Published in Career Advice

Jonathan
The Effective Project Manager
February 23, 2025
Collecting Dots. The One Skill That Trumps All Others.
Success isn’t just about mastering one skill—it’s about collecting diverse experiences and connecting them in unique ways. Steve Jobs saw it. Dharmesh Shah embraced it. David Epstein proved it. The most successful people cultivate range, integrating knowledge from different fields to create breakthroughs. Start collecting your dots today—because your future success depends on it.
Steve Jobs (Apple visionary) famously said that you can only connect the dots looking backwards, not looking forwards.
Dharmesh Shah (founder of Hubspot) took it a step further. Advising that you should be “a collector of dots”.
David Epstein (author of Range) said that your goal should be to cultivate a wide variety of skills (have a wide range).
What these thinkers are telling us is that success is highly correlated to how broad your knowledge is, and how well you can integrate seemingly-distant ideas.
Cultivate range (collect dots) in your life, because your success depends on it.
The Hidden Pattern of Success
Most people think that becoming really good at one thing is the key to success. But some of the world's most successful people say something different: the real key is collecting lots of different knowledge and experiences.
Think of your mind as a vast night sky. Each piece of knowledge you gain is like a new star appearing. By itself, each star is beautiful – but when you start connecting them, you create your own constellations of ideas that no one else can see.
Looking Backward to Move Forward
Steve Jobs understood this perfectly. He said you can only understand how different parts of your life connect when you look back at them. It's like being a detective who finally sees how all the clues fit together, but only after gathering them all.
In college, Jobs took a calligraphy class just because he found it interesting. Years later, that seemingly random interest helped Apple create the first computer with beautiful text and design. That single dot of knowledge merged with technology to change how we interact with computers forever.
The Collector's Advantage
Like Dharmesh Shah, imagine you're building a massive LEGO collection. But instead of plastic bricks, you're collecting pieces of knowledge. Each piece might seem random on its own, but together they let you build things no one else can imagine.
The Mathematics of Ideas
Think of mental-connections in mathematical terms. Your collection of knowledge works like a spider's web. Each new idea you learn is like adding another anchor point for the web. With five anchor points, you can make ten connections. But with ten anchor points, you can create forty-five connections! Your web becomes exponentially more complex and capable of catching new ideas.

Building Your Collection
Here's what you can do this week to start collecting dots:
Read differently: Pick up a magazine you've never read before. If you usually read about tech, grab National Geographic. If you read about sports, try Scientific American. Spend 15 minutes each day reading something completely new to you.
Watch differently: Instead of your usual YouTube channels, watch three videos about how things are made. Learn how guitars are built, how glass is blown, or how bridges stay up.
Listen differently: Try one new podcast from a different field. If you're into business, listen to a history podcast. If you like science, try one about cooking.
Talk differently: At lunch, sit with someone who has a different hobby than you. Ask them what makes their hobby interesting. What keeps them excited about it?
Make differently: Pick one small project outside your comfort zone. If you're good with numbers, try drawing a comic. If you're artistic, try writing a simple computer program. Give yourself permission to be bad at it.
Learn differently: Use free online tools like Coursera or Khan Academy to take one lesson in a subject you know nothing about. Spend just 30 minutes learning the basics of architecture, astronomy, or anthropology.
Write differently: Keep a "dots journal." At the end of each day, write down one new thing you learned and one weird way it might connect to something you already know.
These are small steps that take 15-30 minutes each. Try one this week. Next week, try another. You're not trying to become an expert – you're just collecting interesting ideas to play with later.
Accelerating Your Career Path
Every skill you collect becomes a career multiplier. That project management experience combined with your interest in behavioral psychology helps you lead teams in ways others can't. Your deep industry knowledge paired with that data visualization course means you can present insights that others struggle to communicate.
Think about your last three roles, side projects, or hobbies. Each added a unique tool to your kit. When others get stuck thinking "That's not my job," you can step in with solutions pulled from different domains. Maybe you're the sales leader who understands the technical backend, or the financial analyst who knows how to tell compelling stories with data.
The formula is powerful: Core expertise + Diverse skills = Solutions others never see coming. In a world of specialists, being a skilled generalist makes you uniquely valuable. While others climb straight up, you can move in any direction.
The Invitation to Explore
So when you feel pulled toward something new – whether it's learning about deep-sea creatures or trying your hand at digital art – follow that curiosity. Each new exploration adds another dot to your collection, another star to your constellation, another color to your palette.
Remember: Where most people are digging one deep well, be the person who explores the whole landscape. Your unique map of connections might just lead to treasure no one else can find.