Interviewing Risk-Takers, What To Ask?

August 6, 2008 7:29 PM

If you had the task of conducting interviews with people meeting one or more of the criteria listed below, what kind of questions would you ask them? - People who have dropped their 9 to 5 or a high pay/high stress job in order to follow their passion. - People who have started their own unique small business. I'm thinking along the lines of something progressive and sustainable. - People who live unique lifestyles or combine their lifestyle with their job. For example, a person who turns a hobby into a profession. - People who have beaten the odds to achieve something extraordinary. - People who have taken risks in order to achieve their ideal lifestyle. Thanks!
posted by ISeemToBeAVerb to society & culture (14 comments total)

Sorry, obviously my HTML didn't work. Maybe this is more clear: --- People who have dropped their 9 to 5 or a high pay/high stress job in order to follow their passion. --- People who have started their own unique small business, I'm thinking along the lines of something progressive and sustainable. --- People who live unique lifestyles or combine their lifestyle with their job. For example, a person who turns a hobby into a profession. --- People who have beaten the odds to achieve something extraordinary. --- People who have taken risks in order to achieve their ideal lifestyle.
posted by ISeemToBeAVerb at 7:35 PM on August 6

What's the goal of the interview? To write a "aren't they cool" article? To find out how you can walk that path? To learn about potential pitfalls and illusions?
posted by ebellicosa at 7:46 PM on August 6

There was an FPP about a similar project (by a MeFite) recently that may have some relevance for your project.
posted by Forktine at 8:31 PM on August 6

What do you want to know?
posted by lunasol at 8:47 PM on August 6

Basically, I'm tasked with interviewing people for a magazine that focuses on lifestyle design. They are looking for people who embody the idea that life is what you make it, hence the focus on people who have chosen to follow their passion rather than submit to a traditional career and lifestyle. These can be all different kinds of people, the connection lies in their decision to follow their own path- to take that risk. For example, if you had the opportunity to pick the brain of someone who chose to leave their executive position at a prestigious law firm and start a small organic farm, what kinds of questions might you ask. I have a list of my own, I just thought I'd pick the hive mind for questions I might not have thought of.
posted by ISeemToBeAVerb at 9:08 PM on August 6

Setting aside the questions for a moment, the most important thing about interviews is to go interview the people on their own turf to pick up non-verbal cues on their personalities. If I had a choice between 20 questions to ask and five questions + an opportunity to visit their house, I'd choose the latter in a heartbeat.

But a classic question for this kind of story would be, "Looking back on your experience, if you could tell your past self anything about the decision you made, what would it be?"
posted by Cool Papa Bell at 10:04 PM on August 6

Alright, I'll bite. I'd want to understand them looking forward to this new life: what started them down the path? Did they realize they were changing their life or did they just sort of ease into it? Was there a snap decision and what triggered that? What was the first tiny step? When was the point of no return?

I'd want to see them looking back at their old life: When did they realize how much their life had really changed? ("omg, I used to be that guy with the disposable starbucks cup and now I'm the guy selling him his farm-fresh juice?") Do they miss anything? Do they think the rest of us are saps or sinners or what? What advice would they give to someone who feels stuck in their day job? [I'd minimize this part, since it's likely to be the most cliched.]

I'd also want to understand them in their evolving journey: Tell us more about their desire to feed people nourishing food. Do they feel that work is going well? Did they originally think they wanted to feed people nourishing food but then realized their calling was really to replenish and commune with the soil? How has their path changed them? What do they know now that they didn't know before? (Eg, I know people working for environmental groups who -- now, from watching the government up close, have decided that certain parts of the government are incredibly corrupt -- they never would have seen that corruption if they hadn't gone down that road.) What is their next adventure?
posted by salvia at 11:05 PM on August 6

1. Probably along the lines of Cool Papa Bell: With the benefit of hindsight, how could you have gotten to where you are now, more easily/better/faster.

2. Are there opprtunities -- education, networking, business, whatever -- that you passed up that you now know would have been useful. (For instance, when I started my first business and discovered that all of the business part of my business computing course was actually _useful_, and I should have paid attention rather than griping about it.)

3. What are the best mistakes you made?
posted by The Monkey at 11:26 PM on August 6

I think I would ask them what circumstances lead to the decision to leave the herd and follow a dream, and what in their past prepared them for their choice of livelyhood. I chucked it all and started my own graphic mosaic business after working in retail for 25 years. It all started when I was digging a garden and found it was a dump of old china dinnerware (for some reason that still remains a mystery). The leap of faith to follow a passion can be an interesting and unique story in itself.
posted by Acacia at 2:16 AM on August 7

In my view.. there are 2 types of people:

1.) The person who has plenty of resources and chooses willingly to make a major lifestyle change. Sure - they are motivated and inspired,etc,etc... and its great to see someone explore something completely new/unknown. (if you are person#1: would you make the same choices for life change if you literally had nothing but the clothes on your back? If YES, how ?)

OR

2.) The person who (through some unexpected circumstance) has a new lifestyle forced upon them. (loses everything in a house fire, becomes disabled somehow, overcomes addiction, recovers from destitute circumstances,etc,etc)

Personally I'd rather talk to person #2 .... most likely they had to sacrifice more and fight harder to get what they want, so its going to end up being a much more "human" story.

What would I ask them?
...why did you NOT hesitate?
...at some point you probably wanted to give up. Why did you choose not to?, and how did you summon the strength?
...Now that your life has completely changed, your perspective probably has too. What new insights or lessons have you learned that give you a deeper understanding of life.
...Now that your life has changed, do you ever encounter difficulty getting people to understand you? (or have problems relating to people?) Explain.
posted by jmnugent at 2:35 AM on August 7

I'd recommend picking up and reading the Po Bronson's book "What Should I Do With My Life?" You're basically writing the article version of his best selling book.
posted by NotMyselfRightNow at 4:37 AM on August 7

To what extent has the saying, "Do what you love and the money will follow" worked for them? Did they need to support themselves via their passion when they started, and do they now? Or did they/do they have other sources of income? How does the need to make a living in the field they're passionate about shape how they do what they do?

For my own interest this past winter, I interviewed a bunch of craftspeople about these topics at a prestigious juried. Practically without exception, they either needed other sources of income to support their lifestyles as professional craftspeople, or they had gone into 'production mode,' making the same top-selling items repeatedly, or they had gone into 'manager mode,' with employees taking over the bulk of the hands-on craft. In some cases, they were very satisfied with these choices, but understanding them helped me gain a more realistic perspective on what it's like to try to make a living as a craftsperson. So, I'd like an article like yours to be similarly enlightening, by celebrating the passionate side while also exploring its practicalities.
posted by daisyace at 4:55 AM on August 7

These are all really great questions., thanks for all the input!
posted by ISeemToBeAVerb at 8:17 AM on August 7

Ooh, don't forget to ask about the people who supported their transition - family, friends, etc. How was it hard on their partner? What kind of support did they most appreciate?
posted by ebellicosa at 11:04 PM on August 7