My last entry was almost 6 months ago. There’s been no lack of thoughts or ideas. No lack of motivation to continue understanding what’s happening around me. But there was a deep sense that I wasn’t at my best self and that this was an activity which I would only do when I could put quality work forward.

Generally speaking, writing these entries is a weekend activity for me. I’ll wake up, go through my morning routine, and then sit down with my laptop and write out something that’s on my mind. It was common to start at 9 or 10 in the morning and not wrap up until the mid-afternoon. I found it really valuable in organizing and testing my ideas. I also really enjoyed the exercise of articulating my thoughts.

But… As my professional life continued to go sideways, so did the rest of my life. The more I think about it, the further back it probably goes.

Chapter 1

I was all but kicked out of my university half way through my second year. My grades were decent, but in my position as dorm president, I had a habit of standing up to university authority when they overstepped their boundaries and started negatively impacting the lives of students. Through a series of university judicial charges, bans, and fines, they made it very clear that I was unwanted at that school. So I left. But after 18 months, I took it as a personal challenge and decided to go back and take my degree through sheer academic effort. I did. I excelled and it left me optimistic for a bright future where talent, effort and focus would lead to great things. I even skipped my convocation to hit the job market ahead of everyone else. I managed to graduate into the great recession. The job market was barren. I took what I could get.. I was hired as a management trainee for enterprise rentacar doing customer service and washing cars in a suit for $13/hour. In one of the world’s most expensive cities. Not ideal, but if I could make manager, everything would get better.

Chapter 2

Enterprise Rentacar was hemorrhaging money in my area so they decided to cut costs. Within 12 months, most of the area’s top paid employees were constructively dismissed. That included my manager, also a close friend of mine.. In that transition, I was offered a job managing the second largest location in our group, a mid-sized airport branch. It required me to move about 4 hours away and I wouldn’t get my promotion until I arrived, but they insisted I would be rewarded by taking one for the team. I discussed it with my dad, and we decided it was the best career move available to me. 2 months after I moved, my dad died.

Chapter 3

Within the month following my dad, my girlfriend left me for another guy, I tore my shoulder pretty bad, and corporate management was now telling me that I would have the responsibility of a manager, but only the title, pay, and recognition of an assistant manager. They said that corporate policy prevented them from authorizing a promotion at this time. 2 months later, they moved another assistant manager to the branch who was under the impression that they would get promoted. 2 months after that, the original manager who was on an indefinite maternity leave decided to come back.

Chapter 4

Without much going right in my life, I put all my focus towards the small inheritance my dad left to his 3 kids. My dad made it my responsibility, so it became the most important thing in the world to me. As I started to look for work, the investment firm who handled my dad’s funds took an interest in me. So did a wealthy business man who was looking for a protege to mentor as he shifted into a soft retirement. The portfolio which my dad made me responsible for is probably the single biggest reason why I chose the bank.

Chapter 5

The bank (RBC) was introduced to me as the hardest thing I’ll ever do, but that if I can make it through the first 4 years, it’s worth every ounce of effort. I was warned about the high failure rate, but was also told that failure was a result of laziness, ego, and not following direction. Little did I know, the failure rate was about 95% for those who didn’t arrive with an already established book or source of clients. I also learned that following the process meant maintaining a status quo which was ineffective, severely out of date, and not in the clients’ or public’s best interest. Regardless, I worked harder than I had ever worked before. Weekends was a given.. late nights were a given.. holidays were a thing of the past.. whatever I could do to increase my chances of success. It didn’t seem to matter though. Expectations were $10M of net-new assets per year, by far the highest in the industry. In year one, I did $7M. In year 2, I was up to $16M. By year 3, management had determined that I wasn’t worth keeping. In year 4, I realized that a far better path was joining a more senior team who wasn’t subject to short-term sales targets and could actually focus on providing wealth management services to their clients.. what I understood the job to be, and what I excelled at. After a great deal of effort, I joined a top 5 team with expectations of taking over the book once the senior advisor retired in 5-10 years. It was the best possible deal someone like myself could’ve landed. 1 month after I moved and joined the new team, the senior advisor told me that management had a target on my back. A month after that, I was fired.

Chapter 6

I left the bank on a Monday and while leaving the office, my stubbornness and sense of competition took over. I refused to be beat and committed myself to having a new job by Friday. Then I went and bought an ounce of weed.. mulled it over.. and realized that was a terrible idea. For the first time in my life, I had committed everything I had to being successful at something – and it failed in spectacular fashion. All the hours I put in.. all the money I spent.. all the relationships I didn’t prioritize.. all for naught. I used to think that I was so capable, that I could be successful in any environment. This proved otherwise and it was important to understand why. Eventually, I realized that if I was going to stick to my values and be a person of integrity, there were some environments which would tolerate me and some who would celebrate me. It was now my responsibility to find the latter.

Chapter 7

I eventually found work with a small cannabis shop which had won a series of awards for being the best retailer around. With cannabis legalization on the horizon, it occurred to me that there was a significant amount of opportunity here. At first, I worked with them in building an expansion plan which would see them go from one store to a national chain. Then we needed to raise capital, so I put that together too. Eventually, I told the company I was looking to earn a leadership role within the company, preferably the CEO seat. The founders were a husband and wife team who spent most of their time minding the store or doing non-profit work, creating a great opportunity for someone to come in and mind the back-end of the business. For the first several months, everything was pretty good. The happiest I’ve been in a long time was when we had 45 days to prepare for a pitch competition. I worked 15 hours a day, 7 days a week to make sure that every aspect of the business was presentable to investors. I even stopped smoking weed because it was just getting in the way of something I loved doing.

But then legalization was delayed and regulations became uncertain. This spooked investors and a lack of investors stressed out the founders. I tried to tell them that we didn’t need the majority of funds until after legalization and that they didn’t need to stress, but it fell on deaf ears. I tried to bring a business coach in to help streamline communication and roles. They suggested that we design our roles around our personal interests, skills, and capacity. That meant giving me more of a leadership role in the company. They were reluctant and the recommendations went nowhere.

As we got closer to legalization, I lined up a friendly investment from the largest cannabis company in the world. It was all the financing the company would need to build out its next 8 stores. Around this time, the founders started to question what I did for the company or if I was even needed. I had the distinct impression that I was no longer part of the inner-circle. Maybe this had something to do with their passion for social justice and the fact that I’m a straight white male who drives an SUV and used to work at the bank. Maybe it was their suspicion for my rational approach to business when everything in their world was a matter of emotions. Maybe it was their tendency to look at the business as their property instead of looking at it as an organization of people who are working together, trying to solve a problem. Or maybe it was me declining to start our meeting with healing crystals for the second time in 2 weeks.

Whatever it was, they came to me and said that they wanted to enjoy themselves when they came to work and they were spending most of their time stressed out. They thought I was the cause. Apparently, I just wasn’t their kind of people. I listened, I apologized, and I made a real effort to try and ‘soften’ my edges. This included spending a long weekend at a ranch, doing mushrooms for the first time as an adult, talking to my ‘softer’ friends, and reading up on the issues I was facing. It wasn’t enough. Within a couple months, I was no longer employed. They even tried to remove me from the board, but had to stop when they were reminded that all the funding came through me and is only accessible while I”m part of the company.

Chapter 8

This lands us at Dec 1 of 2018. Just like when I had left RBC… personally broke.. somewhat dejected.. but with my eyes on redemption. I was a major part of building one of the best cannabis retailer in the country. On the verge of cannabis legalization, this seemed like a rather valuable skill set. Things could be worse.

Something I had finally learned is that I’m not willing to compromise my values for my career, so finding a place where there’s an alignment of values is paramount. As such, I thought I’d take some time in finding that fit this time around. Between December ’18 and April of ’19, I applied to over 200 jobs, participated in dozens of phone interviews and several in-person interviews. That was on top of all my warm-network activity. By the end of it, I had been considered for everything from Chief of Staff at a publicly traded company to a Chief Operating Officer of a small start-up.

It was quite the experience. I learned about the gig-economy and how health plans, let alone dental is getting harder and harder to come by. I learned about how recruiters are incentivized. I learned how the head of HR is there to sell strong candidates on the company in the same way that strong candidates try to sell themselves. And I definitely learned about the imbalance of power between the interests of those looking for work versus those looking to hire. I didn’t take a job until April 15th of this year. Not because I was being picky, but because it was the first job officially offered to me and I needed an income.

Chapter 9

The job that I ended up taking was with a cannabis retailer that I had been trying to stay away from. I didn’t agree with the way the CEO carried himself and was not interested in his business. However, they were the only company who made a real offer. Even if it was only a 3 month contract, the compensation was fair and it was an industry I wanted to continue in. Could be worse.

I was brought in to help with a capital raise and do some market analysis. We launched the raise a couple weeks in and I quickly found out that current shareholders, who we were going back to for more money, were not very happy with how things had gone. As it turns out, the company had raised $8M to open 15 stores by the end of 2018. Now in 2019, we had 2 stores, no money, and needed another $6M to open up another 9 locations. The capital raise fell flat on its face as almost every existing investor declined to put more money in. As a result, the CFO I was working for became increasingly agitated. Eventually, he asked me to mislead potential investors for the sake of closing more investment dollars. I told him it wasn’t a good idea and stood my ground on ethics and business practices. The following week, I was told that if I wasn’t comfortable doing these kinds of things, my contract wouldn’t be extended. I brought this to the CEO and HR who both sided with me, but ultimately said that they weren’t part of the conversation and would have to talk to the CFO as well. The CFO met with me the following week and told me that the unsuccessful capital raise has forced him to re-do the budget and they no longer have funds for my position. That was 4 days before my contract ended.

Chapter 10

For the fourth time in my young career, I had found another employer who was at odds with my values. The realization that I was consistently being forced to choose between my values or my career… was just a really dark place for me. My values are who I am. If I compromised those for someone else, in exchange for money… I just can’t. I’d rather get off the ride entirely than live my life like that.

Upon reflection, it’s like I had the potential to be a tremendous employee.. but despite my best efforts, couldn’t find the right employer. I had the potential to be a great entrepreneur but lacked the resources to do it. It was like I had all these gifts.. but no one to give them to. All this potential, but without purpose. And if I’m not useful.. if I’m not meaningful.. if I have no purpose.. why am I needed? Why should I continue to consume the world’s resources if it’s all for naught? Wouldn’t it be better for everyone if I just removed myself from the equation?

I don’t think I’m the first one to have those thoughts. I suspect they’re more common today than ever before. And for those reasons, I’m grateful for the experience. I’m not out of the woods yet, but I’m no longer missing the forest for the trees. It’s remarkable how much you can learn in the dark places of your mind, especially once you shine some light. Even if I were to get hit by a bus tomorrow, the compassion I’ve learned for my fellow human being has made this entire experience worth it.