In this episode, Dave and Jamison answer these questions:

1. I work at a growing start up, and while I was hired as a web dev, I have started working on unrelated but cutting-edge tech for the company during off hours. My boss has encouraged me to do this with monetary and office life bonuses, and he has reworked our business model to focus on it. The only problem is that our CEO overpromises and pushes me to my mental and physical limits for very short turnarounds. I still have to do my regular job. While I love the challenge, and love the company, I feel set up to fail. And the 40 hour coding sprints over the weekend are killing me. I feel like I’m setting a horrible precedent because somehow, defying all logic, I’ve met the deadline each time. How far is too far? Should I keep killing myself, or take the agony of defeat on a project.

2. I’m currently working as a Senior Solutions Architect after a career progression that looks like this: Junior Developer, Intermediate Developer, Senior Developer, Junior Architect, Intermediate Architect, Senior Architect.

   In a recent one-on-one with my boss, we were discussing my future career options and concluded that the next step for me would be one of the following three positions: VP of Engineering, Chief Architect, or CTO. According to him, all three have similar levels of prestige, pay and influence, but vary in the nature of the job.

   Reflecting on this conversation, it dawned on me that I’m close to the final stage of my career. I’m currently 39 years old, so I’m now thinking to myself: Is that really it? One more promotion and I’ve successfully climbed the corporate ladder? End of the line. Time to retire. Nothing more to strive for (other than working on the most interesting projects).

   So, could you please talk about the software career progression, what to aspire to and how to measure one’s own progress once one has reached the top of the ladder?