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I'm a seasoned entrepreneur and technical co-founder who helps amazing people get their impactful organizations off the ground.
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Does AI Make Us Lazy?

2025-06-30 10:00:00

Put simply, writing with AI reduces the maximum strain required from your brain. For many commentators responding to this article, this reality is self-evidently good.“The spreadsheet didn’t kill math; it built billion-dollar industries. Why should we want to keep our brains using the same resources for the same task?”

My response to this reality is split. On the one hand, I think there are contexts in which reducing the strain of writing is a clear benefit. Professional communication in email and reports comes to mind. The writing here is subservient to the larger goal of communicating useful information, so if there’s an easier way to accomplish this goal, then why not use it? 

But in the context of academia, cognitive offloading no longer seems so benign. In a learning environment, the feeling of strain is often a by-product of getting smarter. To minimize this strain is like using an electric scooter to make the marches easier in military boot camp; it will accomplish this goal in the short term, but it defeats the long-term conditioning purposes of the marches.

I wrote many a journal entry in college complaining about this exact point, except we were still arguing about graphing calculator and laptop use.

Now that I’m older, I understand the split that Cal talks about here.

When I’m writing software to accomplish a task for work, then it’s more important for me to spend my brain energy on building the context of the problem in my head.

When I’m writing an essay and trying to prove that I understand a concept, then it’s more important for me to get the words out of my head and onto paper. Then, I can use tools to help me clean it up later.

Maybe this points to a larger problem I’ve had with our education system. Imagine a spectrum of the intent of college. The left end of the spectrum represents “learning how to critically think about ideas”. The right end represents “learning skills that will help you survive in the real world”.

When someone makes fun of a film studies major, it’s because their evaluation of the spectrum is closer to the right end.

When someone makes fun of students using ChatGPT for writing their essays for them, it’s because their evaluation is closer to the left.

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I broke my streaks

2025-06-28 22:24:00

In December, I challenged myself to knock out 100 sit-ups every day for 100 consecutive days.

Aside from a four-day battle with the worst flu I’ve ever had, I’ve wedged my toes under the couch and knocked out 100 sit-ups daily for 180 total days.

Five months after starting the sit-up challenge, I decided to step things up and add 100 burpees to this plan. For 39 straight days, I headed to my garage, unrolled a pink mat, turned on some pump up music, and did 100 burpees: drop to the floor, pop up into a squat, jump in the air, repeat.

At the start of June, my family joined a gym. Last Wednesday, I tried a Crossfit-esque class. It absolutely crushed me in the best possible way.

The next morning, I could barely walk. Every step had me limping and groaning.

I needed a break.

So I took one.

But here I am, two days later, and I still feel guilty about breaking my streaks. Even worse, I can't seem to muster up the courage to wedge my feet under the couch to start a new one.

Rest is a crucial part of any fitness plan. It lets muscles repair and grow, and it's included in every workout plan I've followed.

So why do I still feel like a failure?

I'm terrible at coping with failure1. Failure is a possible outcome to any activity, yet my default response to failure is to shut down and be completely paralyzed by it.

Instead of allowing myself to shut down this time, I am going to take the opportunity to reframe the situation:

I broke my sit-up streak. But I hit 130 straight days (and 180 total). That’s half a year of consistent effort and washboard abs!2

I broke my burpee streak. But I made it 39 days, and my chest hasn't felt this strong in years.

I paused both to rest, and now I feel better than I have in weeks.

None of that is failure. That’s fitness.

Time to get back at it. No drama, no guilt, no shame.

Just the mat, the music, and the work.


  1. I'm a failure at failure? What the hell, Tim. 

  2. These washboard abs are hidden under 26.2% of body fat, but they are there nonetheless! 

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Pizzacake: Lately I’ve been thinking about why people create

2025-06-27 10:43:00

Success won't matter if everything is easy. We celebrate big achievements because of the work and sacrifice it takes to succeed.

I watched Faith Kipchoyge’s 4 minute mile attempt today with my daughter and wife.

It was so moving to see the hoopla surrounding the attempt. Millions of people gathered to watch the fastest woman of our entire species attempt to do something impossible.

She didn’t break the 4 minute mark, but you can clearly see how much she put of herself into this singular, focused effort. That’s worth celebrating.

We used to celebrate art, we used to create for the sake of creating. But everything is content now, and there’s pressure for it to be fast and constant and relatable.

Don't forget why you started making art in the first place. Human creativity is vital, and the world needs it now more than ever.

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On speed

2025-06-22 05:47:23

There are many aspects of life that are unproductive and sluggish, and yet necessary. Some want to speed up the unpleasant hoping to make more room for the good stuff. It’s that logic that lead some think that being an interplanetary species make sense. Speed is inherent to growth. What grows achieves its purpose faster with iteration–creatures and machines. But that assumes the purpose is clear. As for websites, bikes, or the fate of our species, it is a matter of opinion. Our ability to be fast in almost everything has, indirectly, left me feeling unfulfilled, lost in the commotion.

I’ve been noticing this site slowing down lately.

It takes longer to render most pages, most noticeably the home page and about pages. It’s because I’ve added the workout streak counters to it.

I almost sprang for an upgraded Linode instance to make it run faster, but as I thought about it, I realized I didn’t actually care that the site took 3 seconds to load rather than 2.

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Put Me In, Coach

2025-06-18 11:20:30

While I wish I’d gone about it differently, I can now see how much I needed the break. A wiser, more patient version of me would have paused to celebrate the first draft instead of barreling into the second. But I didn’t, and now I’m here — nursing my wounds, feeling a little sheepish about it all.

But I’m starting to get restless. I’m feeling stronger. I’m raring to get back out there. Sentences and scenes are dancing in my head again, begging to find their footing on the page.

The sidelines exist for a reason. Sometimes, we need the break. It’s helpful to get a wider vantage point, healthy to rest, nice to cheer others on. But it’s also a heck of a lot more fun to play.

Sure, we might fall. We might injure ourselves (or our egos). We might get embarrassed. But we also might score. We might win. We might surprise ourselves. We might have a lot of fun trying.

Much like the last article I shared, this article meets me perfectly with where I’m at in life right now.

In my professional life, I spent all day today learning how to use Turbo and Stimulus. I complained nearly the entire time to myself, sure.1 But by the end of the day, I was able to serve up that sweet HTML over the wire.

In my personal life, I’ve continuing to maintain my sit-up and burpee streaks while also going to the gym. The biggest surprise is how much more confident I feel throughout the rest of my life because I keep promises to myself in this one area.

I feel like I’ve been watching life from the sidelines for the better part of a decade, and I’m slowly starting to ask the coach to be put in. And it’s… really fulfilling.


  1. I’m trying to tell my complaining self that something can both suck and still need to be done. Sorta pairs with this chonky sad panda shirt I got this weekend. 

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A Different Kind of Ultra

2025-06-15 05:11:05

When I returned home from this morning’s run, Jilly asked how far I ran.

“I’m not quite sure,” I told her. “I ran through the woods for about an hour and fifteen minutes, so that’s maybe six or seven miles, but I don’t know for sure.”

She didn’t quite understand why I would run if I wasn’t paying attention to how far I ran.

I think all of this boils down to the phase of life I’m currently in. I’m getting older and I’m okay with that. I’m not chasing paces anymore. I’m not chasing mileage volume. I’m not putting pressure on myself to progress at all costs. I don’t get upset if life gets busy and I don’t have time for my daily run. There are no ultramarathons on my docket.

Things are different now.

These days I’m chasing experiences – I want a unique one with each outing, and that’s only possible if I am fully present during each outing. These days I’m chasing future experiences and a level of fitness that will keep me on this planet for a bit longer so someday in the not-too-distant future I can be active with my grandkids.

That’s a different kind of ultra, but it’s the one I’m training for these days.

Bingo. This is me, in every area of my life lately.

This morning, I went for a walk immediately after finishing my burpees. I had my Apple Watch on, and it buzzed, letting me know that there’s been a change in my health activity.

I honest-to-god snort laughed, then immediately took my watch off and moved on with my walk.1 Of course there’s been a change, I didn’t need my watch to tell me that.

Being present is super hard, especially with the internet doing everything it can to draw me towards it. But thanks to myself skipping the internet today, I got the third corner of my garage cleaned! Only one more to go before I can really start making this area dope as hell.2

Another related observation: an interesting side effect of my desire to collect new music means that each new album has the potential to serve as the background track to this current moment in life.

There are many albums which point me to general moments in my life, not so much specific memories.

If I want to remember what it felt like to drive home from a midnight truck at Best Buy, I pop on The Presets’ Apocalypto.

If I want to remember what it felt like in the early days of dating Shanny, I’ll listen to Ombarrops by The Car is On Fire.

It’s kind of cool to see the intersection and synergy of my two collections.


  1. It was a good walk today! The boys were out laying fiber in my neighborhood and the weather was absolutely flawless. 

  2. Admittedly, more of the credit for this goes to the weather for causing Charlee’s softball tournament to be postponed, but while the rest of my family sat on screens for several hours, I got to work. 

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