3 Hacks to Mastering Any Skill Quickly

Hacking Expertise

Cultivating a learning mindset is a key skill in any field.

This is especially true for a resource-constrained startup where you must balance competing priorities simultaneously: speed, learning, and focus.

In this issue, I will show you how I combine three scientifically-backed learning hacks to build an optimal learning loop:

  1. Deliberate Practice (learn by doing the right things),
  2. Psychological Safety (create a learning sandbox), and
  3. Perceptual Learning (learn without thinking).

Pillar 1: Deliberate Practice - Learn by doing the right things

Deliberate practice is often summed up as the 10,000 hours rule — popularized by Malcolm Gladwell in his book Outliers.

Studies have shown that there’s nothing magical about that number. Some people need more hours, others less. But researchers agree that practitioners need to clock many practice hours to gain mastery of a skill.

The problem: Time.

There is a faster way (more on that later), but first, I want to focus on practicing deliberately and correctly.

The real key to mastery through deliberate practice comes down to three ingredients:

  • Learn by doing/practicing the right things at the right time
  • Quality over quantity
  • Realtime performance feedback

1. Learn by doing/practicing the right things at the right time

You can’t learn martial arts, golf, or entrepreneurial thinking by reading alone. You have to do.

Practice Trumps Theory

At the other end of the spectrum, we also encounter people trying to act on too many things simultaneously. Trying to go fast on everything is a recipe for getting lost faster.

Only a few key constraints (or weakest links) are holding you back at any given time. Your job is to focus on those and ignore everything else.

This is the essence of practicing 🧘🏻‍♂️ Right Action, Right Time.

2. Quality over quantity

You won’t become a world-class musician by practicing the scales daily for five years. Similarly, there are diminishing returns to any practice activity. You need to know when you have crossed that learning threshold and move on to your next constraint (or weakest link). Otherwise, you fall prey to the local optimization trap.

Let's take learning from customers through interviews, for instance.

In the Continuous Innovation Framework, we use customer interviews to understand our customer's problems to help us design the right solution (problem/solution fit).

I often get asked how many interviews to run. My answer is the least number needed to demonstrate you have understood the customer's real problem.

Other practitioners mandate running a minimum number of interviews, like 30 interviews in 4 weeks. They sometimes even tie an incentive or punishment for not following through. The problem with this carrot-and-stick approach is that it doesn't lead to the right learning or behaviors because humans are great at gaming systems.

When confronted with a mandate like the one above, guess what happens?

Exactly 30 interviews get run, but quality often suffers.

If you can achieve the same results with just five interviews, why run 30 interviews?

You don't get a gold star for following process, but for achieving results (aka traction).

3. Realtime performance feedback

You don’t know if you’re getting better or worse without feedback. The key to deliberate practice is frequently pausing to check your work or, even better, having your work reviewed by someone with more expertise… and making many incremental adjustments along the way.

"If you get one percent better each day for one year, you’ll end up thirty-seven times better by the time you’re done."
- James Clear

Here’s a real-world example.

Radiologists are often sent MRI scans by referring physicians for diagnosis. But did you know that once the diagnosis is made, the radiologists get no follow-up feedback on the accuracy of their diagnosis?

As a result, they don’t get better.

One study significantly improved the accuracy of these diagnoses by allowing radiologists to first practice with simulations. In these simulations, they were shown MRI scans of past patients with known outcomes. After diagnosing an MRI scan in the simulation, they were shown the actual results.

Two 45-minute practice sessions were all that was needed to improve their accuracy drastically.

The key contributing factor was real-time feedback.

In a startup, this equates to shipping something daily to customers and measuring what they do, i.e., building a continuous learning feedback loop.


While many people understand the importance of deliberate practice and the need to push to the edges and beyond our comfort zones, doing this isn't easy because of our need for psychological safety.

Next, we'll discuss how this plays out with our ideas and approaches to overcome these setbacks.

Pillar 2: Psychological Safety - Create a learning sandbox

Achieving breakthroughs requires us to go to our edge and beyond our comfort zone. But what holds us back is our need for psychological safety. Most of the time, we don’t realize we are holding back because our brains trick us into thinking we are doing all we can.

These brain tricks are what psychologists label cognitive biases. And over a hundred cognitive biases unconsciously conspire to prevent us from sticking out our necks and instead protect the status quo (where it’s safe).


For example, it's much easier to post-rationalize and move on if you try something new and don’t immediately get the expected outcome rather than chase down why.

If, for instance, you launch a product during the summer months and it doesn’t sell, you might conclude that it’s because everyone is on holiday. If sales don’t pick up immediately after the summer, they just returned from the summer and might need some time to settle in. Then, here in the United States, we have Halloween in October, Thanksgiving in November, Christmas in December, New Year, etc. All these events conspire to distract your customers from buying your product. By this logic, it’s never a good time to sell.

This is our post-rationalization bias at work.

Another bias that trips most entrepreneurs is the Innovator’s Bias or our premature love for our solution. The safety gloves come on when we are asked to challenge our baby rigorously. We selectively hear what we want to hear (confirmation bias) and unconsciously post-rationalize one setback after another to preserve what we have already invested in (sunk cost fallacy).

You can see how these biases work together against us.

Reasonable smart people can rationalize anything. Entrepreneurs are especially gifted at this.

So what’s the solution?

You need to take a two-pronged approach to help you keep your biases in check.

1. Separate skills acquisition from skills application

First, you need to separate skills acquisition from skills application. Trying to learn a new way is hard enough, like selling before you build. When you’re also asked to apply that new way to something you care deeply about (your idea, your baby), it’s typical for your fears and anxieties to kick in — triggering your biases to hijack your thinking.

Instead, first learn and master the skill by intentionally building a safety net where it’s not only okay to experiment, but there are no dire consequences if you fail.


For instance, instead of interviewing your customers where the stakes are high, practice your newly acquired skills on friends or even test your newly acquired skill on ideas other than your own. Once you’ve mastered the mechanics of the skill, muscle-memory kicks in when you apply the skill to your idea.

This is where we lean on the second prong.

2. Hold yourself externally accountable

The second failsafe against biases is building an external accountability structure where you rely on people other than yourself - your team, coaches, and advisors to keep your biases in check.

“If you want to go fast, go alone; if you want to go far, go together.” - African proverb


So far, we’ve covered two pillars of hacking expertise: practicing deliberately with a psychological safety net.

While these two pillars help improve your entrepreneurial thinking, the third (perceptual learning) enables you to kick your learning speed into high gear.

Pillar 3: Perceptual Learning (learn without thinking)

I saved the best for last. Perceptual learning, sometimes called “learning without thinking,” is how you shrink 10,000 hours of deliberate practice to 1,000 hours.

Here’s how it works.

Research shows that even experts often can’t explain how they do what they do. When a grandmaster sees a chessboard, the right moves appear. How do you teach that?

Here’s the uncanny bit: While teaching expertise is hard, expertise can be learned simply by watching experts at work.

It sounds bizarre, but numerous studies have shown this.

  • Young musicians who were asked to sample the works of great musicians alongside their regular, deliberate practice made significant improvements over others that just practiced.
  • The best way to teach photographers composition, like the rule of thirds, isn’t by teaching them theory but by showing them many good examples of the rule of thirds.

Our brains are pattern-matching machines that connect the dots in ways we don’t fully understand.

We don’t have to know how this works to reap the benefits.

The key is sampling lots of examples of good:

  • good Lean Canvases,
  • good “expert” customer interviews,
  • good product pitches,
  • and more.

Rather than giving you a list of do’s and don’ts, which only increases anxiety, sampling examples of good allows your brain to extract these do’s and don’ts more effectively.

Note: Examples of bad do the opposite. They make you worse at a skill.

Another place where you can apply perceptual learning is through the further deconstruction of skills into recipes, patterns, and mental models.

Patterns help codify problem-solving techniques from the past so that we may apply them in the present.

We use patterns everywhere - in design, architecture, science, and software… so why not in business?

“If I have seen further, it is by standing on the shoulders of giants.”
- Sir Isaac Newton

You can become a student of patterns and mental models for things like

  • finding prospects,
  • building MVPs,
  • crafting offers,
  • testing marketplace models,
  • testing pricing,
  • and more.

When faced with moving your idea forward, these validation patterns serve as a catalog of possible recipes to help you get started.


To summarize, you can more quickly gain mastery of any skill when you apply any of these three learning hacks, but you can significantly accelerate mastery by combining all three:

  • learn by doing the right things (deliberate practice),
  • push beyond your edge (psychological safety), and
  • learn faster (perceptual learning).

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