’t need?
Look at every subscription charge. Every account. Every recurring payment. If you’re not actively using it, why is it still in your pack?
I guarantee you’re paying for something right now that you forgot you had. Tax prep is when you find it.
What deductions am I missing?
If you’re itemizing, you need to comb through your credit card statements with a fine-tooth comb. Charitable donations. Business expenses. Medical costs. Property taxes.
The people who get the most deductions aren’t the ones who spend the most. They’re the ones who keep the receipts and do the work to claim what’s theirs.
Where are my documents actually going?
Do you have a system for tax documents, or are you scrambling every March to find things?
I’ve watched people waste hours looking for a single W-2 or 1099 that got buried in email. That’s weight. Set up a folder—digital or physical—and put everything there the moment it arrives.
Am I giving the government a free loan?
If you’re getting a big refund, congratulations—you overpaid all year. That’s your money the government has been holding interest-free.
Adjust your withholding. Take that money home in every paycheck instead and put it to work building your safety net, paying down debt, or investing. Don’t let it sit in the government’s backpack when it should be in yours.
Why do I want to look broke by December 31st?
Here’s advisor language most people don’t know: you want to maximize your deductions by year-end. Make charitable donations in December, not January. Max out your retirement contributions before the calendar flips. Prepay property taxes if it makes sense.
The government doesn’t care what you earn. They care what you earned minus what you can legally deduct. The lower that number, the less you carry in taxes.
The System You Need to Build Right Now
Here’s what I’m doing differently this year, and what you should do too:
Create a tax folder today. Every W-2, every 1099, every receipt, every statement goes in one place the moment you get it. No exceptions. No “I’ll file it later.”
Review your withholding if you’re getting a refund. Use the IRS withholding calculator. Adjust your W-4 with your employer. Get your money in your paycheck, not in April.
Track deductible expenses as they happen. Don’t wait until March to figure out what’s deductible. If you make a charitable donation, file the receipt immediately. If you have a business expense, categorize it the same day. And if you’re married, make sure you’re both putting receipts in the same place so nothing gets missed when you file jointly.
Set a reminder for December 15th. That’s when you review what you can do before year-end to reduce next year’s tax bill. Max out retirement contributions. Make charitable donations. Harvest tax losses if you’re investing.
You can’t fix December in April. But you can fix next December right now by building the system.
What This Has to Do With Your Financial Journey
You might be wondering why we’re talking about taxes when we’ve been focused on emergency funds.
Because you can’t climb efficiently with unnecessary weight in your pack.
And taxes—how you handle them, how you organize them, how much you overpay or underpay—are weight.
If you owe money in April you didn’t budget for, that’s weight that crushes your emergency fund progress.
If you’re getting a huge refund, that’s money that should have been building your safety net all year instead of sitting uselessly with the IRS.
If your financial life is so disorganized that tax season causes you three weeks of stress, that’s mental and emotional weight you’re hauling up the mountain.
Tax season is showing you what’s in your pack. What you do with that information determines how efficiently you climb.
Your Action Steps This Week
File your taxes properly and on time. No extensions unless absolutely necessary. Do it right, do it thoroughly, and get it done.
As you prepare, track three things:
- What surprised you (subscriptions, accounts, expenses you forgot)
- What you wish you’d tracked better throughout the year
- What weight you’re carrying that you don’t actually need
If you’re getting a refund: Adjust your withholding and redirect that money monthly.
If you owe money: Figure out why and set up quarterly estimated payments if needed.
Start your tax folder for next year today. Every document that arrives from here forward goes in one place. No exceptions.
Tax season isn’t punishment. It’s the moment you empty your financial backpack, see what you’ve been carrying, and decide what actually needs to come with you on the rest of the climb.
Most of it doesn’t.
See you at the top.
