How to People

Where sharp eyes meet sharp wit: A bi-weekly newsletter on strategic gatherings through a very human lens.

Latest Issues:

What should you actually charge? (so much bad advice)

When I first started Wondry, I had no idea what to charge. Like a lot of first-time founders, I turned to Google. I read the pricing advice blogs. Downloaded the templates. Shamelessly scoured other people's websites, hoping they listed their pricing and trying to reverse-engineer their decisi...

Mar 26, 2025

You Can't Sit With Us

Last month, I attended what was supposed to be an "industry-specific workshop" for experience designers. The event description promised deep insights, targeted networking, and conversations specific to our field. What I got instead was a room full of college students, tech recruiters, marketing...

Mar 12, 2025

How reimagine your work from the ground up

It's Wednesday, February 26th, and today we're talking about reimagining your entire career from first principles. Forward this to a fashionable friend so they can sign up here. A few months ago, I found myself staring at a new ClaudeAI conversation after writing a single sentence prompt: "Hel...

Feb 27, 2025

When Did Business Become Broadway?

It's Wednesday, February 12th, and today we're talking about why we're all trapped in Business Theatre. Forward this to your favorite friend so they can sign up here. Quick heads up: I currently have capacity to take on one new client. If history is any indicator, this will likely be the last I ...

Feb 12, 2025

What the hell does "because it works" even mean?

It's Wednesday, February 5th, and today we're talking about why "because it works" is the battle cry of bad business. Forward this to a smart friend so they can sign up here. A few months ago, I tried to cancel my online gym membership. After clicking through seventeen billion screens, declini...

Feb 05, 2025

The nicest thing you can do is be mean

It's Wednesday, January 29th, and today we're talking about why being "mean" might be your kindest business move. Forward this to a smart friend so they can sign up here. I'm sitting at Logan Airport gate B19, watching what can only be described as adult regression in action. Despite the clearl...

Jan 29, 2025

Stop talking to your brother

It's Wednesday, January 22nd, and today we're talking about why "talk to your customers" is both the best and worst advice ever given, and how it can radically change your business. Forward this to a smart friend so they can sign up here. Two years ago, I was sitting in the audience for a small "...

Jan 22, 2025

A quick note about your pricing

It's Wednesday, January 15th, and today we're talking about why a few common pricing practices are failing everyone. Forward this to a smart friend so they can sign up here. Last week I clicked through to a website, immediately spotted what I was looking for, and then hit the pricing page. The...

Jan 15, 2025

The expensive lie of 'underpromise, overdeliver'

I clearly remember the last time I fell in love on sight. Beautiful, polished, full of promise and excitement: logic be damned—I was absolutely infatuated. It took seven days to make it happen. As quickly as it started, it fizzled. This was no prince. This was a glitchy frog. A glitchy frog who w...

Jan 08, 2025

How you and I can make things better

A few days ago, I told you of three recent experiences I had with mediocre companies cosplaying as good ones. The way I evaluate and scrutinize every touchpoint is part of my personality. For years, this has seemed like a bug and not a feature. (my daughter called me pretentious because I couldn’...

Jan 06, 2025

Trust and Community Building: What Your Members Really Want

Exploitation is never a feature Let's talk about a troubling trend in brand community building that's masquerading as a feature but is actually eroding the very foundation of what makes communities work. I recently witnessed this firsthand, and it's time to sound the alarm about trust ex...

Jan 03, 2025

We're drowning in mediocrity (w/examples)

I recently posted about my experience trying to cancel my Semrush trial. Then, a Semrush rep jumped in with this helpful comment: Now, we're not mad at Kyle. Poor Kyle is doing exactly what he's been instructed to do: insult my intelligence. It doesn't matter that Semrush wouldn't call it...

Dec 30, 2024

1 2

Latest Issues:

Hey...before you go

Hey- wanna get better at peopleing? 😏