I feel incredibly lucky to have made some TRULY horrifying mistakes when it comes to money.

I mean… I’ve made a lot of mistakes in my life – but these were *particularly* impressive. If we could take a peek back in time to my 20’s there I would be – just tryin to live my best life! Cars I couldn’t afford and clothes I didn’t need, trips with first class flights, lavish Christmases and meals at amazing restaurants – all financed courtesy of an astronomical amount of student loans.

I saved almost nothing for retirement, took out credit cards and maxed the balances, and had a love affair with designer items whose price tag rivaled (and often FAR exceeded) my monthly salary. (But, it’s fine, right? I was about to finish grad school!) I finished my MBA, landed my dream job in corporate finance and thought I had it MADE. (Insert money raining from the sky!!!)

Raining Money!

Then I got to experience a Universal truth: No matter how much money you make, you can STILL be broke.

If you don’t address the underlying issues with money and worth, you will spend Every.?? Dollar.?? That.?? You.?? Make.??

So money flowed in and flowed right back out. No matter what, my finances never changed. It was official – I was as broke as ever. So looking back…. Would I change ANY of it? Nope. Because I gained an unbelievable insight into myself and my beliefs that I couldn’t have gotten any other way. Was it expensive insight? Absolutely – but every step any of us has taken was to lead us to the moment we’re standing in. This was no exception. It took years of turning my attention inward, doing the internal work and learning about psychology and mindset to be aware of why I do the things that I do. Finally, I realized that I had been flying blind – but learned to see what my mind tries to hide, and make better decisions because of it.

The Cliff’s Notes version of what I learned from all of this:

We all live to be validated. If you learn nothing else in the course of your life to help you become a more fulfilled person – this should be it. Every person on Earth seeks to be validated, above all else – their looks, their intelligence, their worth, their perception – they just want confirmation that they are as awesome as they secretly think they are.

We look at a pair of Louboutins and think “I deserve these!!” but if you dig deeper, you don’t have to dig long to see why you want those shoes to grace your feet.

We want that universally recognizable symbol of wealth – that iconic bright red sole. A symbol of the things we all want and envy that are eternally just out of our reach.

We instantly feel worthy, special, and validated when we put them on. When you walk into a room, you let your shoes do the talking – and they are screaming MONEY.

This replaces a missing sense of self-worth with a dopamine hit of validation from envious women as you see them eye your prized possession. You now innately feel that you are worthy to be in that room, and that it’s one less thing you have to prove – so you can breathe a little easier.

The Inner Work to Heal from Money Mistakes

For me, “things” gave me that confidence, whether it was shoes or bags, a new car or perfect manicures. I told myself that I deserved it all, that I would make so much money someday it wouldn’t matter, and that it was important for me to look successful before I really was. All of these may have been true in some way – but it was me lying to myself.

Taking a deep look at why I so desperately needed all of it was hard. It was painful, and brought up issues of self-worth, insecurity, and even the constant mission to overcome stereotypes as a young black woman. I felt it all rush over me every time I walked into a room, like a wave that just kept pushing me under. I was paralyzed by the fear of judgment and nonacceptance – and all the things I bought were my armor against it.

It’s still a process for me, every day. And disclaimer: I still love beautiful things. I still love clothing that looks like an art piece and I still love the craftsmanship and timeless beauty of Chanel.

The difference is that I want them for me. The difference is that I am not digging myself into a black hole of debt to buy them.

Doing the inner work from a deeply honest, humble place to process my money habits gave me the gift of clarity and confidence.… It turns out it works a little better than figuring out how to flash the red heel of your shoes everywhere you go.

How to dig into our money habits, mistakes, and motivations

To truly uncover the roots of our insecurities and deepest beliefs is a continuous journey, but these are a great way to start the process.

  • Pay attention to all the money you spend for the next 7 days. I do mean all of it. Every dollar spent, every automatic draft that hits your accounts, every splurge purchase.
  • Take a moment to notice how it feels as that money exchanges hands. Do you feel pangs of guilt? Worry for the future? Sadness that you now have that $X less in your possession? Joy at what money enabled you to do that day?
  • Journal once a day on all things money – what you bought, where you are at financially big picture, where you thought you would be at this age, and whatever future goals come to mind. Write freely, and let your mind flow from one thought to the next. You might find that you make it as far as reminiscing about your own childhood experiences or the disappointments or pride you’ve felt in what you were able to provide your own children so far.
  • Spend the end of your journaling time practicing gratitude. This part is so important: Feel gratitude for every “mistake” you’ve made, just the same as you would with any triumph. Like we talked about before, every step any of us has taken was to lead us to the moment we’re standing in. Rejoice in where you are at this moment in this beautiful life, and know that tomorrow you will wake up again and continue to learn more about yourself.

As you learn more about who you are and how your mind works, you will see more and more clearly what void you were trying to fill or what hurt you were trying to numb. Above all, you will be able to see what for what it is – a tool and a resource for freedom, safety, and to help make a difference in this world. Nothing more.

I hope your journey with money takes you somewhere beautiful, and that by mastering it you finally welcome true wealth into your life.

Love, as always,


Alaia Sarai
Alaia Sarai

Mother, corporate executive, lover of all things finance and founder of TinyGuru – an education company on a mission to create the next generation of entrepreneurs and innovators.