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  • By Theodore Lewis

Lessons for Everyday Life: It always pays to plan

South Portland, Maine — In 2016, after 20 years of work experience and success in the C-Suite of several large healthcare organizations in the U.S. mainland as well as in Guam I found my career and life in an unusual and unanticipated predicament: out of work.

Sometimes unfair things happen in life and faced with the stark reality of being falsely maligned and discriminated against because of whistle-blowing, one has no choice but to do what one needs to do to survive.

So, in 2016 after being unwelcomed from Guam, I returned to Maine and signed up as an Uber driver to help pay the rent.

As I began to Uber I quickly realized that many principles that result in success in the C-Suite and in life, are also at play in the Uber environment.


It was Thursday, Dec. 29 and Portland Maine's weather started off in the 40s. The weather forecast for Maine had been calling for a nor'easter to arrive late in the day with heavy snow to develop in the northern part of the State first.

My plan had been to Uber from 5 p.m. to about 10 p.m. Just before heading out I checked for an updated weather forecast and learned that a band of very cold air from Canada had entered the storm pattern and the temperature in Portland was predicted to go below freezing around 10 p.m. with 4-8 inches of snow now expected by morning in Portland.


My wife Sharon asked me if I had purchased a shovel and salt for my car yet and I replied no. On my way out she suggested I make sure and take my gloves, boots and a hat. I grabbed my gloves but decided that I would be coming in before the snow so no need to take my boots.

I signed on with my Uber app, and received my first ride request at 5:31 p.m. I began to pay attention to the temperature gauge on my dash and during the next three hours as I completed seven rides, the temperature hovered between 37 and 39 degrees. A light drizzle of rain had begun to fall.

On my way back from Gorham, I signed off with Uber as the roads outside of Portland were getting difficult to traverse. As I was signing off, I noticed the dark red color shades developing on the Uber map. Shades of red indicate there are not enough drivers for the rider demand and the prices for rides go up for the riders in those locations (the darker the red the higher the price multiplier).

I began to think about the many people at restaurants and bars in the Old Port (the waterfront area in downtown Portland where most of the popular bars and restaurants are located), who need a ride home and would happily pay 2, 3, 4, or 5 times the normal rate for a ride right now.

It was not a long debate I had with myself and about 11:30 p.m. I signed back on.

At 11:36 p.m., a ride request popped up in my Uber App. from 1170 Forest Ave. Unfortunately, the request was from an area outside of the surge locations. I made an executive decision to accept the ride.

The pick-up would be for a Christopher. While waiting for Christopher, I put on my coat and gloves to clean off my windshield and wipers that had started to accumulate snow and ice even though my defrost was in the max setting. My coat became soaked as the snow was heavy, wet and thick. As I didn't have my hat, my hair became freshly showered and my glasses were covered with snow.

When Christopher got in I pressed the Start Ride bar on the Uber App. and my heart sank as the destination address, Oxford Woods Dr. in Falmouth, was in an outlying area further inland that I knew would have much more snow.

The navigation app took us from Forest Ave., to Allen Ave. to Washington Ave., to Blackstrap Rd., where Oxford Woods Dr. would turn into.

When we turned onto Blackstrap it became more difficult due to very heavy snow coming down with poor visibility. Finally, we are within a mile of Oxford Woods Dr. which will be a right turn off of Blackstrap. Christopher had been rather quiet up to now, but at this point he asked:

"Do you have snow tires on this car?" "No" I replied. "This Camry does really well in snow."

Turning off of Blackstrap onto Oxford Woods Dr. became a challenge as not only was the road not plowed but there were no tire tracks to follow.

stuck in snow

After traveling a couple hundred feet Christopher said: "You better speed up as we're going up a hill." I tried accelerating but the traction control light came on and I could feel the car slowing down. Within a few seconds we were at a standstill. I tried backing up to get some momentum going forward but that was not going to happen on the incline we were on.

There was so much snow under the car that we couldn't move more than 3 or 4 inches. Also, the spinning tires had turned the compacted snow under the tires to ice so that the vehicle couldn't get any traction.

I tried rocking the car and Christopher tried pushing while I rocked. No dice. By this time I had been outside several times trying to move snow from around the wheels with my gloves and windshield brush I had.

I was wringing wet and my shoes were soaked. It is now about 20 minutes past midnight and I am stuck on this road out in the sticks. If only I had purchased a shovel and a bag of salt like Sharon had suggested.

Christopher said that his house was a few hundred yards up the road and he was going to walk the distance, get a shovel and some salt, and return to help get the car out.

With Christopher on his hike, I had nothing to do but think of how my failure to plan had gotten me into this mess. I had always prided myself in the excellent strategic planning that had produced positive outcomes at each of the hospitals I had managed, and yet here I was stuck in a storm, simply because of a lack of planning.

I also thought back to the wonderfully warm and sunny Agana Beach, where my condo had been in Guam. Right now, it was the middle of the afternoon there with a temperature of about 89, white sands and a bright sun glistening off of the gorgeous blue water. This was the first snow I'd seen since departing for Guam four years earlier and I was already sick of this cold white stuff, yearning for the warmth and beauty of the South Pacific.

Just as I had closed my eyes, imagining myself snorkeling in Tumon Bay, Christopher knocked on the door. He had returned with a bag of salt, which we spread under each of the tires.

One rocking motion, then two, then three. On the third try the car started to move. I increased the accelerator, Christopher pushed from behind, and the car picked up momentum, escaping the four ice filled holes and bed of packed snow that had kept the vehicle imprisoned.

By 2 a.m. I have arrived safely home and Sharon is fast asleep.

After the roads had been cleared later that day, I made a trip to Hannaford's supermarket and purchased a small shovel and bag of salt. On my way home, I couldn't help but remind myself that it always pays to plan.

Theodore Lewis is former CEO of the Guam Memorial Hospital. He is now based in Maine.

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