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A reflection upon some failures and mistakes

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I had plans, and it’s felt like at this moment in time, most of them are failing/have failed. Here’s a list, and if you see yourself as one of the affected persons, please know I am genuinely sorry!

Of all that has gone wrong, some feels very avoidable, some feels very unavoidable, and some is unknown. In many cases, especially when my “inner critic” is running the show, it feels like I’m completely to blame, and I feel big senses of guilt and having failed other people in really meaningful ways.

I know that not all of these are completely my fault, and our failures don’t define us, and it’s okay to make mistakes

The worst is when it feels like my efforts to help literally make things much worse. Or, through sheer callousness or cluelessness, I cause someone else real inconvenience and harm.

I’m getting a bit expansive here - these don’t all cause me equal pain (thank god) and some of these failures might be a bit tongue in cheek. Levity helps when things hurt.

A long list of ways I’ve failed #

As another aside: it’s cathartic to get things on paper.

I might very well be overly self-centered, but I’ve historically been comfortable ‘exposing inner state’, and in a desire to rebuild a sense of a coherent narrative of my own life, especially one that makes sense to others, listing the highlights of failures is helpful. I often feel an intense desire to be able to explain some of this to others, especially in a way that is generous to me. (The written word, my own website, across the time and rounds of editing afforded by this format)

my marriage #

I feel that I really, really failed people I wanted to do nothing but love really well.

Kristi, and Kristi’s family. Eden, in some ways.

Kristi and I are rapidly moving towards a divorce. The ‘failure’ of our marriage is rooted in the intersection of many factors. Some within our control, some not within our control.

The last few years have been difficult.

Basically, the abandonment/emotional neglect that we both experienced as children began to be replayed in our marriage, for a variety of reasons, with 2020 being a year of particularly visible escalation of harmful trends, overlapping with very difficult circumstances and life events. We wrestled with death, disease, injury, Covid, etc. There were communication breakdowns, and mismatches of hopes, desires, and goals.

I observed signs of things not going well in myself, like feeling despondent and suicidal, deep in a pit of despair. I’ve learned a lot about emotional self-regulation, boundaries, co-dependency, and more, though it’s been unfun. It’s looking like introducing separation and space is the quickest path to us both being happy and healthy and being able to thrive.

648 Iowa St (the house across the street) #

My god. Lets talk about this.

I ended up “buying” a family out of getting evicted, and purchased an option (literally, in the financial sense) on the property, hoping to do “something interesting”, because they didn’t have any options for where to go. I committed to making the rent gap that was filled by some departing tenants (as the most “problematic” tenants left, the legal/municipal problems leading to the landlord wanting to get rid of the property were going away).

My LinkedIn bio says “software developer”, which is politely synonymous for “rich”. I have been, emphatically, not rich before in my life, and even earning “only” the $132k/yr that I do now feels like a crazy amount of money in many ways, though the current global trends in housing and inflation temper the fun a bit. And yes, I know it’s possible to earn dramatically more. More on that below.

Unfortunatly, I was not a W-2 earner at the time, when I started this project, but had just received two job offers that came in at $120k and much more. I was on the cusp of landing very interesting and lucrative consulting work, so I felt OK committing to the opportunity, but should have either taken a stable job and committed to helping in this way, or not taken the stable job and not committed to helping in this way.

See, I’m deeply interested in the ‘dynamics’ of how cities work, and totally saw the events as just another instance of an oppressive system chewing through all the involved parties to destructive ends. I had/have been thinking often on the implications of the things Jesus said and did, especially around ‘loving money’ and ‘helping others’.

I jumped in, halted the eviction, and then… failed to do anything of note, other than spinning wheels for the better part of a year.

I believe that, in general, if people take steps to care for their immediate family and immediate neighbors, that is the right thing to do, on many levels.


A lot of things went wrong, support that I’d subconsciously came to expect dried up, and my own co-dependent need to support others to make them like me all ended up making me feel like I was sprinting repeatedly into a brick wall.

I had regularly found my ability to focus at work severely diminished, and the pleasure I once took from many day-to-day activities was completely gone. I often felt unlovable, broken, deeply flawed, perhaps so foolish and coercively convincing that I was a dangerous threat to others, and I feared never being in a loving relationship again.

My daughter Eden is deeply important to me. I plan on being an available and present father, and loving her as well as I can love anyone. I am quite sad over the state of some aspects of my life, but I can see a path to things being better.

A long sabbatical to try to ‘start something’ #

I quit my last full-time job as Covid was breaking out. I’d had a bunch of plans for what the sabbatical would look like, none of them worked out, and I failed to re-build good plans.

I kept floating along on the path of least resistance, and trying and failing to make certain things work.

I gave Turing a proposal to work hard on their ruby-exercises repositories, to help students self-serve into a higher degree of readiness for the program. Early results for the free work I’d done for them, and the paid work I did for them, was extremely promising. For a variety of reasons, it didn’t work out, and in a way that hurt. Either I keep getting myself involved with unhealthy organizations, or I have this massive blind spot to how I come off to others, and keep stepping on toes in a really visible and obvious way, like walking around with toilet paper trailing from your shoe.

After Turing, I kept trying other projects. I learned a ton, and I’m willing to throw myself into nearly anything, but I kept not hitting a sustainable mix of “getting paid enough and regularly” and “doing reasonable amounts of sales work to get new clients”.

For a variety of reasons, I felt my hope and optimism and confidence and sense of joy and playfulness being slowly falling through my grasp. As failure/success got laden with conditional approval (and shame) from others, because I wasn’t able to recognize it as such, I just kept sliding, and toiling away from a position of sadness, depression, and loneliness.

I regularly had to pivot from being having very difficult conversations with intimates, to hopping on a video call with an executive or CTO of a software company, wiping tears off my face as the zoom call started. My mental wellbeing was diminished, repeatedly, by many hard words and lack of repair.

Part of why I am writing this all publicly is so that one day, if Eden cares to try to understand what happened to her parent’s relationship, I can have my side of the story recorded. I’ve already decided that I will not kill myself, so when I think through the recent times where I was being treated so poorly that suicide looked like a desirable outcome, I slowly warmed to the idea that it would be better to end the relationship than kill myself.

I have a sensitive and tender heart, and am driven by beauty, joy, a desire for growth and improvement and building beautiful things, especially that will last for a long time. I desire to spend my time and energy in those generative domains, with anyone who’s there, voluntarily participating alongside.

I am so sad about the many dreams that I thought we were close to achieving, in purchasing the house we moved into. My growing despair and depression and confidence in my own inadequacy and danger to others set me on self-sabotaging paths, like withdrawing from most of the people in my life, in an unhealthy way.

I feel like my life has been burned to the ground. The emotional abandonment I’ve felt for the last few years has been absolutely devastating.

A house and investing in the community #

We bought an old, crappy house (from 1955) with tons of old house problems. I’d hoped Kristi and I were going to work on it together, playing music, hanging out, enjoying togetherness, while working on something important to our family and each other.

I kept being caught by surprise, as my expectations proved to be wrong. I shed many more tears over the last two years than I’d ever expected.

I eventually ended up feeling simultaneously useless, incompetent, unlikable, unworthy to be helped, and devoid of interesting or beautiful visions for the future. Eventually I had to realize this cannot all be true, and started taking steps to not feel these things so strongly.

I’ve failed in the aspects of the house I was most excited about (a backyard garden, hosting friends, parties, playing games, reading books with friends and loved ones in the morning on our back porch, composting toilets). I allowed a patina of shame to grow over my interestes and desires, and that led to me feeling like I needed to ‘hide’ these interests from my community, and I ended up masking (poorly) my idiosyncratic tendencies.

I’ve failed with the house, and with what I’d wanted to do in the community.

I’ll need to add a reference to The Politics of Jesus, because I was strongly motivated to spend real wealth on things that mattered. So I put real money into this effort.

Over $16,000.

I’d hoped to get tons of great stuff out of it, I saw ways I could be successful, but at this point I’m chalking it up as a failure.

Where I’d hoped for partnership, I’ve found something else. It’s been hard, expensive, and time-consuming. This project neither the first nor the largest loss. I’ve now also now spent (or wasted) over $10k on therapy, weeks of PTO, and am aware that the opportunity cost of relationship difficulties is staggering.

I withdrew from, and abandoned, many friendships and relationships #

There’s this phenomena where someone with an insufficiently developed sense of self, coupled with unhealthy coping mechanisms, when faced with a sufficiently hostile presence from loved ones, internalizes their abandonment of him/her into “self-abandonment”.

That leads to depression, withdrawal, shame, a visceral sense of being wrong, broken, unfit, unlovable. I’ve felt this deeply for a long time. I saw a friend for the first time in a while, and I mentioned casually (as I will casually mention to anyone who asks) that I’d been severely depressed for a while, and he was shocked. He said “You? You don’t seem prone to depression at all, and the Josh I remember was vibrant, full of life, relationally-oriented, and eager to engage with the world.”

This was a kindness to me, as that version of myself seems so long gone I barely remember it ever having happened. I recognize intellectually that it was the case, but I cannot get there emotionally. I hope to rebuild my sense of self someday, but it’ll take a while.

In the midst of all this difficulty, especially because of the sense of shame that I’ve found myself adopting, I’d not tell others what was going on. After all, if someone says “how’s it going”, and the moment I say anything true, I break down in tears, and I fear being met with rejection or scorn or shame if I earnestly share my emotional state with others. I found it easier to simply let phone calls go unanswered, emails to go unresponded to, texts go unresponded to.