Great Career Paths are Messy Creatures

Most people seem to dislike their jobs or at best, find it tolerable. So when we encounter someone who seems to have a great job – work that is interesting, enjoyable, fulfilling and  impactful – it’s natural to get curious. How did they get there? What steps did they take to arrive at their current position. And of course:

How can I do the same?

I’d like to suggest two resources for everyone in their quest to reach their own great career:

Resource 1: So Good They Can’t Ignore You

The first is a book by Cal Newport of Study Hacks called So Good They Can’t Ignore You. This book, (based of a quote by Steve Martin), offers a framework for finding great work.

Great work, according to Newport, is work that offers things like autonomy/control over your work, the feeling that you’re good at what you do and a sense that you are having an impact on the world. He argues that getting a fulfilling career has far less to do with the type of work you do (the first chapter is devoted to bunking the myth that the way to a fulfilling career is “following your passions”) but more has to do with building career capital and leveraging it to gain a position that offers these things.

Career capital depends on the type of role you seek (for TV writers, it’s simply the ability to write really good scripts, while for entrepreneurs it might be a mix of technical skill, unique insight into a market, and a network that can reach great investors). The book is relatively short, quite insightful and full of profiles of people who have found great work. Go check it out.

Resource 2: CareerHoot Interviews

The second resource is a website called CareerHoot by my friend Andrew Chen which an online resource of interviews of people who have made career transitions – so people looking to switch jobs can see how others have done it.

Andrew and I recorded a ~40 minute interview about how I’ve navigated my own career – from messing around on Photoshop as a kid to studying biology to starting a startup. An old friend of mine reached out to tell me how much he appreciated understanding all the twists and turns that have lead me to where I am, and I hope it does the same for some of you.

An excerpt below. Click here to read the whole thing.

Q. Tell us how your career has taken you to your current role, and what were the most important thought processes you went through at key moments along the way?

A. Sure. I would say it comes back to my interest in technology. In middle school and high school, I really liked seeing all the different kinds of technologies out there, playing with things like Photoshop, learning HTML, messing around, making GeoCities pages, little things like that, nothing too serious. But I always found playing with computers pretty cool.

I did well in science-based classes in high school. I took a couple AP courses and so when I got to Stanford, I had a general interest in science. In my first year, I explored different classes but realized that something more science-oriented was going to be best for me.

I majored in biology because it had a broad range of different sciences — physics, chemistry, as well as biology and there were these problem sets, so that was a practical consideration.

I loved all the energy that was happening in Silicon Valley — seeing Google, Apple, seeing all these different startups coming up, but I didn’t know how I would be able to play a role in these companies because I wasn’t a programmer.

I had taken some programming classes in high school and then a little bit in college as well, but I was really struggling with the amount of time it took and the mental processes that were required that, for whatever reason, weren’t something I felt particularly where I could excel. So I was thinking, “If I’m not a programmer, how can I get involved in a tech company?”

Click here to read the whole thing.


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Jason Shen

Jason is a tech entrepreneur and talent expert. He is CEO of a performance hiring platform called Headlight, a Fast Company contributor, and an advocate for Asian American men. Follow him on Twitter at @jasonshen and subscribe to his private newsletter.

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  1. Love it – tactical tips and resources for the hungry career dreamer – thanks for the shout out jasonshen!

  2. @andrewlchen it’s a really really good book, I highly recommend it for you as an emerging thought leader in the career transition space

  3. CareerHoot looks awesome, thanks for sharing Jason. 
    I wanted to bring another cool resource for people looking to transition careers to attention called MiniMentor ( One of the challenges in career transition is the upfront costs of test-driving a job. In many cases, the only way to see the real deal is actually landing a job or internship.
    This service facilitates short-term apprenticeships (5-6 hrs) where people looking to break into a particular industry can shadow a professional with the goal of obtaining a better understanding if that career is one they’d actually want. Definitely check it out.

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