I thought I'd have more money by now...
This week’s question:
"Hi Tess! Thanks for all your help so far. I have $10k in credit card debt, $30k in low-interest student loans (under 4% interest rate), but I also want to be saving for a house and making sure I’m investing for retirement because I know I'm behind (I'm 44 and don't have nearly as much as I thought I would at this point!). I want to switch careers and start my own business, so I want to set myself up for that too. I hate having debt and want it gone ASAP. What should I prioritize?"
Thoughts From Tess:
First of all, thank you for sharing this! You’re certainly not alone in feeling overwhelmed juggling multiple financial priorities. Most women I work with are battling with some version of this same question: how do I handle my current responsibilities while building the future I want?
Here's how I would tell you to prioritize if you were my best friend that I felt I could be brutally honest with:
1. The credit card debt has to go, ASAP.
It’s your highest-interest debt and over time it will cost you a lot of money. But paying it off isn’t enough....
You also need to look at the pattern that caused it. If it came from unexpected expenses, that’s a sign you need a stronger emergency fund. If it came from day-to-day spending and you’re not paying your balance off each month, it’s time to take a hard look at cash flow: is your life costing more than you make?
Paying it off is step one. Addressing the behavior behind it is step two.
2. Learn how to invest and optimize what you already have.
You already have a 401(k) and IRA, which is a great start! But now it’s time to make sure that money is actually growing for you. Some common mistakes I see:
Investing too conservatively for your age (too much money bonds, not enough in stocks will hinder growth).
Paying high fees is another issue. 1% to an advisor is a lot of money over time. On top of that, every fund you are invested in also has a fee. Most people don't realize these funds can add up to six figures in fees over time.
Putting off learning to invest for years is a huge mistake. And then when my students realize it takes just a few weeks to learn the basics, they get mad they didn’t start sooner.
Don’t wait. Low-cost index funds are a great strategy for most people, and you don’t need to be an expert to get started.
3. Don’t pause investing.
Even if it’s just $100/month, keep it going. Compound interest is more powerful than we realize. Momentum matters.
4. Build your business buffer.
If starting your own thing is part of the plan, give yourself a financial runway. A 3–6 month “freedom fund” can turn a risky leap into a confident move and you'll be making decisions from a place of calm, not panic.
I'm also not a fan of the "burn the boats" mentality. Studies show that people that start to build something on the side while they still have consistent income are often more successful that those that quit their main job and go all in on their business.
5. House goals. My tough love answer...press pause (for now).
If you were my best friend this is what I'd tell you: this probably isn’t the moment to prioritize saving for a house.
Trying to do it all at once...pay off debt, invest, build a business, and save for a down payment....this leads to overwhelm and frankly, likely being unsuccessful in any financial goal.
If owning a home is still your dream, we can absolutely revisit it once your foundation is stronger. For now, ask: What am I really looking for in a home? Do I need that feeling now, or can it wait 1–2 years?
Bottom line: You’re asking the right questions. Now take it one step at a time. Clear the credit cards. Make sure your investments are working. Keep some money going toward your future. Then layer in the next goal. Trying to do everything at once slows you down more than it speeds you up.
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