What I Learnt from the 90DSS Challenge

On September 30th, I crossed the finish line of my 90DSS challenge—92 days, to be exact.

I didn’t drop a dress size. I completely hated one of my mandatory daily habits. And for 18 days, my sleep routine unraveled entirely.

If you are looking for a sanitized, picture-perfect wellness story, this isn’t it. This is the unvarnished truth of what actually happens when you track five foundational habits and a keystone goal for an entire quarter—and the behavioural shifts that occur when you stop relying on motivation and start looking at system design.

You can view the original framework and for the 90DSS Challenge: Mid-Year Sprint under Challenges.

The Challenge

The challenge ran from 1 July to 30 September to capture a clean quarterly block. The rules centered on five non-negotiable daily anchors (“the dailies”) alongside one primary project:

📡 Exercise: Physical activity six days a week with one day of active recovery.

📡 Inxercise (Mind): 20 minutes of daily non-fiction reading, extracting principles to apply directly to daily life.

📡 Nutrition & Hydration: Fueling with clean whole foods; zero alcohol, zero refined sugar, and minimal processed food, paired with consistent hydration.

📡 Sleep: 6 to 8 hours of restorative sleep each night.

📡 Daily Journaling: An evening review to document what worked, what failed, and identify behavioural patterns and triggers.

The Keystone Project: Channeling the compound energy generated by better sleep, movement, and nutrition into one significant personal or professional milestone that had been sitting on the back burner.

Here is the honest reality check of how the 90DSS challenge dailies actually played out.

1. Exercise

The Target: Two outdoor sessions for natural daylight, two strength training sessions to build muscle (vital for women as we age), and two workouts of my choice, backed by one day of active rest.

This was low-hanging fruit. Prioritizing movement had been an objective of mine since the start of the year, so I already had a solid rhythm of gym sessions and neighbourhood walks that kept me grounded. Aside from three off-weeks where life disrupted my six-day target, consistency came naturally.

Sundays became sacred days of true rest where I turned off step trackers and simply let my body recover. For my free-choice days, I gravitated toward boxing and Zumba. Dancing again as an adult unlocked something therapeutic in me. In my first class, I felt self-conscious; months later, knowing the choreography and moving my hips without overthinking felt like pure joy. On days when I overcame a hard obstacle, Zumba was my victory dance.

Strength training, however, was another story entirely.

Wanting to break past a stubborn 5–8 kg plateau and demystify the intimidating section of the gym filled with clanging metal and tank tops, I hired a personal trainer for two months. It was an eye-opener. I discovered muscles I didn’t know existed, and the soreness was on another level. I also discovered that I am fundamentally a cardio lover who likes to break a sweat—and, frankly, I hated lifting weights.

Did I quit? No. For the first time, I learned what it meant to show up repeatedly with zero motivation. I never struggled to lace up for a walk, box, or dance, but I had to drag myself to the weights. Persisting anyway built the muscle of doing hard things.

I didn’t step on a scale, and I didn’t track centimeters lost. In fact, I gained size in my back, arms, and glutes. My metric for the 90DSS challenge wasn’t aesthetic; it was learning what my body was capable of when I simply refused to negotiate with my own excuses.

Feeling stuck in low-energy patterns? Read our blueprint: 7 Foundational Habits to Get You Out of a Rut.

2. Nutrition & Hydration

This was another area where I had decent baseline momentum, but the sprint pushed my discipline further.

These 90 days marked the longest stretch I have ever gone without sweets, chocolate, or biscuits. That was a milestone for me, as sweet treats had historically been my default tool for emotional regulation. Outside of two virgin strawberry daiquiris across two social outings and hot chocolate on six cold winter nights, I had no refined sugar.

Alcohol was a non-issue since I only drink occasionally in social settings. With processed foods, I allowed myself some practical flexibility: I chose clean options when dining out, but accommodated cravings for salty chips or Doritos when they hit. Hydration remained high and consistent throughout.

3. Inxercise (Daily Reading & Application)

July went smoothly. Powered by early sprint excitement, I showed up every single day except one.

Then August and September arrived. The novelty evaporated, and because I had failed to design an environment that protected this habit, I struggled. I missed 15 days across those two months. The root cause was simple: whenever I woke up later than intended, my morning contracted, and my reading time was the first thing sacrificed.

On days with tight turnarounds, I scaled the habit down to 5–10 minutes just to keep the chain unbroken. Weekends offered the opposite: with open mornings, I gladly read well past the 20-minute mark. The habit survived, but it revealed that good intentions fall apart without environmental protection.

4. Daily Journaling

Like my reading habit, journaling started strong in month one before hitting friction. I missed 18 days across August and September, occasionally writing entries the following morning instead of before bed.

The breakdown was linked directly to evening routines: whenever I worked or stayed up late, winding down was compromised, and journaling was abandoned.

Yet the entries I did write proved invaluable. Going back through past reflections allowed me to observe my thinking patterns with distance. I saw the minor issues that had caused me anxiety, watched how quickly they dissipated, and realized how much energy I had wasted on things that resolved themselves. It built a grounded, stoic perspective: challenges were no longer emergencies; they were temporary events to navigate.

The practice also surfaced critical blind spots. In reviewing recurring frustrations, I noticed a clear pattern with a relative who had treated me with persistent, passive-aggressive disrespect. For a long time, I had excused it, believing my kindness would eventually encourage better behaviour. Seeing the documented reality on paper forced me to recognize that my passivity was simply enabling poor treatment. Journaling gave me the clarity to establish firm boundaries and remove myself from environments that compromised my peace.

5. Sleep

This was, without question, the most difficult daily anchor.

I have a history of sleep debt. In stressful seasons, late nights became my unstructured “me time” to decompress. I would mindlessly scroll social media in bed to distract myself from emotional overwhelm.

During the sprint, whenever emotional stress spiked, the old default returned: late-night scrolling, deferred bedtimes, and poor sleep.

Having a personal trainer helped create external accountability. A bad night of sleep immediately sabotaged my morning workouts, so I began redesigning my evenings. I booked early Saturday training sessions, which eliminated late Friday nights.

More importantly, I lowered the barrier to entry. Instead of demanding that I fall asleep by a fixed hour, I redefined the metric: be in my nightwear, showered, teeth brushed, with my nighttime tea brewed by a set time. Lowering the threshold worked. Once the routine was set in motion, sleep followed naturally.

Even with that improvement, I missed my target on 18 nights during the final two months. Every time sleep slipped, a predictable domino effect followed: waking up groggy, missing morning reading, dragging through workouts, experiencing higher sugar cravings, and making poorer decisions. Sleep isn’t just one of the five dailies; it is the master switch that controls all the others.

The Keystone Project: Reality Check

My ambitions for the keystone project were high, but my initial planning overlooked the friction of technical setup.

Because the project involved unfamiliar territory, I purchased the wrong equipment early on. Weeks slipped away troubleshooting gear, adjusting software, and dealing with technical hurdles until I finally brought in a professional in late September to resolve the setup properly.

On paper, my milestone output was essentially zero.

Historically, a false start like that would have made me feel like a failure and abandon the goal entirely. This time, I reframed it. The 90 days were not wasted; they provided the necessary friction to get the foundation right. I didn’t quit, and I walked away with practical grit and an operational setup that is finally ready to produce. The project was planted late, but the soil is ready.

1. Sleep is the primary domino. When sleep falls away, every other daily discipline degrades. Protect the night routine first.
2. Failure is data, not an identity. Shifting from “what is wrong with me?” to “what about my environment made this difficult?” turns mistakes into actionable system tweaks.
3. Motivation is a terrible operational strategy. Systems and environment beat willpower every time. Lower the friction between your intention and the action.
4. Tomorrow is an immediate reset. An off-track day does not dictate the rest of the week. Rebound quickly without drama.
5. Track behavioural shifts, not just vanity metrics. Measuring consistency rather than a number on a scale removes shame and helps you build routines tailored to your actual life.
6. Shrink the habit to protect the streak. When resistance is high, scale the task down. Five minutes of reading or getting into your pyjamas on time maintains momentum when an ideal routine isn’t possible.
7. Consistency builds genuine self-trust. Showing up when your mood resists creates quiet confidence that a single “perfect” day cannot match.
8. Anchor discipline to activities you genuinely enjoy. Incorporating Zumba and boxing kept exercise rewarding, while investing in proper shoes and a tracking watch reduced physical friction.
9. Eliminating rigid finish lines encourages long-term adoption. Without the pressure of a drastic end-date transformation, the habits felt sustainable enough to keep going.
10. Give yourself grace during technical setbacks. Stumbling through the setup of my keystone project taught me that a slow start is still forward motion, provided you stay in the arena.

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If the first 90 days taught me anything, it is that sustainable change comes down to deliberate design, not fleeting motivation. Having learned how to show up on the days I hated lifting weights, I am continuing the 90 DSS challenge for another 90 days—taking this sprint to 180 days through to December 31st.

For this next leg, the tracker evolves:

1. An explicit Keystone tracker: Rather than leaving my big project to chance, I have added a dedicated column to track my two weekly deliverables as this seedling project finally moves into active production.
2. Prioritizing sleep as the lead habit: Bedtime routines are no longer an afterthought at the end of the day; they are treated as the foundation for the following morning’s performance.

Stop paying the willpower tax. Reclaim your signal with deliberate design!
Maintain Course. 📡
— The Signal East Team