New “health challenge” could be addictive, in the best way possible

It’s a tale as old as time —

Girl feels fat, unhappy, unhealthy.

Girl wants to make a change but is skeptical cause she’s tried change before and it usually not only didn’t stick but made her feel worse.

Girl’s gym dangles $1000 as incentive.

Girl’s eyes widen and she signs up.

Girl scarily shares her weight at the start of the contest, the heaviest she’s ever been, in hopes that cheerleaders along the way will motivate her.

Girl works really hard and loses 35 pounds in 44 days.

Girl is devastated that she doesn’t win the $1000 (and gets annoyed by all the “But you did win!” remarks; watch this).

Girl is bitter and falls off the health wagon, gaining back 11 pounds.

Girl feels fat, unhappy, unhealthy.

Girl gets this message from a friend —

Girl is skeptical and starts to compose her “Thanks but no thanks” reply. It doesn’t sound like her jam. But after poking around the site and encouraging herself to be more open, she has a change of heart and says ok.

While on the site, Girl notices a six-month challenge that starts the same time and with a $125 bet, promises a lucrative pot if she can pull it off. She shrugs and says, “Why not?”, reminiscent of when she wanted to run her first 5K, heard about a marathon training program starting at the same time, and since running in any fashion, for any distance, terrified her, shrugged and signed up for her first marathon instead of the 5K.

Girl wants Best Friend to jump in the “be healthy” waters with her and tells him about DietBet. He’s not into it. She suggests a challenge just between the two of them. He says no. A few hours later, he reluctantly says yes.

Which brings us to Girl today, as Girl completes challenge three of three.

The Challenges

Love Yourself Healthier

  • Timeframe: 27 days
  • Bet: $35
  • Goal: lose 4% of body weight
  • Number of players: 1258
  • Winnings: percentage of the $44,030 pot, dependent on how many people reach the goal
  • Number of winners: 684
  • Saya took home: $48.28 – $35 bet = $13.28

6 Months to Slim

  • Timeframe: 6 months broken up into 1 month rounds
  • Bet: $125
  • Goal: lose 10% of body weight in 6 months
    • Round One: lose 3% in the first month
  • Number of players: 538
  • Winnings: overall, percentage of the $69,375 pot, dependent on how many people reach the 10% goal
    • Round One: percentage of the $6825 pot, dependent on how many people reach the 3% goal
  • Saya took home: $14.84 for Round One
    • Note: half of the pot is kept for the last round as incentive to make it till then and the remaining pot is split evenly between all the other rounds — so if I can survive till Round Six, I’ll be in the running to split a $36,375 pot. They say an average win for a six-month game is $325.

Best Friend v. Best Friend

  • Timeframe: 46 days
  • Bet: $500
  • Goal: lose the highest percentage of weight
  • Winnings: $500
  • Saya took home: $500

Total winnings over 46 days: lost 21 pounds and gained $528.12

How I Did It


Mix of stairclimber, yoga, treadmill walking, outside walking, and biking. I worked out 4-7 days a week, usually 60 minutes a day.

It’s been uplifting to see how I went from Level 3 to Level 8, from 20 minutes to 60 minutes on the stairclimber. There are those who’ll say, “Do high-intensity interval training, you only have to do it for 20 minutes!” I like being able to zone out and just be deep in my own head or watching HGTV, so I don’t mind 30, 45, 60 minutes of not having to think.

I also like the stairclimber because I don’t feel comfortable running, with my bits jiggling all over the place. Not to mention, it’s a calorie torcher (I know, I know — the machine calorie counters are notoriously wrong. But the stairclimber is wrong with a much higher number than all the other machines). Speaking of calorie counting, do you know of a good website/app for estimating calories burned? I haven’t been able to find one.

I used MapMyFitness, MapMyWalk, and MapMyRide for the first time. They sync with my gym app and my scale app, and made tracking my work and my progress easy and fun.

Another source of motivation was the rewards program at my gym. I am this close to a free month and Motivated by Money Saya is salivating! I get points every time I check in at the gym, log a workout, complete a goal, connect an app, and various other tasks. My birthday is coming up and that’s 50 points so free month will happen soon, woot! Of course that $500 giftcard looks good but 25000 points is too long to wait.

That said, I do get oodles of points if I refer a friend — anyone want to join any of the Chicago Athletic Club gyms?!? If you’re able to go off-hours (any time outside of M-Th 4-8pm), you get a great discount. If interested, let me know. We both win — you get/stay fit and I get points!


I did a lot of smoothies (I forego the yogurt this time and liked it just as much if not more so), oatmeal with fruit, omelets (tons of veggies), roasted broccoli, toast with I can’t believe it’s not butter, deli meat sandwiches, and cheese with dijon mustard.

For milk, I used unsweetened almond milk.

For snacks, chocolate almond milk, tea (I got lots of different flavors to mix it up), and popcorn.

For drinks, tons of water (50-90 oz a day), a tiny bit of diet pop, daily coffee and flavored seltzer water.

I fell off the wagon a few times, with McDonald’s, oreos, nutter butters, grocery store hot bars.

On most days, days when I was good, I logged all my meals via MapMyFitness so I knew my caloric intake.


Weighed myself almost every day, always in the morning right when I woke up.


What’s next?

I’ve got five more months of my six-monther. So of course I thought, “If I’m going to be working towards that challenge, why not be the efficiency-loving fiend I am and work on another challenge at the same time?!” and promptly joined another one-monther. I can see myself doing a one-month challenge each month congruently with the six-month challenge.

I also created my own DietBet, Life of Yes℠: No More Excuses, and I’d love for you to join me! Stats show that players with friends in the game lose 52% more weight.

You don’t have to do anything scary like share your weight (though you can if you want) or plunk down a huge bet (it’s only $35). Also, there’s a No Lose Guarantee — if you win, if you lose 4% of your body weight, you won’t lose money. Even if everyone in our game wins, Dietbet will forfeit their cut so winners never lose money.

You can also invite others to join — the more players we have, the bigger the pot. You can be as involved as you’d like, from sharing daily with the community to only logging on at the start and at the end to submit your weight.

The game starts October 25th and ends November 21st, which I hope will bring us into holiday season strong and with a motivated attitude to keep it up.



  • download the app (Android | ios) — it makes submitting and checking up on yourself easy peasy
  • that said, tool around on the desktop website as well — there’s a lot more information there than on the app
  • weigh-in every week (but don’t fall for the ‘official weigh-in’ junk where you have to pay to submit; just submit manually, for your own benefit)
  • invite friends to games using your referral link; I think you get points that you can use to make bets
  • read the FAQs
  • know that with the longer games, like the 6 month ones, you don’t see any of the payout until the end
  • if you find motivation by playing along/interacting with a celebrity, look through the games to see if there’s anyone who catches your eye
  • someone commented in one of my games that if you want a crack at the highest payouts to join games that end right after the holidays, around the 26th of November and December 
  • you can play in up to three games at a time
  • if you’re a smoker and want to quit, check out QuitBet


  • broken record, everyone talks about prep but it’s true — I’m so much more likely to make a veggie-filled omelet or a batch of roasted broccoli if everything is cut and ready to go
  • I also made it a point to clean the kitchen right before bed or right when I woke up, finding an inviting space much more enticing in which to cook — who wants to start meal prep scrubbing a pan, washing a cutting board or clearing the countertop?


  • seeing the number go up is devastating so if I had a bad day or two, I wouldn’t weigh myself for a day or two after, while I got myself back to health
  • just like I was skeptical with DietBet, I was skeptical with having a ‘fancy’ scale — oh my god, I loooove our new scale and totally think the splurge was worth it. From the ease to the info it measures to the app to the being able to connect it to other apps. I use IFTTT to send all my numbers (weight, BMI, etc) to a spreadsheet. WORTH IT!


I enjoyed DietBet so much more than I thought I would! It was devastating to put so much work into the $1000 Warrior Journey and be so successful and still lose. I like that with DietBet, it’s all on me on whether I win or lose. The amount of money depends on others but not the win or loss.

Even though my DietBet winnings were relatively paltry, if I make the 6 months, they have potential to be substantial. And if this keeps me on a healthkick and losing weight — I’m currently the lightest I’ve been in about two years — well, that’s just the bees knees.

I’ve always hated the idea of tracking — calories, fitness, weight — but technology these days make it so easy and fun. I have seen the light.

Turns out, I can be wrong. About myself. About things.

Also turns out, I can be right. I am motivated by money when it comes to health, and seemingly, only money. Living longer, warding off diseases and physical challenges, looking and feeling good — all wonderful aspects to health and none of them motivating for me. I’m happy that I realize and embrace this about myself. Now I know where to focus.

So wish me luck. I hope this isn’t it. Whenever challenges end, the fear is always there that you’ll slide backwards, like happened this summer when I gained those 11 pounds back. But I’ve got my 6 month’er, my 1 month’er, and my game to keep me going. I hope you’ll join me in the Life of Yes℠ DietBet , it’d be so fun to cheer one another on and (crossing fingers) take home some money! And guys — being able to fit in clothes I haven’t fit in in forever, oh my goodness. Best. Feeling. Ever. The Skinny Drawer has been cracked open again! Go fight win!

UPDATE: here’s a follow up post I did on accountability and ways you can get some, including my next DietBet.