My mind was completely blown. How is it possible that we are going downhill when driving from sea level up to a ski town?!? Is this like some crazy “the-Nile-actually-flows-north-alternate-universe” type stuff, or what?


My wife and I were driving with a friend from Vancouver to Whistler on the Sea-to-Sky Highway, which if you’ve never done it, is the most beautiful drive I have ever been on—ocean, mountains, giant green trees…remarkable. But my brain was convinced, absolutely convinced…so convinced that I actually looked it up on the Google machine, that somehow, some way, we were going downhill.


No need to Google it—I did. We weren’t. Whistler is ~2,200 feet higher than Vancouver.


Once my mind was assuaged to that fact, I turned reflective to try and discover how this Copperfield-like illusion was being pulled over on me. What I learned about that drive completely changed my life.


The Sea-to-Sky Highway has really long stretches of straight, seemingly flat road, followed by dramatic down hills with twists and turns around the mountain passes: flat, flat, flat, flat…DOWN, DOWN. Giving the feeling that over time we were flat at best, downhill more likely.


Not until I looked behind me through the back window did I solve the riddle. When I looked behind me, those long flat stretches were in fact really long, gradual hills climbing hundreds of feet at a time. It struck me that my journey as an entrepreneur and leader has gone much the same way.


The empty feeling of hopeless frustration. The empty feeling of running really hard but things not seeming to get any better, stuck on the treadmill of entrepreneurial hell. Pouring in everything I’ve got and more, but still the unnerving feeling of flat at best, downhill more likely.


In my life, success and progress have never come easily, nor in some seminal moment. It’s been a long, hard slog…slow and steady, looking ever forward toward my goals and vision. But the fires and the gut-punches? Those came with a fists full of fury. To this day, I have the emotional scar tissue to prove their ferocity.


Once again, it’s not until I take a moment—just a quick moment—to pause and look out the back window of my life (which is not an easy or natural thing for me to do) that I see the heights I’ve climbed and can truly appreciate the change in elevation.


I know what you’re probably thinking. Something like, “Yeah, but if I get content with what I’ve done, I may lose my motivation and my fire to keep pushing forward. I’m not one to rest on my laurels.” I get it because…yeah, me too. I used to think like that. An empty stomach makes for a more successful hunter, right?!? But remember when I said that drive changed my life? Here’s what I discovered that transformed me forever.


With those moments of reflection, I am now able to redirect the mental and emotional energy previously reserved for self-flagellation on what I woulda/coulda/shoulda achieved or done, to truly appreciating what I’ve accomplished (including surviving those downhill mountain passes), and what mountain I want to take on next.


Through those moments of reflection, I discovered a hidden treasure-trove of untapped confidence, motivation, and inspiration that propelled me forward at a speed I never thought possible—with a level of joy and fulfillment I had never experienced. Today, even when adversity rears her ugly little head (and she always will) I am emboldened by looking out my metaphorical back window and realizing the worst day today is still better than the best day a year ago.


Now, I routinely build “Elevation Marker” moments in my life: scheduled time for me to stop and look out the back window to check in on how far I’ve come. Times like when I write a quick “state of the union” reflection in Evernote at a conference I attend each year. Or when I go to dinner with my business partner and our wives at the end of every year to reflect back and celebrate the good, the bad, and the ugly. The quarterly retreats and annual reviews with my team. There are many opportunities to piggyback Elevation Markers reflection on your existing recurring events.


But I don’t just wait for events. Elevation Marker moments are celebrated when my wife, partner, or teammate when we start amazing conversations with, “Do you remember when we used to…” and take that moment to first, laugh…and then celebrate our journey, marveling at how far we have climbed. Taking that moment before turning back around with a little more determination, with a little more pep in our step, and with a little bigger smile on our faces, as we tilt our heads up and tell that next mountain “Here we come!!”


Where in your life does it feel like you are stuck on the treadmill, not making progress? Take a moment to look at the elevation markers out your back window to see if you may in fact be a couple thousand feet higher from where you began your journey. Make sure you take just a quick moment to appreciate all you’ve done to get to where you are and prepare you for where you are going.

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