Every few months, The Daily Stoic (of the book and journal of the same name) runs a challenge to help readers adopt a more Stoic mindset. These challenges focus on practices like gratitude and voluntary discomfort. The latest of these challenges, The Daily Stoic Freedom Challenge, is explained as follows:
The Daily Stoic Freedom Challenge is a set of twenty-one all-new actionable challenges — presented at a pace of one per day — built around the best, most timeless wisdom in Stoic philosophy. Three weeks of challenges designed to strip you of the chains of obligation to things that are inessential, and to help you bring a sense of tranquility and purpose to your life.
Each day you will be presented with a challenge that will help you:
✓ Simplify your life
✓ Free yourself from unnecessary baggage
✓ Complain less
✓ Practice gratitude
✓ Push your physical and mental limits
✓ Abandon harmful habits
✓ Make the most of your days
I’ve been skeptical about these challenges in the past because they require payment to join and access the material. But this time, I’m curious to see if it’s worth the cost. Since The Daily Stoic already offers a lot of free content (like a daily email), it seems fair that they charge for more in-depth programs.
For $49, participants accepting the challenge receive:
✓ 21 Custom Challenges Delivered Daily (Over 25,000 words of all new original content)
✓ 21 Custom Video Messages From Bestselling Author Ryan Holiday
✓ Printable 21-Day Calendar With custom daily illustrations to track progress
✓ Group Slack Channel For Accountability and Community
✓ Day 21 Wrap-Up Live Webinar With Bestselling Author Ryan Holiday
Beyond the challenge itself, I’m also interested in seeing how others are doing through the group Slack channel. I hope a sense of community forms that lasts beyond the 21 days. With that in mind, I plan to document each day from my perspective—and hopefully share insights from other participants too.
I’ll keep updating this page with links to each day’s experience. Hopefully, it gives a good sense of how useful the challenge is!
Challenges
- Monday – Day 1 – Take a cold shower or plunge
- Tuesday – Day 2 – Pick a diet to follow for the rest of the challenge
- Wednesday – Day 3 – Develop a daily outfit
- Thursday – Day 4 – Go a day without complaining
- Friday – Day 5 – Go on a staycation
- Saturday – Day 6 – Go a day without your smartphone
- Sunday – Day 7 – Write 3 thank you letters
- Monday – Day 8 – Do your max amount of pushups, situps or pull ups. Then wait for 1 minute. How many more can you do?
- Tuesday – Day 9 – Pick a work of fiction to read
- Wednesday – Day 10 – Reach out to someone you admire
- Thursday – Day 11 – Pick one habit to quit
- Friday – Day 12 – Plan (and live) the last day of your life
- Saturday – Day 13 – #Trashbag – Pick up one bag of trash
- Sunday – Day 14 – Visit somewhere beautiful. Take it in for 30 minutes.
- Monday – Day 15 – Do it now: solve one nagging problem
- Tuesday – Day 16 – Read an old newspaper
- Wednesday – Day 17 – Buy or make a nice gift for someone else. Send it anonymously
- Thursday – Day 18 – Laugh it out
- Friday – Day 19 – Pick one Stoic passage to memorize
- Saturday – Day 20 – Create a pebble jar
- Sunday – Day 21 – Pretend you’re watching your own funeral: what do you see?
