Your time is scarce. You have to choose where to spend it. With a plethora of options available to you to learn new skills, how do you choose which ones to take the time to learn and which ones to outsource to people who already know them?

Even more, there are different ways to learn new skills. You can take a course, hire a coach, read a book, listen to podcasts, build test projects, and interview experts. Which skills lend themselves to which learning styles?

Having a system for organizing these choices can cut back on the mental cost of deciding and help guide you to spend your time more effectively.


My career coaching clients are usually either professionals making a transition in their careers or ambitious young people getting started on their careers. In almost every case, they need to learn new skills to build a successful career. Even more, these are ambitious people who enjoy learning, so they want to set up jobs and careers that empower them to learn new skills.

In the course of doing business, though, there are skills that present themselves as valuable to know for the execution of the business. To learn these skills requires spending time or energy that could be spent on learning other skills.

Just yesterday, I had a call where this issue presented itself. The question came down to deciding whether or not to learn a set of skills (in his case, front-end web development for building custom dashboards and quality audio production for podcast development) that are tangentially required for the client’s work or to spend the time and money learning other skills that would allow him to take on larger projects with wider scope (in his case, becoming a skilled SQL developer and getting started on machine learning and neural net courses).

Of course, there’s other work he has to do to scale his: he has to schedule meetings, do research on clients, potentially do some data entry, and do mail merges. Each of these skills is relatively easy to learn but does not provide a direct increase in opportunities for knowing how to do it.

The Four Types of Skills

There are a few options for how learning skills and division of labor can break down:

High Return On Investment and Steep Learning Curve: These are skills that, should you know how to navigate them and learn them well, you can substantively increase your opportunity or learning power but they are difficult to learn. In his case, machine learning is an example of this. It takes time, energy, and is a complex field of study difficult for novices to navigate.

Low Return On Investment and Steep Learning Curve: These are skills that, knowing them might mean you can do some work you couldn’t otherwise do, but they don’t substantively increase your opportunities and there are others who have already invested the time and energy to learn them. In his case, front-end web development is an example of this.

High Return On Investment and Shallow Learning Curve: There are some skills that can be learned relatively quickly and open up great opportunities for people. Basic writing and communication fall into this category.

Low Return On Investment and Shallow Learning Curve: Some skills are easy to learn how to do but knowing how to do them doesn’t add much for the learner who has other skills to learn. These are skills like scheduling meetings, doing mail merge, and data entry.

Like any good analytic dilemma, this breaks down well into a 2×2 matrix.

How to Approach Each Category

High Return On Investment and Steep Learning Curve: You want to become good at skills in this category and should be willing to pay for value. While different learning styles lend themselves better to different people and knowledge, this is the quadrant of the matrix where paying for high-end classes, coaches, workshops, and projects makes the most sense. Spending the money helps you make the psychological commitment to get the most out of it and helps guarantee that you are getting something worthwhile from somebody who also has skin in the game to deliver a good product. Schedule time to learn these skills and build them into your own professional development plan.

Ask yourself: How much more could I do if I really learned this and understood it?

Example: Whatever allows you do to your craft more and better. If you do data science consulting, learn more data science and business development. If you do relationship coaching, learn copywriting and sales funnels. If you do software development, become better and grow your stack.

Low Return On Investment and Steep Learning Curve: Your time is better spent in the High ROI/Steep Curve quadrant than here. The people who are masters (or at least, quite good) at skills in this quadrant probably spent time in that quadrant. Beyond (maybe) some basic fundamentals, outsource to these people.

Ask yourself: What else could I be doing with this time? What else could I learn?

Example: Software development (for non-software professionals), audio and video production, design.

High Return On Investment and Shallow Learning Curve: This is where most books, free courses, and podcasts end up. For most subjects, reading 2–3 books on the topic makes you more knowledgable than 95% of the population.

Ask yourself: Do I know people who improve their professional position based off of (only) reading books or watching videos on this?

Example: Basic financial knowledge, basic negotiating, basic writing and communication (at a certain point for each of these, you can move into the High ROI/Steep Curve quadrant if you want to specialize in these areas), email scripts.

Low Return On Investment and Shallow Learning Curve: Some skills are easy to learn but knowing how to do them doesn’t add much for the learner who has other skills to learn. These are skills like scheduling meetings, doing mail merge, and data entry.

Ask yourself: Is there a way I can automate this? Is there a service that I’m willing to pay to take care of this for me?

Example: Services like Calendly and MeetWithMe let you automate the scheduling process and avoid spending valuable time going back-and-forth with other people trying to find a time to talk.

Some important definitions:

Return On Investment does not just mean “can you earn a lot more with this?” It means, “can you learn a lot more with this relative to what else you could be doing with your time?” It’s useful to remember that ROI is expressed as a fraction as: ROI = (Investment Revenue-Investment Cost)/Investment Cost.

Steep/Shallow Learning Curve refers to how difficult it is for you to learn this skill. A steep learning curve refers to something that is difficult to learn for any reason. Something can be difficult to learn because it requires esoteric knowledge, because it requires a substantive time investment, or because it just contains a lot of nuance. A shallow learning curve refers to something that is easy to learn.

LEARN THE SKILLS SCHOOL NEVER TAUGHT YOU.