We’re All Bad at Investing (But Not In the Way You Think)

Jenny Whichello, Bliss + Wealth
4 min readFeb 3, 2024


Investing. The word conjures images of Wall Street wolves and ticker tape, a complex dance between risk and reward. We readily acknowledge that mastering this arena takes time and knowledge. But here’s the truth, ladies: we’re pretty good at investing (the stats back that up). But while we may not be bad at investing in the stock market, oftentimes we’re terrible at investing in ourselves.

Hold your horses, financial feminists! Before you grab your pitchforks, hear me out. This isn’t about stock-picking prowess or investment strategies. It’s about a subtler form of financial mismanagement — the chronic undervaluing of investing in ourselves.

Think about it. We diligently research stocks, analyze trends, and agonize over fees. Yet, when it comes to investing in our own growth, well-being, and earning potential, we often throw caution to the wind. We hesitate to hire coaches, shy away from negotiation workshops, and resist pursuing opportunities that demand upfront costs for long-term gains.

While we struggle with making investments in ourselves, we have no problem investing in others, mainly credit card companies and banks. The average American spends $1,000 each year on interest payments, often from financial decisions they spent little to no time contemplating. So why don’t we thoroughly debate those decisions in the same way we do the choices that actually benefit us in the long-run? No one likes paying credit card interest, but most would have a hard time taking that same $1,000 and investing it in themselves. Strange, huh?

Why this self-sabotaging behavior?

Here’s the culprit: the invisible ROI meter. Unlike stocks with clearly defined returns, investing in ourselves often comes with intangible benefits — confidence, skills, career advancement — that defy easy quantification. This lack of immediate, measurable ROI fuels our hesitation.

But here’s the secret: the most valuable investments often yield returns beyond mere numbers. Investing in a career coach could translate to a higher salary negotiation, a writing workshop might blossom into a published book, and a public speaking course could land you dream clients. The ROI isn’t just financial; it’s personal and professional empowerment. Oh, and sometimes it actually does produce financial returns!

So, how do we stop being bad at investing and become savvy self-investors?

Here’s your action plan:

Reframe the Narrative: Stop thinking of self-investment as an expense, see it as an investment in your future self. Would you hesitate to invest in a promising new business venture? Treat your own growth with the same respect.

Identify Your ROI Sweet Spot: What are your personal and professional goals? What skills or knowledge would unlock those goals? Quantify the potential benefits, not just in dollars, but in time saved, stress reduced, or opportunities gained.

Start Small, Scale Up: Don’t overwhelm yourself with a 12-month course. Begin with a workshop, a book, or a mentorship — small investments with tangible outcomes. As your confidence and ROI meter tick up, you’ll be ready for bigger leaps.

Build Your Support Squad: Surround yourself with women who believe in the power of self-investment. Share your goals, celebrate each other’s successes, and hold each other accountable. Remember, you’re not alone in this journey!

Investing in ourselves isn’t just about fancy retreats and expensive courses (though those can be part of it!). It’s about recognizing our own worth, prioritizing our growth, and making strategic choices that unlock our full potential. So, ditch the invisible ROI meter, embrace the power of self-investment, and watch your future self reap the incredible rewards.

Wanna stop being bad at investing?

Here’s my challenge to you:

Can you start to see every spending decision as an investment? For example, when I choose to buy a latte at my local coffee shop, I’m investing in my community and the woman founder. When I renew my Calm subscription, I’m investing in my mindfulness practice (and my peace of mind). And when I decline a shopping trip to Target, it’s because I don’t see much ROI in another shopping cart full of candles and throw pillows.

Remember, you are worthy of every investment that propels you towards your dreams. Now go forth, invest in yourself, and rewrite your financial narrative, one empowered decision at a time!

Bonus Tip: Ease into change with these free resources to fuel your self-investment journey:



Jenny Whichello, Bliss + Wealth

On a mission to help the next generation of unstoppable women have blissful relationships with money while building wealth! Free resources @ blissandwealth.com