Part one. A Tale of Two Tests.

The first financial test I ever took to get a job was around 15 years ago. Through a very strange series of events, I found myself at a testing center taking the Mortgage Loan Originator test. I was in my mid-twenties and had just bought my first home (for $130,00 with $9,000 down). Up until that point, I had been a trained musical theater performer, worked retail at the Container Store, sold bridal gowns, and started a personal organizing business. What on earth was I doing taking this test!? To compound the anxiety, the specific opportunity that I had been preparing for had essentially crumbled. So there I was, with a random assortment of facts and little hope of even getting to use them. However, the universe decided to universe, and I quickly found myself thrown into the deep end of the mortgage industry for almost five years while also running a profitable Etsy vintage clothing business. Here's a few old photos from those days…

It was hard. I would get literally hundreds of emails a day at all hours. If you’ve ever gone through the home-buying process you know the emotional minefields you have to navigate. This was that on steroids. But experience in that insanity taught me how to read credit reports and tax returns like they were my native language. It taught me how to talk about complex sets of fees and interest rates to people who were nervous and uncomfortable around this stuff. I also could see the reality behind the curtain of people who drove fancy cars but were really just scraping by and buying a fancy house with money from their parents. It was an invaluable experience that I brought to our company when we started it in 2015. 

If I’m honest, I struggle with imposter syndrome a lot and I wanted to prove my legitimacy in the personal finance space, so I eventually went on to pass the Accredited Financial Counseling Exam and the Certified Financial Therapist exam. Even though those boosted my confidence they did not give me state or federal clearance to provide individually specific investment advice completely on my own. Up until then, any investment advice I gave my own clients had to be cleared through Philip as my co-worker and co-owner. I finally realized that I would be forced to hire someone or worse, sell the business, if he died tomorrow. Butt, meet fire. So, I spent the first four months of 2025 studying a 600-page, tiny-font book and cramming waves of questions and YouTubeing every video I could in order to pass the Series 65. And I did. Go me! 

Then, Philip very irritatingly (albeit wisely) suggested I do something even harder and turn right around and attempt the CFP exam. So I whined and moaned for about 10 minutes and, like I tend to do, dove straight into an intensive 10-month course. For context, this usually takes people multiple years to get through. But heck, I figured, just rip the bandaid off, right?

Unfortunately, it was more like pulling out teeth without anesthesia. The CFP exam is a particular beast because it doesn’t just ask you straightforward questions. Similar to the bar exam, it is designed to test your ability to take facts from a variety of different domains and synthesize them into actionable advice. Oh, by the way, a lot of those facts you spend all this time learning can change within the span of a year due to laws. So fun! If you thought I was ready to light capitalism on fire BEFORE… just try finding out all sorts of revolting revelations about the tax code and lack of accountability financial institutions have these days. Tears were cried. Countless hours were spent going into the dusty crevices of financial products, history, and memorizing formula sheets with 18 different Greek letters.

But finally, almost exactly a month ago, after passing seven different individual tests over different domains, I got the privilege of enduring the 7-hour-long final boss exam. I know labors that were shorter and less painful. (Not mine, unfortunately, but they do exist!) There I was, sitting behind the computer screen, body wrecked by hormonal and adrenal overload and “Congratulations, your results indicate a preliminary pass” flashed before me in the tiniest font you can imagine. My body then promptly fell apart.

Which brings me to the second journey and part two which I will share next week…

The Diagnosis.