Man sailing a boat.

For Life & Leadership: If You’re Uncomfortable, Good; Get Used to It!

This is Part 4 of a four-part series. All four parts were originally delivered as one talk at HYPE in Steamboat Springs and Winter Park, CO, on March 6 and 7, 2019. HYPE is an annual event, TED-talk-style, that “brings inspirational thought leaders” to the area. (I hope I lived up to the “inspirational” billing!) My talk was entitled The Way Forward: Rolling Stones and Sailboats–for reasons that will become clear if you read all four parts in the series.

The theme for HYPE 2019 was growth. My aim was to give the attendees four navigational aids to find “the way forward” through four difficult growth points in life. These navigational aids have helped me find “the way forward,” and I hope they help you, too.

I spent two years during middle school in Palos Verdes, CA, an awesome little community in the southern LA basin. One of the most exciting things we did as a family during those two years was sail from Long Beach harbor to Catalina Island, one of California’s Channel Islands and a popular tourist destination since the 1920s, when chewing gum magnate William Wrigley, Jr. began developing it. My mom, sister, and I were all new to sailing. My dad was the most seasoned sailor among us, with a newly-minted captain’s license as proof. From the sailing experience I acquired then and life experience I’ve gained since, a metaphor takes shape to illustrate our fourth and final navigational aid in this series.

Assuming the vessel itself is seaworthy, a sailboat needs a couple of things in order to serve its purpose: the forces of wind and water. These forces are essential, not optional. Without them, you’re not sailing; you’re just sitting on a boat. The fastest “point of sail”–i.e. the direction you’re sailing relative to the direction of the wind–is called a beam reach. On a beam reach, you’re sailing perpendicular to the wind, or across it. Often, a beam reach is the most direct way to get from point A to point B. It’s also the fastest point of sail. Simple enough, right?

The funny thing about a beam reach, though, is that it can make for especially rough sailing. The force of the wind blowing across the boat causes the boat to lean over (“heel over”) as the sails catch the wind and convert it into forward motion. The pulleys and cables and other rigging components pop and groan. The sails are stretched taut. The boat travels across the waves, so the bow digs into them, and spray flies across the deck. It’s wet, windy, and noisy.

As a rookie sailor, I remember the beam reach as an uncomfortable, stressful experience. It didn’t feel okay. Could the boat and the rigging take that kind of stress and strain? Would the boat flip over? Was it really necessary to stay on that point of sail? Why weren’t we doing everything we could to make it a more relaxed and peaceful ride?

A more seasoned sailor on the same beam reach, though, says, “We’re good! In fact, we’re better than good. This is the best way to sail to get where we’re going. And this is exactly what this boat is built for.” He might trim the sails a bit and adjust the point of sail a smidge to optimize efficiency, but the seasoned sailor knows that this is precisely how we need to sail to get where we’re going. He sees the wind and water as allies, not threats–necessary forces to get him where he wants to go.

Same forces of wind and water, same point of sail, same behavior of the boat in response to those forces–but two very different perspectives and experiences.

There is a much more relaxing point of sail: “Downwind” keeps the wind at your back. The boat runs with the wind and waves instead of contrary to them. The ride is quiet and smooth and doesn’t require much of the sailor. It isn’t often, however, that your destination and the direction of the wind match so that you can run downwind all the way.

As in sailing, so in life. Rarely (if ever?) do the forces in our lives–family, work, health, our own internal challenges, etc.–array themselves behind us and propel us on a relaxing “downwind” run toward our destination. Much more often, we find ourselves on a beam reach, sailing across the wind and into the waves, all of our physical, mental, and emotional rigging absorbing life’s forces in an effort to convert them into forward motion.

Some moments, on some days, I’m a rookie sailor on the seas of life, fretting about this and that and worried that my ship will flip over or I don’t have what it takes to maintain the beam reach I’m being called upon to sail. On those days, I just want to turn downwind, to relieve the pressure on my rigging and have some peace and quiet. On other days, in other ways, I’m more of a seasoned sailor–monitoring the wind and waves, trimming the sails and adjusting my course to sail a solid beam reach. On those days, the stress and strain of life produce more exhilaration than anxiety. I take the helm with greater gusto and determination and welcome the forces swirling around me as good and necessary to get where I want to go. The wind and the waves and the spray remind me that I’m alive–ALIVE–and I’m fortunate to be the captain of my own vessel on the wild voyage of life.

I go back and forth, and I think that’s pretty normal. But on the whole, if you graphed my overall trend through the ups and downs, I think I can honestly say that I’m becoming a more seasoned sailor. Some of that, at 45, I attribute simply to the passage of time. More of it, though, I attribute to the conscious choice I’ve made to become a seasoned sailor.

Because we really do have a choice, don’t we?

If we agree that the forces life exerts upon us are constant–only varying in intensity–and the way forward involves getting better at harnessing them rather than avoiding them, then intentionally trying to become a more seasoned sailor is the best choice. In the moment it might feel better and relieve some pressure, but if we make a habit of turning downwind whenever life’s winds blow, we get incrementally off-course. Incremental course deviations over time compound into major waywardness over the years. Trim your sails. Stay the course. Put in the time. Do the work. The seasoning will come.

It’s worth noting that there are times when it is best to let down the sails, anchor in the harbor, take on provisions, tend to repairs, and rest. There are also times when it’s wise to seek refuge because the wind and waves threaten to overwhelm you. Take a break. Sleep. Go on a vacation. Seek the counsel of a good friend, a coach, a counselor, a trusted spiritual advisor. Hike, walk, run, paint, read, refresh yourself. Part of becoming a more seasoned sailor is knowing when it’s time to head into the harbor.

Then, again, as in sailing, so in life: After time at anchor in the harbor, after you’ve re-provisioned or the storm has passed, set your sails and get back out on the wild, uncertain, and (dare I say it?) exhilarating seas of life.

Which sailor are you today–the rookie or the seasoned sailor? Which one are you becoming? Are you putting in the work? Are you putting your physical, mental, and emotional rigging through their paces–giving them a chance to do what they were made for? How comfortable are you with the wind and the waves and the lean of the boat and the strain of the tackle on life’s inevitable beam reaches? How do you relate to the forces at work in life (and they are many!)–as threats to avoid or welcome and necessary allies to propel you forward? How well do you hold a beam reach to get you where you’re going?

There’s no sailing without the forces of wind and water. And there’s no meaningful progress in life without discomfort.

If you’re uncomfortable, good; get used to it!* And grow.

*Thanks to legendary Navy SEAL (and one of my man-crushes–not ashamed to admit it!), Jocko Willink, for “If you’re uncomfortable, good.” (“Get used to it!” is my addition.) Learn more about Jocko here.