all posts tagged 'unemployment'

The Job Hunt Chronicles: Month 2: Beyond the Fog

originally shared here on

A pair of worn-out shoes at the edge of a path leading into a misty forest.

(This is the second in a series of posts going through my journal entries from the last month and talking about what it's like to go through a period of unemployment, self doubt, and finding your spark. You can read the first one here.)

Alright, we've made it through February!

I'm still on the job hunt. I'm still dealing with some crippling anxiety and depression.

But I'm making progress! I'm having interviews, I'm figuring out how to feel my feelings and articulate my values, and I'm finding opportunities to enjoy the moment and be optimistic about finding my next job.

I journaled every single day last month. I fed all 28,000+ words into ChatGPT and asked it to summarize the entries into two sentences using the style of the journal entries themselves. Here's what it said:

Another month down, filled with musings, mild misadventures, and moments of clarity amidst the mundane. Balancing personal passions, family love, and the hunt for professional fulfillment, the journey meanders through the highs and lows, always circling back to the comforting, complex tapestry of daily life.

Man, do I actually sound that pretentious in my own journal? 😂

Anyway, if you're wondering what was on my mind in January, strap yourself in and let's go!

"What are you looking for?"

Gonna put this up front again like I did last month.

I'm looking for a position where I can blend strategic tech leadership with hands-on coding, preferably in a small, mission-driven company focused on healthcare or climate solutions. The ideal environment is a funded startup with fewer than 50 employees, leveraging generative AI, and based in or flexible with the Twin Cities area.

Ideal extras include a flexible 32-hour work week, a hybrid work arrangement, and opportunities for travel and professional development

In short: If you know a mission-oriented startup seeking a tech-savvy strategist passionate about making a significant impact, send them my way!

Activities I've done

I put this section in my last post because it felt like a badge of honor to brag about how many meetings I had in a month. To me, it felt like I was doing something.

All of that pride went down the drain after talking with a new friend who basically said that I'm continuing to burn myself out by grinding through hundreds of meetings instead of doing the actual hard work of sitting down and figuring out what my values are.

Once you know what your values are, you are so much more likely to know what path to walk down.

So in that spirit, I won't mention how many meetings I've had. Instead, I basically spent this month continuing to figure out who I am and what I want.

I'm aware that's not a very satisfying or flashy statement to make in a blog post that purports to explain life in the eyes of someone who got laid off.

But truly, most of what I've done in the last month is learn about my feelings and how to deal with them productively.

I've gone to some of the darkest places I've ever gone in my life this past month. The shame, the fear, the depression, the embarrassment, the anger... all of those feelings are easy to deal with when you ignore them like I had been for my entire adult life.

But your body can only handle ignoring them for so long. Eventually, you find yourself leaving work early and rushing to the hospital because your heartbeat is noticeably irregular, and your heart feels like an orange being crushed in the hands of a strongman, adrenaline secreting between their fingers.

One thousand and six hundred dollars later, you're told that there's nothing physically wrong with you. Go see a therapist.

Your body remembers each and every time you ignore those feelings, those warning signs. Those "gut checks" that you decide to push aside because it doesn't align with what you think you should be doing.

Eventually, it all boils over.

So that's what I've been up to this month: looking back at the past twenty years of my life and beating myself up for years of beating myself up.

It hasn't all been atonement, though. I've also started to hope again. I've had moments where I'm excited again for what's next.

Even if that's something as simple as waiting for a hug from my kids when they get home from school, or watching an episode of Drag Race with my wife every Friday.

Those little things are the things that keep me going, and they're giving me the energy to start looking forward to how I can get back out in the world and be helpful.

Things I've learned

Here are all the random things I've been contemplating over the past month:

👨‍🎨 Personal growth insights

My 7 year old daughter told us she thinks she's getting too old for Barbie.

This was crushing for me and my wife to hear, but for different reasons.

For my wife, it was the prototypical "my kid is growing up" response that all parents feel when they see their kid age. I don't wanna minimize that feeling, because I certainly feel it myself: it's bittersweet to see your kids grow up.

But for me, it was a good reminder that the grass is always greener on the other side.

I can't remember the last time I dreamed about what I wanted. I feel like I've been coasting for at least the last several years.

Besides hanging with my family/friends and the occasional fun project at work, there hasn't been much driving me forward to grow.

And that's probably where a good chunk of my depression is coming from.

I could either sit and analyze the "why" (and trust me when I say that I have), but the more important thing is to be grateful for coming to this realization and making strides towards dreaming again.

My problem is that I, uh, kind of forgot how to do that.

Part of it stems from my engineering brain continually looking for edge cases that cause me to reject a dream wholesale.

Another big part of it might be this fear of losing what I've already got. I worked hard to build a reputation, I've got a great family that needs to be provided for, I've got a house that needs maintenance and improvements, the list goes on and on.

But whatever the reason, I find that dreaming is a muscle that can atrophy. I have a similar theory about being extroverted: after the pandemic, I found being around people to be exhausting in a way that I never felt before. My extroversion tendencies returned as I continually subjected myself to new groups of people.

Dreaming feels the same way: continually practicing and refining the act of dreaming is the only way to get good at it.

That's what makes me jealous of my daughter and son.

I watch them play with Barbies together, and their ability to play baffles me.

How can you just start playing?

How can you come up with new scenarios and then go for it?

I ended up talking to my daughter about this. It felt great to share with her how I'm jealous of her ability to be young and idealistic and have a vision for how her life can be, and I'm jealous of how she's able to express that vision through her play.

She ended up deciding to keep her Barbies, and I'm extremely grateful for that. It means there's still more time for me to learn first hand from the master of dreaming.

She'lo yada, yada.

I was speaking with someone about struggling to make a decision that needed to be made, and he told me about this expression that he heard his family say a lot growing up.

It's a Hebrew expression that means "He who doesn't know, knows."

This pairs nicely with the Derek Sivers axiom of "Hell Yes, or No," where something is either impossible to say no to, or you simply say no to it.

Both of these, of course, are "easier said than done" aphorisms to adopt, but it's good to document them nonetheless.

It's awesome to end things.

I spoke with a friend who ran a very popular blog about his adventures traveling to various breweries, and we were both talking about how we were considering winding down our various beer-related projects.

Throughout my entrepreneurial journey, I keep coming across articles expressing the importance to consider the ending to whatever you start.

At one networking event, I heard a speaker ask "what is the percentage likelihood that you will exit your business?"

The answer: 100%.

Because at some point, you will die.

That is the ultimate finality, of course, but the longer I'm around here on earth, the more I have to start embracing the good side of things ending.

I built mncraft.beer a decade ago because my wife and I were extremely passionate about supporting craft breweries, and we had a goal to get to every single brewery in the state.

Fast forward ten years, our ambitions have changed. It's difficult to convince two young kids to sit in a car for several hours on a weekend, let alone motivate myself to spend all that time traveling to visit a brewery that, in all likelihood, only produces mediocre beer.

I've gotten all that I can get out of that project. My biggest takeaway is that a brewery often is a boon for a small town. Even if the beer isn't going to win any awards, we all collectively need more third spaces, and breweries act as a fantastic gathering place for a community.

According to my Untappd account, I've had 7,445 beers since joining the app in August of 2012. Of that, 4,346 of them were unique. I've had 200 different styles of beers, and I've learned that I like Pilsners, Belgians (anywhere from Dubbels to Quads), Extra Special Bitters, Kölsch beers, and straight up, old school IPAs.

I know what good beer tastes like, and I know what breweries make good beers in our state.

So what's the benefit to continuing that app?

I shared a video from Hank Green last year about letting go of the dreams of your past in order to free yourself up for new ones, and that's the mindset I gotta adopt here.

It's always sad to end things. I remember every closing circle after a show would end in theatre was a mess of emotions and tears. I remember losing our final football game in high school, looking around the field, seeing tears and frustrations mount on the faces of my teammates. You never wanna say goodbye to something that gave you so much joy.

It kind of reminds me of this exchange from Hook (one of my favorite movies of all time):1

Hook: Are you ready to die, boy?

Peter: To die would be a great adventure.

Killing off parts of our former self on which we linger is a privilege which allows us to fully move on to the next adventure.

Al Snow on Success

I felt under the weather this month for a couple days, and on one of those days, I decided to watch the Wrestlers documentary on Netflix.

Two things I want to mention about that:

First, the whole thing felt like a work-shoot to me. I love the way professional wrestling blurs the line between what's real and what's made up.

It felt like the documentarians were very intentional about painting Al as the babyface (the good guy) and Matt Jones as the heel (the bad guy).

I hope OVW gets a good boost in viewership as a result of the documentary. They did a great job of showing how the sauce gets made, and I'm sure they know it's the exact sort of thing that hooks in smart marks like me.

Second, since I assume all of those wrestling terms are not meaningful to most of you, here's a great quote that comes at the end of the documentary:

If you equate success in a destination (that destination being WWE), you’re probably not gonna get it. But if you equate success in doing something you’re passionate about and that you love, and that gives you purpose and drive, then you’re successful.

I keep asking myself what success means to me, and while I don't have a solid answer yet, maybe it's because I'm still working on giving myself permission to dream without restrictions.

I'll get there soon, though. I can feel it.

Tracy Chapman's "Fast Car".

After Tracy performed with Luke Combs at the Grammy's this year, I saw a post that talked about her performance of Fast Car in front of an extremely frustrated crowd at Wembley Stadium in 1988.

You can find recaps of the story online, but the long and short of it is that Stevie Wonder was refusing to go on stage at this birthday celebration for Nelson Mandela, so Tracy came back out on stage and performed Fast Car.

When you watch the video, you hear the crowd go from rowdy to genuinely moved.

It's hauntingly beautiful. That song has always been a staple in my rotation, and after hearing it performed in this way, it makes it even more special.

We should use all of our senses to find our way.

I feel like the best metaphor I can give for how depression feels to me is a fog that completely obstructs my vision.

No matter which direction I look, all I see is a dense fog of nothingness.

But what I keep reminding myself is that even when you can't see, you still have at least four other senses you can use.

I'm not sure how to use those other senses yet, but I'm starting to use my ears to listen for opportunities, my nose to sniff out which direction to walk in, and my gut to validate which direction feels right.

The Dan Patch Club serves as a template for who I wanna be when I get old.

My dad invited me to speak to The Dan Patch Club, which is a subgroup of residents and friends of the Masonic Home in Bloomington dedicated to learning and exploring various topics together.

I'm ashamed to admit that I'm not immune from playing the generational blame game. But placing each other into broad, faceless groups like "boomers" or "millennials" only makes it harder for us to pool our collective wisdom and work together to solve real problems that our society faces.

Short of vague jokes about mysticism and ritualistic masonic secrets, I honestly had no idea what to expect when my dad asked me to come speak to these Masons.

I figured the hour would be spent giving a broad introduction to generative AI tools like ChatGPT and Midjourney, but what surprised me was how many hands were raised when I asked "how many of you have used ChatGPT?"

I should've known better because I did know that this room contained two PhDs and a retired attorney. All of these guys had extremely poignant and informed questions about the use of AI in our society.

We talked about the legal implications of deep fakes, the ability to spread election propaganda at unfathomable speed, how these models "reason" and come up with "truth", and the most important question which continues to plague us information workers: "how do you turn off predictive autocomplete in Microsoft Word?"

As we were wrapping up, I actually didn’t want it to end in the same way I haven’t wanted many of my conversations to end lately.

Sparking that curiosity in people is one of the key values I've been aspiring towards as I craft my vision for the next ten years.

I hope when I’m their age, I’m still kickin’ it with my homies, whomever they may be, nerding it up about complex topics, continuing to challenge myself and grow as much as possible.

Is anxiety only reducible when you are focused on your basal instincts and needs?

It seems like the only known treatments and mitigations for anxiety center around mindfulness and getting your brain to live in the present.

Is that really it? Living in the now is the only way to make anxiety go away?

It seems like there should be more we can do to harness our ability to look into the future while keeping the major doom scenarios from spiraling in our heads.

Meditation?

Anyone have any good suggestions for developing a consistant medication practice?

I have tried apps in the past but haven't found them to be sticky or altogether helpful.

Daniel Tiger isn't only for kids.

Toward the end of February, I had a major backslide with my mental health, and it kind of came to a head one day while I was dropping my son off at daycare.

I usually let him pick out what we listen to, and he chose the Daniel Tiger's Big Feelings album.

One of the first songs on that album is called "Close Your Eyes and Think of Something Happy."

I ended up at a red light and, as I found myself descending into some negative thoughts, I decided to do exactly that.

And you know what I saw?

Absolutely nothing.

It crushed me.

I'm a grown ass man, and I couldn't even come up with a single thing in that moment to think of in order to make me happy.

Suddenly, from the back seat, I hear my boy giggling and singing along.

Man.

That moment highlighted to me how badly I needed help through this stuff. That there is a ton to be happy about.

I'm glad my son was able to help me get out of my head.

And I'm glad I'm no longer dismissing those songs as "simple kid songs." We can all use a reminder for how to process sad and angry feelings in a healthy manner.

It's easier to venture out when you know you can return home.

I heard Dr. Becky mention it in that Farnam Street podcast, but she was talking about the relationship between teenagers and parents.

I've been considering the sentiment in regards to music.

For the past five years, I've been very curious about genres of music from which I've typically shied away.

I decided to listen through my entire local library of music, which is currently sitting at 83 days of non-stop new tunes.

That library is filled with music of every type of genre imaginable. Country. Experimental free jazz. 70s East African jams. Norwegian death metal. A mashup of Metallica and The Beatles. All kinds of EDM mixes.

It took more than 4 years to get through all of it, but I finished it with an appreciation of the core albums that have been there for me my whole life.

The other day, I decided to shuffle my "key albums", which is any album I've given a star rating of 4.5 or higher.

I was instantly transported back to several happy moments in my life. Building Ralph Wiggum images in front of my computer in my childhood bedroom. Walking home to my (eventually) condemned house in college. Going for a run around the pond in Bloomington. Riding the light rail home.

Solitary moments where I didn't need to worry about what other people would think of what I was listening to.

A place where I can be myself.

That concept applies to much of our soul searching. We are only able to be truly adventurous when we know there's a safe place for us to come home to when we're weary from exploration.

I find myself drawn to people who are able to speak passionately about their cause much in the same way my kids talk about Santa Claus or the Easter Bunny.

There's something magical about believing in something.

There's something special about having solid, firm convictions on which you stand.

It's this palpable energy you can feel emanating from someone sharing their passions.

I felt it at a couple of job interviews I had last month.

I felt it while speaking with friends about AI.

I felt it playing crazy rummy with my wife and talking about what we want to do for our ten year anniversary.

Maybe that's the feeling I should be chasing. Is that feeling "joy"?

I'm not sure where I started getting so disillusioned about that feeling in a professional context.

But I'm eager to find a job where I can surround myself with that energy once again.

Kids simply do not care about success like grown ups do.

When my daughter was 4, I'd watch her play a game where she'd have to pick the right word and she would purposefully pick the wrong one.

Like, I knew she knew the right word, but she intentionally picked the wrong one.

It sent me up a wall.

But one day, I asked her why she was picking the wrong one on purpose.

She said, "I like the noise it makes when I get it wrong."

My kids are way better at learning and dealing with uncertainty than I am.

And success is whatever you define it to be.

I can't thank you all enough.

A lot of my journaling over the past month is just, like, truly dismal.

But there are moments of light, and they're all thanks to you all.

I am forever indebted to the literal hundreds of people who have reached out to ask me how I'm doing. I'm so fortunate that I've got so many people who care about me.

I feel like I'm not able to be my own best friend right now. I find myself continually returning to a place where I can't stop beating myself up.

You know how people used to take their old cars that they don't want anymore and drive them deep into the woods and leave them there? That's how I feel right now. I feel like a beat up old car that's completely rusted through, nature slowly consuming and reclaiming it.

But it's conversations with many of you that are helping me see that's not an accurate picture of reality.

So thanks for checking in on me. It's definitely helping me get through the fog.

👨‍💼 Professional growth insights

If someone calls themselves an "expert", it's because they're trying to sell you something.

This insight came from a talk by the incredible Jim Wilt that technically came from January, but I didn't include it in last month's post and want to make sure I include it now.

My inbox is a prime source of stress.

It's a roulette wheel where sometimes you win big (a job offer, a congratulatory email, a rave review), but you also sometimes lose big (a threat of a lawsuit, a late bill notice).

I'm still learning how to separate work from my personal life, but a good place to start is to go to your settings on your phone and turn the inbox off for your work email.

You don't need to remove it altogether.

But when I was at Bionic Giant, I turned it off, and it helped my stress levels immensely at night.

It allowed me to turn it on if I needed access to a message on my phone during the day, but then I could easily turn it off at night so I didn't get distracted when I went to my inbox to read a newsletter.

It's awfully hard to say "no."

I wrote a lot in my journal this month about how a lot of my anxiety stems from saying "yes" to everyone and everything.

One reason I can't say "no" is because I'm not sure what I actually want. Saying "yes" at least gives me the chance to figure out if it's something I want.

But when I say "yes" to too many things, I never get a chance to sit back and reflect on whether it was something I wanted.

Which basically describes the first decade+ of my professional career. I say "yes" to the point where I have no room in my schedule to reflect.

I need a better analogy for how generative AI arrives at its solutions when compared to a search engine.

If anyone has any ideas, let me know.

I don't get why I feel so guilty for feeling sick.

I find it next to impossible to rest as it is.

But when I'm sick, it's like my anxiety works in overdrive to try and let me know that I'm falling behind on stuff.

I said this earlier, but I felt a little under the weather one day this past month, and I ended up calling folks and cancelling my meetings with them. The guilt I felt was incredible.

I appreciate having anxiety to keep me thinking through possible problems and pushing myself to move forward to fix them, but the combination of the "fight or flight" and "freeze" responses makes it tough to get anything done.

Learning new things becomes a lot harder as you age.

I was turned down from a job I was rather hopeful to get because I don't have the experience in the Javascript framework that they were looking for.

So I decided I was gonna sit down this past week and learn it.

I tell you, I watched three different tutorials, and I could not bring myself to finishing any of them.

The problem here is that I already know how to build web apps. I've been doing it since I was eight years old.

I've learned how to build web apps by hand, by using PHP, by using Laravel (a framework built using PHP), by using Wordpress, and by using Ruby on Rails.

And you know what I've realized after all that learning? They're all slightly different ways of achieving the same thing.

And guess what? There are roughly a dozen different additional popular ways to build and deploy web apps. There's all kinds of containerization techniques to deploy scalable platforms. There are cloud providers that allow you to spin up all sorts of architectures to scale your platform. There are a bajillion different Javascript frameworks to write your code in, along with a quadrillion CSS frameworks to style your apps in.

I may have hit my Morgan Freeman in Shawshank moment where I simply don't care what technology we use anymore.

You feel compelled to use Rails to build a monolith? Great!

You think you're gonna hit a scale that requires a complex microservice infrastructure built on hundreds of lambdas? Fine, sure, let's do it.

The thing is, I don't want to learn a new framework for the sake of learning a new framework.

If I needed to figure out a specific architecture for a job, I am 100% confident that I could do it, even if it requires using a framework that I've never used. That's what nearly 30 years of building on the internet does for me.

[...]

Can I be real with you all for a minute?

Of all the sections I've written in this blog post, this one is the one I am having the hardest time releasing to the world.

I have a feeling I'm coming off as a bit of a crybaby.

I recognize that any craftsperson needs to hone their craft and stay up to date with the latest tooling in order to be marketable.

My problem may be that I'm conflating burnout symptoms with my general interest in learning new things.

In every development project I've ever worked on, I've had to learn new things.

There's always a new API, a new SDK, a new framework to pick up.

It's been part of my agency life for my entire career.

Maybe my problem isn't with learning new things. Maybe it's that I'm exhausted from having to whip around from tech to tech without ever taking an opportunity to go deep on any one of them in particular.

Even as a seasoned Ruby on Rails developer with more than a decade of use, I feel like I'm falling behind with all the fancy new Rails 7 functionalities like serving HTML over the wire.

There are a million different ways to build websites, and I'm struck with the realizing that I'll never learn all of them.

Maybe I have to decide whether I want to sharpen the tools I do know intimately, or whether now is a time to adopt new tools and put in the work to become an expert with those ones.

They say learning new things becomes harder as you get older.

What's next for me

Last month, I committed to coming back with a more clear vision of what I want my life to be. I don't think I'm at a point where I'm ready to articulate my vision, so I am going to continue spending time honing that through journaling, meditation, and conversation. I hope to be in a place to share a rough draft with y'all next month.

I also want to keep up my recent blitz of sharing links here on my blog. I'm going to add in a "tagging" feature to my posts so I can start keeping better track of things I talk about on here and find them more easily.

I also want to start podcasting again. I will commit that by next month, I'll be able to tell you what my new podcast will be about. My friend Dana and I are going to start meeting once a week to hold each other accountable on our various endeavors, and that's what I'll be spending that time plotting.

If you're reading this and want to know how you can help me, here's how:

  1. If you know of a full time (32-40 hr/week) job opportunity where I can help architect a complex software system for a meaningful organization and lead a team of people to get it built, please send it my way.
  2. If you come across any thought leaders who are speaking about AI from a perspective of what it will mean for our humanity (in how we work, how we organize, how we think, etc.), please connect them with me!

Thanks again for reading all the way to the end! If you did, I would love to hear if anything resonated with you. Shoot me an email or a note on LinkedIn.


  1. The next line in this exchange is, ironically, "Death is the only adventure you have left," which I don't feel fits neatly into my narrative here, but it's still a great movie. I can't wait for my kids to be old enough to enjoy it like I still do. 


Your Job Will Never Love You Back


🔗 a linked post to cupalo.substack.com » — originally shared here on

Upon returning from her lunch, my boss asked me to prep one more term packet.

“That poor soul,” I thought as I made my way to the HR supply closet to assemble another fateful folder.

I exited the supply closet, packet in hand, and walked over to my boss’s office in which she and the other HR manager were chatting. As was often the case.

Extending my arm, I reached across my manager’s desk to hand her the freshly prepped term kit. Her hands remained still. Folded on top of her desk.

“You can actually keep that one. That one is for you.”

This is cruelty on another level.

The main reason I’m sharing this is the suggestions Lauren makes after her layoff to find yourself outside of your profession.

It’s a big part of how I’ve spent the last two months since I got laid off. It’s really hard to undo not only 12 years of professional conditioning around the notion that “I am my job”, but also the 16 years of schooling before that which trains you to believe that other people will only value you for your profession.

In one of the job interviews I had this week, someone asked me, “how have you been spending the last two months?”

The only answer I could give was the honest one: “I’ve spent it dealing with my anxiety and depression.”

And while I can’t say I’ve beaten that stuff, things are definitely better. I also can say I’ve been enjoying playing with my kids, dating my wife, learning about AI, hanging out with likeminded nerds exploring AI, playing with new web development frameworks, making music in a band, catching up on TV, finding new ways to exercise (kickboxing and HIIT), and exploring philosophy.

It would be nice to have money coming in the door (and it would be doubly nice to have health insurance to help pay for therapy 😂), but I’m extremely grateful for the opportunity to figure out who I am again.

(For the record, my layoff story isn’t that dramatic. Layoffs are never easy for either side of the table, but they certainly don’t need to be made cruel.)

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The Job Hunt Chronicles: Month 1: Discovering My Path

originally shared here on

An AI-generated image showing some business guy standing at a crossroads, looking at a wide array of paths and opportunities floating in the sky.

I was laid off from my job on January 2. It did come as a bit of a shock, and for the first time in my life, I've been really struggling to figure out who I am and what I'm looking for.

As a way to keep pushing myself forward and holding myself accountable, I'm going to start publicly documenting this process as a way to process my thoughts out loud, keep my friends and network aware of my activities, and start some conversations that'll help me take my next step forward.

"What are you looking for?"

If I could summarize the past month in a single question, that would be it.

In the 58 conversations I've had in the past month with friends, recruiters, industry peers, networking events, partners, and job interviewers, I've been asked that question literally every single time.

And 58 times later, I think I'm starting to get closer to an answer.

Here's what I'm looking for:

  1. A team of kind, smart, and hard-working people
  2. A mission that the team rallies around which helps improve as many lives as possible
  3. A leadership role to help drive an engineering team towards fulfilling that mission
  4. Doing all of this while continuing to experiment with LLMs and other AI technologies
  5. Connecting with as many people as possible to explore the impact of AI on who we are as humans
  6. Something that includes medical benefits to support my family

It doesn't matter much to me what the title is. Some roles I've applied and begun interviewing for include "Director of Engineering," "Software Architect," "AI/ML Lead," and "Founding Engineer".

If you know of any opportunities that you think would fit a nerdy kid who has a big heart and enjoys exploring practical applications of artificial intelligence, please send them my way!

Activities I've done

Here's a list of the activities I've pursued between January 2 (the day I got laid off) and February 3 (today):

  • Friends: 11
  • Recruiters: 11
  • Industry Peers: 19
  • Networking Events: 6
  • Interviews: 8
  • Partner Chats: 3
  • Total: 58

Here are my loose definitions for these categories:

  • Friends: People I have a deeper relationship with and whose primary interest isn't necessarily in discussing the job search.
  • Recruiters: People who have a vested interest in pairing me up with a job. These could become friends at some point, but my primary purpose in engaging with them was to talk shop.
  • Industry Peers: People who work in the industry and want to make a connection to expand each other's networks. Again, these folks could become friends at some point.
  • Networking Events: Events geared towards either making connections or learning something new with a bunch of other people.
  • Interviews: Discussions with people who have a possible role that I can fill.
  • Partner Chats: I do still have an entrepreneurial bone in my body, so these are discussions with those I am working on building a business with.

As you can see so far, most of my time has been with folks in the industry, making connections, trying to explore what opportunties are out there.

I'm hoping that I start to see more growth in the "interviews" column by this time next month. 😅

Things I've learned

Alright, so back in the day, I used to do these blog posts where I'd accumulate a bunch of random thoughts over a period of time and then list them out in bullets. I'm gonna do something similar here, so here are some things I've learned in the past month:

👨‍🎨 Personal growth insights

Safe spaces rule.

Every classroom in my daughter's school has had a "safe space", an area of the room that kids can go to when they're overwhelmed or stressed out. It gives them a place to calm down and process their emotions.

My daughter recreated one in her room. Beneath her lofted bed, she's created this fortress of solitude. It consists of a beanbag chair, a little lamp, some stuffed animals, a sound machine, books, crafts, and affirmations scotch taped to blanket walls.

When I took my first virtual therapy call, I did it from that safe space.

Our house isn't big enough for me to build a room with one, but once I get employment again, I'll begin finding a way to add one on. It's important to have a space you can retreat to where you feel safe.

Anxiety is an asset.

There's a reason we feel anxiety: it helps us stay safe from threats.

But when you're abundantly safe in nearly every sense of the word, anxiety itself becomes a threat.

I've been dealing with runaway anxiety issues for decades now, which is a big part of the reason I don't feel comfortable spinning up my own business at the moment. The last time I did that ended with a similar series of rolling anxiety attacks.

But as a professional software architect, anxiety is actually pretty useful. Being able to envision possible threats against the system allows you to create mitigations that will keep it safe and efficient.

Of course, you gotta be careful to not let your applied anxiety run away from you. Easier said than done.

"It'll all work out. Even if it doesn't, it all works out."

My lifelong pal Cody's mom is a paragon of confidence and chillness.

I went for a walk with Cody a week into being laid off, and we got to talking about her parents.

She shared that her mom often says that quote, which is what gives her that confidence.

I need more of that in my life.

Gravity Falls is an amazing television show.

You all should look it up on Disney+ and burn through it in a weekend.

It's one of those shows that slowly builds to a gigantic payoff at the end.

The finale hit me with all the feelings.

Plus, it's a good show to bond over with your seven year old daughter.

Journaling really helps with perspective.

I've journaled every day since getting laid off. Reading back through them, I'm seeing patterns into what activities contribute to good days versus bad days.

Good days include some sort of vigorous workout, a conversation or two with a good pal, and tons of encouraging self talk.

Bad days include skipping the workout and sitting by yourself with your horrible, negative self talk.

Journaling is proof that life still goes on even if I don't have a job.

It's also proof that I'm at least taking some advantage of not having the responsibility of a job. (Not nearly enough, though.)

What helps my depression is a clear vision.

I've realized this month that it's when I've taken the path of least resistance when I've ended up the most miserable.

When I was a senior in high school and needed to decide what to do with my life, I picked a school (the U of M) and a degree (computer engineering) that were convenient because of proximity and my interest in computers.

My first semester of college was a complete shock.

For the first time in my academic career, I hated school.

The classes absolutely drained me. My "intensive precalculus" class sounded about as fun as you'd imagine. I mean, yeah, there are some people out there who enjoy math, but it's a rare breed who would say that they derive pleasure from "intense math."

My calculus-based physics class was a kick in the teeth. I've always been told I'm smart, but memorizing and deploying specific formulas on demand was not my strong suit. It made me feel dumb.

It felt like I was there because I had to be there, not because I wanted to be there.

And how ludicrous is that? I spent $12,000 per semester out of some perceived obligation to do so.

When I failed miserably out of engineering school, I sat down in Coffman Memorial Union and scrolled through the class directory, looking for something that looked interesting to me.

I ended up landing on a class called Broadcast Television Production, which gave me so much energy.

It required me to become a journalism major, so I switched over to that.

That path led me to an internship at WCCO, which was one of the most enjoyable professional experiences in my life. I mean, I got to hang out with hard working creatives that perfectly blended their surly dispositions with a passion for making engaging videos.

Now that I'm in my mid-thirties, I feel like I no longer am obliged to follow any specific path. The only thing holding me in place is myself.

For the past six months, I've felt like I've been stuck in this fog of uncertainty and depression. I've felt useless, a drain on myself and those around me.

This fog has led me down some dark paths where I've said some really nasty things to myself, kicking myself for being a loser, a failure, an idiot.

But really, my problem was that I just lost sight of who I am and what I want to be.

So while I'm still squinting to see my way through the fog, I'm using some of my other senses instead.

I'm using my ears to listen to my friends and network who are serving as voices to pull me out.

I'm using my nose to sniff out opportunities and make new friends.

And perhaps the most important of all: I'm using my heart to decide what will make me feel fulfilled and useful.

All of that stuff is helping me form the vision for what the next few years of my life looks like.

The two resources I have to offer those who may be in a similar situation would be my pal Kurt Schmidt who is currently in the final stages of a book that helps you formulate your 10 year vision, and my idol Arnold Schwarzenegger's new book Be Useful.

I cannot recommend the audiobook version of his book enough. Hearing Arnold say things like "rest is for babies, and relaxation is for retired people" hits so much better with his accent.

The messages shared in children's programming are important to hear as adults too.

I've been hanging with my kids a lot this month, and my son is super into Paw Patrol and Blue's Clues.

In the "Big City Adventure" musical movie, you follow Josh (yeah, there's been several new "Steve" characters since the show debuted in my childhood) as he tries to achieve his dream of performing on Broadway.

Are the songs simple and annoyingly catchy? Definitely. But you know what? Sometimes, it's important for us, as adults, to believe that "happiness is magic" and "you can do anything that you wanna do."

Paw Patrol is another one of those shows where, as an adult, it's easy to complain about their reductive storylines and fantastical premises.

But on the other hand, I have a vivid memory of discussing the Green Ranger's transformation into the White Ranger on the bus as a first grader.

These stories serve as lessons for teamwork, cooperation, sharing, and the importance of spreading joy and helping those in need.

These are traits that come easier to some than others, but they're crucial if we want to have a thriving society that lifts all of us up as humans.

Plus, sometimes, it's just fun to get invested in silly, simple characters and storylines.

So while I'm still gonna watch RuPaul's Drag Race or FUBAR when the kids go to bed, don't sleep on the shows that your kids are into. If you can drop your "I'm too good for this" mentality, you might just remember how simple life can be if you reduce it to its basic concepts.

How does one build confidence without cultivating hubris?

Is it just staying humble?

Asking for a friend.

...okay, I'm asking for myself.

Brain pathways are forged through the tall grass.

My therapist gave me this analogy as a way to help me visualize how to deal with changing your perspectives.

When a pathway is stomped through the tall grass, it's easy to walk down it.

But sometimes, those pathways no longer serve us. We still choose to walk down them, though, because it's easy.

If you want to forge newer and more helpful pathways, you gotta do the hard work of stamping out new pathways.

Eventually, if you keep doing the work, you'll discover that the old pathways become overgrown, and the one you stamped out for yourself is now the easy path.

I think this metaphor works for so many areas of our lives, like getting into shape or improving our own self talk.

If I'm so smart, why can't I beat depression?

I wrote that question in my journal, and I think it's because depression might not be something you beat. It's something you experience when you have achieved so much and aren't confident in what's next.

You "beat" depression by choosing to take a step towards your vision every single day.

You "beat" depression by spending less time with your brain and more time with your heart.

You "beat" depression by engaging in creative pursuits that make you happy. Just you. Nobody else.

👨‍💼 Professional insights

AI is so much fun to experiment with!

One of the goals I set for myself this winter was to clean out the crawlspace we have under our steps.

As any homeowner knows, it's easy to accumulate stuff over the years. The item that left the biggest footprint? Several totes filled with baby clothes.

It doesn't seem like we're on the path toward baby number 3 at all, so we figured it was a good opportunity to purge it all.

I ended up donating 12 boxes of clothes.

While I carefully placed each item into one of those boxes, I dutifully tallied each one so I could calculate the fair market value in order to write the donation off on my taxes.

Now, this is something I've done for years. I find some spreadsheet on the internet that helps calculate it, then I manually add the items to the sheet to end up with the value.

This time, I decided to try to use AI to help me figure this out.

I live streamed the whole process, which you can check out here.

I learned two things during this experiment: first, OCR tools aren't that great at reading tally marks (but honestly, they did better than I expected). Second, while we're still a fair ways away from being able to hand off tasks like these to AI bots, it's impressive how far GPT-4 was able to get from my basic prompting.

Can AI really take away the "soul sucking" parts of our jobs?

There are a lot of mechanical tasks that our brains are wired to be good at: counting, pattern recognition, and so forth.

These tasks are often the crappiest parts of our jobs, right? It's the monotonous, soul-sucking parts of our work. And we even call it soul sucking because it often feels like stuff that gets in the way from pursuing better, more fulfilling things.

So what does that leave us with? If the soul sucking parts of our jobs are automated away, what does it mean then for us to be human?

Maybe the future here isn't that AI will kill us all. Maybe it will force us, for the first time in the existence of our species, to truly deal with what it means to value a human life.

It will free us up to pursue creative pursuits. To keep digging deeper on our humanity. To ask new questions about what that actually means, and then allow us to pursue it together with machines helping us do some of that hard work for us.

Maybe something I can look into is figuring out how to use AI to help us understand our brains better. Like, can AI help us figure out the chemical imbalances that lead to severe depression? And if it can, can it help us synthesize treatments to keep our brains in perfect balance all the time? And if it can, does that prevent us from being human, or does it make us more human?

"Happiness is to write code that does great things for other people."

Before getting laid off, I bought tickets to Code Freeze at the University of Minnesota. The annual event focused this year on artificial intelligence, so it would've been foolish not to go.

I am so glad I did.

The event kicked off with a keynote from Andreas Sjöström, a long time industry leader, who shared a story of a paper he wrote when he was young.

His teacher asked him to define happiness, and he came up with "happiness is to write code that does great things for other people."

Really, when he said that, it felt like someone suddenly turned the focus knob from "blurry" to "sharp."

Writing software is challenging work filled with constant struggle, but once you get things working right, it's magical.

We, as engineers, often lose sight of that magic because we get so invested in discovering the secrets to the magic.

Sometimes, it's nice to just sit back and appreciate the opportunity and privilege we have to deliver technology that brings not only joy to others, but empowers them to go forth and do great things.

"An architect's crystal ball is being connected to others."

The other networking event I attended that brought so much joy is the AppliedAI meetup.

This month's meeting featured Jim Wilt, a distinguished software architect, as he discussed AI's role in an organization's architecture strategy.

The thing that struck me at this particular event was how dang smart everyone there was. All forms of intelligence were explored. Some folks were really keyed into the emotional side of intelligence, while others were approaching things from an analytical lens.

All of us were working together to gain some insights into how we can better use these amazing tools we've been given.

That spirit was wrapped up in a story Jim was saying about the importance of collaboration.

In isolation, you're only as smart as yourself. When connected to others, you are able to make deeper and more accurate insights into what might work for your own situation or problem.

The key takeaway? "An architect's crystal ball is being connected to others."

If we're going to answer the tough ethical and societal problems that surround these new AI tools, the only way we'll figure it out is together.

What's next for me

Certainly, my next month will involve more meetings, more interviews, and more digging into this vision.

I commit that by this time next month, I'll be back with a more clear vision of what I want my life to be. That way, when one of you wonderful people asks me "what are you looking for," I can provide a hyper-focused answer.

As always, a huge thanks to those who have reached out and offered their support. Like I said above, being connected to others is really what makes all the difference.

If you would like to help, here's how:

  1. If you know of a full time (32-40 hr/week) job opportunity where I can help architect a complex software system, explore how AI can fit into an organization, or lead a team of nerds towards building an awesome product, please send it my way.
  2. If you have insights or articles that speak to how AI might force us to define our humanity, please send those my way.

Until next month, stay in touch!


Is materialism really such a bad thing?


🔗 a linked post to tomgreenwood.substack.com » — originally shared here on

The French priest Pierre Teilhard de Chardin famously said that “We are not human beings having a spiritual experience. We are spiritual beings having a human experience”. In other words, our minds and souls are having a material experience here on Earth. You would imagine that a healthy society would therefore cherish both sides of this duality - the non-physical and the physical. The strange thing about our modern culture though is that we have rejected almost all concept of spirituality and, according to Watts, we have also forgotten the value of the material world, leaving us with nothing that we truly value.

I just finished bringing 12 full boxes of baby clothes outside for donation.

Twelve boxes of mostly mediocre fabrics stitched together to be worn, what, ten times at the most? And in some cases, never worn at all.

Twelve boxes that contained thousands of dollars worth of labor to purchase them initially, not to mention the thousands of hours of labor to stitch them together in the first place.

And while placing every single item inside those twelve boxes, I hardly felt nostalgic or wasted any time lamenting the loss of anything I was discarding.

I kept thinking of a quote that says, “Look around you. All that stuff used to be money. All that money used to be time.”

And it made me think about my anxiety surrounding my job search. Needing to get myself back into the work force, just so I can keep consuming more stuff?

I think a lot of my anxiety stems from moments where I’m unable to make sense of a given situation (or, at the very least, make peace with it).

This is the system we’re in. There’s only so much I can change about it.

My kids got so much stuff for Christmas this year. Thousands of dollars of toys, books, clothes, games.

And yet, they don’t really care about any of it.

Their Barbie dream house? It’s in shambles, with stickers peeling off the walls and various marker doodles covering the floors.

Their PAW Patrol Lookout? Shoved in the corner along with two complete sets of each of the 7 (wait, 8? wait, no, they added a few more?) characters with vehicles in various states of destruction.

The best I can hope for is that they get a few hours of enjoyment from these toys.

Because someday soon, probably within the next two years, I’ll have to grab twelve more cardboard boxes out of the garage and start placing all of those toys into them.

And there is very little about this situation that makes sense to me.

Continue to the full article


Leaving Google Cloud


🔗 a linked post to newsletter.goodtechthings.com » — originally shared here on

I’m used to the next right thing feeling certain and obvious. That’s probably because I’m used to being young. When you’re young, there are a lot of people out there whose examples you can imitate, and relatively low risk in trying things you’re not sure will work out. You also have an unearned confidence that comes from not having failed much yet.

But even the most conventionally successful of us, young or not, may reach a place in our careers where THERE IS NO OBVIOUS NEXT STEP. The things you’ve discovered you’re good at may not exactly line up with a standard corporate career path. There may no longer be an existing, ready-made challenge that’s the right size for you to step into.

There will just be a you-shaped hole in the world—its boundaries defined by your unique connections, the extreme limit of your skills, the scope of your ambitions—and trial and error is the only way you can figure out how to fill it.

As I’m oft to quote, Lisa Simpson’s “a challenge I can do” bit comes to mind here.

To be honest, this has been the toughest part of being on the job hunt.

I never wanted to follow a conventional career path. I’ve enjoyed the flexibility of my professional life so far, but I do yearn for the perceived stability of a full time thing. Many full time things don’t often give you much flexibility.

I suppose all I can do is just putting myself out into the world and explore until I find a “me-shaped” hole that looks close enough for me.

I sometimes hear the phrase “unapologetically you” tossed around, and I guess there comes a time where you either need to fully embrace that ethos or jump into premade boxes which only can represent a portion of your self.

I think I’m trying to pursue the former.

Continue to the full article

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