From Chasing Enlightenment to 22 Days: What Actually Works

Jan 18, 2026

When I first was introduced to meditation via Buddhism, there was so much that was new and exciting. The more I dug into the ancient texts, the more this concept of enlightenment became something I was being drawn to.

It was so compelling, and intriguing, and mysterious. You mean to tell me if I sit in stillness long enough, I’ll become enlightened!? Well sign me up.

I was diving into all the stories of these ancient sages and mystics who would sit for hours or days on end on the path to enlightenment. I mean Buddhism itself starts with the story of the Buddha who sat for countless days under the Bodhi tree until he finally achieved enlightenment.

Perhaps the pinnacle of intensity, dedication and commitment was the 6am physical practices all in the name of awakening and enlightenment.

In hindsight and if I’m being honest that was part of the allure. It’s no accident then that, a few years later, I would be drawn to an organization called EnlightenNext!

The difference now, 20 years later is that I have much more grace with myself and my WHY is now clearer. I want to be more present in my relationships and with those I care about in my life.

I will tell you that this was something I didn’t always get right in past relationships and friendships and ended up paying the price for that non-presence. But with age, as they say, comes wisdom.

I recently completed a 22-day meditation streak. I’ve committed to sitting for at least 20 minutes each morning and this time feels different because I finally have a system that works.

Most people experience meditation backwards because they don’t have their WHY clearly defined. And that clarity about WHY led me to discover the real killer of meditation practices: perfectionism.

The Perfectionism Trap That Kills Your Practice

People worry about the most random things when it comes to meditation.

“Do I need to be sitting cross-legged on a meditation cushion?”

“Is a candle required?”

“Do I need to completely ‘clear my mind’ before starting?”

The short answer to these is “No”.

The most important thing to do is sit and close your eyes. It seems so simple, but it’s effective. Remember we’re playing the long game here.

Since it’s January, think about all the people dusting off their sneakers and training to run their first 5K.

They get fired up and suddenly, this is the year they’re crossing the finish line at the New York City Marathon in October. We’ve all been there. What most people forget is that progress doesn’t start with a marathon. It starts with a walk. Then a jog. Then a run. Only after that does the marathon make sense.

I fell into this exact trap. I attended a 10-day silent retreat which gave me opportunities to practice really long sits, some several hours long. Towards the end of the retreat, I even managed an overnight meditation. To be honest I don’t know how long I was meditating and at some point I did lose track of time. It was wonderful to experience.

When I returned home, I thought my daily practice needed to match that intensity. That was an unrealistic expectation, and one that was hard to replicate in the ‘real world’.

My experience over the years has been one of stops and starts and, while I never stopped fully ‘showing up’, I would pick it up and drop it as the need arose.

What’s different now is that I've learned to work WITH resistance, not against it.

Resistance Is The Practice

In the process of meditation the thoughts that come up are one form of resistance. They fill your mind and make you think you’re not doing this right and the point of meditation is to clear the mind and my mind is not clear so I’m not doing it right and this is so dumb and why did I even try and the last thing I feel like doing is sitting here and I have so many things to take care of this morning why did I even feel like I had time to sit here.

Sound familiar? The reason you’ve given up is sometimes not even known to you. It’s this clear feeling that you want to do this thing (meditate). But something is keeping you from it. You may not even be able to put a finger on it, but it clearly feels like an immovable object. Steven Pressfield in his book The War of Art would call this ‘resistance.’

“The more important a call or action is to our soul’s evolution, the more Resistance we will feel toward pursuing it.”

Steven Pressfield, The War of Art

The racing thoughts aren't a sign you're failing. They're proof you're doing something important. The practice isn't achieving a clear mind - it's noticing the resistance and sitting anyway.

Once you’re able to put a name to the thing standing in between you and your next meditation, you’re able to lessen its power over you. It’s a lifelong process and there will be hurdles along the way to be sure. The key is having a system that works. This is one such system.

Your 2-Minute Non-Negotiable System

The goal with this exercise is to get started right away. I’ll include links at the bottom of the post for anything mentioned.

Principle 1: Protect the practice

This one is key and SO HARD to do. When you wake up in the morning, even though you’ve grabbed your phone to start the day, resist the urge to check your emails or look at your calendar or even worse, your socials. Trust me, there is nothing more dangerous than thinking your will power (when you’re starting) is strong enough to battle these incredibly persuasive algorithms. Do yourself a favor. Give this gift to yourself. You deserve it.

And first thing is key. No ‘making a cup of coffee’, etc. Your very first action is this gift to yourself. And doing it the same time each day is key.

Some other tips that help: if your mornings are particularly chaotic, whether work, family or kid-related, then make it a point to wake up 15-30 minutes earlier!

Principle 2: Remove friction before you start

Don’t overthink this, you don’t need fancy tools. I use the Insight Timer app. Use what works for you. And don’t feel the need to use all the bells and whistles. The key thing here is to add a widget to your home screen so it’s the first thing you see when you grab your phone in the morning.

To prepare I’d download the app so you’re familiar with it and set up predefined duration for meditation. Insight Time also allows you to set a halfway-mark chime which is helpful as you get into longer sits and the mind starts wandering and wondering (how much time is left, did I even start the timer, etc). It’s also helpful to put your phone in do-not-disturb mode as I’ve been interrupted in the past by an incoming call.

Principle 3: Set a laughably small threshold

Start very small. I know I said sitting for a minute is fine, but let’s start with 2 minutes. Yup, that’s it. Sure you can have a 5 or 10 minute goal, but have a low enough threshold that you know you can commit to. Feeling rushed this particular morning? Go to the bathroom, keep the lights closed and get your 2 minutes in.

The key thing here is to make this a non-negotiable. Your goal is 5 minutes, but your non-negotiable is 2 minutes, every morning.

Principle 4: Build the ritual

My process: I get up, grab my phone, head to the den, put on my noise cancelling headphones (not required but definitely helps), sit on my meditation cushion, open Insight Timer, hit start, close my eyes. Rinse and repeat.

This exact system got me to 22 straight days of at least 20 minutes. Not through willpower or discipline, but through designing a system that was so frictionless I had no excuse not to show up. And yes, while I’m now at 20 minutes, there were days leading up to the streak when all I could manage was 2 minutes.

Helpful Links

Conclusion

I hope this letter inspires you to either try meditating for the first time or revisit it if it’s something you’ve tried in the past and gave up on.

My goal here was not to overwhelm you but remind you that you can do this. The key is to get clear on your WHY.

Why would a meditation practice be helpful for you in your life at this present moment?

Can you commit to 2 minutes?

Is it worth it?

Only you can answer those questions.

Twenty years ago, I was chasing enlightenment. Today, I’m just showing up for 20 minutes every morning.

Turns out, that’s the real path.

With gratitude,

Harry

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