On Being a Serial Obsessor

I have been called a “serial entrepreneur.” I have recently been describing myself as “an entrepreneur turned investor.” This morning, I read a descriptive phrase that better fits the present phase of my life and doesn’t negate my historical experience. I am a “serial obsessor.”

I am a serial obsessor. I have recently been obsessed with centralized operating system designs that allow a decentralized management ethos to endure throughout the scale-up phase and beyond the maturation of a large company. That is a mouthful. We, at Little Engine Ventures, are coming out of the launch phase and making our transition into the orbit of our mission, which is –and has been since launch– to help people in our communities climb.

I have several other examples of serial obsession that fractal down throughout my days, from my youth and through this morning. I share these experiences and self-assessments not to brag –I’ve committed plenty of sins against God and man– but rather to clarify my own thinking and aid the fellow business owners that might resonate with my experience of obsession… and perhaps help those with a range of interests apply them into something of value for those whom they love.

A serial obsessor goes deeper than normal. They become obsessed. They become fanatical. When an expert says a thing works this way or that way, the fanatic takes note, and then goes and checks their references. The fanatic reads the references that inspired those references. They go deep. The obsessor often receives negative connotations from the super majority. They are weirdos. Sometimes they are “specialists” and known for and admired for their excellence in this or that subject matter. These heroes of specialization know their one thing extremely well. They are best-in-class and have the empirical data to back it up. And, they may be obsessed. An obsessed specialist is good. And if the area of specialization is well-timed, they can become world-renowned, and well-compensated for it. If ill-timed, the recognition may happen after their death.

The serial obsessor differs from the specialist. They go about life in series, or phases. They appear to transform. That is, after they plumb the depths of a subject and acquire mastery, they move on. Many specialists go deep, and then dwell in the bottom of that well. Some of the best come to the surface and guide others in spelunking adventures into their cavern. Most become Gallum-like, hunkered over their precious. A few, well-timed, well-valued specialists are handsomely rewarded as others pay to admire their excellency, or benefit from their well-honed talents. The serial obsessor returns to the surface, skips along the surface, enjoying the sunshine and finds themselves chasing a butterfly into another area. Once sufficiently curious they begin to dig another pit. Hit rock. Blast. Go deeper.Find a cave. Wonder further. And form a new obsession.

The distinction between a jack-of-all-trades and a serial obsessor is the positive attributes of their type of range. The jack-of-all and master-of-none type stops too early. They do not go to the point of excellence and/or what I would call, “weirdo-depth.” I too am guilty of this. I read Einstein’s “Theory of Relativity” and felt good about myself… and stopped there. I thought well of myself but did I know everything about this area of science? No. What I may have gained –that someone else has not– was gleaned not by reading just this one book, but by reading widely, and concentrating my area of study to the greats. By this method, I gained the architecture of great books. And, in turn, have an undestanding of what it traits are often shared by great men. Einstein is Einstein because of how well he communicated. Great minds are evidenced by clear writing. They make their work approachable. Don’t believe me? Read it for yourself. Read lots of great books. You will come to agree… or you will be wrong.

The person of depth goes much further on the subject line. And each person’s “line” of digging varies in their starting point, their direction of travel, and the order of operation. A common trait however, is that the obsessed read and journal. They build models and read whitepapers. They talk to others about their findings and seek guidance from other experts in the field. They use the guidance but form opinions as their understanding improves. They often engage their physical resources, too. They put assets (beyond their time) at the risk of loss based upon their findings. By this, they also learn from experience. They test and modify and retest and learn from and move onward and inward and deeper and deeper. Business owners get this. If the individual started their company as a technical expert, they probably went to the bottom of that area, and then pushed harder and further than their peers. They became someone worthy of being followed. People joined them. They kept going and learned ways to pull together neighboring skills to round out their understanding and fit together plans for their stakeholders in novel ways. The successful businessmen among us have always done this. They bring together some diverse combinations in unique ways. And they adapt quickly to their environment because they have mastery of their domains. They go to the point of becoming creators within that field.

A serial obsessor does likewise. But, there are finite limits to the number of fields one can master. There are limits to what can be covered in a single lifetime. The choices of which areas to pursue becomes an important decision. And the intensity of one’s focus becomes the most important element when time is finite. Choices must be made. And, while chance conditions shape the outcome –because the quality of choice is not knowable at the beginning– good judgment must be an ongoing pursuit. Update your prior assumptions. Commit to moving forward, always.

In our society, a specialist can make an attractive living being employed as the best-in-class. A super-specialist might even become the employer of a group of specialists. However, a serial obsessor can own the systems of multiple, best-in-niche enterprises, and modify them with the help of his teammates. He can also become known as a lunatic. Trust me, I’ve pushed the herd on this edge.

Psychosis is the detachment of thought and emotion from reality. One becomes unhinged. Someone who chases butterflies without purpose is crazy. They have uncontrollable impulses. The Gollum specialist is also detached from the beauty of life. It’s why it’s so sad and creepy. Don’t be Gollum-like.

Be a serial obsessor with cognitive powers over where you obsess. Be selective. Fill your life with purpose. Seek mutual benefit. Parlay your talents. Share them with others.

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