Optimization vs. Exploration

Over the past year I’ve had what I’m labeling as a slightly-less-than planned year-long sabbatical. During this time, I've learned to appreciate the thrill of daily unpredictability. I would wake up with the globe as my playground—no office to commute to, no tight schedule, few places I had to be, and little to no rigidity in my agenda. The digital nomad life is tempting, offering boundless freedom and a multitude of experiences.

But while I also love the flexibility of finding what’s out there, I also have an itch for optimization, an desire to make the most out of every situation. I have been discovering lately that these two philosophies feel at odd with each other.

I’m grateful that I have a lot of flexibility with how I can spend my time, and I recognize that it’s a privilege to have the freedom to explore seemingly endlessly, but I’ve been coming to terms with the fact that infinite ability to wander for too long is not a good thing.

Since my move to New York, this challenge has escalated. The city is an ocean of choices: gyms for my daily lift, WeWorks everywhere, and a mind-boggling array of places to eat. It feels like I'm simultaneously a tourist and a resident, navigating an endless city every day. I've been living super flexibly, always ready to pivot my plans, and the flexibility has been something I’ve been very grateful for.

Living a life that allows me to explore has been satisfying by being able to jump on a short time horizon to whatever feels like the best move, but I’ve become aware that this hasn’t led to a solid long-term strategy.

With all of this I wonder whether a life of optimization is fundamentally at odds with a life of exploration.

On one side, the explorer in me gets a kick from discovering a new hidden gem of a place I’ll likely want to revisit, even if not for another month or year or two. But the optimizer—the maximalist—wants to dial in every detail, from the best gym location to the least crowded WeWork, and even maximize my routine and route of getting there.

In engineering, you wouldn't start a project without a well-defined list of requirements. Life, especially one committed to exploration, doesn't afford that luxury. Attempts at optimization without these boundaries end up being futile.

I've lived this, treating each hour as an open-ended scenario and rarely planning more than a couple of days ahead, and after having done it for a while now, I am discovering that too much exploration without routine makes it difficult to be fulfilled.

While lately I've been gravitating toward more structure, I realize that to optimize, I need to set some constraints. As I navigate the variables in this chapter of my life, my focus is on identifying what really matters to me. These constraints will be the guideposts for living an optimized life.

But even as I aim for a life measured in metrics and efficiencies, I can't overlook the importance of exploration. Being new to New York, I have to venture out to understand myself in this setting. There are reasons I chose to make the move here, and those reasons reflect the traits I’d like enrich in myself. My hope is that these explorations will further inform the framework within which I can start optimizing, yet optimization seems to happen when you are more specific about your routine.

What makes this all more complex is that many of life's 'requirements' are not clear-cut. Is it better to have a salad or halal food for lunch? There's no straightforward answer, even when trying to maximize. It's a mix of preference, health goals, and perhaps even the mood of the day. And how important is it really to try to get the best thing for lunch?

So maybe the tension between exploration and optimization is not a drain but a kind of nudge. It's a signal to reflect on the objective with a phase of life. Are you choosing to explore or to optimize? Trying to do both requires a lot of wasteful energy, like designing something without requirements, because you’re either trying to explore and then optimize in the moment, or you’re trying to optimize and then explore. And oscillating between both for a short-term decision just means expending energy on something fleeting.

In other words, you’re narrowing your scope at the wrong moment for smaller, tinier problems rather than taking a longer-term strategic approach of gradually sheperding the possibilities of how you conduct yourself over a much more generous length of time.

Flipping the switch from explore mode to optimize mode requires an interim rhythm and the discipline to find that. I’m hoping this acts as a reminder to me that to really make the most of a situation, it’s important to commit to it and see it through.

There’s something painful about writing this out because it feels like I am forfeiting the flexibility I entertained for such a long period of time. But I think at this point flexibility has started to merge on aimlessness, and that is a feeling much worse than being reflective and disciplined in determining what I need to do to kick start the process of creating my post-sabbatical self.

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