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Daily one-pagers about AI, leadership, technology, and being human.

johnmaconline

I'm writing to think, learn, and remember in public. I'll be here everyday.

June 7, 2026 1 minute read

Tokenmaxxing Versus Token Budgeting

AILeadershipTechnology

Right now, the CEO’s are saying, “Do more with AI! Go faster! More agents! Use as many tokens as you can!”

The investors are on board. “How much can we get done with less people? Can we build a $1B company with 3 people? I’ll keep investing in your token costs. Max it up!”

But the CFO’s are starting to wince. “We spent $1.5M on tokens last month. You — just you — spent $37k on tokens this weekend alone. What the heck were you doing? We can’t keep this up.”

I’m now convinced that the future of knowledge worker compensation negotiation contains a token budget. I don’t know when that happens, but I’m convinced it will.

In preparation, I’m starting to think about the following:

  • What should we be spending tokens on?
  • Which model for what task?
  • How do we budget and limit our autonomous agents’ token spend?
  • When should our autonomous agents use a deterministic toolset (ie, just code) vs an LLM?
  • How do we track our autonomous agent token spend?

There’s a future here in how, on what, and when we spend tokens.

But for now, max it up!

June 6, 2026 1 minute read

On Your Left

AITechnologyThe250

“On your left!” serves as a polite warning to the walkers on a trail.

It means, “I’m going faster than you and I’m about to overtake you. Please don’t do anything rash. Just stay on your course. Please let me by. If you don’t, I’m gonna run you over.” It’s the polite version of “Get outta my way!”

Are you figuring out how to get AI working for you?

If not, you’re probably hearing a million “On your left!”’s.

Those will soon turn to “Get outta my way!”

June 5, 2026 1 minute read

Buzzword Factories

AIHumanLeadership

We all know buzzwords when we hear them.

Each profession and each level has its favorite buzzwords that make you roll your eyes. Each time you hear one, you lose a little respect for the person who used it.

LLMs are buzzword factories. They spew buzzwords and build word salads like it’s their job.

So tell them to stop.

I always tell my agents the following:

“Use plain and direct words. Never use jargon or buzzwords. You can assume the audience is professional and you can and should use technical terminology when appropriate.”

If you create written or presentation material, don’t use buzzwords. If you’re using AI to help you create that material, don’t let it use buzzwords.

Friends don’t let friends build buzzword word salads.

You’re the boss. Be the boss.

June 4, 2026 1 minute read

The Definition of Good

HumanLeadershipThe250

You want to work for a good company, right?
You want to go to a good school, right?
You want to live a good life, right?

Yes, of course.

But what does good mean?

Does good mean top of a list like Fortune 500, Glassdoor, or US News & World Report? Does good mean test scores, funding, or demographics? Does good mean beliefs, bank account, or healthspan?

We talk at each other like we all know what good means. Like, “You know it when you see it.” What we find, however, is that your good and my good may not align, and we get confused. So we seek others whose good looks like ours.

Once we all congregate around our definition of good, we can get down to the business of working, learning, and living a good life. The right way.

Funny how the right way always seems to come with a leaderboard.

June 2, 2026 1 minute read

10 Years

HumanThe250

What can you do in 10 years? What will you be like in 10 years?

10 years is:

  • 520 weekend
  • 1040 weekend days
  • 30 summer months
  • 130 summer weekends
  • 10 vacations
  • 11000 meals
  • 3600 showers
  • 80 haircuts
  • 3 years of sleeping
  • 3 years of working
  • 4 years of other stuff
  • 3652 daily blog posts

10 years is a long time. Or is it?

June 1, 2026 1 minute read

Just Do What Your Told

AIHumanLeadership

AI agents excel at doing what they’re told.

It’s basically what they’re built for.

But you? Is that what you’re built for?

You can, and maybe that will provide the status or the safety that you’re looking for.

But is that how you’ll make a difference?

Let the AI agents do what they’re told. You can choose, however, to do what you’re called to. Deep down.

Nobody ever made a change in this world by just doing what they’re told.

May 31, 2026 1 minute read

Does it Need to be Captured?

AIHumanThe250

Do the requirements need to be captured?
Do the meeting notes need to be captured?
Does this picture of your dog cocking its head need to be captured?
Does a video of the band from 100 rows back need to be captured?

Sometimes the answer is definitely “Yes!” Information, decisions, a moment, or a memory might all be good reasons to capture.

AI can help in some instances. But AI also makes it easy to capture too much.

Don’t sacrifice presence for capture.

May 30, 2026 2 minute read

Cognitive Surrender

AIHumanLeadership

An interesting paper from the Wharton School at UPenn defines the term “Cognitive Surrender.”

It means adopting AI outputs with little to no scrutiny, and in so doing, bypassing human intuition and deliberation.

Nailed it.

We’re living in a time of cognitive surrender. Professionals, students, and hobbyists with access to LLMs just let it think for them.

Look at any post, article, or message you receive on LinkedIn. I’m guessing here, but I would estimate that at least 90% of the content is AI-generated with little to no human oversight. LinkedIn is useless slop right now.

We also know that teachers are struggling because their students are doing the same. And as someone who works at a company aggressively pushing AI onto its workforce, I see the results in a professional knowledge work setting.

AI is here to stay. It will become increasingly ingrained into individuals’ and the system’s workflows. It’s too useful. It’s too fast. It’s too magical.

What do we do?

We insert AI into our cognitive process, rather than offloading it. It’s still your work. It’s still your output. Make sure you reason along with it. Ask it for confidence scores and when it’s uncertain. Read it yourself. Think about it yourself. Test your trust.

Keep your human cognition in the loop.

May 29, 2026 1 minute read

Fitting In Again

HumanLeadershipThe250

As teenagers, most of us desperately wanted to fit in.

Nerds, jocks, band geeks, popular, druggies. Somewhere. That’s our deep human need for connection combined with our hormone-raging teenage biology.

As an adult, you likely fit into several groups. You may even find yourself fitting into groups with differing opinions.

Be careful, however, how dedicated you are to fitting in.

Because if you’re trying to do something, say something, or make a difference, some of those groups should think you’re crazy. Even the ones you fit into.

Nobody makes a difference without someone else thinking they’re crazy.

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