365 Consecutive Days of Headspace

Lessons from a year of meditation with

Steven Wakabayashi
7 min readDec 29, 2018
Finally, all the badges are filled!

Preface: This is not a paid advertisement by


I finally did it.

365 days of meditation in a row.

Though I wasn’t expecting anything more than just a badge with confetti, a year of mindfulness has radically changed my life.

But before I get into my lessons, some backstory of how I got into daily mindfulness.

At the end of 2017, I got extremely sick. Like, sick, sick. My digestive system shut down and I was in and out of hospitals for months trying to diagnose my health issues. Let’s just say that I could not keep food in. Both ways. Hundreds of hours and thousands of dollars later, every doctor visit and lab test came up empty with no solution in sight.

Hopeless and extremely dehydrated, I vowed to try something different to save my life.

I used to be the type of person that would take a prescription for everything.

Headache? Advil.
Stomach pains? Chew some Tums and wash it down with Pepto-Bismol.
Cough? Time to get that Z-Pak.

Image by Anton Fristler

I had been a firm believer that western medicine could heal everything. In my moment of need, it was failing me.

As a part of my vow, I sought out help from doctors specializing in eastern medicine and one of their prescriptions (along with some herbs) was to work on my mental health, starting with daily meditation.

I was in complete shock. How was daily meditation going to improve my digestive system?

But I was out of options. I had to give it a try.

Over the course of a year, I made it a priority to meditate every day if it was going to save my life.

I am so glad that I did.

Along with meditation, I dramatically adjusted my diet and lifestyle. Stomach issues have improved significantly and I am proud to say that I can digest food normally again (even better than before).

Healing is a combination of mental, physical and spiritual recovery. Just like daily visits to the gym improves physical health, daily meditation exercises mental health.

And with that, my lessons from a year of Headspace:

Change is gradual and cumulative

Before meditating every day, my meditation practice was on and off. I would do an hour-long session and put off the next session for a week. It wasn’t until I started meditating as a daily practice that I began noticing the impact.

Just like working out, it’s almost impossible to work out once a week and expect to get shredded abs. Every day is an opportunity to practice and reinforce lessons from the previous day.

After 2 months of consecutive practice, I started noticing a shift in my thinking. In difficult situations, I was able to take a “step back” and reflect in-the-moment. In my every day, I started to pause and appreciate random moments I would have otherwise missed.

Do: Meditate each day starting with a very short session. 1 minute. No more. Aim to build it as a daily habit first before trying longer sessions.

More focus leads to bigger rewards

I am a podcast-listening fiend. I listen to podcasts during my commute, as I am working out, while I’m cleaning my apartment and even as I shower!

I approached Headspace like a podcast during my morning commute to work. Rarely did I have a session where I could dedicate 100% of my focus from start to finish. A bit of my focus was reserved for checking the subway stop and shifting around to squeeze in more people.

After reading reviews, I created a meditation space in my room right next to my bed. Right after waking up, I would roll out of bed and onto my yoga block and fluffy rug where I would sit for 10 minutes. After a week, not only was I was absorbing more of the lessons, it was much easier to sit through each session without fidgeting. My body knew what to do in my meditation spot.

By being able to sit still for longer periods of time, I became more patient in all aspects of my life. I was more accommodating and kinder to everyone in my life.

Do: Create a dedicated meditation area for yourself. Get a comfortable cushion or yoga block and set it in an area of your room. Don’t move it! This will be your daily meditation spot.

Protip: If you are in a room with someone else, try using the bathroom for a quick meditation session. Put the toilet seat down and play the app in your newfound safe space.

Mental health is non-negotiable

Nights are chaotic and unpredictable. At work, I am often staying late to finish projects and if there is an outing with friends or colleagues, it’s easy losing track of time. Anything that I set up for the evening would often get pushed out to the next day.

I also found myself having anxiety throughout the day if I missed my morning meditation. I would have to find time in the evening to squeeze it in before midnight. By not being able to enjoy the day and worrying in the back of my mind, the best solution was to make it a non-negotiable item in the morning.

By creating non-negotiables, I was prioritizing myself. Just like how I was trying to multi-task and letting my schedule get taken over by others, I wasn’t strengthening my mental health without focusing on myself first.

Do: Meditate first thing after waking up. Head to your beautiful spot you have created for yourself and kick-start the day with a meditation session.

Meditation is self-compassion & unique to everyone

Prior to my daily practice, I tried every pro-tip and life hack to incorporate it into my lifestyle. I felt extremely discouraged after each failed attempt and would avoid meditating for days afterward.

I was reading self-help books about everyone else’s meditation habits (some for an hour or outdoors under the sun) and trying too hard to follow exactly what they did. It wasn’t until I created my own routine that I could begin to reinforcing my habit.

By forgiving myself for any missed days and adjusting, it became easier to come back and continue.

Some days, I meditate for 1–2 minutes.
Some days, I meditate in bed.
Some days, I meditate while stretching.

And all of this is OK.

Do: Be flexible with the meditation practice. Find your own pace of adopting meditation. Is it an app? Is it with a physical group? Think about what motivates you and where you learn the most.

Which one is right for me?

Out of all the apps, Headspace stuck with me.

It was a combination of:

  • Andy Petticombe’s (founder) soothing voice (not a mix of various voices like other apps)
  • Beginner packs are guided every single second (helps my monkey brain)
  • Beautiful UI and extremely easy to use
  • Packs are downloaded in advance and available for offline meditation

Started with the free trial beginner pack and paid for a discounted year upfront after. The additional sunk cost was a great motivator to use the app every day.

Protip: Google “Headspace Coupon” for available codes. You can apply coupons to their website at headspace.com/code.

If you do decide to try, here are some of my favorite


  • Beginner Series
  • Pro Series (longer sessions little by little)
  • Relationships
  • Creativity

Even with late night work (4 am Ubers, anyone?) and vacations abroad, I managed to meditate every day for a year. Though it was extremely difficult at times, my health was on the line.

Who knew that a prescription for daily meditation would change my life so dramatically in a year?

With patience, focus, and self-compassion — you can do it too.

Thank you for your time and readership!

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Have a fabulous day!

Metta (loving-kindness),



Steven Wakabayashi

Creative unicorn with an avid curiosity of life. Regular dose of mindfulness, social commentaries, and creativity: mindfulmoments.substack.com