Dr. John has primarily been in the right place at the right time. He was employed by a stable private company that distributed stock options. When they went public, he realized a windfall. He also bought Apple shares in the late 90s and sold some in 2020, which turned out to be a lucrative decision.
Regarding the work, Dr. John brings a unique joy to his work environment. He considers himself a bit of a Dilbert in his team, striving to leave people smiling after their interactions. The time he spends on administrative tasks is something he considers tolerable.
Dr. John devotes himself to mentoring and forging relationships with the new generation of professionals as his contemporaries retire or pass away. In his personal time, he’s a part of an advisory committee for a local university and the maintenance team for their local rails-to-trails organization.
The friends he has from his running/biking community and his social circles are another source of engagement. Notably, he meets up regularly with his oldest friend, a bond that traces back to their childhood.
When it comes to his concept of “fun”, it’s closely tied to his professional activities. When he’s solving problems at work, that’s when he finds himself truly enjoying the moment. Trying to seek out traditional forms of “fun” often leaves him asking “Am I having fun yet?”
His perception is that the grass is not always greener on the other side, and he has openly shared this perspective in his writing. However, he admits to being a workaholic, despite having a strong focus on his family and friends.
As for his investment strategy, it’s built on the simple principles of “be lucky and don’t do anything stupid.” This has, over time, proved fruitful and facilitated his financial success.