On Failure and Forgiving Yourself
Thoughts on laying a determined dream to rest, and what comes next
“Throw off displeasure at your nature; forgive your own individuality. You have in yourself a ladder with a hundred steps to mount to knowledge.” - Frieddy Nietzsche
How the absolute hell am I here again?
I’m sitting on the side of a busy street on a freezing cold night in Seattle, Washington. It’s dark and pouring rain in the middle of December, yet I’m just wearing a t-shirt, fending off the chill with a solid buzz.
This was supposed to be a pleasant trip with my brother and dad to see a Seahawks game. I wasn’t supposed to make it about me. I was supposed to have grown out of these desperate and manic downward spirals. I had learned the healthy systems to cope with my departure from the business I spent six painstaking years building. I was a more evolved, educated, and reasonable person than I was at twenty-three. I had written articles speaking to founder mental health, done the work in therapy, and shared tips for resilience on podcasts. I had even written a few chapters of a book titled ‘From Suicide to Success’…
Yet there I was - back in the same dark place, fighting tooth-and-nail with a terrifying desire to walk out into the noisy street and escape the crushing weight of knowing that I had failed, again.
Apologies for the lack of a trigger warning there, folks. I’ve been told I have a penchant for the dramatic, so what better way to begin a brand new essay and newsletter series than an old fashion dark-spiral moment?
Life has changed a great deal in the short months since that bitter Seattle night - and I’m looking forward to sharing updates with all of my dear friends and comrades that have a moment to spare. But first, and here in my first public writing since the events that led up to that evening, welcome to Daydreamer Ventures. While all of my posts won’t begin with such a difficult retelling, I wanted to start with the worst day of last year to set a standard for these essays: one of truth-telling and raw dialogue, in the hopes of cutting through the bs that we’re all constantly drowning in to reach some kind of a genuine conversation.
While I absolutely plan to focus my time and attention on sharing every bit of helpful inspiration and practical advice that I can wring out and unto a page, do not expect a cut-and-dry startup or business productivity newsletter here. There are plenty of AI talk-tracks and repurposed content factories for that. This is straight learning-earned-from-mistakes-made, written in flow. We’re going to fly with no auto-pilot, as we navigate these murky skies together without Father Altman and Cousin Claude’s blessings, so please excuse the occasional typo or run-on sentence. This first post, especially, may feel as though it is wandering off into some strange corners - stick with me, if you can.
As a format, expect each weekly Daydreamer post to discuss a specific topic, usually in the realms of startup, marketing or philosophy, with as much helpful and honest opinion as I can muster via my learnings from a lifetime building and across my three active businesses, with as much input as I can rally from both the giants who lived before us, and the legends who live among us - whoever I can get on the phone.
For this first essay, I’d like to start by telling you a bit about me - so that you have context on just who is so casually reciting insights around the following topic that is very dear to me: navigating failure and finding a way to forgive yourself, in the worst of times. Make it to the end and I would venture to guess that one little tidbit will stick with you for the next time you’re forced into that terrible position of staring down the barrel of a devastating failure, and struggling to find a way to re-establish your sense of self, much less your confidence, in the aftermath. If you’re there, or have been there recently - whoever you are, remember that you are far from alone, and things get better.
From the bottom of my heart, thank you for taking the time out of your busy day to read this, and share it/subscribe if you found it interesting.
From as early as I can possibly remember, I just wanted to build. The first memories that I have are of three-year old Zack sitting on the carpeted living room floor in our family’s Boise house in 1994, asking the vacuum repairman how each piece of the vacuum worked, only to take it completely apart when he stood up to use the bathroom. I always wanted to help, to solve problems - though as with the vacuum, I just as often made things far more complicated. The ADHD diagnosis should have been clear back then, as I wandered off to my next mental adventure with pieces strewn asunder across the entire room.
For those who are new to my story, my siblings and I lived a rather unique childhood. After a few early years in Boise, my parents moved us to Costa Rica, and then to a tiny village in the middle of the Amazon Rainforest called Shell Mera, Ecuador.
While my father worked as a medical doctor in the small 30-bed hospital there, and my mother did everything from teaching classes for the indigenous tribes to finding ways to throw extravagant themed birthday parties for three American kids in the jungle, I curiously poked and prodded my way around. I spent much of my time up in our thatched-roof treehouse, swinging in my hammock and scheming new ways to fix whatever an eight-year old sees as society’s largest issues.
I started little businesses for everything I could think up: shoe-shining for the adults while my dad hosted Bible study, car-washing for the soldiers coming back from drives into the muddy jungle, movie rental from our illustrious forty film collection for the other families in the village. In short, I was definitely a bit of a weird kid.
Despite my firm belief that anyone can learn to be an entrepreneur, I also believe there are those of us who were born into the strange clan of daydreamers - and whether it’s neurodivergence or something else entirely, we have been placed here on this mortal plane to spend our days wandering and pondering; and the young dreamers must be celebrated and protected in any way possible.
Research from the Kauffman Foundation found that nearly half of entrepreneurs score high on ADHD indices - not as a disorder, but as a cognitive difference that enables pattern recognition and creative problem-solving. Dr. Scott Barry Kaufman's work on 'mind-wandering' shows that the brain's default mode network - active during daydreaming - is essential for creative insight and long-term planning.
The ideators are our most vital resource, if we hope to improve the state of things: the student staring out of the classroom window imagining the clouds as Studio Ghibli airships or the intern sitting uncomfortably in a poor-fitting suit, fantasizing about their innovative fashion line while fetching coffee.
I also believe that, despite our adulation of a few well-branded billionaires, our society doesn’t do a very good job encouraging this vital sect. Instead we mold and prescribe and systematize, attempting to ensure that dreamers spend their days nodding along to the beat of the drum - we used to dream bigger, and more freely, in this country. We fill every open space with a notification or a feed, and the thought of walking in silence or laying in bed without a screen terrifies us.
The motivational YouTube videos and hustle-influencers are simply the sophisticated and algorithmic systems used to keep the next generation of daydreamers glued to their phones instead of out thinking and building and writing and coding and testing and creating. They make better employees that way. We have to fight for our natural right to just sit and daydream, of this I am absolutely convinced.
"Imagination is more important than knowledge. For knowledge is limited to all we now know and understand, while imagination embraces the entire world."
- Albert Einstein
Luckily for me, Emperor Zuck wouldn’t start coding for years, Tom wasn’t everyone’s friend just yet - and down in the jungles of Ecuador there was plenty of space for a weird kid to simply be. I had the space to dream.
Ironically, things really clicked into gear the day a very special package arrived from the United States.
I have a clear memory of the first time I opened the screen of that Gateway Solo laptop and seeing that beautiful cow-print cube logo, thinking “this has to be the coolest thing that humans have done so far.”
From that point forward, connecting people through and creating for the digital screen would always be a part of my life. Upon our return to the United States I started my first official small business, Neighborhood Knowledge, that sought to connect neighbors who had a need for, or could provide, services like lawn-mowing and raking leaves. As someone who spent many of his days alone, as an American kid in Ecuador, or a non-LDS teenager in Utah, this theme of human connection through technology would follow me for the rest of my career.
After studying philosophy at USC, I dove into my next project: connecting up-and-coming painters, who were struggling to pay the rent despite being incredibly talented, with city-dwelling young professionals who all hung the same sad IKEA print on their apartment walls; this was ArtLifted. The company started off strong, and we donated thousands to an amazing non-profit organization called PS ARTS to fund elementary school art classes through the process. However the concept was difficult to scale, and after a couple of years, and thousands of hours of effort, it was time to shut things down.
It was here, through the challenges of this company conclusion, that I first came in contact with the potential for entrepreneurship to have devastating effects on a person’s sense of self. And let me tell you, for an oldest child who grew up with a crippling fear of letting people down, it was a doozy.
As any founder knows, starting a business requires an unusual amount of effort. That level of effort is typically only possible through a complete fusion of your personality with the company’s - to a degree that naturally makes W2 employees deeply uncomfortable. We wake up and instantly start thinking of ways to fix our lead funnel. The shower is a space for tweaking product, and evenings when others are watching the newest show are required to create content and network. Once you start a business, your ‘not-at-work’ persona entirely dissolves into an engine constantly committed to improving your slim chances at startup success. It is a natural process, and one that many of the best entrepreneurs not only engage in, but regularly teach and preach to those that follow them.
Psychologists call this 'identity fusion' - when the boundary between self and group (or in this case, your company) becomes so permeable that threats to the business are processed by the brain as threats to your own survival. Research from the University of Oxford shows that when identity fusion occurs, people exhibit extreme pro-group behavior and self-sacrifice - it's why founders will work themselves into the ground.
The flipside of that dissolution of self into a servant of the business is that when the business fails, what is left? If everyone knows me as the art-company guy, who am I when the art is gone? This isn’t simply a knock to your ego in the modern sense of the word, but a real and serious challenge to your ego in the ancient Greek fashion: the core of who ‘I’ am. And that is just f*cking scary, no matter who you are.
The reactions to this experience vary, but one thing that is for certain - we don’t speak enough about it. We don’t build resources and share content to ensure that people know that they aren’t alone, even when they feel unbelievably, suffocatingly trapped.
Research shows entrepreneurs are twice as likely to report a lifetime history of depression, and three times more likely to experience substance abuse and addiction. They are also, as has unfortunately been the case twice in my lifetime, twice as likely to attempt suicide.
Dr. Michael Freeman, one of the only well-established physicians to conduct research in this area, found that a startling 72% of entrepreneurs report having mental health concerns - and that the most reliable determinant of this dark spiral was the feeling of being trapped. The neuroscience here is clear: when the brain perceives no escape route, it triggers the same neural pathways as physical entrapment. The amygdala hijacks executive function, flooding the system with stress hormones that impair decision-making and future-thinking - exactly what you need most in those moments.
So, our dreamers are struggling - and the main driver of that depression and desperation is the feeling of being trapped - what can we do? We can shed light on these experiences, share the real truths from our own lives, and ensure people know that no matter how fast the walls seem to be closing in, there is always light on the horizon if you can push through the pitch-black. I’ve long desired to start this community, Daydreamer Ventures, for exactly that reason.
"When we are no longer able to change a situation, we are challenged to change ourselves." - Viktor Frankl
In the months following the erasure of ArtLifted, as I sought out the authentic self hiding underneath my self-imposed identity, I worked to discover systems that would form the foundation of the strong-willed and even-keeled mind I wished to develop: Stoicism, meditation, Adlerian psychology, regular reading and regular exercise. I worked hard to be more intentional in my friendships, honest with my partner, and to maintain a better separation between business and my conscious self. I looked to build an operating system for life, as armor to battle the demons of doubt and disappointment that constantly test the walls and the windows, hungry for a chance to come inside - and for many years, it seemed to have worked.
The following years brought highs and lows aplenty as I worked to build agencies, consumer brands, and software products - now even in the worst of times, I could fall back on the frameworks that I had built. I had designed a safety net so that even the greatest slip wouldn’t be fatal.
These were impactful and special years. I moved to New York, met my wife, and we created a life for ourselves. I was blessed to work with incredible teammates, internationally-recognized brands as clients, and my best friend - my little brother. I spoke in front of hundreds at SXSW and the Marketing AI Summit, on live television as a marketing and entrepreneurship expert, and as a guest on more than twenty podcasts. Our team won Inc. Best Workplaces as recognition of the unanimous agreement that we had created a fantastic place to work. The top venture funds in San Francisco were reaching out every week. I felt that I was waking up every day and fulfilling my purpose.
But under the surface, there was trouble brewing. I stopped exercising, and then I stopped reading. I found myself getting carried away drinking too often, feeling constantly surrounded by it amongst the Brooklyn community I had built. I was becoming overly obsessed with the work - I lost any separation between my startup and my own persona. I worked 100-hour weeks, so who has time to meditate? Who has time to be creative? The safety net was beginning to fray and falter, but I wasn’t paying attention.
And then things fell apart, and the net was nowhere to be found.
This is the first time I’m writing in public since my departure from the AI business that I spent six years building.
This is not the forum for details, but in short: during a difficult personal year, things did not go as planned. The outcome wasn’t what anyone hoped for - not for the business, not for the team, not for those who believed in what we were building.
I stepped away from the company that I had spent more than half a decade building, walking away from the business that had consumed nearly a third of my working life, and from a team that I genuinely cared deeply about. As an aside: the business is still growing and doing well under new leadership.
All of this is not easy to write. It has not been an easy experience. In comparison to the failure I took so hard at twenty-three, here the stakes felt far higher. The expectations were greater. The weight of disappointing people I respect was crushing. I blinked, and I was eleven years older, and right back in the same dark place, without the healthy foundations I had used to climb out last time.
I had lost friends and walked away from what felt like my dream role - which paled in comparison to the heaviness of losing a great deal of respect for myself. My fragile ego that was constructed out of press mentions and employee adoration came crashing down like the house of cards it really was. And before I knew it, I was standing on a curb in the freezing rain in Seattle.
If you’ve found yourself in this place or something like it, I’m writing this so that you understand that you’re not alone. If you haven’t, congratulations - I hope this plays a small part in you better supporting a friend or family member who ends up here.
Modern startup writing likes to glorify failure as if repeating platitudes helps at all when you can’t open your laptop or get out of bed for fear of what the day holds; when the world seems to have turned against you and you’d rather be anyone else for the day (or the week, or the year).
Failure hurts so damn badly because, by its very nature, it hits us where it hurts the most. It drags out and shines light on all of our deepest insecurities and our worst fears. It is the death of dreams you held most tightly, and the dissolution of the confidence you spent years nurturing. It is not something I would wish on my worst enemy.
And yet, it is where the majority of hopeful ventures land. If you decide to join the realm of the daydreamers and pursue the noble act of creation, you will feel its sting.
So, what can we do about it? What is there possibly to do, when we are at our lowest? When hope has all but abandoned us, and we have nothing else to lose?
I am no longer the over-confident twenty-four year old with the gall to write an essay titled ‘From Suicide to Success’. I am just another entrepreneur, who is battered and bruised, but still standing in the ring, and has written down a few notes in the hopes you’ll find one or two helpful, if you ever find yourself needing them.
Here are my thoughts on failure, saying goodbye to a hard-fought dream, and finding what comes next:
If you feel like you’re over your skis, crash out early. That feeling of being trapped that Dr. Freeman speaks to being the leading cause of depression amongst founders? It comes from the stubbornness of realizing that you’ve leaned too far over your skis, and chosen to keep flying down the mountain instead of taking the crash. The idea that things will magically get better in the future if your foundation isn’t rock-solid now is a lie. Things will just get bigger, faster, and more perilous. Don’t hide things from your life partner, even though we know that you’re doing all of this for them. Take accountability for mistakes quickly. Life is too short to spend months or years drowning in stress and anxiety because you’re too scared to let go of something that is clearly done. Don’t let the fear of the unknown keep you from laying a dream to rest when its time has come. There is light on the other side, if you'd give it a chance.
It is ok to grieve. This may read dramatically. After all, no one died. Doesn’t matter. It is ok to give yourself the space to grieve. You can’t work through the end of a dream until you decide to stop judging yourself harshly for understandable emotions. Have the cry. Sleep in for a couple days. Eat the ice cream. Just be prepared to pull yourself up by the bootstraps to get back to work afterwards.
Mental resilience is not earned for life. It must be maintained. We do not do the work in therapy, or with ancient wisdom, or modern self-help, to get to a better place and then just get to glide. The hard work you put in to building a resilient mind fades quickly without maintenance. You don’t evolve like a Pokemon with no chance of reverting to a Magikarp just because you were a Gyrados for a while. Build the habits, and keep them. Read the books that help you most over and over. Fight for the space and time to keep meditating and reading and exercising as if your life depends on it - because it just might.
After a failure, dedicate your attention to learning new things. Get out of the house. Take an absurd number of classes. Find new hobbies. Write creatively every day in a forum no one will ever see. Depression causes atrophy in brain regions that control mood and emotion, but here's the remarkable part: the brain can rewire itself through neuroplasticity - the formation of new neural connections in response to learning and novel experiences. When you actively pursue new skills and environments, you're not just ‘distracting yourself’, you're triggering genuine neurobiological recovery.
Alcohol did not, has not, and will not help anything. We live in an alcohol-obsessed society. Startup culture is infamously riddled by the expectation to drink at mixers, dinners and conferences. The idea that going out to commiserate with your friends, as they console you over beers, will help in any way shape or form is a flat out lie. Look, I’ve enjoyed a cold one with the best of them - and I’m not claiming to be in a position to tell you how to live your life. But if you’re going through a loss and major life adjustment, there is never a better time to cut out alcohol. You will sleep better. You will deal with tough days in a healthier fashion. You will not miss the nights out with your friends as much as you’re worried you will. Just do it.
Don’t let an anxious day go by without exercising. When anxiety is crushing you, your brain is literally being reshaped by stress. Chronic stress causes persistent activation of the HPA axis, leading to consistently high levels of cortisol - the hormone that, over time, can damage the very neural structures you need to regulate your mood. Exercise enhances BDNF release, promoting dendritic spine integrity and activating pathways that contribute to neuroplasticity. BDNF (Brain-Derived Neurotrophic Factor) is essentially miracle-gro for your brain, it counteracts the adverse effects of excessive stress-induced glucocorticoid signaling and has been implicated as a resilience factor against psychopathology caused by chronic stress. The relationship is antagonistic: higher BDNF peaks after stress were associated with steeper cortisol recovery, and the magnitude of the cortisol stress response was linked to steeper BDNF recovery after stress. Translation: exercise literally fights the stress hormone at a molecular level. Your body literally creates its own anti-anxiety medication when you run, lift, swim, or move. Don't skip the dose on a single day you find yourself panicking.
Use the open space to fall back in love with the little things you love. Moments with your child you would’ve missed while at the office. An extra night with your partner to cook dinner together because you aren’t wining and dining investors. Slow mornings spent reading when you would’ve been rushing out of the door. Long lunches catching up with old friends. Extra time sitting in the park with your dog instead of rushing back. Failure sucks. Every moment afterwards doesn’t have to.
Resist the temptation to fill your time with traditional media. This is not the time to rewatch Game of Thrones. You do not need to know what happens in the newest season of Love Island. You need to carefully fill your mind with as much insightful, powerful and positive wisdom as you can fit. Read Man’s Search for Meaning. Listen to The Courage to Be Disliked. Spend your time on YouTube learning from Mark, Alex, Chris and Mel. Spend quality time with Alan Watts. If you really feel like you need a kick in the rear end, let Jim Rohn yell at you for a bit. Just don’t fall into the trap of filling your newly acquired time in the day with low-quality content. Journal daily. Write out your visions for what your life should look like. Find mantras or mottos that resonate and repeat them often.
Don’t wait too long to get back to it. It can be terrifying to imagine getting back to work after a humiliating failure. The scope of the nothingness can be obscenely daunting. But what else are you going to do? Once you’ve taken the time to grieve and reset, brush off the old overalls, and get back to work. You don’t need to figure out what the perfect first step is to ensure you have a great year. You don’t need to start working on the next big thing. You don’t need to write a manifesto, launch a future unicorn, or change the world. You can just start with doing the best thing for this hour. Get your thoughts out on paper. Don’t have any thoughts? Start grabbing coffee with friends and connections to discuss what they’re working on. And this is key, once you get restarted, no matter how little momentum you may feel, start going to work every single day. Check in at the desk, fight off resistance (thank you, Steven Pressfield), and do the work. Get the gears going again. Nothing else will come close to helping you move on from your last project.
You are enough, even here in these worst of moments. It may take some time to find a way to feel good about yourself again (that will come in time, through the work). However, don’t wait too long to forgive yourself. Even now, when you’re feeling worthless - especially now, know that you are enough, you are human, and you deserve to feel joy, even in small amounts through small things.
When the worry of what other people think becomes too much, remember the division of tasks. The great psychologist Alfred Adler, the founder of individual psychology, speaks to the discovery of happiness through the simplification of the world via the proper division of tasks. Translation: worry about what you can control, forget the rest. It is your task to carry yourself in a way you can be proud of, and it is not your task to concern yourself with how you are perceived or judged. To paraphrase the Serenity Prayer, work to find peace from what you cannot change, courage to change the things you can, and the wisdom to know the difference.
Embrace the change to live a life more closely aligned with your values. A life transition as meaningful as this will be scary and it will be uncomfortable. Try your best to make the discomfort of change in this period a mechanism for re-arranging your life so that you can live this next chapter closer to your values. Start the project that you feel true purpose in. Find ways to give back, even when you’re feeling that you have little to give. Work deeply with yourself to rediscover your Why, and rebuild a life brick by brick in accordance with that reason for being here. I believe in you!
And that’s what it really comes down to in this chapter of life - courage. The courage to pick up and start again when everything and everyone advises otherwise. Albert Camus described Sisyphus as ‘the absurd hero’ because he chooses consciousness over escape, as he pushes that boulder up the hill again, and again, and again. He chooses to live life in the face of absurdity, and I certainly hope the same will be said for us when it’s all said and done.
For those of you who made it this far - thank you. If you or someone you know is going through a tough time, know that you’re not alone and that things will, eventually, get better. I’ve managed, with the incredible support of my family and close friends, to get back on the horse, and look forward to sharing more about our new projects soon that align more closely with my core values and vision for the future.
With that, we’ve come to the end of the first edition of Daydreamer Ventures. We started off with the light stuff, didn’t we? As we keep this train rolling next week, expect slightly shorter, more direct essays on topics ranging from growing your business in the age of AI, to ancient philosophy tested in today’s chaotic environment, to practical steps for early daydreamers to bring their imaginations into the world and create their first businesses. Consider subscribing if you’d like, and supporting if you can.
I hope to hear from you soon - until next time.
zh
If you or someone you know is going through a difficult time, please reach out. There is no shame in asking for help - it’s one of the bravest things you can do.
National Suicide Prevention Lifeline: 988 (call or text, 24/7)
Crisis Text Line: Text HOME to 741741
SAMHSA National Helpline: 1-800-662-4357 (free, confidential support for mental health and substance use, 24/7)
For entrepreneurs specifically, organizations like Founders Pledge and the Entrepreneurship + Mental Health Coalition are working to build better support systems. You’re not alone in this, and the isolation you feel is part of the problem—not a reflection of reality.
If you’re not in crisis but know you need support, start with your primary care doctor or reach out to a therapist. Many offer sliding scale fees, and it’s worth the investment in yourself.