Return-Path: Delivered-To: alvarochf@traceseis.com Received: from cs510.bluehost.com by cs510.bluehost.com with LMTP id 8JAnJRYJjmmj2AUAWiBQxw (envelope-from ) for ; Thu, 12 Feb 2026 10:08:38 -0700 Return-path: Envelope-to: alvarochf@traceseis.com Delivery-date: Thu, 12 Feb 2026 10:08:38 -0700 Received: from v526.v5375b7fa.use4.send.mailgun.net ([159.112.244.26]:61582) by cs510.bluehost.com with esmtps (TLS1.2) tls TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 (Exim 4.98.2) (envelope-from ) id 1vqaBC-00000001bqu-1CT1 for alvarochf@traceseis.com; Thu, 12 Feb 2026 10:08:38 -0700 DKIM-Signature: a=rsa-sha256; v=1; c=relaxed/relaxed; d=mg-d1.substack.com; q=dns/txt; s=k1; t=1770916102; x=1770923302; h=List-Unsubscribe-Post: List-Unsubscribe: List-Post: List-Id: List-Archive: List-Owner: Reply-To: In-Reply-To: References: Sender: Sender: Date: Message-Id: To: To: From: From: Subject: Subject: Content-Type: Mime-Version; bh=cGvt5W1yYSR59Qn/gWKddO+KbVpU1GJDDDT4JO3jH0o=; b=O3t35w4ab7y0I3RQ+6X+Wriw9yvgNZIwXOJYFCGGbcrgjObVP2y5o/chAZrCak1VuqACwG7CTpfBQ0z5lXZgrVA/alYVgglahhXt6zZy1NiVg4gvk5aPh36TD8l06Y1KwwBL1IyBhQ0pg2QvuqAt7+BW1kBypicjkeTfohrtxvo= X-Mailgun-Sid: WyJiYTg1MiIsImFsdmFyb2NoZkB0cmFjZXNlaXMuY29tIiwiMzliMDhjNiJd Received: by 3c4f0555637a1b0c739887f836a5ca64f730422f8e8dc76514f3da2c1627f38f with HTTP id 698e090515ac479b4b919a4b; Thu, 12 Feb 2026 17:08:19 GMT X-Mailgun-Sending-Ip: 159.112.244.26 X-Mailgun-Batch-Id: 698e0904876aa3fd84f13cc8 Mime-Version: 1.0 Content-Type: multipart/alternative; boundary="dcba329a3acbde36213ba650346afe3cf8ff29abeb5a45c294f0ff1930ef" Subject: On Failure and Forgiving Yourself From: Zack Holland To: alvarochf@traceseis.com X-Mailgun-Tag: post X-Mailgun-Track-Clicks: false Message-Id: <20260212170512.3.6a032ce6a6939802@mg-d1.substack.com> Date: Thu, 12 Feb 2026 17:05:12 +0000 Feedback-Id: post-187539031:cat-post:pub-7966316:substack Sender: Zack Holland References: In-Reply-To: Reply-To: Zack Holland List-Owner: List-Url: List-Archive: List-Id: List-Post: List-Unsubscribe: List-Unsubscribe-Post: List-Unsubscribe=One-Click X-Mailgun-Variables: {"category": "post", "email_generated_at": "1770916099463", "is_freemail": "true", "post_audience": "everyone", "post_id": "187539031", "post_type": "newsletter", "pub_community_enabled": "true", "publication_id": "7966316", "subdomain": "daydreamerventures", "user_id": "347258985"} --dcba329a3acbde36213ba650346afe3cf8ff29abeb5a45c294f0ff1930ef Content-Type: text/plain; charset="utf-8" Content-Transfer-Encoding: quoted-printable View this post on the web at https://daydreamerventures.substack.com/p/on-f= ailure-and-forgiving-yourself =E2=80=9CThrow off displeasure at your nature; forgive your own individuali= ty. You have in yourself a ladder with a hundred steps to mount to knowledg= e.=E2=80=9D - Frieddy Nietzsche How the absolute hell am I here again?=20 Daydreamer Ventures is a reader-supported publication. To receive new posts= and support my work, consider becoming a free or paid subscriber. I=E2=80=99m sitting on the side of a busy street on a freezing cold night i= n Seattle, Washington. It=E2=80=99s dark and pouring rain in the middle of = December, yet I=E2=80=99m just wearing a t-shirt, fending off the chill wit= h a solid buzz.=20 This was supposed to be a pleasant trip with my brother and dad to see a Se= ahawks game. I wasn=E2=80=99t supposed to make it about me. I was supposed = to have grown out of these desperate and manic downward spirals. I had lear= ned the healthy systems to cope with my departure from the business I spent= six painstaking years building. I was a more evolved, educated, and reason= able 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 resili= ence on podcasts. I had even written a few chapters of a book titled =E2=80= =98From Suicide to Success=E2=80=99=E2=80=A6=20 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 crush= ing weight of knowing that I had failed, again.=20 Apologies for the lack of a trigger warning there, folks. I=E2=80=99ve been= told I have a penchant for the dramatic, so what better way to begin a bra= nd new essay and newsletter series than an old fashion dark-spiral moment?= =20 Life has changed a great deal in the short months since that bitter Seattle= night - and I=E2=80=99m 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, we= lcome to Daydreamer Ventures. While all of my posts won=E2=80=99t begin wit= h 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 dialo= gue, in the hopes of cutting through the bs that we=E2=80=99re all constant= ly drowning in to reach some kind of a genuine conversation.=20 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 newsle= tter here. There are plenty of AI talk-tracks and repurposed content factor= ies for that. This is straight learning-earned-from-mistakes-made, written = in flow. We=E2=80=99re going to fly with no auto-pilot, as we navigate thes= e murky skies together without Father Altman and Cousin Claude=E2=80=99s bl= essings, so please excuse the occasional typo or run-on sentence. This firs= t post, especially, may feel as though it is wandering off into some strang= e 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 h= elpful 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 a= mong us - whoever I can get on the phone. For this first essay, I=E2=80=99d 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 en= d and I would venture to guess that one little tidbit will stick with you f= or the next time you=E2=80=99re forced into that terrible position of stari= ng down the barrel of a devastating failure, and struggling to find a way t= o re-establish your sense of self, much less your confidence, in the afterm= ath. If you=E2=80=99re 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.=20 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 li= ving room floor in our family=E2=80=99s Boise house in 1994, asking the vac= uum repairman how each piece of the vacuum worked, only to take it complete= ly 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 acros= s the entire room.=20 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 R= ica, and then to a tiny village in the middle of the Amazon Rainforest call= ed Shell Mera, Ecuador.=20 While my father worked as a medical doctor in the small 30-bed hospital the= re, and my mother did everything from teaching classes for the indigenous t= ribes to finding ways to throw extravagant themed birthday parties for thre= e 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 soc= iety=E2=80=99s largest issues.=20 I started little businesses for everything I could think up: shoe-shining f= or 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 illus= trious forty film collection for the other families in the village. In shor= t, I was definitely a bit of a weird kid.=20 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 daydre= amers - and whether it=E2=80=99s 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.=20 Research from the Kauffman Foundation found that nearly half of entrepreneu= rs score high on ADHD indices - not as a disorder, but as a cognitive diffe= rence that enables pattern recognition and creative problem-solving. Dr. Sc= ott Barry Kaufman's work on 'mind-wandering' shows that the brain's default= mode network - active during daydreaming - is essential for creative insig= ht and long-term planning. The ideators are our most vital resource, if we hope to improve the state o= f things: the student staring out of the classroom window imagining the clo= uds as Studio Ghibli airships or the intern sitting uncomfortably in a poor= -fitting suit, fantasizing about their innovative fashion line while fetchi= ng coffee.=20 I also believe that, despite our adulation of a few well-branded billionair= es, our society doesn=E2=80=99t do a very good job encouraging this vital s= ect. Instead we mold and prescribe and systematize, attempting to ensure th= at dreamers spend their days nodding along to the beat of the drum - we use= d to dream bigger, and more freely, in this country. We fill every open spa= ce with a notification or a feed, and the thought of walking in silence or = laying in bed without a screen terrifies us.=20 The motivational YouTube videos and hustle-influencers are simply the sophi= sticated and algorithmic systems used to keep the next generation of daydre= amers glued to their phones instead of out thinking and building and writin= g 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.=20 "Imagination is more important than knowledge. For knowledge is limited to = all we now know and understand, while imagination embraces the entire world= =2E"=20 - Albert Einstein Luckily for me, Emperor Zuck wouldn=E2=80=99t start coding for years, Tom w= asn=E2=80=99t everyone=E2=80=99s friend just yet - and down in the jungles = of Ecuador there was plenty of space for a weird kid to simply be. I had th= e space to dream.=20 Ironically, things really clicked into gear the day a very special package = arrived from the United States.=20 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 =E2=80= =9Cthis has to be the coolest thing that humans have done so far.=E2=80=9D= =20 From that point forward, connecting people through and creating for the dig= ital screen would always be a part of my life. Upon our return to the Unite= d States I started my first official small business, Neighborhood Knowledge= , that sought to connect neighbors who had a need for, or could provide, se= rvices 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 r= est of my career.=20 After studying philosophy at USC, I dove into my next project: connecting u= p-and-coming painters, who were struggling to pay the rent despite being in= credibly talented, with city-dwelling young professionals who all hung the = same sad IKEA print on their apartment walls; this was ArtLifted. The compa= ny started off strong, and we donated thousands to an amazing non-profit or= ganization 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 firs= t came in contact with the potential for entrepreneurship to have devastati= ng effects on a person=E2=80=99s 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.=20 As any founder knows, starting a business requires an unusual amount of eff= ort. That level of effort is typically only possible through a complete fus= ion of your personality with the company=E2=80=99s - to a degree that natur= ally makes W2 employees deeply uncomfortable. We wake up and instantly star= t thinking of ways to fix our lead funnel. The shower is a space for tweaki= ng product, and evenings when others are watching the newest show are requi= red to create content and network. Once you start a business, your =E2=80= =98not-at-work=E2=80=99 persona entirely dissolves into an engine constantl= y committed to improving your slim chances at startup success. It is a natu= ral process, and one that many of the best entrepreneurs not only engage in= , but regularly teach and preach to those that follow them.=20 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= =2E Research from the University of Oxf= ord shows that when identity fusion oc= curs, people exhibit extreme pro-group behavior and self-sacrifice - it's w= hy 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=E2=80=99t simply a kn= ock to your ego in the modern sense of the word, but a real and serious cha= llenge to your ego in the ancient Greek fashion: the core of who =E2=80=98I= =E2=80=99 am. And that is just f*cking scary, no matter who you are.=20 The reactions to this experience vary, but one thing that is for certain - = we don=E2=80=99t speak enough about it. We don=E2=80=99t build resources an= d share content to ensure that people know that they aren=E2=80=99t alone, = even when they feel unbelievably, suffocatingly trapped.=20 Research shows entrepreneurs are twice as likely to report a lifetime histo= ry 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.=20 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 t= his dark spiral was the feeling of being trapped. The neuroscience here is = clear: when the brain perceives no escape route, it triggers the same neura= l pathways as physical entrapment. The amygdala hijacks executive function,= flooding the system with stress hormones that impair decision-making and f= uture-thinking - exactly what you need most in those moments. So, our dreamers are struggling - and the main driver of that depression an= d 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-bla= ck. I=E2=80=99ve 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 cha= nge ourselves." - Viktor Frankl In the months following the erasure of ArtLifted, as I sought out the authe= ntic 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, regul= ar reading and regular exercise. I worked hard to be more intentional in my= friendships, honest with my partner, and to maintain a better separation b= etween business and my conscious self. I looked to build an operating syste= m 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 insi= de - and for many years, it seemed to have worked.=20 The following years brought highs and lows aplenty as I worked to build age= ncies, consumer brands, and software products - now even in the worst of ti= mes, I could fall back on the frameworks that I had built. I had designed a= safety net so that even the greatest slip wouldn=E2=80=99t be fatal.=20 These were impactful and special years. I moved to New York, met my wife, a= nd we created a life for ourselves. I was blessed to work with incredible t= eammates, 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 Workpla= ces as recognition of the unanimous agreement that we had created a fantast= ic 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= =2E=20 But under the surface, there was trouble brewing. I stopped exercising, and= then I stopped reading. I found myself getting carried away drinking too o= ften, feeling constantly surrounded by it amongst the Brooklyn community I = had built. I was becoming overly obsessed with the work - I lost any separa= tion 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 begi= nning to fray and falter, but I wasn=E2=80=99t paying attention.=20 And then things fell apart, and the net was nowhere to be found.=20 This is the first time I=E2=80=99m writing in public since my departure fro= m the AI business that I spent six years building. This is not the forum for details, but in short: during a difficult persona= l year, things did not go as planned. The outcome wasn=E2=80=99t what anyon= e hoped for - not for the business, not for the team, not for those who bel= ieved in what we were building. I stepped away from the company that I had spent more than half a decade bu= ilding, 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 co= mparison to the failure I took so hard at twenty-three, here the stakes fel= t far higher. The expectations were greater. The weight of disappointing pe= ople I respect was crushing. I blinked, and I was eleven years older, and r= ight back in the same dark place, without the healthy foundations I had use= d to climb out last time.=20 I had lost friends and walked away from what felt like my dream role - whic= h paled in comparison to the heaviness of losing a great deal of respect fo= r myself. My fragile ego that was constructed out of press mentions and emp= loyee adoration came crashing down like the house of cards it really was. A= nd before I knew it, I was standing on a curb in the freezing rain in Seatt= le. If you=E2=80=99ve found yourself in this place or something like it, I=E2= =80=99m writing this so that you understand that you=E2=80=99re not alone. = If you haven=E2=80=99t, congratulations - I hope this plays a small part in= you better supporting a friend or family member who ends up here.=20 Modern startup writing likes to glorify failure as if repeating platitudes = helps at all when you can=E2=80=99t 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=E2=80=99d rather be anyone else for the day (or the week, or the y= ear).=20 Failure hurts so damn badly because, by its very nature, it hits us where i= t hurts the most. It drags out and shines light on all of our deepest insec= urities and our worst fears. It is the death of dreams you held most tightl= y, and the dissolution of the confidence you spent years nurturing. It is n= ot something I would wish on my worst enemy.=20 And yet, it is where the majority of hopeful ventures land. If you decide t= o join the realm of the daydreamers and pursue the noble act of creation, y= ou will feel its sting.=20 So, what can we do about it? What is there possibly to do, when we are at o= ur lowest? When hope has all but abandoned us, and we have nothing else to = lose?=20 I am no longer the over-confident twenty-four year old with the gall to wri= te an essay titled =E2=80=98From Suicide to Success=E2=80=99. I am just ano= ther entrepreneur, who is battered and bruised, but still standing in the r= ing, and has written down a few notes in the hopes you=E2=80=99ll find one = or two helpful, if you ever find yourself needing them.=20 Here are my thoughts on failure, saying goodbye to a hard-fought dream, and= finding what comes next: If you feel like you=E2=80=99re over your skis, crash out early. That feeli= ng of being trapped that Dr. Freeman speaks to being the leading cause of d= epression amongst founders? It comes from the stubbornness of realizing tha= t you=E2=80=99ve leaned too far over your skis, and chosen to keep flying d= own the mountain instead of taking the crash. The idea that things will mag= ically get better in the future if your foundation isn=E2=80=99t rock-solid= now is a lie. Things will just get bigger, faster, and more perilous. Don= =E2=80=99t hide things from your life partner, even though we know that you= =E2=80=99re doing all of this for them. Take accountability for mistakes qu= ickly. Life is too short to spend months or years drowning in stress and an= xiety because you=E2=80=99re too scared to let go of something that is clea= rly done. Don=E2=80=99t 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.=20 It is ok to grieve. This may read dramatically. After all, no one died. Doe= sn=E2=80=99t matter. It is ok to give yourself the space to grieve. You can= =E2=80=99t 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 th= e bootstraps to get back to work afterwards.=20 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=E2=80= =99t evolve like a Pokemon with no chance of reverting to a Magikarp just b= ecause you were a Gyrados for a while. Build the habits, and keep them. Rea= d 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.=20 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 creat= ively 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 p= art: 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 =E2=80=98= distracting yourself=E2=80=99, you're triggering genuine neurobiological re= covery. Alcohol did not, has not, and will not help anything. We live in an alcohol= -obsessed society. Startup culture is infamously riddled by the expectatio= n to drink at mixers, dinners and conferences. The idea that going out to c= ommiserate with your friends, as they console you over beers, will help in = any way shape or form is a flat out lie. Look, I=E2=80=99ve enjoyed a cold = one with the best of them - and I=E2=80=99m not claiming to be in a positio= n to tell you how to live your life. But if you=E2=80=99re going through a = loss and major life adjustment, there is never a better time to cut out alc= ohol. You will sleep better. You will deal with tough days in a healthier f= ashion. You will not miss the nights out with your friends as much as you= =E2=80=99re worried you will. Just do it.=20 Don=E2=80=99t let an anxious day go by without exercising. When anxiety is = crushing you, your brain is literally being reshaped by stress. Chronic str= ess causes persistent activation of the HPA axis, leading to consistently h= igh levels of cortisol - the hormone that, over time, can damage the very n= eural structures you need to regulate your mood. Exercise enhances BDNF rel= ease, promoting dendritic spine integrity and activating pathways that cont= ribute to neuroplasticity. BDNF (Brain-Derived Neurotrophic Factor) is esse= ntially miracle-gro for your brain, it counteracts the adverse effects of e= xcessive 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 associate= d with steeper cortisol recovery, and the magnitude of the cortisol stress = response was linked to steeper BDNF recovery after stress. Translation: exe= rcise literally fights the stress hormone at a molecular level. Your body l= iterally 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.= =20 Use the open space to fall back in love with the little things you love. Mo= ments with your child you would=E2=80=99ve missed while at the office. An e= xtra night with your partner to cook dinner together because you aren=E2=80= =99t wining and dining investors. Slow mornings spent reading when you woul= d=E2=80=99ve been rushing out of the door. Long lunches catching up with ol= d friends. Extra time sitting in the park with your dog instead of rushing = back. Failure sucks. Every moment afterwards doesn=E2=80=99t have to.=20 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 w= ith as much insightful, powerful and positive wisdom as you can fit. Read M= an=E2=80=99s Search for Meaning [ https://link.sbstck.com/redirect/0f2209ef= -afc6-4eb1-9b37-d1a5f5d99ee0?j=3DeyJ1IjoiNXFxeXF4In0.h9dEDbGj64cTNudluPwbMY= WklSu8UKGoFv6eWS-HyoA ]. Listen to The Courage to Be Disliked [ https://lin= k.sbstck.com/redirect/3ad671a3-cefb-4ff2-acd8-1a1e3aa33a9f?j=3DeyJ1IjoiNXFx= eXF4In0.h9dEDbGj64cTNudluPwbMYWklSu8UKGoFv6eWS-HyoA ]. Spend your time on Y= ouTube learning from Mark [ https://link.sbstck.com/redirect/9980dafb-7cd2-= 4539-b638-6098ab6f2a2e?j=3DeyJ1IjoiNXFxeXF4In0.h9dEDbGj64cTNudluPwbMYWklSu8= UKGoFv6eWS-HyoA ], Alex [ https://link.sbstck.com/redirect/6adbffc4-85fe-44= fb-904d-5b3293dde63c?j=3DeyJ1IjoiNXFxeXF4In0.h9dEDbGj64cTNudluPwbMYWklSu8UK= GoFv6eWS-HyoA ], Chris [ https://link.sbstck.com/redirect/a49428fa-3015-45d= a-9c7a-4626cf6022d0?j=3DeyJ1IjoiNXFxeXF4In0.h9dEDbGj64cTNudluPwbMYWklSu8UKG= oFv6eWS-HyoA ] and Mel [ https://link.sbstck.com/redirect/bbb08b41-2a16-4de= 1-85bf-4b175d7ec814?j=3DeyJ1IjoiNXFxeXF4In0.h9dEDbGj64cTNudluPwbMYWklSu8UKG= oFv6eWS-HyoA ]. Spend quality time with Alan Watts [ https://link.sbstck.co= m/redirect/5abd82a2-1ece-458b-b807-65256aa6d35e?j=3DeyJ1IjoiNXFxeXF4In0.h9d= EDbGj64cTNudluPwbMYWklSu8UKGoFv6eWS-HyoA ]. If you really feel like you nee= d a kick in the rear end, let Jim Rohn [ https://link.sbstck.com/redirect/2= 8e47612-4234-4bed-b56a-fc2dc30acd07?j=3DeyJ1IjoiNXFxeXF4In0.h9dEDbGj64cTNud= luPwbMYWklSu8UKGoFv6eWS-HyoA ] yell at you for a bit. Just don=E2=80=99t fa= ll into the trap of filling your newly acquired time in the day with low-qu= ality content. Journal daily. Write out your visions for what your life sho= uld look like. Find mantras or mottos that resonate and repeat them often.= =20 Don=E2=80=99t wait too long to get back to it. It can be terrifying to imag= ine getting back to work after a humiliating failure. The scope of the noth= ingness can be obscenely daunting. But what else are you going to do? Once = you=E2=80=99ve taken the time to grieve and reset, brush off the old overal= ls, and get back to work. You don=E2=80=99t need to figure out what the per= fect first step is to ensure you have a great year. You don=E2=80=99t need = to start working on the next big thing. You don=E2=80=99t need to write a m= anifesto, 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. Do= n=E2=80=99t have any thoughts? Start grabbing coffee with friends and conne= ctions to discuss what they=E2=80=99re working on. And this is key, once yo= u 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 y= ou, 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. =20 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, th= rough the work). However, don=E2=80=99t wait too long to forgive yourself. = Even now, when you=E2=80=99re 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.=20 When the worry of what other people think becomes too much, remember the di= vision of tasks. The great psychologist Alfred Adler, the founder of indivi= dual psychology, speaks to the discovery of happiness through the simplific= ation of the world via the proper division of tasks. Translation: worry abo= ut 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, wo= rk 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 uncomfor= table. Try your best to make the discomfort of change in this period a mech= anism for re-arranging your life so that you can live this next chapter clo= ser to your values. Start the project that you feel true purpose in. Find w= ays to give back, even when you=E2=80=99re 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=E2=80=99s what it really comes down to in this chapter of life - c= ourage. The courage to pick up and start again when everything and everyone= advises otherwise. Albert Camus described Sisyphus as =E2=80=98the absurd = hero=E2=80=99 because he chooses consciousness over escape, as he pushes th= at 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 u= s when it=E2=80=99s all said and done.=20 For those of you who made it this far - thank you. If you or someone you kn= ow is going through a tough time, know that you=E2=80=99re not alone and th= at things will, eventually, get better. I=E2=80=99ve managed, with the incr= edible support of my family and close friends, to get back on the horse, an= d look forward to sharing more about our new projects soon that align more = closely with my core values and vision for the future.=20 With that, we=E2=80=99ve come to the end of the first edition of Daydreamer= Ventures. We started off with the light stuff, didn=E2=80=99t we? As we ke= ep this train rolling next week, expect slightly shorter, more direct essay= s on topics ranging from growing your business in the age of AI, to ancient= philosophy tested in today=E2=80=99s chaotic environment, to practical ste= ps for early daydreamers to bring their imaginations into the world and cre= ate their first businesses. Consider subscribing if you=E2=80=99d like, and= supporting if you can.=20 I hope to hear from you soon - until next time.=20 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=E2=80=99s 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 me= ntal health and substance use, 24/7) For entrepreneurs specifically, organizations like Founders Pledge and the = Entrepreneurship + Mental Health Coalition are working to build better supp= ort systems. You=E2=80=99re not alone in this, and the isolation you feel i= s part of the problem=E2=80=94not a reflection of reality. If you=E2=80=99re not in crisis but know you need support, start with your = primary care doctor or reach out to a therapist. Many offer sliding scale f= ees, and it=E2=80=99s worth the investment in yourself. Daydreamer Ventures is a reader-supported publication. To receive new posts= and support my work, consider becoming a free or paid subscriber. Unsubscribe https://substack.com/redirect/2/eyJlIjoiaHR0cHM6Ly9kYXlkcmVhbWV= ydmVudHVyZXMuc3Vic3RhY2suY29tL2FjdGlvbi9kaXNhYmxlX2VtYWlsP3Rva2VuPWV5SjFjMl= Z5WDJsa0lqb3pORGN5TlRnNU9EVXNJbkJ2YzNSZmFXUWlPakU0TnpVek9UQXpNU3dpYVdGMElqb= 3hOemN3T1RFMk1EazRMQ0psZUhBaU9qRTRNREkwTlRJd09UZ3NJbWx6Y3lJNkluQjFZaTAzT1RZ= Mk16RTJJaXdpYzNWaUlqb2laR2x6WVdKc1pWOWxiV0ZwYkNKOS40RmN1NHZjODZrQnJkSkdMVzd= sOFV4cE1VT1Z4bmtUS05yaEVHcXBsc2NNIiwicCI6MTg3NTM5MDMxLCJzIjo3OTY2MzE2LCJmIj= p0cnVlLCJ1IjozNDcyNTg5ODUsImlhdCI6MTc3MDkxNjA5OCwiZXhwIjoyMDg2NDkyMDk4LCJpc= 3MiOiJwdWItMCIsInN1YiI6ImxpbmstcmVkaXJlY3QifQ.qi-ScYA91R4jiog1acOwB8vnX8-gD= LR4RqTwWpD0wrI? --dcba329a3acbde36213ba650346afe3cf8ff29abeb5a45c294f0ff1930ef Content-Type: text/html; charset="utf-8" Content-Transfer-Encoding: quoted-printable On Failure and Forgiving= Yourself3D""
Thoughts on laying a determined dream to rest, and what c= omes next
͏     ­͏     ­͏ &= nbsp;   ­͏     ­͏     ­= ;͏     ­͏     ­͏   Q= 99; ­͏     ­͏     ­͏ &n= bsp;   ­͏     ­͏     ­= ͏     ­͏     ­͏   ̳= 9; ­͏     ­͏     ­͏ &nb= sp;   ­͏     ­͏     ­&= #847;     ­͏     ­͏    = ; ­͏     ­͏     ­͏ &nbs= p;   ­͏     ­͏     ­&#= 847;     ­͏     ­͏    = ­͏     ­͏     ­͏  = ;   ­͏     ­͏     ­= 47;     ­͏     ­͏     = ­͏     ­͏     ­͏  =   ­͏     ­͏     ­T= 7;     ­͏     ­͏     &= #173;͏     ­͏     ­͏   =   ­͏     ­͏     ­͏= ;     ­͏     ­͏     &#= 173;͏     ­͏     ­͏   &= #8199; ­͏     ­͏     ­͏=     ­͏     ­͏     = 73;͏     ­͏     ­͏   &#= 8199; ­͏     ­͏     ­͏ =     ­͏     ­͏     = 3;͏     ­͏     ­͏   = 199; ­͏     ­͏     ­͏ &= nbsp;   ­͏     ­͏     ­= ;͏     ­͏     ­͏   Q= 99; ­͏     ­͏     ­͏ &n= bsp;   ­͏     ­͏     ­= ͏     ­͏     ­͏   ̳= 9; ­͏     ­͏     ­͏ &nb= sp;   ­͏     ­͏     ­&= #847;     ­͏     ­͏    = ; ­͏     ­͏     ­͏ &nbs= p;   ­͏     ­͏     ­&#= 847;     ­͏     ­͏    = ­͏     ­͏     ­͏  = ;   ­͏     ­͏     ­= 47;     ­͏     ­͏     = ­͏     ­͏     ­͏  =   ­͏     ­͏     ­T= 7;     ­͏     ­͏     &= #173;͏     ­͏     ­͏   =   ­͏     ­͏     ­͏= ;     ­͏     ­͏     &#= 173;͏     ­͏     ­͏   &= #8199; ­͏     ­͏     ­͏=     ­͏     ­͏     = 73;͏     ­͏     ­͏   &#= 8199; ­͏     ­͏     ­͏ =     ­͏     ­͏     = 3;͏     ­͏     ­͏   = 199; ­͏     ­͏     ­͏ &= nbsp;   ­͏     ­͏     ­= ;͏     ­͏     ­͏   Q= 99; ­͏     ­͏     ­͏ &n= bsp;   ­͏     ­͏     ­= ͏     ­͏     ­͏   ̳= 9; ­͏     ­͏     ­͏ &nb= sp;   ­͏     ­͏     ­&= #847;     ­͏     ­͏    = ; ­͏     ­͏     ­͏ &nbs= p;   ­͏     ­͏     ­&#= 847;     ­͏     ­͏    = ­͏     ­͏     ­͏  = ;   ­͏     ­͏     ­= 47;     ­͏     ­͏     = ­͏     ­͏     ­͏  =   ­͏     ­͏     ­T= 7;     ­͏     ­͏     &= #173;͏     ­͏     ­
<= table role=3D"presentation" width=3D"auto" border=3D"0" cellspacing=3D"0" c= ellpadding=3D"0">
Forwarded this email? Subscribe here for more
<= h1 class=3D"post-title published title-X77sOw" dir=3D"auto" style=3D"direct= ion: auto;text-align: start;unicode-bidi: isolate;color: rgb(54,55,55);font= -family: 'SF Pro Display',-apple-system-headline,system-ui,-apple-system,Bl= inkMacSystemFont,'Segoe UI',Roboto,Helvetica,Arial,sans-serif,'Apple Color = Emoji','Segoe UI Emoji','Segoe UI Symbol';font-weight: bold;-webkit-font-sm= oothing: antialiased;-moz-osx-font-smoothing: antialiased;-webkit-appearanc= e: optimizelegibility;-moz-appearance: optimizelegibility;appearance: optim= izelegibility;margin: 0;line-height: 36px;font-size: 32px;">On Failure and Fo= rgiving Yourself

Thoughts on laying a determined dream to rest, and wha= t comes next

Zack Holland
 
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READ IN APP<= img class=3D"icon text-icon" src=3D"https://substackcdn.com/image/fetch/$s_= !ET-_!,w_36,c_scale,f_png,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsu= bstack.com%2Ficon%2FLucideArrowUpRight%3Fv%3D4%26height%3D36%26fill%3Dnone%= 26stroke%3D%2523808080%26strokeWidth%3D2" width=3D"18" height=3D"18" style= =3D"min-width: 18px;min-height: 18px;border: none;vertical-align: middle;ma= rgin-right: 0;margin-left: 0;max-width: 18px" alt=3D"">
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Welcome to Daydreamer Ventures
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3D""
Our old founder friend Sisyphus on attempt no. 76418= 2 with the boulder

“Throw off displeasure at your nature; forgive your own indi= viduality. You have in yourself a ladder with a hundred steps to mount to k= nowledge.” - Frieddy Nietzsche

How the absolute hell am I here again?

Daydreamer Ventures is a reader-supported publicat= ion. To receive new posts and support my work, consider becoming a free or = paid subscriber.

<= a class=3D"button subscribe-btn primary" href=3D"https://substack.com/redir= ect/2/eyJlIjoiaHR0cHM6Ly9kYXlkcmVhbWVydmVudHVyZXMuc3Vic3RhY2suY29tL3N1YnNjc= mliZT91dG1fc291cmNlPXBvc3QmdXRtX2NhbXBhaWduPWVtYWlsLWNoZWNrb3V0Jm5leHQ9aHR0= cHMlM0ElMkYlMkZkYXlkcmVhbWVydmVudHVyZXMuc3Vic3RhY2suY29tJTJGcCUyRm9uLWZhaWx= 1cmUtYW5kLWZvcmdpdmluZy15b3Vyc2VsZiZyPTVxcXlxeCZ0b2tlbj1leUoxYzJWeVgybGtJam= 96TkRjeU5UZzVPRFVzSW1saGRDSTZNVGMzTURreE5qQTVPQ3dpWlhod0lqb3hOemN6TlRBNE1Ea= zRMQ0pwYzNNaU9pSndkV0l0TnprMk5qTXhOaUlzSW5OMVlpSTZJbU5vWldOcmIzVjBJbjAuZFVp= SWdoTnlrcUdHNVltcFJSeXFmZEh6TmRNVnZtdE1YeklQZlVGZUtndyIsInAiOjE4NzUzOTAzMSw= icyI6Nzk2NjMxNiwiZiI6dHJ1ZSwidSI6MzQ3MjU4OTg1LCJpYXQiOjE3NzA5MTYwOTgsImV4cC= I6MjA4NjQ5MjA5OCwiaXNzIjoicHViLTAiLCJzdWIiOiJsaW5rLXJlZGlyZWN0In0.hXYvkBbQz= AE6Dls8Etl5O6CiR_qzAIdk9OK45r_pJlY?&utm_medium=3Demail&utm_source=3Dsubscri= be-widget-preamble&utm_content=3D187539031" style=3D"font-family: system-ui= ,-apple-system,BlinkMacSystemFont,'Segoe UI',Roboto,Helvetica,Arial,sans-se= rif,'Apple Color Emoji','Segoe UI Emoji','Segoe UI Symbol';display: inline-= block;box-sizing: border-box;cursor: pointer;border: none;border-radius: 8p= x;font-size: 14px;line-height: 20px;font-weight: 600;text-align: center;opa= city: 1;outline: none;white-space: nowrap;text-decoration: none !important;= margin: 0 auto;background-color: #292524;color: #ffffff !important;padding:= 12px 20px;height: auto;">Upgrade to paid

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, y= et I’m just wearing a t-shirt, fending off the chill with a solid buz= z.

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 m= e. I was supposed to have grown out of these desperate and manic downward s= pirals. I had learned the healthy systems to cope with my departure from th= e business I spent six painstaking years building. I was a more evolved, ed= ucated, and reasonable person than I was at twenty-three. I had written art= icles speaking to founder mental health, done the work in therapy, and shar= ed tips for resilience on podcasts. I had even written a few chapters of a = book titled ‘From Suicide to Success’…

<= span>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, fo= lks. I’ve been told I have a penchant for the dramatic, so what bette= r 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 f= orward to sharing updates with all of my dear friends and comrades that hav= e a moment to spare. But first, and here in my first public writing since t= he 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 t= o set a standard for these essays: one of truth-telling and raw dialogue, i= n the hopes of cutting through the bs that we’re all constantly drown= ing in to reach some kind of a genuine conversation.

As a format, expect ea= ch weekly Daydreamer post to discuss a specific topic, usually in the realm= s of startup, marketing or philosophy, with as much helpful and honest opin= ion 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 g= iants who lived before us, and the legends who live among us - whoever I ca= n 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 d= ear 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 l= ittle 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 les= s your confidence, in the aftermath. If you’re there, or have been th= ere recently - whoever you are, remember that you are far from alone, and t= hings get better.

From the bottom of my heart, thank you fo= r taking the time out of your busy day to read this, and share it/subscribe= if you found it interesting.

Share

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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 Bo= ise 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 bathr= oom. 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 shou= ld have been clear back then, as I wandered off to my next mental adventure= with pieces strewn asunder across the entire room.

For th= ose who are new to my story, my siblings and I lived a rather unique childh= ood. After a few early years in Boise, my parents moved us to Costa Rica, a= nd then to a tiny village in the middle of the Amazon Rainforest called She= ll Mera, Ecuador.

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My little brother Ben and I in 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 cl= asses 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 s= tarted little businesses for everything I could think up: shoe-shining for = the adults while my dad hosted Bible study, car-washing for the soldiers co= ming back from drives into the muddy jungle, movie rental from our illustri= ous forty film collection for the other families in the village. In short, = I was definitely a bit of a weird kid.

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Me as a weird kid

Despite my firm belief that anyone can learn to be an entr= epreneur, I also believe there are those of us who were born into the stran= ge clan of daydreamers - and whether it’s neurodivergence or somethin= g 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 an= d protected in any way possible.

Research from the Kauffma= n Foundation found that nearly half of entrepreneurs score high on ADHD ind= ices - not as a disorder, but as a cognitive difference that enables patter= n recognition and creative problem-solving. Dr. Scott Barry Kaufman's work = on 'mind-wandering' shows that the brain's default mode network - active du= ring daydreaming - is essential for creative insight and long-term planning= =2E

The ideators are our most vital resource, if we hope to i= mprove the state of things: the student staring out of the classroom window= imagining the clouds as Studio Ghibli airships or the intern sitting uncom= fortably in a poor-fitting suit, fantasizing about their innovative fashion= line while fetching coffee.

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I also believe that, despite our adulation of a few we= ll-branded billionaires, our society doesn’t do a very good job encou= raging this vital sect. Instead we mold and prescribe and systematize, atte= mpting to ensure that dreamers spend their days nodding along to the beat o= f 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 wal= king 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 tha= t 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 wo= rld."
- Albert Einstein

Ironically, things really clicked into gear = the day a very special package arrived from the United States.

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Young Zack in 2000 with = my first Gateway laptop

I have a cl= ear memory of the first time I opened the screen of that Gateway Solo lapto= p and seeing that beautiful cow-print cube logo, thinking “this has t= o be the coolest thing that humans have done so far.”

After studying philosophy at USC, I do= ve into my next project: connecting up-and-coming painters, who were strugg= ling 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 elem= entary school art classes through the process. However the concept was diff= icult to scale, and after a couple of years, and thousands of hours of effo= rt, it was time to shut things down.

It was here, through t= he 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 u= p 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 comple= te fusion of your personality with the company’s - to a degree that n= aturally 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 tw= eaking product, and evenings when others are watching the newest show are r= equired to create content and network. Once you start a business, your R= 16;not-at-work’ persona entirely dissolves into an engine constantly = committed to improving your slim chances at startup success. It is a natura= l 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= =2E Research from the University of Oxf= ord shows that when identity fusion oc= curs, people exhibit extreme pro-group behavior and self-sacrifice - it's w= hy founders will work themselves into the ground.

The flips= ide 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 y= our ego in the ancient Greek fashion: the core of who ‘I’ am. A= nd 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 d= on’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 sh= ows entrepreneurs are twice as likely to report a lifetime history of depre= ssion, and three times more likely to experience substance abuse and addict= ion. 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 ar= ea, 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 brai= n perceives no escape route, it triggers the same neural pathways as physic= al entrapment. The amygdala hijacks executive function, flooding the system= with stress hormones that impair decision-making and future-thinking - exa= ctly 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 e= xperiences, share the real truths from our own lives, and ensure people kno= w 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 lo= ng desired to start this community, Daydreamer Ventures, for exactly that r= eason.

"When we are no longer = able to change a situation, we are challenged to change ourselves." - Viktor Frankl

In the months f= ollowing the erasure of ArtLifted, as I sought out the authentic self hidin= g underneath my self-imposed identity, I worked to discover systems that wo= uld 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, h= onest 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 ma= ny years, it seemed to have worked.

The following years br= ought 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 ev= en the greatest slip wouldn’t be fatal.

These were i= mpactful and special years. I moved to New York, met my wife, and we create= d a life for ourselves. I was blessed to work with incredible teammates, in= ternationally-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 gue= st on more than twenty podcasts. Our team won Inc. Best Workplaces as recog= nition 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 exercisi= ng, and then I stopped reading. I found myself getting carried away drinkin= g too often, feeling constantly surrounded by it amongst the Brooklyn commu= nity 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 w= as beginning to fray and falter, but I wasn’t paying attention.

<= p style=3D"margin: 0 0 20px 0;color: rgb(54,55,55);line-height: 26px;font-s= ize: 16px;">And then things fell apart, and the net was nowhere to be found= =2E

This is the first time I’m writing in public since m= y 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 wh= o believed in what we were building.

I stepped away from th= e company that I had spent more than half a decade building, walking away f= rom the business that had consumed nearly a third of my working life, and f= rom a team that I genuinely cared deeply about. As an aside: the business i= s still growing and doing well under new leadership.

All of= this is not easy to write. It has not been an easy experience. In comparis= on 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 b= ack in the same dark place, without the healthy foundations I had used to c= limb out last time.

I had lost friends and walked away fro= m 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 cons= tructed out of press mentions and employee adoration came crashing down lik= e 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 foun= d yourself in this place or something like it, I’m writing this so th= at you understand that you’re not alone. If you haven’t, congra= tulations - I hope this plays a small part in you better supporting a frien= d or family member who ends up here.

Modern startup writin= g 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 ho= lds; 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).

Fa= ilure 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 insecur= ities 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 real= m of the daydreamers and pursue the noble act of creation, you will feel it= s sting.

So, what can we do about it? What is there possib= ly to do, when we are at our lowest? When hope has all but abandoned us, an= d we have nothing else to lose?

I am no longer the over-co= nfident twenty-four year old with the gall to write an essay titled ‘= From Suicide to Success’. I am just another entrepreneur, who is batt= ered and bruised, but still standing in the ring, and has written down a fe= w notes in the hopes you’ll find one or two helpful, if you ever find= yourself needing them.

Here are my thoughts on failure, s= aying goodbye to a hard-fought dream, and finding what comes next:

  1. If you fe= el like you’re over your skis, crash out early. That f= eeling 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 m= agically 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&= #8217;t hide things from your life partner, even though we know that you= 217;re doing all of this for them. Take accountability for mistakes quickly= =2E Life is too short to spend months o= r years drowning in stress and anxiety= because you’re too scared to let go of something that is clearly don= e. 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 giv= e it a chance.

  2. It is ok to g= rieve. This may read dramatically. After all, no one died. D= oesn’t matter. It is ok to give yourself the space to grie= ve. You can’t work through the end of a dream until you de= cide 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 pu= ll yourself up by the bootstraps to get back to work afterwards.

  3. Mental resilience is not earned for li= fe. 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 mi= nd 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 rea= ding and exercising as if your life depends on it - because it just might. =

  4. After a failure, dedicate yo= ur attention to learning new things. Get out of the house. T= ake an absurd number of classes. Find new hobbies. Write creatively every d= ay in a forum no one will ever see. Depression causes atrophy in brain regi= ons that control mood and emotion, but here's the remarkable part: the brai= n can rewire itself through neuroplasticity - the formation of new neural c= onnections in response to learning and novel experiences. When you actively= pursue new skills and environments, you're not just ‘distracting you= rself’, you're triggering genuine neurobiological recovery.

  5. Alcohol did not, has not, and will not= help anything. We live in an alcohol-obsessed society. Sta= rtup culture is infamously riddled by the expectation to drink at mixers, d= inners and conferences. The idea that going out to commiserate with your fr= iends, as they console you over beers, will help in any way shape or form i= s 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 y= our life. But if you’re going through a loss and major life adjustmen= t, 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. Jus= t do it.

  6. Don’t let an = anxious day go by without exercising. When anxiety is crushi= ng you, your brain is literally being reshaped by stress. Chronic stress ca= uses persistent activation of the HPA axis, leading to consistently high le= vels 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 essentiall= y miracle-gro for your brain, it counteracts the adverse effects of excessi= ve stress-induced glucocorticoid signaling and has been implicated as a res= ilience factor against psychopathology caused by chronic stress. The relati= onship is antagonistic: higher BDNF peaks after stress were associated with= steeper cortisol recovery, and the magnitude of the cortisol stress respon= se was linked to steeper BDNF recovery after stress. Translation: exercise = literally fights the stress hormone at a molecular level. Your body literal= ly creates its own anti-anxiety medication when you run, lift, swim, or mov= e. Don't skip the dose on a single day you find yourself panicking. =

  7. Use the open space to fall back in = love with the little things you love. Moments with your chil= d you would’ve missed while at the office. An extra night with your p= artner to cook dinner together because you aren’t wining and dining i= nvestors. Slow mornings spent reading when you would’ve been rushing = out of the door. Long lunches catching up with old friends. Extra time sitt= ing in the park with your dog instead of rushing back. Failure sucks. Every= moment afterwards doesn’t have to.

  8. Resist the temptation to fill your time with traditional medi= a. This is not the time to rewatch Game of Thrones. You do n= ot 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 Mea= ning. Listen to The Courage to Be Disliked. Spend your time on YouTube learning from Mar= k, Alex, Chri= s and Mel. Spend quality time with= Alan Watts. If you really feel like you nee= d 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 ou= t your visions for what your life should look like. Find mantras or mottos = that resonate and repeat them often.

  9. 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, brus= h off the old overalls, and get back to work. You don’t need to figur= e out what the perfect first step is to ensure you have a great year. You d= on’t need to start working on the next big thing. You don’t nee= d to write a manifesto, launch a future unicorn, or change the world. You c= an just start with doing the best thing for this hour. Get your thoughts ou= t on paper. Don’t have any thoughts? Start grabbing coffee with frien= ds and connections to discuss what they’re working on. And this is ke= y, once you get restarted, no matter how little momentum you may feel, star= t going to work every single day. Check in at the desk, fight off resistanc= e (thank you, Steven Pressfield), and do the work. Get the gears going agai= n. Nothing else will come close to helping you move on from your last proje= ct.

  10. You are enough, even h= ere 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 t= he work). However, don’t wait too long to forgive yourself. Even now,= when you’re feeling worthless - especially now, know that you are en= ough, you are human, and you deserve to feel joy, even in small amounts thr= ough small things.

  11. 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 sim= plification of the world via the proper division of tasks. Translation: wor= ry about what you can control, forget the rest. It is your task to carry yo= urself in a way you can be proud of, and it is not your task to concern you= rself with how you are perceived or judged. To paraphrase the Serenity Pray= er, work to find peace from what you cannot change, courage to change the t= hings you can, and the wisdom to know the difference.

  12. Embrace the change to live a life more closely ali= gned with your values. A life transition as meaningful as th= is will be scary and it will be uncomfortable. Try your best to make the di= scomfort 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 proje= ct that you feel true purpose in. Find ways to give back, even when youR= 17;re feeling that you have little to give. Work deeply with yourself to re= discover your Why, and rebuild a life brick by brick in accordance with tha= t reason for being here. I believe in you!

And that’s what it really comes down to in this chapter of life - co= urage. The courage to pick up and start again when everything and everyone = advises otherwise. Albert Camus described Sisyphus as ‘the absurd her= o’ because he chooses consciousness over escape, as he pushes that bo= ulder up the hill again, and again, and again. He chooses to live life in t= he face of absurdity, and I certainly hope the same will be said for us whe= n 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 toug= h time, know that you’re not alone and that things will, eventually, = get better. I’ve managed, with the incredible support of my family an= d 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 an= d vision for the future.

With that, we’ve come to the = end of the first edition of Daydreamer Ventures. We started off with the li= ght stuff, didn’t we? As we keep this train rolling next week, expect= slightly shorter, more direct essays on topics ranging from growing your b= usiness in the age of AI, to ancient philosophy tested in today’s cha= otic environment, to practical steps for early daydreamers to bring their i= maginations into the world and create their first businesses. Consider subs= cribing if you’d like, and supporting if you can.

I = hope to hear from you soon - until next time.

zh

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If you or someone you know is going through a difficult ti= me, please reach out. There is no shame in asking for help - it’s one= of the bravest things you can do.

Nationa= l Suicide Prevention Lifeline: 988 (call or text, 24/7)
Crisis Text Line: Text HOME to 741741SAMHSA National Helpline: 1-800-662-4357 (free, co= nfidential support for mental health and substance use, 24/7)

For entrepreneurs specifically, organizations like Found= ers Pledge and the Entrepreneurship + Mental Health Coalition are working t= o build better support systems. You’re not alone in this, and the iso= lation you feel is part of the problem—not a reflection of reality.

If you’re not in crisis but know you need sup= port, 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.=

Daydreamer Ventures is a = reader-supported publication. To receive new posts and support my work, con= sider becoming a free or paid subscriber.

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© 2026 Zack Holland
548 Market Street PMB 72296,= San Francisco, CA 94104
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