Mindful Detours

How long should we stay in New York?

This was the question we pondered while on our summer road trip last week.

We drove from Florida to New York and then back to Florida. We originally planned on visiting Boston after New York, but decided to extend our time in New York. While we’ve never been to Boston, we love New York, and knew it needed more time to show our kids all the wonderful places the city has to offer.

We were at a hotel in Virginia, considering the question about New York. My wife spent a lot of time planning this trip. She timed the route, all the stops, and collected countless lists of places to eat, visit, and experience. It was a lot of planning.

But planning is just a thought experiment.

You haven’t actually done anything yet. No roads were driven; no hotels stayed at; no cities experienced. The entire activity of planning existed in our minds (and some Notion docs). There was a plan created in the process, but the plan means little once the trip (the work) begins.

That’s why we were questioning the plan.

While we both cherish detailed, hour-by-hour itineraries, we’ve learned to (sort of) let go of the unrealistic expectation that we can actually stick to one with young kids. Kids are, after all, the harbingers of uncertainty. Just when you think stasis is met, a biological signal is triggered in young kids to incite chaos. Plans be damned.

But this is actually an important lesson in preparation, embracing uncertainty, and trusting the feel of the situation.

Embracing Uncertainty

The more you do something, the better you get at guessing how it will go the next time. But, no matter what, a guess is a guess. This is true in road trips, building software, and any activity with unknowns. The more you plan, the more you prepare, but only when you embrace the inevitable uncertainty. No matter how much you plan, unknowns will be waiting for you as you execute the plan. The secret lies in embracing the uncertainty—that’s the element to plan for.

As Dwight D. Eisenhower said, “Plans are worthless, but planning is everything.” The planning process helped build useful context for the trip. We formed mental models about timing, locations, and routes. So when it came time to make a decision—to potentially deviate from the plan—there was relevant knowledge to pull from.

The plan, even more than a thought exercise, was an exercise in preparedness. It prepared us for the inevitable unknowns, like the extensive traffic we hit on the way back, or the collection of unplanned stops for bathroom breaks. Don’t forget about those Harbingers of Uncertainty, whether they’re tiny humans or the roadblocks, challenges, and complexities on your own path.

Planning is how you prepare. And preparation is a precursor for responding in real time.

Tuning Intuition

When it comes time to respond, you need a compass, not a roadmap.

Your compass is how you navigate your own journey. And it improves with experience. You can call it your gut, intuition, or feel of the situation. Semantics aside, this is how you leverage your own knowledge, experience, and principles to make decisions. The stronger your compass, the less susceptible you are to the dangers of the planning fallacy—the belief that planning will save you from the inevitable unknowns in the process.

Trusting our gut is how we made the decision to stay in New York and skip Boston.

We knew we wanted to maximize our time in New York, which immediately deprioritized Boston. Then we thought about the time saved on the drive back; and the amount of experiences we’d miss if we shortened the time in New York. The choice was obvious.

Despite data to the contrary, sometimes the best decision may not seem logical in the moment. But your gut is a data point and, I’d argue, the most valuable data point. You don’t want to say I should have trusted my gut, while lamenting a bad decision. Trust your gut, and build your own compass by understanding the decisions you make, why they work (or don’t), and lean on your principles first. Principles are those timeless personal (and collective) truths that help calibrate your compass.

Leonardo da Vinci said “Intuition requires cultivation,” which prescribes a balance of work, rest, and reflection. Ideas need to marinate, to mix with the diversity of experiences—the great alchemy of the mind. Intuition is not a magical gift, but a disciplined creation of continued iteration and cultivation. Gardening requires patience, observation, and letting things grow at their own pace. Like a gardener, you must know when to focus intently, and when to slow down and let the ideas simmer. All of this is in service of fine-tuning your intuition, which is a critical tool in the battle of uncertainty.

Staying Nimble

With the rise of AI, we’re in a time of great uncertainty. There’s no better time to focus on embracing uncertainty through mindful planning and adapting in real time.

Did we make the right decision to stay in New York and skip Boston? Absolutely! We had an incredible time in the city, the kids loved it, and we’re all still thinking about the experiences we shared. We planned, prepared, and adapted as events unfolded along the way. We trusted our gut.

You can choose to keep pretending life is neat and orderly and goes according to a plan. Or you can embrace the chaos of uncertainty, stay mindful in the present moment, and trust your gut to make decisions as you move forward.