top of page

How I Overcame The Fear Of Going Broke

There are people who know from an early age what they want to do with their life. They know they want to be a doctor, or a baseball player or an entrepreneur. I wasn’t one of them. I never had a childhood realization that I wanted to own a financial planning firm. As a kid, I didn’t even know people made plans around money. In my house money seemed to come and go; sometimes there was enough and sometimes there wasn’t. In fact, I didn’t learn what financial planning was until just after college when I happened to take a temporary position filling in for an administrative assistant at a wealth management firm.

What was supposed to be a three-month role turned into nine years of working my up, going from the person who picked up lunch for the shareholders to eventually being offered a seat at their table. I remember those early days when I got my first glimpse of what financial success looked like. I wasn’t anywhere near it, so I threw myself into learning as much as I could, getting my CFP® and my master’s degree in financial planning while learning from some truly incredible mentors.

As time went on, I started learning more about my field from sources outside my firm. The conferences I attended and the professionals I met exposed me to new ideas and what I believed about my work started to diverge from what I’d been taught. While some viewed the “emotional stuff” as tangential, for me there was no denying that how we feel about money impacts what we do with it. While some wanted to focus on widening the reach of the firm to more and more clients, I was drawn toward fewer and deeper relationships.

For the first time, I started to consider leaving my job, but it felt risky. I knew that if I stayed, I would become a partner within a year and that I would undoubtedly have a financially successful life. The part of me that came from financial insecurity and that highly valued peace of mind around money questioned if I could give all that up to pursue work that felt more authentic to me. I wondered if giving up something good to chase something great was indulgent or brave. It took a lot of time thinking, laying on the floor of my bedroom listening to Mumford and Sons (my go-to music when life gets confusing), to make the decision to leave. It was my first step out of comfort and safety into the unknown.

I joined a new firm in hopes that it would be a happily-ever-after kind of match. It turned out to be more of a Goldilocks scenario; the first place I worked had been too hot and the second place was too cold. This time, though, it took me years to acknowledge that it wasn’t a fit. Things were so good financially that I ignored the voice in the back of my mind saying, “start your own company”. If leaving the comfort of my first firm was nerve wracking, the idea of giving up what had become a very cushy life felt absolutely insane. Nausea would set in whenever I would think about the unpredictability of self-employment, but try as I might, I couldn’t silence the stubborn voice telling me to try this on my own.

That’s when the very work I pursued became the solution to my problem. I had immersed myself in how emotions impact financial decisions so I knew a fear strong enough to make me physically sick was a sign of a financial flashpoint, an event or set of events in our life that stick with us, usually because they are painful and because they taught us a lesson that we never want to forget. They are the experiences that cause us to make promises to ourselves like “I’ll never let that happen again” or “I’ll never be like that”. The promise I had made to myself is that I would never let myself go back to living hand-to-mouth and worrying about every dollar I spent.

Keeping this promise was so important that I made life decisions to accommodate it. It was like a litmus test; if something might lead me back to financial insecurity, I wouldn’t even entertain the idea no matter how much I wanted it. It’s why I was reflexively (and subconsciously) saying N-O to the idea of starting a business, so much so that I wouldn’t even run the numbers or spend any real time thinking about anything other than what could go wrong.

To give this path fair consideration, I had to find a way to think about it without being overcome by angst. So, I did a little exposure therapy by forcing myself to think about starting a business in increasingly frequent and longer doses by listening to podcasts, talking to friends, reading articles and journaling. The more I thought about it, the less I was gripped by fear and the more I could acknowledge there were both pros and cons to self-employment. Lo and behold, there was an upside I had largely been ignoring.

From there, I used my practical financial planning skills to examine what was financially feasible. I considered how different scenarios would impact my life. Once I was emotionally able to take in the information, I realized I could follow the little voice in the back of my head without breaking the promise I made to myself. The path I wanted to follow didn’t immediately lead to financial ruin as I had been sure it would. With my feelings under control and my mistaken beliefs dispelled, I was finally free to make the leap.

What I’ve come to learn is that we don’t make decisions based on financial reality. We make decisions based on our perception of reality which is highly informed by what we’ve been through in our past. The challenge is not letting our past get in the way of our future.

46 views0 comments

Recent Posts

See All


bottom of page