Jason Becker

From: Jason Becker
To: Jarrod Blundy
Subject: Letters
Date: July 7, 2023

Hi Jarrod,

It’s a bit strange to be starting one of these. For those that don’t know me who are reading along, and as a reminder to Jarrod, I started writing Letters on my own blog this year (https://json.blog/letters). I wanted to have a different kind of online social interaction, and I wanted to do it with people I may not really know. I thought it’d be a nice way to build up a dialog, be a part of building an Internet more like the one I wanted, strengthen some para-social relationships, and make sure the “long form” content on my blog kept flowing.

Jarrod reached out early, but not early enough for me to have booked up my year. But I’m glad that he decided to do his own project on his blog. I agreed to be a part of that project, so here I am, following my own rules, and writing the first letter for the month of [July] to Jarrod.

By way of further introduction, I’m the Chief Product Officer at an education-finance technology company, leading engineering, design, and product management. I love what I do, because I get to bridge problem solving and consultative work in my area of expertise (education policy), my skills as a data practitioner, my danger as a software developer, my taste (which exceeds my talent), and my never-strong-enough management skills to solve real problems for K12 schools. It’s wild to be a part of a startup for the last nine years from pre-product, pre-revenue, pre-Series A to now being a “real” company with over 50 employees.

I moved to Baltimore, MD about 7 years ago where I live with my fiancée (which I still have to look up how many “e”s each time), her mother, and our two aging dogs. Prior to that, we lived in Providence, RI for 10 years, and I grew up on Long Island, NY.

These days, besides work, I’m focused quite a bit on volleyball. I played (poorly) in high school, and I play now (slightly less poorly) in adult recreational leagues. This was one of my “I’m vaccinated, let’s go!” activities I reintroduced into my life after 17 years away from the sport. It’s been a ton of fun (and exhausting) and at this point it feels essential to my mental health. I also read quite a bit of fiction (or at least I think), typically hitting between 30-40 books a year. I love to travel, and travel quite a bit for work. Recently, I spent a week split between Portland, OR and Seattle, WA and had a great time getting out of my own routine for a bit and wandering. My style of travel is what I call “urban hiking”— I choose a spot for each of my meals in different parts of a city and wander between them all day long and see what I stumble into. I love getting a feel for somewhere different, and I love to walk.

I’ve been lightly following Hey Dingus, largely impressed with your consistency and keeping an eye on the “Projects” page especially, which is the type of thing I’d like to expand on my own site (see /books, /letters, etc). How do you feel like it’s going? Is it the outlet you hoped for? What’s success for you?

Looking forward to our month.

Jason

From: Jarrod Blundy
To: Jason Becker
Subject: Re: Letters
Date: July 11, 2023

Hey Jason,

Oh boy, I’m going to have to step up my game this month. That letter had me in awe of your skill as a writer. It flowed, man.

Thank you for that fun introduction. Given the room to stretch out their descriptions, I’ve found that everyone I’ve corresponded with so far has highlighted such interesting parts of their lives. You are no exception.

For a brief introduction of my own, I’ll say that I like to exist at two ends of the spectrum of “extremely online” and “completely disconnected”. Often flip-flopping between them with little warning.

Perhaps a little more explanation is necessary. My day job is as a mountain guide and gear shop specialist, I’ve spent most of my summers as a camp counselor, and I spend much of my free time outside. I’ve spent months (years?) of my life in a tent, gleefully leaving the internet-connected world behind during those times. But I’ve also been a certifiable nerd and Apple enthusiast for as long as I can remember. In fact, in the time between being a full-time camp director and my current job, I spent a few months working as a Technical Specialist in an Apple Store. Technology engages the part of my lizard brain that loves shiny things in a big way. So anytime that I’m not working and I’m not playing in the woods, I’m probably devouring the latest tech news, spelunking the web, or — as of the last few years — sharing that passion through writing my blog.

Lately, I’ve been considering more about how I can build a better bridge between those two interests. Sure, I get into all the topographical navigation apps, track my rock climbing fitness and routes, try the latest camping gadgets, and am generally known as the “tech guy” in my outdoor circles. But I can feel that there’s more to share. I’d like to write more about my experience in the outdoors — to share how and why they make me feel so alive — but it’s proven difficult to break into that genre.

Honestly, that’s one of the reasons I was so eager to follow in your footsteps for this project. I saw it as a way to try out a different kind of writing.

But enough about me, you offered so many jumping-off points about yourself that I want to explore!

What does it mean to work at an “education-finance technology company”? Do you create finance software for K-12 schools? I was corresponding with Chris Verbree last month about how special it is to be part of something — a company, organization, community — from the very beginning. We agreed that having the opportunity to influence the movers and shakers (and sometimes being one yourself) is compelling. What have been your takeaways seeing that company, and your role within it, grow from its infancy?

Your “urban hiking” approach to traveling sounds like the perfect way to explore a new city. I get intimidated by big cities and tend to stick close to my hotel or AirBnB. Case in point, I recently visited your old neck-of-the-woods, Long Island, for the first time but didn’t get out to see hardly any of it. We used DoorDash for a couple of meals and wandered only once. But with a plan and destinations in mind, I could see enjoying the exploration much more.

Your excitement for volleyball is palpable, and I’m so happy you’ve found your way back to it. I strongly believe that having a hobby to stretch your body is as good for you as having one to stretch your mind. Like you, all kinds of foot-powered travel appeal to me. I went for a 10-mile run just this morning that I only intended to be a 5-miler. I just felt so good to be out and moving that I couldn’t stop. A mental health tonic, indeed!

Thank you for your readership of HeyDingus. “Consistency” is my theme for the year, so I’m quite tickled to hear that it has been noticed. After several years of stasis, my appetite for new side projects there has grown considerably. I’m not holding myself to them all going on forever, but they sure are fun to toy around with. My /lists page has been a creative outlet in particular.

Oh, and I’d love to hear more about your pets and what you love about them. I saw your post at the end of June that Gracie’s health hasn’t been the best. Allow me to offer my condolences. It’s so hard to see a family member in decline. My wife and I have a cat, a dog, and a turtle that we call (and treat like) our “fur babies”. They bring us such joy and it’s hard to imagine our family without them.

Finally, I’d like to offer my gratitude for kicking off this Letters project movement (can we call it that?). You nailed the allure of it when you said it was to build up an Internet like the one you want to see. Thanks for putting it out into the world.

Talk to you again soon,

Jarrod

From: Jason Becker
To: Jarrod Blundy
Subject: Re: Letters
Date: July 14, 2023

Hi Jarrod,

Thanks for the kind words.

At home, my world is ruled by my dogs. Gracie is a 13 year old Pomeranian-Beagle mix. We got her when she was about 8 months old, right as Elsa and I were going to start living together. In fact, the weekend I closed on my first condo was the weekend Elsa picked up Gracie. A month or so later, Gracie mostly moved in with me and Elsa was shortly behind. She was my first dog since my childhood dog passed away while I was in college. She’s intelligent, loyal, and loving. This summer is almost certainly her last, and we’re doing our best through a lot of money and care to give her as much quality time left as possible. A few weeks ago we thought that would be long gone by now, but I’m happy she’s rebounded pretty well at the moment, so we’re just trying to enjoy our remaining time.

Brandy is a terrier mix of some kind. She moved in with us when Elsa’s mom, also Elsa, moved in with us 7 or so years ago. At the time, she was about 2 years old. She is mostly deaf, very low energy, and incredibly caring. She will take constant rubs, and will kiss you endlessly if you let her. She’s a true lap dog.

Martina was my dog growing up, who we got when I was 4 or 5 and had for a little over 14 years. She was much larger (70-80 lbs, versus Gracie’s 20-21 and Brandy’s 16) and a yellow lab/golden retriever mix. She was a classic American family dog of her breed. My parents never got another dog after her, to my father’s disappointment. As a result, they love Gracie about as much as we do.

So what about the work world? What is “education-finance-technology”? Well, as it turns out, most finance and accounting software is built for finance and accounting people. And it’s mostly built for large businesses or “public sector” in a broad way. But it turns out, schools have lots of specialized needs and there are tons of people in school districts— principals, central office department heads, school board members, and even teachers— that need to be involved in decisions about how we spend public dollars to impact kids. So we sit on top of all that software that’s specialized for GASB accounting and treasury functions and do analytics, budget planning, and resource allocation modeling that makes sense to everyone who didn’t get a degree in financial management. Most of what we build is behind log ins and not super shareable, but this year we built a transparency portal for the state of Arizona that’s pretty cool if you want to poke around.

Being a part of something from the beginning is pretty special. I feel fortunate, not just because I was there early, but because I feel like we built this company deliberately (and sometimes far too slowly) such that I have experienced running a company at three or four distinct phases. I know what it’s like when everyone is an individual contributor doing everything. I know what it’s like when you first start to put a team together and figuring out basic people-management and collaboration. I’ve experience[d] building a company to more than one team that has to collaborate across functions. And lately, I’ve been working on scaling my own function to many smaller teams working independently and collaboratively. So many of the folks I know who have worked for start ups get in when things are pretty good and spend a huge portion of their time hiring as they just keep growing. I feel like I actually learned how to run things. I think if I started at a company with 100 people that scaled to 1000 two years later, I would have learned significantly less about leading teams and managing people and how to build and execute on strategy. In fact, I’m pretty confident I could lead a team that had hundreds of people in total because of what I’ve learned here.

I don’t talk a ton about my work. I don’t think I feel like I’ve found my voice as a product leader outside of my job. In many ways, I can do what I do because of subject matter expertise. But I’m starting to get myself comfortable with the idea that I’ve built up skills specific to product management and even CTO-type skills, since I’ve been managing the engineers for 5 years (maybe more?) now.

I do think a way of bringing passions together is the key to success. Being a mountain guide is something you can bring to your site that no one else could. Maybe “bringing together” just means putting them side by side, two paths running in parallel, never meeting. Maybe there’s a way to braid the two lines together at times. For example, what does it mean to build community among mountain guides and enthusiasts? Where are those folks? How does being outdoors or at the gear shop influence your time with technology, or ability to be without it?

I wonder, as a mountain guide, do you build expertise on particular trails or a particular place? For you, what’s the balance between experiencing somewhere new and exciting versus a deep relationship to a single place? Maybe there are some parallels to my experience getting the time to experience different phases and sizes of my company versus simple scaling the experience of being a guide in a particular place versus further exploration. Maybe not.

I look forward to finding out.

Jason

From: Jarrod Blundy
To: Jason Becker
Subject: Re: Letters
Date: July 19, 2023

Hey Jason,

It sounds like you enjoy a pet-heavy home. In my opinion, the best kind of home. Animals — particularly the ones that you can tell actually care about you — bring a sense of welcoming and belonging to a place. Judged by the sheer amount of time spent there, my pets are the true owners of our house. And they’re always visibly happy when my wife or I come through the door. They welcome us, and everyone else, in with attention and affection. We, humans, could learn a few lessons from our pets.

Gracie and Brandy sound like such sweethearts. That Brandy is “a true lap dog” rings true here. Our Golden Retriever, Phin (Phineas), loves nothing more than to be snuggled up with us. He’s about four years old now, but seems to think he still has the body of a much younger, smaller dog. He’s goofy, rambunctious and protective, but also a scaredy-cat, lazy and pampered. He contains multitudes. My wife and I got him as a puppy about a year into our marriage.

Ollie (Ollivander) is our Maine Coon cat that we’ve had together since back in 2015 when we were dating, but he also seems to think that he’s a dog. He chatters back and forth with us, will (sometimes) walk on a leash, and used to play fetch before doing so would get him pounced by the real dog. He’s the sweetest, most loving and affectionate cat I’ve ever come across. If he can see you, he’s purring. If he’s close enough, we’ll rub his face on yours. And although he’s coming up on his ninth birthday, he looks and acts as young as he ever did. I’m convinced he’ll live forever.

Our final pet is Remus the turtle. I picked him up (literally, off the ground while on a hike) when I was doing an internship down in Alabama in 2014. I was desperately lonely in a new state, living all by myself in a house that would usually have housed nearly a dozen interns. I needed someone — well, some thing — to talk to, and happened to spot a baby turtle. I’d wanted a turtle since I was a young boy, so he came home with me.

Remus, like my other pets, has lived through an identity crisis. You see, I thought he was an aquatic turtle when I first picked him up. So for the first few weeks of his life with me, he lived in my bathtub with a little rock to lay on until I could get him a proper tank. And then when I got a tank, I likewise mostly filled it with water. He seemed to thrive! He would even sleep underwater. But, as you can probably guess, Remus is not an aquatic turtle. He’s an Eastern Box Turtle, which, despite the name, is a land tortoise. When I finally realized that and switched out his living environment, he did seem happier. But I think he sometimes misses his swimming pool. He was a personable young turtle, very curious and cuddly. Not words I ever know to be associated with turtles, but he was! These days he’s going through what I think is his teen years and is being, in a word, an asshole. I hope he’ll grow out of his grumpiness, and will perhaps be happier again when we can move him into a bigger habitat when we move to our new home soon.

Wow, I didn’t expect this letter to turn into pet central, but here we are!

Your work sounds really important. Many professions and industries seem inaccessible to outsiders because their language and processes are so specific. For example, the medical field, law, software development, and, as you say, finance, are all black boxes. We put things in, we get things out, but your everyday person probably doesn’t have any sort of understanding about how it actually works. Building tools that are more accessible to the public must help them out, but — I imagine — also make the work of finance professionals more pleasant. Kudos to you!

Do you have aspirations to lead a bigger team of your own, perhaps at a different company as a new challenge? The way you talk, it sounds like you feel competent to do so. Does that confidence get you wondering if you should try?

Thank you for your insightful recommendations about blending my interests to showcase on my site. I think you’re right, I don’t see a lot of outdoor and tech enthusiasts out there. Perhaps this isn’t quite what you were suggesting, but maybe the key idea is just to write more about what I’m doing, things I’m trying out, and what’s working. I think, perhaps, I’ve been putting too much pressure on needing an angle for my writing. (Related, I feel conflicted about having two places to write, in general.) Maybe my writing would flourish if I aim for it to be less about what’s “right” and more just about me.

Since I’ve been guiding here in the Adirondacks for only as long as we’ve lived here (about a year and a half), it seems like I often get to experience new and exciting places right alongside my clients. Everywhere is new! That novelty will wear off. In fact, it’s starting to as I begin to take clients on the same key hikes or climbs here — the ones that have a particularly friendly approach or offer a wide range of opportunities for folks at various skill levels. But what’s never the same are the people. They each bring their own unique blend of history, interests, ambitions, challenges, and talents. I love sharing my passion for the outdoors with others, and try to inspire some in them.

But to keep things fresh, I do personal trips with friends and other locals. I never want to guide something that’s at the edge of my ability level, so I always feel like I’m holding back to a degree with clients. That’s a good thing because it means I have some margin to get us out of sticky situations should they arise. It also means that if I want to challenge myself, I can try crossing the same terrain faster, link hikes together to push the mileage, or try for climbs that get me a little scared. And I feel like there’s so much opportunity, even just here in the ADK, that I’ll never run out of things to try.

Thanks for coaxing these thoughts out of me.

Following that train of thought, I’d love to hear — if you’re willing to share — about some things that scare you and how you deal (or don’t deal) with them.

Until next time,

Jarrod

From: Jason Becker
To: Jarrod Blundy
Subject: Re: Letters
Date: July 28, 2023

Hi Jarrod,

I aim for it to be less about what’s “right” and more just about me.

I think there’s more wisdom there than just talking about how to get writing to flourish. I think that’s how we flourish as people. Like Remus, you could spend your time sleeping underwater, but if you’re a land turtle, that’s where you’ll thrive. I had a pretty twisted path from chemistry student to policy master’s to research and program evaluation to leading a development team at a software startup. I lived my life aquatic, but I think I’m finally finding my own patch of land.

I didn’t realize you were new to the Adirondacks. There’s something about the “mountain man” persona in my mind that just imagines you have to be born where you roam. I also hadn’t considered that some of the novelty are the people instead of the paths. Goes to show you that maybe I’m missing some kind of empathetic, emotional, interpersonal way of thinking that I imagine the rocks becoming familiar long before I imagined the people being interesting.

What scares me. Wow. Well. Everything?

I struggled to write this letter because I wanted to think about what to say here. I’ve written versions of this letter that ended up in DayOne, and I’ve deleted a few versions too. So maybe a tough question, or maybe you just caught me in a tough (ideal?) spot to consider things.

I think what I find scary is not getting my balance right on risk taking. I think like a lot of people my age, I’m trying to get that balance right between saving (money, experiences) for later and living my life now. I try to address this with planning in the long term and freedom in the short term. After a decade or so of budgeting, I haven’t had a true monthly budget for a few years now. The decade of budgeting taught me how to spend within a certain range, and if I look at the overall numbers at the end of each month, it rarely fluctuates much. If something big and unexpected happens, I can adjust for a month or two pretty easily. But not thinking about or watching my daily spend is a luxury that has reduced some of the small anxieties associated with all of this. I know I’m safe to make an impulse purchase or plan a vacation and that I’m not going to “mess up” in any major way.

But I also have to make sure that I’m doing all the things necessary to hedge against emergencies, prepare for retirement before I’m too old to enjoy it, and even life style changes. If my partner or I want to work less, or work less hard, or do something we’re passionate about for a pay cut, can we afford it? I want to take this time of working hard in a job I love, but which is incredibly stressful, and make sure that it’s building the life I want to live.

And that’s the other fear– have I done what I can to discover the life I want to live? Am I living it? I’m acutely aware I only get one shot, and I definitely am worried that I’m not doing enough… discovery and exploration. I want to have new experiences and be open to them changing how I want to live. That’s why I love travel and why I really try to push against some of my planner impulses and just do some things.

In reality, this is an area I am absolutely not succeeding it. I find it pretty easy to do things I like, but which aren’t in that zone of playing with my time and my life. It’s too easy to decide not to buy that concert ticket, or not to go to that play, or not to go for a weekend away. And that’s what I choose all too often. So it’s a thing I’m trying to find ways to work on– how can I build my reserves to tackle that necessary activation energy to break the easy and routine elements of my life (which I love and enjoy!) and embrace other things I know I love and enjoy, as well as sprinkling in a few things I don’t like quite as much.

The whole “mountain guide” thing is a great example– I actually really enjoy going for a hike. But if I go on 3 a year, that’s about all I do. And most of the time, I don’t go for the challenging, really making a day of it experiences. I have all kinds of reasons for that– the weather in Baltimore is rarely the kind that makes me want to spend a lot of time outside, I’m often physically exhausted on weekends, etc. But the real reason is it takes a little planning, a little willingness for discomfort and the things I don’t like to get to the part I do.

So I’m afraid that this base level of complacency and stability seeking is letting some things go by that I shouldn’t. I’m afraid that I’ve made it too difficult to do certain things that I’d love. I’m afraid I let my own head get in the way of taking more chances– my body physically reacts like things are risky that have virtually no downside and huge potential upside.

Maybe that’s all too abstract, but it’s what I’m thinking about today sitting in the mountains in Colorado about to take the long, winding drive back to Denver to catch a flight home. I can’t help but look at all the trails and think, “Why haven’t I been hiking them? Why haven’t I been on skis since I’m 16? Who am I letting stop me?”

Jason

From: Jarrod Blundy
To: Jason Becker
Subject: Re: Letters
Date: October 17, 2023

Hey Jason,

Your letter has been sitting with me for the last few months. Both literally sitting in my inbox, and figuratively sitting around in the back of my mind. I, too, have had versions of this response composed in my head, but never felt that I could get my thoughts into actual words. Perhaps, even now, an embarrassingly long time since you sent this letter (I do apologize for the inexcusable delay in getting back to you) I won’t get the words out right. But I have to try.

I’ll start by asking, has anyone complimented you on how poetic you are?

I lived my life aquatic, but I think I’m finally finding my own patch of land.

That line really got me. I feel a certain hopefulness from it. Like the first rays of dawn after a long, dark night.

It sounds to me that, despite your stated fears, you’re questioning all the right things. Or, perhaps, because of your fears, you’re questioning all the right things. You’re seeking a balance, which keeps you honest about where you are and where you want to be. The way I see it, it is complacency that threatens to choke us off from a vibrant life. We get used to the way things are, rather than the way they could be. We let things slide. We stop caring. We lose momentum and eventually slow to a standstill. We lose sight of our dreams. We “get through” the day rather than live each one. By constantly questioning your balance, you keep that fire kindled.

Falling into that complacency and extinguishing that flame is what scares me. I feel it creep in each morning that my alarm goes off, set early to gift myself extra time to work toward one of my goals, and I hit ‘snooze’ instead of just. getting. the. fuck. up. It grows when I keep to myself rather than speak my mind. It makes itself at home in the pit of my stomach during the hours that I mindlessly scroll a never-ending feed on my phone.

Ugh, that word: “feed”. The visual that comes to mind is of a pig gorging itself on a bland bag of grain that a farmer plopped down in front of it. And that’s what we, et al., are begging for more of? A more perfect feed? (I say, painfully aware that I’m writing with the hope that these words will end up in your inbox and many other people’s feeds. That you and they will read and care.)

All of that moodiness to say, yes, I understand and I think we share the same fear.

But if there’s one thing that I have learned — and continue to learn — through my experiences in rock climbing is that fear is a useful feeling. It lets us know when we’re venturing beyond certain safety. It reminds us that we should take our next action, make our next decision, with caution. Either continue climbing, keenly aware of the greater risk, or give in to the fall and trust the safety systems that we’ve put into place. Either way, it’s an action we have to take in fear. The worst thing is to let the fear manifest itself as inaction. Clinging to the wall, unable or unwilling to move. With strength sapping away, and control over the situation waning. No; the path onward is to acknowledge the fear, then to move with it and through it. It rarely abates. But we become more powerful and more capable people when we decide to act in spite of the fear.

Jumping back in the water is scary. But it might get us to a new patch of land.

Thanks for chatting with me. It’s been a real pleasure.

Take care,

Jarrod