Between two dreams
some musings on life transitions...
Last year, I sold my company. It was a milestone to celebrate (in theory). But really, it just brought on a wave of crises I didn’t see coming.
I spent most of 2024 lost in a wasteland of my own making. It was disorienting and destabilizing. Every last bit of fear and ego that I had allowed to play a starring role in my life came to the surface. It was both a painful and beautiful process.
I write now from whatever the opposite of the wasteland is (heaven?) for the first time in a long time. Only because I believe it could be helpful to someone that finds themselves in that unique period of life between two dreams.
Old habits die hard
For the first half of last year, I pursued an old dream with new vigor. I started running at a new business idea with people I love and then ultimately, to my own surprise, decided it wasn’t for me sometime in July. It’s hard to describe exactly why I needed to walk away considering it had all the elements of what I’d said I wanted, but – I just didn’t feel it.
I spent the next half of the year trying to come up with an idea that I could go chase. I had literally 20-30 solid ideas that I could imagine myself going all the way for. But still – I just didn’t feel it.
That’s when things got particularly dark. So I did all of the cliché things one might do when everything seems to be upside down – mushrooms, lots of breathwork, meditation, journaling, running, and traveling, diving back into a relationship, white board sessions with friends, etc.
It was like I was trying to solve the equation of my life, but the numbers had become hieroglyphics. So the math just didn’t math anymore. But still, I clung to anything that felt like a number.
The truth is, not having a “big thing” to shoot for was extremely hard for me. I had grounded my identity in the pursuit of some big overarching goal for the last many years. Not having that — and clearly no longer “wanting” to have that — made me feel like an utter failure. I had absolutely no idea who I was anymore.
It was the first time since moving away from home 10 years ago that I imagined what it’d be like to move back. I was wondering if my hero’s journey was coming to an end, and it was time to go back to Pride Rock.
The beginning of “the shift”
Every time I’ve caught up with a friend in the last year, the first thing they’d ask is: “So what are you doing / gonna do now?” It always came from this place of love and curiosity. And still: I could not answer authentically. I downright lied. I shirked the question. I made up some stories about becoming a writer or starting another company.
All because, I just didn’t have the words for what was really going on with me.
I don’t know about you, but I have often found it impossible to describe a massive transition when I am deep inside of one. This is what makes living on the edge of truth so damn hard. It’s isolating. And also horrendously difficult on the people around you. Because you are discovering the truth about yourself in real time and trying to translate that to them without hurting them is… well, impossible.
It’s also shape-shifting constantly. Life, I mean. Things are changing all the time, even when we don’t want to acknowledge it. Even when we have the structures of business agreements, marriages, and mortgages in place. Things are just flowing, and promises and commitments we’ve made can evaporate overnight. It scares most of us to admit this. But it’s true.
And it was true for me. Part way through the year, I began to notice that my priorities were shifting. I had become disillusioned with the creator economy and Los Angeles. The ambitions that were once important to me no longer felt important. The character that I had developed to be able to take all of this on felt flimsy.
And yet, I could not say this to people because my body and mind had not yet caught up and I was not living in alignment with any of it. I was still living split-screen, halfway in each world. I was feeling something in my heart, but not yet able to truly articulate it or live it. I was also terrified of the consequences of admitting any of it.
This is not the first time I’d been through a massive transition like this. In 2014, after my mom died: same thing. In 2018, after I quit my only ever real job: same thing. I went through dark periods in the wasteland then, and last year I just couldn’t believe I was “back” in the same kind of space again. So, I denied it. I refused for months to let go of what clearly needed to be let go of. I believed I was more evolved than those previous times, and that nothing needed to shatter or be reborn. This made it harder, and prolonged the inevitable.
Making death a friend
Picasso said, “every act of creation is first an act of destruction.” As much as I don’t want to believe that, I do.
I have found that nothing is stable or secure in this life but my (and your) spirit. And the very attempt of creating stability and unbreakability outside of ourselves in the “real world” always ends in destruction. Because this attempt is born of fear, and anything born of fear must someday fall away.
The thing about death is that it doesn’t make sense to the human mind. The mind negotiates and bargains, and attempts to create situations where death is impossible. It tries to tell stories to make it go away. And still… it comes.
A simple fact of life is this: you must have the courage to die before you die. To your old self. Your old life. Your ego. Your fears. The beliefs and stories you’ve held dear. You must invite in death like an old friend for tea, and somehow make peace with the idea that nothing is forever.
And it’s not enough to do this ONCE. Or TWICE. Or even THREE TIMES. You have to do it all the fucking time. For as long as you live, you must allow the space for death to coexist with you. You must allow yourself to die and be reborn.
I believe our collective denial of this fact is the root cause of so much of our suffering. It is anti-nature. It is anti-life to disregard death.
Death imbues this life with deep meaning. It’s what makes the movie feel so real. It’s what makes the sunset hit like that. It’s what makes love so sweet. Fighting this is fighting reality, and fighting reality is suffering.
I believe the best we can strive to be is “anti-fragile.” Stronger after we break. Reborn after we die. Not unbreakable. Not un-killable. For like Hemingway wrote: “The world breaks everyone and afterward many are strong at the broken places. But those that will not break it kills...”
Integrating what you already know
Just because you might “know” all of this and have read all of the books (cough, me), doesn’t mean it isn’t the hardest thing in the world to look someone in the eyes and say:
“I don’t think I am that thing anymore that you expect of me. I don’t know what I am yet, though. I’m goop. I’m a shattered acorn. I’m nothing that is recognizable to myself. I do not want to hurt you, but I might.”
I have found myself firmly planted inside of a place that only finds comfort in paradox and silly, but true adages like… “Your new life will cost you your old one.” What got you here won’t get you there. To reach the new vine, you have to let go of the old vine. Blah blah blah.
I make no mistake in any of this that it is one of the greatest privileges on planet earth to have arrived at a place where I get to ask myself, “so, what’s next?” But my soul-level problem was that this question did not feel like a privilege to ask. It felt like the most daunting thing in the universe to me.
I wished God would just grant me an answer. He did, but I just didn’t want to hear it. It was simple: just be.
Allowing evolution
Some people in my life make elegant transitions. I am not one of them. I have fought to the death of every version of me and every relationship I have ever held dear. I do not surrender easily. And I have also never been the type of person that can simultaneously step out of a past incarnation of life directly into a future version. I have to throw my backpack over the fence, and let the old me die on the climb before I have any clue why I even threw it over in the first place.
I have learned that evolution of the mind and spirit happens like it might in an entire species. It cannot be forced. It is simply expressed, and suddenly you are like: damn, I am new.
For all of 2024, I felt this sense of: I am only able to recreate the past right now. I am only able to do what I think I am supposed to do, not what I want to do. I do not yet know how to arrive in the future. I do not know what is being asked for my life. I do not have a clear vision of where anything is headed. I do not know what I am meant to build, where I am meant to be, or who I am meant to do any of this with.
In this confusion, I found myself back in old patterns. I forced myself to sit at a computer all day. I read books to find solutions to my predicament. I meditated hard and often. I berated myself with tasks. None of it worked.
But at the same time, something in me had finally shifted. I couldn’t physically go backwards, despite not having a single fucking clue what was calling me forward. I just couldn’t. Something had shifted energetically.
An evolution inside of me had started despite all of my attempts to halt or force it. It started with the destruction of everything I thought I knew about myself and the world.
Life as big wave surfing
I have come now to think of life transitions like the craft of surfing big waves (which I do not do, but am obsessed with for some reason). The surfer’s job is to train their body and mind rigorously. They must understand the ocean, and the way she flows, changes, and alters course quickly. They must have the strength and poise to get up on a board and ride when the time is right. They must have a still mind.
And when they are out in the middle of the ocean, getting ready for a big set, their job is not to paddle around fearfully. This is a waste of energy. Their job is to find the right spot, and pray. And trust in their skills and their training. Trust in the waves of life. And when the strike of inspiration hits that “this is my wave” they must just shut off their brain and paddle with everything they have.
To ground this metaphor in what this lengthy piece of writing is about: we spend so much time paddling against the currents, and wasting energy comparing ourselves to other people getting “better waves.” We put ourselves in the way of death out of fear. We think obsessively about getting all the right gear, and we have fomo about missing the big swell. We are thinking about past waves and future waves, and not looking at the one right in front of us. We often have our attention set on all of the wrong things. And we are so fucking worried that our wave is not coming. That somehow we were forgotten.
But the reality of everything in life is: there is something beyond our control that is guiding all of this. Call it Source. Call it God. Call it the Universe. Call it your own soul. Call it your Daimon. Call it intuition. Call it whatever you are comfortable with. This is the hand that has been guiding you your entire life.
It has selected your waves for you already, and it will let you know when it has one for you. You cannot miss your wave. You cannot mess up your destiny.
But you must let go of the past long enough to get present, cultivate deep belief in yourself and this force now, and paddle your heart out when your wave comes.
Do this over and over, and that’s a damn good life. It’s a true life. It’s a life that integrates death, and celebrates the sheer magic of being alive.
—
Last year, I spent so much time out on the metaphorical water paddling around looking for my wave. I wasted so much time and energy because I wasn’t just willing to sit there. I caused more destruction that was needed — for myself and others.
But now? I’m not yet sure I know when my next wave arrive, or how it’ll look. I can see a few out on the horizon that might be for me, and I am set in my position. But I know this: my mind is clear, I am located in the present, I feel confident in my training, and I’ve got my trust in whatever force put me here.
I’m not in a rush. I’ll sit here and wait for my wave as long as it takes.
If it never comes, sweet. I get wrecked, sweet. If I get the best barrel of my life, sweet. For the first time in a long time, I can say: I’m not panicked. I’m not trying to control the ocean or force an outcome. I know Life will bring me exactly what I need.