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The Art of Realistic Goal Setting

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Ed. note: Former ambassador Shawn Forry knows a thing or two about goal setting. He and partner Justin Lichter were the first to ski the Pacific Crest Trail (2015) and that's just one of his many successes. That's why we're republishing this popular post from 2016 on the art of setting goals (and working toward them!) 

Cover image: Taking the long view when setting goals is a surefire way to succeed. All images: Shawn Forry

New Year’s. Seems so long ago, that time of nauseating excitement punctuated by hope and aspiration. It’s when we wiped the slate clean, reflected internally, and strove for personal growth and achievement. The hands of the clock collided upon the stroke of midnight, the air was full of shimmering glitter, and we once again found ourselves committed to another year of exercising more, eating better, and flossing daily.

So why am I talking about something that has happened almost six months ago?

It’s time to check in.

And to consider why, in the span of a single night, we place unrealistic expectations upon ourselves and the coming year. It’s as if the year itself will control our fate and unveil the change we seek before us.

Despite best intentions, why does this trend continue to manifest? I’ve put a lot of thought into this recently, particularly how it has related to the success and failure that lies within distance hiking.


For most aspiring thru-hikers, the declaration to hike a few thousand miles into the unknown is our ‘New Year’. It’s the social equivalent to personal accountability.

The difference is that action is almost immediately put into practice; guidebooks are purchased, notice with employers is submitted and the fever of gear research begins. Eventually the long awaited date we’ve marked on the calendar with a big ‘X’ arrives and we are thrust from the planning phase into the doing phase.

For most, there is an awkward transition to settle into the daily routine of trail life. This transition phase is of utmost importance to recognize and honor. It’s the conscious choice of the life we are leaving behind and the one we are stepping into.

Herein lies the success to lofty goal setting: making the conscious choice to restructure our daily routine for the sole purpose of the physical and metaphorical incremental steps towards this overarching goal.

When else in our lives does every waking moment and effort go into serving a single objective? The act itself fuels a positive feedback loop of sorts. The more you commit to the routine, the more progress you feel, which directly translates into an aura of success. I personally think this a contributing factor to the elated, out-of-body feeling distance hikers often reference.

So what is the take away here?


Obviously we’re all not aspiring trekkers in the making. The point is that successful goal setting lies in the conscious choice to give something up from the past and the commitment to a new routine.

No goal can manifest itself without this give and take of daily rhythm. The motivation for the goal will arguably always be there but success will fall to the incremental shifts me make to our routine. Soon you’ll find yourself waking up an hour early for a run, taking that Friday night cooking class, and leaving the floss by the bed at night.

Shawn Forry is an adventurer, writer and outdoor educator with Outward Bound. With over 20,000mi of wilderness experience, Shawn is best known for his landmark treks of the Great Himalaya Trail, unsupported speed record of the Colorado Trail and most recently, the first successful traverse of the Pacific Crest Trail during winter. Shawn has been using Oboz footwear exclusively since 2010. More info can be found at

At the heart of everything we do are the folks who make the magic happen. A group of likeminded footwear-industry vets who left our big-brand jobs back in 2007 intent on doing business a better way. 

Men's Wind River III Waterproof
MSRP $210.00

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