What Does It Really Mean to Follow Your Dreams?

Jack Uldrich
6 min readOct 24, 2020


We frequently hear the phrase “Follow your dreams.” Often, it denotes the idea of pursuing one’s worldly passion. There is nothing wrong with this and, generally, it’s solid advice. I am, however, interested in the phrase “Follow your dreams” at a deeper level — at the level of the soul.

In January of 2019 my father died. His death wasn’t expected but, being 83 years of age, it didn’t surprise me either. Shortly thereafter, I began keeping a journal. I didn’t connect my journaling to his death at the time. I have subsequently come to understand that the death of a parent causes some people to reflect upon — and even confront — their own mortality. This “inner work,” in turn, can then trigger deep “soul searching” and/or a crisis of personal meaning.

In my case, my journaling was a tool of spiritual growth. I scribbled passages from a variety of wisdom traditions. Growing up Catholic, I had a fair number of passages from the bible and Christian mystics, including Julian of Norwich, Meister Eckhart, Hildegard of Bingen, William Blake, and Thomas Merton. I also filled up my pages with passages and quotes from Sufi mystics, Buddhists, indigenous wisdom keepers, and poets such as Rumi, Emily Dickenson, WH Auden, David Whyte, and Mary Oliver.

Oddly, I found myself using my journal to document some of my dreams. This was a new development because, previously, I was the kind of guy “who didn’t remember his dreams.” When I did recall them, I wasn’t terribly introspective about them. (Truth be told, I still have a difficult time recalling my dreams unless I journal about them immediately.)

Recently, I returned to two dreams I had on August 2 of this year. What’s interesting is that I would have completely forgotten about them had I not written them down. It was as though the dreams existed only on paper. Yet, when I re-read it, my consciousness sprang to life and said, “Yes. I remember that dream!” Below is how I documented the dreams in my journal:

I had a strange dream last night. It began by me parachuting down to earth from a ridiculous height. In my dream, I fell for minutes before landing in an unknown landscape.

In my next — and complementary — dream, I was sitting in a coffee shop searching for visual images of the unknown landscape where I had landed.

From behind me, a voice said, “‘The Badlands’ that’s the place where I just was in my dreams.”

The man walked past me and I said, “Excuse me, did you just say you saw this landscape in your dreams?”

The man turned to me and his skin was tanned but covered with an ashen sheen — I realized then that the man came from the afterworld.

He was about 60 years of age, wore a leather coat, and had a British accent.

He then said, “The Badlands, Monarch Butterflies, and Whales.”

With that the dream ended.

What does this mean? [End of journal entry]

The reference to the Badlands was pretty clear to me. Although there are the “Badlands” of South Dakota as well as the “Badlands” of North Dakota — I knew at an intuitive level it was the latter. This is for two reasons. First, in 2004, I wrote “Into the Unknown: Leadership Lessons from Lewis and Clark’s Daring Westward Expedition.” The area I described as “the unknown” in the book was also the “unknown” landscape I saw in my dream. Second, I “know” the Badlands refer to the Badlands of North Dakota because of what I can only describe as a mystical experience I recently had during a pilgrimage into the BWCA (Boundary Waters Canoe Area) of Northern Minnesota.

My dream’s references to the Monarch butterflies and whales had me thoroughly confused until a few days ago.

Through what I can only attribute to synchronicity, I was reading Belden Lane’s book, “Backpacking with the Saints: Hiking as a Spiritual Practice,” when he made mention of Bill Plotkin and “death lodges” in a chapter entitled “Dying: Mudlick Mountain Trail and the Cloud of Unknowing.” The phrase “death lodge” jumped out and, again, at some deep intuitive level, I understood I needed to experience something akin to a “death lodge.”

As I continued reading, something Lane wrote about the “cloud of unknowing” sent me back to my journal — which is where I found and “re-remembered” my dream about the Badlands.

I had forgotten about the “tanned” description of my dream visitor and I was even more surprised by my description of the man as a visitor from the “afterworld’. This is because I can’t say I have any belief, understanding, or knowledge of “the afterworld.” (Honestly, I even feel uncomfortable at this stage of my journey writing about such things).

Still, the references to Monarch butterflies and the whale made no sense to me.

I continued to read Lane’s book and the very first sentence of the next section of the book — after the chapter mentioning Plotkin — begins with this sentence, “Once the hero has trod the dark path or descended into the belly of the whale, says Joseph Campbell, his journey concludes with his bringing the runes of wisdom or the Golden Fleece ‘back into the kingdom of humanity’.”

The phrase ``the belly of the whale” hit me with the force of a sledgehammer. In this context, the “belly of the whale” is a metaphor for “the descent,” a “death lodge” or a place one goes to “die to oneself.”

I now knew I was meant to go to the Badland’s for this purpose.

The meaning of the Monarch was revealed only a few pages later when Lane described how a caterpillar can only become a butterfly by going into a cocoon and dissolving to itself. Then, through a still only vaguely understood process, the caterpillar somehow restructures and reconfigures itself into a Monarch butterfly — a creature which is, paradoxically, completely different from the caterpillar but composed of the same raw material.

“That’s it,” I thought. “The only way I can become the “Monarch butterfly” I am meant to become is to go into the belly of the whale — or a “death lodge” — and “dissolve” or die to my old self, and I am meant to do this in the Badlands of North Dakota.

So how did my dream turn out? Here’s the answer: I don’t know! This is because I leave for the Badlands tomorrow. I have no idea what will happen or what is meant to happen. I am simultaneously terrified that I will spend a week on the cold, bleak, barren, windswept plains of western North Dakota with nothing to show for it; and equally terrified that I will come back a completely transformed person who has to leave everything he has known behind. Perhaps, the truth will fall somewhere along the spectrum of these two extremes. I simply don’t know.

What I do know is that to literally follow your dreams is exciting, terrifying, and beautifully mysterious all at once — and my soul eagerly anticipates the adventure.

Jack Uldrich is the author of Business As Unusual; A Futurist’s Unorthodox, Unconventional and Uncomfortable Guide to Doing Business. He is currently co-authoring a forthcoming book, “Generation RE: The Guiding Spirits of the Coming Renaissance,” which he now understands is meant to be informed, in part, by his own experiences.