Comfort Zones and Where the Magic Happens

We construct stories and lives that define our comfort zones: “I’m good at this.” “I’m bad at that.” “I’m a writer.” “I’m a data scientist.” “I’m a realtor.” In this way, we tell our own story, and we write the next chapter, and the next, onward till the end. 

But comfort zones aren’t meant to be written in stone. They’re cozy plateaus and good places to rest along the journey, but if we linger too long, sooner or later a storm sweeps in or an earthquake strikes, and the safe environment we loved so much migrates somewhere else. Yes, even if we don’t migrate, the world does. And then we’re left in our former comfort zone, wondering what happened. 

Most of us realize the danger of stagnation, and it’s why we challenge our comfort zones occasionally, attending a new event or taking a course in a new-to-us subject or changing jobs. Those challenges keep us climbing, evolving, and changing along with our environment. 

Beyond Incremental

But there’s another kind of comfort-zone challenge: 

The first time I saw this idea drawn out¹, it resonated deeply. Getting to Where the Magic Happens doesn’t usually mean a straightforward hike to the next plateau, surrounded by likeminded fellow travelers, or a quick detour to a scenic lookout. Instead, seeking out that place means going off the map, with no clear sense of where the trails and pitfalls are. It can feel scary and disorienting, exciting and revivifying, or all those things at once. It’s also the path to innovation. 

So, what’s a good way to get there? This is a newsletter about risk, so I’m not going to be like, “Just jump off the cliff and see what happens!” That’s not a good attitude or approach, even when seeking out Where the Magic Happens. The magic doesn’t happen in a jumbled heap at the bottom of the cliff. 

Navigating the Unknown

The first thing to ask is, “Is it worth it to head off the map?” The answer will depend on the type of risk you’re facing, and the likelihood and magnitude of potential upside and downside (ideally, you’re looking for odds favoring the upside along with limited downside).

If you do decide to forge your own trail, here are some approaches I’ve found useful in unlocking unknown paths and managing risk along the way: 

• Do a lot of research. You may be thinking, “That sounds like a boring way to go off the map. Where’s the magic?” But to reach a new place, we need to understand what’s been done, and tried, before. What the open questions are. What questions might not have been asked or explored yet. 

• See if you can find a mentor who’s helped people travel off the map before. The other people your mentor helped may not have traveled to your specific desired destination (otherwise it would be on the map by now), but they likely faced similar emotions, challenges, and types of situations, and developed coping skills, strategies, and counterintuitive insights that could prove extremely helpful in your own journey. A mentor who’s seen a wide range of situations play out hundreds or thousands of times before can be a tremendous ally. The importance of this step can’t really be overstated.

• Combine two different disciplines. It’s much easier to blaze a new trail on fresh snow than on an interstate highway. And it’s easier to break new ground at the intersection of multiple fields, because there’s less competition and more fresh snow in that interstitial space.

• Combine persistence and adaptability. When you step off the map, you’re going to get lost sometimes. You’re going to feel frustrated, disheartened, and confused. You’ll need persistence to persevere through that. But sometimes it becomes clear that the path you’re walking isn’t leading toward Where the Magic Happens. What then? Persisting at something that clearly doesn’t work isn’t a good idea. The right move then is to persist by trying something different. If you don’t give up and you climb out of ruts, odds increase that you’ll find a working solution eventually. It might not be the path you initially envisioned finding—in fact, it usually isn’t—but that’s the adaptability piece of the puzzle. 

The Balance of Risk

Even if you do everything right, it is risky to try something new. But it’s also risky not to question, not to explore, and especially not to pursue something that feels right for whatever reasons you can define. The best ideas sometimes emerge from side tangents that seemed interesting for their own sake. Like Steve Jobs said, you can only connect the dots looking backward. Giving yourself permission to explore the not-immediately-practical leaves the door open for inspiration to walk through. Sometimes you’ll take a small detour and then return to a well-paved path; other times you’ll learn how not to do something; and other times you’ll set off on a journey into the unknown. 

One of the best and most exciting things about life is that we don’t have a map sometimes. In The Fellowship of the Ring, one of my favorite movies about two friends traveling off the map, Frodo and Sam are leaving the Shire on their quest, and Frodo reminds Sam of what Bilbo used to say:

“It’s a dangerous business, Frodo, going out your door. You step onto the road, and if you don’t keep your feet, there’s no knowing where you might be swept off to.”

Risk management doesn’t mean never trying something new. It does mean doing our best to prepare, seeking help when needed, and recognizing when to press forward and when to hit the brakes or change direction.

1. I can’t find the origin of this meme/quote, which has many variations; if you know, please tell me!