Good morning,

How have you been?

Here’s what’s in today’s issue:

• One big thing. Momentum is a strong force, and time flies. Find out how tiny decisions to reset your thinking can change your life’s trajectory in big ways.

• You have to check this out. The power of entropy and the fantasy of to-do lists.

• Tools and tech. Let your heart be your guide. Literally.

Let’s jump in.

1️⃣ ONE BIG THING

Choosing to begin again.

When was the last time you experienced the liberating joy of a workday free of meetings?

Imagine it’s a Friday morning. A glance at your calendar: empty. A to-list check: nothing that can’t wait until next week. A look around: the house/office/jobsite is empty.

The day is yours.

Two weeks ago, I woke up to just such a day. I drank my coffee. Oh, the possibilities. This day is mine.

I set an ambitious plan for the day and got to work.

Then it hit me.

As the morning unfolded, an unwelcome heaviness settled over me. Despite a night of restful sleep and the allure of my work, inspiration eluded me. My mind wandered. I felt weighed down.

I took a quick break for some food and another coffee. Maybe a quick reset, and I'll be right.

No luck. I just didn't have it. No creative juice, no spark. I heard a faint snicker. Was the universe laughing at me? Well damn. Maybe today just isn’t my day.

Just begin again.

Around 3 o’clock that day, I recalled a recent guided meditation from the app Waking Up.

I’ve edited this down for brevity, but hearing this idea directly from Sam Harris is wiser than my trying to paraphrase it:

“When we practice meditation, one of the things we learn is how to begin again in each moment.

“Let's say you notice you're distracted, and rather than just observe the next sound or sensation, you're immediately plunged into self-judgment. You're annoyed. You subscribe to this damn app, and you're supposed to be meditating, but you just spent the last five minutes thinking about something you saw on television last night.

“But you can break this spell and begin again at any point by just noticing self-judgment and frustration as appearances. And there are literally hundreds of opportunities each day to practice it.

“If you notice that a conversation with a friend, or a family member, or a colleague isn't going very well, or you're not having fun at a party, or you've been trying to get some work done, but you found that you've just wasted the last hour on the internet, or you're working out in the gym, but you haven't been making much of an effort.

“The moment you notice this ghost of mediocrity hovering over the present, you can fully excise it just by beginning again and then fully commit by relinquishing the past.

“There's no real reason why the next 10 minutes in the gym can't be the best you've had in years. There's no real reason why you can't put this conversation that's almost over on a new footing by saying something truly useful.

“So, the practice is to stop telling ourselves a story about what has been happening and to fully connect with experience in this moment. Notice this present thought, this fear, this judgment, this doubt, this desire to be elsewhere as an appearance in consciousness, and then just begin again.”

As I mentioned, at 3 o'clock, I remembered this idea: begin again.

Seven hours of the day, once so full of promise, had evaporated. I decided to head out for a walk. As I walked, I passed a tree barren of leaves, still in the grip of winter. I pulled a limb toward me for closer inspection. Tiny buds were emerging from every branch. How do the trees start doing this simultaneously, as if following an orchestral conductor?

I looked up into the trees to hundreds of red-wing blackbirds.

I must tell you that this short moment of observation and appreciation made my day. The day that started with so much promise ultimately delivered, if in an unexpected way.

Now, I can imagine this warm and fuzzy sentiment probably seems like the typical nudge to observe small beauty and feel gratitude. And sure, that’s a fine idea.

But that is not my intent here.

My day turned when I chose to begin again.

We live our lives in units of time.

In my newsletter, Two Selves on Vacation, I explained that we live in continuous, present-tense moments.

Experts say the “psychological present” is about three seconds long. This is the unit of time we experience as "now." Two units of "now" just flew by as you read that.

Over 10 million such tiny windows of "now" fly by in a year. We do not give any real thought or remember 99% of them. C'est la vie.

Consider for a moment the units of time that most of us use to time (and remember the past): a day, work week, weekend, month, quarter, season, year, decade, and season of life.

Other units of time work similarly: the window of time you live in a house or a city, spend at a job, raise your kids, are in a relationship, are ill, are in college, etc.

As Sam Harris mentions, smaller units of time work this way, too: a conversation, a meal with friends, a workout, a meeting, a date, a trip, a commute, a walk, etc.

All of these units of time have "begin again" opportunities within them (except the three-second experience of now unless you are The Flash).

To take advantage of these, you must (1) be conscious of the opportunity and (2) choose to begin again.

Fresh starts versus beginning again.

You already have some built-in tendencies to begin again, but they are needlessly limited.

Behavioral scientists know that people are more likely to tackle meaningful goals or form new habits at the start of a day, week, month, or year, which they call the Fresh Start Effect.

This explains the curious phenomenon of New Year's resolutions. For reasons that appear arbitrary when you think about it, we believe that only these special calendar days (January 1, Monday) give us magical permission to set aside the momentum and misgivings of the past and start fresh.

As you have heard or experienced, most New Year's resolutions fail (80% fail by February, 92% by the end of the year).

But these fresh starts are functionally different from the choice to begin again. They do share the conscious choice to set aside the burden of the past. But New Year's resolutions collapse under the weight of grand, all-or-nothing ambitions launched with unrealistic goal setting and flawed implementation.

I find the choice to begin again far simpler: choose to unplug from the past (which can mean the past five minutes or the past five years), reset, and do something that signifies a choice to veer left rather than right at a fork in the road. That’s it.

If you don’t make that choice, momentum simply extends the trends of the past into the future. An uninspiring day concludes without inspiration; a shallow dinner conversation wraps up without depth; a month, a year, and a decade fly by, looking much like the ones that preceded them.

Life is the ultimate unit of time.

If you have a flat, disappointing day, it's fine. There is always tomorrow.

Not so with life.

As I've written, the number of weeks in the average life = 4,000.

Of course, the number of lives = 1. No do-overs.

In this context, the simple idea of choosing to begin again is powerful. If you don’t get a second chance at life, then the only way to reorient its trajectory is to choose to begin again somewhere along the way.

The key idea is making a conscious choice. Without this, momentum and entropy will dictate how your life proceeds from today to its conclusion.

Momentum suggests your past direction will determine your future path.

Entropy is the natural tendency for things to become less organized over time. If you build a sandcastle, it will not get more sandcastle-y over time or even stay the same; it will fall apart. If you clean your house, it tends towards disorder the moment you are done.

In some aspect of your life, choosing to begin again is simply a tiny choice to turn the steering wheel slightly to the right at an off-ramp rather than letting the self-driving influence of momentum continue to take you down the interstate.

Life decisions are expected in your early years.

Think back to your time in high school or college. Your life didn’t have much shape. What type of career would you have? Will you build a family of your own? What hobbies or interests will reflect your identity? Will you become the type of person who travels the world or someone who revels in local connections and culture?

During these years, you invest energy into becoming. You decide what type of sandcastle to build and invest time and effort into building it.

This happens in part because of necessity—you need to leave the nest. It also happens because of cultural expectations. As I described in my newsletter, Your Cultural Life Script, we all absorb the cultural understanding that a life proceeds by leaving home and establishing your own identity.

The type of person we decide to become is an act of creativity.

But the decision to make these decisions is not. It’s what everyone does somewhere between 15 and 30.

Choosing to begin again is an act of creativity.

At your age, as a member of Gen X like me, however, it would indeed be an act of creativity to choose to begin again in some small way.

Here is an important distinction: I do not mean starting over. In my analogy of driving down the interstate, starting over would mean making a U-turn, returning to the starting line, and doing everything over again.

In the context of mediation, Sam Harris does not mean quitting the meditation, coming back 30 minutes later, and starting over. His idea is simply: if you find yourself six minutes into a ten-minute meditation and realize you have been distracted, you can choose to begin again and make the final four minutes great. 20 minutes into a 30-minute lackluster gym session, you can choose to begin again and make the final 10 minutes the best gym workout of the year. It’s up to you.

Let me share one of my all-time favorite drawings to illustrate this point.

This is from Tim Urban, the brilliant author of the blog Wait But Why, in an article he wrote for the New York Times in the aftermath of COVID.

Once we leave our 20s, our natural tendency is to think your life is, well, your life. It is what it is. You made a series of decisions earlier in life, and now you’re an actor in that play written decades ago.

But there is no reason you can’t choose, at any moment, to make a small decision—to veer left instead of right—that will alter your path.

Let’s get creative for a moment.

First, let’s acknowledge that creativity thrives within boundaries, not the opposite.

At 52, am I going to become a NASA astronaut? No. Am I going to become the home-run leader of Major League Baseball? No.

But how about this one? Could I become a successful lawyer, even though I've never attended law school? Oddly enough, absolutely. I could study for the LSAT, get a solid score, and then apply for, attend, and complete law school in four years. I would be 56. I could practice law for 20 years and retire at 76.

Atypical? Of course. But if someone close to me suffered a great injustice and I decided to right just a few of these wrongs, a twenty-year career doing that would be entirely meaningful.

Now, as it stands, I do not want to be a lawyer. You probably don’t either. And in general, as I’ve contemplated the idea of choosing to begin again, I haven’t focused on this type of grand ambition. I think this type of grand thinking suffers from the flaws of most New Year's resolutions: too all-or-nothing, all vision, and no realistic implementation plan.

But perhaps some more examples might jolt your creativity.

A “begin again” idea bank.

Here is a totally random list of ways you could choose to begin again. These surely are not recommendations. They are meant to inspire your thinking.

Here is an important distinction: this is not a bucket list. This isn’t a list of crazy things to do before you die so you can say you “truly lived.” I don’t buy that concept.

This is a list of ways you could choose to alter the trajectory of your life, small and large.

Here’s what I mean: Imagine, as a child, you were really into dance. You imagined being a professional dancer. In your 20s, you got a job, started a family, and stopped dancing. When you turned 40, you considered returning to dance but figured you were too old. Fast forward and imagine being 80. At 80, I can very much imagine you thinking: Damn, I could have started dancing again 40 years ago. I would have been able to enjoy this thing I love for half of my life.

Many of these ideas tackle questions of identity. In midlife, we can get stuck in an identity rut. “I am the type of person that…” or “I have never been the type of person that…”.

Your identity is far more malleable than you imagine if you choose to begin again.

• Return to something you loved as a kid.

• Live abroad for a year.

• Start talking to strangers.

• Spend more time with close friends (near and far).

• Shift your default setting from grumpy to cheerful.

• Become a writer.

• Start camping and stargazing.

• Stop drinking.

• Stop saying “I’m sorry”.

• Become a certified instructor.

• Put your phone away when your friends or kids are around.

• Become a mentor.

• Sell your house and buy a Sprinter van.

• Be the most stylish person in every room.

• Learn a language.

• Become a morning person.

• Become a lawyer (lol).

• Reinvent how you show up in friendships.

• Change your posture.

• Become a gym person and transform your physical self.

• Be a regular dinner party host.

• Completely change your career.

• Get a college degree.

• Change your default reaction to “How are you?”

• Become someone who takes on extreme challenges.

• Join a subculture.

Enjoy your day. Thanks for reading.

See you next Sunday.