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David Holt

mister automate

David Holt · AI Solutions Engineer

AI is the craft. Understanding is the pursuit.

Software, systems, incentives, behavior, work, life — nothing is safe from unnecessary analysis.

A place to think in public.

I work with AI and software, but this isn't an AI blog.

It's a collection of things I find worth thinking about. Technology, work, incentives, systems, and the strange ways they interact. Sometimes practical. Sometimes philosophical. Occasionally useful.

Mostly, I'm trying to understand things well enough to have something worth saying about them.

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Featuring “Do What They Won't” (song).

Latest posts…

September 28, 2026 · 3 min read

Designing the Ultimate Hold Experience

Sometimes, it simply isn't economically feasible to have a live human answer every call immediately.

That doesn't mean a bad hold experience is inevitable.

If customers occasionally have to wait, the goal should be to design that wait so it demands as little of their time, attention, and patience as possible. Unfortunately, many common hold-system practices do the opposite.

Typical Hold Experience Design Flaws

Telling customers to visit your website

"If you don't want to wait, you can visit us online at..."

Often, the customer's inability to accomplish what they needed online is the entire reason they're calling you.

Stopping the hold music to make an announcement

The music stops. The customer thinks someone answered, grabs the phone, and hears:

"Your call is very important to us..."

Nobody answered. The system just interrupted the customer to tell them they're still waiting.

Telling customers how much you value their time

"We know your time is valuable."

"We value your time."

"Your call is very important to us."

These messages are being delivered by a robot while the customer is experiencing the opposite.

Design the experience to demonstrate that you value their time instead.

Repeating messages instead of providing information

"Thank you for continuing to hold. Your call is important to us."

Repeating this every few minutes doesn't help the customer. If you're going to interrupt them, provide useful information.

Calling normal call volume "unusually high"

"We are currently experiencing unusually high call volume."

If customers hear this message every time they call, the volume isn't unusual. It's your normal call volume.

Advertising to a captive audience

Someone waiting for help probably doesn't need to hear about your latest promotion, loyalty program, or premium service.

Don't turn an unavoidable wait into an advertising opportunity.

Designing a Better Hold Experience

Set expectations

If you can reasonably estimate the wait, tell the customer:

"Your estimated wait is approximately 12 minutes."

For longer waits, provide an update when that estimate meaningfully changes.

Keep the music playing during automated updates

Lower the music during automated updates instead of stopping it. Use a consistent tone for those announcements and a completely different sound when an actual representative connects.

Offer a callback

For longer waits:

"Your estimated wait is approximately 20 minutes. Press 1 and we'll call you when a representative is available. You will not lose your place in line."

Let customers stop paying attention

Tell customers what will happen when someone actually answers:

"Feel free to put your phone down or continue with what you're doing. You'll hear a distinct chime when a representative is ready."

Interrupt only when you have useful information

A meaningful wait-time update, queue position, callback option, or specific self-service option can justify an interruption.

If nothing has changed, let the music play.

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September 25, 2026 · 2 min read

Embrace the Reality Monster

There's a lot of advice about whether you should follow your passion or be realistic and chase the money.

Neither is much help by itself.

You can love doing something and still have nobody willing to pay for it. The market doesn't care how passionate you are. It cares whether what you're doing is useful to somebody else.

You can also find something people will pay for and have absolutely no desire to spend the next ten years doing it.

That's a problem too.

Anything difficult enough to produce an unusual result is probably going to take longer than you expect. You'll get bored. You'll have stretches where it isn't working. You'll watch other people quit. If the only thing keeping you interested is the eventual payout, that's a long time to manufacture motivation.

So there are some realities you have to deal with. People have to value what you're doing. The economics have to work. You need enough ability to do it well. You probably need to stick with it for a long time.

But persistence creates a strange complication.

Sometimes the reasonable thing is to quit. The evidence isn't there. You've tried repeatedly. Other people don't see what you see.

And sometimes the person who refuses to quit is eventually right.

That's what makes reality difficult to read. Some walls are actually walls. Others are just the point where most people turn around.

You need enough respect for reality to recognize the first kind and enough conviction to keep pushing on the second.

I think that's a much better definition of being realistic.

Find something you care enough about to keep doing, make sure it creates real value for somebody else, and pay close attention to what happens when the two meet.

Then adjust.

Reality gets the final vote.

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September 23, 2026 · 3 min read

Humanity Is Plagued By The Open Loop

We're obsessed with closing loops. Say goodbye before someone dies. Get the last word in an argument. Finish the project instead of shelving it. Get an answer, any answer, instead of sitting with "I don't know."

Here's the uncomfortable part: a lot of the time, the other side of that loop doesn't even know it's open. If someone dies before you get to say goodbye, they don't experience an incomplete goodbye. There's no ledger on their end waiting to be balanced. The open loop was always yours. You weren't closing something for them. You were closing something in your own head.

An open loop is really just an unanswered question about your own footing — did I handle that, is this going to come back on me. Not-knowing feels like exposure. Closing the loop, even badly, turns an unknown into a known. That's why you re-send an email you already sent, or over-explain a decision that was already fine — nothing about the outcome changes, but the exposure does.

Here's the trap: your brain can't tell the difference between a loop that's resolved and one that's resolved well. It only tracks open versus closed. A trivial unanswered text costs the same anxious energy as a genuinely important unfinished project, because to your nervous system, both just register as "open." Your task list works the same way. Half of what's on it isn't urgent, it's just open — and open is uncomfortable enough that you'll work on the wrong thing just to make a loop disappear.

So the fix isn't "finish more things." It's closing loops on purpose, cheaply, when the work wouldn't have mattered anyway:

  • Write the "no" down. A task you've quietly already decided not to do stays open forever if you never officially closed it. Cross it off. A decided "no" is an ending, same as a finished "yes" — and if it was actually important, it'll raise its head again on its own. You don't need to keep it open just in case; the ones that matter come back without your help.
  • Separate the list from the priority. Write down everything, then star the few that actually matter. That's it. The starred items get your attention. Everything else can sit on the list unstarred and stop competing for the same anxiety.
  • Notice the loops that were never yours to close. Some open loops are you chasing someone else's reaction or peace of mind. You don't control that ending. Naming it as not yours is sometimes the only close available.

Not every open loop deserves to be closed well. Some just need an ending, any ending, so your head can stop paying rent on something that was never going to pay you back.

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