The $10,000 Hat
The $10,000 Hat
Hello from Stone Ridge, NY. Before paternity leave comes to an end, my family and I managed to escape the city for a week to enjoy the beginning of fall, my favorite season. I’m a different person when I’m upstate surrounded by woods. I could feel my nervous system relax within minutes of stepping out of the car and breathing the fresh mountain air.
When I got to the house a few days ago, I unpacked my cozy fall wardrobe and put my summer clothes in storage. During this annual ritual, I realized that I had left behind one of my most prized possessions, always in season: my $10,000 hat.
In early 2020, I started a boutique coaching firm called High Output and raised a small angel fund.
Around that time, a friend encouraged me to think about investing in a visual identity for the company. He made a compelling argument that this would lay the foundation for a brand and provide more legitimacy. I wasn’t sure where I wanted to take the company, but this seemed like a logical move because I had always wanted to build something bigger than myself. I reasoned that a fancy brand and visual identity would move me a step closer in that direction.
A few weeks later, my friend introduced me to Regan Johnson, a former Pentagram designer who was just starting his own studio, and I was immediately drawn to his work. For a new visual identity and a website, he quoted me $10,000, which felt reasonable based on my experience. Without giving it much thought, I said yes, wired Regan a deposit, and we were off to the races—another example of “blow and go” strategy.
And in just three months, High Output had a beautiful visual identity and a new website. Regan did a great job. I loved what he delivered.
Several weeks after the project ended, I received an unexpected package in the mail. Regan had sent a thank you note along with a High Output hat. The hat!
It quickly became a wardrobe staple. I even ordered a few dozen to share with clients and friends.
But then, earlier this year, I made the difficult decision to sunset High Output and consequently the wonderful visual identity that Regan designed for me. The brand no longer exists in the world.
Now all I’m left with to remind me of that phase in my life is the hat that Regan sent me.
Instead of tossing it or relegating the hat to a dark closet in my house, a symbol of my regret, I still wear it with pride, especially during seasonal transitions, because it reminds me of that time in my life and what it represents—a significant work-life transition.
That hat is embedded with important learnings and wisdom that cost me something to gain.
The first reminder is to take it slow, especially when in transition. I’m not alone in my tendency to jump into the next thing as quickly as possible—we tell ourselves that we can’t possibly waste any time, we have to start building, or figure out what’s next right now. But when we’re going through a transition, it’s better to slow down and let things unfold naturally. If I had waited 6-12 months longer, it would have been evident that investing in a visual identity wasn’t the right decision at that time. I wish that I had spent more time getting my bearings and enjoying the messy middle.
The second reminder is that I don’t need more than myself, my words and actions to move my work forward. You don’t need a fancy brand or visual identity to get started, especially if you’re a solopreneur—you are the product. The client is paying you to help them solve a specific problem. In the early days, focus on the value proposition, the customer experience and the messaging, and then iterate on those as you learn. That’s what really matters. And if you want your brand to look good, there are plenty of low cost options to get started.
The third reminder is to focus on the hard things that matter instead of getting distracted by small and inconsequential details. I spent countless hours with Regan and thinking about the logo, font choice, and color schemes. These things aren't a waste of time by any means, but they must be done at the right time. I was ultimately distracting myself from the core offering. Ask yourself, what is truly core? What really matters? What creates the value?
The fourth reminder is to embrace who I am as a coach and entrepreneur. When I step back and see the full picture with the benefit of hindsight, I realize that I was so ready to invest $10,000 because I wanted to build something bigger than myself—something so big I could hide behind it. I didn't want to be front and center because I was afraid I’d somehow fuck it all up. I had to learn to get comfortable and confident sharing my full self and being ok with the risk of failure. And over time, I realized that my clients were excited to work with me, rather than High Output. It was me they were hiring. And that’s when I knew it was time to sunset the brand.
Finally, I’m reminded that a brand is not a visual identity, but rather the sum total of the positive and negative interactions that someone has with you or your product or service. It accrues value over many years through thoughtful actions, inspiring others, and delivering great work, not a fancy veneer. While a clean-looking website might help you generate leads in the short term, it won’t make or break your business in the long term. That comes down to doing the small things consistently and delighting the customer day in and day out—commitment, through every season.
There will be times in life when we have to walk away from an investment that we’ve made in ourselves or our business because it no longer fits or makes sense. Rather than resisting this and getting caught up in the sunk cost fallacy, see it for what it is—an opportunity to let go, start fresh, and carve a new path forward. Maybe you’ll even have a few trinkets from that period to remind you of the experience and what you learned along the way.
I have a $10,000 hat to remind me of this. It’s priceless.
🌱 Seeds of Change
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Here are five things I’ve been pondering and exploring over the past few weeks. If any resonate, please feel free to forward along to friends.
🧭 Joseph Campbell on Wandering
I’m a huge fan of the legendary mythologist and author Joseph Campbell. That’s why my interest was piqued when Paul Millerd, author of The Pathless Path, shared this excellent quote from Campbell that compares wandering in life to an organic process:
“While wandering, you experience a mysteriously organic process. It’s like a tree growing. It doesn’t know where it’s growing next. A branch may grow this way and then another way. When you look back, you'll see that this will have been an organic development”
Where in your life has this been true for you?
🧊 Lewin’s Change Theory: UnFreeze, Change, ReFreeze Method
Over the past few weeks, I’ve been scouring the web to learn the fundamentals and building blocks of change. In that pursuit, I discovered Kurt Lewin’s “UnFreeze, Change, ReFreeze'' theory of change which examines how we behave and change within organizations. Lewin, a social psychologist active in the 1930s and 1940s, believed that all behavior was a dynamic balance of forces that moved in one of two directions—driving forces which push people towards change or resisting forces which prevent people from making a change. Both need to be examined and addressed to make a lasting change. “UnFreeze, Change, ReFreeze” does exactly that. Here’s an excellent primer on this theory. Practical Psychology, Youtube (6 minutes)
📚 Transitions: Making Sense of Life's Changes
I just finished reading this classic by William Bridges, and it changed how I view work-life transitions and relate to my own journey. “First published in 1980, Transitions was the first book to explore the underlying and universal pattern of transition… [It] remains the essential guide for coping with the inevitable changes in life. Transitions takes readers step-by-step through the three perilous stages of any transition, explaining how each stage can be understood and embraced.” This is a must read for anyone wanting to make sense of their own transitions or help others do the same. I have no doubt I’ll be recommending and gifting this book for many years to come. Description from Bookshop.org
🤕 Dr. Gabor Maté — The Myth of Normal, Metabolizing Anger, Processing Trauma, and Finding the Still Voice Within
Early in my addiction recovery, I read In the Realm of Hungry Ghosts by Dr. Gabor Maté and it had a profound effect on how I viewed addiction. He’s now back with a new book titled The Myth of Normal, which is “a groundbreaking investigation into the causes of illness, a bracing critique of how our society breeds disease, and a pathway to health and healing.” Dr. Maté joined Tim Ferris for a wide ranging interview where they discussed the new book and many other topics such as indigenous medicine, attachment versus authenticity, and raising a child who is capable of self-regulation. They also discussed how to cope with rage and anger, which is something I’ve struggled with over the years, and I found that incredibly helpful. I’ve already sent this interview to several of my coaching clients. The Tim Ferriss Show (1 hour, 37 minutes)
🧘🏻♀️Non-Sleep Deep Rest (NSDR) Nervous System Reset
I can’t go on Twitter these days without seeing Non-Sleep Deep Rest (NSDR) in the feeds. What is it? This term was recently coined and evangelized by Stanford neuroscientist Dr. Andrew Huberman, but it’s not new. In fact, NSDR is just a series of meditation-like techniques and practices to relax and calm the body while keeping the mind awake. Supposedly the CEO of Google, Sundar Pichai uses NSDR to unwind. A few weeks ago, I discovered a treasure trove of NSDR Yoga Nidra meditations on YouTube, and I’ve incorporated them into my mid-day routine. It’s the perfect little reset for your mind and body. I highly recommend blocking 10-30 minutes each afternoon for NSDR, especially if you consider yourself a busy person or high achiever. Slowing down each day is essential to rest our nervous systems, and integrate what we’ve experienced and learned. Ally Boothroyd (10 minutes, 25 minutes)