3 ways to know what skill to learn next


Hey Reader,

You ever wonder how some people just seem to speak in perfect soundbites? They always have the right thing to say, delivered in exactly the right way.

At our Craft + Commerce conference this summer, Tristan de Montebello from Ultraspeaking taught something called "The Accordion Method"—a technique for learning to speak this way by compressing your thoughts down to 30 seconds, then expanding them back up to 2 minutes.

Watching creators practice this made me think: Most of us are terrible at choosing which skills to learn next.

We pick skills based on what sounds interesting or what people say we should learn. But we don't have a good way to figure out what would actually move the needle in our business.

I recently had neuroscientist Anne-Laure Le Cunff on my podcast, and she has a solution for this. She calls it the tiny experiment approach.

Instead of setting a goal like "I'm going to get great at video editing," you run a small test: "For 14 days, I'm going to spend 30 minutes editing short-form videos to see if this is worth pursuing."

The key insight is that you learn by doing, not by planning.

But how do you know which skills to focus on? Which experiments are worth running in the first place?

1. Get specific feedback from others

Most feedback is useless because it's too general. Instead of asking "How can I improve?", ask specific questions:

  • "What's one thing I could do better in my presentations?"
  • "Where do you see me wasting the most time?"
  • "What skill would 10x my content output?"

You might think you're an amazing content creator, but after asking your team directly, you might hear: "We always do 4 takes of everything. If you could nail it in one take, we'd create so much more content."

2. Study yourself

Record yourself working. Watch it back. Review the data ruthlessly:

  • Where do you stumble?
  • What takes way longer than it should?
  • What makes you avoid certain types of work?

This is how deliberate practice works. You can't improve what you don't measure.

3. Pay attention to what smart people are learning

Follow industry leaders. What skills are they learning right now?

If you notice that 6 out of 10 successful creators are talking about learning the same thing, that's worth noting. They're probably seeing a trend before it becomes obvious.

A crucial note: You have to figure out what these are for yourself, but for me, some shortcomings aren't worth fixing. Being disorganized? I'd rather hire someone to organize my life for me. But struggling with video editing when your entire business depends on video? That's worth the investment.

The ego trap

The hardest part about learning new skills isn't the time investment—it's admitting you're not good at something. Your ego wants to protect you from feeling incompetent.

Everyone can see your weaknesses except you. And they're likely holding back your business more than you realize.

The next time you catch yourself avoiding a skill because it's not that important, ask yourself: Is this really not important, or am I just scared to be bad at something?

Pick one skill. Run a 14-day experiment. See what happens.

What skill are you going to learn next?


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Expert Coaching: How To Grow A $1M Membership Business In 2025

Today I’m joined by Rose Griffin, founder of ABA Speech, for a coaching session to map out how she can scale her $210k/yr business serving speech therapists and BCBAs to over $1M in annual revenue.

We break down how she built a 500-member community, the unique value of offering continuing education credits, and how group sales and direct outreach could accelerate growth.

We cover:

  • How she built 500 paying members
  • Her group sales scaling strategy
  • Building a business around family goals

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As we scale from product-led to sales-led growth, we need a strategic content leader who understands the unique challenges creators face because they've built their own business through social media. You'll own Kit's social media strategy and execution across LinkedIn, Instagram, TikTok, and X—creating content that drives both brand affinity and qualified lead generation.

The role is 60% execution, 30% strategy, and 10% internal collaboration. We need someone with 4+ years of social media marketing experience who has successfully monetized their own personal brand and can convert social engagement into qualified prospects for our sales pipeline.

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This video documents five years of rebuilding the American Hotel after it burned down in 2020. The original was built in 1871 and hosted everyone from Butch Cassidy to Mark Twain.

The logistical challenges are wild: hauling concrete up an 8-mile dirt road, moving 4,000 cinder blocks by hand… It really shows what it takes to preserve history in remote places.

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Have a great week!

—Nathan

Nathan Barry

I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.

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