Postscript: How We All Won the Company Weight Loss Bet

Joseph Rupp
5 min readDec 12, 2020


Failure is often the starting point for real change

I left a cliffhanger at the end of the prior post about the Company Weight Loss Bet. Mark Two, you may remember, lost the bet. He really succumbed as he hit the first hint of wind resistance when it arrived in late October, the first month of the bet. The holidays were upon us. Halloween candy wafted in the air, Thanksgiving Feasts loomed, and Christmas and other festivities posed too great a collection of traditional temptations to resist.

Two months after Mark Two handed me his cash at the end of March 2002, I noticed a change in his appearance. Ordinarily, Mark featured a cherubic face, round body, balding head, and perpetual optimism. He cultivated a habit of tapping his toes during any conversation and leaving his left hand nearly permanently sheathed in his pants pocket when standing. He wore khakis and a polo shirt, his uniform, not unlike most of our associates, nearly every day.

Now, there appeared a noticeably increased bounce in his step.

I always looked forward to seeing Mark amble up during the workday. He arrived nearly always smiling, seemingly joyful with a talent for observation and mimicry. He could pantomime my verbal mannerisms in a way that both disarmed and scared me.

Suddenly, Mark’s face began to narrow, his neck thinned, and his clothes hung loosely on his frame.

At lunch, Mark One and I started to tease him. Looks like you are taking up the bet again, we said. You are not getting your money back; you had your chance! It’s too late.

He told us he became inspired by what we did and our process. As a result, he decided to do two things: go all-in on the Atkins diet and start running. The results accelerated. Over the next few months, with the Chicago Marathon, held in October, as his goal, Mark began to alter the shape of his body. Already energetic, his levels rose higher. His usual optimism, if possible, seemed to increase.

His work product, always good, seemed invigorated by an extra dose of confidence. Mark would tell us how much better he felt, how he slept better, exhibited more of the energy we witnessed, and when he looked at pictures could see an obvious difference in his appearance. He looked and felt younger. His wife, Krista, loved his new habits.

By the time October rolled around, Mark realized his objective and completed the Chicago Marathon. it served as the culmination of months of hard work, preparation, and transformation. I was very proud of him.

Change can be hard to create. Mark Two carried an endomorph body type. He encountered harder obstacles than others. Moreover, he liked to tell anyone who would listen that he “was Italian” and that “cutting out carbs, especially pasta, is like committing heresy.” He came from a large family and they celebrated occasions frequently. He faced regular temptation and had to anchor an objective that would help him get through the tough times.

What’s the lesson here. I think of three primary lessons.

Failure as a teacher. He learned from his first attempt that he could start the program; he was challenged by continuing. You may remember he got out of the gates fast in our bet, but like a runner in a long race who sprints out of the starting gate, he failed to pace himself and lost it. He had to figure out how to get past his first failure moment. He knew that he could do the work, the question was could he maintain his progress.

Failure will teach you not just about your exit points, but, that you can start and pursue a goal. As in running or any other exercise, you must build stamina and muscle strength over time. Hitting a wall does not mean permanent failure. Use the prior failures as a mental wall to get past the next time you attempt the change.

Follow a model. Mark watched two co-workers achieve what he set out to do. He learned from our efforts and knew if the ordinary folks could do it, so could he. How hard could it be if his work buddies accomplished it? More importantly, he plugged into two “programs.”

The first pertained to how to change his eating habits by following a specific program, in this case, the Atkins diet. I’m not promoting that program; I’m simply stating that it worked in his case to follow an established program. There’s an old aphorism that the best diet plan is the one you stick to. So, find something that works for you and create patterns you can keep.

He also followed a running program and used a lifelong goal, completing the Chicago Marathon, as his NorthStar objective. It worked.

Know what motivates you. Mark deployed a good old-fashioned sense of fear. While not exhibiting any signs of coronary heart disease, the condition threaded his family line. Mark used that fear to inspire his change. We all know that we are either moving away from a pain (the threat of developing the same condition as other family members) or moving toward pleasure (the improved health, appearance, lure of completing a lifelong goal.)

In this case, Mark used the combination of factors to motivate himself. He would admit, however, the fear of disease posed a strong incentive. The key to his success following the program involved leveraging the fear and fostering a strong and powerful goal — completing the marathon.

I think of this example often because it’s a real-life case study of how we often stumble the first time we attempt a goal, but can regain our footing and succeed again. We know that the vast majority (92%) of New Year’s Goal efforts fail. That moment of resistance does not have to be fatal — find tools and processes that can help you get back at it.

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Joseph Rupp

I focus on how to effectively imagine, create and sustain individual and team transformation.