A Subtle Mistake About How to Acquire Useful Career Skills

As promised, here is the second post written by Scott Young about lessons learned from the many years we’ve run our Top Performer online course, which we’re re-opening next week. This post is about a mistake we made with our curriculum in the early pilots of the course.

If you’re missing Cal content this week, fear not, I’ll be back to my regularly-scheduled programming next week. In the meantime, you can take a look at my recent New York Times op-ed on 5-hour work days. My basic thesis: it’s hugely surprising that we don’t have many more knowledge work organizations aggressively experimenting with novel approaches to work.


In our early Top Performer pilots (before we even called the course “Top Performer”), Cal and I made a subtle mistake about the process we taught for acquiring career skills. It’s one I’ve seen many people make when thinking about improving their career, so I think it’s worth exploring here in case you might be making it too.

A big part of our course is executing a skill-building project. The goal is to cultivate rare and valuable skills which form the foundation for a successful career.

What we hadn’t recognized in early iterations of our course is that there are actually two different ways to go about these project, one of which tends to be much more effective.

The Difficulty with Drilling Down

The first way you can design a project to upgrade your career skills is to drill down on some aspect of your work that’s important to your job. One of our students, for example, was an academic philosopher who decided to get better at logic. Another student was an architect who decided to deepen his understanding of design.

On the surface, these kinds of projects sound like they should be helpful. Indeed, the entire idea of deliberate practice, on which our course is based, seems reflected in these projects—pick an aspect of your work, and then design an effort to focus on improving it deliberately. So what’s the problem?

The problem is that a lot of these projects didn’t generate spectacular results. Sure, the person might have felt good about deepening a skill, but these were rarely the projects that resulted in promotions, raises or transformations of a person’s work.

True, there were some exceptions. One person decided to dig deep on their understanding of a programming language, and later translated that into landing his dream job.

But even then, this particular success didn’t come from improving a skill alone. In his particular case, the student got the job because his practice activity (making online quizzes about the language he specialized in) brought him to the attention of experts in his field. Had those quizzes not been published (or acknowledged) and it’s unclear how big an impact his project would have had.

Benchmarking Success

A different style of project, however, does seem to work better: benchmark projects.

Benchmark projects are also about improving skills. However, instead of picking a skill and just trying to get better at it, you first pick a clear benchmark accomplishment that defines success. Examples of successful benchmark projects could be:

  1. Writing: Creating a blog and producing 100 articles.
  2. Programming: Designing a useful open source library.
  3. Academia: Producing a paper that attracts multiple citations.
  4. Entrepreneurship: Creating a new product that will sells a certain amount.

Why are these projects (often) more successful than projects which are strictly about drilling a particular skill?

My experience tells me that there are two distinct advantages at play here. The first is that by tying your project to a benchmark, you can’t avoid the uncomfortable work. A deliberate practice project that’s disconnected from real-world results can unintentionally be steered away from hard efforts that move the needle, allowing you instead to wallow in that pleasing state of “tractable hardness” — a state that feels good, but generates minimum growth.

Second, benchmark projects produce a recognizable achievement at the end. This helps by allowing you to point at something concrete when trying to articulate your newly acquired skill. Good work alone can propel you forward, but making your skills more legible to outsiders is often a key part of translating those skills into actual career benefits.

How You Can Create Benchmark Projects to Grow Your Career

The way I like to think of benchmark projects is to pick something that I can’t do right now, but I might be able to do, if I improved my skills and worked at it.

These projects tend to work better when the benchmark itself suggests what kind of efforts you might take to improve. Improving as a writer, for instance, it would be better for me to pick a project like, “Get published in a national newspaper or magazine” rather than “Sell one million books,” since the former will suggest a lot of specific actions I need to take to get my writing to the level where I could be published in a prestigious place, but the latter doesn’t really suggest anything concrete.

Good benchmark projects are often scarier than drill-down projects. “Getting better at research” is a lot more comfortable a goal to set than, “Get my work published in a Top-5 journal.” Yet that uncomfortableness also encourages you to take a hard look at your own work.

What are some benchmarks you could strive to attain in your own work? How would those look different than attempts you’ve made in the past to simply “get better” at your work?

13 thoughts on “A Subtle Mistake About How to Acquire Useful Career Skills”

  1. I don’t follow the difference between “Get published in a national newspaper or magazine” and “Sell one million books”. They both seem to suggest concrete actions. It just feels like the outcomes differ in terms of magnitude rather than kind.

    • I don’t think that’s the contrast that Scott is making here.

      The two example you gave are both clear benchmark examples, at least if I’m understanding the definition correctly.

      Both have a concrete outcome, and a tangible product of your efforts that require deliberate practise.

      • The distinction is that getting published in a prestigious journal contain steps that are more tangibly concrete to execute. Selling a million books in dependent on more variables that are out of one’s control.

  2. Great points! Yes, as a pet project it’s great to drill down into personal interests regarding specific skills, but moving the needle is a must in today’s economy. I think of it as combining the need (external) and the want (internal) and meeting in the middle somewhere ultimately benefiting career. Always keeping your eye on the ball, so to speak.

  3. How do you measure the quality of the output in a benchmark project? Deliberate practice says that I can play piano 10K hours and never improve due to lack of feedback.

    • On the specific example of playing the piano a benchmark project could be to have a public performance or a series of public performances to an audience of at least one or more. If you want to have a kind of a yardstick: do the patrons ask you to come back to do another performance?

  4. hi “Getting better at research” is a lot more comfortable a goal to set than, “Get my work published in a Top-5 journal.” Yet that uncomfortableness also encourages you to take a hard look at your own work.

  5. In order to really implement the principles of Deep Work and Digital Minimalism, it would be really useful to have a community of people able to support each other in the transition and have their questions answered. Does anything like this exist?

  6. Really great post. Without a “benchmark” goal, we give ourselves the illusion that we are improving because setting vague goals make ourselves more comfortable.


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