Knowing When It’s Time to Move On
2 September, 2021

VP, Software Engineering at Oracle
Problem
The first time that I ever moved from one company to another was after fourteen years of service. This was at Microsoft, so, naturally, deciding to leave was a very difficult conclusion to come to. I was in a great company and part of a great team led by excellent management. To look at all of these factors and decide to try something new is more than many people can handle.
Knowing when something in your career needs to change can be an unsettling feeling. I was so at home during my time with Microsoft; my commute was short, and my schedule was flexible around the needs of my family. Everybody knew who I was and what I did.
To go from this very comfortable routine to reestablishing myself in a brand new company took a lot of courage, but I would not be who I am currently if I had not stepped up to the plate.
Actions taken
At Microsoft, I knew our work inside and out; there were no more questions left to answer. I was able to solve the types of problems that we were working with quickly and easily. This was the catalyst --- I was doing no new research and my growth had stagnated. I was so used to everything: the people, the product, our services, our customers, all of these factors were known. There was nothing to explore.
I realized that I could probably work here for the rest of my life without ever being required to learn another new thing. Suddenly, I felt myself taken by the urge to try something new and to push my way out of the box that I was in.
I will emphasize this again: this change in company was not necessary. I did not need to do it. I had to rouse myself from what I was used to in order to elevate myself as a professional. I wanted to stretch myself with new people in a new company. I was hungry to learn; I wanted to find an organization where I would not immediately know all of the answers.
I picked peoples’ brains, especially a few of my mentors. I looked into other companies and industries on my own time, as well. The prospect of doing something completely from scratch excited me greatly. I was very active in the work that I was doing for Microsoft, but none of those ideas were nascent or of my own proprietary design.
I had initially really wanted to join a start-up, somewhere where things were not quite settled yet. This would give me the opportunity to leave my own signature on what we would eventually accomplish. Joining a start-up with a family to support, however, is very risky; I was not interested in climbing aboard a sinking ship.
The department that I joined within the company was still able to provide the experience that I was seeking, however — my team was a totally new part of the company, one that I would be able to influence the success of deeply. The course ahead was still completely uncharted, which was what I was after. I heard about this opportunity in this brand new team from someone in my old network. This person I trusted worked at this place, which made my decision to choose between offers easier.
I worked on my first product within the company for the first ten months, launching its first version. I was able to take the idea from inception to release with a team that valued Agility. I loved it.
Toward the end of the release cycle, however, something happened way above me. Things changed, and these changes were not in alignment with my vision for the work at hand. I was in middle management by this time. I had many opinions and thoughts on where the product and service should go, but the direction that they wanted to take things in was out of my control.
I was not as passionate about the new destination that had been set for us. I had never made a move like this in my career before. Yet, here we were, less than a year in, staring into this new objective that I didn’t believe in. My potential for growth in the position had, unfortunately, been curtailed. I found myself compelled to move once more, but this time was for a very different reason.
I was lucky enough to land into the team that I currently work with. We’ve all grown so much since I started. It has been such a fulfilling experience.
Lessons learned
- If you’re bored, chances are, it’s time for you to move on. At Microsoft, I knew our business and needs so well that I was able to meet those expectations in my sleep. The feeling may be hard to place; all that you’ll really know is that something is not working anymore. It doesn’t have to be the team or any of the people. You simply feel in your heart that there is somewhere else that you should be.
- You need work that excites you, something that you look forward to doing every day. When that excitement changes, it’s time to look around. Acknowledging this feeling is the first step that you need to take.
- I have enjoyed a long and successful career already, but I still feel the need to learn new things whenever possible. Without the courage to jump into the deep end, I would still be at Microsoft, going through the motions.
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