Idea Surplus Disorder #105

This week in Idea Surplus Disorder, we delve into the power of "unreasonable requests," how setting limits beats chasing goals, and why learning something new often requires slogging through the “moat of low status.”

See ways AI might be your new legal co-pilot, why the best time to hire a CEO might be January, and how Hampton Inn won by aiming for “good enough.”

And as always, you’ll find a mix of fun finds, practical insights, and thought-provoking quotes to help you lead, live, and think more intentionally.

I'm Matt Homann, and I'm glad you're here.

Ideas + Insights

We recommend making "unseasonable requests" all the time at Filament. That might be why I loved this post so much:

Ask for things. Ask for things that feel unreasonable, to make sure your intuitions about what’s reasonable are accurate (of course, try not to be a jerk in the process). If you’re only asking for things you get, you’re not aiming high enough. Jobs are a great example: Particularly if you’re early in your career, you should aim to get rejected from most things you apply for.

If you have not yet learned the skill of absorbing rejection, court it deliberately: Apply for some jobs you really don’t think you’ll get so you can learn to decouple “no” from surprise and dejection.

Learn to love the moat of low status:

The idea is that making changes in your life, especially when learning new skill sets, requires you to cross a moat of low status, a period of time where you are actually bad at the thing or fail to know things that are obvious to other people.

It’s called a moat both because you can’t just leap to the other side and because it gives anyone who can cross it a real advantage. It’s possible to cross the moat quietly, by not asking questions and not collaborating, but those tradeoffs really nerf learning. “Learn by doing” is standard advice, but you can’t do that unless you splash around in the moat for a bit.

Can AI become your company's new general counsel? Maybe, kinda:

I’m convinced every entrepreneur should start using AI to take charge of legal issues now. Contracts are language, and Large Language Models are exceptionally good at reviewing and even creating them. Use actual lawyers more like strategic consultants rather than paying them to do all the laborious work of contract review or drafting.

The most important lesson? Don’t let anyone—even expensive lawyers—convince you that legal strategy is too complex for you to understand and influence. With AI as your coach, you can take charge of your legal destiny and turn cost efficiency into competitive advantage.

Should CEO's always start at the beginning of the year?

The end of the calendar or fiscal year marks a time in which results are expected to be achieved, and the beginning of the year is when new goals are set. Appointing a new CEO in the new year allows them to set the company’s goals and objectives according to their own vision for the firm. Temporally aligning the efforts of organizational members with the goals and objectives of the new CEO allows organizational members to work in a more coordinated manner towards the realization of those goals.

Don't chase goals, create limits:

Setting goals feels like action. It gives you the warm sense of progress without the discomfort of change. You can spend hours calibrating, optimizing, refining your goals. You can build a Notion dashboard. You can make a spreadsheet. You can go on a dopamine-fueled productivity binge and still never do anything meaningful.

Because goals are often surrogates for clarity. We set goals when we’re uncertain about what we really want. The goal becomes a placeholder. It acts as a proxy for direction, not a result of it.

But smart people often face ambiguous, ill-defined problems. Should I switch careers? Start a company? Move cities? Build a media business? In those spaces, setting a goal is like mapping a jungle with a Sharpie. Constraints are the machete.

If you’re building a path through the unknown, it’s better to say: I won’t take money from people I don’t trust. I won’t build things I wouldn’t use. I won’t work in teams where I have to wear a mask. These are not goals. But they will get you further than most goals ever will.

Hampton Inn has become the world's largest hotel chain by relentlessly focusing on "good enough."

Fun Finds

• Atari 2600 (from 1977) beats ChatGPT at chess!
• Take a WalkShop!
• Titivillus, the "medieval demon" of typos.
• The five best John LeCarre books.
• Honeybees in ultra-slow motion.
• Than Average is a small, “unscientific” investigation into how you compare yourself to others.

Words of Wisdom

Simple, clear purpose and principles give rise to complex intelligent behavior. Complex rules and regulations give rise to simple stupid behavior. – Dee Hock

When you make something that matters, you make money. – Gail Federici

You don’t have to do exceptional things to get exceptional results. – Warren Buffett

The day I decided that my life was magical, there was suddenly magic all around me. – Marabeth Quin

It's very easy to be impressed by people when you don't see their lives. Being inspired by someone when you see the full cross-section of their existence is rare and lovely. – Emily Sundberg

Simplify, then add lightness. – Colin Chapman

Up Next From Filament

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