On Doing

Hi, I'm Casey — welcome to On Doing!

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On Doing is an evidence-based coaching practice that helps founders and creatives climb life's second mountain. People come to us to become a better leader, and explore questions around meaning, money, engagement, and impact in their work. You might be a fit if you are:

  • A founder of a scale-stage startup looking to grow into your changing role
  • A leader looking to deepen a sense of calling in your work, so that you can prevent burnout and better engage your team
  • A creative seeking to make a good living without losing touch with the joy of your craft
  • A second-time founder exploring next steps amidst high-optionality

We primarily work with individuals 1-on-1 in 12-week and year-long coaching engagements. We also host retreats a few times a year and are always working on a few experimental projects. Interested in working with us? Send us an inquiry 😁 Or, read on to learn more.

Testimonials

Here's what a few people have to say about our work together:

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"Casey is a master at cutting to the core of what matters and getting you to think differently about things that have been personal obstacles for a while... would definitely recommend working with Casey and any of the retreats he organizes."

~Mattan Griffel - Co-Founder at Ophelia (YC W20) and One Month (YC S13)

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"I joined one of Casey's founder retreats in 2019... I'd recommend Casey as a coach to anyone, especially founders worried about how to align their company to their values and trying to figure out their next steps."

~Leandra Tejedor - Co-Founder at Vidcode (YC S16)

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"Working with Casey was a fantastic opportunity for me to explore my entrepreneurial journey in a safe space. The cadence of listening, feeling, and expressing in a non-judgmental manner helped me to identify parts of me that often get ignored otherwise."

~Aseem Sood - Product at Uniswap, fmr. Co-Founder at Open Collective

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"I've been working with Casey for over a year now, and there has been a significant impact on my work. I'd recommend him to any founder who is looking to craft a more fulfilling role for themself in their business."

~Dan Shipper - Founder at Every.to

An Evidence-Based Approach

Our approach is based on Acceptance and Commitment Training (ACT), a nascent approach within behavioral psychology that focuses on how thoughts and feelings influence behavior.

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ACT has 600+ randomized controlled trials supporting its underlying theory and practical application. It has been utilized in clinical settings as an evidence-based therapy, and non-clinical settings, like performance coaching for Olympic athletes.

On a high level, the work we do involves helping our clients:

  • Clarify their values and what is important to them
  • Develop awareness around what gets in the way of moving toward their goals
  • Build skills to contact meaning and take committed action even when things get in the way

To understand this a little better, let's explore an example.

A Tale of Two Motivations

Let's say you work in a lab, and you want to get a mouse to navigate through a maze.

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There are two broad ways you could accomplish this goal. On the one hand, you could shock the mouse every time it moves backwards or stands still, teaching it that to avoid pain, it needs to move forward. On the other hand, you could place a piece of stinky cheese at the end of the maze, and sit back to watch as the mouse is naturally drawn toward the smell of food. In the course of building a business, a founder's motivations can fall into these same broad categories. They could be motivated primarily by the things that matter to them — like a desire to provide for one's family, offer a high-quality product, or create a meaningful work environment for one's team. Intentionally tapping into this motivation can give work meaning, and help both a leader and their team sustain during hard times. On the other hand, a founder could instead be motivated by the desire to avoid that which they find unpleasant. One's day-to-day actions could be driven primarily by things like fear of failure, obligation to others, or a desire to overcome a sense of unworthiness through accumulating more <money | status | power>. When we're motivated primarily by avoidance, we tend to lose touch with what is important to us in our work, and we instead focus on finding relief from whatever is uncomfortable. This can take the form of excessive caffeine or alcohol consumption, overwork, procrastination, burnout, or being an emotionally unintelligent manager.

In practice, most of us have both "to" and "away" motivations in our life and work, and the salience of each shifts depending on the situation.

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Our work with clients is about helping them notice what kind of motivation is driving their behavior, and helping them learn to move toward what they care about even in the presence of what is difficult or painful. Ultimately, we want our clients to be able to contact values in situations where previously avoidance was their only available response. Over time, a life that was once dominated by electric shocks can become filled with the stinky cheese of meaning 🧀

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"Work seems never-ending only because... it is a pilgrimage, a journey in which we progress not only through the world but through stages of understanding. Good work, done well for the right reasons and with an end in mind, has always been a sign... of an inner and outer maturity."

~David Whyte, in Crossing the Unknown Sea

About

Prior to getting into coaching, I was a founder and community-builder. In 2014, I founded Hacker Paradise, a community-based travel company, and bootstrapped it to over $500,000 in annual revenue over the course of 3 years. After exiting Hacker Paradise in 2017, I spent a year on sabbatical, auditing grad school courses and reading extensively around the psychology and anthropology of religion. Post-sabbatical, I spent a year at a boutique PE fund that acquires and operates B2B SaaS companies, getting a sense for what life is like on the "other other side of the table." In 2019, I was exposed to ACT through several publications on values, and saw huge potential in its application to the world of work. Since then, I've been working with several psychologists to adapt the principles and theory to deepening in one's vocation. Now, I split my time between coaching, writing, and working on early-stage community projects.

Oh, and I think you're awesome 😉

Work With Us

Interested in coaching?

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After learning a bit about you, we'll find a time for a free initial session to see whether working together might be a fit.