markdjacobsen

My own experience presiding over startup failure was excruciating. I had a serious personal breakdown that took a couple years to recover from. There was the burnout, but also a deep sense of guilt, weakness, and personal failure. Articles like this can inadvertently heap on guilt, insinuating that a founder "stopped trying" or "lost heart", as a if a better or stronger soul might have prevailed. But sometimes, closing the doors is the right thing to do.

For other failed founders out there... I found very few resources that could help me navigate the aftermath, so I wrote the book I wish I'd had. It's a passion project, so I give it away for free. It's titled "Eating Glass: The Inner Journey Through Failure and Renewal."

Amazon/Audible link: https://www.amazon.com/Eating-Glass-Journey-Through-Failure/...

Free copy: https://www.dropbox.com/scl/fi/arauyfnkwwezbbk0cbvdp/eating-...

On a related note, a science fiction short story anthology titled "Derelict" was published in 2021. When they were soliciting stories, I thought long and hard about how to put a creative twist on the topic. I wrote a story about a race to recover Elon's roadster, which made it into the anthology.

Free story: https://s3.us-west-1.amazonaws.com/com.markdjacobsen/Celesti...

Full anthology: https://www.amazon.com/Derelict-Campbell-Jack/dp/1940709407/

I spent a year and a half building a "startup" of my own (actually, a humanitarian nonprofit) that failed. I can relate to the author's painful emotions as he processes his experience. This emotional journey is common in entrepreneurship, but very few people talk about it, so I wrote the book I wish I'd had.

The book is titled "Eating Glass: The Inner Journey Through Failure and Renewal", and I mention it whenever these threads come up. It doesn't sell well, so I'm just giving it away for free.[0] I'm passionate about the topic.

Also, FWIW, although you acknowledge the mistakes in execution, this sounds like a brilliant idea.

[0] https://www.dropbox.com/scl/fi/arauyfnkwwezbbk0cbvdp/eating-...

I wrote a book called “Eating Glass” about the grueling emotional and psychological experience of presiding over a prolonged startup failure, coping with the aftermath, and finding my way back to health and growth.

I wrote the book I wished I’d had available to me, as I believe these experiences are common among entrepreneurs and high achievers. My “Show HN” was immediately lost downstream but I have given out free digital copies on a few occasions in response to folks posting here about similar struggles.

I have links and a lot of free excerpts at https://markdjacobsen.com/eating-glass/

I just replicated something very similar in a few minutes using the prompts in the article

I have been successful by most standards, with a litany of professional and educational achievements, a wonderful wife, three beautiful kids, and a life of exciting new experiences. But age 35 was a crucible year in which I presided over the scorching failure of a startup, struggled mightily in my PhD program, and reluctantly accepted that I no longer believed in the religious faith that had shaped my life. That change eventually cost me my marriage. It felt the universe took a sledgehammer to my life.

That year (7 years ago now) marks a "before" and "after" point in my life. It changed all my priorities. I'm much more relational now, much more focused on the present, and search for and find joy in simple, quiet, beautiful things. I still work hard but am far less attached to professional success. The faith change led me to abandon an identity that tormented me with cognitive dissonance, was rooted in social expectations, and never worked well for me; constructing a new, more authentic identity has not been easy but it has been one of the most rewarding experiences of my life.

In many ways, my journey has been a fairly conventional "midlife passage" (my preferred term over "midlife crisis"). I'm grateful for the experience, and thankful it came early enough that I could renew my life while still relatively young.

I wrote a book about my experience, in case it's helpful to anyone else: https://www.amazon.com/Eating-Glass-Journey-Through-Failure-...

This is a good post, and I'm always glad to see discussions about mental health anywhere in the startup scene. However, I agree with the other commenters who note that healthy routines may not be enough to cope with the stresses of running a startup, particularly given the high rate of failure. Even the strongest and healthiest individuals face a high risk of being strained past a breaking point. I wish we talked more about that.

I learned this the hard way, presiding over the failure of a nonprofit I founded. Nothing prepared me for the sheer level of stress and exhaustion, the aftermath, and the recovery process.

I wrote a book about this to help others, in case anyone is going through something similar: "Eating Glass: The Inner Journey Through Failure and Renewal." [0]

[0] www.markdjacobsen.com/eating-glass/

I have the dubious distinction of having burned down three acres of Stanford's Lake Lagunita with a Li Po battery after crashing a drone (this was a soft pack for a DIY drone). We had been meticulous about charging and handling safety, but they still light off like fireworks if punctured. Seven years later, I'm still terrified of these batteries and treat them like explosives.

The fact that you care about employee development and are deliberately seeking out ways to do it better puts you ahead of most managers. I can't directly address advancement within a company, but will share some of my own experience.

I founded and led a small software development team within government that was a mix of government employees and contractors, but we acted like a startup and had a strong culture and team ethos. I was under severe constraints about what I could actually offer my team members in terms of advancement, but I tried to deliberately help them grow. I cared about them for their own sake, but also believed they would do their best work for my team if they felt valued, taken care of, and fulfilled in their desire for growth.

I did a one-on-one with team member upon hiring, and then every 6 months or so. We used these meetings for mutual feedback but I also deliberately asked about their goals and we strategized together about how to help them advance towards those goals. I was honest about the limits of what I could do. Even though I couldn't directly promote people, we often found ways to help team members learn new skill sets in the course of their work, take on more leadership, or shift into different lateral roles that would stretch their knowledge and abilities. In some cases I worked with our contractor company to pay for training in new skills adjacent to, but not directly related to, their core duties.

I also acknowledged in our first one-on-one that this job was just one of many they would hold. I hoped they would stay with us a long time, but whenever they left, we would wish them well and help them transition into their next thing. I also told them one of my personal goals for each new hire: that they would be better for the time they spent on our team.

These individuals stayed fiercely loyal to the team. Most stayed for quite a while. Many did leave for higher-paying jobs after a couple years, but it was always a difficult decision for them because they loved the team and the mission so much. When they did decide to leave, we always wrote recommendations and did whatever else we could to help them find their next opportunity.

I'm sorry you've been going through this. I can relate somewhat. I have been successful by most standards, but made large sacrifices for "paths less taken" that didn't work out like I'd hoped. That included a prestigious PhD, which I did complete but was a grueling experience that ravaged my mental health (grad school can be absolutely brutal for this). Everything culminated between 35-40, a hard season of questioning the direction of my life, feeling restless and dissatisfied, and yearning for something I couldn't name.

You will find plenty of practical advice (such as about career changes), which may be helpful. Professional mental health care can also be important. But I'd also encourage you to take the "inner journey" aspect of this seriously. When we enter these listless seasons, it's often because our soul is alerting us to something in our life that isn't working for us... and thus offering us an opportunity to learn and grow. The darkness has a lot to teach if you do the inner work to slow down and listen to what it has to say. During these years I gained a lot of empathy and wisdom about life.

Passing through these seasons is a universal part of the human experience, and you'll find some wonderful guides. Some of my favorite resources include this article by David Brooks [0], "Finding Meaning in the Second Half of Life" by James Hollis, "Let Your Life Speak" by Parker Palmer, "Falling Upward" by Richard Rohr, "Crossing the Unknown Sea" by David Whyte, and "Reboot" by Jerry Colonna.

I also wrote a book about my own experience, titled "Eating Glass: The Inner Journey Through Failure and Renewal", designed to help others navigate these seasons. I have numerous free chapters here [1]. My main goal for the book is just to help others going through these seasons, so if you email me, I'll send you a free digital copy. I sincerely wish you luck finding your way through this season.

[0] https://www.nytimes.com/2019/04/06/opinion/sunday/moral-revo... [1] https://markdjacobsen.com/eating-glass/

Zotero and Obsidian is a killer combination.

If anyone is interested, I have some videos on research tools that include a Zotero->Zotfile/MDNotes->Obsidian workflow: https://www.youtube.com/playlist?list=PLHmevVAAXtu3_beDLtsTm....

I'm sorry you're going through this. I went through a dark night of the soul a few years ago amidst some professional setbacks. More recently, I've been on the edge of losing my 17-year marriage; we are still exploring whether reconciliation is possible.

The vulnerability, honesty, and goodwill in threads like this always warms my heart and bolsters my faith in humanity. I'll offer my own contribution. I wrote a deeply personal book called "Eating Glass" about navigating these seasons when everything seems to fall apart. I mention it from time to time on HN when I think it could be helpful, but today I'll just post the entire book for free: https://s3.us-west-1.amazonaws.com/com.markdjacobsen/Eating+.... My passion is just to help others walking similar journeys. Consider it a resource if it's helpful.

I wish you well on your own journey, and everyone else going through similar experiences.

I know your questions are practical, and you have not disclosed your emotional state, but I also know firsthand that shutting down a startup can be traumatic. Even as you address the practical issues, take care of yourself and do the inner work to process everything you have experienced.

I wrote a book titled "Eating Glass" specifically about the emotional journey through a failure like this [0] and put numerous chapters online for free [1]. My primary goal with the book is to help others, so I'd be happy to send you a free digital copy if that's of interest.

Good luck to you... you now possess valuable knowledge and wisdom to help you in your next venture and in life.

[0] https://www.amazon.com/Eating-Glass-Journey-Through-Failure-... [1] https://markdjacobsen.com/eating-glass/

See https://www.c4isrnet.com/air/2020/10/09/the-air-force-update...

Other thread: https://news.ycombinator.com/item?id=28407219

HN has two threads on this now. I just replied on the other but will copy here:

I can't speak for Chaillan, but as a military member who led an agile software development team similar to his during the same timeframe, I think he's referring to DoD's fondness for buzzwords.

Because "agile" is the new hotness, every DoD office and vendor tries to slap the language of agile onto a waterfall model. See this wonderful report from the Defense Innovation Board on "Detecting Agile BS": https://media.defense.gov/2018/Oct/09/2002049591/-1/-1/0/DIB...

I can't speak for Chaillan, but as a military member who led an agile software development team similar to his during the same timeframe, I think he's referring to DoD's fondness for buzzwords.

Because "agile" is the new hotness, every DoD office and vendor tries to slap the language of agile onto a waterfall model. See this wonderful report from the Defense Innovation Board on "Detecting Agile BS": https://media.defense.gov/2018/Oct/09/2002049591/-1/-1/0/DIB...

burnout often involves pouring too much of your heart and soul into something that does not love you back. I describe burnout now as a kind of "unrequited love."

I authored this comment but can't go back to edit. Given that this sentiment appeared to resonate with HN, I just want to add that I write extensively on this theme in my book "Eating Glass." I just put the chapter titled "Burnout" up for free: https://markdjacobsen.com/wp-content/uploads/2021/08/eg-samp...

This is a powerful piece that resonates with my own experience. I went through a period of severe burnout that took me a couple years to recover from. One of my later insights was that burnout doesn't merely entail working too much (although that's certainly part of it); burnout often involves pouring too much of your heart and soul into something that does not love you back. I describe burnout now as a kind of "unrequited love."

So many of us go above and beyond for our companies/projects/teams/whatever. The author here describes overcommitting at work. We might have the best of intentions, but at some point, we don't see the returns we yearned for and start to question what all this self-sacrificial giving is for. That is when burnout really sets in. I've had friends burn out while working for hostile or indifferent managers, startups that are trending the wrong direction, companies that engage in illegal or unethical behavior, etc.

A second insight was that burnout can play a positive role in our lives. It's like a circuit breaker that trips to protect us from a damaging situation. When we feel burnout coming on, it's a warning to pay attention to an important misalignment in our lives.

I'll echo others here; Obsidian is an amazing tool. For those who are curious about Obsidian, I recently created a YouTube video series for my graduate students titled "Tools for the Life of the Mind." [0] It covers some philosophical points about flow and focus, then dives into reading and note-taking and then covers a few tools like Evernote, Scrivener, Zotero, and Obsidian. Video 13 covers a workflow for migrating Zotero highlights and notes into Obsidian, which I found buried in the Obsidian forums. Completing this missing link has been a game-changer for my research workflow.

[0] https://www.youtube.com/playlist?list=PLHmevVAAXtu3_beDLtsTm...

This is good advice and absolutely true. I badly burned myself out with my first "startup" (a technical nonprofit) and needed a couple years to heal. I went into my second much wiser about boundaries and self-care and performed far better.

However, I think it's also important to recognize that burnout has many dimensions. Burnout is not necessarily the same thing as overworking.

In my book about entrepreneurial failure (Eating Glass: The Inner Journey Through Failure and Renewal [0]) I have a chapter on burnout. Here is an excerpt:

----

When you are passionate about a cause, you light up like a supernova. The energy crackles and flows. It powers you through obstacles that would make most people cower. Sheer love propels you onward.

That is where burnout begins.

The dictionary defines burnout as “exhaustion of physical or emotional strength or motivation usually as a result of prolonged stress or frustration.”

Yes, burnout entails exhaustion, but it signifies so much more. Burnout is really about unrequited love.

No matter how much you love your quest, it does not always love you back. Often the world does not align behind your glorious sense of purpose. Whenever some new twist or turn puts your goal further beyond reach, you must burn ever brighter to compensate. You seethe at the injustice. You choke back tears of disappointment. Despite all that, you do what you have always done, which is to hold it together through the sheer force of love.

Eventually, this misalignment between your passion and circumstances opens a wound in your soul.

---

I conclude, "You aren’t drained because you need more sleep; you suffer because you have a broken heart."

I write that burnout can function as a circuit breaker that protects us from further harm and alerts us that something is profoundly misaligned within our lives. Founders are uniquely susceptible because we pour our hearts and souls into efforts the world might reject or destroy.

[0] https://markdjacobsen.com/eating-glass/

Author here. I recently released a book titled "Eating Glass: The Inner Journey Through Failure and Renewal", which I wrote in the aftermath of a painful entrepreneurial failure. Nothing in my experience or reading prepared me for the brutal reality of that season. In our rush to celebrate failure, we often sanitize it, so honest accounts are rare. That can leave us struggling for guidance when we face soul-shattering experiences. I have since met many others--founders, creatives, or just ordinary people--who felt similarly lost when they had to weather life's storms. That led me to write the book I wish I'd had during that season.

I'm sharing with HN because it's my favorite community of creative, entrepreneurial people who also have thoughtful, serious, and real conversations about what it means to live well. I believe the book will resonate with popular HN themes about ambition, failure, resilience, work-life balance, midlife, and the spiritual quest to work out what constitutes a well-lived life. I have provided a large amount of free content (both written and audiobook excerpts) at www.markdjacobsen.com/eating-glass.

This excerpt from the Introduction gives a sense of my style and themes. Enjoy!

--

"Fail fast, fail often, fail forward." That is the mantra in Silicon Valley. We celebrate failure like Viking raiders toasting comrades fallen in glorious battle. We clank our frothy steins and hail their courage and honor. We weave epic tales of their battlefield prowess and the journeys of their immortal spirits to Valhalla. We yearn for a death half as good as our fallen heroes.

Any real warrior knows a battlefield death is not glorious. It is stupid mistakes, ill chance, screaming misery, urine and shit, fear and indignity. Dismembered youth strewn along the beach sob for their mothers.

We wrap battlefield death in legend not because it is so glorious, but because it is so terrible. We construct the legends, the myths, and the rituals so we can tame our own terror. Behind each of those gruff, bearded faces, a petrified child peers into the abyss of his own mortality. Will we have the courage to die so well? We clash our mugs, bellow at death, and applaud our own bravery.

Thanks! That’s largely what I was trying to write in opposition to. You find a lot of “here’s how I failed my way to success, and you can too” pieces. That’s not particularly helpful to someone who feels like their life is coming apart.

A few years ago, I presided over the failure of a nonprofit I'd founded. It was the most devastating experience of my life and involved all the emotions here: grief, anger, depression, self-blame, guilt, etc. I came to realize that this experience was fairly common for failed founders and business owners but almost NOBODY talked about it, and few people who hadn't been through the experience could understand.

If you'll permit me to self-promote a bit, I wrote a book out of the experience called "Eating Glass: The Inner Journey Through Failure and Renewal" to help others walk through this grief and healing season. Here is a link where I have a lot of free excerpts. [0] The chapters are broken down in topics like Burnout, Anger, Scars, Aftershocks, Health, Perspective, Courage, etc.

Here are a few lines touching on grief and the relentless drive to save a failing effort:

"Burnout is really about unrequited love. No matter how much you love your quest, it does not always love you back. Often the world does not align behind your glorious sense of purpose. Whenever some new twist or turn puts your goal further beyond reach, you must burn ever brighter to compensate. You seethe at the injustice. You choke back tears of disappointment. Despite all that, you do what you have always done, which is to hold it together through the sheer force of love. Eventually, this misalignment between your passion and circumstances opens a wound in your soul."

[0] https://markdjacobsen.com/eating-glass/

If you're looking for good climbing autobiographies, try Tommy Caldwell's "Push" or Dierdre Wolownick's "The Sharp End of Life." Caldwell's book is well-written and shows deep insight, perhaps due to the severe hardship he experienced. If you liked "The Dawn Wall" (one of my favorite films), you'll like the book.

Wolownick's book might be my favorite climbing memoir. Wolownick is Alex Honnold's mother, but she's not cashing in on his success; this is her own story about finally embracing her own life after years of self-sacrifice in an unhappy marriage. She is a writer first and foremost, and she tells a beautiful story about life. The climbing scenes are gripping and relatable because she is such an ordinary person--which makes her accomplishments all the more extraordinary.

I recently spoke with someone from Alpha Bridge Ventures (https://www.alphabridge.vc) after writing a book about entrepreneur mental health. They provide mental health services to their founders, and my understanding is that they have a firewall between the investors and a separate entity that provides mental health services. A menu of mental health services is available to founders but the investors never know which founders are using them. Although they emphasize the intrinsic humanitarian value in helping their founders, they also rationalize their approach by noting that providing mental health services is good business; founder burnout is a leading risk factor for startup failure. I was impressed by their approach, which seems to mitigate the incentive problem.

Your comment reminded me of research by Eva de Mol, Jeff Pollack, and Violet T. Ho that resonated with me.[0] They studied "destiny beliefs" as an explanatory variable for entrepreneur burnout. Those words perfectly captured what I felt when I started my nonprofit (now failed). It was as if the heavens opened, and I was divinely appointed for the task. That gave me incredible energy but made for a devastating fall. These days I try to carry my expectations more lightly.

[0] https://hbr.org/2018/04/what-makes-entrepreneurs-burn-out

I'm a two-time failed founder. The first was a humanitarian drone nonprofit, and the second was a software development team internal to government. The first failure absolutely wrecked me. Your comment resonated because nothing prepared me for the unique experiences and traumas of presiding over a startup failure. I truly felt like I was on my own, trying to navigate the prolonged journey through failure, healing, and renewal.

I ended up writing a book to help other failed founders, titled "Eating Glass: The Inner Journey Through Failure and Renewal." Book here [0] and 60-pg sample here [1]. I plan to share it via "Show HN" soon, but given your plea for resources, I'd love to send you a free digital copy. Just send me an email address at mark@markdjacobsen.com. My passion with this book is really just to help other failed founders on their journeys.

[0] https://www.amazon.com/Eating-Glass-Journey-Through-Failure/... [1] https://markdjacobsen.com/wp-content/uploads/2021/03/Eating-...