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Things You Can't Do from Behind a Computer, pt. 1

Article Table of Contents

Meet people. #

Over the last nine or ten months, I can clearly remember a handful of conversations I had. I initiated each conversation with someone that I wanted to learn from. Most I had some prior relationship with (I.E. I had met them, or I knew someone who knew them). This was all precipitated by a useful and provoking post by Ramit Sethi. more

These conversations were not social events, although in each conversation I have enjoyed myself. Each meeting was an opportunity for me to learn more about how these people have done what they have done. I framed them in my mind as “informational interviews”. In other words , I interviewed them.

I’ve met with a company-leading salesman, two business consultants employed by one of the “big three” consultancies, a freelancer who runs a very successful production studio, a CEO, a CMO/Marketing Director, a UX designer, another UX designer/web developer, a senior project manager in the banking industry, and a lawyer. In every instance I asked similar questions:

  • What challenges have you faced, first in your career, and second on your job, in the last few months.

  • How has your career developed, and led you to this place.

  • How did you achieve X (x=prior mentioned achievement, or something on their LinkedIn profile - yeah, I stalk.)

  • What is the most enjoyable part of your day/job?

  • Where do you see your self in two or three years?

I ask more questions. I always ask for just fifteen or twenty minutes, and I stick to whatever time limit I’ve set, unless they want to go longer. Half of these conversations have been over the phone, the other half face-to-face. I have derived so much value from these conversations. They have contained plenty of career advice, actionable suggestions, and encouragement.

Here’s a few gems that have been consistent across all of these “informational interviews”:

  • Career growth is not sexy - spend time cultivating useful skills, and then spend time figuring out how to use those skills in a way that can benefit your company or your career.

  • Get out and meet people and learn from them.

  • Learn to solve problems for others, but be sure to communicate this in a way that makes sense to them.

  • Sometimes the best option is to quit a specific job ASAP.

The goal of these informational interviews is not self-promotion or trying to get hired. I think this is the quickest way to ruin a conversation, and, oh yeah - COMPLETELY MISSES THE POINT OF AN INFORMATIONAL INTERVIEW!

Finally, here is how I benefited, and why you can never possibly achieve the same benefit until you get out there and do the same:

  • Now, when meeting with anyone (stranger at a BBQ, long-lost family members, friends) I try to guide the conversation with two ideas in mind: How can I learn more about them, and what wisdom might they have to share. Believe me - this makes more a much more interesting conversation than weather and football.

  • I am getting better and better at engaging in mature conversation with competent people. This is a skill that can compensate for lack of technical depth, and can open up doors that otherwise would not be open.

  • I am able to hear very specific bits of advice and wisdom, consider how to apply it to my own life, then immediately ask if my interpretation is correct.

  • I am getting better at reading subtle indicators of how a conversation is going. (Hint - you should know when to end a conversation, and it should be before the other person is thinking about ending the conversation.)

  • I’ve had a number of job offers/offers to connect me with people who are hiring.

  • I still sometimes get indescribably nervous, and can feel my chest tighten and it feels like my voice must be shaking and I’m about to fall over. Insane, and embarrassing. I’m working on it. This happens sometimes in other situations and is intriguing. The more time I spend “there”, the more I’ll be able to handle it.

  • I have decided very concretely a few career options that I certainly do not want to pursue. (Consultant with Deloitte? What was once a dream now sounds like hell. No thanks.) The time savings alone of not wasting hours or days (or months, years, and thousands of dollars) are incalculable.

You don’t need impressive networking skills to set up a meeting. Here is the FIRST email I sent out, asking to meet up with someone:

Hey R, 

This is Josh, from [company where I had met R]. N, a friend there, recently gave me your contact information and said I should get in touch with you. 


I would love to take advantage of your offer to get in touch with you by chatting with you for fifteen or twenty minutes about the work that you do with [company], what led you to work with them, and what has led you to stick with them. 


I will, of course, work around your schedule for a time to meet. If it is convenient  I would love to buy you a cup of coffee at a location and time of your choosing. 


Are you willing to set up a short meeting?


Thanks for your time!

Short, sweet, and it was so scary to send. This was what I sent, redundancies and all. I guess I should get a copy editor. The conversation I had with R was extremely helpful, encouraging, and still impacts me today. That was the first.

If you’re not sure what you want to do with your life, go start talking to people. I did not even know that User Experience and Design was a thing. I found out about it after some informational interviews and reading some books.

This is all I have for now, but please - take a step. Write down a list of three people you’d like to learn from. Make it happen. They’ll be flattered. Wouldn’t you be?