Why I’m Leaving Oracle

I'm leaving Oracle! Here's how I made that decision and what I plan to do next.

On Friday, March 16th, I'll be leaving my job as a software engineer at Oracle CEGBU in order to try my hand at self employment.

I've been working with Oracle for just over three years now, so moving jobs isn't necessarily a surprising or unusual decision in itself. However, my choice not to immediately start working at another company was difficult for me to make.

I've been researching and planning for this decision for almost a full year, and I have a number of projects lined up that I'll be starting to monetize over the next several months. But I still don't have a everything completely planned out, and I don't know for certain how long it will take for me to turn my projects into a livable income.

When making this decision, there were a few questions I was trying to answer.

Should I leave at all?

I have a number of talented coworkers who have told me that they're content to leverage their programming talents specifically within Oracle. They'll get promoted within the company, or they'll move on to new jobs as opportunities present themselves. But by and large the most exciting things they do will be outside of work via family, friends, and hobbies. Their jobs won't define them as individuals.

I think that's a completely healthy, mature decision to make and I would advise anyone who's evaluating their career goals to put those goals in the perspective of their wider lives.

However my goal since early college has been to be self employed, and over the years I've made a large number of targeted decisions to move closer to that goal — sometimes even at the expense of family, friends, and hobbies. That background made it easier for me to answer the question of why I was leaving Oracle at all. My job was comfortable and I could have stayed for the foreseeable future; maybe even for longer. But that wouldn't have moved me closer to my goals. It was not an option for me to stay put indefinitely.

Is now the right time for me to leave?

I spent a long time thinking about the timing of my decision. Was three years too early? Was there more for me to learn or do within the company? Should I wait until I felt completely sure that I'd be successful when I left?

I enjoyed college, a lot, but it was also an incredibly stressful time for me, in part because of my earlier experiments with entrepreneurship. When I first joined Oracle, the new stability and predictability of my life was almost intoxicating. Suddenly I found myself in an environment where I could sleep in on weekends, visit family members on a whim, and work on personal projects purely because they interested me.

I wanted to time my leave in a way that was responsible, that wouldn't just send me spiralling back into the stress and panic that had characterized my last college year. Since I knew I did plan to eventually leave, the question of time could be rephrased: what would I be accomplishing if I stayed longer?

I narrowed this down to three advantages I felt that Oracle was giving me:

  • technical proficiency/knowledge
  • time (the ability to grow a following slowly outside of work)
  • additional money I could use as a security blanket

I decided that if Oracle was still providing significant gains in any of those areas I would stay and take advantage of them.

Should I wait until I’ve learned more?

I've learned a lot at Oracle, and I'm sure had I chosen to stay I would have learned more. But at this point I'm no longer worried about my ability to teach myself, and I'm no longer worried that I have significant gaps of knowledge in how to build software. I've also gotten over a large portion of my initial doubt about whether I can capably work on large projects.

I decided that while Oracle still had experience and knowledge to offer, I could likely learn faster if I devoted all of my time towards the technologies I was interested in.

Should I wait until my existing projects are more mature?

One of the things I love most about my office's culture is that compared to the majority of Silicon Valley, we encourage a healthy work-life balance. That culture allowed me to do a lot of preparation and engineering work before I started to consider leaving the company.

However, even with the privilege of a solid eight to nine hour workday, it has since become clear to me that my projects outside of work have grown to a state where they need more investment than I'm currently giving them.

To make this decision I reviewed the projects I was most invested in. I realized that many of them were floundering, not because they needed more time to grow but because I wasn't regularly investing enough effort into them to make them grow. Without regular updates or advertising, much of my initial work was going to waste. I reached the conclusion that I wasn't actually gaining any practical time by staying at Oracle.

Should I wait until I’ve saved more money?

Finally, I wanted to make sure I would have enough money to credibly experiment with entrepreneurship, enough to make sure I wouldn't need to immediately start looking for a new job. This was one of the toughest things for me to objectively measure because I just genuinely didn't know how many months I would need. I spent a fair amount of time organizing finances and calculating how much money I spent per month. I also figured out what my biggest expenses were and looked for ways to reduce them.

After a lot of deliberation, research, and online advice I ended up with a number I felt confident about. This number didn't take into account potential revenue, loans, or investments; I considered external funding of any type to be an atypical situation and decided that I would plan to receive none. This number also (quite importantly) didn't take into account any of my long term savings — the assumption being that even if worst came to worst and I couldn't get hired at the end of my experiment, I would be able to continue living for even longer on extended savings; though of course dipping into that money would signify that something had gone terribly, terribly wrong.

Even after I had done this math I kept moving my goalpost. To break that habit I finally had to sit down and rephrase the question in terms of opportunity cost. If I stayed at Oracle for another month, did the additional money give me more opportunity than I would lose via the month itself? I used my current monthly saving rate and current total savings to calculate the delta of extra unemployed time that each additional month of work would give me.

After running those numbers, I decided I had reached a tipping point where the extra money I was getting each month no longer justified the time that I would be losing within a full-time job.

What am I trying to accomplish?

Looking at my work through these lenses caused me to reassess my original goals in leaving. Much of the fear I felt when initially making this decision came down a misguided notion that entrepreneurship is an all-or-nothing venture. Despite my experience in college (which should have cured me of this fallacy), I was still thinking of an entrepreneur as someone who starts one company and then succeeds or fails on that company's merit. I was frightened that in leaving too early, or in leaving while I had any doubts at all, I would somehow be losing my chance to accomplish my goals.

Of course this is nonsense. Entrepreneurship, like any other skill, is learned iteratively. My goal in leaving Oracle is not to immediately become successful, or rich, or to never make a mistake. Rather, my plan is to get better at entrepreneurship by being an entrepreneur.

If I get to the end of this experiment and I haven't built a successful revenue stream then I'll get a job at another company. But I have a while to try things before I have to make that decision, and I've come to realize that now is the proper time for me to try things.

So I'm trying them.