⌘ October 17, 2023

Letters with Jason, Belated [#3]

Back in July for the Letters project, I was corresponding with Jason Becker, the instigator of this whole series of letters sent around the web. He sent me this reply months ago to round out our conversation. It was profound and has taken me a while to digest and find worthwhile words to respond. You can follow the whole conversation both here on my site, and on his at json.blog.

Jarrod’s and Jason’s avatars separated by the letter emoji and their website domains, heydingus.net and json.blog, below their images.
(Image inspiration: Jose Munoz)

Jason’s Third Letter

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?”


My Reply

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,


If you’d like to be part of this Letters project, please reach out! I might still have spots open.


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Letters with Robert, October 2023 [#1] October 17, 2023