Building our own bot

When I first met Molly, nearly a decade ago, we didn’t live in the same place. She was on the east coast, I was in Chicago, and though she did move closer we still spent our first 3 years in separate cities. In an earlier era we’d probably have a box full of letters representing that period of our relationship. But thankfully, the medium of our time allowed for more continual connection, and instead we have a phone full of text messages.

I really didn’t text that much before we met, here and there to coordinate plans. But with Molly it’s always been something different, a steady stream of communication, a connective thread, a heartbeat. Even after moving to Pittsburgh together it was still important, with both of us traveling so much. I’ve probably exchanged 1000X more messages with her than everyone else combined.

A few years ago, having accumulated 7 years worth of messages, I wanted to find a way to look at this trove of texts. On the iPhone, Apple makes it hard to look back more than a few days, requiring screen-by-screen scrolling and no good way to search. The Messages app has a clear bias towards recency, but I wanted to zoom out, to sift through this virtual letter box that we’d built up bit-by-bit. Luckily, after some digging, I learned that deep within the obscured file structure of an iPhone backup was a SQLite database containing all of our messages. Stripped of its proprietary interface, I could get my hands on a searchable version of our distanced ephemera: every sleepy “goodnight,” anticipatory “boarding now,” and phatic “&&&” that meant nothing and everything all at once.

A database is funny place to find your memories. With this tiny SQLite file, I could effortlessly recall exactly what we we talked about 100 days after we met, analyze our most commonly used words, and map the frequency and times we were in touch. That was sort of interesting, but also not particularly surprising or revealing. After playing with it for an hour or so I discarded my initial ideas for potentially visualizing this dataset. There was certainly a lot to work with, but it seemed like it would result in the kind of vapid navel gazing found in most quantified self projects.

Instead, I decided to use the database not as an archive, to be cataloged and analyzed, but as a seed, to train an AI that would make new text messages based upon our history. This plan seemed like more fun, and was a chance to learn about new technology that had only recently become more accessible. The idea was to create our own private bot, trained on all the text messages we’ve ever sent each other. I wanted it to send us one text a day, not a verbatim Timehop-like reminder of something we’d actually said in the past, but an original quip — conjured from the mind of a weird little AI whose only knowledge of the world was the texts messages we’d sent each other.

Creating mollysimon bot

I extracted the the 123MB SQLite database from my iPhone backup on Christmas day, 2018. The first thing I did was play around with a tool called iMessageAnalyzer, a Mac app that provides a quick-and-dirty UI to search and make basic charts out of your iMessage history. To begin training our bot I needed to get the messages out of the database, and into a basic text file. A simple query let me filter and export only the texts exchanged with Molly, resulting in a svelte 7MB CSV file.

To train the AI model I used an open source project called textgenrnn, a Python module that utilizes the TensorFlow ML platform. What’s going on technically here is called a “recurrent neural network,” which I had a conceptual understanding of, but was thankful that textgenrnn abstracted away nearly all the complexity. Shoutout to this Lifehacker article that made it seem so easy. Once all the dependencies were installed the program was easy enough to use: (1) feed it the seed text, (2) tell it how you long want it to train, and (3) set the “temperature,” which is sometimes called “creativity” in other ML tools.

The further you dial up the temperature, the more divergent the AI will be. At a low temperature, it would write things that were extremely similar to phrases we’d actually said. At a high temperature it could devolve into complete nonsense. I wanted our bot to be “inspired” by our texts, not just a copycat, so after some trial and error I landed on a temperature of 8 out of 10 — very creative, but not raving mad. The other parameter was how many “epochs” of training the program should undertake. The larger the number, the better the results, and the longer it would take to process. I cranked up the epochs, starting it running, and went to bed.

The next step of the process was more straight-forward. After generating nearly 40K texts, I imported them into a MySQL database running on my web server. I wrote a small PHP script to pull one out randomly, and configured an account at Twilio that would allow me to send it as a text message. Finally, I set up a cron job (a UNIX-based task scheduler) to run my script once a day, which sends the bot’s message to both Molly and myself. I also set it up so that we can request a new message from the bot at any time, by simply texting the Twilio number.

Hello, from bot

Of all my personal projects, I think mollysimon bot is the one that gives me the most daily enjoyment. It’s pretty common that we’ll both burst out laughing when the bot arrives, or ask each other later in the evening if we’ve seen the bot that day. There’s something uncanny in the language, even if the messages are often nonsense. The only words and phrases it knows are the one’s we’ve said to each other. The idiosyncrasies contained therein would likely be lost on anyone else, but for us it’s like a series of inside jokes. Not all of the 1600 text messages our bot has sent us are coherent, or funny, but more often than not they’re delightful.

A while ago I posted some good ones on Instagram:

One of our favorites, that has become part of our everyday lexicon is below. It’s such a perfect example of the bot being influenced by our texts (understanding Emoji as a proper noun) but adding it’s own oddity. The best ones make just enough sense to be funny.

Emoji is so short. Enjoy him in 8 minutes.

Even when the bot sends complete nonsense it’s still sort of interesting. As a result of the “temperature” being turned up during text generation it has the ability to make up new words, which can leave you wondering: what would “poggling to the hotel” really be like?

heh, and he sent them on emoji with Amazon Brewery till Labure Mersec. I can go to the shower which he seems a house and his song shitty and feeling awesome of the view non-different lists. They're poggling to the hotel, hopefully somewhere shitty going to the CENST.

Sometimes it’s fun to try and imagine the events that could have led to a message, were it a real one, being sent between the two of us:

I am still so bad with data right now.

Other times you can imagine that maybe it could have been a real message, assuming some liberal autocorrect mistakes mixed in.

I don’t want to push the car. Come to IDEO chicken thing around it. It's away you were always great.
I think so. One friend card called $120. Breakfast night island progress in course. It's awesome.

Rarely, although I wish it happened more often because I really enjoy it, the bot will generate a URL. Where possible, I’m tempted to buy up the domains and turn these creations into actual web pages. The example below still cracks me up every time I see it:

https://m.grroip-study?sster/tails/bc/star-old-oattward/oths-thre-editically.com/news/down.com/uncaller-terrible-live-everything-weird.com/130/2019ff./1/102//98676713916696278

A huge part of what makes the bot funny is receiving these snippets as actual text messages. If you just read them in a list (as you are here, I suppose) they don’t have the same effect as receiving them as a text, out of the blue. Although they arrive at the same time every day, it’s easy to forget and be momentarily startled by an incoming message, wondering “what is this?”

Sometimes, when the bot adhere’s too closely to the script, it can actually get confusing. The message below is one where I mistakenly thought it was actually from Molly:

On my way home!

Bot Dreams

Last year, I experimented with taking our bot to the next level by having an AI generate images based on bot messages. Similar to how textgenrnn made text generation accessible to me, this Google Colaboratory notebook made image generation something I could try without deep technical knowledge or a high-powered GPU. The included code utilizes something called a “generative adversary network” (GAN) to create images based on simple text prompts. The output is weird and surreal in much the same way as the text bot, so I figured that combining the two was only natural.

I created an Instagram account called @botdreams, imagining what it might be like if an image bot fell asleep while reading the ramblings of our text bot. Some of the result are pretty amazing:

“Alex smells cheap”
“And are you addressing the doggies?”
“Here is everything in the morning”
“Kind of so fast”

Generating these images was really fun, but also very time consuming. Each one took over an hour to create and can’t be easily automated, at least with the free version of Google Colab I was using. Ultimately, it stopped working entirely because Colab wasn’t providing me with the right GPU. I can see myself returning to botdreams again, either with a paid version of Colab or another approach. It feels like a natural extension of the project, and a way to share our bot’s weirdness more broadly.

For now though, I’m happy to be getting the daily text message from our weird little AI progeny. I like how it injects some surprise into the day, or as bot once said:

They was awesome!

Time for a Sabbatical

Slippery Rock Creek in McConnells Mill State Park

Some years pass so quickly that annual rituals seem to fold on top of each other. It’s Halloween again? Dress the dog up in the costume that it feels like we just bought. It makes him look like a UPS driver and he freezes in place until we take it off. Snap some photos, pack it away, spin around the sun again. The suitcase is never put away: unpack, repack, download the podcasts, make the coffee, board the plane. Repeat.

It’s a cruel correlation that time can go quickly when things are going well. Being busy, productive, it’s a lubricant for your calendar. The slippery days glide forward, the summer is scheduled before it’s begun, and honestly it all feels fine because the rapids of life push us forward, through the shallow waters and treacherous whirlpools. We move, we maneuver, and it feels like advancing even if we’re not sure what towards.

Two years ago it felt like the world just stopped, and to a large degree, it did. The pandemic hit at the precise moment I was already making a major change. I’d been living and working in different cities for three years, and the travel had taken its toll. Year one was exciting, year two felt worth it, year three relied on routine and repetition to mask and cope with burnout. A plane is not a bus, no matter how much you distort the idea of a commute to include one. I spent half my time away from home, and the other half away from work. How could I bring my whole self to anything?

I needed to recombine into a single me, grounded in place instead of flying and fluttering in-between. The cure for burnout, I thought, was to live and work in the same city. That, of course, was back when we thought of our work and our bodies as coinciding, before Zoom made our forward-facing gaze the only corporal consideration that matters. I never got to find out if that’s what I needed, since the day I started a new job, in the city I live in, was the day the coronavirus shut the country down. The unification of work and life remained forever pending, a mirage that disappeared as my company evolved from local to distributed.

Working from home sounds nice, and some people love it. At another time, in other circumstances, that might even include me. But I’d already been remote half-time for three years, and that’s part of what I wanted to change. I kept telling myself I was lucky, that I could work from home, unlike so many others. But still. Days filled with video calls have a way of collapsing the boundaries between work and life, while precluding any natural sense of togetherness with coworkers. It’s convenient but isolating, efficient but stifling. It was not a cure for burnout.

There’s a joke about COVID Standard Time, where today is March 744th, 2020. It speaks to the stuck-ness of the pandemic, to the impassable obstruction that’s blocking the river we were floating down. For the last two years my world has shrunk to the inside of a row house, as I peered out through screens of various sizes to watch the world fall apart. A deadly virus, racial violence, an attempted coup, and now Putin’s war.

There is much about the world that I can’t change, so I have to focus on what I can. After two years, I’m still feeling burnt out, only more-so. I need a do-over, the chance to reboot and maybe take a different path. So I’m taking a sabbatical.

I don’t have a set time frame, but I want to give myself enough space that I might be surprised by the outcome. There’s not an explicit goal, but I want to do more writing, reading, learning, and making. I’m not sure what my work looks like at the end of this, but I know that I’m more motivated by learning and collaborating with people I like, than I am by profit or competition.

Most of all, I need to take some time to reorient. When the river gets jammed up it gives you a chance to ask if you’re even heading in the right direction. Maybe I missed a turn along the way, maybe I just need to stop for a picnic and keep heading downstream. Either way, I’m taking some time to figure it out.

Abandoned coal towns of West Virginia

The last movie I saw in a theatre, before the pandemic shut everything down, was a 4K restoration of the 1987 film Matewan at the Carnegie Science Center’s IMAX theatre. It’s a film about union labor organizing in a West Virginia coal mining town, and the violent struggle between the company and workers. It stars Will Oldham, one of my favorite musicians, in his first cinematic role. Both the director and Oldham were in person for the screening and held a Q+A after the film.

Although Matewan is a real place, the film was shot about a 100 miles northeast in the abandoned town of Thurmond, West Virginia. Both towns were built along the railroad, with the tracks in Thurmond acting as a “main street” for its commercial strip. Until 1921 those tracks were the only way to access the town, which served as a thriving hub for the local coal mining community along the New River. Thurmond’s peak was in 1910, when it supported multiple hotels, banks, and even a movie theatre. Over 75,000 people passed through the Thurmond depot that year.

A few weeks ago we visited the New River Gorge National Park, which Thurmond now sits within. After winding deep within the gorge you enter the town by crossing a one-lane railroad bridge, near a dramatic bend in the New River, to discover what is effectively a ghost town.

The Thurmond depot, built in 1904 after the 1891 original was destroyed in a fire. Thurmond remains an active Amtrak stop, so the depot is still in operation (although it was closed on the day we visited).
Main street along the railroad lines. These buildings housed a dry goods store, a telephone exchange, apartments, and the National Bank of Thurmond.
The coaling tower, where an elevator moved coal from a pit below into the coal tenders of train engines. The small building to the right was a town hall.
National Park Service sign detailing how the coal tower worked.

Thurmond is just one of the numerous coal mining heritage sites in the New River Gorge region. Down the river from Thurmond is an even more remote town called Nuttalburg, which has largely disappeared except for its restored coal tipple with a dramatic conveyor stretching from the hill top to the river. The buildings are nothing but scattered foundations, a dramatic reminder of how quickly a place can fade from memory, given that the Nuttalburg mine was active up until 1958.

The coal tipple in Nuttalburg
The history of Henry Ford’s involvement in Nuttalburg, during a period in which Ford attempted to achieve vertical integration for his factories.
Coke furnaces in Nuttalburg

Living in Pittsburgh, in a house built in 1890, makes the relative time periods of these abandoned coal mining towns feel somehow closer. We couldn’t help but compare the fortunes of our neighborhood and city with those of Nuttalburg and other still existing, but struggling, towns in the area. It’s dramatic when an industry ends, and in places like southern West Virginia coal mining was everything. It makes me want to learn more, to add more tangible history to my understanding of these places.


On a related note, I highly recommend the New River George National Park for it’s wonderful hikes and views. It makes for a nice mix, and we enjoyed pairing our hikes with visits to these historical mining towns.

The New River Gorge Bridge, seen from the Endless Wall trail
The main overlook at Grandview in New River Gorge National Park

One foot in front of the other

It’s easy to enumerate what the pandemic has taken away from us, but I’m trying to reflect on the positive effects of lockdown too. For one, I’ve never been able to spend so many consecutive nights with Molly and Emoji. When Molly and I first met, we lived in different cities, and even when we moved to Pittsburgh we were both traveling constantly. Spending an entire year together has been a silver lining; I can’t imagine going through this without her. Emoji has been very happy that we’re home all the time, and I don’t miss driving out to the doggie boarding place to drop him on the way to the airport. That fuzzy little guy is the best part of working from home.

Cemetery Walks

In terms of activities, the biggest new thing for me has been building a consistent walking and hiking practice. Every day, when I’m done with work, I go for a walk through my neighborhood. Usually I swing through the Allegheny Cemetery, which has enough wooded areas to attract wildlife. I like to have a consistent route because it helps me see subtle shifts in the changing seasons, and identify how my routine intersects with others. I often see the same people in the graveyard: runners, mourners, and that one guy who brings his guitar to serenade the unkindness of ravens (that’s actually what a group of ravens is called!).

There was one man I saw consistently for months. He would park in the same spot and set up his folding chair near a candle covered gravesite nearby. He was there when I arrived, and stayed until sun set. When I saw that Creative Nonfiction had a tweet-length writing contest I fired up the old Small Flock account to write a micro-story about it:

Forest Hikes

We also started hiking every weekend. I knew I enjoyed hiking, but it always felt like a thing I did infrequently, maybe on a trip, with much planning involved. We started going because it was pandemic friendly, but it was a revelation to realize—wait, we could do this every weekend!

Molly and Emoji on the Heritage Trail in Raccoon Creek State Park

Western Pennsylvania is chock-full of public lands within a 1.5 hour drive of Pittsburgh. National Forests, State Parks, State Game Lands, Wilderness Areas. There are so many options that we’ve never had to hike the same trail twice (unless we wanted to). I love being in the woods, and the landscape here is gorgeous year-round with its rolling hills, massive rock outcroppings, and cozy hemlock groves.

We hiked over 250 miles in the last year, all of them with Emoji on our side—pulling us along as fast as he can. Who knew that such a tiny dog could have the energy to hike up to 12 miles a day? It’s one of his favorite words now; if he hears us say “hiking” he’ll jump up in excitement. It’s definitely one of the things I hope we hold on to as the pandemic fades. It’s good for all of us, physically and mentally, to spend a few hours a week on the trails.

Emoji, in his Stormy Kromer gear

The Fireside Tapes

A YouTube account called The Fireside Tapes is posting videos from the Fireside Bowl in the late ’90s. That venue, at that time, was a big part of my life. I hadn’t yet moved to Chicago, so I’d grab a friend and drive 2.5 hours from Kalamazoo to catch a show. We always drove back the same night, blurry eyed but happy, speeding home on I-94 with the windows down to stay awake.

It’s great to see these videos since very few people recorded shows during those years. It was costly and cumbersome, so at most there’d be one person with a Hi8 camera or a DAT recorder. Aspiring photographers took photos, but the film and processing were too expensive for most people.

Even at very low resolution, seeing this era of the Fireside Bowl brings back a lot of memories and reminds me how young we all were, bands and audience alike. Venues like this tended to blur the lines between the two, with the stage barely a foot tall and no backstage area or green room. After a set, the band would move their gear to the side and join the audience.


The Fireside Tapes has an Instagram account you can follow, with custom title graphics for each upload. It’s such a great way to bring a bit of branding, consistency, and high resolution to these low-res archives. I’m not sure who is behind these accounts, but thank you!

Dear Lighthouse

Just before lockdowns started in March of 2020, after my last week at IDEO, I took the California Zephyr from Chicago to San Francisco and spent a week in Mendocino County. I stayed in the keeper’s quarters at the Point Arena lighthouse, which is situated alongside the beautiful Stornetta Public Lands, and was lucky to have my trip coincide with a twice-yearly lens tour at the nearby Point Cabrillo lighthouse.

I had planned to meet Molly in La Paz, Mexico the following week, but we cancelled the trip and I headed home, into a year of COVID-19 shutdown and everything that followed. It’s been just over a year, and reflecting back reminds me not only of the beautiful landscapes but the sense of possibility I felt, which has been stunted by this pandemic. I’m hopeful for the return of that feeling in 2021.

Below is my submission to the Point Arena Light Station “150th + 1 Anniversary Writers Invitation” within their “Dear Lighthouse” category.

Point Arena Light Station, March 5th, 2020

Dear Lighthouse,

It’s hard to believe it’s been a year since we met. I suppose the memory is stronger for me, given the circumstances. I had just left my job, a bittersweet choice to spend less time traveling. My trip to see you was a personal interregnum, a space left intentionally blank, a time to look neither forward nor backward. I knew that change was coming, but didn’t understand the scale.

I traveled by train, a long continuous line connecting a Great Lake to a great ocean. From the observation car I watched night blanket the Midwest, and morning sun reveal the Rockies. Snow covered mountain passes gave way to red rock canyons. As we wound around the San Francisco Bay, a cruise ship was seeking permission to dock, its passengers infected with the novel coronavirus. We didn’t yet call it a pandemic, just a scary story set in other countries.

You, of course, know about the calm before the storm.

As I drove up the coast to meet you, I managed to stay in the present, immersing myself in the beauty of your neighbors. I hiked rugged coastlines. I napped beneath redwood trees. When I checked into your keeper’s quarters, I was thrilled to learn that I could see your light from my window. I watched you work as the vibrant sunset faded to monochrome.

How many countless people have you guided home safely? As the storm of infection swelled, and the fog of danger thickened, I knew that our time together was short. The future was rushing towards us, and I needed to be home.

It helps though, to know that you’re there.Your steadfast presence on the peninsula, the predictable cadence of your light. A year is a long time to be adrift.


My view from inside the Point Arena keeper’s quarters.