My Personal Strategy Guide To Do LESSS In 2026

Year-end lookbacks mean year-ahead planning. You’re probably there right now, too. I know I am. I figured it might be worth writing my framework down and sharing it here.

Since I’m actively working through it for everything I do - from my day job at Sunpointe, where it’ll help me examine what to update and evolve in our financial planning and investment offerings, to my editorial work at Panoptica, where it’ll help us bring focus to how the Perscient data is applicable in every aspect of modern life, and my creative work like this site and my podcasts - it’s very important to me.

So, without further ado, here’s the official Cultish Creative year ahead strategy-framing guide. I call it LESSS is MORE. Yes, I know LESSS is misspelled, but what fun would it be as an acronym if there wasn’t something memorable about it?

Doing LESSS, on purpose, so transformations hit harder is good work. At the social good level, and it’s something I believe in. LESSS stands for Logical, Emotional, Secure, Sexy-Status, and if you apply it to anything you’re working on, I assure you, you’ll do more with it.

You can take this into your year ahead business meetings or personal planning. I’ll walk you through the framework and then offer up a personal example.

Start by considering what you do and why.

This gets the general ideas flowing.

But then you have to drill in closer.

The ultimate combo question, planted in my head long ago by Seth Godin and now springing eternal, is asking:

What’s it do, and who’s it for?

Whatever it does is a transformation.

Whoever it’s for wants that transformation.

Actually wants it.

No maybes here.

They might not totally know they want it yet, but once they see the transformation it offers, you have to be highly confident it will.

A great way to summarize that, if you’re stuck, comes from Scott Galloway.

If a brand is a labeled representative of feeling earned and expected over time, this is useful.

Every transformation hits at least one of these in a memorable way:

It's logical. The transformation makes you feel smarter. Or at ease with new knowledge you know how to apply. An out-of-print strategy book does this through scarcity and curation - you found something rare. Google does this through instant, unlimited access - you found what you needed in seconds. A new AI chatbot does this through personalized reliability - it learns what you need and gets faster at helping you.

It's emotional. The transformation makes you feel loved, connected, or like you belong to some person or group. You know the feeling of the gap from before and after you experienced it. A local church group does this one person at a time, one relationship at a time, based (usually) out of a physical, tangible location. Match (.com) does this at scale - millions of connections happening simultaneously. Facebook does this by making connection feel effortless and everywhere, and by connections “friends” it’s hard to unsee this transformation once you see it.

It's secure. The transformation makes you feel content on a survival basis. Not gluttonous, but satisfied in the moment, with the ability to feel secure about future consumption too. A neighborhood restaurant you trust does this through reputation earned slowly - you know what you're getting every time you walk in. Maybe they even know your order. It’s a wonderful feeling. Stocking your pantry does a version of this through your own control. Amazon does this through the promise that anything you want is 24 hours away, always, and you can do it from your smartphone. Modern life is pretty amazing in the secure transformation category.

It's status-sexy. The transformation makes you feel good about yourself. You get a confidence boost and something tells your brain the world around you can tell. A custom piece of clothing made specifically for you carries a story. A new device carries immediacy and newness along with the “did you see my new thing” factor. It’s especially useful when our friends are impressed. A taste in something like F1 carries that IYKYK energy - where you're part of something that signals you're in the know, and when you meet somebody else who gets it too, you both get that status-boost feeling.

Once you know what it does, who’s it for, and what transformation it offers, you’re ready to answer the last question.

Is this an enterprise offering or a boutique offering?

If you look back at those examples in each of the transformations, I deliberately included a range, from small to big, of ways the feeling can be transformed. It’s an extension of the “scaling vs. spreading” idea I’ve written about (inspired by Kevin Alexander). I also borrowed the framing from the Acquired podcast guys.

Enterprise has scale. Enterprise gets big. Enterprise is Google and Facebook and Amazon and F1.

Boutique has scarcity. Boutique gets bespoke. Boutique is an out of print strategy book and local church groups and nice local meals and custom clothes.

Enterprise ideas, and profits, come from eking out a gain over loads and loads of repetitive turns. The transformation is earned by the reliability of the experience at volume. It’s Amazon deliveries always showing up in short order.

Boutique ideas, and profits, come from only making a gain one experiential step at a time. The transformation is earned by the reliability of the experience at the smallest deliverable scale possible. It’s everything luxury and everything custom-tailor made with some fantastic story you can’t wait to tell your friends about next time you see them.

With this last step, you’re trying to avoid mis-framing the transformation. If you frame something as enterprise but run it like a boutique, you’ll constantly feel like you’re behind and never able to keep up with quality at scale. If you frame something as boutique but judge it by enterprise metrics, you’ll feel like a failure even if it’s actually working.

I land here because that last bit is really hard. I have made that mistake too many times. I’ve helped others figure out how to fix just this last step a million times too. It belongs at the end. It also tees us up to start at the beginning, with “why” on our next pass, too.

Work your way down this list, and every idea for next year will find its structure.

Why are you doing it?

What’s it do?

Who’s it for?

What transformation is at its core? (pro-tip, I use LESSS because I think of it as thinking less, which is better than my normal mode of thinking more, if not too much, plus it helps me to remember the Logical, Emotional, Secure, Sexy-Status framing).

Is it an enterprise idea or a boutique idea?

And from there, you know what to do next.

Let me walk you through how I apply this to one of my own projects. Here’s an in-progress example that I’m particularly excited about revisiting and refocusing on for 2026:

Just Press Record.

Why do I do it? I like introducing people who I think might help or inspire each other. I like the feeling that I can see patterns they might not, and bridge gaps between personalities.

See how that’s good on a general level, but not great on a “what do I do with that” level?

Good. Now we drill deeper.

What’s it do? 1 interesting person gets to meet 1 other interesting person that they’ve never met before, hand curated by me.

Who’s it for? Interesting people in my network. Indirectly it’s for other members of my network, too, but technically speaking, I am learning to approach the show as exclusively for the people getting paired.

Note that this part isn’t for a million people or a mass audience. I have other podcasts trying to get lots of eyeballs and attention on stuff. On this show, I just want one person to meet one other person and I’m ok letting the world watch because - the internet means it might help a third or a fifth or a 100th person too. It seems pointless to not let anybody else see these when I have the option.

What transformation is at its core? It’s emotional, in that it’s connective. These people trust me to show up to a blind intro. They’ve seen prior examples and admit it’s a cool way to meet someone. My reputation is that I connect good people and good ideas, and this is one of many ways I prove that transformation.

And, last but not least, is it enterprise or boutique?

Just Press Record is extremely boutique. 2 guests. Technically, the audience is 2 people too. Me and the stranger I bring along to introduce each guest to. Anybody watching at home is a bonus.

My bet is the niches of people I introduce are so weird and narrow, there isn’t an enterprise offering for this. Maybe LinkedIn is that enterprise version. But for my purposes, I’m not building a networking platform, I’m just trying to introduce one interesting person to another at a time, and that’s good enough for me.

That’s my year-end strategy guide.

Your version of this might be to add one high-touch client dinner per quarter to your advisory practice. Or maybe you’ll insert one weird project with your smartest professional colleagues into your hobby-calendar. The form doesn’t really matter here. It’s all about the clarity on what it does and who it’s for, so you can put something of transformative value back in the world.

The world needs you to do this, by the way. Think about the positivity potential. Whether it’s enterprise or boutique, there’s a social good here I believe in.

If you’re working through this for yourself or a business idea, give this a spin and let me know how it comes out. And if you or someone you know would make a great guest on Just Press Record in 2026 - I am always open to pitches from my readers, just let me know!