On Dying (before I die)
Welcome Entrepreneurs, I'm so glad you're here. And special welcome to those new subscribers who have joined us since last issue's deep dive into changing mental patterns.
Today's issue, about "dying before you die" (as is said in so many wisdom traditions), is a longer one (about 10min read), and is one of those I hesitated before publishing, fearing it was too intimate for public consumption. Maybe it is. But so many good things have happened in my life since I started sharing my journey, even (especially) the uncomfortable parts. I would be a fool to turn back now.
I made a commitment to myself to live fully expressed, damn the torpedoes. And so I will.
May some good come to you in the reading.
On Dying (before I die)
I had to die three times before I finally got the hang of it.
The first time I was 17. I was a hotshot kid, with visions of NBA superstardom. But I was short, with only above-average athleticism, and despite being the best player in town, I didn’t listen well. Fed up with my ego, my coach benched me to send a message. Instead of listening, I quit the team. The kid who had been a Future NBA Player was all of a sudden nothing much.
In response to my first death, I fell into a deep depression. If I wasn’t a future basketball star, then I was nothing. I experimented with drugs, drinking. I was determined to break through to the other side or die trying. Maybe those were the same thing. I lived a kind of half-life, the toes of one foot always edging toward the exit, until I was 21 when I was laying on a stiff cot in a jail cell two days after my second DUI. I didn’t recognize myself anymore. The pit of anger in my stomach was the only thing anchoring me to the world, making the happy kid I’d once been feel so distant. The cycles of chemically induced ups and downs, by turns overwhelming and numbing myself. All the pain leading up to that moment was, mercifully, enough, and in jail I died again. Me the Chemical Warrior. The me I didn’t want to recognize.
It took me the better part of a year to dry out. Not long after that, I decided I could still be great. I saw how the world looked at Steve Jobs and Bill Gates, and bit by bit, I began crafting myself again. It took a few years before reality caught up to who I knew I would become, but in time I was the head of a tech startup. Funded, millions of dollars of support from people who believed in me. People who were betting I could become the perfect CEO, I thought. The Steve Jobs of the midwest.
I rode a rocketship, for a while. Up and down and up again, financing after financing, all the way to an M&A strategy that my board wanted to be led by someone more experienced. That hurt, but it wasn’t until I signed the paperwork to hand over the CEO role to my replacement that I died again. The hotshot CEO on his way to taking over the world was suddenly, once again, nobody at all.
Perhaps this one cut deeper. Perhaps I saw the opportunity more clearly in my old age. Perhaps I was simply tired. Whatever the reason, the time Ryan the CEO died was different.
I had an instinct to resurrect him, as I’ve learned is our very human, knee-jerk reaction to death. I would start another company, keep my identity alive, even if that meant I would be on life-support for a while. But something in me knew that jumping back into another company would simply be getting back on the hamster wheel, restarting a cycle that would end in the same place. And if I was honest with myself, I’d been tired of holding it all together as the perfect CEO for a while by that point. Years, maybe.
So, for the first time in my life, I allowed myself to die. The part of myself that I’d cultivated publicly, the me that everyone knew as the hotshot CEO, I decided to let that go. And for the first time, I didn’t immediately recreate another, equally compelling person to be.
The Journey of Transformation Through Death
I can’t yet speak to what happens after you die the big death, but after each little death, there’s a space that opens up that is absolutely terrifying. What I learned during my first three deaths is that everything depends on how you interact with that space.
When Ryan the Future NBA Player and Ryan the Chemical Warrior died, they were replaced by a bottomless pit, a vacuum where an identity once was. That vacuum sucked in the very next suitable replacement identity. The next person I could be that was compelling enough to be admired (my own personal bar for what was a worthy thing to be). The death of Ryan the CEO was followed by that same vacuum, only this time, I just let it be.
"We must let go of the life we have planned, so as to accept the one that is waiting for us.” – Joseph Campbell
I remember telling Laura, “I’ve been running so fast for so long, and I can’t convince myself that what I’m running after matters all that much. So I must be running from something. I don’t want to live my life running away from something. So, I’m going to stop, let it catch up, and see what happens.” Somehow, she understood, or she trusted me. I’m not sure I would have, but for either or both, I’m eternally grateful.
I dove deep into meditation. I stayed at a monastery. I told the Abbot of the monastery my sob story. “I don’t know who I am anymore.” I said. “I need to figure that out.”
He smiled. “We’ll cover that,” he said as if he’d seen one of me a month for years. A couple days later showed me who I was with a clothespin. Who I’d always been, even when I’d thought I was somebody.
After the death of my CEO-ness, my intention had been to become somebody again, but somewhere in the liminal space between I realized that here I was, an ineffable nobody, and still very much alive. More alive than I’d felt in a long time. I’d entered the monastery with a question I was determined to answer. I left with a question I was determined not to.
I was terrified to not know who I was and where I was going, but for the first time I grokked the game. I realized that if I could create an identity for myself, then it was impossible for that identity to actually be me. I couldn’t possibly be the NBA player, or the drug addict, or the CEO, or anything else. I was the thing behind all that. The one doing the creating. Or not.
Orienting to death
Once you die a little death and do it well, it tends to cascade. Once you see through your main identity, the rest of your identities start to look pretty artificial as well. Then comes the slippery slope. On the heels of laying Ryan the CEO to rest, it wasn’t another month before I died again.
It was the fourth quarter, we were down by 10, and I’d just missed a three pointer. My teammates were all former collegiate basketball players, none less than a decade my junior, but my inner critic laid into me. “You’re garbage,” it said. “A has been. If you can’t win this game, they won’t even let you on the team anymore. You’re only on the team now because they pity the old guy.” I heard this in my head, but for the first time I heard it as something distinct from me – simply a thing that had been operating in my brain for some amount of years. I could see how it motivated me to push harder, but at that moment it was as artificial as my CEO-ness, and frankly pretty gross. With two minutes left to go, I decided to ignore the voice and just play for fun.
We lost the game. Unlike any loss before, I felt ok about myself afterward. Thus died Ryan the Competitor.
As I’ve learned happens with little deaths, the next day I panicked. “How will I ever play again,” I wondered, “without that voice? How will I ever win the tough ones if winning isn’t life or death?” But losing wasn’t death, as I could clearly see, and I could no longer convince myself otherwise. I showed up to the next game disoriented but with a lightness and appreciation of the game for its own sake. Here I was, 36, and well past the point at which I shouldn’t be able to hang with these college kids, these whippersnappers.
I scored 36 that game, and we won going away. It was exhilarating. I couldn’t remember having ever felt that free on a court.
I’ve been asked, “don’t you feel less, when you let go of those pieces of yourself that matter so much?”
I’ve found it’s the exact opposite.
Who I thought I was died dozens of times over the next few months. Ryan the Provider. Ryan the Lions Fanatic. Ryan the Social Director. Dead, all three, and more. I mourned each one, intentionally feeling the depth of my grief as each fell away. And after each I felt a little more alive. My emotions cranked up just a bit. The immediacy of sensations. Everything, just more raw and electric. I lost who I thought I was, and with it there was one less layer between the world and me. Not Me the XYZ. Just, and only, me.
Eckhart Tolle said, “Death is a stripping away of all that is not you. The secret to life is to “die before you die” – and find that there is no death.” Richard Rohr pointed out that “the phrase ‘you must die before you die’ is found in most of the world’s religions. If you don’t learn how to die early, you spend the rest of your life avoiding (it).”
That type of gobbledygook had always struck me as profound-sounding nonsense. But from my new vantage point, I thought I finally saw what they were talking about.
Letting Go: A Key To Personal Growth
I had finally discovered myself. After years of digging, underneath all the somebodies I’d been was, at base, an ineffable spirit, part of the greater Spirit who if I intentionally quieted my mind enough would speak through me. Below all my thinking and striving, I unearthed a tiny flame who found its likeness in Martha Graham quotes:
“There is a vitality, a life force, an energy, a quickening that is translated through you into action, and because there is only one of you in all of time, this expression is unique. And if you block it, it will never exist through any other medium and it will be lost. The world will not have it. It is not your business to determine how good it is nor how valuable nor how it compares with other expressions. It is your business to keep it yours clearly and directly, to keep the channel open. You do not even have to believe in yourself or your work. You have to keep yourself open and aware to the urges that motivate you. Keep the channel open.”
After all the mini deaths, I thought I’d found the bottom. I almost congratulated myself for having done so (and therefore risked becoming Ryan the One Who Had Found the Bottom, although I didn’t see that at the time). Until last Thursday, again on the basketball court (the apparent arena of my life), when I planted and sprung forward to get a rebound.
Pop.
The doctor delivered his diagnosis: ruptured Achilles tendon. He answered my question about when I’d be back on the court again with an uninspiring shrug. I got fitted for the walking boot I’m now wearing. As all of this happened, what I realized was that there was still more Me in the way of that flame. More of me to go.
So I write this in mourning. I may never play basketball well again. I almost certainly won’t play it at the level I did a week ago. Last night I cried, feeling the loss of a part of myself. The death of Ryan the Basketball Player. I know the game now, so I didn’t try to fight it. I didn’t try to bargain or deny. I am grateful I had the presence of mind to feel it at every level I could. The person I thought I was deserved that much.
And today – gimpy, tired, more than a little emotionally raw – I am also lighter. More free. Looking forward to two-to-three months from now when I can step back on the court and play the sport I love, not with the baggage of being a Basketball Player, but as a human being who will only get so many more 90-foot sprints, and determined to enjoy every dribble, pass, and shot.
With every death I become less of a somebody. And with every death I become more me. I tell myself I’ll be a pro at this dying thing by the time I’m old enough to do it completely.
Things I read this week
One: Wisdom for the end of the year (The Imperfectionist)
I’m cheating a bit because I read this at the end of the year. But the wisdom in this little nugget of a newsletter is timeless. They all resonate, but the one that cut deepest for me was “On the cruelty of a life spent trying to save time.”
LINK >>
Two: 750words.com
As a borderline-religious devotee of Morning Pages -- Julia Cameron's invitation to journal 3 pages, longhand, each morning as a means to a) dump all the crap you're starting the day with, and b) get your creative juices flowing -- this is a pretty cool app.
Three: Smart Decisions (Farnham Street)
Farnham Street here makes the assumption that there are better and worse ways to make decisions, and that doing so well requires practice and intentionality with regard to the decision making process itself (not just ruminating on individual decisions). What an obvious stance, and yet it’ll blow right by most of us because we’re still looking through our decision making process instead of at it.
LINK >>
Four: The best managers don't fix, they coach (First Round)
One of the byproducts of coaching CEOs is a lot of CEOs asking you how to bring coaching to their organizations, and how to be a better coach in the manager role. A friend of mine and fellow coach wrote up a manifesto of sorts on just that.
LINK >>
Five: Focus on this one thing for a happier, more fulfilling life (BetterHumans via Harvard)
Science says you are as happy as your relationships. Hard stop. You will have to answer for yourself why you spend meaningful time on anything else.
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