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1 / A new commitment, chapters of our lives, and more

July 24, 2022

Welcome to Issue #1!

This newsletter has had a few names. First, it was Andy’s Newsletter. Then, it was Coach Class. Each had a slightly different theme. The consistent threads through both are (1) that I’ve missed writing and (2) that I just wanted to get started and skipped spending the time to determine whether these newsletters were the right containers for me to express myself. So I’d like to use the preamble of this week’s edition to explain to you (1) who Hoo Boy is for, (2) what it is, and (3) why it’s something you’ll be able to rely on to not rebrand or disappear.

Starting with (1) and (2), Hoo Boy is a newsletter full of insights and resources (collected from others and ones of my own) for people who are building a company and care deeply about making that company a place people love to work at (regardless of whether it’s a company of one or one thousand). It’s about business building and making work fulfilling for ourselves and those we work with. I’ll publish it twice a month. It’s called Hoo Boy because that’s usually what I say to myself as I push my chair back from my desk at the end of the day.

As for (3), the bottom line is that I’ve put a lot more thought into Hoo Boy than most of the other projects I’ve tried out and announced over the last two years, I’ve given it two months to sit with me before publicly committing to it, I did a ton of work to figure out what the broader container for all my work is so I can make sure any new projects are aligned with that mission, and I’m committing to publishing Hoo Boy two times a month for one year.

There’s a lot of juicy goodness in how I got to the clarity and confidence to commit to Hoo Boy, but I’ll save that for future editions. For now, I hope you enjoy this edition, and I hope you’ll share it with other folks you think will enjoy it, too.

Big Idea #1: The Cycle of Renewal

Each week in Hoo Boy, I’ll share a bit about a “big idea” that I’ve found useful to myself and to the clients I coach.

This week’s idea is “The Cycle of Renewal,” originally developed by Frederic Hudson, the founder of The Hudson Institute of Coaching, where I studied how to be a great coach. The Cycle of Renewal is based on the idea that most of us grow up being taught that life is linear when it’s actually cyclical, and one of the most important skills in life is to masterfully navigate each cycle.

What the hell does that mean?

A linear approach to life means we look at life as a line of events: elementary school, middle school, high school, college, career promotions, getting married, having kids, buying a house, retiring, and so on. As time goes on, things happen and the line continues.

But in a cyclical approach, we see life as a series of cycles or chapters that follow a similar pattern, and once you see this pattern you’ll never unsee it. There are a ton of tips and tricks on how to get the most out of each stage, but for today I’m just going to stick to describing each part of the cycle.

Whether we’re moving to a new city, dating someone new, starting a new company, beginning a new job, or taking on a new hobby, they all start the same: we’re pumped. Hudson calls this stage one: “go for it.”

But eventually new cities, relationships, jobs, and hobbies stall and we feel bored, stuck, or tired, hence Hudson’s label for stage two: “the doldrums.” When we’re here, we have a choice to make: do we quit the thing entirely (move cities, break up or get divorced, quit, shut the company down, sell, replace yourself, etc.) or do we make some small tweaks to get excited again.

If we decide just need to make some small tweaks, Hudson calls that a “mini-transition.” Maybe we decide we don’t want to break up, we just need to learn to communicate better or accept that the dishwasher won’t get loaded the right way.

But if we decide we’re in need of big changes—to quit—we begin a full-blown transition and enter the third stage: “cocooning”, where we, like the caterpillar, enter a cocoon of reflection in order to figure out what kind of badass butterfly we want to be in our next chapter of life. People hate being here, because they’re in-between an end and a beginning. Most people rush through it and that’s why they end up with a less-than-ideal new thing on the other side (another relationship that doesn’t fit, another job they don’t love, etc.).

Once a person lands on something they think is right for their next chapter (getting clearer out of what you want in a relationship, or coming up with a company idea, etc.), people are in the fourth phase, “getting ready.” In this phase, you’re dating new people (not yet committed to one, though), or networking in a new field, exploring and learning, and so on. Many people end up running a series of experiments, trying things on to see if they fit or not in this stage, and when they don’t they have to go back to the cocoon (hence the recycling arrows between 3 and 4).

Despite some cheesy words for stages, I’ve found The Cycle of Renewal to be hugely beneficial in reflecting on my career, my relationship, my health, where we live, and more. I’ve seen it open client’s eyes and help them understand why they feel so goddamned stuck, and it then lights a path for where to go next. In future editions, I may go deeper on the stages of Hudson’s Cycle of Renewal, but I’ll leave it there for now—I hope it’s as illuminating for you as it has been for me.

Reads & Resources


Regina Gerbeaux at Mochary Method did the world a huge favor when she created this epic Notion doc on how to run efficient meetings. This document is so good you could take it, duplicate it, share it with your team, and make it the standard for how you expect meetings to be run. Undoubtedly, you’ll find you and your team are making better use of your time.

From Twitter

Brad is the author of the new(ish) book, The Practice of Groundedness. He also writes a newsletter, The Growth Equation and coaches entrepreneurs. While some of his principles in this thread felt familiar, there were others that felt genuinely new and wise to me. My favorite? “#10: Do the Work before Talking About the Work Talking is easy. Action is hard. Be careful of a common trap, which is the fact that you are talking about the work replaces doing it. My own rule: I write my books before talking about them”


I've been on an Andrew Huberman binge. For those of you not familiar with him, he's a Professor of Neurobiology and Ophthalmology at the Stanford School of Medicine who uses his podcast to make scientific knowledge accessible and actionable to the general public. This particular episode is great for us as individuals and leaders as to better understand how to make the most of our days and enable others to do the same. I'm linking to, in case there are folks who would rather read a transcript.


One of the wildest parts of leading a company is seeing all of your unresolved mess made manifest in the processes and mayhem of an organization. I recommend every founder find and work with a therapist for at least a year, and the Therapy Journal is the perfect companion to help you prepare and structure your time and thoughts.

Dice Roll

Hiring and compensation decisions have never been more complicated. In this (free) report (and no they did not pay me to put this here), you'll get data on headcount growth by valuation (and job function), terminations, payroll, stock option pools, salary trends, remote work stats (including geo-adjustment), regional compensation differences, and more.

That’s all for this week. I’m looking forward to what’s next!