Best of Lenny’s Newsletter 2026

The 25 best posts from the past year, plus a few all-time classics

Jan 06, 2026

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Anthropic co-founder Ben Mann’s words continue to ring in my ears: “This is as normal as it’s going to be. It’s going to be much weirder very soon.”

In the swirl of so much change, there’s a growing divide between the people who understand where things are going and are benefiting from it, and those who don’t and will have an increasingly hard time. More and more, I see my mission as making sure you’re in the first group.

Through deeply researched essays, in-depth interviews with world-class operators working at the bleeding edge, a thriving online and offline community, free access to the latest and greatest AI tools, and the surprisingly helpful Lennybot (trained on all of the newsletter and podcast content, it’s very good!), your subscription gives you a giant leg-up on the fast-approaching weird future.

To help you get ready for the sure-to-be-absurd year ahead, below are the 25 best and most popular posts from the past year, plus a few all-time classics. I know I put out a lot of content, so if you’ve still got 50 tabs open with posts you’ve been planning to read, close them all and check out the stuff below.

As always, I’d love your frank and honest feedback on what you love and what I could do better in the coming year. You can always find me at [email protected].

Finally, to keep myself accountable, here’s a quick look back at my goals for 2025:

Launching a new newsletter or podcast vertical ✅ — How I AI has been a huge hit (go Claire!), and I’m in the process of exploring the next addition.
Lenny and Friends Summit 2.0 🟡 — Stay tuned for some news on this 👀
Making the paid subscription an absolute no-brainer by adding more killer perks ✅ — The Product Pass has been a wild success, and wait till you see what we’ve got coming this year.
Launching a product ❌ — I decided it wasn’t the right year for this.
Above all else, continuing to deliver a high-quality newsletter and podcast every week ✅ — I think we achieved this, though I can always do better.

Now here are my goals for 2026:

Keep increasing the quality and value of the newsletter (possibly cutting back the quantity a bit)
Invest more into supporting the community around the newsletter and podcast
Launch an additional newsletter or podcast vertical
Lenny and Friends Summit 2.0 👀👀👀
Carefully balance content cadence between AI and non-AI, IC vs. manager vs. VPs, and product management vs. adjacent skills

Here we go.

📣 Quick heads-up: We’re refreshing our Product Pass partner lineup at the end of January

We’ve got some very exciting new products coming to the Product Pass in a few weeks, and to make room, a few current partners are rolling off the bundle: codes for Descript, Raycast, and Superhuman will expire on January 29th.

If you’ve been meaning to try any of these amazing products, this is your chance.

Head to LennysProductPass.com to grab your codes, and activate them by following the redemption instructions by January 29th. (Note: Descript is Insider-only, so if you’re at the Annual tier it’ll only be there if you grabbed it already.)

While you’re there, check out the other products too. Supplies are limited and deals do expire, so don’t miss out on the tools that you want to try out.

And now, the top posts from the last year . . .

Best on AI

An AI glossary—The most common AI terms explained, simply
Everyone should be using Claude Code more—How to get started with Claude Code, and 50 ways non-technical people are using it in their work and life
What people are vibe coding—Real-life examples of what non-technical people are building to inspire your own vibe-coding journey
25 proven tactics to accelerate AI adoption at your company—Practical advice from AI-forward companies like Shopify, Ramp, Zapier, Duolingo, Intercom, and Whoop
A guide to AI prototyping for product managers—How to turn your idea into a working prototype in minutes
Make product management fun again with AI agents—A guide to building AI agents

Best on career

Product manager is an unfair role. So work unfairly.—How to thrive in “the great flattening” by redefining work norms
State of the product job market in 2025—There’s a lot to be optimistic about
The definitive guide to mastering the analytical and product sense interviews—A step-by-step playbook to help you ace your PM interviews
The ultimate guide to negotiating your comp—The step-by-step guide that’s helped hundreds of leaders secure life-changing compensation
The Magic Loop—A framework for rapid career growth

Best on health

Why you’re so angry at work (and what to do about it)—A practical framework for transforming big feelings into wisdom
Why no productivity hack will solve your overwhelm—How the Internal Family Systems model can help you listen to your inner wisdom and get unstuck
How tech’s most resilient workers handle burnout—Introducing ARMOR: a new framework building on our tech worker sentiment survey insights
A builder’s guide to living a long and healthy life, with Justin Mares—For something a little different