I Made More Money and Still Felt Broke (Here’s What I Missed)
Why your biz might be “growing” but your bank account isn’t…
My Credit Card Chronicles: A Cautionary Tale
When I first started my business, I didn’t have cash flow, I had a credit card and a dream.
So I did what many entrepreneurs do:
I charged a website host and a gorgeous (read: expensive) theme.
Then an email marketing platform.
Then a project management software upgrade.
Then a coaching program.
Then a VA.
And to be fair? None of those were bad investments. They helped me grow. They moved the needle. They made me feel legit.
But here’s the problem:
Even with more clients and more revenue, I wasn’t seeing any more money in my pocket.
My credit card balance didn’t budge despite regular payments.
Which was extra annoying because, well, I’m a math nerd. I reconcile my checking account for fun. Like… on Friday nights. Willingly.
So why was I stuck?
The Lightbulb Moment
It wasn’t until I interviewed a Profit First coach on my podcast that it hit me:
I was great at tracking money.
I was terrible at budgeting it.
No system. No rules. Just vibes and subscriptions.
And that had to change.
Here’s the part we don’t talk about enough: reinvesting in your business feels noble. Responsible. Smart.
And for a while, it is.
But when you’re constantly reinvesting everything back in, without giving yourself a paycheck, rest, or reward… you start feeling resentful. Even if the business is doing well.
Bitterness doesn’t wait for burnout. It shows up quietly, when your energy is high, but your pockets are empty. When you hit a new revenue milestone… and still can’t afford to give yourself a raise.
You wouldn’t stay at a job where the stress was high but the pay was lousy (or they never paid you at all) right? Don’t be that boss for yourself!
This is what Be Your Own Boss BETTER is all about. Building a business that pays you in actual dollars, not just long hours and intangible success.
How to spend money like a CEO
The real issue wasn’t my revenue.
It wasn’t my tools.
It wasn’t even my spending, technically.
It was my lack of a system for spending.
I was amazing at tracking money.
But evaluating ROI before the swipe?
Let’s just say… my business brain was still in “treat yo’ self” mode.
If that sounds familiar, keep reading.
I created a checklist. A simple “Do I really need this?” filter to help me stop confusing growth with accumulation.
Here it is. Steal it. Save it. Tattoo it on your wallet.
Your “Think Like a CEO” Expense Checklist
Before every swipe, every subscription, every “limited time” upsell, ask:
- Will this directly make me money or save me time?
- Am I solving a real problem or avoiding a tough decision?
- Do I already have something that does this?
- Will I actually use it weekly or is this just aspirational?
- How will I measure ROI?
- Am I buying out of clarity or FOMO and stress?
No shame. Just smarter questions.
thecaffeinatedentrepreneur.com 