I’m still at Lake Chelan. It’s another peaceful morning on the lake; a quiet Saturday morning. It’s been a great week. I’ve worked most of the week, but have really enjoyed having the family together. This is the most time we’ve all had together in several years. Lots of smiles, sunburn, and sailing.

Sailing is one of my favorite recreational sports. I learned how to sail at Camp Steiner, a Boy Scouts of America camp in the high Uinta’s in Utah. They had a small fleet of single person sailboats. Just the perfect size for two young teenage boys. My buddy Mark and I would hop on a sailboat late in the afternoon as the wind would pick up ahead of the thunderstorms that almost always blew through later in the day. I fell in love with the feeling of the sail cutting through the wind and pulling us across the lake.

20 years later, I purchased an Olympic 420 from someone in San Diego. He drove it to our home in Phoenix and sold it to me for $500. It was Sail ready. Maybe he wanted to make sure it had a good home, but it was an amazing deal.

I had purchased the 420 ahead of my first Intel sabbatical and our plans to spend a month at Lake Chelan. That boat was awesome. It was super light and fast and could turn on a dime. It was an old boat and was missing trapeze rigging. But it did the trick. I spent the month buzzing around on the lake learning the subtleties of sailing and turning into the wind, downwind, flipping it over, righting it back up and going again. My nephew Jeremy was my sailing buddy and the whole experience bonded us together for life.

With just a week left for me on the lake, a BIG wind day tempted me and Jeremy onto the lake. One of my measures of a sailing buddy is their comfort and willingness to ‘sail on the edge’ and even flip the boat, right it back, laugh, high-5, and get back into the wind. I can still enjoy sailing in calm winds for a casual glide across the lake. But not everyone is comfortable with the idea of flipping over. I guess it’s an acquired taste.

Earlier in the month, I had bumped into the cement dock and poked a small hole into one of the fiberglass hulls. The 420 has two airtight hulls on each side to ensure buoyancy. A bit of duct tape on that old boat did the trick (what else was I going to do?), and the little boat was back in business.

But, that day, the waves were big and the wind was big. Jeremy and I were sailing on the edge. Without a trapeze to balance the wind on the sails, we were in the water as much as we were in the boat. Flying and flipping. It was awesome. After an hour of fun, the hull with the duct tape had taken in so much water that it was sloshing around and eventually the boat wouldn’t sail upright anymore and we found ourselves at the mercy of the wind and 3-foot waves bouncing along as the wind and water thrashed the boat even worse.

We were eventually rescued. That’s a longer story than I want to share today, but let’s just say that the conditions on the lake had worsened and the few boats that were watching us fly by earlier, had retreated to their houses and we were alone out there for a few cold hours. The boat was trashed and I gave it to a family friend who intended to repair it.

The next summer, I couldn’t imagine being back at Chelan without a sailboat, so I hunted around for a Hobie Cat 16 and eventually found one near Sacramento. Mat and Mer (Bev’s sister) trailered it back to Washington on their return from Disneyland and I was back in business. AWESOME!

If you haven’t sailed. Let me just pause and tell you. TRY IT! It is truly awesome. Everyone seems to be looking for a way to jump onto a bigger, faster motor for fun, and the joy and art of sailing has become a bit lost with the thrill of speed. Don’t make the mistake of thinking sailing is a slow sport. Yes, it can be calm and quiet. But when the wind is blowing, it’s wildly intense and loaded with every bit of adrenaline as motorsports. Maybe more. In some ways, it’s even more exciting because the often unpredictable environment is more of a factor in the dynamics of motion and fun.

A single hull sailboat, like the 420, is super responsive and fun. The catamaran is built for speed. It’s a bit tricky to turn, but dang it’s fast. When the wind is blowing you can get 1-2 people on the trapeze and scream across the lake. That can turn into plenty of fun, and excitement… and surprises. There’s nothing like the feeling of flying across the water, one hull in the air, as you lean out onto the trapeze wire to balance the boat. Time fades away and you are entirely consumed by the moment.

This week, I’ve enjoyed some good evening winds and some great sailing with my wife and kids. On Thursday, I decided to risk going out solo. The main risk being – if the boat flipped, I wouldn’t be able to right it alone (it usually takes 2) and our ski boat has been acting up, so a rescue would be a problem. As I walked out to the sailboat, I notified my kids that they may need to canoe out to rescue me if I ran into trouble. Not ideal, but I couldn’t miss the chance to solo with this wind. Just me on the boat would mean more speed, and I wanted to be on the trapeze.

Oh yes. My other last words were me suggesting to my wife that the high winds wouldn’t be trouble for her drone. Put it out. Take some pictures. “Do you love me or, your drone more?” That was one of the dumber things I’ve done. She knew it was a bad idea. Separate story, but trouble with the drone = one more thing to worry about along with wind, waves, sails, and ropes. I’ll skip all the gory details of the death of the drone, but I will say Bev proved that she loved me more than her drone. And I’ve already invested in drone #2. 😉 That’s really the only way to truly say, “you told me so.”

I went out (across the lake) and back, and out and back again. Flying, nearly flipping. Then on my final approach to the lake house. I saw Bev on the dock with her phone (photo moment), so I figured I’d get aggressive on the sail for a great picture.

I’m not entirely sure how it happened, but 40 feet from the dock and the hull lifted out of the water below me. I was looking straight down the tramp (deck) of the boat to the water. Mind you, this all happened VERY FAST. And my first thought was, ‘after all that, I’m going to flip my boat right here? In front of the cabin. Nice for a rescue, but…. How embarrassing?!’

Somehow as the boat lifted, I was able to release the mainsail, shift my weight (say a small prayer), and adapt. In my early sailing days, I would have jumped off the top hull and accepted defeat. After all, the boat had essentially tipped over. But over the last few decades of sailing, I’ve learned a few tricks.

To my surprise, almost as quickly as the sailboat tipped, it responded to my weight and the decreased wind on the sail (laying flat with the wind), and the sailboat dropped back flat into the water. With some quick help from my wife and kids, I was able to dock the boat, drop the sails and swim it over to the beach (I was too close and wrongly positioned for an elegant landing). No harm, no damage (aside from drone #1). Home safe.

For the last few days, I’ve had flashbacks of looking down the tramp of the sailboat into the water. How quickly things went wrong. Trying to remember what I did that led to such aggressive tipping of the sailboat. I can’t remember. Other than, I was thinking about the camera in Bev’s hands rather than the boat’s speed, position, wind, and ropes in my hand. Maybe a bit of pride, and wanting a sweet pic to share with friends? Distracted. And in the spirit of funny. Not funny. REALLY FUNNY. Bev wasn’t even taking pictures, so there’s no photo evidence of my wild ride.

I’ve considered that moment high up above the water, watching the mast dip into the water and realizing it was too late. Why in my early days would I jump off at the last moment and abandon the last moment to recover?

Don’t get me wrong. No doubt, there are times in life when it’s smart to be aware and jump early. But there may be even more times when it’s better to be patient and persistent. The winds shift, the sun rises, and the moment passes. Where are you when that happens? If you’ve jumped too early, you’re in the water, unable to recover or contribute (as easily) to improve the situation. But if you can hold on into that often scary, and uncertain moment, you can lean into the newly found opportunity, recover and silly enough even look like a genius sailor.

No, I still don’t know exactly what happened. But the whole family was watching and decided the maneuver was a result of my skill and not my dumb luck. Who knows? Maybe a bit of both.

In 2009, I faced a similar situation when my company Omniture was purchased by Adobe. After several weeks of uncertainty, Adobe issued me a transition termination notice. They asked me to stay and assist with the transition and they would pay me a bonus. But, in the end, I’d be out of a job either way.

A good friend encouraged me to hold on. Don’t jump. There’s more opportunity in these transition moments than you’d imagine. And, just like that pivotal moment on the sailboat, I stayed on in those highly uncertain moments. I decided to focus, contribute, and do everything possible to help the transition be a great success.

Within weeks (moments in corporate life), they recognized my capability, encouraged my work, and the leadership team invited me to stay and offered me a formal position. That led through an amazing sequence of events that within 2 years put me as the head of procurement at one of the fastest-growing software businesses of the last 10 years. Because I held on, I was blessed with leadership, learning, and awesome financial opportunity. That positioned me in many ways for the ability to found my own business and create Graphite Systems.

Again – there are times to jump (even early), and there are times to hold on. You’ll need to make those decisions. And they will often happen under conditions of high stress and uncertainty.

Like my evening acrobatics on the lake, my career may lead you to believe my decisions were anticipated, planned, and the result of a genius life/career plan. Nope. But, at the same time, I don’t  believe it’s dumb luck. It’s extremely important to be aware (as much as possible) of the environment around you. But it’s crucial to also surround yourself with trusted advisors who can see your situation from a different perspective.

One more lesson to consider.  Avoid jumping quickly into a decision (unless you are in real danger) when you are feeling like a genius or an idiot. More likely than not, you’re not as talented or stupid as you think. We often take credit for the really big highs and the really low lows in our life. More than likely a gust of really good/bad fortune in your environment has largely contributed to your situation. Those are not the moments to be making life-altering decisions. Hold on (if you can), ask for advice to help you get through the moment and delay the big decisions to a moment when your mind is more calm and clear.

It seems totally rational at the lows when you can see things falling apart. However, it’s equally true during the high-highs. Don’t allow yourself to be tempted into believing you’re an amazing genius. I’m sure you’re talented, but step back from pride and arrogance, and wait for a calm clear mind before making big decisions.

And… get off that jetski for 30 minutes and learn to sail.