There Were Losses

Winning! Killin it! The back slaps and shoulder pats abound. Although there has been a push towards transparency in the personal finance blogging space, the overwhelming flow of words and posts is strikingly positive. Peruse the comments of any popular PF blog and it’s easy to feel, how shall I say, inadequate. While I laud the collegial community such optimism has brought about, I sometimes wonder if those that put words on the screen have set impossibly high standards. While I can’t speak for the tone and content of others, I can certainly share my own experiences. There were losses. Big losses. Epic fails and silly dalliances.

I have made several major mistakes in this path to financial independence. The point, of course, is that perfect is the enemy of good and making three rights will eventually take you to the left. You can be flawed and still end up a seven-figure failure like me.

So fellow travelers, let’s take a walk down memory lane and see Doc G at his less than stellar moments.

I think my pride can handle it.

The Fellowship That Never Was

I’m an academic at heart. I love universities, and teaching hospitals, and the pomp and circumstance of didactic learning. When I started my training in Internal Medicine, I began to narrow my career choices among subspecialties. Not only did this fulfill my learning goals, it was by far the more financially prosperous pathway. General doctors do fine, but subspecialty medicine is where the real money is made.

I decided on pulmonary/critical care. This field, I reasoned, would train me to treat the sickest and most in need. I took all the important electives, and secured a glowing letter of recommendation from a well-known expert. I had all the ducks in order.

And then it happened. One fated night in the ICU, a night that still jars me today.

I lost a patient unexpectedly.

I was a second year resident, alone and on call in an empty room full of deathly ill patients. The guilt and sadness were overwhelming.

When the sun rose the next morning, I emerged a different person. It would take years to undo the scars and pain of that single night. I recovered, for the most part. But my dreams of becoming a pulmonary/critical care specialist were gone.

Devastated by what I felt, at the time, was a personal shortcoming, I couldn’t spend the rest of my career locked away in some intensive care unit reliving my past failure.

I pulled every application, tore up my recommendations, and decided to become a generalist instead.

There were losses. Emotional Losses

Investing For Dummies

One day, in 1999, I walked into a Fidelity investment house, threw down a check for $100,000 and waited with a dum grin on my face. The clerk ushered me back to an advisor. He looked like he had just graduated college. He quickly split my money into the greatest expense-ratio bearing, johnny-come-lately, dot-com funds. If the term technology was somewhere in the prospectus, you better believe that I owned it.

The asset allocation was all wrong, the expenses were too high, and when the bubble crashed, I racked up five-figure capital losses. Capital losses that I am still claiming on my tax return today 18 years later.

I put less thought into choosing an investment advisor than I did buying a pair of gym shoes. And I paid for it. I’m still paying for it.

Not my best moment.

There were losses . Financial losses.

Owner of Nothing

I fancy myself a businessman. I take pride in my ability to build and create new ventures. Ultimately, the measure of success of any business is the bottom line. How much did you make? Most of the businesses I have postulated or even tried to build have led to nothing. Zip. Zilch. Zero. Sometimes I even lost money.

A bunch of years ago I started a business providing online advocacy for patients and families undergoing medical crises. I spent five thousand dollars to hire a designer and create a web site. I spent time and money marketing the idea, man hours applying for medical licenses in other states, and cash working with a lawyer.

Six months later, I had a brilliant idea, a beautiful website, and not a single customer. My venture failed. Spectacularly. My lack of success wasn’t do to the product, or even the market. It was my fault. I couldn’t covert my ideas into a rational game plan.

There were losses. Losses of pride.

In Conclusion

I want to make this clear to anyone who has been kind enough to grace this blog. When I write about my success in investing, real estate, or business, realize that I am celebrating the wins. There were losses too.

Losses that I regret from time to time.

Losses that were necessary.