#2: My Roadmap, A Happy Life, The Enneagram, Spotify & Conan O'Brien
Weekly digest of things I'm thinking, consuming, and inspired by 🤘
I’m excited to be back this week with the second newsletter!
First off, I wanted to mention how grateful I was for the responses to last week’s newsletter. As I texted my buddy, Steve, last week: “I wasn’t not not shitting in my pants when I sent it out.” It was so encouraging to hear back from some of you, as well as a wonderful personal reminder of just how impactful something so seemingly small, like a text or quick note, can be. It means a whole lot, so thank you. Ha, and I promise this is not meant to shame those that I didn’t hear from or to pressure you to respond to this one.
Second off, I wanted to share a few personal updates:
Today, I will have officially completed 30 days of writing 30 posts! You can see all of the writing on harrisbrown.me/daily, as well as in this Twitter thread. I also wrote about 6 things I learned through the process. The learning I’m most excited to share though is that I really do enjoy this writing thing and that I’m planning to continue. My plan is to write as part of this newsletter (obviously), publish regularly on harrisbrown.me/daily and apply for the next On Deck Writer Fellowship to sharpen the skills and leverage the power of a community (🤞 they let me).
Tomorrow, I will officially kick-off a similar process for my music practice! I really found value in the structure, focus and momentum that the 30 day model provided for writing, so I’m excited to try the same thing for my music practice. I’ll be releasing “songs” (in quotes, bc tbd how I actually define this) on my Soundcloud page and also posting to Twitter, if you’d like to follow along.
Last off, here’s a preview of what we’ll dive into today:
🤔 How I’m Spending My Time (aka, Harris’s Roadmap)
📖 A Short Guide To A Happy Life
🎤 Enneagram & The Pursuit of Presence
🎸 Spotify 2020 Wrapped
🦄 Inspirations: Conan, Active Listening & Martha Beck
🤔 How I’m Spending My Time (aka, Harris’s Roadmap)
“Am I fucking crazy?!” I found myself uncontrollably interjecting. We were nearing the end of a coaching session, and Jocelyn and I had transitioned into a moment of silence. The reaction definitely took me by surprise; Jocelyn I’m sure even moreso. The question was somewhere along the spectrum of joke and for-real.
Here’s the deal: I don’t currently have a job, and I’m not actively looking for one. I left Airbnb in March to join Stop the Spread, was officially laid off in May (yes, comically and gratefully, while on leave) and continued working with Stop the Spread until I parted ways around Labor Day. Since then, what this has translated into is time. Lots, and lots, of time. And with all that time, I’ve been pondering, game-planning and actioning towards a single question: If I gave myself 6 months of runway to not get a “real” job, how would I spend it?
During this time, I’ve received more than a few questions about it: What’re you doing? How’re you spending your time? Are you looking for jobs? What’s your plan? When are you going to start interviewing? What do you do during the day? Could you go to the grocery store for me? And as committed as I’ve been to sitting with the question above, I’ll say I’ve been equally, if not more, self-conscious about having to face this line of questioning along the way. Certainly to others, and maybe even more to myself. I’ve known what I don’t want to do; but I’ve been far from clear about what I do want to do. My default response tends to be sheepish, muddled and non-committal. Certainly not a response that exudes confidence; which in return does little service to any confidence of my own.
If I were experiencing this moment in an earlier period of life, say early to mid-20s, the answer would have unequivocally been this: travel, adventure, vagabond, explore. Go experience some things. No questions asked. Now though, life looks a bit different. I’ve got a lovely partner I’d prefer not to leave home without, a new little mini-Aussie pup named Pepper and am now required to be physically present for at least ~18-hours / month in the pursuit of human puppy-making. Not to mention, it’s #2020. Though even if circumstances were different, I can confidently say that I wouldn’t want to be traveling for the sake of traveling. Instead, I’ve got a few other priorities and aspirations currently higher up on the list that traveling wouldn’t necessarily serve.
But, back to the question: What are those priorities and aspirations? How do I want to spend this time in pursuit of those? What am I optimizing for during this time? How am I operating during this time? What’s my plan? Do I need a plan? How am I going to make money? Do I care? Should I just scrap it all and go get a job?
I’ve been really struggling through the process of answering this laundry list of questions. I wrote about it in detail a few days ago. What I’ve found to be kind of mind-blowing is how little guidance, advice and playbooks there are out there for this type of thing. I know I’m not the only one who’s taken some time off in this way before. A sabbatical, time-off, breather, Rumspringa, whatever you wanna call it. Having anticipated this struggle is the primary reason I started working formally with a coach. I didn’t want to fold under the pressure of these questions. I wanted to stay true to this course and commitment. I wanted to sit with whatever discomfort it brought my way without falling out of my chair.
So, with that lead-up — I wanted to share my current answer to the question I posed above: If I gave myself 6 months of runway to not get a “real” job, how would I spend it? I’m equal parts terrified and excited to put this plan out there. Terrified, because I’m still plenty self-conscious about this being the “wrong” plan; not the “right” way to spend time; not what I “should” be doing. Excited, because as I’ve learned over the last 29 days of writing publicly, the simple act of sharing has served as a re-commitment device; something that begets more confidence, more momentum and more feedback simply through the act. In either case, I’m excited to learn one way or the other whether I am indeed fucking crazy.
What's the 1/few-liner? How would you describe what you're doing to a friend or acquaintance at a party?
I'm spending at least 6 months on a professional sabbatical. I'm taking seriously some creative hobbies, writing and music, that I've never created the space to fully commit to. I'm sharing what I create broadly to see what comes back, as well as to get over some insecurities I have around putting myself out there. After that, I'm planning to put into motion a few "work" projects that have been on my list for awhile: launching products, doing consulting work, maybe a few others. All things that looks like me being an owner, vs an employee. I'm structuring the time around action (over introspection), following my energy and curiosity and only committing to things to which I'm saying hell yeah.
Goals & Focus
What are your high-level goals, objectives & focus areas for this time?
Creative Expression: I currently spend a lot of time consuming. I want to reverse that trend, and actually spend more time creating, and specifically do this in the areas of writing and music. I want to scratch a few "creative itches" that have been nagging me for far too long. I also want to use these practices to get over some fears, vulnerabilities and insecurities I have tied to putting myself out there.
Betting On Me: I've worked for someone else for most (read: all) of my life, but I've always had the inclination to embark on my own. What that means though? I'm not 100% sure, but I want to experiment with a few ideas that have been percolating (eg, launch my own product/company, product consulting, maybe something else). In addition, I want explore a few alternative paths that my intuition tells me might be worth poking around; things that, to me, look like less traditional careers or further out of reach based on my path to-date.
Authenticity: I want to more thoughtfully, and formally, move down a path towards discovering my "authentic" self, or North Star as Martha Beck would say. Questions like: What is the vision for my life? What do I actually care about, give me meaning? What activities are to me? Where does my curiosity naturally take me? I want to explore these, or at least conclude whether the exploration is worth the time and nagging inner-voice.
How do I want to go about this journey? What are things I want to keep top-of-mind?
Do more, plan and introspect less
Create more than you consume
Follow your energy and curiosity
Commit with hell yeah, or say no
Think like an owner, not an employee
Guard your time, and focus religiously
Plan, Strategy & How I'll Execute
How will you go about executing on your objectives? What's the high-level plan?
Chapter 1: Planning & Systems (2 Mths | September, October)
This is the getting started; the removing blockers; the laying the foundation chapter. Consider this time the pre-work to the actual work; the time that was spent removing any blockers to being present and fully committed to the tasks and work at hand during this time. The artifacts I created: a financial plan, this roadmap, started working with a coach, established healthy daily & weekly operating systems, improved my mental fitness and shifted my mental frame to thinking like an owner & entrepreneur, rather than an employee.
Chapter 2: Creative Expression (3 Mths | November, December, January)
This is the chapter that I will commit with hell yeah to some purely creative endeavors. Consider these to be projects that have been on my list, but that with a full-time job, I've had very little space to fully develop; to build the foundation that I'd like around these practices. I keep coming back to this question: What would happen if I took these seriously, like I would a job, for a period of time? I'm not sure, but that's the question I'm experimenting with to find out. I'll be doing this in two areas: Writing and Music. With both of these the goal is twofold: create (eg, less reading, more writing; less listening & covers, more creating) and share. The artifacts I'll create will be: lots of words on paper (eg, 30 days of post), a regular newsletter, a few songs (eg, something like this, likely 30 of them), and a personal website (not live as of this writing but, harrisbrown.me).
Chapter 3: Betting On Me (3 Mths+ | February, March, April)
This is the chapter where I'll start to dip my toe back into activities that look a bit more like "work work". I have a few hypotheses/questions I want to validate that don't involve me going back to get "real" job, but instead betting on myself to make things happen as an owner (vs an employee): how might I like product consulting? would this or that idea get any traction if I put it into the world? do I want to start a company? I'll plan to explore a few of these during this time. Caveat: this area is still pretty tbd (aka, things might change), but here are the artifacts I expect to create: land a product management consulting client, launch an online product that earns $1 and sniff around a few alternative career paths (eg, music, coaching, writing).
Chapter 0: Authenticity & Undercurrents (All The Months)
All the while the above is happening, I'll be working through some exercises with my coach to help answer questions like: What is authentic to me? What do I care about, what do I derive meaning from? What are my strengths? What's the vision for my life? What're my principles? How do I define success? Ya know, all the introspective stuff. But I'll be keeping in mind this principle — Do more, plan and introspect less — I'm considering this chapter to be an undercurrent. And as always, I'll continue to consume: read, listen, consume.
1. Creative Expression
Develop a regular writing practice; 30 posts in 30 days (harrisbrown.me/daily)
Launch a regular newsletter
Write, and release, my own music; 30 songs in 30 days
Launch a personal website
Engage more on platforms in which I'm a consumer, eg Twitter
2. Betting On Me
Launch internet business that earns $1
Land product mgmt consulting client
Explore 3 alternative careers (tbd, but top contenders: music, coaching, writing)
Complete "authenticity" exercises
Start & maintain working with a coach
Detailed Roadmap & Timeline
Finally, I love a nice visual representation, so here's everything mapped out in a high-level timeline.
📖 A Short Guide To A Happy Life | Anna Quindlen
Don’t ever confuse the two, your life and your work. That’s what I have to say. The second is only a part of the first.
I first listened to this “guide” this past summer, and I’ve found pieces of wisdom in it sporadically returning to my thoughts since then; adages like: “today is not a dress rehearsal” and “it’s easier to write a résumé than to craft a spirit.” The broader perspective I find myself ruminating on most though is Quindlen’s argument for living a real, whole, full life; rather than living out fully a component of ours lives at the expense of life itself. Work tends to be the typical scapegoat here. Sparked by this book, a question I’ve found myself continually returning to is this: What would happen if we started out planning our lives tops-down, at the level of life, rather than reverse-engineering our lives from one of its components (say, work)? Quindlen would likely agree that it’s a question worth thinking about, at minimum.
This book was originally a graduation speech at Villanova, which was later expanded into this book. True to the title, this book is short (~17 minute on audio) and worth the quick read or listen.
On owning your entire life:
There are thousands of people out there with the same degree you have; when you get a job, there will be thousands of people doing what you want to do for a living. But you are the only person alive who has sole custody of your life. Your particular life. Your entire life. Not just your life at a desk, or your life on the bus, or in the car, or at the computer. Not just the life of your mind, but the life of your heart. Not just your bank account, but your soul.
On her best piece of advice for graduates:
So I suppose the best piece of advice I could give anyone is pretty simple: get a life. A real life, not a manic pursuit of the next promotion, the bigger paycheck, the larger house. Do you think you’d care so very much about those things if you developed an aneurysm one afternoon, or found a lump in your breast while in the shower?
On living, instead of existing:
It is so easy to waste our lives: our days, our hours, our minutes. It is so easy to take for granted the pale new growth on an evergreen, the sheen of the limestone on Fifth Avenue, the color of our kids’ eyes, the way the melody in a symphony rises and falls and disappears and rises again. It is so easy to exist instead of live.
🎤 Russ Hudson: The Pursuit of Presence | The Knowledge Project
"...the idea is your temperament is what you lead with, it's how you cope with things. When the chips are down, there's a certain way you're probably going to deal with, some of us if there's a conflict we get in people's faces. Some people when there's a conflict, we go hide some people. When we're in conflict, we start brooding, but people have different reactions. And so it's it's not really about just giving ourselves a free pass about all that. It's about noticing it so that we have some options and freedom and can choose other behaviors than other than just our default..."
If I were forced to pick one personal growth tool for myself, it would undoubtedly be the Enneagram. My own Enneagram journey though is an admittedly windy, rocky and uncomfy one. For the better part of a year, I ignored my wife’s emphatic requests to take the Enneagram. Part me thinking I didn’t need the “help,” part me being too scared to accept the truth, my resistance remained strong.
Until one day, the book The Road Back to You showed up in the mail. My mother had sent all of her children a copy. I listened to mother over wife (as a formerly good-mannered southern boy) and decided to finally take the plunge. Before taking the test, I cozied into bed one night with the book and got started. I had been told by a few people that I was a Type 7 - The Enthusiast, so I jumped to that chapter. I liked almost everything I read. The positive characteristics felt good; the negative tendencies didn’t feel too bad. I ran into a conflict though when i stumbled upon Type 9 - The Peacemaker. The positive characteristics fit, but instead of feeling good about them, I felt painfully self-conscious. The negative tendencies read as painful and visceral. Unable to accept the full truth in the moment, I closed the book, slept terribly and delayed taking the test for another 2 weeks. I finally mustered up the courage to take the test, and just as my resistance had predicted, the Sorting Hat returned back: Type 9. The Enneagram has a way of projecting back not what you want, but what you need.
This Knowledge Project interview with Russ Hudson, co-founder of the Enneagram Institute, is one of the best introductions I've come across to what it is and how it can be applied. Also, if you’re curious about diving in, you can find loads of free tests online, but I’d recommend spending the $60 on this test. The results are comprehensive and actionable in ways that most of the free ones aren’t.
On how the Enneagram helps relationships:
So it gives, I think it gives a lot of couples language to talk about what's going on with them. It helps them see where they align on values and where they see things differently.
Where you find meaning:
"...the heart is where we find meaning. Meaning is not cognitive, you can argue endlessly in your head about what's meaningful, but evidence lands in your heart."
On where authentic confidence comes from:
“…confidence arises out of our relationship with our body. Like, the more I feel embodied, the more I feel I'm here, I feel like I belong here, like it's in a sense right for me to be here or I have a right to be here. And it's not an inner debate. It's not something that needs to be argued or asserted. It feels natural. So the more we're in our body, the more we're in our power.”
🎸 Spotify 2020 Wrapped
It’s Spotify 2020 Wrapped season, so I figured it was only fitting to share where I landed. Per usual, I’m all over the damn map — somewhere squarely in the middle of hip-hop, jazz and jam bands.
Here were my favorite songs of the year from these artists:
Good News / Mac Miller
Looks Like Rain - Live, February, 1978 / Grateful Dead
Blue in Green / Miles Davis
Sunny / Pat Martino
Tchfunkta / Stanton Moore
This Conan 2011 commencement speech at Dartmouth was exactly what I needed to hear this week. Conan talks in detail about his greatest professional failure and how it was the most liberating year of his life. In his own words, “There are few things more liberating in this life than having your worst fear realized.” Thanks to my buddy @Brian for surfacing this video and Conan’s “blue leather suit” moment over at Growth Snacks.
Note: If you’re looking for my favorite part, I recommend starting at 16:10 and watching to the end.
“Active Listening as a service”
Hapi is the coolest idea I’ve come across of late. Here’s how it works: You call a number. You talk to a random person, anonymously and confidentially, for as long as you want. You hang up. The company calls it “active listening as a service.” Aka, therapy.
“The way we do anything is the way we do everything.”
- Martha Beck
Y’all — that’s it, and that’s all for this week. If you made it this far (or read any of this at all for that matter), I appreciate you a whole lot.
You may have noticed that I changed the format up a bit. If you have any feedback, I’d love to hear it and am all ears. And please keep the content recommendations coming. I loved seeing some of the stuff folks sent across after the first one!
Take care 🤘,