This past weekend I had the unique experience of re-living a slice of my work past from 20 years ago when many of my employees from the 90s gathered to reprise what was once an annual tradition — the Optimum Canoe Trip. 

Every year we used to trek out to Eastern Long Island for a 5–6 hour canoe trip down the Peconic River, followed by a swim and BBQ at my parents’ house. I had grown up canoeing that river, and at some point early on in my business thought it would be a fun and impactful way to build bonds among staff and later, between old staff and new staff. Anyone who had ever worked for Optimum Design & Consulting became referred to as an “Optimite,” so the trip was open to all Optimites, both past and present.

Best. Canoe. Trip. Ever.

It’s a great day. The river is divided into sections, each one different, starting with the tough-to-steer bit at the start as the canoes must be deftly piloted along a winding narrow section of the river bordered by low-hanging branches. Then comes the slog through the lilypad-ridden cranberry bog, the wide-open lake where we tie the canoes together and drift along as we eat lunch, and the swimming hole with rope swing near the man-made waterfall. After that is the ice cream break at the riverside Zagat-rated homemade ice cream stand, the culvert from the higher level of river on one side of the road to the lower level on the other, and finally, the peaceful and picturesque home stretch.

It’s a seven-mile trip, with just enough variety to keep the journey interesting and exciting. And at the end, tired and happy, we would decamp to a heated pool to relax our sore muscles and pig out on fresh-picked farm corn and fresh-caught grilled fish. What could be better?

The canoe trip ran almost every year between the mid-90s and mid-2000s, finally coming to an end when the canoe rental place stopped offering the trips for a while. Our largest groups came to about 30 people once significant others were included, which made for 10-15 canoes and a lot of funny stories about ambushing each other, racing each other, and of course, tipping over.

Life Gets In The Way

Optimum crashed hard after 9/11, losing a massive amount of business that led to laying off most of our staff. We were smaller and leaner, and comprised primarily of staff who had been together for many years. The idea of company social outings as a tool to forge bonds, increase goodwill, and provide fun experiences now seemed less important. We held game nights for a while, tried for an Optimum ski trip in years where the weather cooperated, but nothing like the large-scale canoe trip.

I am extremely proud of how long my staff has been with me, weathering many storms. The average length of Optimum employment is 18 years — and that includes a newbie. We have the occasional staff lunch or day drinking in the office on a Friday afternoon, bring in seasonal candy for the holidays, and we always have a dinner or party around New Year’s. But somewhere along the way, ex-employees got married and started families, and I became immersed in the chaos of my own personal life in my 40s. The Optimite gatherings slowed, and then stopped.

Blast From The Past

And then one day this past spring my Office Manager from 25 years ago reached out. She had moved to San Diego about 20 years ago but was going to be visiting NYC with her daughters in August, and could I plan a reunion? Could we have another Optimum Canoe Trip? Well, the canoe rental place had changed hands a couple of years ago and re-opened, so it was theoretically possible. But would anyone want to come?

I threw the question out there. Within 24 hours, every single ex-employee from that time period had agreed on August 11 and seemed super excited to see each other again. The extent of their enthusiasm came as the greatest surprise; even though many wouldn’t return home until very late Sunday night, everyone instantly made time for an all-day event to see people they used to work with 20+ years ago. One lived far enough away that she’d have to leave home before 6am in order to arrive on time, and one was going to be arriving by cruise ship just a couple of hours before the train he’d have to take out to Long Island. That was how important this trip was to them.

Deja Vú

Seven Optimites attended, along with two spouses and six kids aged 3-18. The oldest kid had actually canoed with us back in 2006 when he was just 5 years old — a trip which at the time had been billed as the Last Optimum Canoe Trip Ever — and said it was just like he’d remembered. 

It was amazing to see everyone again, and we fell back into our easy teasing of each other just like we’d never been apart. As we sat in the cargo van waiting to be transported with canoes to the top of the river, we started recalling other such times that we’d crammed into similar shuttles on our various annual company retreats. The stories came rolling out — several commented as we were sitting there that in some ways it felt like we were still all working together.

As we navigated our day — including one canoe tipping over within 30 seconds of launching (a record) and one pair of Optimites forgetting all their navigational skillz from years past and ping-ponging from riverbank to riverbank until we had to swap who sat in which canoe — it became clear that despite the years and the life events that had changed us, everyone was still very much the same person that they had been 20 years ago. The same tendencies that we used to tease each other about were still on display, and the jokes were even funnier 20 years later.

The Ties That Bind

My Office Manager shared that she had been staying with her husband’s family over the past week while visiting NYC. Since she hadn’t been here in seven years and they were meeting her second child for only the very first time, they kept pressing her to ditch the Canoe Trip. They kept asking, “but do you really have to go? You’re only here for a few days. These are people you used to work with 20 years ago!” They couldn’t fathom how that could be more important than family. 

In light of everyone doing whatever it took to be there that day, it struck me just how powerful of a community we had created back in Optimum’s early days. Through all the years and despite any big wins or name-droppable clients Optimum had scored, that sense of community has always been the thing I’ve been most proud of. 

Being a start-up and unable to offer large salaries, I had always heavily invested in corporate culture instead. Most of us were in our 20s then, single and willing to deal with crazy clients or pull all-nighters when needed, whatever it took to keep the wheels on during the crazy start-up years. Conditions were less than optimal as we crammed 10+ people into 650 square feet in shifts, sharing the only six computers and three phone lines we could afford at the time. 

In our last summer before we moved into larger space (1998), we didn’t have enough electricity to run the AC and the microwave at the same time. The server blew a fuse at least daily, requiring a 20-minute boot-up time because the faster PCs were needed for client work. We propped the self-closing door to the hallway open with a chair for circulation, and the curious passerby — often twice our age — would peer in at the hubbub. We must have looked like a clown car to them then.

But getting through the early years created what turns out to have been a very strong bond. There are no secrets when you’re sharing long hours in 650 square feet. We became each other’s family, and it was very gratifying to feel that sense of family reunion on Sunday.