The Perfect Day Begins with a Good Evening

by Ryan Holiday

All the talk about morning routines makes it easy to overlook that a good morning is impossible without a good evening.

I am reminded just how essential a good evening routine is as I write this from an RV in Balmorhea, TX – as I drive across the country to do some media for my new book, Courage is Calling: Fortune Favors The Brave.

It was one of Seneca’s observations – that nearly everything in life is circular: there’s an opening and a close, a start and a finish. Life, he says, is a collection of large circles enclosing smaller ones. Birth to death. Childhood. A year. A month. “And the smallest circle of all,” he writes, “is the day; even a day has its beginning and its ending, its sunrise and its sunset.”

To the Stoics, every day was to be lived as if it closed the story, every night ended as if it was the last night we had. They’re right. How we close out the day matters. The decisions we make. The reflection we encourage. The time we drift off to sleep. All of it is about finishing well…because then and only then can we start tomorrow better too.

What does a good evening routine look like? Whether I’m home or on the road, these are the 9 things I try to do every evening. Each is rooted in the wisdom of the ancient Stoics and when applied, as Seneca said, “let us go to our sleep with joy and gladness.”

Make Time for Leisure

The opposite of work is not laziness or lounging around, it’s leisure.

In the ancient world, leisure meant scholé. School. But not the get good grades and “get ahead” kind of school. No, in the ancient world, it meant learning and studying and pursuing higher things to enrich one’s soul and spirit.

Seneca wrote thoughtful letters to friends. Zeno gathered at the Stoa Poikile to discuss ideas. Marcus Aurelius attended philosophical lectures. My family reads together.

Marcus said it was a requirement to “Give yourself time to learn something new and good, and cease to be whirled around.” And as Seneca wrote in his essay On the Tranquility of the Mind, “We must be indulgent to the mind, and regularly grant it the leisure that serves as its food and strength.”

After indulging the mind, you’ll have worked up the appetite to…

Enjoy a Philosophical Dinner

Some people watch TV at dinner. Some people eat at their desk and answer emails between bites. Some people eat as fast as they can so they can get back to work.

In The Learned Banqueters, written just after the time of Marcus Aurelius, we learn that the sixth Stoic scholarch Antipater routinely invited friends over for dinner and long discussions about philosophy.

A few decades after Antipater, Cato would become famous for his philosophical dinners. Even his last meal – before his famous suicide – he was debating the very implications of life and death, good and bad, at such a dinner.

More recently, the philosopher Agnes Callard told me on the Daily Stoic podcast that she, her husband, and her children have philosophical debates over dinner. The topics range from serious to silly, but it’s the activity itself that really matters. It’s that for an hour or two every night, she is not doing anything but connecting with the people she loves.

…Seneca said, “let us go to our sleep with joy and gladness.”

My kids are younger, so our dinner discussions range from silly to sillier. But again, it’s the time together that really matters.

After filling up our stomachs, it’s time to…

Go for a Walk

After a meal, but before it’s dark, it is a wonderful time to get active.

Seneca wrote about taking a walk outdoors as a kind of medicine. In a notoriously loud city like Rome, peace and quiet would have been hard to come by. The noises of wagons, the shouting of vendors, the hammering of blacksmiths – all filled the streets with piercing violence. So Seneca said, “We should take wandering outdoor walks, so that the mind might be nourished and refreshed by the open air and deep breathing.”

Marcus Aurelius too talked about the cleansing effects of a walk in nature. On his evening walks, he liked to take a moment to look up at the stars to “wash off the mud of life below.” Freud was known for his walks around Vienna’s Ringstrasse after his evening meal. David Sedaris likes to take nighttime strolls on the back roads of his neighborhood in the English countryside and pick up garbage. Dan Rather talked about how “One of my favorite things long has been taking a leisurely stroll with wife Jean at twilight time.”

When we’re home, we get the kids in the stroller and do as much as three miles on the dirt road around our house, or in the backwoods and pastures on our farm. We see rabbits and deer and cows and armadillos. We stop and pet the donkeys. Like Sedaris, we pick up garbage. These are some of the very best moments in life. When it’s quiet. When we’re fully present and there. When we’re around people we love. As Rather said, “I gently recommend it. Just walk slowly in the time after the sun sets and before night descends.”

Once back from a walk, we…

Tuck the Kids In

Not everyone has kids, but everyone can learn from this exercise. Marcus Aurelius, borrowing from Epictetus, tells us that…

As you kiss your son good night, whisper to yourself, “He may be dead in the morning.” Don’t tempt fate, you say. By talking about a natural event? Is fate tempted when we speak of grain being reaped?

What is the point of this morbid exercise? It’s not about trying to reduce the affection you feel for the people you love. It’s not about preparing for the pain of losing a child (nothing can prepare you for that). It’s about not wasting a single second of the time you do get with the people you love.

A person who faces the fact that they can lose someone they love at any moment is a person who is present. Who loves. Who isn’t rushing through moments. Who doesn’t hold onto stupid things.

Marcus lost 5 children. 5! It should never happen, but it does. There’s nothing we can do about that. We can, however, drink in the present before we…

Review the Day

Winston Churchill was famously afraid of going to bed at the end of the day having not created, written or done anything that moved his life forward. “Every night,” he wrote, “I try myself by Court Martial to see if I have done anything effective during the day. I don’t mean just pawing the ground, anyone can go through the motions, but something really effective.”

The greats – they protect their sleep because their best work depends on it.

In a letter to his older brother Novatus, Seneca describes the exercise he borrowed from another prominent philosopher.

“When the light has been removed and my wife has fallen silent,” Seneca wrote, “I examine my entire day and go back over what I’ve done and said, hiding nothing from myself, passing nothing by.”

Every night, Seneca sat down and forced himself to questions like these:

What bad habits did I cure?

What temptations did I resist?

In what specific way am I now better than I was yesterday?

Success and happiness require self-awareness. Self-reflection. Be unflinching in your assessments. Notice what contributed to your happiness and what detracted from it. Write down what you’d like to work on or quotes that you like.

Writing, analyzing, reflecting, interrogating, taking inventory of how you spent the day – this is how you continue improving. Asking yourself questions. Questioning every experience, every day.

Did I follow my plans for the day? Was I prepared enough? What could I do better? What have I learned that will help me tomorrow? These simple questions make an enormous impact. So I spend some time every night answering them.

After this reflection, my evening routine is drawing to a close. It’s time to…

Count Your Blessings

This is another exercise from Seneca. He said we should wrap up each day as if it were our last. The person who does this, who meditates on their mortality in the evening, Seneca believed, has a super power when they wake up.

“When a man has said, ‘I have lived!’” Seneca wrote, then “every morning he arises is a bonus.”

Think back: to that one time you were playing with house money, if not literally then metaphorically. Or when your vacation got extended. Or that appointment you were dreading canceled at the last moment.

Do you remember how you felt? Probably, in a word – better. You feel lighter. Nicer. You appreciate everything. You are present. All the trivial concerns and short-term anxieties go away – because for a second, you realize how little they matter.

Well, that’s how one ought to live. Go to bed, having lived a full day, appreciating that you may not get the privilege of waking up tomorrow. And if you do wake up, it will be impossible not to see every second of the next twenty-four hours as a bonus. As a vacation extended. An appointment with death put off one more day. As playing with house money.

And now, as the day comes to a close, it is time for the most important part, to…

Go to Bed at a Set Time

All the other habits and practices listed here become irrelevant if you don’t have the energy and clarity to do them. What time you wake up tomorrow is irrelevant…if you didn’t get enough sleep tonight.

One thing every parent knows is that kids are a mess when they don’t sleep. But for some reason, we think we’re different. We think we can get away with pulling an all-nighter here and there. We think we can substitute stimulants for sleep.

Nonsense.

We only have so much energy for our work, for our relationships, for ourselves. A smart person understands this and guards their sleep carefully. The greats – they protect their sleep because their best work depends on it. The clearer they can think and the better their mental and physical state – the better they perform. In other words, the more sleep, the better.

The philosopher and writer Arthur Schopenhauer used to say that “sleep is the source of all health and energy.” He said it better still on a separate occasion: “Sleep is the interest we have to pay on the capital which is called in at death. The higher the interest rate and the more regularly it is paid, the further the date of redemption is postponed.”

Me? I get my 7-8 hours every night. Sleep is one of the most important parts of my work routine, period. All-nighters are for people who don’t know how to plan, who put things off to the last minute.

If you want to be great at what you do, start going to bed earlier. Give yourself a bedtime that you honor and respect and enforce. Value sleep. Take care of yourself. Put yourself in a good spot to…

Start Again

As I say in the title of this piece, the perfect day begins with a good evening. A good evening routine is just priming us to have a great day – there is still work to be done when we wake up. It’s for a reason that one of our fifty rules for life from the Stoics is “own the morning.” Well-begun is half done, as they say. Fortunately, the Stoics – in their writing and in their example – left us even more wisdom on what a good start to the day looks like.