We’ve all had those “uh-oh” moments with money—checking your balance and wondering where it all went, feeling a wave of guilt after a Target run, or dodging conversations about budgeting because… yikes.

The truth? Most people aren’t bad with money. 

They’re just winging it.

And it’s costing them peace, progress, and often— tens of thousands of dollars.

If you’re not sure where you stand, here are 12 signs you might be winging it with your finances—and why now might be the perfect time to Level Up. 

12 Signs You’re Winging It With Money—And It’s Time to Level Up

1. You avoid checking your bank account. 

If opening your banking app feels like bracing for bad news, you’re not alone. Avoiding your account balance may seem like a stress-reducer, but it actually keeps you in the dark. Money anxiety grows when we don’t face the numbers. Avoidance is often a sign that your money is managing you—not the other way around. The very first step I discuss in my book, Level Up Your Finances, is to gain awareness of how much is in your bank account…. Followed by finding out what your income and expenses are, and how much debt you’re in. Here, you stop guessing and end the feeble attempts at doing it all in your head. This will help you gain clarity. Why is this important? Because when you get organized, the steps to financial freedom get a whole lot clearer. 

2. You don’t know where your money actually goes. 

You get paid, you spend, and by the end of the month you’re wondering where it all went. If you’re swiping without checking and crossing your fingers until payday, that’s winging it. Many people think that tracking spending is enough—but tracking is like trying to drive by looking backwards through the windshield. It shows you what happened, but it doesn’t guide where you’re going. Without a plan, your money has no mission – and that leaves you vulnerable to financial drift.  

3. Budgeting feels like punishment. 

If the word “budget” makes you think of cutting all the fun out of your life, chances are you’ve never used one that works for you. A budget isn’t about restriction—it’s about intention. When done right, budgeting helps you spend with freedom and peace, not guilt and fear. A real budget lets you tell your money where to go before it disappears, and it creates breathing room rather than adding pressure. Instead of feeling deprived, you gain clarity on what really matters to you. A good budget aligns your spending with your values and goals, so every dollar serves a purpose—and you can finally stop guessing and start living with confidence. 

4. You tell yourself, “I’ll start next month.” 

There’s always something coming up—a birthday, a vacation, a busy season at work. But waiting for life to settle down before you get serious with your money is just another way of avoiding it. The perfect time will never come. It’s like waiting until all the stop lights turn green on a street before starting your journey. The best time to start is now. The longer you wait, the more habits get cemented and the harder it feels to break the cycle. Taking one small step today can create momentum you didn’t think was possible. 

5. You’re making decent money but still feel broke.

You’ve got a good job, maybe even a two-income household, but somehow you’re always stressed when the bills are due. If more money hasn’t solved your financial stress, the issue likely isn’t income—it’s the lack of a plan. Money without direction just leaks out. It’s not how much you make, but how intentionally you use it that creates security and peace. And you’re not alone. According to a survey by PayrollOrg, almost 80% of households report living paycheck to paycheck. The good news? You can fix this without needing a raise. And…being intentional with your money can feel like an unexpected raise, with studies showing that getting organized with your finances can instantly give you an extra $400 per month—almost $5,000 a year!

6. You have no clear financial goals.

It’s easy to move through life focusing only on the next paycheck or the next bill, but without clear financial goals, your money has no direction. Whether it’s paying off debt, building an emergency fund, saving for a home, or planning for retirement, having defined goals gives your money purpose. When you know what you’re aiming for, every dollar has a job, and you’re far more likely to stay motivated, make intentional choices, and feel a sense of progress instead of frustration.

7. You dip into savings more than you add to it.

If your savings account feels more like a backup checking account, it’s a sign you’re living without a buffer. Dipping into savings for regular expenses is often the result of not having a clear spending plan (i.e. budget). True savings should protect your future—not patch holes in your budget. Every time you touch savings for day-to-day costs, you erode your safety net and make future true emergencies harder to handle. This is like trying to fill a hole with dirt while at the same time shoveling dirt out the other side—no matter how much you add, you never seem to get ahead. 

8. You stress over every unexpected expense.

A surprise vet bill, car repair, or school fee shouldn’t wreck your whole month. If every unplanned expense sends you into panic mode, that’s a sign you’re running without margin. Living on the edge financially is exhausting, but it’s fixable. Building an emergency fund can transform those moments from crises into inconveniences—and give you real peace of mind. Start with building a $1,000 emergency fund to catch small emergencies while you’re paying off debt (won’t that be great for your stress level?).

9. You spend emotionally—then feel guilty.

Retail therapy is real. Whether it’s buying something to celebrate or numb stress, emotional spending leads to regret when there’s no plan behind it. The problem isn’t that you spend—it’s that your money doesn’t reflect your values or goals. When you align your spending with what matters most and it’s in your budget, you can still enjoy spending—but without the guilt that lingers afterward.

10. You and your spouse avoid money conversations.

If your financial talks always turn into tension (or silence), you’re not alone. Money is one of the biggest stressors in relationships. Avoiding the conversation only lets the stress grow. A shared plan brings clarity, connection, and less resentment. The sooner you start working together, the sooner you can turn money from a source of stress into a tool for building the life you both want.

​​11. Your financial progress feels completely stuck.

You work hard, you make decent money, but nothing seems to change. No real savings, no debt reduction, no forward momentum. That stuck feeling is a result of winging it. Progress requires a system—not just hustle. When you give every dollar a job, you start to see real, measurable change—and that builds confidence for the next step.

12. You’ve tried budgeting, but nothing seems to stick.

It’s easy to think the right app or spreadsheet will magically fix everything. But tools without habits don’t create change. If no system seems to work for you, the problem might not be the app—it might be the approach. You need a method that fits your life. Real change happens when you stop looking for quick fixes and start building consistent habits that feel natural and sustainable. If you want more in depth information about budgeting, check out my article about why budgets fail and what to do about it here.

If more than a few of these hit close to home…

You’re not broken. You’re not behind. You’re just trying to make it work without a clear plan—and that’s exactly why I wrote Level Up Your Finances.

It’s not a spreadsheet-heavy, jargon-filled money book. It’s a real-life guide to finally getting in control of your money in a way that feels doable, grounded, and freeing.

You’ll learn:
✅ The 4 habits that make budgeting actually work
✅ How to build an emergency fund from scratch
✅ What to do if you’re overwhelmed by debt
✅ How to stop the paycheck-to-paycheck cycle for good

You don’t need to be perfect. You just need a plan that works for you.

📘 Ready to stop winging it with money?
Start your fresh financial story today → Level Up Your Finances is available now.

🔗Available as hardcover, paperback and audiobook. 

If you feel really stuck or know you need more help and accountability than a book can give, I also offer personal financial coaching. I’m always available for a free 30-minute session to see if I’m the right fit to help you or someone you care about.