How to Choose Your Next Skill

Ramses Oudt 6 min read
How to Choose Your Next Skill

The only way to learn new skills is to show up. But how will you be able to keep going if you're unmotivated or have no time to practice? Choosing the right skills is just as important as picking the right tools and techniques to learn them.

Now that so many skills are digital, we have endless opportunities to learn. If you wanted, you could start learning a new skill every day. But if you want to become good, fast, you need to focus on a limited number of skills at the time.

Learning one skill means you're not learning another. To make most use of your time and energy, you need to decide what skills to work on and in what order. Stack your skills to learn faster and make it more fun.

In this article, I'll show you my thinking process for deciding what skills to work on. I'll guide you through a few exercises that I've used dozens of times to pick new learning projects and help others find theirs.

While having a plan is crucial, always keep in mind that learning is messy. No plan is perfect, so don't get stuck in the planning process.

Use these techniques to clarify your thinking, look for fellow learners, and just get started. As you learn and practice your wanted skill(s), you'll discover what to focus on next.

Skills, knowledge, and acquiring them

Let's start with some definitions before getting into the deep end of how to decide what skills to acquire.

In this Information Age we often think of learning as acquiring knowledge. We take in information, think about how we could apply it, and then have some kind of knowledge about that thing. Like understanding the basic concepts of programming. But knowing a few concepts does not mean you can apply them successfully.

A skill is all about knowing how to apply knowledge. To continue with the programming example: when you are skilled in programming, you've applied and practiced theoretical concepts enough times to make the knowledge part of you. Or as Cedric Chen of Commoncog would say: you've acquired tacit knowledge.

How to acquire a skill is outside the scope of this article, but keep in mind that knowledge is a prerequisite for mastering any skill. And the first bit of knowledge you need before choosing a new skill is knowing what problem you're trying to solve and why.

Find your why first

Before picking a skill to learn, you need to gain some clarity about the future you want for yourself.

One visualization exercise to find my why is one I picked up from the Building a Second Brain course. By simply closing my eyes and thinking about how I want my life to be in one, five, and ten years from now, I allow myself to dream bigger than I usually would.

Personally, I look ahead at what I want my life to be, and I especially look at how I want to be. I ask myself questions like: how can I be the best partner, friend, and colleague possible? What will my thinking and behavior be like? What do I still need to learn? And how can I make learning it a habit?

Once I have clear where I want to be long-term, I increasingly narrow my focus to this year, this quarter, and this month. While a long-term vision can feel daunting, thinking about what step I could take now towards my vision gives me a sense of control.

Apart from my long-term vision, I also think about my current roles and responsibilities. Maybe I will need to lead a project three months from now, but realize that I have never run such a big project. That could be a signal for myself to read up on project management skills and apply subskills to whatever life area I see fit.

Visualization is a powerful way to find your why. When you think about a potential future and feel excited about it, that's a clear signal to dig deeper. Dare to dream big.

Map your skills

You learn much faster when you have a use for a skill. A vision can be a strong motivator, but nothing works better for learning than solving a pain point.

One exercise I like is the "hedgehog" from Jim Collins's book Good to Great (which I in turn pick up from this article by Erika Andersen). Collins describes it as three areas where great companies focus on. We can use it to guide our thinking toward what skill to acquire next.

The hedgehog questions are:

  • What skills bring in money?
  • What skills am I already good at?
  • What am I passionate about?

Answering these questions will help you to brainstorm potential skills.

By thinking about what you need to learn to bring in money you get a boost in motivation. You also tend to have more opportunities to practice if your skill makes you money.

Thinking about what you're good at can boost your learning pace. What you already know is the best starting point to learn. More skills are similar than they seem on the surface, so always look for analogies when learning new things.

Finally, finding your passion is probably the strongest motivator. Passion is why amateurs in all kinds of domains have lack of sleep as they're learning and practicing into the wee hours. Think about what you've spent an insane amount of time on with joy being the only reward. Chances are, you're already good at that skill and only need to find a way to earn money from it.

But, beware: not all passions should be monetized. Making something a job can kill off your passion for good.

To kickstart your thinking process, I've created a visual worksheet so you can define a clear vision, identify your work/life roles, brainstorm your wanted skills, and map them onto your roles. This will help you gain clarity about what skill(s) to tackle first.

Click here for the Exalidraw file. It contains all the instructions on how to use it, as well as an example. Below is a short instructional video if you're unfamiliar with Excalidraw.

Dissect your wanted skill set

Now that you know what high-level skills you'd like to learn, it's time to dissect the ones that bring in money, you're already (somewhat) proficient at, and are passionate about.

Let's dig deeper as you gain even more clarity about what to learn.

Every skill is made up of subskills. The trick is to deconstruct the high-level skills to their individual parts and line them up in order of learning. This is a skill in itself, and one you need to practice repeatedly as you're progressing with a skill.

One approach I've found useful to dissect and sequence acquiring a new skill is Tim Ferriss' DiSSS framework (the i is only added to make the acronym easier to pronounce):

  • Deconstruction — What are the minimal learnable units, the LEGO blocks, I should start with?
  • Selection — Which 20% of the blocks should I focus on for 80% or more of the outcome I want?
  • Sequencing — In what order should I learn the blocks?
  • Stakes — How do I set up stakes to create real consequences and guarantee I follow the program?

Click here for a detailed explanation from Tim's book The 4-Hour Chef.

Dissecting a skill is difficult. That's why I always recommend people to look for an online community of fellow learners, or to talk to several people who already learned the skill. However, it's often best to talk to fellow learners who are just a few steps ahead.

If you talk to people who mastered a skill long ago, they often don't remember exactly how they learned it and cannot precisely tell you what to focus on first. Teachers and coaches are often experts that do have a beginner mind as they go through the fundamentals so often.

Once you've deconstructed your main skill, selected the highest leverage subskills, and picked one subskill to start with, you can make a more detailed learning plan.

How to create a learning plan is outside of the scope of this article. But I will leave you with one tip to start gathering materials and hit the ground running.

Share your learning goals

Before you dive headfirst into learning the new skill you picked, it's always good to orient yourself first and see what learning materials and techniques there are out there.

The best and easiest way to set yourself up for serendipitous encounters is by sharing your learning goals online.

If you're active on social media like Twitter or Facebook, dedicate a thread or post to what skill you're going to learn, why you picked it, and how you want to approach learning it. Chances are, like-minded people will see what you've posted and chime in or at least encourage you.

Simply declaring you're going to learn something can give a boost in motivation.

In case you've already found a community about your desired skill, it's probably best to post your learning goals there as well. It'll serve as a nice introduction to the community, and will likely bring you in contact with fellow learners who are further along.

Cherish your fellow learners, as they're the perfect guides to tell you where and how to start.

Last but not least, share your learning goals in the Think Stack Club on Discord. No matter if your goals are completely clear or not, there's always somebody willing to give you feedback or nudge you in the right direction.

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