The hardest questions to answer are the ones about ourselves.
When I was having my quarter-life crisis at the grand age of twenty-eight, I started looking for an answer to this all-important question: What Do I Really Want to Do with My Life? The answer to this probably changes depending on my age. But I knew if anyone asked me on the spot, I would have no answer. I couldn't live with not having at least one answer to this question.
After all, shouldn't this be pretty easy? If you ask me what I want for dinner tonight, I can tell you in less than two seconds (the answer is Pad See Ew). If you ask me what I want to do tomorrow, this Friday night, or on my next trip aboard, I can give you an answer without much hesitation. But when you extend the timeline to an extreme - a Lifetime, it suddenly becomes an almost impossible question to answer. The risk of giving a wrong answer becomes much bigger when the time is extended. Spending Friday night at a boring event would only cost me a couple hours and I can easily recover next day/week, but when it comes to a lifetime - I risk steering my life in the wrong direction!
Another problem with trying to answer this question is, where do you start? How do you know the logic and reasons you've given yourself to answer this question now will still hold truth later? How do you know the choice you make now, which presumably you based your decision on making your future self happy, will satisfy all the needs and desires you'll actually have in the future?
The fact is, we can never know for sure. (read more about this topic on Stumbling on Happiness) But that doesn't mean we shouldn't try. So I dreamed about doing different things, being different people, and having other's lives. As you can probably have guessed, day-dreaming and imagining didn't really resolve anything for me. It felt too ... unreal. I needed something more concrete if I were to buy a one-way ticket to my life's journey.
Then I draw inspiration from one rather mundane event that happened during that time - a performance review. Not unlike many other companies in the US, Sony in Japan also had performance reviews every six months. Since I was interviewed by my direct superior who I'd worked with closely every single day and knew me inside out, the review process was more or less just a formality. However, one question from the review stood out and lingered in my head days after.
Where do you see yourself in 5 years?
Such a simple question, and yet it puts me in the right frame of mind. If I know what it feels like in 5 years of time to be at a certain position, I can at least have a pretty good guess if I will like it or not!
So not unlike the performance review, I gave myself an interview.
I pretended to be a journalist for a major magazine, and interviewed my future self in 5 years in different roles that I think I'd like to be in - as a full-time writer, a founder of a software company, a founder of a game studio...etc.
I started with simple questions like, "What is the name of the company" "What is the title of your first novel?" to more specific questions like, "What projects are you working on?" "Who inspired your products / your style?" "How many people are in the company?" "What does your office look like?".
Then I wrote down all the questions in as much detail as I could imagine, pretending that I were in those particular positions - as an established writer, a CEO of a software company, a core member at a game studio. The more questions I answered, the more words I put down, the more I felt like I was that person.
I experienced what it was like to be that future me. I learned quickly if I will be happy being that particular person.
That's when I decided I am going to start a creative studio, with a small team, flexible location, and focus on independence, creativity, and people.
If you are also trying to figure out what you want to do, instead of trying to answer that question directly, try interviewing yourself. It's a quick way for you to understand the "What If's", and best of all, it is fun to do :)