Brilliant Attorney Profile: Hale Stewart Insurance Lawyer and Moving Meditator

One of the most common complaints I hear from new meditators is that they “can’t sit still.” My common refrain is that “you don’t have to sit still; you don’t even have to sit!” I’ve written about this before, but I am not sure I am the best emissary of this message. Stillness has never been the problem with my practice. Instead, I’ve craved it and relished every bit of silence I could get because my problems were excessive thoughts, doubt, and self-judgment. 

So this week, I am going to let the story of my friend Hale Stewart, an insurance lawyer and moving meditator, make the point. I have never met Hale in person but became acquainted with him on LinkedIn. He is the Vice-President of Recapture Insurance, an alternative risk financing wholesaler and he posts regularly on insurance topics. Because that area is adjacent to my own, which includes some insurance defense work, I became connected with Hale and his posts started showing up in my feed. Hale’s knowledge of insurance so vastly exceeds my own that I often couldn’t contribute in a meaningful way to his content, but he had a good sense of humor and always had a joke or funny GIF to offer on my posts about mindfulness. 

I never expected Hale to tell me that he was interested in meditation. His sense of humor told me he was a pretty no-nonsense type of guy and I know he told me outright at least once that he wasn’t the type to sit and do nothing. But, one day, out of the blue, Hale messaged me to say that he appreciated my blog posts because they were practical, simple, and had helped him. This made me super curious, so I asked Hale to talk about his mindfulness practice. Despite Hale’s prior intimations that meditation wasn’t for him, I found out that he had created a unique, effective, and robust practice for himself.

Hale told me that he meditated during his daily cardio workouts on the treadmill. He had started this after thinking about spirituality and stress management for a while. In addition to being an insurance lawyer, Hale is also a former professional musician. While that experience exposed him to and made spirituality a part of his life, the steady march of time and the stresses of the current day caused him to begin exploring meditation as a new way to take care of himself.

After searching the internet, Hale found some guided meditations to pair with exercise. Hale said he enjoyed them because the teacher didn’t use a wispy, mystical, yoga teacher voice, so he could just do the practices without distraction. By doing those practices for a while, Hale learned to guide himself through the practice and he now meditates on the treadmill for nearly an hour most days. His practice includes body scan to get into his body as he begins his workout, breath focus to stay present with his experience, and visualizations of rainbow (“ROYGBIV” as Hale called them) colors. 

Hale, it seemed, didn’t know or care that this was impressive. He didn’t seem to notice that a daily practice of that length of time was incredibly robust for a new meditator. He also wasn’t too focused on the fact that his practice ticked some important mindfulness boxes (mental focus, body awareness, and breath work) or that rainbow colors have traditionally been associated with the chakra bodies from yoga philosophy. Instead, what Hale cared about was feeling better, enjoying the workout, and getting benefits. Though his practice is not yet a year old, Hale reports that he is already reaping those benefits, including feeling more present and focused and rushing less.  

Several things impressed me about this story. First, Hale’s willingness to explore and try something new is commendable. People new to meditation can take the practice and themselves too seriously at first, which can impede the curiosity and playfulness needed for the practice to offer its benefits. Hale didn’t do that and instead explored to see what was out there and played with the practice to make it work for him.

As someone who took way too much time reading and thinking about meditation before I tried it, I was also impressed that Hale didn’t need a lot of theory to get started because he trusted himself. Many people new to meditation worry initially about doing the practice “right” but Hale built a practice based on what felt good to him. This isn’t to say that theory is unimportant or that teachers and books are useless. On the other hand, though, it demonstrates that there are many paths to mindfulness and that we don’t have to know the path perfectly to walk it well. 

When we talked, Hale confided that he had never thought of himself as the type to meditate because he wasn’t someone who could just sit there. Rather than let this idea hold him back, he paid attention to what he needed and embedded the practice into his life, rather than conforming himself to what meditation was “supposed” to be. So, now when people tell me that they struggle with meditation because they “can’t sit still”, I don’t have to convince them. I’ll just remind them that there are lots of ways to meditate and suggest that they go talk to my friend, Hale.

F. Hale Stewart JD, LL.M. is a Vice President of Recapture Insurance, an alternative risk financing wholesaler.   Hale has been involved in alternative risk for 12 years.  He has written two books on the topic (U.S. Captive Insurance Law and Captive Insurance in Plain English) and provides periodic commentary for IRMI.  A former professional musician, he remains an enthusiastic amateur jazz guitarist. You can learn more about or follow him on LinkedIn.

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