Winging It, Gracefully

Ever watch the sun go down and realize you’ve forgotten your headlamp?

I’ve been thinking about the difference between planning (be back to the trailhead before dark) and preparation (pack a headlamp just in case). One has the potential to hold us back; the other might just set us free.

Preparation accounts for various possibilities. It recognizes more than one possible outcome to a situation. Good prep considers what COULD happen, and tries to ensure sure you have items or steps or strategies in place for the unexpected.

Planning, when too strict, not only limits your achievement, it can also shackle you when things go wrong. Sticking to the plan is important when things are going smoothly – but what if the plan has to change on the fly? Can you handle speed bumps? Do you have a plan B? What about a plan G?

My dog and I set out for an evening hike in our hometown of Bozeman, heading north towards the ridgeline of the Bridger Mountains, our goal the scree-covered summit of Baldy. We started up the trail with the blue sunny skies of a typical Montana afternoon beckoning us upward. This particular afternoon happened to be daylight savings – clocks would fall back an hour. That morning, in a haze of extra sleep, I’d concluded that we’d have an extra hour of sunlight in which to top out then turn around. Dutifully, I packed my “just in case” headlamp and jacket, confident that the additional daylight would negate any need for such items. It wasn’t until we hit the second big knob on the ridgeline that I began to recalculate.

Looking north toward the final push in the gathering dark.

The summit popped into view through the trees. I looked up at the gray mass thrust into the darkening blue, still about more than a mile and 1,000 vertical feet from we stood. Hmm, I thought, looking west. The sun’s going down quicker than I thought. Checking the time, I realized my total misreckoning. We’re about to be on an exposed ridgeline in the dark.


Turn around or keep going? I’m a sucker for mini-peril, so Adventure Mutt Zoe and I hustled onwards up the ridge. It wasn’t long before I had to extract my headlamp from my small pack, and by the time we hit the top, we were both completely reliant on the light from the headlamp to illuminate the trail.

Hey there, summit cairn! Nice to see you.

Hey there, summit cairn! Nice to see you.

Thanks to sufficient preparation, we were able to finish the hike to the top and make it back to the car safely. But my planning was woefully inadequate. If not for the addition of a few seemingly-excessive supplies, we would have been screwed—parts of the trail require careful steps even in daylight, located just a foot or two from the edge of cliffs and steep slopes. And even if we’d turned around right when I realized my timing mistake, there’s no way we could have made it all the way down the trail before dark.

Now, big shout-out to plans, in general. I don’t want to make it sound like I believe in constantly flying by the seat of one’s pants. Carefully considered and with room for improvisation, good plans are critical components of the bulk of our achievements. But too strict an adherence to what we expect will happen is not only limiting, it’s downright dangerous.

Instead of planning out your every move, try this instead: have a tangible goal in mind and tackle it with enough preparation in your back pocket to either (A) press on or (B) jump ship. But keep it fluid. Make your decisions based upon the way internal and external conditions transpire – not on a strict and unchanging plan. That way, if something incredible – and unexpected – happens to cross your path, you’re free to chase after it like my dog after a squirrel. And if things go wrong, well, at least you’ve got your headlamp.