After I published a list of business and side project ideas, a few people asked: “Where in the hell do all these ideas come from?”
The short answer is time and consistent note-taking, but that doesn’t fully explain it. There are times when my brain is “firing,” and other times when it’s dormant. I’ve learned to understand what energizes me and nurture a spirit of discovery that is conducive to finding ideas.
What follows is a set of tools. You can call them habits, environments, or mindsets, but they all revolve around two creative forces: divergence and convergence.
Divergence is the act of imagining or generating new possibilities. It’s throwing sticky notes on a whiteboard, reading from a new genre, or visiting a modern art museum for inspiration. Convergence is clarity, focus, and decision. It’s meditation, editing a draft and seeing the message, or selecting the most compelling sticky note on the wall.
Each of these tools either enables divergence or convergence. The most magical can do both—cultivating newness while revealing patterns and solidifying liquid gold.
Questions
Questions are an art form, a creative act, and maybe the most universal tool for discovery.
They can be divergent and open-ended, prompting us to explore new terrain, or convergent and reflective, asking us to zoom in and clarify. They are a way we learn and connect with others, make sense of ourselves, and guide scientific breakthroughs. They are everywhere, yet hidden in plain sight.
I realized the power of questions several years ago and have been observing and studying them ever since. I listen for great questions in podcasts, look for them when I read, and discuss how they are used in therapy with my wife, a therapist.
When I’m writing, I outline with questions. When I’m ideating, I often start by brainstorming questions. In many situations, I’ve found the simple act of formulating good questions leads to interesting answers and ideas.
The next time you’re in a position where you are reaching for a new idea, start with questions and see what emerges.
Curation
Curation is how we feed our brains. It’s the information diet that passes through the squishy, pattern-recognizing blob in our heads and emerges as conscious thoughts, things we say, and artifacts we create. It’s the training set for imagination.
Curation is a habit, not a one-off. The process of constantly refining what you consume will eventually reveal what you find interesting (i.e., taste, identity). As a thought experiment, try answering these questions:
You have unlimited funds to build a museum designed just for you. What’s inside?
Imagine designing a personal algorithm to scan the entire internet — but it can only bring back things you find fascinating. How would you teach it what to look for?
If you want to spot or create original ideas, you need personalized inputs. Mine include:
Ecology and natural history books
Podcasts that search for answers to silly or ridiculous questions
Stories of civic engagement, specifically outdoor activities
Biographies of polymaths
Internet oddities and things created with a spirit of playfulness
Entrepreneurship stories or tech projects that show extreme resourcefulness
I’ve had side quests into mycology, Maine lumberjack history, the global waste trade, and metaphors. None of it really makes sense together, and that’s the beauty. You don’t have to justify your curiosity. Just follow it and let the patterns emerge.
When you revisit my list of ideas, they might not seem so surprising once you know the inputs. What are you feeding yourself?
Connections, Associations, and Overlap
In nature, the richest biodiversity lives where ecosystems meet—riverbeds in deserts, alpine meadows, the edge of land and sea. The same is true for ideas.
I’m not a blank canvas creative. My best ideas come from layering inputs that don’t obviously relate. I’ve pulled web design ideas from travel, used ecological metaphors in writing, and made maps that overlay breweries with trailheads.
Most of us think this way subconsciously. Our ideas emerge from a mashup of life experiences and inputs. Sometimes, they surface naturally. Other times, we have to stir things up and force new combinations.
That might mean stepping into an unrelated field, reading outside your usual genre, or going on a field trip. Or, take what you already know and try mixing it in ways you haven’t before. You can be strategic about what you’re intersecting or more loose and random. What’s important is that you’re asking things like:
What’s similar about these things?
What’s different?
What would it look like to combine them?
Does one thing help explain the other?
Watch any standup special and you’ll see this strategy at work. Comedy often takes one idea and drops it into an unexpected setting. John Mulaney’s Horse in the Hospital bit is a perfect example. Intersections like that hold the juice, spark weirdness, and hum with creative tension.
If you’ve been curating, you’ll have a lot of material to draw from. Find a flexible medium, like a whiteboard, throw the ideas up, and see what you discover by trying to connect them. Or lace up your shoes and move on to the next section.
Movement
If you work in a physical medium, like ceramics, field biology, or theatre, you’ll find the idea that movement can lead to discovery obvious. For the increasing number of us “knowledge workers,” aka brains mounted to bodies, it’s less obvious.
I’ve found two kinds of movement that spark discovery. The first is divergent—about covering ground, getting into a new space, and seeing with fresh eyes. This is my default. It’s why I take solo trips and do savage things like backpacking 30 miles in a day. If you're in a rut, try this kind of movement.
The second kind of movement is convergent. It’s slow and steady—the way of the pilgrim, yogi, or carpenter. You occupy your body with low-level effort and give your mind space to settle. Some of my clearest insights have come this way: canoeing across a lake, skiing wide-open trails, or hiking long distances on flat ground. My realization about the power of questions showed up on day five of a 10-day trek in Peru in my early 20s.
We can’t all take off on long pilgrimages, so let me condense down what works for me on a smaller scale.
A trail without a defined destination
Open views: hills, ocean, or even cityscape
A clear path with few obstacles
An activity that raises your heart rate gently, without heavy breathing or strain
If you're in Portland, Maine, the Eastern Trail across Scarborough Marsh, the Mackworth Island loop, or the fields at Gilsland Farm work beautifully.
Constraints
It’s hard to make discoveries in an infinite search space. When we feel stuck or stifled, our instinct is often to expand. We go full “eat pray love.” That impulse isn’t wrong, but big ideas can overinflate, drift out of reach, and leave us stuck where we started.
So yes, think big, but don’t overlook the creative power of limits. Constraints can focus your attention, lower the bar to start, and lead to surprisingly original ideas. Here are a few examples that prove creativity can thrive within tight boundaries.
How can I find grand adventures without leaving home? (Microadventures)
How do I start a business using someone else's waste? (Circular Economy)
How do I make magic with humble ingredients? (Southern Cooking)
If you’re feeling lost, try limiting your options. Shrinking the space lowers expectations, which makes it easier to start. Starting is often the hardest part.
When I was starting the Maine Outsider, I felt overwhelmed by everything it would take to design, build, and run a public newsletter. So, I stripped it back and sent the first three issues through Gmail to a small group of friends. Writing in Gmail forced me to be short, clear, and punchy. It helped me find the tone early, in a way I might have missed with the distractions of a full-featured newsletter tool.
The stripped-down version showed me it was fun, rewarding, and full of potential. As momentum built, I gradually relaxed the constraints and added new features, like maps for each event and a trail log where readers could share stories. I sent my 83rd issue this week.
Intuition, Risk, and Humility
Of all the tools, this one is the fuzziest. It leans into intuition, risk, and something that feels a bit like magic. I won’t try to pin it down. It’s too big, too messy. But I will point you to this short clip of Jon Batiste talking about his musical process, which conveys the idea well.
“Sometimes it tells you things you haven’t practiced. You don’t know if you can actually play. You don’t know if you’ll make it. But it’s the truest expression. The moment calls for what it calls for—and you can’t dictate that based on your preparation.”
It’s easy to dismiss this as something only a Juilliard-trained musician like Jon Batiste can do. But that level of skill can be its own trap. Reputation, mastery, and the pressure to always get it right can make exploration feel off-limits for both experts and beginners.
Batiste has the humility, flexibility, and awareness to play something unknown and respond to it. Others have described this same creative force in different ways: the Greeks called it the muse. Elizabeth Gilbert calls it Big Magic. Paul Millerd calls it the Pathless Path. David Whyte calls it conversational reality. All roads lead to the same idea.
It’s less about control and more about noticing when something interesting or beautiful shows up. This philosophy is freeing for someone like me, who tends to default to planning and optimization. Since leaving my job, I’ve been learning to trust this mindset—operating more by feel and letting curiosity lead. It’s taught me a lot.
The unknown is rich with possibility. Let yourself go there.
You might read this and think I’m a painter, musician, or theatre person. I’m none of those things (yet). I’m just someone who feels most alive when I’m exploring and creating. Sometimes, that takes the form of poetry or writing, but more often, it’s an idea that shows up on a bike ride or a question posed to a friend.
I write about this because I want more of it. I want to understand how my mind works and to put myself in more situations that spark this feeling. These tools—movement, curation, constraints, questions, and connection, help me stay open to new ideas. They’re how I create the conditions for discovery. Maybe they’ll help you do the same.
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Amazing 🤩