On The Hunt For Wisdom With J.W Bertolotti

Philosophy and wisdom go hand in hand. It’s a pursuit of wanting to learn how to live appropriately and using techniques that are practical in daily life. J.W Bertolotti has dedicated himself to this path through the Perennial Leader Project and his podcast In Search Of Wisdom.

It was a pleasure to interview Bertolotti about his experiences with philosophy and as a former air force veteran he’s got plenty of stories to tell. In this interview, he shares his thoughts on Stoicism, love, suffering and what it means to turn knowledge into wisdom. 

What was your first experience with philosophy and how has your interpretation changed over time?

It was about the time that kindles came out, so something like 15 years ago. I’d downloaded some books and Epictetus’ Enchiridion was one of them. I wouldn’t say I read it from cover to cover but it did help with my interest in getting to understand what wisdom is. 

And has your interpretation of Stoicism evolved since then? 

Having spent my adult life in the US military, I was initially attracted by the idea of perseverance in Stoicism. But the more I got into it, the more I became focused on the philosophy of life perspective and being interested in different types.

I enjoy finding overlaps between multiple ways of thinking, whether it’s Buddhism or Christianity. It gives me a deeper understanding of what wisdom can be. 

Considering you were an Air Force veteran, did that experience shape your personal philosophy?

It did, especially when it was for more than two decades. That kind of thing has to shape you. With that experience I connect it to philosophy and the idea of always moving and being uncertain of what comes next.

If you think of Marcus Aurelius, his image of what’s good for the bee is good for the hive comes to mind. Philosophy encourages us to be part of a greater organism and that’s what it felt like at that time in my life. 

Wisdom is a big subject that you explore constantly in the Search For Wisdom podcast. In your view, what is the difference between knowledge and wisdom? 

That’s a good question and I appreciate all the listeners to the show. The podcast was inspired by a desire to improve my own character and on the subject of knowledge and wisdom there’s this anonymous quote that comes to mind.

Knowledge is knowing a tomato is a fruit and wisdom is knowing not to put it in a fruit salad. Wisdom is practical and there’s a mundane, daily life aspect of wisdom I’m trying to get at. I’m not a trained philosopher and I’m not necessarily into some of the abstract questions that aren’t as applicable to daily life.  

I’m interested in the debate between self-help vs philosophy. What are your thoughts on using philosophy as self-help and an internal resource and then using it externally to improve your community? 

I like that question Jamie. I tend to think of poets like Rumi and Tolstoy and the idea of changing the world must first come with changing yourself.

It’s the idea that we’re all connected by embarking on some sort of self-improvement path and in turn we help to improve the whole i.e. our communities. 

You’ve mentioned Marcus Aurelius is a philosopher you admire. Which other philosophers have had a big impact on your life? 

I’m a big fan of Seneca right now. There’s obviously a lot of content that Seneca has with his letters and another guy I’m into is Anthony de Mello, an Indian psychologist who wrote a book called Awareness. 

You provide consultation and coaching and how do you bring philosophy into it when you’re working with clients?

There’s a small portion of philosophy I bring into this. But what I have found is that leadership coaching aligns closely with the Socratic method of asking questions.

It’s asking questions that best serve the individual and the life they’re looking to lead. 

On the subject of asking broad questions. What’s your interpretation of this question: Does talking about philosophy make you a philosopher or is that a title that is given by someone else? 

It all depends on your definition of a philosopher. There’s the idea of loving wisdom and I really connect with the path of being a student. It’s constantly learning about how to follow the path to The Good Life. 

Cicero famously said that to philosophise is to learn how to die and I interpret that thought as to philosophise is to learn how to live. What’s your take on it? 

I think it’s two sides of the same coin. To learn how to live is to learn how to die, just as learning how to be wise is learning how to love. 

If we’re thinking of the cardinal virtues of Stoicism, they could all be categorised under an umbrella of love or simply acts for the common good. 

Another thing that speaks to me is the idea of whether suffering can be good in a philosophical sense. Can it be a ‘good’ thing if it’s deliberately chosen in the pursuit of improving your character and going with the concept of amor fati?

You are getting at the perennial questions here. You mentioned amor fati and I think there is certainly some element of finding meaning in suffering. Obviously, it’s easier said than done and I’m reminded of Viktor Frankl’s Man Search For Meaning when he said the best of us didn’t make it out. 

Personally, I’ve had a life with an absence of some real suffering and I want to be cognisant of that when compared to other people’s experiences. 

I also wanted to touch on philosophy and parenthood. As a father yourself, what techniques would you suggest for making philosophy more accessible to a younger audience? 

First, I’ll give you the obvious answer of trying to model the behaviour you’d like your kids to emulate. So, it’s not getting upset at things that are beyond your control etc. 

I also think it’s good to have a lot of books around and make them visible in the home. 

What are some future philosophy projects you’re working on? 

I’d like to put together some free courses that can continue to help with people developing their own kind of wisdom. Any paid content I develop I’d like to donate the proceedings to charity and feel super blessed to be in that position.

This may become a Patreon community or a book club where ideas can be shared. 

What’s your best advice for anyone who wants to start a philosophy podcast?

If it sounds interesting to you or something enjoyable I would say do it. There’s also the idea of whether this is something you want to do or something you have to do. It’s worth contemplating the question of is it something you want to do or will it potentially fade?

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