Turning 40 and the Practical Applications of Discomfort

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James Wisdom realized at age 40 that he was going to die someday and, while he loved what he did and the life he had built, he felt like he was going through the motions in a lot of ways and doing all the things he was supposed to be doing. So he made some changes and his life looked very different at the end of the year than it did at the beginning, which included changing his career, ending a long-term relationship, changing his friends, and even where he lived and his lifestyle. He talks a lot about discomfort and how it can be a useful feeling, despite how much we all work to avoid it. James uses the language of art and philosophy to reflect on where he’s been and where he’s going.

Guest Bio

James Wisdom is a nationally exhibited and world-renowned fine artist, illustrator, and tattooer. James, is currently enjoying a thriving art, illustration, and tattooing practice; he is also an educator, scholar, and author. He received his Bachelor of Fine Arts degree with a specialization in oil painting from the American Academy of Art and his Master of Fine Arts degree in studio arts from the University of Illinois at Urbana-Champaign. In addition to his artistic interests, James has contributed to various publications such as Ninth Letter, Studio Visit Magazine, and he is a contributor to the upcoming Anthology of Hegel’s Phenomenology of Spirit (Philosophy Portal, 2022). He hosts a weekly drawing and tattoo-themed stream that can be seen on Reinventing the Tattoo, streamed on YouTube, and Facebook.

Meet James Wisdom

Forty was a big year of transformation for James Wisdom. He was in a long term relationship, a full time instructor at an art college in Chicago and, though he loved what he did and where he was, he felt like he was going through the motions in many ways. Then came the realization that he was forty and was going to die eventually and that he was doing all the things he thought he was supposed to be doing. He resigned his teaching position and went back to his true love, tattooing.

Quitting his job gave James the space to be creative and to build something new, even though he didn’t know exactly where he was going. He became more open to friendships than he had been in the past and felt like there was a wide world of opportunity for him to step into.

James has a weekly tattoo and drawing themed podcast that streams on YouTube and Facebook in partnership with a tattoo education company. He says he’s teaching a lot of the same subjects he taught at the art college, without the barrier of tuition. After years of study and teaching, he developed his own interpretation of the fundamentals and he’s presenting that in an accessible way now, which he finds rewarding.

He has also separated from his long-time partner and moved out of Chicago. His new tattooing job is in Indianapolis, about a 4 hour drive and a world away culturally from Chicago.

Living Intentionally

Around the time he turned 40, James began to reflect on who he was and what he was doing. He wondered about destiny. He appreciates where he came from and knows that he wouldn't be where he is now without all of the things that came before. He tries not to live with regrets. He says it’s difficult to accept who you are and everything that you’re responsible for. He thinks that if you’re demonizing yourself or your past, then you’re not appreciating the big picture.

James is doing his best to accept and be present for the transformation taking place in his life now because, he points out, this part will only happen once in this lifetime. He’s optimistic for the future because of the seismic shifts he’s already experienced. They’ve given him a new perspective of what’s possible. So rather than regretting past choices, he approaches those reflections with the perspective that he’s learned from those experiences and won’t make those choices again. That’s how we can accept who we are and not have so much resentment for ourselves and for others.

If we’re not being our true selves, or who we truly want to be, it’s probably out of fear. The way to overcome fear is experience, learning how to navigate situations and doing better when we face them next.


Another thing James reflected on was his values and how the path he had been on was not in alignment with things he valued. He values family and friendship and says there were a lot of ways that he had neglected being a good family member or friend. He feels like, in his earlier years, he had focused on seeking pleasure and looking for the easiest way, even though he values hard work and excellence. And while pursuing these values may cause discomfort, there’s pride in not taking the easy road and delaying pleasure seeking until you’ve accomplished what you set out to do.

This is something James learned through drawing. One of the things he teaches is how to draw the human body. People tend to want to start with the thing they’re most attracted to, whether it’s a foot or a fingernail. And while it may be pleasurable to start with that right away, you’ll end up with a better result if you follow the process and build the foundation.

James thinks there’s a lot of value in delaying gratification, laying the foundation and preparing a place for the thing that you want.

Visual Art is a Language

James is philosophical about the role of visual art in the world. He says visual art is a language. There’s space between us as individuals and we can fill it with language and other forms of expression, including visual art. He says visual art resonates with people because it speaks to their consciousness.

James thinks artists are important because they create culture. And while people may be afraid of calling themselves “artist,” he thinks that also comes from fear - being afraid of judgment and criticism. But the simple act of practicing your art helps you become more comfortable with who you are. “The more familiar that you are with how it is that you make things, the more comfortable that you are with it, the more confidence that you show. And confidence is sexy.”

There’s something rewarding and freeing, James says, about having the confidence to use a language, whether it be spoken, drawn or another form. But using any language requires practice and experience and that requires being uncomfortable sometimes.

Life is a Journey

James says that, while “life is a journey, not a destination” is a slogan that’s so common it’s become banal, the experience of those words is something else entirely. He says that if you’re planning for something in the future, whether it’s retirement or getting into heaven, you don’t have to be as present because you’re focused on the destination. You can become detached, alienated from now. Living in the future can be just as detrimental to us as living in the past.

The more interesting thing to do is to be present in your daily life. If you focus on enjoying the journey rather than the security of the anticipated destination, the reward is the experience. If you overlook that in your hurry to get somewhere else, you’re missing a big piece of life. And, besides, you’re not guaranteed to reach that anticipated destination.

James met a Buddhist who said to him, “"The next time that you're sitting in your car and there's traffic all around you. Don't ‘I'm in traffic.’ You have to say that ‘I am the traffic.’” We’re always a part of where we find ourselves and once we separate ourselves as being different from what’s going on, that’s where we can become resentful of others and feel a need to escape. But if we’re willing to be present, we may find that the fear was worse than actually being present.


The Forty Drinks Podcast is produced and presented by Savoir Faire Marketing/Communications

James on Instagram

James Wisdom Art Website

Reinventing the Tattoo Online Course

James Wisdom Tattoo Website

James Wisdom Linktree/links

Tell me a fantastic “forty story.”

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