Our Work Together

Private coaching for high performers creating what matters.

our work together

This is one-to-one work. It unfolds one conversation at a time.

You speak. I listen, And I ask the questions no one else in your life will ask.

Our work focuses on you, the human being behind the performance. Together we explore your mindset, beliefs, fears, patterns, and the internal standards from which you operate.

I work best with those who are curious to discover what else is possible and are committed to becoming the person who will create it. They’re willing to take an honest look at themselves, and challenge their own beliefs.

We meet privately, in person, by phone, or via video.

I work with a limited number of clients each year.

Our Agreement

  • Twelve months of Private 1:1 Coaching

  • Two 90-minute coaching sessions per month

  • Two Full Live Days — In-person 1:1 coaching and immersion

  • Unlimited Email Access to Me —Ongoing coaching support between sessions

  • Laser Coaching — Bonus, short, focused coaching calls for situations that require attention in the moment

In their words

  • “I have been so impressed with Jonathan Wakeen. He is amazingly thoughtful and insightful, compassionate, courageous, and considerably wise for someone his age. He is a highly capable coach; his approaches to topics are structured and based on best practices -- but at the same time is is always curious and attentive, actively listening and evolving. I am a semi-retired business executive and I have worked with, hired and fired, and developed countless people in my career. My high regard for Jonathan is legit and heartfelt. I would recommend him for any endeavour he set his sights on, and I would certainly recommend him as a coach or advisor for people who are looking to improve their performance or life effectiveness.”

    -Marty O.

  • “I am truly glad to have met and worked with Jonathan. He has helped establish a new mindset about myself. Before I worked with him, I had a tendency to let life circumstances put me in a negative mindset and thinking pattern, but after a couple sessions with Jonathan I began to change the way I thought when hard times hit. Using the mental tools and techniques he taught me, I was able to recognize the fear, doubt, and negative emotions that life brought upon me in that moment and change my thoughts on what the outcome would be. I am forever grateful to Jonathan for helping me relieve myself of the fear, doubt and worry that life casually brings about. With my newfound outlook on life, I believe that I can overcome anything that life throws at me by using the tools and techniques that Jonathan has taught me!”

    -Masai T.

  • “He has a unique ability to truly see you - especially in moments when you’ve lost sight of yourself. He helped me reconnect with who I am at my core and gave me practical frameworks to rebuild from there. The way he breaks things down and creates containers for thought helped me organize my mind and see things clearly for the first time in a long time.

    The impact has been real and measurable. My internal communication has improved - I’m calmer, more patient, and far less reactive. That’s translated directly into stronger relationships both at work and in my personal life. I’ve learned to build simple systems that actually work for me, which has made decision-making clearer and more grounded. I’m no longer forcing outcomes or hoping for better answers - I see things for what they are and take aligned action.

    What makes Jonathan different is his ability to hold space gracefully while also challenging how you think. No matter what you’ve been through, he meets you there - but he doesn’t let you stay stuck. His approach helped me not only rebuild but create a strong foundation I can continue to grow from. This wasn’t a temporary shift - this fundamentally changed how I operate day-to-day.

    Working with him felt safe, real, and consistently challenging in the best way. The kind of challenge that plants seeds - and if you’re willing to do the work and legitimately water them, those seeds grow.

    I’d recommend Jonathan to anyone who’s serious about leveling up - whether you’re a business professional pushing to the next level, a high performer who feels stuck, or someone rebuilding their life and trying to find their way again.

    If you’re serious about doing real work on yourself, for yourself—I can’t recommend Jonathan enough.”

    - Danny K.

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