Recapping the $100 Workweek



In November I embarked on the $100 Workweek experiment where I challenged myself to go the entire month spending just $100 each week, cash only. I am happy to report that I successfully completed the month, and I’ve never felt better having zero dollars in my wallet.

Here are the key takeaways from my experiment…

First, let me lay out the ground rules again in case you need a refresher:

  1. The week starts on Monday. On Monday morning I withdraw $100 from the ATM. My ATM PIN is…(just kidding)

  2. All transactions in the week must come from that $100 in cash. That means no online shopping, no putting it on my card and having someone else pay me back in cash, no quick swipe here or there, nothing.

  3. Basic living expenses do not count as part of the challenge. I still owe rent and monthly bills. I don’t think I can get away with telling the parties I owe, “but I’m doing a $100 challenge!” (Groceries are part of the challenge, though)

  4. Public transportation does not count as part of the challenge. Due to the Ventra Card conversion in Chicago’s CTA system, I have no choice but to use a card that’s linked to my bank account.

  5. Weeks may “rollover”. Meaning, if I spend $80 one week, I get $120 the next week. Since I would still have that same $20 cash on me, all I’m doing is just adding the next weekly bill to my wallet. This still allows me to plan that in one week I may need to cut back if I anticipate spending more the next week.

  6. On November 16th at 10 AM, tickets for Wrestlemania XXX in New Orleans go on sale. This is something I have had on my calendar for two months and I am not missing out just because of this challenge.This will be an online credit card purchase, and it will not count in my $100 for the week. Am I cheating? Well, that’s your call, but at the end of the day it’s my challenge.

To make sure I held myself accountable, I recorded every transaction. Here’s a copy of what I called my Living Lean Challenge Tracker:

Week 1

11/5--$7.14 Two groceries at Indian Grocer

11/7--$3.64 French vanilla latte and Buffalo Ranch McChicken at McDonald’s

11/8-$12.71 Lunch and cupcakes

11/8--$10.50 Two train tickets

11/9--$28 Grange Hall dinner

11/9--$28 Drinks at Map Room

11/10--$10 Drinks at John Legend concert


Week 2

11/15--$20 Drinks at Hub51

11/15--$17 Food at Boiler Room

11/16--$1 Donation on L

11/16--$8 Hot Doug’s

11/16--$20 Drinks at Lady Gregory’s

(An additional $34 was spent this week for $100 total but I must have forgotten to add it to the tracker)


Week 3

11/18--$6.63 Subway lunch

11/18--$44.67 Mariano’s Groceries

11/22-- (+)$5 from coworker for Starbucks

11/23--$1.63 Starbucks (remaining cost used on gift card)

11/23--$20 Food and drink at Boiler Room

11/24--$2.06 Ibuprofen at Jewel

11/24--$25 share of Clam Boil at Joel’s apartment


Week 4

(11/25--$36 Credit card UNICEF Typhoon Donation)

11/26--$9.98 Trader Joes lunches

11/27--$21.66 Dinner at Etno

11/27--$8 Beers at Kelly’s Pub

11/27--$2 Jukebox at Kelly's Pub

11/27--$6 Taxi

11/29--$57 Drinks and food at Jefferson Tap

  • A few things...First, don’t judge me for the McDonald’s purchase on 11/7. Second, in Week 2 there were $8 I couldn’t account for and have no idea where it went. So assume there was something else I spent money on with my $100 that week. Third, on 11/25 I technically broke the rules and made a credit card payment, outside of my $100 scope. This was a donation for relief in the Phillipines for the typhoon. I was okay with breaking the rules in the interest of helping others and doing the right thing.


  • You might notice that I didn’t actually purchase a full bag of groceries until Week 3. Well, unbeknownst to many, I suffered a very severe back injury at the end of October and for a few days I physically could not walk. Once I was in a position to walk, I couldn’t get more than 10 or 20 steps without pain, so going to the grocery store plus walking with bags in hand on the walk back was just something I physically could not do. As a result, I got by in the first couple weeks with food I already had from before the challenge, plus my mom brought me a bunch of home cooked meals. You might consider that cheating, but again I physically couldn’t get groceries, and on top of that, you try and say no to your mom’s cooking.


  • On 11/16 I made a donation to a guy panhandling for some cause on the L. Clearly it was a noble cause, as I have no recollection to what cause I donated.


  • On 11/22 I actually found a way to make $5 by getting Starbucks for my coworker and using a gift card I had saved to purchase it. Since I actually ended Week 3 with $5 extra, I had $105 to spend in the final week. Damn you Jefferson Tap Photo Hunt game...


  • Living Lean for the month forced me to be a shitty boyfriend at times, because I couldn’t pay for things. My girlfriend was a trooper in November. Still, I was able to cover costs for the both of us on 11/9, 11/15, 11/16, 11/23, and 11/27.


  • I also had to be a shitty friend on one night, leaving a birthday party at a bar early because I had no money left. Let me tell you, that takes discipline.


  • That final week, I planned to save $50-$60 for Friday night, 11/29. My good friend from high school was in town from New Orleans and I budgeted this would be a more expensive night. All of the money left in my pocket was spent at Jefferson Tap on food, booze, and Photo Hunt.


  • I noticed throughout the month that when you tell people you are undertaking the $100 challenge, they are more likely to buy you a drink.


  • I stayed subscribed to newsletters like JackThreads, Gilt, Groupon, and other deal offerors because I wanted to consciously say “no!” to these bargains that I usually scoop. Scooping multiple bargains ultimately makes it costly, so forcing myself to see deals and refuse them was tough. Black Friday really sucked, but it’s made me less impulsive in December so I suppose it worked.


  • I've never carried and paid in exact change so much in my life.


Overall, I did this challenge to become better in the art of self-discipline and I believe it worked. It made for a good story in social scenes, and I found myself making decisions based on what I could afford--what a novel concept! I actually think I may do this every November because the money I saved last month has given me some coin for gift shopping this month, without setting me back. Although I only had to purchase groceries one time because of the injury, I am confident I can do this again sans injury.

To reward myself for making it through the month, On December 2nd I purchased a pair of custom Converse shoes I designed in July but never pulled the trigger. It cost me about $65--or more than half of the money I was allowed to spend during any week in November.

Questions about the $100 Workweek? Drop a line at



Rajiv Nathan is the co-founder of Idea Lemon with a background in digital and mobile strategy. He is passionately curious, a people-meeter, and lives by the motto, "you miss 100% of the shots you don't take."