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Daily Stoic New Year New You Challenge – Week 1 of 3

In July I took the Daily Stoic Freedom Challenge and documented my progress here. It was an interesting experience, a challenge in discipline which I found worthwhile and rewarding. So when Daily Stoic announced their New Year New You challenge I was happy to sign up and use it as a kick-start for 2020.

I wrote one blog post for each of the 21 days of the Freedom Challenge but given it proved difficult to publish daily at that time, I decided this time to condense it to a post for each of the three weeks. This one covers week one!


The Daily Stoic introduction email describe the challenge as follows:

The New Year New You Challenge is a set of daily challenges for the next three weeks, each based on the teachings of Stoic philosophy. They are designed to take you out of your comfort zone and put you on a path to the new you.

* You will learn to stop procrastinating and avoiding the change you truly desire

* You will build new habits that will create a strong foundation for change, and abandon the harmful habits that are dragging you down

* You will learn new skills that are essential for your progress in 2020

* You will strengthen your character, becoming a more virtuous version of yourself

* And above all: You will find out just how much you are capable of

Each day you’ll get an email from us with instructions for the day’s challenge. These will all be exercises and routines you can begin right now to spark a personal reinvention. We’ll tell you what to do, how to do it, and why it works. We’ll give you strategies for maintaining this way of living, not just for this challenge or for this coming year, but for your whole life. We will also include additional links and helpful resources. Each challenge will also include a video message from Ryan Holiday describing the inspiration for the challenge and further wisdom on how to use the lessons from each day in your own life.

As with the Freedom Challenge there is also a Slack group allowing communication with other challenge participants and a printable calendar to keep track of progress:

Daily Stoic New Year New You Challenge

Day 1: Watch Today’s Sunset and Tomorrow’s Sunrise

“The day has already begun to lessen. It has shrunk considerably, but yet will still allow a goodly space of time if one rises, so to speak, with the day itself. We are more industrious, and we are better men if we anticipate the day and welcome the dawn.”

Seneca, Letters From A Stoic, 122.1
The Challenge

Your challenge today is to observe this cycle: watch the sunset this evening, then get up before dawn and watch the Sun rise tomorrow.

The Theory

Go ahead right now and Google the times for sunset and sunrise. Set alarms so that you don’t forget. Identify a place with a clear view of the western horizon. Then, when the Sun sets tonight, be outside, ready to witness it all. Take in the beauty of the last light, as it ripples across the horizon and the Sun stains the sky above it with colors that feel like they don’t exist anywhere in nature other than here in this moment. Pay attention as the bottom of the Sun reaches the horizon. It’s shocking how quickly it disappears from view; one of the most significant cosmic events visible from our Earth, over in a few minutes.

Tomorrow, be sure to wake up nice and early as your spot on earth swings back around in its rotation and the Sun prepares to make its reappearance. Get your coffee set up tonight so that you can have a steaming mug ready to take outside with you when the predawn darkness begins to lighten into that steely cobalt gray color that we only used to see in our younger days when we hadn’t gone to sleep yet.

The Practice
Watching the sunset

It’s hard to convey in words the power that lies in both moments, sunrise and sunset – it’s something that needs to be experienced. The stillness, the awareness that you’re looking at the same sun that millions of others see every day, the feeling of putting to rest what has gone as it sets, and the feeling of renewal as it rises.

One thing I’m not sure of is whether the feelings fade with repetition – would the novelty wear off if stopping to watch the sun rise and set was a daily practice? I suspect, however, that doing it at least weekly wouldn’t jeopardise its impact.

Day 2: Take a Cold Plunge and Shock Your System

“The body should be treated more rigorously, that it may not be disobedient to the mind.”

Seneca, Letters From A Stoic, 8.5
The Challenge

Our task for you today: take the cold plunge. Immerse yourself in cold water; commit to half a minute of discomfort; and come out the other side stronger for it.

That’s right, the cold plunge! Just as Seneca did to begin each year, with a freezing plunge into an icy pool. Two thousand years ago Seneca described himself as the “cold-water enthusiast, who… used to inaugurate the first of the year with a plunge into the Virgo aqueduct [the present-day Trevi Fountain].”

The Theory

Challenging yourself to this kind of chill doesn’t just get your blood flowing or wash you clean. This kind of shock strengthens you. The idea behind the cold plunge is simple: You’re showing your body, you’re showing this morning, this new year, who is in charge. You’re showing everyone that you’re tough enough to handle whatever is thrown your way.

It’s a simple process: Go through your usual shower routine. Take as long as you need under the warm water—but remember, it’s not going to last forever. When you’re ready, get a timer going on your phone for 30 seconds. Then, without giving yourself time to think it through or anticipate the chill, crank the handle to cold!

Do whatever it takes to withstand the shock; even if you have to let out a scream. Listen carefully for the timer to go off. When it does, you have permission to scramble out of your tub or shower as fast as you can.

When you’re out and thinking straight again, it’s time to reflect. Think about how cold it was…and yet how after a time, your body got used to it. Reflect on how nervous you were before you jumped in. Didn’t the prospect of a cold shower seem to almost fill you with terror? Think about all the things that flooded your mind, all the things you’d rather have done instead of that, given a choice. Yet in the end, you knew that it was going to be just 30 seconds long—and you worked up the nerve, and you did it. You did it.

The Practice
Prep for an ice bath

Today’s task also formed part of the Freedom Challenge and was something I continued doing for a number of weeks after the challenge ended. The habit faded away over time, so I’m grateful for the reminder to start it again. Aside from a number of health benefits that cold therapy is known to have, the feeling of building resilience to uncomfortable conditions is an invaluable one.

Day 3: Find a Place of Isolation, Then Count to 1,000

“Stop allowing your mind to be a slave, to be jerked about.”

Marcus Aurelius, Meditations, 2.2
The Challenge

Today’s challenge is about beginning the mental training that Seneca contemplated. Your job is to find a solitary place, and slowly, quietly, count to 1,000. Without distraction. Without drifting.

To some of you that will sound easy. To others that seems impossibly hard. Forget that. Just go do it. The experience will be revealing.

The Theory

Getting to 1,000 will be a task even without distractions, so find a place free of them: No TV, no video games or computer, no cellphone, no AirPods, no anything. We want you to focus your mind and spirit for one solid session of stillness. Without outside distractions, it will be easier to concentrate on one thing and one thing only, but make no mistake: your mind is plenty good at creating its own distractions, so prepare yourself.

Once you’re ready, don’t delay; plunge in, just like you did with Day 2’s cold plunge. Count one digit per second—which adds up to a little more than 15 minutes—and don’t rush through. Don’t mentally celebrate when you get through a set of 100, or when you’re halfway through. Just keep going. Stay present. Stay on task. You’ll have to concentrate your mind on your count. Concentrate on setting an even pace. Don’t make up songs to go along with your count, don’t whistle, don’t be antsy—seek out the stillness in your mind, the stillness that you’re adding to and building up with each new second of counting.

What’s the point of all this? There is no point…and that is the point. This quarter of an hour will be one of the most present fifteen minutes of your year, possibly even your life. You will have demonstrated that you are in control. If Seneca were around, he’d envy the strength of mind you just displayed. At that point, you can get up and go about your day, confident that the sense of stillness you reached, the mental toughness you built, will stay with you.

The Practice
Something to focus on while counting

I was more sceptic about this one than Stoic when I first read the challenge email. The idea of counting to 1000 seemed potentially time-consuming and boring. When I got to around 200, I started getting fidgety. I wanted to get up from the chair and check my phone, which was in another room. Random thoughts were coming and going while I was counting but it was a strangely comforting feeling that after a thought passed the counting was still there. It was interesting too that when I got to around 600 I settled considerably and stopped fidgeting. Where I had been subconsciously trying to speed up the counting before, I consciously slowed it down at this point and was able to savour the stillness for the last few hundred.

Day 4: Pick A New Skill and Add It to Your Game This Year

“Just as nothing great is created instantly, the same goes for the perfecting of our talents and aptitudes. We are always learning, always growing. It is right to accept challenges. This is how we progress to the next level of intellectual, physical, or moral development.”

Epictetus, A Manual For Living, p.74
The Challenge

Whether in sports, business, or life, the greats are known for how they’re always looking to add a new element to their game. Today, your challenge is to do the same: Pick a new skill that you’ll add to your game this year—and then take the first step towards acquiring that skill.

The Theory

It’s 2020. We’re on the doorstep of a new era and uncertain times, what better moment to increase the tools in your toolkit, to make yourself more interesting, more employable, more cultured, more resilient, more…whatever you’d like really. And there has never been a better time in history to do it. No matter what you might want to learn, there’s a dozen ways for you to learn it.

Whether or not it’s actually critical to acquire this skill you’re interested in, what is certain is that with all the technology and freelance services at our disposal, there is no excuse for waiting any longer to learn? Watch that YouTube video, sign up for that class, hire that instructor, put your name up for that new internship, do whatever it takes to add something new to your game.

The Practice
Getting back on to Duolingo

One of the suggestions in the challenge email was getting round to picking up that second language you’ve always wanted to learn. As I’ve made a few attempts in the past to learn Italian but ultimately never got to a point of feeling comfortable enough to have a conversation, this seems like a good opportunity to try again. I already have a Duolingo account so I plan to get back on there, and I also have a Rosetta Stone course I can make use of. The challenge also recommended a service called italki, which provides access to teachers for 1-on-1 lessons, and that’s something I’ll consider too after getting back up to speed with the Duolingo lessons.

Day 5: Visit A Part of Your City You’ve Never Been To Before

“You wander hither and yon, to rid yourself of the burden that rests upon you, though it becomes more troublesome by reason of your very restlessness…As it is, however, you are not journeying; you are drifting and being driven, only exchanging one place for another, although that which you seek, – to live well, – is found everywhere.”

Seneca, Letters From A Stoic, 28.3-5
The Challenge

Today’s challenge: pick some part of your town or city or region that you’ve never visited, and go see it. Take off the blinders. Soak it in. Walk it top to bottom. Touch the walls. Eat the food. Talk to the people. Look at the wonders hiding in plain sight, the hidden gems of a place you may have otherwise taken for granted.

The Theory

Philosopher and Nobel Peace Prize winner Albert Schweitzer once said, “In the hopes of reaching the moon, men fail to see the flowers that blossom at their feet.” Home can lull us into this kind of cruise control. We become creatures of routine. Day after boring day, we drive the same roads, walk the same sidewalks, see the same faces, and slip into a Groundhog Day-like trance. How many gardens’ worth of flowers have we trampled or ignored as we went about our normal day with our head in the clouds or buried in our phones?

Our guess is, too many. So snap out of it! Get into the vacation mindset—excited to get out and explore, open to the day’s possibilities, keenly observant of what might be around every corner—but do it at home. Even in the smallest town, there are places of amazing beauty, both natural and man-made; you just have to look.

The Practice
Taking in the countryside

For today’s challenge I went for a cycle. Not for the fitness or the physical exertion as most people on bikes seem to be aiming for these days, but for the leisurely opportunity to cruise through the countryside and take in an area that I rarely frequent. It’s amazing how much more you take in when you aren’t rushing to a destination but simply taking the time to enjoy the journey.

Day 6: Write Your Personal Ten Commandments

“Say to yourself what you would be and then do what you have to do.”

Epictetus, Discourses, 3.23.2
The Challenge

Today, your job is to create your own personal Ten Commandments. What principles do you live by? What principles do you want to live by? This is the day you muster the courage to define your rules, to articulate them, and to hold yourself to them. Write down your personal Ten Commandments that describe the person you wish to be.

The Theory

These should be foundational rules, just like the Ten Commandments were to Moses and the Israelites. We’re not talking about habits or chores: brush my teeth before I go to bed, take the garbage out every night. These are rules that oblige you to be virtuous, that function as a North Star as you attempt to navigate the turbulent seas of the year to come and manage the winds of Fate and Fortune that may come from any direction at any time.

Create Ten Commandments to be looked at. Put them in a display befitting their importance. Frame your commandments and hang them on your bedroom wall or put them on your desk, a place where you’ll see them every day so you can always heed them and never run away from them. Let them be a reminder for all of 2020 and beyond of what type of person you want to be.

Sit down and answer the tough but essential questions about who you wish to be. Turn that answer into something physical, something that can be referenced and looked to. Then comes the really hard part: You have to live up to the ideals your commandments call you towards.

The Practice
A reminder of the most important one

Admittedly I’ve cheated and come up with thirteen commandments as I wasn’t able to whittle them down to ten! Here they are:

  1. Don’t measure yourself against other people’s posturing. You have no idea what goes on behind closed doors.
  2. Always have The Tail End in mind and use time with others well – particularly, don’t waste it distracted by devices.
  3. When things are going sweetly and peacefully, pause a moment, and then say out loud, “If this isn’t nice, what is?
  4. Value books over television, podcasts over social media, learning over news.
  5. If you don’t force yourself into discomfort your comfort zone will never expand. Often the thing you least feel like doing is what you need to do most.
  6. Everybody matters or nobody matters.
  7. Meet with Triumph and Disaster and treat those two impostors just the same.
  8. Don’t attribute to malice what can be explained otherwise. So someone slighted you, who cares?
  9. Learn from the past but leave it behind. Plan for the future but don’t obsess. Live in the present.
  10. Do favours. Do help. Do give. Don’t keep score.
  11. Show don’t tell, influence don’t command. Actions speak louder than words.
  12. Materialism leaves you constantly vulnerable to a world beyond your control. Know you have enough.
  13. Just that you do the right thing. The rest doesn’t matter.

Day 7: Pretend You Have To Get a New Job—Today

“What is quite unlooked for is more crushing in its effect, and unexpectedness adds to the weight of a disaster. This is a reason for ensuring that nothing ever takes us by surprise. We should project our thoughts ahead of us at every turn and have in mind every possible eventuality instead of only the usual course of events… Rehearse them in your mind: exile, torture, war, shipwreck. All the terms of our human lot should be before our eyes.”

Seneca, Letters From A Stoic, XCI
The Challenge

No matter how satisfied you are with your current life, how comfortable you are with your current employment, your current home, your current group of friends, your current routine—your challenge today is to pretend you’ve washed up in a new town and have to completely rebuild your life.

The Theory

What does that look like? Well, you’ll need new employment, a new home, a new group of friends; a whole new routine.

What job could you quickly land to buy yourself some time? Go around to local businesses—restaurants, cafes, book or retail stores—and see who is hiring. Explore all the freelance or gig economy options out there and see where you might be able to quickly secure a flow of income. This isn’t about landing that dream career job. It’s about knowing that if, in February 2020, the bottom were to fall out of the market, or the ax were to drop and you lost your job, you’d be just fine.

Once your income is sorted, we need to figure out a living situation. Find an affordable Airbnb or hostel you could camp out at while you look for something long term. Check out Zillow or Craigslist and get acquainted with apartment prices in different parts of town. You can even send an inquiry or two just to see how quickly you could lock down a place. Search Google and LinkedIn for local realtors. Reach out and tell them you’re curious what your options would look like within a price range you can afford with the amount of money in your checking account and however much money you’d ge bringing in with this new job you’ve just found.

With a job and housing taken care of, the next task is to make all that effort worthwhile. As Marcus said, humans were made for each other—to really set up a new life, you need some friends. Zweig loved writing, so he would find out where the local writers hung out, he’d show up and introduce himself, then ask if they wouldn’t mind if he joined them. Follow Zweig’s lead, and find your new circle of friends.

There are countless ways to meet new people, many of them facilitated by apps or websites. Download Bumble BFF and find people who seem cool to you. Visit and sign up for a group that shares your favorite interest. Whatever it is, the point is to show that you’re not beholden to your current circumstances—that you can reorient and reestablish yourself wherever, whenever, without any handouts.

The Practice
Checking out budgeting apps

This is a difficult one to feel motivated about without there actually being anything at stake, but useful nonetheless to do some preliminary investigation on. The result was a commitment to keep LinkedIn updated (and connect with more local recruiters on there), a resolution to keep a closer eye on my budget to know exactly what outgoings would need covered if the worst were to happen, and the motivation to meet more people from further away!