Creating our own Wilderness

My friend Charlie is training now for sea-kayaking solo around Ireland. The passage will take weeks. Charlie will paddle 10-15 hours a day, camp ashore each night, then set off again the next morning. This will be no modest or risk-free enterprise. Seas, even in summer, can be monstrous off the rugged Irish coast. As Charlie himself admits, you have to be a little nuts to conceive of, and then live out, this kind of wild-and-woolly adventure. 

It’s a Wilderness Passage.

Charlie Daly in his Wilderness, Bantry Bay, Ireland

deliberate Wilderness Passage, with the aim—as in an involuntary passage—of attaining a deeper sense of who one is and of what is important to him. 

I salute Charlie. I think it’s great that he’s doing this. 

A case could be made that attempting to qualify for the Navy SEALs (or adopting an infant or auditioning to play Lady Macbeth in your community theater) is an eyes-wide-open form of entering upon a wilderness passage. 

Each is a hero’s journey, but embarked upon intentionally. 

We deliberately eject ourselves from the Ordinary World. Like Dorothy or Alice, we enter an Inverted Universe where everything is new and nothing we thought we knew can help us or aid us in finding or keeping our bearings. Our aim, like Charlie’s, is to return home a different person—battered a bit, and chastened perhaps, but wiser, and with a deeper understanding of ourselves and of life.

Sunrise at Lonehort Harbor. Bere Island

Charlie’s passage is a metaphor as well. Does even he know what for?  (I have my own theory, but I’ll keep my mouth shut.)

A few years ago, I ran the L.A. Marathon. Orthopaedic Hospital downtown organized a nine-month training program. We novice runners would meet every Sunday morning, about 150 in all. One Sunday there’d be a class about hydration. Another would be hosted by an expert on running shoes or the best way to set up a training schedule. It was fun. You got to meet a bunch of interesting people.

What struck me, however, was how many in the group were going through divorces or had experienced a recent tragedy of some kind. These weren’t trained or practiced runners. They had picked the marathon (and I include myself in this category) as a Wilderness Ordeal, whether they knew it or not or could articulate it or not.

And it worked, just like Charlie’s solo circumnavigation of Ireland will work.

A Wilderness Passage is baked into our DNA. No law says we can’t pick our own. 

[To follow Charlie’s adventure, click here.]


Steve shows you the predictable Resistance points that every writer hits in a work-in-progress and then shows you how to deal with each one of these sticking points. This book shows you how to keep going with your work.

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A short book about the writing of a first novel: for Steve, The Legend of Bagger Vance. Having failed with three earlier attempts at novels, here's how Steve finally succeeded.



Steve shares his "lessons learned" from the trenches of the five different writing careers—advertising, screenwriting, fiction, nonfiction, and self-help. This is tradecraft. An MFA in Writing in 197 pages.



Amateurs have amateur habits. Pros have pro habits. When we turn pro, we give up the comfortable life but we find our power. Steve answers the question, "How do we overcome Resistance?"



  1. M Moorhouse on February 1, 2023 at 1:54 am

    This story resonated with me. After an extreme health issue, I was driven to find ways of challenging myself with extreme endurance events. At first, I had something to prove, but it stuck and became part of me. It became a way of exploring my own thoughts by pushing myself to the limit in unfamiliar surroundings. It stuck and i try to do something every three months.

    • Joe on February 1, 2023 at 3:30 am

      “…pushing myself to the limit in unfamiliar surroundings.”

      There it is.

  2. Joe Jansen on February 1, 2023 at 3:29 am

    Fascinating dude, this Charlie Daly (I followed to get updates). I see from his site that he’s undertaking this wilderness paddle not only as a personal crucible, but to raise money for Parkinson’s research. Noble cause. I also see that he helped his dad write a memoir (Marine vet of the Korean, working in JFK’s White House, age 95 and still chops his own firewood). His short resume includes a stint as a “defamed Stop & Shop cashier.” Yep, this sounds like a guy you’d want to have as a friend.

    If I had a wilderness adventure to tell about, it would probably be this: the summer of 2018, venturing into the Bob Marshall Wilderness in NW Montana along a section of the Continental Divide Trail. Six days and 50 miles into grizzly country with several of my best buddies on the planet, carrying everything we’d need to live for a week.

    I’d recently taken an early out from a company where I’d worked for nearly two decades and was trying to figure out what came next. I’d had a recurrence of a cancer that had lain dormant for the past ten years. I was carrying a tumor the size of my fist and a heightened sense of mortality. Twelve sessions of radiation were waiting for me on my return. This was no hike. This was a wilderness journey.

    On top of my own stuff, I was carrying some fishing flies that had belonged to friend who had died saving his teen daughter’s life, pulling her from the water in Maui after she’d been swept off the rocks by a rogue wave. He got her to safety before going under, not to reemerge. He loved Montana but had never been on the Continental Divide. His wife gave me some of his fishing flies and I promised to leave some of them in this wilderness, with some words.

    Here’s a three-minute video of that trek, I put together for submission to a “public land owner’s film fest” (with a link to the longer version on a card at the end).

    • Joe on February 1, 2023 at 3:50 am

      Might as well tell this part, too. We were 25 miles deep in the wilderness and this was a far as we were going to get. We were running out of daylight, and the following morning we were turning back for the return trek. There was another mile to go to get a close to the 1,000′ limestone escarpment that is the most visually striking representation of the Continental Divide anywhere from Mexico to Canada. This is where I intend to leave Brian’s fishing flies.

      My buddies had run out of gas, most of them, and were already setting up camp. One of the credos we follow in bear country is “stay together; don’t venture on the trail alone.” I told Timmy, “I know, I know, but I’ve got something to do up there. I have to go.” And I went.

      I beat feet up the trail, gauging the sun’s angle and the time on my watch and trying to get as close as I could before “bingo fuel” and it would be time to turn around and go back down to camp. I was alone, making noise and giving out a periodic hearty “HEY BEAR!”

      As I found my spot and was setting my phone in the slings of my trekking poles (to video the moment for Brian’s wife), I heard rustling on the trail behind me. I startled and grabbed for the bear spray I carried in a shoulder harness. I spun around… to see Timmy coming around a bend. He saw me, stopped and put his hands on his knees to catch his breath. He stood up and said simply, “I didn’t want you to be alone.”

      • Lin Keeling on February 1, 2023 at 9:00 am

        That’s a wonderful story, Joe. You’re writing all these stories of yours down right?? No just here, but together, right?

        • Joe on February 1, 2023 at 5:13 pm

          I’d better be, Lin! <3

      • Kathy on February 1, 2023 at 9:43 am

        I felt moved by the blog itself. Steven Pressfield told of a marvelous ambition. I need to take one on myself.

        Next I read the comments and ohhh I felt touched. Thank you! And thank you for including the videos.

        • Joe on February 1, 2023 at 6:17 pm

          Kathy, with these “gifts of feathers,” it was a little eery how it came together. I was supposed to meet Brian’s wife in Columbia Falls, just east of Whitefish at the upper end of the Flathead Valley. I was on the road and planned on getting to the area the day before and camping overnight near Hungry Horse Reservoir.

          The route took me longer than expected and I could tell I was going to arrive after nightfall. And I didn’t want to be setting up camp in the dark and in bear country. So I started looking for an Airbnb. I searched in a radius of 20 miles, as far as Kalispell, and was coming up short. (Booked, booked, booked.)

          I ended finding one, and only one, available Airbnb in all of the north Flathead Valley: a single room in a house with three other single rooms and a shared bathroom and kitchen. Good enough. I rolled in about 1:00 am, showered, and laid down to sleep.

          When I got up the next morning, I gathered my gear, went out to my vehicle, and pulled out my phone to map a route to this coffee shop where we were supposed to meet. I looked at my phone, look up to the south, back to my phone and up again. This one-and-only Airbnb was only one block up the road from the coffee shop. You can see it at the beginning of the video, the red-roofed building down the hill. It felt like an odd coincidence.

          I drove down to the coffee shop (a one-minute commute) and parked. As I was getting out, my notebook dropped on the floorboard and bounced up under the driver’s seat. As I got down to retrieve it, I noticed a pheasant feather under there. Odd, I thought, it’s been nearly a year since we’d last hunted pheasant. I turned the feather over in my hand. It was in pretty good shape. I recalled some 18th- or 19th-century tradition of giving a pheasant feather as a gift. Good, I thought, now I’m not coming in empty handed.

          As I locked up and walked around the back of my truck, I noticed the Jeep parked next to me. Or rather, I noticed the license plate on the Jeep parked next to me: BIRDK9

          That makes two, I thought. You hunt pheasant using bird dogs.

          Then of course, going into the coffee shop and meeting Brian’s wife. When I presented her with the feather, she reached into her purse and pulled out a map of the Bob Marshall Wilderness and small plastic cup, the kind you’d fill with ketchup at a fast food restaurant. It was full of fishing flies… which of course are made from animal hair and feathers.

          These were Brian’s, she said as she pushed them across the table. I want you to have them. Gifts of feathers.

          I should be talking about Steve’s book in this space! 😉

      • Jackie on February 1, 2023 at 12:47 pm

        Loved the video. Appreciate the share. My husband and I fly fish. This December we took a trip to lake Ontario and fished a couple of rivers and creeks. My mom gave me a fly rod my Dad never got to use. (Dad’s unable to get out on a stream.) I took along a few of the flies he tied plus some my hubby tied. In a way, we were all there together. It was the first time I had the eyelets on the fly rod ice over. The cold was a challenge, but the experience was so worth any discomfort. Montana looks like fly fishing paradise. Maybe a bucket list adventure? Again, thanks.

        • Joe on February 1, 2023 at 6:19 pm

          “It was the first time I had the eyelets on the fly rod ice over.” Love it. There’s something about fly fishing that transcends fish.

  3. jodypaynesays on February 1, 2023 at 3:36 am

    I have the uncomfortable feeling you are standing behind me willing me to have the courage to step off the high dive. You know I have to do this myself. I know I have to do it..

    Maybe tomorrow?

  4. Ellie Clemens on February 1, 2023 at 4:06 am

    This is just exactly what I needed to read right now. I’m more of an artist than a writer, and I recently decided I want to get better at drawing portraits. So that will be my Hero’s Journey! I’m thrilled to have a name to give it, to make it more real and alive. Thank you so much!

    • Sizwe on February 2, 2023 at 7:43 am

      as the adage goes, “it’s ok to have a snake in the room, as long you have the lights ON!”

  5. Gerri on February 1, 2023 at 4:21 am

    You have given me a frame for a solo trip I am taking on the Queen Mary 2, a bucket list item as I near my 80 th birthday. I plan to write and let the ocean carry me, and stay open enough to not disappear into myself. I do enjoy playing dress up so there is that! But I have fears that I am ready to shed and a wilderness is the right place to transform.

    Thank you!

  6. Nicholas Murray on February 1, 2023 at 5:44 am

    Thanks so much for connecting us to Charlie, Steve. Can’t wait to begin following his preparations and journey.

  7. Jean Baardsen on February 1, 2023 at 6:36 am

    Have you read The Great Circle by Maggie Shipstead? I see this book as two women’s wilderness journeys. I loved the book. Here’s the amazon description:

    After being rescued as infants from a sinking ocean liner in 1914, Marian and Jamie Graves are raised by their dissolute uncle in Missoula, Montana. There–after encountering a pair of barnstorming pilots passing through town in beat-up biplanes–Marian commences her lifelong love affair with flight. At fourteen she drops out of school and finds an unexpected and dangerous patron in a wealthy bootlegger who provides a plane and subsidizes her lessons, an arrangement that will haunt her for the rest of her life, even as it allows her to fulfill her destiny: circumnavigating the globe by flying over the North and South Poles.

    A century later, Hadley Baxter is cast to play Marian in a film that centers on Marian’s disappearance in Antarctica. Vibrant, canny, disgusted with the claustrophobia of Hollywood, Hadley is eager to redefine herself after a romantic film franchise has imprisoned her in the grip of cult celebrity. Her immersion into the character of Marian unfolds, thrillingly, alongside Marian’s own story, as the two women’s fates–and their hunger for self-determination in vastly different geographies and times–collide. Epic and emotional, meticulously researched and gloriously told, Great Circle is a monumental work of art, and a tremendous leap forward for the prodigiously gifted Maggie Shipstead.

    • Joe on February 1, 2023 at 6:38 am

      Looks like a really good story.

    • Lin Keeling on February 1, 2023 at 9:02 am

      That is a great book. Too few stories about women’s Hero’s Journeys. Or if they exist, it’s hard to find them.

  8. Sizwe on February 1, 2023 at 7:57 am

    “A deliberate Wilderness Passage, with the aim—as in an involuntary passage—of attaining a deeper sense of who one is and of what is important to him.”

    It’s funny how this sentence has captured so precisely where I am currently. My life has been nothing but me choosing the sedentary lifestyle. I could never be bothered to do the difficult things that took me out of my comfort zone even though I knew they were necessary.

    shivering in terror because of the blank page in front of me? screw that, let me go get a beer and get myself into risky sexual activities. This of course led me to hate myself even more. Which led to a lot of self-defeating rampages.

    One Sunday, after a weekend of excessive sleep, tv, and drinking non-stop, “I sobered up” and with that came a terrible sense of guilt and the realization that I have been pissing away my potential. I still dont know why that finally moved me to action because there have been worse things that could’ve tipped me over but didn’t.

    Anyway, I was ready to take massive action and do the hard work, but my body and mind wouldn’t let me. they had been so used to the laziness I had accustomed them to. I didn’t know what I was doing then but I figured if I forced myself to do the hard stuff, my mind and body would be able to adapt and operate at the level I needed them to. I started taking cold showers every morning and got to the floor and worked out daily. I am soon to join a Brazilian jiu-jitsu gym, and I can’t wait to see what I am capable of handling.

    and Oh, I’ve consistently shown up for my blog every day for the past month without fail (I couldn’t even go for a week before). this might be a small win to someone else, but to me, it is the world.

    • Kathy on February 1, 2023 at 9:50 am

      You rock! You have taken the reins and you are doing it!

  9. C.M. O'Slatara on February 1, 2023 at 8:08 am

    There is something about a wilderness passage that deconstructs who we are, strips away all that is unnecessary, and digs deep to find the us we must become to survive it. Like Shackelton ripping out two pages of his bible and throwing the rest in the snow, you find what does not serve you and you discard it. What is left in its place forms the strength we need to carry on.

    • Kathy on February 1, 2023 at 9:54 am

      I LOVE that! You take OUT what does NOT scare you. Most things scare me about getting out alone into the wilderness, so that might not take long but it is a call to action… WHEN if not now?

  10. Kate Stanton on February 1, 2023 at 9:35 am

    I finally decided overthinking and waiting for the “perfect moment” is my wildnerness. Action is the only antidote. One foot in front of the other in this Liminal Space…

    • Joe on February 1, 2023 at 6:26 pm

      Kate, after I finished Steve’s book, I picked up Rick Rubin’s new one: The Creative Act: A Way of Being. I’d love to listen in on a conversation between those two guys. There’s harmony between what each is saying. Steve talks about being in your spot consistently enough that the Muse takes pity and shows up. Rick talks about creating that habit of being in the same spot every day, creating an empty space or a “vacuum,” into which flows what the universe has to offer (Steve’s talked about the ideas “being out there” and us grabbing them down).

  11. Kathy on February 1, 2023 at 10:23 am

    Before my precious husband passed in April, I followed this YouTube of a woman who walked the Camino de Santiago. I posted her adventure daily on my Facebook, feeling in my soul that I would one day take on the same adventure. I actually went through her walk twice on my FB. I FELT IT. She and I became friends and at Christmas time she actually sent me a Camino shell she got on her journey.

    I was soo into it! I followed her advice on what pack, clothing, walking sticks, even essential oils to mask the smell of other humans sleeping together in youth hostels, the Camino way. I was into it!

    Deep down I was never really sure I would actually go though. Was I really that woman?

    I was going to the gym, lifting weights and trying to gain strength in my 70 year old body. Then COVID hit. Then my precious Denny , a Vietnam Vet, suffering from all the things that agent orange had to throw on one human being, caused the end of his life.

    I have not been able to stop crying or accept the defeat on not keeping him alive, if just for another year. I was always able to find new approaches for all he suffered from.

    Denny was an avid surfer and a wonderful song writer. He also taught Jr. High ant a school and High School in a storefront at night, in gang zones, bringing failing grades to A’s and B’s. He started a surf club for those kids who rarely got out of their gangster town. He told me that the first time he took those kids to the beach, they asked where the gangs were. “There are no gangs here,” he told them, “This is the ocean.” When he passed an unbelievable amount of rescued, now grown with kids of their own, former gangsters, wrote on his FB wall of what he meant to them. HUGE, ya know? HUGE.

    So here I am now, alone with the daunting task of getting back up. This particular blog; the idea of actually calling myself out on being stuck, doing all that Denny ever hoped for me, has helped and reminded me of my longing for the Camino. Thank you.

    • Kathy on February 1, 2023 at 11:07 am

      Link to my friend walking into Santiago.

    • Kathy on February 1, 2023 at 11:14 am

      And this is Denny, singing one of his songs. I posted this a few days before he passed on to his lighter body. His voice is weak because he was not well but he wanted to record all his songs. One by one we will get videos done of all of them.

      I think the message is that we still have time for adventures and Denny does not. Have an adventure and remember his name.


      • Jackie on February 1, 2023 at 1:39 pm

        Thanks for sharing the song and video. Beautiful. I cheer you on. Make it happen.
        I will remember Denny’s name and speak it on my next adventure.

        • Kathy on February 1, 2023 at 2:05 pm

          Thank you!

      • Sizwe on February 2, 2023 at 9:41 am

        I love the scenery in the video, especially the men of service in the shadows. I guess that’s somehow tied to his time serving in Vietnam. may his soul rest in peace and you continue finding solace in the body of work he left. I am genuinely moved.

    • Joe on February 1, 2023 at 6:31 pm

      Thanks for sharing your story, and Denny’s singing, Kathy. Glad you’re here and talking!

  12. Maureen Anderson on February 1, 2023 at 10:30 am

    Loved the video, Joe! What a feast for the eyes!

    Has anyone else heard this one? “Something only becomes an adventure once you start writing about it.” I moved to the literal wilderness a few years ago, yet nothing here has been as grueling as trying to get from Scranton, PA, to Omaha, NE, on a Greyhound bus.

    I’m starting to think it doesn’t matter so much WHAT you do as THAT you do it.

    • Joe on February 1, 2023 at 6:33 pm

      I hadn’t heard that one, Maureen, but it makes sense. Telling the story.

  13. Kathy on February 1, 2023 at 10:31 am

    I need to clean up a sentence. My husband ultimately passed due to ischemic heart disease and COPD. Both Agent Orange related. His main and most painful issue was small nerve fiber neuropathy and peripheral neuropathy, which were extremely painful. He also survived bladder cancer. Denny was home bound for some 10 years and near bed bound for his last 4 years. He would have given anything to hike anywhere or to catch another wave.

  14. Nom de Plume on February 1, 2023 at 1:31 pm

    Bless you, Kathy. I wish you peace, and solace with his memory.

    And for everyone, a reminder: Adventures happen to the adventurous.

    • Kathy on February 1, 2023 at 2:06 pm

      Thank you 🍃🌸🍃

  15. Jackie on February 1, 2023 at 1:31 pm

    Steve, thanks for the wilderness adventure here and in your book. Two days ago, every version of the wilderness, self-imposed or otherwise, led to a realization of why I was still beating down the same jungles around me. I named the theme of my story and was able to put it to rest.
    Let’s raise a glass of whatever floats your boat to Charlie and Dominique (in support) on their sea journey. May the skies be clear and the seas calm. And Na Zdrowie to everyone who shows up on Wednesdays.

  16. Christine Daly on February 1, 2023 at 4:22 pm

    Charlie’s voyage is also referred to by him as, “don’t tell Mom I’m kayaking around Ireland.” Never forget to bring a sense of humor to your wilderness adventure.
    Charlie’s Mom

    • Joe on February 1, 2023 at 6:53 pm

      Charlie’s mom is here! Hi, Christine! So, Charlie’s busted? If you’re going to ground him, you’d better get to him before he hits the water. 😉

  17. Ed Hinman on February 4, 2023 at 9:38 am

    Another great one, Steve! We are here to push our rock up the hill; we are meant to do hard things! And when we do, nature smiles upon us and gives us all those good vibrations.

  18. ROBYN WEINBAUM on February 17, 2023 at 8:40 am

    when my marriage fell apart, i took up, after 30+ years, bicycle riding. i used a $79 bike to commute to work, 3-1/2 miles each way. A few years later, I met the person who became my 2nd husband, after the divorce, after the homelessness, after the unemployment, after the foreclosure, after the bankruptcy [yes i lost EVERYTHING] on maybe our 3rd or 4th date, he told me about this charity bicycle ride, that was 75ish miles each way, the BikeMS ride. i decided that was My Goal. to go from a casual rider, riding maybe 10 miles Every Day, to being able to ride 75 miles and then 75 back the next day. i created a training schedule. I joined a group to learn group ride etiquette. and i rode, and i fund raised, and i think it may have saved my life.

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