Personal Experience

My Vipassana Journey

Matthew Diakonov

Matthew Diakonov

Engineer, startup founder, Vipassana practitioner.
60 days of courses. 972+ days of daily practice.

How I Found Vipassana

I'm a tech person through and through: 20+ products built, 3 hackathons won, a startup exit. My life was fast-paced, constantly optimizing, always building the next thing. I hadn't taken a single vacation in eight years. Not a single day. I worked seven days a week, including weekends. Vipassana found me at a point where I realized I was good at building things outside of myself, but had no tools for understanding what was happening inside.

Someone recommended a 10-day course. I was skeptical; 10 days of silence sounded like either a cult or a waste of time. But I'd tried apps, books, and weekend workshops, and nothing had stuck. So I signed up.

The First Course: Day by Day

I'm not going to romanticize it. The first course was one of the hardest things I've ever done. Here's what each day was actually like:

Why I Kept Going Back

After my first course, I said to myself: “I cannot go back and live a normal life.” It was that clear. I started planning my year around how many courses I could attend. In my first twelve months, I went to four courses, despite having an intense full-time schedule. It was so mind-blowing how much time I could save and how efficient I could become after learning meditation that I solely dedicated 40 days plus two hours of daily practice to ramp up my skills and get established.

Six courses now, across three centers in California, for a total of 60 days. Each time is different. Some courses are peaceful. Some are deeply uncomfortable. Every one has taught me something I couldn't have learned any other way.

I've sat at Dhammamanda in Northern California (private rooms, tall trees, almost too luxurious), the CYO Bay Area Christmas course (bunk beds with 12 people, rain and snow, nearly 300 meditators, the biggest course in the Western hemisphere), and North Fork in Central California (one of the oldest centers in North America, with a pagoda and private meditation cells).

Now I go to a centre twice a year, and every time it's a massive mind reset. The depth of meditation at a centre is night and day compared to home practice; you just can't reach that same level on your own. I come back making important decisions about my personal life, business, partnerships, everything. That clarity is something I can't get any other way.

What keeps me returning is simple: it works. Not in a mystical way. In a very practical, observable way. I react less impulsively. I'm more present in conversations. I sleep better. When something difficult happens, I have a brief moment of space between the event and my reaction, and in that space, I can choose.

Daily Practice: The Real Work

The courses are powerful, but the daily practice is where the transformation actually happens. 972+ days of sitting, every day at 6 AM and 9 PM. I currently sit with one other buddy, which helps with accountability. Some days the full hour flies by. Some days every minute is a battle with distraction.

Honestly, the meditation itself is still quite challenging. My main struggle is distraction; the mind just wants to wander. But it's a very gradual path. You definitely see improvement over time if you're consistent. It's a very long journey to master, and I'm nowhere near mastery.

The biggest insight I've had is that the real practice happens off the cushion. I try to pay attention to how I behave in normal life and carry what I learn from sitting into everyday moments: how I respond in a difficult conversation, how I notice a spike of craving or aversion before acting on it. When I do that, the benefits in daily life show up early enough that they naturally motivate me to keep up the two hours daily.

The hardest part isn't the sitting. It's the consistency. There are mornings when the alarm goes off at 5 AM and every part of me wants to skip it. But like any practice (running, coding, writing), the compound effect over time is extraordinary.

What Changed

Reactivity decreased

I used to snap at people, stress over small setbacks, ruminate for hours over things I couldn't control. That still happens, but less frequently and with less intensity. The gap between stimulus and response has grown.

Focus improved

Sustained attention is a muscle that Vipassana trains directly. I can work on complex problems for longer stretches without reaching for distractions.

Sleep got better

Not perfectly, not every night. But the average quality of sleep improved noticeably. Fewer racing thoughts at bedtime.

Relationships deepened

When you're actually present with people instead of half-planning your next thing, relationships change. I listen better. I argue less.

Equanimity in uncertainty

Startups are chaotic. Things go wrong constantly. Vipassana didn't make the chaos go away, but it gave me a steadier internal platform to deal with it from.

What I'd Tell Someone Considering It

If you're thinking “I can't afford to take 10 days away from work,” I understand; I literally didn't take a single vacation in eight years. But after the course, I couldn't imagine going back to living without this practice. Vipassana is the single most important event in my life. It completely changed everything, making me from an extremely agitated, ego-centered person into someone much better and much more happy.

For me, the best move was to stop reading (after this page, obviously) and stop analyzing whether it was right for me. I just signed up. The intellectual understanding of Vipassana is worth nothing compared to the experiential understanding.

It was hard. I wanted to quit. Days 2 to 4 were genuinely rough. But staying the full 10 days and following the instructions left me with something valuable, not because anyone told me so, but because I experienced it myself.

That's the whole philosophy of Vipassana: don't take anyone's word for it. Practice and see for yourself.

Disclaimer: I'm not a teacher. I'm not here to give advice. This is just my personal story and analogy to help you find the practice. You need to come to the course.

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