My favorite question to ask people who I have just met, or haven’t known for long, and one that really helps in understanding a person’s motivations and personality, is one of the simplest.
What was the first thing you wanted to be when you grew up?
If you’re asking a woman, make sure to toss in the corollary, “And don’t say ‘princess.’ Everyone says ‘princess.’” I’m not trying to be sexist here, but after having asked this question for years on end, I have noticed that most women will say ‘princess’ at the first pass.
When you ask someone this question, you find out a lot about where they started. A police officer or firefighter was concerned about public safety. A doctor or nurse wanted to help individuals and families. A construction worker wanted to create and help build something with others. An astronaut wants to explore and find new things to share with others. Whatever it is, the position has something to do with their earliest impulses towards others and some core concepts about society and others.
A good follow-up to the question is, “What do you do now?”
Besides the implied disconnect between original intentions and current execution (in a statistic I just made up, around 3% of people get the job they first wanted), you can track the progression and development of your conversation partner’s career path. Although few people end up with the job that they first wanted, many of them still have a tangential relationship between the two. The core values or underlining reason behind the first job that they ever wanted can still be found in their current vocation.
It’s also a good question to ask yourself. Why did you want that first job? What led you to your current field? Why do you have (or are you searching for) that career? Have you moved away from your original plans, and if so, why? What changed?
Answering these questions can help you to determine your real motivations for your present employment situation, and might give you some insight on where you want your career to go next.
And if you’re wondering, I wanted to be a T-Rex when I grew up.




