Are you a successful professional wondering "Is this it?"

Friend, I’ve been there.

I’ve gotten the good grades. Worked at the prestigious firms. Became an entrepreneur.

I’ve followed The Traditional Playbook for Success.

Yet after each win, I kept coming back to a nagging question:

“Is this it?”

That traditional playbook of success doesn’t account for fulfillment, internal angst, creative inspiration and – most importantly – a deep sense of aliveness.

It doesn’t solve for a life well-lived.

Live each day like you won the lottery

I want your life to pass a simple test.

At the end of each day, I want you to ask yourself:

“If I won the lottery yesterday, would I have the same exact day today?”

You’re past the point where your happiness should be dictated by a boss, a paycheck or the fear of missing out.

Apply for our next group coaching cohort

We’re currently taking a limited number of applications for our next group coaching cohort.

Khe was an amazing thought partner to me as I was thinking about the transition from founding & running a company to what's next. He taught me skills and frameworks I still use today - and helped me be more thoughtful about what I choose to spend my time on. 100% recommend!

Neil Parikh
Co-Founder, Casper

Who's this for?

  • 15+ years in finance, law, consulting or tech
  • You want to go deep into childhood, relationships and personal insecurities
  • You’re at the precipice of a significant life transition
  • Financially, you could take 1-2 years off and it wouldn’t be stressful

What will we explore?

We’ll use a socratic framework for exploring life’s trickiest questions, including:

  • What is the pebble in my shoe?
  • Why do I fear being ordinary?
  • Who gets my best energy?
  • What is enough?
  • Am I playing the right game?
  • Why am I always so busy?
  • How do I start my spiritual journey?
  • What makes me come alive?
  • Who am I?


Week 1: The power of purposeful inquiry

“I don’t have any time to think,” is a recurring challenge. When you’re always in react mode, it becomes impossible to see the big picture – your why – more clearly. You’ll learn how to build a profound (yet pragmatic) reflection practice that can fit into a busy schedule, so that you can ensure consistent alignment with your personal values.


Week 2: Designing your ideal work-life synergy

Most of us still need to work. Heck, even if you’ve had an exit — you probably still want to do some kind of work. You’ll build a work-life roadmap (from the ground up) that aligns your personal values and lifestyle goals. We’ll run you through exercises for identifying personal benchmarks for success and satisfaction in both areas.

Week 3: Cultivating a deep sense of equanimity

While freedom can solve certain problems, it cannot address issues like low self-worth, inner criticism, resentment, the inevitability of death, and other deep-rooted concerns that require more than just “free time” to resolve.

We’ll introduce practical mindfulness techniques to manage and mitigate your inner critic, envy and societal pressures.


Week 4: Find your leverage with $10K Work

Do you keep tackling the “small” things and putting off the “big” things, but you don’t know how to break the cycle? We’ll help you shift the focus from productivity towards impact, aligning tasks with your personal mission — so that daily actions feed into your larger goal of professional fulfillment and societal contribution.

Week 5: The Art of Meaningful Connections

Transform networking from a chore into an art form. This session is about crafting genuine relationships that outlast transactions, fostering a supportive network that thrives on reciprocity and shared growth.


Week 6: Defining Your Enough

Break free from the cycle of never-enough. This exploration goes beyond financial freedom, venturing into a perspective-shifting lens of “enough”. Define what true wealth means to you by examining Die With Zero, The “Magic Number” and the diminishing utility of money.


Week 7: What’s my legacy?

Contemplate the weight of your footprint. Here, legacy is not just about wealth but the resonance of your actions. We’ll contemplate existential significance and the diverse avenues to engrave a lasting mark on the world.


Week 8: Igniting Passion for Life

Reignite your essential spark for life. Money’s reach has limits; it can’t buy the sheer joy of being. We’ll dive into discovering and nurturing what makes you feel vibrantly alive, ensuring that your wealth is indeed well-spent.


Taking this program resulted in a shift in my perspective. It led me to transition from a narrow focus on details to a broader outlook on my life goals. As a budding executive and a new older mom, I knew that I needed to "level up" to keep performing at a high level.   In the past, I used sheer force to complete tasks, but I came to realize that this approach was unsustainable.  I now begin each day by prioritizing my North Star goals. (If you're curious about what that entails, you might consider taking this course!) This course carved out the time and gave me tools for strategic thinking, not just for my start up but for my family.   I better understand that I need to first define productivity in both my personal and professional life before delving into tasks.

I will admit that making time to engage in philosophical discussions with Khe felt like a burden, with a toddler to care for, but I know that in the long run I will think back to the learnings and make better decisions. For example, prioritizing my mental and physical health is crucial to becoming the best version of myself. While this may be common knowledge, it took Khe to motivate me to take action. As with anything worthwhile, what you gain from this course is directly proportional to the effort you invest in it. If you're serious about delving deep, this course is for you.

Monique So
Finance Director

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