Every December, people enter the month with a mix of joy, stress, optimism, and financial panic, often all at the same time. The holidays are magical, yes, but they’re also chaotic, emotional, and expensive. 

For many of us, December brings the same sinking feeling: “How did this month sneak up on me again… financially?” If that’s you, you’re not alone. 

For years, I found myself doing mental gymnastics in store aisles, trying to decide whether to put a gift on a credit card, wait for a sale, or pretend I never saw it and choose something “sentimental” instead. Every December felt like a surprise attack on my bank account.

But this year, I want to draw a line in the sand with you: this is the last year you will ever feel unprepared for the holidays. And what’s powerful is that the change doesn’t come from earning more money or finding a magical Black Friday loophole. It comes from shifting one belief: every dollar needs a job. 

When you give your money clear, specific roles, the guilt you usually feel around holiday spending evaporates. The real problem isn’t spending, it’s surprise spending, and December is full of expenses we pretend we couldn’t have seen coming. Christmas, Hanukkah, Kwanzaa, travel, food, traditions, they all happen on the same days every year. They don’t sneak up; we just don’t plan ahead for them. Once I stopped treating December like an ambush and started planning for it intentionally, everything changed.

Suppose you’re only starting your holiday shopping now. In that case, there’s usually one reason: you’re waiting for the month when you finally have a little extra money. Years ago, when I lived paycheck to paycheck, I didn’t buy a single gift until December because it was the first time all year when my cash flow loosened up enough to make it possible. And that wasn’t poor planning, it was reality. 

Cash flow

The encouraging part is that our reality can shift quickly when you move from reactive spending to proactive planning. Instead of “spend and feel guilty,” you move to “plan and feel confident.” 

Instead of letting December tell you how stressed you’ll be, you get to tell December how it’s allowed to behave.

The simplest, most effective step you can take right now is to open a separate bank account labeled exactly “2025 Holiday Spending.” Not “savings,” not “miscellaneous,” not “future expenses.” Call it what it is, so your brain knows precisely what that money is for. Then automate a tiny percentage of every incoming dollar into it; 1%, 0.5%, five bucks, whatever is comfortable for you. Small, automatic amounts add up fast, and after a year of these micro-transfers, you’ll suddenly have a holiday fund that feels like pure magic. But it isn’t magic—it’s consistency. And consistency is what creates financial freedom and reduces holiday stress.

This shift isn’t just about Christmas or holiday budgeting. It’s about restoring control. When I talk with people about money, it seems that most people don’t truly crave wealth; they crave certainty. 

You want to know when money is coming in, where it’s going, and whether it will still be there when you need it. Clear roles for your money give you clarity, and clarity gives you confidence. Once you take control of one area, like good ‘ol holiday spending, you begin to feel in control of your money. You move from chaos to calm, from confusion to clarity, from emotional spending to intentional planning. That’s the power of assigning every dollar a job.

Debt

While we’re talking about clarity and control, let me also tackle a deeply misunderstood topic: debt negotiation. Many people imagine it as a confrontational battle under harsh fluorescent lights, with creditors demanding every last dollar. In reality, creditors are human. They would far rather receive a partial payment than no payment at all. Debt negotiation is often simple, calm, and mutually beneficial. When you understand that, you start taking back power you thought you’d lost. The same skills you’re building by creating a holiday spending account—clarity, communication, confidence—are the exact skills that help reduce financial stress in other areas of your life.

And this is why this December matters so much. It can become your reset point, the moment you decide to stop repeating the same stressful pattern and start building a new financial story. You’re not behind. You’re not irresponsible. You’re not doomed to have chaotic holidays forever. You’re just at the beginning of a more intentional relationship with money. Imagine next December: you open your 2025 Holiday Spending account and see a balance waiting for you. You buy gifts without guilt or uncertainty. You enjoy the season without that familiar knot of financial stress in your stomach. You walk into stores with confidence instead of worry. And most importantly, you trust yourself, because you followed through, created structure, and stayed consistent.

So let’s make this the last year you ever feel unprepared. Start today by opening that account, labeling it clearly, and automating a small, steady amount into it. Small steps create massive change, and this one action can transform how you experience the holidays this year, next year, and every year after. 

Let December be intentional instead of chaotic. Let your money work for you instead of surprising you. Let this be the moment you turn the page and step into a calmer, clearer, more confident financial future.

And I know you’ve got this!

-Mike

PS – Some exciting things are happening!

In case you missed it, we made 6 episodes of the Becoming Self-Made podcast. This is the good stuff. The real stories and free business advice from those who have blazed trails in the entrepreneurial space that you cannot do without. I am so excited to have teamed up with Relay on this project, and we’re talking with heavy hitters like Jesse Cole from Savannah Bananas, Don Miller of Storybrand, and many more! Don’t miss out.

• Visit the podcast homepage for all updates and link to your favorite podcatcher to download all the episodes: Becoming Self-Made Podcast

And as always, free resources to support you are here on my website. From the Profit First Assessment to just about anything else you need!