A Year in Review
Older, wiser, jumping slightly higher. Here's some advice I wish I had a year ago.
Heyo, dearest reader!
Thank you for coming back to another edition of Dunk Day. We’re so back, like the J. Crew Catalog that seemingly all of Substack has been talking about for the last few weeks. This reference may or may not mean a great deal to you, but it certainly does prove that this stack is topical. Exactly what we’re going for!
I was looking back through my own archive (just like J. Crew! Topical!) and realized this silly little Substack had its first real post last August. Considering how prone I am to going nonstop and how bad I am at reflecting, I thought I would try and buck the trend and spend a little bit of time in retrospect. Everyone loves an advice column, especially when it’s from yourself to yourself. So let’s dive in!
Trying to do this by 30 isn’t happening
Ahhh, what a naïve thought this was. The math went something along the lines of adding an inch to my vertical every month. Reality has gone something like an inch every three to four months. There are a number of reasons behind this that we can get to in other areas, but the expectation game was mismanaged, and honestly I’m still not sure when this will happen, 12+ months later.
Let’s develop a scoring system and give myself a grade on it because it would be funny and we can: out of 5 bunnies (hooper slang for great feats of jumping, or just a good metaphor that is accessible to everyone, take your pick) I give myself: 🐰
Tell more people about it
This topic feels a bit vulnerable, which has never been my forte. An extended family member once secondhand commented on this by saying something along the lines of “I never actually hear anything about how he is or what’s really going on.” Now, that was nearly ten years ago, and I think I’ve grown a lot in that area, but vulnerability with those outside my inner circle brings a certain level of trepidation. That being said, let’s simulate a conversation I had in my head around telling a co-worker or casual friend about this idea:
Friend: What’s new dude?
Tim, from Dunk Day: Well, it sounds insane, but I’m trying to dunk a basketball!
Friend: You’re right, that is insane. You’re a big dumb idiot and should probably give up. You had an 18” vertical in high school!
Tim, from Dunk Day: That sucks. I guess I won’t tell anyone else. :(
Some great projected negative self-talk, no? And how did they know about my high school vertical? I think you get my point, dear reader, and you’re also not here to work through my issues with me so we can get to the takeaway. That being the exact opposite has been true!
There has certainly been a healthy level of skepticism, ranging from “really?” to “that time of your life might have passed you by” but most responses have been overwhelmingly positive. I really mean the overwhelming piece. Off the top of my head, I can think of five people that were legitimately fired up about me trying to do this, and how cool it seemed. We can easily add in another handful that check in periodically in real life. I frequently rave about the community, whether it be on this Substack (including you, dearest reader, pat yourself on the back) or in person, and I honestly couldn’t be luckier to have it. Just the other day, a fellow Substacker found me and reached out, having recently completed his own Dunk Day. That’s so dope!
There’s a lot of negativity out there (especially online, more on that in a second) and it’s easy to project that onto this ambition because it’s a bit off-the-wall, but that hasn’t been further from my lived experience. This has been awesome to talk about and I wish I had done more of it earlier on.
🐰🐰🐰🐰🐰
Internet creating is nuanced...and fun?
I must admit that the concept of internet creators leads to a lot of mixed feelings. The immediate association, for me, of an internet creator is their SponCon (sponsored content for those that aren’t chronically online, which, proud of you) and GRMW (get ready with me). Shall we just say that these don’t lead to positive feelings around of all that, less because of the creators themselves and more because I just don’t understand the mass content consumption world that we live in. I have better ways to spend my time than being sucked into the black hole of these 5-30 second videos. I’m spending three to four days a week building towards this dunk, and I’ve set ambitions for my next projects after that, like getting better at guitar or building a cooking foundation outside of the three to four staples that are tired. We only have one life and I have a lot of things I’d like to pack into it, which makes the the math pretty obvious to spend as little time as possible consuming content that isn’t pushing me towards these goals. And yet…
This is the talk of a hypocrite. Since I started this Substack, the platform has made a number of feature releases, including native video hosting, but YouTube made more sense as a home for these videos. For my content. From there, it’s easy enough to link out to them. It’s felt like learning a new language (what should be a standard YouTube video? What should be a YouTube Short?) and yet for some reason, the almighty overlord algorithm has rewarded my somewhat frequent posting with views and likes.
It’s just as addicting from the other side! My first short about a year ago got 100 views. Most of them the last year have gotten around 400, with one even getting seven likes. But the other day, I posted a Short in anticipation of this post (check it out below), just a simple video comparing my jump from a year ago to today. I didn’t think much of it, and then 24 hours later it had something like 4.7K views and 40 likes. (Can I monetize and start getting some of that sweet, sweet ad revenue? Any brands want to sponsor/collaborate? HMU!) Here I am with a ringlight, lav mics, and a tripod (at least they were free from work) becoming everything I stood against.
Without spiraling too far into this internetistenial crises, I believe the takeaway can be somewhere in the middle, and somewhat positive. Or at least I’ve rationalized it that way. I’m doing something new (we know how I love the growth mindset) and tapping into a more creative side of me that has been dormant for years, or nonexistent. The idea with this Substack, and all overlapping internet posting, was to serve as a journal for my thoughts on this journey. I haven’t departed from that. What’s not to love about unlocking a new skill along the way?
Score: 🐰🐰🐰 + 🤳
Hater(s)
Remember how I was talking about negativity, especially online? Of course you do, because you’re absolutely dialed in. Riveting stuff. Great work. So, I did experience a hater. In a perverse kind of way, it was fun and validating, mainly because this journey has been hard and I would expect more people to talk trash about it, especially online.

It’s funny that trying to jump higher and dunk a basketball leads to this online interaction. I am unbothered. If anything, it reinforces the positive to negative ratio of feedback I’ve gotten, which just ends up being a positive. We’ll stay tuned on this one as my creator journey takes off, probably so many haters in my future once I hit the big time. I’m also linking the “Leave a comment” button below, maybe I have more haters on Substack that are now feeling emboldened. Let’s hear it!
🐰🐰🐰 + 🧌
Okay, I’m really just getting started on these thoughts but this has turned into a full post already. Let’s take a beat and regroup whenever I find the time to post again. Dunk Day with a multi-part post, who would’ve thunk it!
Thanks, as always for jammin with me! Know that I really, truly mean that, if it wasn’t obvious before, this community is dope and greatly helps with the day-to-day motivation. And if it really wasn’t obvious before, I need to work on clarity in my writing. Stay tuned for part two!