Recommendations for high school students

July 11, 2016

These are articles/books/videos that I feel are particularly helpful to high school students, for whenever I go to speak on career panels and such.

What to work on

"What You'll Wish You'd Known," Paul Graham
I dislike the dismissal of college admissions officers in this essay, but I support pretty much the rest of it. A few excerpts:
I'll start by telling you something you don't have to know in high school: what you want to do with your life. People are always asking you this, so you think you're supposed to have an answer. But adults ask this mainly as a conversation starter. They want to know what sort of person you are, and this question is just to get you talking. They ask it the way you might poke a hermit crab in a tide pool, to see what it does.
Right now most of you feel your job in life is to be a promising college applicant. But that means you're designing your life to satisfy a process so mindless that there's a whole industry devoted to subverting it. No wonder you become cynical.
Rebellion is almost as stupid as obedience. In either case you let yourself be defined by what they tell you to do. The best plan, I think, is to step onto an orthogonal vector. Don't just do what they tell you, and don't just refuse to. Instead treat school as a day job. As day jobs go, it's pretty sweet. You're done at 3 o'clock, and you can even work on your own stuff while you're there.
"Building Your Inner Coach" (18min TEDx talk), Brett Ledbetter
Focus on building your processes and systems towards your goals and success, rather than just the results themselves.

"Let's Teach Kids to Code" (17min TED talk), Mitch Resnick
People are growing up as tech users, but not necessarily tech builders. You don't have to think of yourself as a "computer person" to give learning to code a try. But perhaps you should think of it as: do you want to give instructions to computers, or only receive them instead? The former gives you more of the thing that all teenagers want, which is: freedom.

Figuring out what you want to do for a career

Career advice from the creator of Dilbert, Scott Adams
1. Become the best at one specific thing.
2. Become very good (top 25%) at two or more things.
The second strategy is fairly easy. Everyone has at least a few areas in which they could be in the top 25% with some effort. In my case, I can draw better than most people, but I’m hardly an artist. And I’m not any funnier than the average standup comedian who never makes it big, but I’m funnier than most people. The magic is that few people can draw well and write jokes. It’s the combination of the two that makes what I do so rare. And when you add in my business background, suddenly I had a topic that few cartoonists could hope to understand without living it.
Capitalism rewards things that are both rare and valuable. You make yourself rare by combining two or more “pretty goods” until no one else has your mix. 
The book that introduced me to the idea that "follow your passion" advice gets it wrong because your aim should be to get really, really good at something. I like to tell people that things you're looking for are pursuits where you enjoy the process of getting better at it.

How do I choose a career path?
I just took jobs I could get using skills I felt reasonably confident I had (for me, at the start, those were writing and being compulsively organized), and then over the course of doing those jobs, gathered and refined information about what I liked doing and what I was good at and what other people thought I was good at and were willing to let me do more of.
The Secret to Being Happy with Your Job: It's not 'follow your passion'
I figured out that biggest mistake I’d been making was asking “What job would I want?” instead of “What do I want out of my job?” In other words, I needed to shift from statements like, “I want to be a writer,” or “I want to be a fashion designer,” or “I want to run my own business,” to “I want a creative atmosphere,” or “I want to work in a team setting.” Because “I want to be a writer” doesn’t actually mean anything tangible.
I like data, so I made a massive list of every workplace quality that had given me joy, and conversely, the ones that made me miserable.
After that, I started asking everyone about what moment in their job made it worth it. The most memorable response came from an engineer who said his happened when he “solved the problem.” Not when the product was made. Not when it was delivered. Not when it was sold. Don’t get me wrong, many people listed more than one core moment. But it became clear that I needed more of whatever it was that made me stoked.

Informational interviews

Cold-emailing strangers to ask for career advice: some things that you can do that will make people more likely to want to help you

Actually useful questions to ask in informational interviews: "don’t just focus on being impressive (which is the pitfall a lot of people fall into), but think seriously about what you’re really wondering about"

Doing well at your first jobs

5 Mistakes Smart People Make at Work: These are all good points, especially "if you’re used to being 'the smart one' and things have always come easily to you, you might not have built up the skills you need for when things are hard."

What Your Internship Manager Wishes You Knew: all good, especially:
  • "Working an internship is different from being in school"
  • "college often rewards lengthy explorations of a single topic. In the work world, shorter is nearly always better"
  • "Effort is nice, but it’s not what matters" 
A roundup of other relevant Ask a Manager posts for new grads.

15 things you don’t know about work when you’re early in your career: again all good points, especially:

  • "I’m the only person who’s fully immersed in my own day-to-day work, and I have to speak up when I want my boss to fix something."
  • "leaders are far more interested in how you plan to fix the issue vs. who was responsible for causing it."
  • (misconception that) "If a process or tool doesn’t work the way an employee thinks it should, it must be broken and in need of fixing. In a lot of situations where this came up, the employee didn’t have (and didn’t seek out) any background on why we did things the way we did, and just assumed management must be idiots. In reality, there were nearly always valid (and sometimes legal / regulatory) reasons why things worked the way they did."
  • (misconception that) "If I see something I perceive to be a problem and report it, my work is done and someone else will fix it."


The UpSide of Down, Megan McArdle
Megan McArdle have been my favorite bloggers to read for several years now, I just like her writing and argument style a lot, and it's informed how I think about things, even if I don't always agree with her. Anyway, this is her book about failure and why it is necessary yet difficult to accept as a part of improving over time.

Keeping track of your accomplishments

July 5, 2016

It's really valuable to keep an ongoing list of what you've actually been doing at your job. This is helpful for:
  • writing the self-assessment part of a performance review at the end of a quarter
  • help your boss make a clear, specific case for you to be promoted, and not rely on their distractable memory
  • updating your resume/LinkedIn when the time comes
  • reminding yourself that you have been competent and gotten stuff done before, if you're feeling frustrated or having a bad day

I just have a Google Doc called "Accomplishments" that I'll add things to every so often, including any kudos or compliments that I receive from co-workers. I'll also write up a short description of a project I worked on that succinctly describes why that project matters to the business and what was hard (and therefore impressive) about my part of it.

Trace Store Service Integration
Migrate from directly accessing databases through ActiveRecord to using a Thrift service instead, enabling our Data Services team to change storage backends without disruption to our end users.
Team size: 2
Don't forget to check if someone would still ask "so what?" at the end of your writeup!