The Journey So Far

Been talking about work and life. Wanted to present some stages for how this worked for me.

College -> Worked full time while schooling full time. Worked flexible jobs so I could do school. I felt busy (laughable now). Developed several skills for post college career. Helped start a non-profit during this time that I worked in alongside my career for the next 12 years. Got my first 8-5 job 3 days after graduation due to work I was already doing and relationships I had formed.

First 5 years -> Wanted a different career. Was paid low, worked long hours but was non-exempt with an unlimited overtime due to my role. Had to consistently be on-site and thought working remotely was what I wanted. Got next job because of a particular skill and someone I knew.

Next 6 years -> New job, first year I thought this was a stop gap. Turned out I loved the team and stayed for 6 years. Was empowered to help build teams. Was paid better because of the first 5 years pushing myself into expertise in key job functions. Started managing others and realized that leading, coaching, and building teams was a skillset I enjoyed. I also had to be in the office most days and was still learning to love what I was doing. Really enjoying my work kicked in the last few years here. Left here to go work in a global non-profit because of the non-profit work I mentioned back at college stage.

Next 3 years -> Worked at a non-profit overseeing global technology and some security functions around that. I was able to come and go. No requirement of office hours specifically. I realized I liked having an office to go to and also liked the flexibility of not having to go there. Most days I was there and found that was easier. I thought this was my dream job. Turns out getting your dream job in your early 30’s is a bad idea. 2 friends bought 2 businesses and asked me to help merge the thing together. I left to go do that.

Next 5 years -> Worked for some friends helping build out an MSP by integrating 2 together. Learned more skills on business functions and found I like working on the overall operations to make something healthy. Went through my first sell side transaction with a PE backed firm. Stayed on for a few years to help move towards integration and learned about negotiation in a larger org.

Last 2 years -> First job, that didn’t immediately form from a pre-existing relationship. Moved to another PE backed technology firm. Used lessons from the past 2 decades to help grow the firm. Began work to redesign our Professional Services Automation system. Helped with the integration efforts of 4 acquisitions in the first 6 months. Began to learn about building a true 24/7 operating team. Said yes to some things I regret saying yes to. Said no to some things I should have said yes to. Have learned much in the past year.

3 points:
1) Everything you do is training for the next thing you will do.
2) Relationships are key to your growth.
3) It’s a wild ride. Enjoy it.