My Approach
Your outer work helps you drive impact. Your inner work helps you create alignment. Cycling between the two unlocks an upward spiral of growth & change.
As the co-founder of Ten Percent Happier, a successful meditation & happiness company, I spent a decade growing my outer & inner skills. I had the incredible (and sometimes harrowing) experience of building a world-class company, and the unfair privilege of working with some of the best spiritual teachers in the world (from Joseph Goldstein & Sharon Salzberg to the Dalai Lama). I consider myself incredibly lucky, now, to coach other founders and leaders in their outer & inner work.
Your outer work drives impact. This includes your business strategies, vision, mission, goals, priorities, plans of action, accountability, ability to get things done, etc.
Your inner work creates alignment. This includes your self awareness, personal goals, values, motivations, resilience, capacity to create internal harmony, etc.
Addressing sticking points in both (and not focusing exclusively on one or the other) will help you become more integrated and authentic while moving towards your goals with more speed, energy & conviction.
But here’s the deal: you don’t want to do this kind of work with your shadows running the show.
By “your shadows” I mean the unrelenting voice of your inner critic, or the feelings of unworthiness, dissatisfaction, fear, loneliness, or control (to name a few). They can help you hit your goals… but at a cost.
Clarity and warmth are the not-so-secret ingredients I employ to help you navigate this terrain from a more grounded place, and are two ways my clients often describe me as a coach.
Clarity: I am clear, steady, deeply curious, and always synthesizing.
Warmth: my coaching style is warm, vulnerable, caring, and inviting.
In a coaching role, this combination of qualities allows me to challenge you from a clear, loving place — the kind that wants what’s best for you, even when it’s hard.
How It Works
I don’t subscribe to a “templatized” version of coaching with a pre-set curriculum or required exercises. My goal is to meet you where you are at.
I take the time to understand the most important aspects of your life and (more importantly) who you are becoming, then I collaborate with you to uncover the most promising paths forward.
Here’s a sketch of what 1-on-1 coaching looks like in practice:
We kick things off with a 90-minute “discovery session” where I ask a lot of questions. In addition to getting a snapshot of your life, I’m keen to understand your core needs and values. We explore what you would like to get out of coaching, and what you need to make it a powerful experience. We then hit on some of the core agreements so that you leave feeling excited about coaching and ready to fully step in.
The core container of the relationship is a 60-minute coaching session that happens at least twice per month. Our conversations center around whatever topic is “up” for you — something you’re grappling with that has you feeling stuck, energized, confused, joyful, angry, etc. I’ll ask questions to help us find our way towards understanding what is important to you, how it’s related to your goals, and ways you can take action. Sometimes it’ll feel like a strategy session, other times an Internal Family Systems (or IFS) parts session. I wrap up a session with takeaways, next steps, and accountability.
Some of our coaching sessions will be more structured. When we come across topics that I have expertise guiding — e.g. helping you dream into who you’re becoming, build a growth plan, clarify your values, explore different “parts” of your identity, refine your productivity system, etc. — I’ll proactively offer this more structured approach.
There will be times that we meet more frequently, and/or for longer sessions. My job is to help you transform your life, and we’ll occasionally “turn up the volume” on our coaching when we hit on rich veins of work. (This is included in my monthly coaching retainer and does not cost extra.)
I’m also available between sessions if you need more help. You can text or email any time. We can also book an additional “spot” coaching session if you find yourself in a time-sensitive situation where coaching could be useful.
This coaching format offers a steady heartbeat of support — so you make consistent progress towards your goals — while staying flexible and responsive to whatever is most alive for you.
Plans
I offer a variety of plans for founders & leaders at different stages of development. If you’re curious about the possibility of working together, please reach out.
Here are a few of the ways I work with clients:
Group Coaching
Two 90-minute group coaching calls per month with ~6 other like-minded leaders. Perfect for early-stage founders or leaders.
1-on-1 Coaching
Minimum of two 60-minute 1-on-1 calls per month, with additional support as-needed. Perfect for growth-stage founders or leaders.
Co-Founder Coaching
Same as 1-on-1 coaching plus a three-way call at least every other month. Perfect for co-founders or exec team colleagues.
Add-Ons
I also offer 360 reviews, Enneagram typing, maturity assessments, and custom growth plans. Perfect for leaders seeking accelerated growth.
For every option, I work on a monthly retainer rather than a per-session fee. This monthly retainer covers all of our coaching sessions, plus the time I’ll spend on prep, follow-ups and any between-session support you need.
Frequently Asked Questions
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An average executive coaching engagement lasts around nine months, but mileage varies. I prefer to keep it open-ended and check in every ~3 months or after key milestones so we can mutually decide how long to keep working together.
I focus on delivering a transformative coaching experience, and have confidence that it will turn into a long-term relationship when the coaching is working well for both of us.
As we progress, you may find that you have internalized my guidance, and that could be a sign that it's time for you to find your next coach.
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This depends on your goals, but my clients typically start to feel the impact of coaching within the first two months. I’ve had some clients who experience an “aha” moment in the first session or two.
In our initial 90 minute “discovery” coaching session, I work with you to get a clear sense for what success looks like for you and we use this to guide our coaching time together. My experience is that, after two months of working together, both of us have a good sense for whether or not we’re making strong progress towards your goals.
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I won’t ask you sign any contracts, or to make big upfront payments. I do ask for an initial 3 month time + energy commitment, though, because I find it’s helpful to set a time frame for us to work together without having to re-evaluate after each session. I focus on delivering a transformative coaching experience, and have confidence that it will turn into a long-term relationship when the coaching is working well for both of us.
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I sometimes text or email to follow up on something we’ve discussed, but you can lean on me like I’m an extension of your team. You can text or email me with questions that are either pressing or might benefit from more reflection, documents you want me to review (e.g. business goals, development plans, sensitive emails, etc.), or even for an intro or contact. If you're not sure, just ask.
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I work with highly self-motivated leaders who prioritize learning & growth. This includes:
Founders looking for a partner in their growth & development
Creators looking to 10x their audience
Product leaders interested in leveling up
VPs, directors, and senior managers who want to lead with more clarity
Entrepreneurs searching for their next calling
My ideal clients care deeply, are profoundly curious, want to lead by example, and are committed to the process. They’re intrinsically driven to live a true expression of themselves, and are willing to take on whatever challenges that stand in the way.
About
Learning & growth lights me up. It always has, always will. Having the opportunity to support others on their own journeys is a dream come true.
For the first 30 years of my life, I had an obsession with personal and professional growth, but it was primarily fueled by my need to be “worthy” or “enough.” (👋 Enneagram 3’s out there.)
Starting in 2013, I “accidentally” co-founded a meditation company with a close friend and a best-selling author. It was a happy accident and meditation ate my life in the best of ways. Since then, my learning and growth has entered a new chapter as I’ve worked to pass the torch from unworthiness to love — a more powerful and cleaner burning fuel.
I’m now committed to helping others do the same, with work (where we spend most of our time) as the backdrop for supporting people’s development.
In my career…
I am one of the co-founders of Ten Percent Happier, a successful meditation & happiness company. We’re a team of incredibly caring, highly self-aware, and sharp people who have the fortune of working with world renowned meditation teachers, some of whom helped bring meditation to the west (including Joseph Goldstein, Sharon Salzberg, and the Dalai Lama). Our mission is to help people see more clearly what leads to happiness (and what doesn’t).
I spent ~10 years at Ten Percent Happier as the VP Product, helping to build the team and our award-winning product from the ground up. During that time, I imperfectly-but-successfully managed a variety of departments including: product, design, engineering, content, and support. I was once given the compliment that I was like a mule, able to carry a heavy load and keep moving things forward. 🐴
Since shifting my focus towards executive coaching, I’ve stayed deeply involved at Ten Percent Happier to support learning & development at the company via (internal) exec coaching and company culture.
My care for people gives me my superpowers — I genuinely love the people I work with. The skills I developed to hire well, support people’s learning & development, and create a collaborative work environment that delivers results all trace back to that care.
At home…
I’m married to my high school sweetheart. We’re buds with deep foundations in trust, care, and (as our kids now say) a little bit of mischief. We’re each on our own developmental journey, but also share a fair amount of that together — as parents, partners in crime, and in our spiritual practices.
I’m a dad to three kiddos: 9, 7, and a newborn. They vacillate between delight and embarrassment at my range of storytelling accents, dad jokes, and general over-enthusiasm for the job.
We homeschool our kids with a small community of entrepreneurially-minded families, and we live in a mini-homestead outside of Boston. That probably tells you more about us than you care to know. 🔨🐓🌱🍄
I enjoy reading/listening/watching/sharing about my interests in meditation, adult/ego/identity development, consciousness & awareness, wisdom & compassion, conscious parenting, alternative education, and entrepreneurship.
As a coach…
I have completed several coach trainings, including two 6-month intensives — one with the fantastic team of leadership coaches at Upbuild, and the other an Internal Family Systems (IFS) coach training program with Guthrie Sayen. IFS is somewhere between a personal passion, spiritual calling, and a coaching pursuit; when it comes to the inner work, this is the most powerful tool I’ve encountered.
In addition to ongoing training in different disciplines, I am supported by my own executive coach, a therapist, and a meditation teacher.
I coach ~20 clients at any given time. This. Lights. Me. Up. My favorite part about coaching is the creative space that opens up when we find ourselves down an unmarked trail during a session — somewhere you haven’t been before, and are unsure of where it leads. My job then isn’t to take you somewhere I think is better (I don’t know either) but instead to join you for the walk, looking out for moments of clarity. We step off into the unknown together, and sometimes end up in a place that neither of us knew was possible. (This happens more often than you might think.)
Contact
If you want to connect, please fill out this form or email me at derek@derekhaswell.com
