Jorge B, CEO, Bay Area, CA, USA
Updated July 2025
What's the obstacle that would have prevented you from investing in coaching?
Knowing about coaching, and knowing what coaching could do, were pretty basic obstacles. It's not something that was spoken about when we started working together. You might have heard about a coach here and there, but always said, “Hey, this doesn’t apply to me. Why would I ever need it?” It wasn’t an aversion or a negativity; it was basically a alack of knowledge. Once I found out about it, I was pretty gung-ho.
The other thing that probably was missing was a level of humility on my side. To say, “Hey, this is not something I can do myself.” I was very much someone who would always just pick up a self-help book and read it and work through it. And I picked up a self-help book, which you know, that was actually very good, had a whole process associated with it, and it felt a little bit overwhelming to do the process by myself, which is how I came to look for a coach more actively. I think that was really important.
What did you find as a result of investing in coaching with me?
I discovered that I wasn't alone, that there was help, that it was possible to have someone that's objective and on my side.
The way I experience coaching, it's very much somebody who's in your corner, who's giving you help on the lay of the land. It literally feels like a boxing ring, where to throw the punches, what the opponent's doing, very much in your corner, but also has the ability to look at the situation much more objectively than I am able to by myself.
Over time, the steady progression, it really becomes an interesting relationship because, as you develop it, there's a trust and confidence in the person and in the process that makes it much easier to take the advice and to act on it. For someone like me that is really more extroverted and does just do things in their own brain, it's really, really helpful.
What specific feature did you like most about my coaching process?
I liked the even handedness of it, the way your process is grounded in reality and in basic human behavior. It doesn't appear to me to be really prone to fashion and to what's hot and what's not, but it boils down to first principles, and I like that a lot.
I like the steadiness of it, and the fact that there's always a pretty relentless search for a root cause, which is, I think, very interesting. Then, it’s, “How do you address that? How do you tackle that root cause and getting your life where you want it to be?” That's not superficial. So this first principles, root cause thing, I think that's particularly why I've stuck with it and why I want to continue with you.
What were three other benefits from working with me?
The first one is a clarity in action for me. When we started, I had very much felt like I was stuck in the mud. So an initial benefit very clearly was just getting into action in an order of priorities that actually met my expectations or really met my requirements. So we were able to remove the layers of the onion in the right sequence so I could actually take action.
The next one is actually speed. Once that happened, I was able to move quite quickly into the next phase. And I was actually reviewing this the other day. I thought, “Oh, I thought there was more time from between we started coaching to when I took my first big actions.” But no, was actually only a few months. And that surprised me in hindsight, because it felt like it was a large.
And the other one is having you in my corner for future moves just feels like it's worth gold.
Would you recommend someone else work with me? Why?
Definitely. I would recommend anybody that is not able to see clearly what the next step is, to work with you, because that is really one of your strengths.
I think anybody can use a benefit of coaching at any point in time. But with you specifically, I think getting to root cause of: Why am I blocked? Why am I not moving forward? Why do I feel stuck? I'm in a certain situation in life that I find difficult. How do I untangle myself from it? Or is it something I have to go through? Is it just part of life?
I think I think talking through those types of situations is very important. And more clearly, I mean, in my case, it was, “Do I stay at the job that I have, which is a very good job? Or do I go for something else and bigger or different? Do I stay with the person I'm attached to or not?”
And, you know, all these questions, which are super important and big, I felt that it was really, really great to have you in my corner and backing me. I think that anybody that's in any situation even remotely similar would clearly benefit from this.
Is there anything else you'd like to add?
You're really fabulous. It takes a little bit of time to build up the trust and experience.
Don't expect things to happen overnight. These things take time. Sometimes it takes time to realize what you need. Don’t expect that it’s just a magic wand. Coaching is very powerful, but it takes time to build the relationship, the trust, to do the entire communication back and forth.
Treat it like it's a muscle. Keep exercising it because it's really worthwhile. The outcome really is very positive. Give it a try; I highly recommend it.
2023
Before working with Jason, life was fine, but there were some challenges, and these challenges probably took a little bit of the joy out of life, both at home and at work. And Jason really helped me work through systematically, work through those challenges in a way that was positive and had a positive outcome on my life, both personally and professionally.
I really liked the process of working with Jason because it was systematic. He is obviously approachable, non judgmental and understanding, and he has a deep wealth of experience and is remarkably wise, and the process really was infused with all of that. It was a joy to work with him and work through issues in a way that I hadn't worked through them before, and it was also very rewarding to see progress as we went along. I didn't have to wait too long to see some progress and then greater progress as the as we completed our sessions together.
What is life like now? Life has taken a turn for the better. For me, the uncertainty I had around my personal issues have been resolved. That doesn't mean there aren't any challenges, but the way I'm addressing the challenges is different than before, and I think, more fruitful with more determination and with a greater sense of direction. And the same thing goes for work. The rut I was in has been cleared, and it's more a question of, where do you want to aim your life towards, and not so much. How do I get out of this situation I'm in? I'm out of the situation now.
The question is, where exactly do I want to end up? And we're still working on that, and it's still a pleasure, and I intend to keep Jason as a coach for a long time because of that reason, it's been very helpful. If you're on the fence at all, I highly recommend you calling Jason and seeing if it'll work for you as well as it did for me. Thanks.