Where do you want to be in 20 years?

I haven't updated for a while but rest assure, I am keeping busy being retired. One of the things I have been doing is mentoring some less experienced people in job-searching. I have a couple of friends who are recent graduates of respectable schools but lack real-world experience. I thought this was a perfect opportunity to strengthen my network. Others have done it for me and its just good karma to pay it forward.

So I would like to think of myself as a decent-to-good interviewer and working in the industry has given me some insight on what people look for. There was even a stretch of time at my old company when we were on a hiring spree and I averaged 6 interviews a week. One of the commonly asked things, especially for entry-level positions is as follows: "Where do you want to be in 5, 10, or 20 years?" Now back in the day, I had a nice old canned-response answer that showed I was ambitious and organized which usually got me the job. I told my friends whom I was helping with interviewing that this question is just a good question to know an answer to, not just for interviews, but to plan out your career path. However, my friends who know my current situation with this retirement thing, asked me to answer that same question now.

Hmm. That's a good question. What is my "career path" in retirement and where do I see myself in 20 years? Typically, people make their 20-year plan their dream, while their 2-5 year plan the stepping stones they take to achieve that dream. For example, if you wanted to make a lot of money without doing a lot of work, you would probably want to find and stick to a job at a large company that is stable and structured and can afford to pay you very well for doing one thing. If you wanted to one day own your business, you would probably have to go to a top-school MBA program, do an internship, and network in the industry that you want to move in.

This question became a little trickier for someone in my position because I am doing something that is outside the conventional box of thinking. I've realized that a lot of these plans are made so that people can organize and predict the future. They have a goal of a family and a profession at an early age and they spend all their time trying to achieve that. Once they do, they are happy with their daily routine: drive the kids to school, working 8-5, coming home and spending time with the family in their white-picket fence houses in the suburbs. I respect that - it is such a simple path to contentment and there is a lot of reward if successfully done.

However, that's just not me. I feel that my privileged life (and being young and an idealist and living in San Francisco and many many other factors) has built a level of complexity that makes answering this question not that easy. I feel for someone like me, dreams can change, and they change fast.

One great personal example is my choice of major in college. I liked video games in highschool. I said, hey - maybe I want to make video games as a career so I went to college and got a Computer Science and Engineering degree. Then, I grew up. However, I was in too deep and even though I was able to get a good job doing my highschool dream, it definitely showed me that my personal goals can change. Whatever I do now will cause a ripple effect for my future and I should have a plan that can compensate with changing life goals. Many would say that highschool and college is a time to explore and find out what you want to do and I feel this is true. I am taking it one step further - I feel that all of life is a time to explore and find out what you want to do. And I'm doing just that.

While most people see an unknown future as a scary thing, I see it as an adventure. Almost all past events in which I did not have concrete foreknowledge of, ended up being some of the best times of my life. Some people like a vacation tourist package. I like to just buy a plane ticket, hop on a plane, land, and then figure it out. Having the skills to be able to adjust to adversity seems much more useful and realistic than having the skills to plan for a future that has an infinite amount of possibilities.

Question. (Dwight from the Office reference) "Where do you see yourself in 20 years? What are you doing right now to get there?"
Answer. I don't know - and I'm doing exactly what I'm suppose to be doing to get there. Exploring, learning, adjusting, and reacting.

....or maybe I'm just trying to cope with a QLC.