Lessons come from unlikely places. 

I recently spent the weekend at my summer camp’s 50th reunion hanging out with close friends and reconnecting with people I hadn’t seen in over 15 years. We slept in cabins, ate in the dining hall, went water skiing, tie-dyed T-shirts… I got to be 16 again for 48 hours and it was truly magical. 

Amidst the reminiscing, there was a lot of reflecting. What was 16-year-old Jacqueline like (no one called me “Jax” back then), how has she changed, how has she stayed the same? Camp was an extremely formative experience for me – perhaps my most formative. It was a place where I felt completely free to be “me” and as a result, I discovered who I was, what was important to me, and what made me feel fulfilled and happy.  

Being surrounded by former campers and counselors – friends and mentors – I was reminded of some of the most important lessons I learned; principles that have stayed with me my whole life and now, as I am several years into running and growing my own company, two, in particular, seem particularly prescient.

“Finish what you start”

“Never stop at the bottom of the hill”

For context, at camp, I was a canoe tripping guide (in Canadian speak, we called it being a ‘Tripper’), which meant that I lead campers on extended, overnight canoe trips in the Canadian wilderness for up to two weeks at a time. The two principles above came from one of my favorite Trippers who took me out as a camper. He pushed me harder than anyone and made me realize that I could accomplish things I never thought possible. 

5’ 1.5”, 16-year old me was portaging a canoe (and not those light Kevlar ones that exist today, but a 90lb, water-logged, metal Grumman as well as a 60lb pack) along a 1 km portage. Normally, I’d stop for a break every 300 meters or so, but he pushed me to walk the entire 1 km without stopping. He wouldn’t let me put down the canoe. It took over an hour to complete, I was moving so slowly by the end. “Finish what you start,” he said.  

And I did. And I had never felt so exhausted and so proud. 

Me taking a hatchet to the portage sign just after completing it

So why do you “never stop at the bottom of a hill”? Because the hill isn’t going away… it’s better to persevere over the challenge and wait to take a (well-deserved) break once you get past the hardest part. 

Despite the fact that I currently sit in an office for ten hours a day and only find myself out in the wilderness on the rare vacation, these principles are exceptionally relevant to running (and working at) a startup, especially when the going gets tough (which sometimes feels like the rule rather than the exception). 

In reflecting on my experience this weekend, I emailed my friend and former Tripper a note expressing how much he influenced my time at camp and beyond, how I’ve carried his teachings with me into the real world. He wrote back that people often overlook how much they also learn from their campers: “How I manage my team now is from lessons learned from [camp]. Although I can’t push them to tears with a canoe on their backs, from those experiences I’ve learned that people have an extra gear – just need to find the right trigger to help them find it. Thank you for teaching me that.”

Figuring out how to motivate a team to achieve the impossible, how to help people grow and achieve new heights is a big part of being CEO of a company and one of the hardest parts of my job. His thoughts are particularly applicable at this time in my CEO journey as I am actively working through how to find the right triggers for each member of my team. I never would have realized it at the time, but my summers in the woods were some of the best training for my years in the office. 

Reflecting back on how I helped campers have the courage to carry their first canoe, how I created an experience that left them remembering the torrential downpour and wild winds as the best part of their canoe trip vs the worst, is helping me to think creatively about how to energize my team today. We all need to be reminded every once in a while that we’re tougher than we might feel. 

Where have you learned some of your most important, if not unexpected, lessons? What were they? Please share them with me – I’d love to hear your stories and thoughts.


Photos from Camp:

2005 – my friend Jamie and me with other camp friends on the canoe trip (second to left, my Tripper who motivated me to #finishwhatyoustart).
Jacqueline Loeb Scouted
2019 – Jamie and me en route to our camp reunion
2019 – bringing tie-dye back