#5: On Time, Optionality, Imagination, Happiness vs Meaning & 23 Songs

(bi)weekly digest of things I'm thinking, consuming, and inspired by 🤘

Happy Wednesday Folks,

It’s been a little while since my last newsletter, so I wanted to start off with a few personal updates on my end:

• I’ve just entered Week #2 of the On Deck Writer’s Fellowship. It’s been a blast so far. The community is incredible, lots of kind and talented folks representing 6 continents 🤯, and I can’t wait to see what’s on the other end of a full 8 weeks.

• I’ve written 23 of 30 songs in what is now way more than 30 days. Make sure to check out a few of my favorites in the section below.

• I’m energized to start shifting some of my focus towards what I want to do next professionally. As you’re probably aware, I’ve deliberately thought very little about this over the last few months, but I’m excited to share more about how I’m thinking about things in the coming weeks!

• My 1-word intention for 2021 is Integrity = to be in alignment

And here’s a preview of what we’ll dive into today:

• 🤔 On How We Spend Our Time

• 🗞 The Trouble with Optionality

• 🎥 Imagination as the Path of the Spirit

• 📖 Fulfillment in a World Obsessed with Happiness

• 🎸 30 Songs in (Way More Than) 30 Days

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On How We Spend Our Time

“So, what do you do with all your time?”

I've received this question more times than I can count during my sabbatical; and it’s been tough for me to answer. If I were to respond honestly, many times the answer would be: “I have no fucking clue.” Most days I feel as if I’m scripting a masterclass in how to not spend one’s time, which has led me to this conclusion: it’s really tough to be intentional about how we’re spending our most precious asset — time.

Take last Friday as an example. My goal for the day was to get an early start and send out this newsletter. In case you’re (also) living out Groundhog Day during a pandemic, this is a quick reminder that you’re not reading this on ‘last Friday,' and here’s why that’s the case.

Scene //
Wake up. It’s 6:17am. Cloudy, sleep mask still on my head, I propel out of bed and into the living room. I start with coffee. Grind the beans, fire up the kettle and set the 4-minute timer. By this time it’s 7am, and it’s unclear what else I’ve done aside from making coffee. 

Pepper, our mini-Aussie, bounds out of the bedroom with my wife’s pink sock in mouth. Mental trigger: I need to teach her how to “Leave it!” I grab my phone and search YouTube. Zak George’s Dog Training Revolution looks like it’ll do the trick. ~15 mins later, and I’m ready to assume the role of dog trainer.

Fuck! It's almost 7:30am and I’ve yet to start my day; the original plan was to start writing by 8am. I toss on my shorts & shoes, nestle Airpods into my ears and queue up an episode of the 10% Happier podcast. Pepper and I finally emerge onto the rainy streets of San Francisco. After some pushing, pulling, treating (and shitting), we finally make it from Landers St to Buena Vista to Corona Heights dog park. Pepper is free to roam with her kin. I strike up an interesting(ish) conversation with another dog parent, and this lasts a bit longer than I’d like (note: I’m miserable at pulling myself away from these types of things).

After more pushing, pulling, and treating (note: no shitting this time), Pepper and I reverse course en route to home, while I get a fun call with my Dad. All that and we’re finally back home; it’s a few minutes til 9am. I bathe Pepper, shower myself and then we’re onto coffee round 2.

Sometime within the 4-minute timer, I find myself deep within the spiral that is a Twitter doom-scroll. I finally catch myself, having sacrificed 30+ minutes of my life that I’ll never be able to get back, frantically jump up and finish what I was originally here to do: get caffeinated. Now feeling unsettled and guilty, I finally arrive at my desk, take a seat and open up my Macbook. It’s sometime around 9:45am now.

Mental trigger: I need to shave (per what the mirror told me this morning) and I’m running low on deodorant. I immediately launch Chrome and navigate to Amazon. 30 mins and much deliberation later, the online shopping spree is a success. AA batteries (for my shaving razor) and Tom’s Mountain Spring Deodorant will be arriving at my doorstep by Sunday. I decide to spend some extra time browsing analog alarm clocks and desk timers, but I wait to pull the trigger. Time well spent. It’s ~10:30am. I’m finally starting to think about writing, and starting my day.
// End Scene

You can be sure that the rest of my day involved some combination of (more) Twitter doom-scrolling, exploring On Deck Slack channels, messaging with a few friends over text, chatting with a tax advisor and most importantly, very little writing. Which, again, means that you’re not reading this newsletter on ‘last Friday.’

While I promise (uhhh, hope?) that not every day looks like this, I’ve experienced enough of them to have come to the sobering conclusion that:

It is remarkably easy to spend our time in ways that are meaningless.

I say this with confidence because I’ve experienced this, and continue to do so on a weekly basis. I know, this is far from precise; but what I mean is spending our time in ways that are not aligned with our goals and priorities; in ways that do not elicit joy and or inject us with energy; in ways that are trivial, vs impactful; in ways that are unconscious, lack presence and invoke anxiety; in ways that are unintentional.

Or to put it another way — it’s way too easy to spend our time on trivial shit.

Chores and to-dos abide by Parkinson’s Law; they expand to fit the amount of time we allot to them. Distractions hide everywhere, in and out of sight. This is not without good intention or reason. Chores have to get done; and for some, are the source of meaning. Distractions can be welcome, and needed.

But the fact remains that we can effortlessly spend our time in ways that we didn’t intend to. In the case of my ‘last Friday,’ I planned to write and ship this newsletter, and I got nowhere close. So, why is this the case? I’m here to share a few of my observations.

(1) Our jobs provide us with structure, although we hate to admit it

"The three most harmful addictions are heroin, carbohydrates, and a monthly salary." Nassim Taleb, The Black Swan

When I decided to embark on my sabbatical, I was well aware of what I was getting: more time. I was grateful for this gift. However, I was less aware of what I was losing: the constraint placed on my time by my job.

Let me be the first to say that there are plenty of great reasons not to leave one’s job, particularly without the imminent prospect of another one. Our job provides for much more than we typically give it credit for. Things like self-worth, status, identity and social connection? 100%, whether we like to admit this or not. All this to say that when we leave our jobs, we’re giving up far more than just a stable paycheck.

What I didn’t include on the list is one of the under-appreciated provisions of our work — structure. One that I’m convinced is an aspect of our jobs that we often don’t, or don’t want to, give it credit for providing for. I still consider myself to be in this category of under appreciator, as I’ve struggled with this reality over the last few months. So much so that I’m now convinced that this is one of the primary reasons more people don’t take time off, whether this is conscious or not.

We have 112 waking hours to spend in a given week (you’re welcome, I’m generously giving you credit for sleeping a full 8-hours a night). 36% of those hours — 40 hours/week — are consumed by our jobs, and in many cases, far more than that. If you condense that to the work week only, that percentage jumps to 50%. Unsurprising conclusion: we spend a significant amount of our waking lives at work.

As a result of how much time we spend at work, we create fairly engrained schedules, systems and processes that are centered around our jobs. Here’s the typical approach: we find a job, and then we reverse-engineer the rest of our lives with the time that remains. Our jobs are the corner & edge pieces in the puzzle that is how we choose to allocate our time.

There’s nothing inherently wrong with this. Constraints are vital. Creating a life around our jobs is oftentimes a necessary and expected reality of working. But because our jobs represent such a significant constraint on our time, we can find ourselves moving into auto-pilot with how we spend the remainder of our time; and can typically get away with it.

The resulting problem: Our time management muscles atrophy, or ossify. We develop two simple modes of operating within our lives, work and non-work. Anything we do within our “work window,” in those 8 hours, from 9-to-5 becomes acceptable; anything we do outside of those hours also becomes acceptable. But when we remove this constraint, it can be both difficult and uncomfortable to regain control of the plane.

(2) Managing our time effectively is f@#$ing hard, and requires active effort

I am convinced daily that everything is conspiring against me being able to spend my time in the ways that I would like to spend it. My partner, my dog, my dishwasher, my parents, my phone, my procrastination, my local barista, my dishwasher, my successes, my failures. The list goes on. Onslaughts against our time abound and tend to lurk where we least expect them.

Here’s the predicament. Time is a gift. Quite literally the most precious gift we’ll ever receive. When we’re gifted time though, we’re also burdened with the responsibility of determining what we do with this gift. Aka, how we spend it. This burden can make us wish that we never received the gift in the first place. Which is mind-blowing when we remember just how invaluable the gift is.

It turns out that actively managing one’s time effectively(note: this is the operative word here) is no passive activity. Rather, this can feel like a full-on war. We also can’t delegate this task. We are, fortunately or unfortunately, the CEOs of ourselves, which comes with more than a little bit of risk and responsibility.

Managing that time effectively requires a bit of skill as well. It requires being simultaneously strategic and tactical; it requires the “what” and the “how”; it requires a vision and an action plan; it requires discipline and fluidity; it requires a convoluted combination of principles, strategies, systems, hacks and intuition. There’s also no “right” answer to how one should spend it, leaving many of us perpetually anxious about whether or not all our efforts are yielding any results.

(3) Managing our time effectively requires clarity around our priorities.

To make matters even worse, effort isn’t enough. Spending our time meaningfully also requires an uncomfortable precursor that is all too convenient to gloss over. We must know how we define meaningful in order to spend our time meaningfully. 

And of all the inquiries that don’t have clear paths to discovery, this one might top the list. What do I care about? What makes me tick? What brings me energy? What are my priorities? What brings me meaning? What do I value?

These are incredibly difficult questions to answer for most. And once you attempt at answer to them, you’ll be forced to ask yourself this additional question: Does the way I currently spend my time mirror what I say I actually care about? From my experience, this might require an uncomfortable reckoning with the fact that there’s a delta between what we say our priorities are and what how we spend our time says about those same priorities.

This process is not always fun.

I am (fortunately or unfortunately) not here to present any grand solutions, plans or frameworks for how to spend one’s time meaningfully. I’ll leave that for another time; and possibly a bit more experience. I am here to say though that as uncomfortable as it can be to fumble your way into an answer to what spending your time meaningfully means to you, I believe the attempt — and the effort required to put that answer into motion — is absolutely worth it. Worst case, I promise you’ll come away with a renewed appreciation for how profoundly valuable your time actually is and how little of it we actually have. I sure have.

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🗞 The Trouble with Optionality

I was hit pretty hard by this quote from Harvard professor Mihir A. Desai in his article, The Trouble with Optionality:

The shortest distance between two points is reliably a straight line. If your dreams are apparent to you, pursue them. Creating optionality and buying lottery tickets are not way stations on the road to pursuing your dreamy outcomes. They are dangerous diversions that will change you.

We’re all familiar with the concept of optionality. When faced with a choice or decision, choose or decide based on what results in more future options. The advice sounds reasonable, even rational, and is what we’re often taught as a model for how to move through the world. In his article though, Desai wisely cautions against pursuing optionality for the sake of optionality and reminds us of the hidden cost of this strategy: the directions we move in change us, whether we’re consciously aware of that or not.

I found myself stewing on a few questions after I read this article: Where am I optimizing for optionality in my life right now? Is that optionality moving me closer, or further away, from seeking my dreams in those areas?

Read It: The Trouble with Optionality

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🎥 Imagination as the Path of the Spirit

It takes a lot for me to reread or listen to something. It takes a miracle for me to do this within the span of 12 hours. This lecture from Irish poet, author, Catholic priest and philosopher John O'Donohue was that miracle.

There’s an ungodly amount of wisdom in here, so I haven’t even attempted a comprehensive summary. Below are a some ideas that stuck with me:

• What are the 7 thoughts that rule your mind?

• The best way to change your life is to change how you think

• The greatest “sin” = the unlived life

• We only change when the prospect of not changing is more painful than changing 🤯

• What it means to “live into” your life

I owe an eternal thank you to @Alex for this recommendation, and I strongly recommend a listen, or two. Fun fact: O’Donohue was the best friend of David Whyte, the author of my favorite book of 2020.

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📖 Finding Fulfillment in a World Obsessed with Happiness

There are sources of meaning all around us, and by tapping into them, we can all lead richer and more satisfying lives – and help others do the same.

Meaning vs Happiness. Are these the same, and if not, which one should you choose? In the book, The Power of Meaning, I’ll let you guess which side of the debate Emily Esfahani Smith takes on this. This book was a much-needed reminder for me that chasing happiness or optimizing for that next dopamine hit is rarely the best path; and that it’s typically the things that require the most effort, are the least expected and are all around us that we really desire.

I found this book both entertaining and well-written, researched and argued. Smith does a masterful job of weaving in various perspectives to construct her argument: from philosophical musings of literary greats to real-world examples to academic research.

Below were some notable takeaways for me:

• There is a distinction between a happy life and a meaningful life

• Meaning is not found; meaning is created — the sources of meaning are all around us

• 4 pillars of meaning: belonging, purpose, storytelling, and transcendence

• Why it’s important for to learn to “suffer well”

Tip: If you're looking to dust off your library, you should consider trading old books in for credit at a local bookstore. My wife and I recently did this as part of the Marie Kondo process and that’s how I came across this book. Please note that the verdict is still out on whether or not this defeats the purpose of Marie Kondo.

Read It: The Power of Meaning: Finding Fulfillment in a World Obsessed with Happiness

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🎸 30 Songs in (Way More Than) 30 Days

Yes, my dog did eat my recording headphones. No, this has not completely stopped me from writing music. Scoreboard: I’ve written 23 songs in what is now way over 30 days. You’ll even notice that a few songs have lyrics.

And while I’ve deliberately slowed down my musical creation rate (to focus on other priorities like the On Deck Writing Fellowship), don’t you worry — I’m still planning to reach my 30 song mark. You can catch some of my recent favorites below and find even more tunes on my Soundcloud when you need your fix.

Good Girls — lyrics inspired by a glorious hike on Mt. Tam’s Dipsea Trail:

Fly Fresno — if you’re into fly and funky beats:

Get Up & Dance — my attempt at writing a disco banger:

BONUS: Check out this cover of It’s All Right featuring my sister Beverly’s 🔥🔥🔥 vocals (you know, the song originally by The Impressions and the final song in Pixar’s Soul). Thank you in advance for your support in officially and publicly embarrassing her. You’ll notice that the vocals (by her) are far better than any other aspects of the song (by me). This one definitely needs some production work, but 👏👏👏 to Bev’s debut!

Listen: My Soundcloud

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That’s it, folks! Thank you, thank you, thank you for reading this far, or for reading any of this at all. Every (bi)week I think this newsletter will be shorter, but somehow it’s managed to elude me every time. What can you do?

🤘,
Harris