Roll The Dice

Question of the Day

I start each class with a question. The Question of the Day. This could be construed as an ice-breaker exercise similar to those held in stuffy corporate settings. To some extent, the purpose is similar. To a greater extent, our setting and purpose is much different. I run a gym. People come to our gym to stay fit and healthy, but also blow off steam from the rest of their day. By being pushed through challenging workouts, our members can both find release from their day-to-day demands and find a bond with everyone in class who shares in the experience of persevering through the physical challenge. I ask the Question of the Day to shake people out of their early morning fog or early evening cloud. To answer the question, you must be present. There is also an ensuing discussion over the commonalities or differences among the various answers.

The Question of the Day can come from anywhere. I describe the Question of the Day to a new gym member with “It can be fitness related, but usually not.” Some of my longtime members will scoff. It’s rarely fitness related. I often spend the last few minutes before a class starts bouncing questions through my head. I’ve resolved to always come up with the questions on my own. 

I have a couple regular questions. At the beginning of a month, I ask: “What are you going to work on this month?” At the end of a month, I ask: “What went well in the last month?” I ask seasonal questions, such as: “When has the season unofficially turned? Not the calendar date of change, but informal signatures such as the first lemonade of summer or pumpkin spice latte of fall.” Some questions reveal quirks of character or interests, such as: “If a song played whenever you entered a room, what would it be?” or “If someone wrote a profile article about you, what publication would you want the article to be in?” Some questions are sheerly for fun: “If you were a professional wrestler, what would your stage name be?” or “What is your go-to karaoke song?” Many questions provide a small window into personal values: “Would you rather always be late or always have to wait for other people?” “Would you rather have people view you as dishonest or incompetent?” I try to not get too controversial or heavy, but some answers lead in that direction.

I recently asked a question that provided a great insight into the way people think about the world. The question included a rational mathematical decision, cognitive bias, and has strong implications for how a person chooses to live their life to the fullest. 

The Question

I sat before the computer screen looking at the roster of members for my 5:30 class. I was again racking my brain for a good Question of the Day. My mind started venturing in the direction of a cash reward for one of two risky endeavors. I was trying to think of two potential challenges that were achievable, but not with 100% certainty. Say, “You can win a $100,000 by performing a perfect parallel parking job or hitting a basketball shot from the free throw line. What do you choose?” That felt unsatisfactory; not everyone plays basketball and we live in a city where not everyone drives. I needed something more uniformly accessible. My mind somehow landed on the rolling of dice. Everyone can roll dice. What I settled on was “You have one roll of a die to win a cash prize. You win the money if you land on the number 3. You can either roll a 6-sided die for the chance to win $100,000 or roll a 64-sided die for the chance to win $1,000,000. What do you choose?”

A little explanation on why I chose those numbers. Both sums of money are large, but neither are enough to retire away on. That said, $1,000,000 is more of a life-changing sum and $100,000 would alter your financial comfort, but not be enough to do something drastic like pay for a house or college education. The 6-sided die was chosen because it’s the standard-issue die and I chose the 64-sided die to make the big win just more than 10 times as risky, since the payout is exactly 10 times as large. I figured if I raised the chances exactly proportional, people would all just play the game for the big money. Since I always play Question of the Day with the class, I knew my answer would be to take the shot with the 64-sided die and go for the big shot. I imagined we’d have some risk takers, but most people would play it safe. After the first round of the question, I would ask some follow ups to see how many people I could get to change their mind by either changing the amounts or changing the odds on the die.

I was a little surprised that in my first class of about 10 people, only 1 person said they would roll for the big prize. My surprise was compounded when I changed the circumstances to a 32-sided die for the $1,000,000. No one budged. I was astounded when I changed the prize of the 6-sided die to $10,000 and kept the 32-sided die at $1,000,000. Only a few people changed their mind. In my morning classes the next day, I didn’t even open with the 64-sided die, I went straight to 32 and no one would take the shot at the $1,000,000. Lowering the payout of the 6-sided die had a similarly small rate of conversion to the risky 32-sided die. 

Number Crunching

There are some relevant mathematical, economic, and psychological elements that provide insight into this question, the response, and my surprise. First off is the Theorem of Expected Value. First arrived at by French mathematicians in the 17th century, Expected Value states that the value of a future gain should be directly proportional to the chance of receiving the gain. In this question, as opposed to some future stock speculation, the chance or probability of the outcome is easily determined because it is fixed by the number of sides of each die, either 1/6, 1/64, or 1/32.

Our Expected Values breakdown is as follows:

1/6  x 100,000 = 16,666.67

1/64 x 1,000,000 = 15, 625

1/32 x 1,000,000 = 31,250 

1/6 x 10,000 = 1,666.67

What we see here is that as I originally construed the question (6-sided for $100,000 and 64-sided for $1,000,000), the expected value is higher with 6-sided die. What I thought, and this was my own reasoning, was that some people would take the risk for the more life-changing amount of $1,000,000. I was wrong. People were risk averse. I was so wrong that even when the EV was clearly higher with the 32-sided die for $1,000,000 (EV=$31,250), people still chose the “safer” route of the 6-sided die for $100,000 (EV=$16,666.67). It wasn’t until I lowered the 6-sided die to $10,000 (EV=$1,666.67) that I got some people to move, though most still chose the 6-sided die. That means that the majority of people I questioned would have chosen to roll the 6-sided dice with an EV for each roll of $1,666.67 instead of $31,250 with the 32-sided die.

There are a couple of influential factors to note. An individual’s personal financial situation is certainly relevant. An individual who never has had more than $10,000 in the bank will have a different relationship to $100,000 than an individual who already has $200,000 in savings. Similarly, an individual who could pay off immediate debt or get a jump on homeownership utilizing the $100,000 could view the higher chance of success as more important. The chance of success with the 6-sided die is 16.67% and the 32-side is 3.1%. You are certainly more likely to come away with something rather than nothing with the 6-sided die. The closer your personal financial situation is to nothing you may consider it “rational” to get something, though this still wouldn’t be rational in the classical economic sense of maximizing value. I should also note that a couple investment savvy individuals did the exact calculation for EV and made the choice immediately.

A treatment of this Question of the Day and the response cannot leave out Prospect Theory, a theory of behavioral economics and cognitive bias developed by psychologists Daniel Kahneman and Amos Tversky. Kahneman went on to win the Nobel Prize for his work on the theory. A complete expounding of the theory is beyond the scope of this essay, but the theory deals with the different cognitive biases individuals have in situations of gain and loss. One conclusion of the theory is that in a situation of potential gains, individuals become risk averse. Essentially, just what we saw with the response to the dice question. Even though the potential gains were greater and a rational mathematical analysis would tell you to roll the 32-sided die for the chance at $1,000,000, my limited group of responders overwhelmingly sought the smaller gains due to the lower risk of getting nothing. It’s also worth noting that Prospect Theory also states that in a situation of loss, individuals become risk seeking. So if I were to flip the question to the prospect of losing $100,000 or $1,000,000, I would theoretically get a bunch of risk seeking responders.

The Game of Life      

Oftentimes, I view a Question of the Day that has such a one-sided response as a bit of failure. Not in this case. This was one of my favorite questions and answers. I have often been asked by members of my gym, “Do you record our answers somewhere? Are you going to do anything with them?” This is the only time I’ve felt compelled to do so, and it’s not because of the implications of how people spend or save or invest their money. I’m actually not a person especially concerned with money. I think most people overestimate its value.

And there’s the rub, I am very interested in values. What do you really value? What is important to you? How do you value Joy or Fulfillment? We have a limited time in this life. Are you living your life in a way that maximizes those values?

I can give some concrete examples from my own life. I didn’t always run a gym. I used to be a university administrator. I made a decent salary, had a stable career with an upward trajectory, and worked in a generally respected field. One problem: I hated my day-to-day life. I went to an office full of cubicles and couldn’t wait to get out of it. I experienced no joy in what I did. I value the joy of life. I had a passion for fitness and helping people. Leaving that steady job to work in a different field seemed so risky. Would I make the same money? What would people think of me? I stayed in education administration for years. I chose the safe route. Eventually, though, I started to think about what I valued in life. Was it living a safe life or an enjoyable one? Did I want to dread the space I walked into each day or have reverence for it? I took a leap. I gave up a bunch in salary to start. I worked really odd hours. I had to hustle from one gym to the next. I made it work. When I was a child, gym class was my favorite time of day, I now teach gym class to adults every day. I hang with ex-athletes and talk sports. I teach people who have never been in the gym how to lift weights and see their self-confidence rise. In the fitness industry we have a mantra of making a class the “best hour of their day”. That means that everyday I play a role in the best part of someone’s day multiple times a day. I help facilitate physical development, social bonds, and the joy of play. When making the decision to leave my role in administration, I chose the higher expected value in a joyful life than the financially safe play. I took the risk to live out what was truly valuable to me.

Similarly, I write every day. I am editing the draft of a book. I have ideas for my next two books. I’m finishing up this essay right here. The most likely outcome is that not many people read this. The books I write may never even get published. The safe play would be for me to devote time to personal training and remote programming. I now make a more stable salary than in those initial days in fitness, but the safe thing to do would be to make more money using the skills I have. Why would I waste time writing? People don’t even read anymore. The answer is because I value living a life fully engaged in intellectual and creative pursuits. I value having my voice present in the discussion of ideas. I will take on the risk of writing that book that no one read because I place value in engaging in creative expression. I will take that shot. If I am able to be successful in that endeavor, that is a more radically life altering than getting the income from a few extra clients. I want to live my life to the fullest expression of my values.

Many times, in response to the dice question, people asked, “Can we get multiple rolls of the dice?” I held firm that you could only get one roll. You only get one shot at this life. If you value something, it’s worth taking the risk. To not do so would be irrational.   

Life’s Work Risk Analysis

If you have a steady job, keeping it is the safest thing you can do. Going after something you’re passionate about is risky. There are a number of aspects of your life put at risk: finance, emotion, and reputation to name a few. If you are going to leave behind the standard career path, these are the risks you assume. That is the dominant narrative anyway.

Before becoming a full-time fitness coach, I worked as a university administrator. I had a good job title at a respectable institution, a team of employees reporting to me, and a decent salary with a robust benefits package. I had been promoted a number of times and my boss had talked to me about taking the next step in the universe of higher education administration. I was safe. 

I wanted none of it. I remember consciously telling myself to respond diplomatically to the possibility of advancing further in the system. My inner voice was screaming “No!” While the next step up would clearly distinguish me as someone with a bright career, my insides recoiled at the notion of taking one more step down that path. That said, I didn’t know what to do. I had carved out a nice piece of territory for myself in the system and couldn’t rightly just give it up. That would be too risky. 

While I had looked at postings on HigherEdJobs.com, I knew that moving to another university system would not help me. My skills and qualifications would lead me to the same type of role in a different setting. Maybe a bump in pay or more prestigious institution, but the nature of my work and my daily life’s dynamics would not change.

For quite some time I had held onto the clandestine notion that I could change lives and become a fitness coach. Years prior, I had gotten certified to coach and did so on the weekends as a part-time passion project. It gave me a way to further cultivate my love of fitness and nourish my desire to connect with and help people. There were a number of full-time fitness coaches at the gym where I coached. While I could fantasize about joining their ranks, I didn’t know if I could make the same sort of living working in fitness. Additionally, I worried about whether my passion for fitness would endure if it became my full-time job, not just a hobby. Lastly, what if I couldn’t measure up to the standard of a full-time fitness coach? I knew enough to know that the job demanded a lot of personality in addition to skill and knowledge. What if I tried and failed? My reputation would be forever stained as someone on a successful track who gave it up to fail. Also, again, it’s worth repeating, what about the money?

None of those risks were present in my university job. I had financial security, personal validation as a successful professional, and respect of people around me. If I left my administrative job, I would either make a living coaching or fail fantastically have no way to support myself. There was a lot of risk in leaving. The risk analysis that kept me in my administrative job looked a little like this:

Stay in JobLeave and FailLeave and “Works”
FinanceLow Risk (Felt satisfied)High Risk (Worst case)Medium Risk (could I make enough money?)
EmotionMedium Risk (Felt unsatisfied)High Risk (Would be ashamed)Medium Risk (would I still feel the same about fitness?)
ReputationLow Risk (Felt respected)High Risk (Would be viewed as failure by both administrative and fitness professionals)Medium Risk (Would people respect me as a fitness coach in the same way as a university administrator?)

 However, I was miserable in the day to day of my administrative job. The prospect of progressing deeper into that world filled me with dread. That dread was a key component to the reappraisal of my situation’s risk analysis. What if I stay in higher education administration for the next thirty years and felt that dread every single day? What if I lived my whole life with contempt for what I had to do to make a living? Conversely, what if I could earn a living doing something I loved? What if I enjoyed the place where I went to work? What I was risking by staying was a lifetime of unfulfilling work. 

I also began to reexamine the prospect of what it would look like to fail at being a full-time coach. If that was the case, what would I do? Well, I would probably go back to some form of administrative work. I would apply for jobs and have years of experience advancing within a certain field. I would have to explain a gap in my resume, but I would be able to say that the reason I had the gap was because I took a shot at what I was passionate about. Would people really hold that against me? I certainly wouldn’t look down on anyone who took a shot at something special or different. 

Lastly, I looked at the financial risk with a bit more of a realistic lens. Working in higher education is not the most lucrative field. While I was content with my salary, I was in no way wealthy. Additionally, as I stated, at the gym where I coached part-time, there were a number of full-time coaches. While they didn’t seem wealthy, they were also clearly making a living and had been sustaining themselves in that profession for years.

My newly thought out risk analysis looked more like this:

Stay in JobLeave and FailLeave and Works
FinanceLow RiskMedium Risk (Would take a hit, but could resume career track)Low Risk (I knew fitness coaches making a living)
EmotionVery High Risk (A lifetime of dissatisfaction)Low Risk (Would be unfortunate to fail, but I would have an answer)Low Risk (Even if passion waned, it would be more enjoyable than a cubicle)
ReputationLow RiskLow Risk (Few people judge someone for taking a shot at something special)Low Risk (I would be a person serving others in a field I enjoyed) 

It became clear that despite what one may initially think, the riskiest prospect was staying in my current line of work. I would be risking an entire lifetime of fulfilling and enjoyable work. Though there was the possibility of failure of making it as a full-time fitness coach, I could still resume my conventional career. That’s the thing about the conventional path, it’s pretty widely available. If I were to leave and it worked out, I had the highest possible benefits: having a career I loved and a workplace I was happy to go to every day.

As it worked out, I left the  administrative job and started coaching. The life of a fitness professional has not been without challenges in the emotional, reputational, or financial realms, but I have not regretted that decision for one second. It baffles me that I was kept in a line of work I found unsatisfying so long out of fear of losing something. I had nothing to lose and everything to gain. There is a false sense of fear that you will be risking too much by pursuing a passion. However, if you are in a job you dislike, you are already in the worst case scenario. We spend too much of our time at work for it to not be something that we feel a calling for. An accurate risk assessment proves not that you should value stability over fulfillment, but that you should seek out meaning and settle for stability in a worst case scenario. We are taught that stability and safety are of the highest value, but this is inaccurate. Meaning, passion, and purpose are the highest ideals. Stability should only be sought in a worst case scenario.    

Desire to Train: Physicality and Life’s Work

The desire for a perfect compass that always points to true north is shared by many travelers, but often times the path we travel is instead led by contours of rock and soil that make passage not just possible, but enjoyable.


Strength and conditioning, as with seemingly all other aspects of modern life, has advanced technically and analytically with time. There are constant innovations in equipment for both completing exercises and measuring the output of athletes. Strength and conditioning coaches can look at their athlete’s heart rate monitors, test an individual’s maximum oxygen intake, and even measure the speed with which an athlete moves a weight in a given lift. More and more professionals are tracking sleep, dietary choices, and recovery to maximize results.  Individuals who study the science and practice of strength and conditioning are constantly looking for new ways to deliver, measure and assess the best programs for their athletes.

Despite these advances, many grey areas still exist in the world of strength and conditioning. The data is still far from exact. Therefore, many rely on experience in the practice. One such method is “Rate of Perceived Exertion (RPE).” In this method,  an athlete is given an exercise with a prescribed number of sets and repetitions; they are also given an RPE score on a scale of 1 to 10. For example, if an athlete is told to do a set of squats with an RPE of 8, the athlete should feel like at the end of their set they could have done a couple more repetitions. If the prescription was for a set of 5 repetitions with an RPE of 10, then the athlete should feel like there were no more possible repetitions left when completed. This method allows an athlete to autoregulate their day’s training based on how they feel that day. Some days an athlete feels well rested and is able to hit a heavy weight with an RPE of 6; on days where the athlete feels sluggish, they will use the same weight for an RPE of 8.

A related “soft” measure that strength and conditioning coaches may collect from an athlete is a “Desire to Train” score. At the beginning of each day, an athlete will simply log their desire to be in the weight room or at the track on a scale of 1to 5. This may be a subjective score that is prone to individual variation (some people just like training more than others), but it provides a valuable insight into how hard an athlete should push or lay off. A low desire to train may indicate the end of a long hard training cycle where a period of rest is needed. It may indicate that an athlete has not slept or eaten enough to fuel their training. It could mean that life outside of sport has been stressful and their energy has been spent on mental rather than physical exertion. These are all good things for a strength and conditioning coach to know. Collecting a Desire to Train score can tell a coach and athlete when it is time to back off, rest, or reformulate a training plan. 


While most of us do not have anything riding on our physical performance, I would like to highlight the importance of this lesson to our everyday lives. 

What is your Desire to Complete Life’s Work score when you get up each morning to take on a new day?

Just as physical training takes energy and effort, so does life’s work. There will be days when you feel like you’re ready to attack the world and take on all comers, do it. There may be days where just showing up and going through the motions is what you have in the tank, that’s fine too. But examine the data. What was present when you felt like taking on the world? What were the circumstances that led you to just go through the motions? It may be due to factors such as a good night’s sleep or something out of your control such as a death in the family, those are still factors worth noting. Advanced strength and conditioning programs undulate and vary. There are high days and low days. Life works in the same fashion.

The highs and lows of daily variation aside, there is another important lesson to glean from the Desire to Train metric: burnout and change in focus. If an athlete is consistently reporting a very low Desire to Train, a strength and conditioning coach needs to look at whether the individual has overtrained and a significant rest or deload period is required in order to restore the athlete’s central nervous system. Likewise in life, a consistent period of days where your desire to meet the demands of Life’s Work may mean that it is time for a vacation or a few days off. 

What is more, a consistent low Desire to Train may mean a larger question needs to be asked of an athlete: do you want to keep doing this? Athletic careers don’t last forever and when the spiritual fire is out, why continue on? This is a hard conversation to have. Many athletes identify themselves with their sport and their training. If they stop, who will they be? What will they do? Again, the parallels to Life’s Work are strong. If you wake up consistently not wanting to go to your job, should that be the place you spend the majority of your time? If the idea of continuing on in your current line of work seems daunting, do you want to keep doing this work? 

Not all paths are endless. Sometimes you reach a trail’s end. This requires asking some deep questions. What is it you truly want to do? Who are you really if you are not your job or career? What will wake you up with a desire to commence Life’s Work each day? Your previous data can be a guide. When was the last day you were fired up to do life’s work? What was present? When did you start just going through the motions? What was lost?  

Many athletes continue on in training because it is what they have done, but not always what they continue to want to do. Similarly, many people continue on their paths because it is the one they have been walking. Just as an athlete can take up something else with their physical activity, you can take up a new challenge for your Life’s Work. Either way, you should have a high “Desire to Train” score to do the work.

Living Your Passion with Jessa Lemoine

My guest this week is Jessa Lemoine. Jessa is an athlete, coach and teacher. Each of these identities has shaped her. After growing up as a competitive gymnast, Jessa’s world was turned upside down when she was forced to abruptly stop gymnastics due to injury. Jessa went on to compete in track and field at the University of Georgia and then transitioned to life as a competitive CrossFit athlete, competing in the CrossFit Games as an individual and as a member of a team. After leaving her competitive life behind, Jessa focused on coaching and helping others to better themselves. Now, Jessa is continuing her journey as a Physical Education teacher in the Boston Public Schools system. We talk about each of these transitions and living through passion. Available on iTunes and Stitcher. More show notes available at makingkairos.com. 

Listen here: http://makingkairos.libsyn.com/living-your-passion-with-jessa-lemoine

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The Longevity Diet by Valter Longo, Ph D