Challenges

21 Day Challenges, Challenges

The 21-Day Meditation Challenge: Can 5 Minutes a Day Calm a Mind That Won’t Shut Off?

/

Lately, my stress has been leaking into places it doesn’t belong. I’ve been waking up in the middle of the night with my mind racing and once I’m awake, that’s usually it. No scrolling. No phone. Just laying there thinking about work until the alarm goes off. During the day, I’ve noticed I’m more irritable than usual, snapping at small things that normally wouldn’t bother me. Everything feels rushed, like I’m constantly behind even when I’m not. Most of it is coming from work. Right now, I’m juggling a lot at once. My responsibilities at work have expanded quickly, there are several high-stakes initiatives moving in parallel, and I’m effectively operating across multiple roles. Add in a global team spread across time zones, and it’s been hard to ever fully shut my brain off. I don’t love admitting this, but it started to feel unsustainable. I know what chronic stress does over time: to health, relationships, and overall life satisfaction. So instead of trying to “power through” like I usually do, I decided to experiment with something different. I decided to try meditation and see if it could actually help. Understanding the Challenge For the next 21 days, I committed to meditating every single day. This wasn’t about becoming enlightened. It was about seeing if a small, consistent practice could quiet my noisy mind. Clarify Your Intent The “why” here was simple. I’ve heard for years that meditation helps manage stress. I also know that chronic stress leads to a long list of negative health outcomes and slowly chips away at how much you actually enjoy your life. If I could get my stress under control, even slightly, I figured I’d: That felt like a worthwhile, low-risk bet to make (if only I could find the odds on Kalshi). Set Your Personal Baseline I hadn’t meditated a single time over the last several years. That said, I wasn’t starting without some experience. Nearly 12 years ago, I participated in a 3-month yoga and meditation study. The study participants did yoga for 20 minutes and meditated for 10 minutes every day. I remember feeling happier, calmer, and even having vivid, lucid dreams. I always wondered how much of that was meditation and how much was having few real responsibilities (I was in university at the time). Well, it was time to find out. Here’s my 30-day averages before starting according to Whoop: Finalize Your Plan Consistency mattered more than perfection. Because most of my stress came from work, I intentionally scheduled my meditation during the workday, typically at the start of lunch (which for me is about six hours into my day), when Slack messages, calls, and general chaos are usually peaking. On weekends, I meditated shortly after waking up. If I needed to move the session around, I didn’t stress about it (smart, ay?). The only hard rule was don’t skip the day. I also made a point to pause after each session and briefly reflect on how I felt, both mentally and physically. Establish Accountability I shared the plan with my fiancée, and she decided to join me for many meditation sessions. Having someone else in it made it easier to stay consistent, especially on days when my motivation was low. There were even days where I came close to forgetting my meditation and her nudge made sure I didn’t miss a single session. How the 21 Days Actually Felt Meditation wasn’t consistently peaceful. Some days were calm and grounding. Other days were filled with distractions, background noise, interruptions, travel, alcohol, sickness, and classic “monkey mind.” Thoughts about work, business ideas, workouts, and random daydreams constantly tried to take over. A few patterns stood out: By the end of the challenge, one change was undeniable: I stopped waking up in the middle of the night from stress. What Happened to My Metrics? I tracked my Whoop data throughout the challenge to see if meditation would show up in the numbers. Here’s the honest answer: There was no clean, linear improvement across all metrics. HRV and recovery fluctuated heavily day to day, often driven more by: That said, a few things stood out: The biggest improvement didn’t show up neatly in a chart: I wasn’t waking up in the middle of the night stressed anymore. The takeaway: Meditation didn’t override bad inputs but it did seem to raise my floor, especially mentally. Final Reflections Meditation didn’t eliminate stress from my life. That was never realistic. What it did give me was space. Space between stress and reaction, between thought and spiral. That space made me more patient, more present, and better able to downshift when things felt overwhelming. Five to ten minutes a day turned out to be a small price to pay for better sleep, improved emotional control, and a calmer baseline. I’ll be continuing this practice and specifically retrying this challenge over a more representative timeframe (not the holidays). Want to Try This Yourself? Here’s the challenge: For the next 21 days, meditate every day.Start with 5 minutes. Use a guided app if needed. Don’t aim for “peace”, just commit to showing up. Your mind is already loud.This is how you teach it to breathe again.

Challenges, The Big Ones

My First Extended Fast. 3 Days, No Calories.

/

“Discomfort builds discipline. Discipline builds freedom.” I’ve been hearing a lot about fasting recently, and I decided it was time to give it a real shot. Up until now, I had only dabbled in intermittent fasting — I think my longest stretch was something like 20 hours. But a few weeks ago, I started reading about autophagy, and that changed everything for me. Autophagy literally translates to “self-eating,” which sounds a little terrifying, but it’s actually one of the most beneficial processes our bodies can trigger. It’s how your body cleans house. When cells get stressed (like during fasting), they start breaking down and recycling old or damaged parts — misfolded proteins, worn-out mitochondria, and other junk that builds up over time. Think of it as taking out the trash and then reusing the good parts to build something new. I’m not a doctor — and definitely not a scientist — but there’s enough consensus in the research to make me curious. Studies from places like Harvard and the Cleveland Clinic suggest that autophagy supports longevity, metabolic health, and disease prevention by helping cells work more efficiently and resist damage. In plain English: it keeps your body running younger, longer. That sounded like something worth testing firsthand. I also learned that autophagy kicks in when your body is under mild stress — fasting, high-intensity exercise, carbohydrate restriction, or deep sleep. It tends to start around 24 hours without food and can peak between 48 and 72 hours. So, with that in mind, I decided to take on my first full 72-hour fast to experience the full effect. Understanding the Challenge Simple idea: no calories for 72 hours.That means no food, sugar, or sweeteners. What’s allowed: water, electrolytes (without additives), black coffee, and herbal tea (but you have to watch the ingredients closely). “No food. No flavor. No shortcuts.” Clarify Your Intent My “why” for this challenge was twofold: My commitment: “For the next 3 days, I’m committing to a 72-hour fast to reset my body, build discipline, and activate autophagy for better energy and longevity.” Set Your Personal Baseline There’s not much of a “baseline” when you go from eating to not eating — but I wanted to make this measurable. So I pulled a few metrics from my Whoop before starting: To be fair, my averages were a little skewed by weddings, travel, and general inconsistency — but that’s life. This was about effort, not perfection. Finalize Your Plan My plan was simple: But the details matter. I learned that hydration is critical when fasting. Normally, I drink around 76 oz of water per day, but during the fast I aimed for 90+ oz. I used LMNT’s raw unflavored electrolyte packets — most flavored ones use stevia or other sweeteners that can interfere with autophagy. And even though I love coffee, I decided to limit it to just two cups per day to avoid dehydration. Establish Accountability My fiancée was out of town, so this one was all on me.No one checking in. No one keeping me honest. Just me versus the fridge.Perfect setup for self-accountability. Commit to the Plan Day 1 (Sunday) Day 1 felt pretty good overall. I ate well the night before, so I wasn’t too hungry in the morning. I went for a 4-mile run and walked my dog another 3 miles. When I got home, the hunger hit — hard. I distracted myself with chores and work, which helped. By evening, I missed the routine of dinner, so I made some herbal tea and called it a night. Day 2 (Monday) Woke up with a surprising amount of energy and slept well. I didn’t feel too hungry in the morning but missed my usual eggs and coffee routine. A few hours into work I got a mild headache, so I downed some water and had my first LMNT packet. Within 15 minutes, I felt completely fine again. I worked out that evening but stuck to lighter weights after feeling a bit dizzy during warm-up. My heart rate was unusually high, even for an easy session — clear sign my body was working harder than normal. Still, I finished the workout and capped the day with another long walk. Energy steady, focus sharp. Day 3 (Tuesday) Slept great again. Woke up with decent energy, though I could tell I was running on reserves. Took electrolytes and a cup of coffee mid-morning when focus started to slip. Worked out lightly over lunch — upper body and core — but fatigue hit fast. Weights felt heavier than they were. Wrapped up the evening feeling tired but proud. I decided not to break my fast that night since it was close to bedtime. I wanted to do it right. Day 4 (Wednesday – Breaking the Fast) Since I started around 8 PM on Saturday, I waited until Wednesday morning to eat. Most experts recommend easing back in, so I broke my fast with a protein shake (Orgain plant-based, mixed with water). It was delicious. No digestive issues, so a few hours later I had eggs for breakfast and was back to a normal diet by the end of the day. Total fast time: roughly 85 hours. Final Reflections Honestly, the 3-day fast was easier than I expected.Sure, there were moments of hunger, light fatigue, and a few foggy spells — but nothing unmanageable. Here’s what stood out: Most importantly, it reminded me how powerful discipline can be. You don’t realize how much time and mental space food occupies until you remove it. I can’t directly measure whether autophagy kicked in (no lab test for that yet), but if the research holds true — improved cell cleanup, better metabolic function, and longer-term health — that’s worth repeating. From what I’ve read, 3-day fasts should be spaced 2–3 months apart, so I plan to repeat this quarterly. I’ll also experiment with a 24-hour fast once a week or month to keep my body familiar with that mild stress response.

21 Day Challenges, Challenges

Mouth Tape: The Easiest Challenge That Actually Worked

/

I used to think improving my sleep required fancy tech, a new mattress, or giving up all evening indulgences. Turns out, all I needed was a piece of tape over my mouth. This 21-day challenge might be the simplest I’ve ever done and it paid off. The Challenge: 21 Days of Mouth Tape Here it is: Wear mouth tape every night before bed for 21 days. That’s it. No massive time investment. No grueling workouts. Just a small strip of tape across your lips. My friend Reid is a big mouth tape advocate and gave me and my fiancée some samples from Hostage Tape. The first night we tried it, something clicked. She didn’t snore, and I woke up feeling unusually refreshed. I was ready to extend the experiment and see if mouth tape could truly improve my recovery. ➔ Understand the Challenge This challenge is embarrassingly simple. Apply mouth tape before bed. Go to sleep. Repeat for 21 days. There are dozens of brands out there. I used KT Tape and cut it into strips myself to keep costs down. It worked just fine. However, if you’re willing to splurge for a little bit of extra money you can get a precut, or shaped, piece of tape from a brand like Hostage Tape. ➔ Clarify Your Intent Why? Because I’m always testing. I’ve seen the hype around mouth tape and I wanted to know if it actually made a difference in my own sleep and recovery. My commitment: “For the next 21 days, I am committing to wearing mouth tape each night to practice curiosity and see if it improves my sleep and physical recovery.” ➔ Set Your Personal Baseline Using my Whoop, I tracked the following metrics based on my 30-day averages before the challenge: This gave me a solid baseline to compare against. ➔ Finalize Your Plan I pre-cut strips of KT tape and left them on my nightstand. I also packed some in my travel kit to stay consistent while on the road. Commitment: Wear a strip of mouth tape nightly for 21 days; no excuses, no skipped nights unless unavoidable (e.g., red-eye flights). ➔ Schedule the Work No scheduling app needed here. Just build it into your bedtime routine. ➔ Establish Accountability My fiancée joined me in the challenge. Built-in accountability, shared weirdness. ➔ Commit to Your Plan You could send a message like this: “Hey [Friend], I’m doing a 21-day challenge where I wear mouth tape every night to see if it helps my sleep and recovery. Just a heads up in case I start preaching the gospel of closed-mouth breathing.” 📅 Daily Log Summary 🫠 Final Reflections This might be the lowest-effort, highest-upside challenge I’ve done. I noticed results immediately. Even with off-nights due to travel, alcohol, or poor eating, the overall trend was clear: mouth tape helps. I’ll definitely keep going with this one. Key takeaway: Small, easy habits can deliver surprising results. Don’t underestimate the power of a $0.03 piece of tape.

21 Day Challenges, Challenges

No Social Media: And I’m not Going Back

/

Hi, my name is Dean and I used to scroll like my life depended on it. Instagram, Facebook, Twitter, Snapchat. All of it. I’d pop open one app, then the next, then circle back like I was checking some invisible mail. And it added up. I was averaging 10 hours of social media a week, every week, without fail. For what? A few laughs, a bunch of dog videos, and a steady stream of other people’s highlight reels. I didn’t like how that felt. I didn’t like who it made me. So I deleted them. Cold turkey. And I started a 21-day no social media challenge. The 21-Day No Social Media Challenge For 21 days, I committed to deleting Instagram, Facebook, Twitter, and Snapchat from my phone. I didn’t set out to be some tech-hermit or productivity guru; I just wanted to reclaim my attention and see who I was without the noise. This challenge was about mental toughness, but more importantly, mental freedom. Understand the Challenge The rules were simple: no Instagram, no Facebook, no Twitter, no Snapchat. I didn’t count LinkedIn or Slack (because I needed them for work), but I probably should have cut Reddit too… that one snuck in through the backdoor. This wasn’t about perfection. It was about intentionality. And for the first time in a long time, my phone wasn’t the boss of me. Clarify Your Intent I wanted my brain back. I was sick of the comparison loop, the endless scrolling, the dopamine dips. I knew I wasn’t actually connecting with anyone through these apps; I was just numbing out. For the next 21 days, I am committing to removing social media from my phone to practice mental discipline and reclaim clarity, presence, and self-respect. Set Your Personal Baseline Here’s where I started: Finalize Your Plan I removed all the main offenders from my phone. Reddit? I left it… big mistake. That became the digital methadone of this detox. But even so, I tightened things up as the weeks went on. I gave myself grace but didn’t let myself off the hook. For the next 21 days, I will delete Instagram, Facebook, Twitter, and Snapchat from my phone. I will track my screen time weekly and reflect on how my mindset changes. My goal is to reduce social comparison, increase presence, and build digital boundaries that actually serve me. Schedule the Work This challenge wasn’t about adding tasks to a calendar. It was about removing distractions from it. I set a reminder every Sunday night to check my screen time and journal a few notes. Just enough structure to stay honest. Pro tip? Turn your phone grayscale. It makes everything look like a sad 1940s newspaper and totally kills the urge to scroll. Establish Accountability I didn’t make a big public announcement. No “I’m leaving social media for my mental health” farewell post. I just did it. But I tracked the data and checked in with myself weekly. If you’re doing this, tell one friend. Or shoot me a message; I’ll cheer you on and hold you to it. Commit to Your Plan Here’s a sample message you could send if you’re doing this too: Hey [Name], I’m doing a 21-day no social media challenge to reset my brain. I’ve deleted Instagram, Facebook, Twitter, and Snapchat from my phone. Can you check in on me once a week and make sure I’m still holding the line? I might need a meme or two to get through it 😂 Week-by-Week Recap Bonus Insights: The No-Social Effect on Sleep and Recovery I didn’t just scroll less; I slept better, moved more intentionally, and hit optimal recovery zones more consistently. 🖐️ Final Reflections I don’t miss it. The likes. The posts. The constant performance. I do miss the dog videos, but I’m okay letting them go too. I’m comparing myself to others less. I’m feeling more present. I’m spending time being rather than watching. I feel better and not in a “look at me being productive” way. In a quiet, content, grounded way. Next up? I’m thinking about going grayscale full-time, maybe deleting Reddit and LinkedIn too. This isn’t just a detox. It’s a reset. A new normal. Ready to Try? Delete your apps. Reclaim your attention. Feel better. The dog videos will be there when you get back. But you might not want to go back at all.

21 Day Challenges, Challenges

Stretching Challenge: Loosen Up or Fall Apart

/

Loosen Up or Fall Apart: My 21-Day Stretching Challenge You’re Not Supposed to Feel This Old at 30 A few months ago, I started waking up with a stiff neck. A long car ride would leave my lower back barking. My knees hurt on runs. And honestly? I felt old. Not wise-old or confident-old. Just creaky-old. The more I thought about it, the more I realized the culprit: mobility—or the lack of it. I train hard and stay active, but I wasn’t doing jack for recovery. So I launched into a 21-day challenge to fix that, one stretch at a time. The 21-Day Stretching Challenge What it is: Stretch for at least 10 minutes every day for 21 days. What it’s for: Build full-body mobility. Get looser, more athletic, and less breakable. The virtue: Discipline. The kind that shows up daily—before the world gets loud, before excuses creep in. Understand the Challenge This isn’t a yoga retreat or a month in Bali. It’s 10 minutes of stretching. Every. Single. Day. You can target certain areas (I learned the hard way my hamstrings are made of rebar), or go full-body. For me, it was about feeling younger, moving smoother, and hurting less. Clarify Your Intent My why? “For the next 21 days, I am committing to stretch for 10 minutes every morning to practice discipline, increase mobility, and feel better in my body.” Set Your Personal Baseline Progress needs a starting line. I chose three benchmark stretches: I took baseline photos on Day 1 right after leg day. Big mistake, they’re embarrassing and I won’t be sharing them. But hey, at least I’m being honest. Finalize Your Plan My plan was simple: Final Commitment: “I will stretch for 10 minutes every morning using guided routines from the Peloton app to improve my mobility, support recovery, and create a sustainable daily habit.” Schedule the Work No ambiguity here. Stretching became part of my morning routine: I even started associating my yoga mat with coffee. It had the same level of non-negotiable. Establish Accountability I told my girlfriend about the challenge, and while I didn’t ask her to check in daily, she occasionally asked if I got my stretching in. Just knowing she was aware of it added a subtle layer of accountability. I wasn’t doing it for her but the idea of slacking off and having to admit it? That was motivation enough. Commit to Your Plan Need a sample message to lock this in? Try this: “Hey [Friend/Girlfriend/Mom], I’m doing a 21-day challenge to stretch every day for 10 minutes to improve my mobility and avoid feeling like an old man at 30. Can you check in with me each night to make sure I did it?” Overview of the First Week Day 1: Post-leg day stretch = humbling. My pigeon pose looked like a wrestling injury. But I showed up. Day 2: Morning stretch done. Lower body focused. Felt sore but looser. Easy to slide into routine. Day 3: Hamstrings and hip flexors are toast. Eye-opening just how tight I’ve become. Still feels good to move. Day 4: Upper body stretch today. Shoulders thanked me. Recovery at 69% according to Whoop, better than expected. Day 5: Back focus. Skipped a workout the day before. Combined with stretching, recovery score soared to 94%. Day 6: Forward fold still a mess. Knees shoot up like jack-in-the-boxes. Tightness = opportunity. Day 7: Toe touches = torture. But consistency is building. Even with a low recovery score (40%), I stretched. Final Reflections By the end of week two, I felt like a new version of myself. My body recovered faster, soreness faded quicker, and I started lifting heavier in the gym. The back pain? Gone. And I wasn’t just tolerating my morning stretches anymore, I was actually looking forward to them. Stretching had become a kind of ritual, not a chore. Sure, I may not keep it up every single day going forward, but this challenge carved out a new habit I’m committed to. Mobility doesn’t just happen. You have to earn it. Quote to Carry: “Discipline is doing what needs to be done – even when you don’t feel like doing it.” You in? Next challenge starts soon.

21 Day Challenges, Challenges

Caffeine Reset: Tired, Exhausted and Deprived

/

The 21-Day Caffeine-Free Challenge: Breaking the Habit That Owned Me Hi, my name is Dean and I’m an addict. I need it. I depend on it. I don’t even know how I would function without it. I rely on caffeine to survive each and every day. Monday or Sunday, work or chill, it doesn’t matter. My days start with caffeine, and the moment I dip in energy, I go back for more. But a few months back, something shifted. I went to Oregon, where there are espresso stands on every corner. I indulged. Lattes, Americanos, black coffee in the afternoon. When I got home, the habit didn’t stop. I was clocking three or more servings a day: matcha at breakfast, drip coffee by 10am, espresso after lunch, and sometimes another one just to coast to dinner. I didn’t feel energized; just not tired. And that’s when I realized I was addicted to caffeine. So I decided to reset. Resetting my caffeine tolerance with 21 days of NO caffeine. Understand the Challenge This one’s simple to explain, but brutal to execute: eliminate all caffeine for 21 days. No coffee, no tea, no soda, no caffeine pills if that’s your kind of thing. Nothing that gives you that artificial jolt. Clarify Your Intent My goal? Reset my caffeine tolerance. I don’t want to rely on anything external to get through my day. I want to reclaim my energy, not rent it. I also saw this as a test of self-control. I love coffee. Whether it’s the smell, the taste, or just the ritual of grabbing a cup. But this was about proving that I could choose discomfort, every single day. Commitment: “For the next 21 days, I am committing to have zero caffeine to practice self-control and rebuild natural energy.” Set Your Personal Baseline I was averaging 3+ caffeine hits per day. My WHOOP data backed up my burnout: I expected sleep quality to jump. More REM. Better recovery. Sharper mornings. Let’s see if that held up. Finalize Your Plan No caffeine. Cold turkey. I boxed up my coffee beans, matcha powder, and tea bags and stashed them in a closet far from reach. I made the barrier annoying on purpose. Those few extra seconds of friction was all I needed to snap out of autopilot. If you’re doing this yourself, scale it to your level. But remember: The goal is not to make it easy. The goal is to make it count. Schedule the Work You can’t “accidentally” quit caffeine. I prepped like it was a work project: Establish Accountability No surprise, but my girlfriend was my accountability partner. Except this time she did the challenge with me. She had been experiencing migraines and she wanted to see fi this would help! Commit to Your Plan Need a template? Steal this: “Hey [Name], I’m starting a 21-day caffeine-free challenge to reset my energy and test my self-control. Can you check in with me once a day to make sure I’m sticking to it? It’ll be brutal, but I’m determined to do it.” Daily Log Highlights Final Reflections This challenge taught me a few surprising things: Instead, I’ll keep doing mini-resets: 2-3 days off caffeine here and there to keep my tolerance low and my dependence in check. Bottom line: I broke the habit that owned me. Now I own it. “You don’t rise to the level of your motivation. You fall to the level of your systems.” – James Clear

Challenges, The Big Ones

My First Ultra Marathon: From Regret to Redemption

/

My First Ultra Marathon: From Regret to Redemption On a sunny morning at Malibu Creek State Park, my girlfriend and I were lounging under a small tree with coffee and books, looking out at the Santa Monica Mountains. But this wasn’t just another relaxing day. It was race day for the Bulldog Ultra, a notoriously tough 50k trail race with nearly 6,000 feet of elevation gain. And I wasn’t running it. I was watching. Watching other runners take on a challenge I had once signed up for. A race I had trained for. A race I pulled out of. The truth? I let fear win. I had started training for the Bulldog Ultra, ramping from 4 to 10 miles, but life hit hard. I got COVID (for the 3rd time…), had numerous work trips, and time slipping away. With just one week to go, I removed myself from the waitlist. The moment I sent the email, I regretted it. Seeing those runners push through the course made something in me snap. I needed to redeem myself. That night, I signed up for another 50k – a race in the Santa Monica Mountains with SAMO Trail Runs. I had just over two months. No room for excuses. The Training My plan: two midweek runs, a long weekend trail run, and strength training twice a week. I cleaned up my diet, focused on recovery with stretching, foam rolling, hot tub sessions, and ate clean, mostly vegetarian meals from local farmers markets. But the road was rough. A brutal 16-mile run on the hottest day of the year nearly broke me. I finished, but barely. And the setbacks didn’t stop. I got food poisoning. I traveled. I missed my longest training run. But I kept moving. I made the commitment, and I was going to follow through. Race Week Race prep was chaotic – sickness, work travel, and stress. But Friday night before the race was perfect. I cooked a big pasta dinner, prepped my gear, and got in bed by 8pm. Race morning: 4:30am. I was nervous. Excited. Ready. I laced up my Hoka Speedgoats and toed the line with ~75 other runners at Will Rogers State Park. As we set off in the dark, headlamps lit the trail. The climb began immediately. I looked back and saw the glow of L.A. below and dozens of headlamps flickering behind me. The sun rose over the ridgelines. I was flying. At mile 14, I was in 8th place. The Suffering Then it hit. At mile 21, the pain in my knees flared. Each downhill step felt like a knife to the kneecap. My pace slowed. The sun climbed higher. My hydration pack ran dry. By mile 27, I was in survival mode. The last 7 miles were brutal. I shuffled. Stretched. Sweat. I was out of water and filled with pain. But I knew this was the moment I came for. The suffering was the point. At last, I crested the final descent. I pushed through the last mile and crossed the finish line to cheers from my girlfriend, her mom, and a friend. I had done it. Recovery & Reflection The pain set in fast, especially in my knees and joints. But mentally? I felt incredible. I took pride in the struggle, in the fact that I hadn’t quit when things got hard. The next day brought soreness in unexpected places (like my biceps from pumping my arms!) but also a quiet sense of accomplishment. What I Learned “I put another cookie in my cookie jar.” —David Goggins This race taught me that discomfort isn’t a problem. It’s the path. And I’ll be back for more. Gear List: This was my first ultra. But it won’t be my last.

Scroll to Top