Skip to content

Reasons to be oppressively optimistic

Elysha has claimed that I can be “oppressively optimistic” at times.

I’ve also been known to make certain people’s eyes roll when energetically asserting that “Everything’s going to be great!”

“I’m fantastic.”

“Fear not! All will be well.”

Elysha isn’t entirely wrong, of course. I most definitely lean toward optimism in most things. But perhaps it’s merely a case of perspective. A choice of what to see and remember.

Case in point:

Elysha and I celebrated 15 years of marriage by spending last weekend on Martha’s Vineyard. It was a fantastic three days, marked by, among many others, these three moments:


When Elysha and I arrived in Edgartown, one of five towns on Martha’s Vineyard, on Friday afternoon, the power for the entire town was out.

Of course.

After dropping our bags, we made our way to a place to eat called The Seafood Shanty – a restaurant on the water – but because the power was out, the host wasn’t seating guests. We waited a few minutes and were eventually advised to go to the second floor of the restaurant and see about being seated for drinks until the power was restored.

Because they had been turning people away because of the outage, Elysha and I managed to land the very best table in the place, on the railing, center of the patio, overlooking the Edgartown harbor.

The power came back almost immediately, so our dinner arrived on time, but the power outage had fried the restaurant’s computer system, making it impossible to process our check. This allowed us to remain in this prime location for much, much longer as restaurant managers attempted to reboot their computers. It was a perfect storm of problems that allowed us to enjoy the beautiful scenery of the harbor and each other for much longer than would otherwise have been possible.

Eventually we paid for our meal the old fashioned way, with carbon copy on an ancient, sliding credit card machine.

It was our favorite meal of the weekend.


On Saturday, our concierge recommended the Jaws tour of Martha’s Vineyard. Visit the shooting locations of the famous film and watch the segments of the movie associated with each location on an iPad. It sounded fantastic. I am obsessed with this film. I’ve read Peter Benchley’s book many times, watched the movie many times, and studied the history of making the film via books and DVD commentary.

Elysha was so excited for me.

When we logged onto the website to book a tour, we found that they were sold out.

Of course.

After some hemming and hawing, we decided to look into the three hour personal tours of the island that the company also offered. Eventually we boarded a van driven by a man named Jim who regaled us with incredible stories, incredibly told, as we toured the island. In just over three hours, we had traveled to every corner of Martha’s Vineyard, hopping out at scenic locations, and having a truly grand time.

The Jaws tour would’ve been great. Jim’s tour of the island was probably better.


Sunday morning, I was sitting outside our room, on the deck, enjoying a beautiful sunrise as I wrote and revised my latest book. I worked from 4:00 AM until about 5:30 AM when the clear skies were suddenly filled with clouds and a thunderstorm erupted almost instantly.

My productive morning was ruined as I fled into our room and out of the rain.

Of course.

Instead of pecking away quietly on my keyboard as Elysha slept, I did something I never do:

I climbed back into bed with Elysha, holding her tight, and falling in and out of sleep for more than an hour.

It was one of the best parts of the entire weekend for me.

Maybe the best part.

By the time we were packed and ready to leave the room, the storm had passed. Skies were clear again. The sun was shining.


Things don’t always work out. Problems arise and remain unsolved. Disaster can strike at any moment. The world can be a messy place.

But a lot of good things happen in this world, too. And quite often, potential problems – a town-wide power outage, a sold-out tour, or an untimely thunderstorm – can become something unexpectedly wonderful.

I make a point of noting these moments whenever I see them. Remembering them. Sharing them with others.

Perhaps this is the reason for my oppressive optimism:

While so many people seem to take enormous pleasure in lamenting the drama and difficulty of life, filling their life with grousing, complaints, and concerns over small bumps and petty injustices, I like to keep a weather-eye on these turnaround moments, like the ones I experienced in Martha’s Vineyard last weekend.

Optimism begins with reasons to be optimistic. It grows when you allow yourself to seek and find these moments – large and small – in your life. Optimism flourishes when you steep yourself in the memories of glorious moments like these.

And yes, optimism can perhaps become slightly oppressive when you constantly tell yourself the stories of these turnaround moments that started out poorly but quickly turned wondrously wonderful.

Without much effort, you can find yourself constantly thinking that if it’s happened before, it can happen again.

“Everything’s going to be great!”

“I’m fantastic.”

“Fear not! All will be well.”

I have to say: It’s not a bad way to be.