The Challenge of Making Tough Decisions


In 2008 I was working as a financial advisor in Chicago for a large insurance company. The job was 100% commission-based and I was responsible for paying for absolutely all of my expenses. The company didn’t provide anything to its advisors, not even basic necessities like printing paper or paperclips. I was 27 years old at the time and enjoyed what I was doing. On average, I was bringing in roughly 5 or 6 new clients a month and quickly became a rising star in the company.

Nine months after starting at the company, I became overwhelmed with the quantity of work involved with servicing almost 70 individual clients. I reasoned that if I continued bringing in new clients at such a fast rate, then I would need to hire help. So I put together a job description, posted it on Craiglist, and began setting up interviews. I think I interviewed 5 or so candidates before hiring someone that was truly a rockstar.

I had never hired my own full-time employee before, so I spent the first several weeks trying to adjust to being a boss and helping her get up to speed on things. At the same time, I still had my job to do, which primarily consisted of meeting with existing clients and prospecting for new ones. Sure, we provided sound financial planning to our clients, but at the end of the day we had a heavy sales mandate that was necessary to our survival. Once we found a good working rhythm, the business took off and performed financially well. In fact, things were going so well that I upgraded to a corner office and my wife and I bought a house in the Chicago suburbs. We were living “the dream.”

And then reality struck. It was post 2008 and the economy was caught in the wake of the destructive effects of the mortgage crisis and people were tightening their purse strings. It became increasingly challenging to bring on new clients, let alone hold on to existing ones. It seemed like everything I had worked so hard to build was slowly slipping from through my fingers. To keep things afloat I had to take out a line of credit to pay my staff, purchase supplies, and pay office rent. The worst and probably most devastating part of this process was the day I made the decision to let my assistant go. I remember lying in bed the night before thinking through how I was going to do it, what I’d say, how she’d respond, and how we’d deal with it in the moment. Even though I knew I had to do it to protect the livelihood of my family, it was extremely difficult to process the fact that the decision I was going to make would negatively impact the life of someone else.

The following morning I hopped on the subway to work and sat there quietly, mentally preparing myself for the impending conversation I was about to have with my assistant. As I rode the elevator up to my office I decided the first thing I was going to do was call my assistant into my office and tell her that I had to let her go. Thinking back on it, I have no idea if she may have known in advance that I may be letting her go. But given the circumstances and the fact that we never held unscheduled, early morning meetings, maybe she knew something was amiss.

As soon as we sat down I could tell by the look on her face that whatever I was about to say was not going to be good. I started by describing the situation and what was happening financially with the business. I probably didn’t need to go into as much detail as I did, but I felt I owed it to her to over-explain things so she didn’t think I was letting her go because of anything she was doing and that it was something I had to do because of the financial situation the business was in. It was an emotional conversation that was every bit as hard as I thought it would be. It’s extremely tough to let someone go that you actually enjoy working with. If you don’t know what it feels like to go through and experience like this, try to imagine the feeling of happiness and jubilation you feel when someone you despise leaves a company, and then think of the opposite of that emotion. It’d kind of feels like that.

I’m in the process of reading Principles by Ray Dalio and in one passage of the book he said something to the effect of “energy can never be destroyed, it can only be reconfigured.” He was describing this in the context of how people, animals, processes, etc, evolve and that through each cycle of evolution, things become better, knowledge is transferred, and as a result society benefits as a whole. As I thought about this, I began to think about this principle and how it relates in terms of money (or value). One might say that money or value can never be destroyed; it can only be reconfigured or transferred from one party to the next.

When you think about the transfer of goods, services or money, someone in the process benefits, even when things go poorly for one party or the other. I started to think about this in regard to my former assistant. Yes, it was a tough financial situation for me at the micro-level, but at a macro-level, financial resources were transferred from me to her, and as a result, there was a positive financial impact made in her life during the time we worked together

I think it’s important for each of us to understand how the decisions we make, whether good or bad, impact the lives of others, and even more so, society as a whole. Even when we fail we can still positively impact the world through our efforts. It’s easier to adopt this frame of mind when we think about society at the macro level instead of focusing on the micro issues that only affect us individually. Cheers – KM

Photo by Nadine Shaabana on Unsplash


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