From burnout to breakthrough
My journey of experiencing rock-bottom stress and depression, only to rediscover my heart, my light, and my purpose.
It’s December 21, 2022. Winter solstice arrives at the perfect time as I prepare to close down business operations for the rest of the year. I welcome the opportunity to slow down and disconnect from another busy year that felt more fraught and frenetic than years past.
I set my out-of-office. I’d be away for 12 days, not due to return until Tuesday, January 3rd. I’ve similarly taken this time off the past 13 years of running my company. I always welcomed it as a moment for quiet reflection on all I’d received and gratitude for what was to come. This time around though, I noticed those opportunistic feelings gave way to a subtle sense of disquiet — a sinking suspicion that the renewed enthusiasm I typically experience at the start of a new year would escape me in 2023.
I had no evidence to feel this way. 2022 brought with it much to celebrate. A growing team, renowned clients I was proud to be working with, refined offerings that my market valued, and reliable revenue to invest back in the business. And the year before was our best since launching in 2010.
So I chalked up this foreboding dash of discomfort to my all-to-familiar habit of focusing on the negative. As it turns out, I only wish it had been another case of overanalysis. Upon my return that first week of January, I’d enter into one of the darkest stretches of my personal and professional life.
This story is about that experience. Of hitting rock bottom, overcome with self-detachment, depression, and burnout. But instead of remaining there or retreating through the same dark tunnels that took me down, as I had done so many years past, this time I discovered a commitment to surrender and emerge transformed.
It’s my story about rediscovering myself and my bigger purpose. It’s my story, but it’s yours too. Because it’s the story of being human. Of the struggles we all face but only the bravest lean into in search of a life worth living.
The dark way down
It’s now Tuesday morning, January 3rd. I walk into my home office for the first time in over a week. Until that moment, I didn’t realize I had not only been avoiding my return to work but also physically residing within my workspace. Everything about it felt like a self-designed prison.
My first act, which had become a well-worn habit, was to scan my inbox hoping to hear from a prospective client about working together. Nothing helped elevate my dopamine and endorphin levels like the closing of a new business deal. I hunted through several dozen spam messages, cold solicitations for crap I didn’t need, and the typical flurry of vendor invoices. Finally, my eyes landed on a familiar name — someone I’d been communicating with throughout November and December about a major opportunity we were sure to win. I clicked open the email. “Thank you so much for the time you took to create your proposal…” My heart sank. I knew all too well where this was heading.
No matter, I thought. I had plenty of experience of losing seemingly certain business opportunities. To assuage my bruised ego, I darted off to LinkedIn to check my messages, review new connections, and evaluate my recent post’s reactions — intending to surface my next opportunity. But it was quieter than I’d hoped. Fewer connections and messages, and a marked drop in engagement of my content. Something was off.
This pattern would repeat for the rest of January. One after another, each of the opportunities I had worked hard to bring to the table fell off. The companies I planned to work with throughout ’23 were hit by the market downturn, racked with budget freezes and layoffs. “Check back around Q4 to discuss opportunities for ‘24.” For a small company with cash reserves to last about one quarter, that was a death knell… unless I could drum up some new business in short order.
Fear steadily developed into full-blown panic. I had been on this rollercoaster ride before. Since opening our doors, we’d perpetually chased opportunities to survive, let alone grow the business. Operating from a scarcity mindset had become my default. Constant worry, stress, and anxiety were my steady state.
And so I knew to divert all of my energy into business development — the one job I had to do but rarely enjoyed. I messaged hundreds on LinkedIn and emailed countless others. As my lower and lower-vibration energy grew, the reception of my outreach dimmed. I went from positive, warm, and relational to negative, desperate, and transactional. The nos started to pile up.
Suspecting the worst, I stopped paying myself in late January to ensure I had the runway to keep my small team employed. As a preview of what’s to come, I’m writing this post in June and have yet to resume paying myself.
Then in March, something amazing happened that also sent me spiraling harder and faster than I could have ever seen coming. My incessant sales hustle seemed to momentarily pay off — a first-degree connection introduced me to their executive leader who was building a Product organization within a well-known enterprise. Within hours, we were scheduled to meet.
From the get-go, our conversations flowed. He had problems I knew I could solve, and my offers landed well with his hopes and expectations. A couple of days later we were meeting to review a proposal that, if awarded, would keep us busy for the next 12 months. That sense of steady, reliable revenue for that stretch of time was a goal I’d yet to accomplish in my 13 years of business.
A few days afterward, my son Jason and I headed to his annual soccer tournament in Richmond, Virginia. Stopping for gas, I checked my phone — another fear-based habit that had come to run my life as of late. A text from the executive leader: “Can you chat for a few minutes?”
First thought: He’s gonna tell you they went with another vendor.
I frantically wrote him back, “Sure can! Call you in five?” “Perfect,” he replied. I filled my car’s gas tank, breathed deeply, and hit the call button. He answered and went right into it, “Thanks for making time, Jay. We’re going to go with you guys.” My eyes watered, and my heart leaped out of my chest.
I pumped my fist and high-fived an unsuspecting Jason, who took special notice of my teary eyes. I barely remember the rest of that conversation. A wave of relief washed over me. I pulled over and texted my partner, Laura. “We did it, hunnie!” Next, my parents, who were well aware of the challenges my company had been facing. Finally, Taylor, to let her know that everything would be OK.
But to my surprise, after 15 minutes of celebrating, a gripping numbness hit me. Then that familiar wave of dread came. But why? This was a HUGE win for me, my team, and the company. Fortunately and unfortunately, I had the next five hours of mindless driving to analyze where these thoughts and feelings were coming from. Of course, I already knew. They were the same feelings that came up after nearly every contract I had won.
The hard truth, which I had done a phenomenal job of suppressing for nearly 13 years, was that I never loved my work. On most days, I loathed it. I started my company because I was sick of working for others. There was no grand vision. There were no clear problems I was passionate about solving. There was no plan or business model. And there were certainly no customers lined up waiting to work with me. Just an itch to create something of my own.
Sure, there have been many days I’m proud of the brand I’ve built. So many loving people have thanked me for my work — for inspiring them. What a blessing. But in the end, what I’ve always known in my heart is that the business I built is not the work I’m meant to do. And so all that praise and recognition from the outside, which should have felt like a warm blanket, grew into a tidal wave of guilt and shame. So many others would kill to be in the position I was in. And therein is where I and countless other entrepreneurs see their companies as an inescapable death march — trapped by the allure of success but ultimately doomed to suffer and perish.
Worse, we put ourselves out there to try and win business we ultimately don’t want to do. Then add the countless rejections, the constant battle to stand out, and the regret of taking on projects purely for the paycheck. Parts of us get whittled away until we no longer recognize ourselves, eventually reaching complete detachment from our souls.
That’s a glimpse into my professional life for the past decade-plus — chasing opportunities that put food on the table but fail to align with what’s in my heart. I’ve run toward untold mile markers labeled Success. Each time I round the bend, the finish line stretches just out of reach. The constant pressure I’ve put on myself to win keeps me endlessly hunting a victory I’ve always wanted but never seem fit to claim.
But I shoved on…
As I had done every other year in business, I put my head down and continued the grind. That big contract I had won and briefly celebrated would take months to get paid on, so there was a lot more work to do to keep us afloat.
Over the coming weeks and months, I spiraled… harder and further than ever before. The grief and loneliness I’d felt while grappling with my divorce a few years earlier felt like a walk in the park compared to the low places I found myself in.
Emotional outbursts became prevalent. I was miserable to be around. Short-tempered one second, racked with apologetic guilt the next. On multiple occasions, I’d have to fight back tears simply from attempting to read and respond to work-related emails. Everything triggered me. The worst, by far, was spending time on LinkedIn. I resented everyone and everything there, especially the algorithm, which I decided was, single-handedly, out to ruin me and my business.
Then, acute physical conditions started appearing. First, months of brain fog made it nearly impossible to focus. At its worst, it became difficult to see and keep my balance. I chalked it up to allergies and started a daily dose of Claritin. Then issues with my prostate had me making five to ten bathroom trips per night. When surgery didn’t resolve it, my already shitty sleep morphed into full-blown sleep deprivation, worsening the brain fog. Finally, I landed in the hospital after experiencing chest pains and a throbbing in my neck and head that felt like the worst flu of my life. It’s still unclear what happened, but after meeting with five specialists, it was determined that air had escaped from my lungs and into my chest, neck, and shoulders. The likely culprit? Excessive strain.
I had heard others talk about burnout. I always figured it was just a slightly heftier dose of stress.
Shit, in my 20s, while working 100-hour weeks at Accenture, I’d often pat myself on the back for bull-rushing burnout with sheer grit and mental toughness. Little did I know how debilitating true burnout is — physically, emotionally, spiritually. But as it turns out, it was exactly the medicine I needed.
See, if that wall I hit had been softer or only held its ground for a couple of weeks, I would have dusted myself off and jumped back in the game, as I always had. But this wall hit me, ran me over, and pushed me deep into the Earth. I couldn’t get up. I would have to dig my way out until I was in an entirely new place.
One night, I lay on the couch, searching for something inspirational to watch and lift me up, even if momentarily. I had declined to go to a local concert with Laura. As had become expected, I wasn’t feeling it and refused to be a drag on her night. It was another night of sending her out alone, devoid of the love and partnership I once brought to our relationship.
After cycling through several spirituality-themed Netflix documentaries for a while, a thought popped up that I’d go away on a solo trip. I would rest, recharge, and, who knows, maybe even rediscover myself. After texting with some of my more well-grounded friends, I settled on a week-long vacation in Medellín, Colombia. After a few hours of research, I had the perfect hotel and itinerary mapped out.
As I was about to purchase my hotel and move on to airline reservations, I remembered my friend, Mona. Something told me to seek her advice. I shared a text-friendly version of my situation. I remember telling her I was at a 9 out of 10 with burnout. Because only the weakest and most delusional would allow themselves to reach a 10 out of 10... or so I shamed myself some more.
I could see that she was typing. Then she stopped. Shit, I thought, I spooked her with that 9 out of 10 burnout crap. And then, a link appeared: 1heart.com. She followed with, “It sounds like you need more of a wrecking ball.” She nailed it. While it may sound dramatic, a wrecking ball was exactly what I needed. After all, it was the only thing that had a chance of removing this unbearable wall from me.
What I didn’t know then was in that moment of opening the link from Mona, my journey of deep healing had begun. And I’m not talking about getting out from under a few months of slumping revenue, but healing a lifetime of disregarding myself and neglecting my heart.
What follows next is nothing short of my own personal miracle — the start of discovering the man I’m meant to be. The man I want to spend the rest of my days being. For myself, my sons, Laura, my family, and the world around me. You, too.
If you’ve made it this far and you need it, I hope the rest of my story gives you hope — no matter how dark things may feel.
We are our own medicine
If you happened to click on that 1heart link above and skimmed the program, I wonder if the same thing happened for you that did for me…
When Mona texted me that link and I opened it, I traveled a series of feelings and emotions. Initially, there was curiosity. As I got deeper into the work, program, and success stories of others, curiosity turned to hope. I sensed a way out.
Next, I read about their use of ayahuasca — a sacred plant medicine used by indigenous tribes for thousands of years to help disrupt unhelpful conscious thoughts and open up space for oneness and more heart-centered, intentional living. I read about the group I’d be a part of and the intentional work I’d be doing along the 8-week program. A tinge of resistance crept in, knowing that surrender, vulnerability, and discomfort would be part of the work.
As I continued reading and researching, my default mode network went to work. The more excited and hopeful I became, the more my mind enacted its self-preservation mode, spinning up stories to prevent me from acting:
I’m not cut out for this program. And I’m clearly not successful enough like these other leaders. So I won’t even be accepted. And if I do somehow sneak through, it won’t work for me.
Ah, the stories we tell ourselves. The endless chatter from our inner critic. Though, somehow, I was able to override my mind long enough to submit an application. Fuck it, I thought, what’s the harm in applying?
To my surprise, the next morning I had an email from Camila, the program coordinator. They had reviewed my application and wanted to schedule me for an interview with their leadership team. Again, more stories littered my mind about them using these interviews to discover the fraud I am.
Leading up to my interview, I Googled the person I’d be meeting with, Barry Stamos
— co-founder of 1heart and a serial entrepreneur with multiple exits in the billions. Why would someone of his success allow a busted, burned-out entrepreneur into his community? I thought, This will be quick. He’ll ask me some questions and recommend I try again when I’m further along. He’ll probably even become aggravated with his team for scheduling my interview.
It was the exact opposite. Barry was warm and patient. He led me through some grounding breathwork to open our conversation. Then he asked sincere questions and probed further, out of pure interest of who I am and how I got here. As we wrapped up, he shared more about the program and said, “I think you’d be a phenomenal fit for the program, Jay. There are still others applying, and though it’s not entirely up to me, I’m going to recommend you to the larger team.”
Of course, I resigned to believe he said that to everyone, and within a few days I’d be gently dismissed. Instead, two days later I received an official offer to join the next 1heart journey. Just like when I received the verbal commitment from that enterprise leader about working together, my heart fluttered. Except this time, the fluttering didn’t turn to numbness or dread. In fact, it hasn’t stopped fluttering and has only grown stronger.
I read the acceptance email again. Then once more, making sure I didn’t misread something. I texted Mona, “Holy shit, I’m in. This is happening!” “Yay!!” she replied.
No doubt, the initial draw to a program like this is the psychotropic plant medicine in an exotic destination. For 1heart, that culminates in an in-person, week-long retreat with three ayahuasca ceremonies nestled in the beautiful, lush jungle of the Chirripo Mountains of Costa Rica.
Especially for us Westerners, we convince ourselves that these one-off experiences are the antidotes that can provide us a quick fix. But I’ve come to learn two important, holistic truths along the way:
One, there are dozens of tools and modalities we can leverage to support our transformation — from meditation, journaling, breathwork, and exercise, to ayahuasca, psilocybin, and other sacred plants. In the end, the real medicine has always been and always will be ourselves.
Two, the moment we say yes to experiences like this, the universe begins working to line things up for us. It’s not the final outcome that leaves us transformed but the journey we travel through to get there.
So while the experience in Costa Rica was nothing short of life-changing, there have also been myriad other synchronicities that appeared, heartfelt conversations with my new 1heart family, prompts I journaled on and set intentions toward, books I read (included below), and the work others have put in before me (also below) that have supported my still-in-progress transformation.
Lighting the way back up and out
As I prepared for my trip to Costa Rica, I spent a good amount of time meditating on and journaling about my intention entering into this work. The more heart-centered clarity and intention you bring, the deeper your insights and breakthroughs will be.
My intention was to discover myself — not rediscover. See, after 30 years of numbing myself with work, drugs, and alcohol; keeping loved ones at arm’s distance; and doing what I thought the world expected of me, I had no idea who I was. If I left Costa Rica with a glimpse into my true nature, it would be a massive victory. Little did I know, that was just a taste of what I’d walk away with.
I sat with and journaled on my biggest fears:
I’m going to run out of money
I’ll never be successful
I’m failing my sons who will eventually push me away
I’ll end up alone
As well as my limiting beliefs:
I’m too old to change… it’s too late
I’m too passive… I never fight for what I want
I can’t make up my mind… I’m too indecisive
I’m just not cut out for hard things… I should give up trying to be an entrepreneur
I’m an imposter… my life and my work are bullshit
It’s amazing the therapy we receive by writing these down and consciously choosing to let them go. Releasing them was exactly the right precursor leading up to our three ayahuasca ceremonies.
During the ceremonies, there were moments of panic and pain — physically and emotionally. However, if you went into the ceremony with complete surrender, on the other side was always love, peace, and bliss. And to be clear, I’m not talking about some high you get from doing a bunch of drugs. This was different — an altered state that’s difficult (not impossible) to access during our busy days of email, meetings, and incessant small talk. It was freedom from all of it.
For me, it was a chance to allow my subconscious to come forward. Sometimes it brought up repressed and overwhelming grief from the past. Other times it produced waves of terror of an unsure future. But I learned to breathe, face it, let it in, and let it go. Because right around the corner was joy and play. That showed up as belly laughs, uncontrollable sobbing, and sometimes both at once.
I felt a softening in my heart. I was surrounded by loved ones. I saw my sons. I knew their hopes and fears. I saw the loving Dad I am and the more patient Dad I’ll be. I found my Mom and Dad, across time — as children, young adults, and the people they are today. I saw Laura — the pain she hides, the hurt she feels, and the love she continues pouring into the world. But, I didn’t see them as separate individuals from me. They were me. We were all one. It was beautiful. My heart stretched wide open and brought us all together.
And now, here’s what brought me to my knees… for as long as I can remember, I’ve been a man ruled by science and logic. Someone who decided that religion was for the weak and gullible. But there I sat, at the edge of my makeshift bed, purge bucket between my knees, surrounded by 40 other leaders, experiencing the presence of God. Even typing those words (for now) still feels foreign to me. And yet, I felt it. With tears streaming down my face, I sat in the light and love of God.
I knew, or maybe I remembered, what it meant to live. All of the books and talks I’d consumed about being in the present moment now resonated throughout my body. I was humbly, magically alive. I was deeply connected to my life and the Earth around me. I embodied the life I would now live. I saw the man I am to be.
At that moment, my intention became clear. I would become a light in the world around me. I know it will be hard. God, will it be hard. My friends and family will assume that, of all people, I’ve clearly lost my shit. And that’s exactly why it has to be me. Because if a closed-off, overly analytical guy like me can get vulnerable, open his heart, and share it with others — especially the ones most afraid to do the work — then anyone can be inspired to do the same. Not for fame or even a ‘thank you.’ Purely out of love.
Keeping an open heart, in life and work
Throughout the week in Costa Rica, I noticed my tendency to want to seclude myself from the group. I mean, two weeks prior these 40 people were legit strangers. Now everyone is labeling us family?!
When I first arrived, everyone, especially the staff and returning alumni, referred to one another as brother and sister. Oh c’mon, with eyes rolled back… My skeptical, judgmental mind was on full throttle. But something in me told me to go toward the group. To practice opening. To demonstrate vulnerability. Neither of which are easy for me — the opposite. But as I continued to see myself open-hearted in ceremony, I understood that seclusion and labeling myself ‘introverted’ were just choices. I could choose differently. I could show up. I could do the work. And by the end of the week, as strange or as rushed as it may sound, these 40 people were my family. These women are now my sisters. The men, my brothers.
Living any other way, with armor on and walls up, isn’t living after all. It’s just existing. To live is to love yourself and the world around you. And so, as new and challenging as that mindset still feels to me today, I know that with time and practice it will become who I am and who I attract into my life.
As for my work, going into this program, I was ready to shut down my company-turned-prison. As grueling as it would be, after 13 tireless years, I had prepared to say goodbye — hopefully from a place of knowing that it was the right thing to do. Instead, what became clear is that I can and should apply my expertise as a product strategist and entrepreneur to companies with missions that align with my heart. And so I’ve decided my company will focus its services on organizations dedicated to leaving our planet in a better place than today. If you’re working in ClimateTech, GreenTech, or AgTech, let’s talk.
Also, in learning to say “yes” to my heart, new and exciting opportunities have started appearing that I’m considering. That’s how the universe works, right? When we get out of the way and out of our heads long enough, we allow its perfection to open our hearts and serve us what we’ve been looking for all along.
My journey is your journey
So this is me now. Open-minded and heart-centered, with a ton of work to keep it going and integrate this new awareness into embodiment. I’m going to slip. I’m also going to get back up. Because that’s life — beautifully imperfect, so long as we keep showing up.
And so, I hope my commitment to be a light awakens that same light in you. Because no matter how small and insignificant you tell yourself you are, you are beautiful, a light for someone else’s shadows, and we’re all waiting for you to shine.
I’m here for you. I’m there with you. I love you. ❤️
My commitment to support you
If you’re feeling lost, stuck, or burned out… If you have questions. If you just want someone to hear you, please reach out. I’d be honored to be there for you, like so many others have been for me. Reply to this email or reach me at jay@newhaircut.com 🙏🏼
And if you think this post will help someone else in your life, please consider sharing it.
Resources that supported my journey
There are more — I’ll keep adding to this list as I remember them
Thank you
To Brandon, Barry, and Tom for creating the 1heart container
To the angels of 1heart: Salman, Mike, Dani, Simone, Miguel, Andrew, Christian, Camila & Pablo.
To Jesus, Gracia Maria, Delfina, and Kuauhtli for their indescribable magic.
To David for Kinkara.
To my elevation group for seeing me.
To my entire 1heart family, so much love J18.
To Mona for bringing this experience into my life.
To God for not giving up on me.
And to my family and friends, my lifelong teachers.
Thank you for being the light Jay! I really admire you being this vulnerable and explicitly human. Your journey is my journey.