Take the Guesswork Out of Choosing a Career | Prototyping

What do you want to be when you grow up? Where are you headed? What are you majoring in? Since childhood, we have been routinely questioned about our life’s direction. It can be stressful and overwhelming to choose a career trajectory. How do you know what you will like? What if you get sick of it in three years? Where do you start? Prototyping takes the guesswork out of career choice decisions.

Designing Your Life: How to Build a Well-Lived, Joyful Life by Dave Evans and Bill Burnett is a must-read for anyone exploring career options, pondering switching career trajectories, or desiring to live a great life. One of my top takeaways from the book is the practice of prototyping.

What is prototyping?

“The simplest and easiest form of prototyping is a conversation….Prototypes should be designed to ask a question and get some data about something you’re interested in. Good prototypes isolate one aspect of a problem and design an experience that allows you to “try out” some version of a potentially interesting future.”

In the case of career exploration, prototyping takes places in the form of interviews. It is sitting down with a professional in your field on interest and picking their brain. You can discover so much more information about the ins-and-outs of daily life in a career that Google will never provide. You can also get an honest look at the struggles and downsides of careers as most people won’t mention this online.

Your natural concerns

It is natural if this sounds uncomfortable. Maybe you are thinking Am I wasting their time? Will they feel like I am taking advantage of their expertise for free? Why would they want to take time out of their schedule to discuss?

In Designing Your Life, they expertly cover this mental misconception with the analogy of giving directions. When someone is new to your town and asks you for directions, do you feel ripped off? Taken advantage of? Having wasted your time? No. Actually, the opposite is true - you probably feel a little boost of happiness for having helped someone out. The same goes for these interviews. People are happy to share their expertise, talk about their success, and help someone who is just starting out. Plus, it is flattering to them to have someone view them as a professional to seek advice from. It brings them joy.

How to Prototype + Checklist

A little while back, I did a series of prototyping interviews with wedding and portrait photographers. I had done research about photography, watched videos, and done plenty of photo shoots with friends, but I wanted to look into the business side and day-to-day life of being a professional photographer. So, I did research for local photographers. Then I drafted an email expressing my interest in photography and asking to chat over coffee about their career. Most happily said yes. Check out the checklist below as to how I landed this prototyping interviews:


  • Do some research (LinkedIn is a great tool for this) in your area for experts who are in your field(s) of interest that you have questions about.

  • Come up with a list of people and shoot them an email asking if you can buy them a coffee at a place and time convenient for them and chat for half an hour about their career.

  • Compile a list of questions and be prepared. For this, come up with specific questions tailored to what you want to learn about their career. Do not bring vague inquiries such as “tell me about your career path” or “tell me about photography.” Be specific and intentional, but of course, mix it in conversationally. No one wants to feel like they are in an interrogation scrutinizing their career. Each interview will go differently - some people will talk for fifteen minutes answering one question while others others will answer each question in under two minutes. So be prepared, come with a LOT of questions, but don’t ask them all.

  • Schedule the interviews (and a lot of them) and have fun!

  • At the end of an interview, ask (if you are still interested in the field) if they would be open to you shadowing for a day or ask something along the lines of how they would recommend someone like you enters the field. These questions can lead to amazing opportunities and even jobs (see below).

  • Follow up each interview with a thank you note!

What were the results of my prototyping?

Personally, I had great success with prototyping. Almost everyone I reached out to was excited to do an interview, and if they could not fit an in-person meeting in their schedule were happy to schedule a phone call.  From interviewing around ten photographers, I landed two internships and over five shadowing opportunities. And that was only from ten interviews! In Designing Your Life, they go into greater detail in how prototyping can lead to jobs and interviews.

Prototyping greatly helped me narrow the type of photography I wanted to pursue. I went into these interviews expecting to follow a career path in wedding photography, but quickly learned I prefer portraits and commercial. I also gained a ridiculous amount of knowledge about tools, resources, and workflow of photographers. Of course, each person’s experience and story is different, but many of the photographers solidified each others advice.

If you are considering changing career paths or exploring options, I cannot recommend prototyping enough!

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Kayla SanoyComment