Join Me For A

JayWalking Session

explore new perspectives during a 90-minute experiential strategy session

Personal Development

Business Coaching

Spiritual Growth

My name is

Jay Rooke

and I live in wine country in Sonoma, 45 minutes north of San Francisco. Join me for a JayWalking session and you’ll gain new perspectives and clarity on the roadblocks that are keeping you or your business stuck.

What are

JayWalking Sessions

good for?

  • Learning to trust your intuition and trust your path
  • Changing your relationships with your thoughts
  • Benefitting from an insightful and impartial sounding board
  • Launching a new business
  • Optimizing your current business
  • Big decisions
  • Getting unstuck
  • Improved self-understanding and fresh perspectives 
  • Growth in leadership competency and capacity

I'm intrigued. Tell me more...

You’re investing in a 90-minute transformative experience where we go for a walk (virtually or in-person), you get 100% of my attention and we tackle the issue that you need an additional set of eyes to solve.

JayWalking sessions are meant to provide short-term, new perspective relief to problems that you’re struggling to solve on your own.  They’re ideal for when you need a new perspective, a fresh set of eyes, or a little bit of help getting out of your own way.While I primarily work with clients on long-term retainers, I recognize that many members of my community either can’t afford or don’t desire an immersive transformational experience. The purpose of the JayWalking sessions is to share my love, insights, perspectives and healings with those that are stuck on a particular topic or issue for which they need a breakthrough so that they can get unstuck and continue their journeys. 


The 3 Stages of a JayWalking Session

Listen and Learn

Explore & Envison

Execute & Embrace

1. Listen & Learn

Our journey begins with you setting the stage for our conversation.  We’ll spend some time getting to know each other, and have a deep discussion to gain clarity on why this topic is important to you.  Our goals is identify a “well-framed problem” and set the tone for our call.

2. Explore & Envision

Once we’ve accurately identified the topic, the conversation shifts to brainstorming, or what I call “idea popcorn.”  During this phase we explore new possibilities and combinations, take note of themes, synthesize patterns.  Our goal is to craft 1-3 routes forward that feel resonant and are preferable to your current situation.

3. Execute & Embrace

Without this part of the process, we’re just having an insightful conversation.  Execute and Embrace is all about laying the groundwork to help you either embrace new perspectives or start taking action towards your new goal.  This is typically the shortest portion of the call.

/ˈjāˌwôk iŋg/

  • When a pedestrian crosses the street without regard to safety.
  • The strategy of disregarding convention and choosing a less-traveled path to arrive at your destination faster. 
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Schedule A JayWalk To .

I’ve made all the mistakes so you don’t have to.  That’s why my podcast and radio show is titled Know Pain, Know Gain.  Let’s be honest: a 90 minute strategy session can save you thousands of dollars of mistakes avoided.

Who is Jay?

I don’t fit neatly into any category—and trust me, that works in your favor.  I’m an idea guy.  A crazy creative father of twins that is woo-woo and spiritual, but still grounded in practical solutions–think East Coast pragmatic meets West Coast progressive.

I excel at quickly and accurately surmising the situation, seeing what others don’t, synthesizing patterns and making connections to craft solutions that get to the heart of your matter.

I’m a personal development and business coach.  I host the podcast and nationally syndicated radio show, Know Pain, Know GainEntrepreneurship Made Real. My clients are often “spiritually curious” business owners pursuing their entrepreneurial journeys in search of personal fulfillment.  They hire me to help them cultivate, integrate and HARMONIZE their business growth, personal development and spiritual evolution.

I started my career as a trial attorney for the City of New York.  I left the law to go to culinary school.  Years later, I’d risk it all (and lose it all) pursuing my passion to open a restaurant.  Along the way, I’ve worked for large multi-nationals like NBC Sports and Merck Pharmaceuticals, as well as scrappy startups in the earlier stages of growth.

My super human pet trick is knowing how to ask the right questions that yield us new perspectives and solutions to problems that clients were previously stuck on.

We find ourselves in the most data-driven, information accessible, fastest-changing era in the history of time.  Yet confusion, discontent and separation abound. You don’t need another course, book or advisor to teach you “stuff.”  We live in an age where one’s ability to learn adaptive thinking will determine his/her happiness in the new economy.

Think about itthe practice of law, the pursuit of coaching, the art of mindfulnesseverything I do is all about learning how to think differently.  You don’t need more data, and let’s be honest: NO ONE has the answers for you.  All I do is teach you how to access a higher form of thinking. Your God-given gifts take care of the rest from there.

If you could have .

you would have done so already.
Stop resisting reality. 
Allow yourself to be supported.


Most frequent questions and answers

Pretty straight-forward.  If we wrap up and you aren’t convinced you got your money’s worth, I’ll refund it on the spot.  I bat pretty close to 1000% for these types of  things. BUT, these aren’t for everyone, and I get that.  Simply put, if solving your problem isn’t worth $500, then this isn’t the right fit.  For some of you, you’ll measure this through the ROI of what it’s worth to get one new client, for others, it’s worth the investment to learn a new mindset.  What’s important is that you can see the potential of our time together.

Not at all!  You be you, and I’ll be me.  Find a location that has meaning for you; I’ll find somewhere in nature for me, and we’ll make it happen!

Nope, this is a working call.  All of it.  If I think I can support you with additional work, I’ll tell you, and we can book an exploratory call outside of our session.

Fair question.  While Sonoma’s weather is usually pretty mild, we have wind, rain and sometimes fire!  Under easy rain and wind, I’ll still walk, but if it hits a level where you can’t hear me, I’ve got a “Zen Den” office set up that we can still work in.

Because this isn’t an exploratory session to see if we’re the right fit to engage in a year-long retainer with each other.  This is a working session where I bring decades of experience and training to bear on your situation.  I’m more than confident I can deliver for you–that’s why I offer a money-back guarantee.

Nope.  Audio recording will be provided after the session.  If you want your session transcribed, I have a service that is reasonably priced.  

No worries.  Email me at!

Questions? Please call or email me.

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