Why Overachievers Fail at Meditation (And How to Fix It)

From October 4th to 11th, Alexis Santos is bringing his refreshing, uncrafted meditation approach to the Mediterranean for an exclusive, 7-day retreat at Peli Kastri in Greece.

We live in a culture obsessed with optimization. We optimize our schedules, our diets, our sleep cycles, and our careers. Naturally, when many of us sit down on a meditation cushion for the first time, we try to optimize that, too.

We try to win at meditation.

We close our eyes, tensely put our focus onto the breath, and wage an aggressive internal war against our own thoughts. When our minds inevitably wander, we label ourselves as failures. The result? Meditation becomes just another stressful task on an already exhausting to-do list.

Alexis Santos, a featured teacher on the Ten Percent Happier app, and a graduate of the Spirit Rock/IMS four-year teacher training program with Jack Kornfield and mentors like Joseph Goldstein and Carol Wilson, calls this the trap of over-efforting.

“If you try too hard to make something happen in meditation,” Alexis notes, “it’s pretty much guaranteed not to happen.”

Unlearning the Struggle

The style of mindfulness Alexis teaches isn’t about escaping your life or forcing your brain into a state of artificial calm. Instead, these teachings are deeply rooted in awareness and wisdom – a lineage passed down by his core teacher, the renowned Burmese master Sayadaw U Tejaniya (author of When Awareness Becomes Natural).

Instead of treating the mind like a wild animal that needs to be disciplined, this understanding asks you to step back and simply notice what is already happening. This practice leads us to a relaxed continuity of awareness that becomes available in every aspect of our lives. If your mind is busy, you notice a busy mind. If your body is tense, you notice the tension.

By removing the judgment and the intense strain, something extraordinary happens: the mind relaxes on its own. The practice ceases to be a chore and becomes a refuge.

A Sanctuary for the Mind: This October in Southern Pelion

For a mind accustomed to constant stimulation, the physical environment matters deeply. Peli Kastri was designed specifically for this kind of deep, understated restoration. Nestled in a pristine, non-touristic bay in Southern Pelion and surrounded by ancient olive trees, the center balances boutique eco-luxury with authentic regional culture.

There are no rigid, military-style schedules here. Under Alexis’s guidance, you will practice moving seamlessly between formal sitting, slow walks on the beach, and quiet, plant-forward dinners sourced directly from local organic farms. You will learn how to carry awareness into your everyday life – not as a strict rule, but as a natural way of being.

If you have tried meditation before and felt it “wasn’t for you,” or if you are a seasoned practitioner looking to transition from effort to ease, this week is your turning point.

Registration is strictly capped at 40 participants to maintain an intimate group dynamic.

→ View Tiers & Reserve Your Spot

We are incredibly honored and excited to host Alexis here at Peli Kastri. For his dedicated students, listeners, and followers, this is a rare and beautiful opportunity to practice with him in person, immersed in the quiet magic of the Mediterranean.

Alexis Santos Meditation Teacher, featured on 10% happier app

Meet Alexis:

Alexis Santos
Alexis Santos stands out in the modern mindfulness landscape as a teacher who completely reimagines how we interact with our own minds. He cuts through the stiff, militaristic archetypes of meditation, offering an approach that is deeply intuitive, practical, and tailored for the complex modern intellect.

Alexis’s background bridges Western achievement with deep Eastern contemplative training:

 After graduating from Harvard University in 1995, Alexis spent several years in medical school. Sensing a need for a radically different path, he chose to leave his medical career behind to travel and look inward.

His search led him to India and eventually Burma (Myanmar), where he met his primary teacher, the renowned meditation master Sayadaw U Tejaniya. Alexis ordained as a Buddhist monk from 2003 to 2005, immersing himself in a lineage that prioritizes wisdom and the mind’s attitude over rigid physical postures.

After returning to lay life, he spent four years completing the rigorous teacher-training program at the Insight Meditation Society (IMS) and Spirit Rock, mentored by foundational Western Dhamma figures like Jack Kornfield and Joseph Goldstein. He has been teaching internationally since 2012.

The Method: Relax and Be Aware

Alexis’s teaching style is natural, uncrafted, and highly pragmatic. Having walked the path from Harvard graduate and medical student to an ordained Buddhist monk in the Theravada tradition, Alexis understands the modern, intellectual mind.

His approach cuts through esoteric dogma. It is an experiential exploration of open, wisdom-based mindfulness:

  • More about Alexis and his teachings: HERE

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