I asked Jonathan a form of the question we had discussed around discomfort:

What’s an area of your life that you constantly think about, yet still feel like you aren’t making the progress that you’d like. Why?

I answered the following:

1. Courage. Why: As far as I can recall ( the truth may be different) but most things in life have come relatively easy to me. I’ve been able to get to where I am by what others might call calculated risks, but always felt super safe to me. I haven’t had to put myself out there much. yet I know that failure leads to growth and all the cliches about missing all the shots you don’t take. Im afraid to fail and paralyzed by not knowing what to do so I do nothing. Which leads me to #2

2. Discipline/Mental Toughness
Why: both my parents are very mentally tough. I feel like I have something to live up to in that regard. I guess I have failed a lot haha but always at the expense of discipline. I’m consistently inconsistent and it drives me crazy because no matter how small I start or what I try I always fall off at some point and most frustrating is that I don’t seem to learn as much as I’d hope from those experiences.

3. Having fun by myself. This one is weird because it’s recently come up during quarantine. I’ve deliberately tried to allow myself to be bored instead of distracting with some kind of media. And it’s revealed that I have no idea how to play or what I find fun anymore. I’ve tentatively dusted off my guitar and am re learning my basic chord and trying my hand drawing again. Both are super new but seem promising

Leading to Jonathan to ask if creating some SMART goals could be helpful for making progress in the areas listed above.

I said yes, and am now committed to showing him something around this by Sunday ( 11/22/20 12pm EST).

I think my mistrust of goals is well documented, but I realize it may also be a crutch. Committing to this makes me super uncomfortable and that’s a pretty good heuristic for it being worthwhile and seems like a meta way of addressing “Courage”.

Here’s my SMART Goal:

I (Jerome) will produce a 30 minute podcast episode with Chris about our respective journeys into tech by noon December 13th. Depending on how it goes we might record more episodes (I have Chris on a one episode contract :)) which will generally be about our perspectives from being tech outsiders (no CS background, no real interest in super techy things) working in technology. The intended audience are people looking to transition into tech without a CS background and those like us on the inside that may feel disillusioned and want to not feel like they are the only ones.

There was a lot of thought that went into formulating this goal. I first had to realize that for me courage and creativity are synonymous. The lack of courage I feel stems mostly from a lack of creative pursuits. In other words unless I’m making things and putting them out into the world I will always feel somewhat off — like I’m not making progress on something that is important to me.

This simple connection feels like a revelation and is all the more satisfying because I think I’ve been trying to piece it together for months or, and in all likelihood, years. When I picked up my guitar again and decided to give ink drawing another try, I got close. But there’s just something really soothing about knowing that I need to create. It takes away the pressure of needing it to be anything. It takes away and delusions of grandeur I have about the work. It’s just another part of life. I can’t explain how liberating coming to that understanding is. It feels like a watershed moment in my life and I don’t think I’m exaggerating.

It was the strange mix of reupholstering chairs with Sol, Reading Big Magic’s cogent and inspiring account of the creative process, and the conversations with you and Jonathan that led to that breakthrough.

Apart from that epiphany, reframing goals, which have always led to all-or-nothing thinking for me, as challenges got me past a particularly nasty mental block. It’s a lot easier for me to think in terms of, “Can I do X by Y?” . I’m not committing to anything, I’m going to try my best, but there’s no downside if I don’t meet the challenge.

The issue I have with goals is that I imagine this singular pursuit and that doesn’t leave a lot of room for anything else, which makes them hard to commit to or choose among because in my mind it’s such a large undertaking. I don’t think of challenges the same way. For example, after lunch on Saturday, I challenged myself to clean the kitchen in 7 minutes just to get it done and as a fun little bet between Sol and I. I worked really hard to try and beat the buzzer, but it wasn’t a big deal. Regardless of whether I succeeded or not, I could challenge myself immediately afterward to do something different instead. It’s such a subtle mental shift, but it made all the difference for me.