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Stoic Inspiration: Exercises to Get You Started & Entrepreneurs Who Practice It

Feb 27, 2019 | Posted by Cristina in Newsletters

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The text below was sent in February 2019 as part of our weekly newsletter. If you enjoy it and want more similar emails delivered straight to your inbox, subscribe here.

Four or five years ago, I discovered stoicism, an ancient Greek philosophy developed a few centuries B.C.

I had just finished reading Ryan Holiday’s first book and dived into his blog archive, where he talked about how reading a stoic book when he was in his first college year has changed his life. It became a “quake book” – one that shook everything he thought he knew about the world.

Obviously, I was curious to learn more. That’s when I headed down the rabbit hole of stoicism, reading all the articles and books I could get my hands on. I was hooked. It led to a paradigm shift that made me wish I had read all those a long time ago (same reaction as when I discovered Nassim Nicholas Taleb‘s words).

Stoicism is a practical, down-to-earth philosophy, with evergreen principles that can be helpful in today’s stressful environment. Practicing its principles has made me less anxious, more calm and content (don’t get me wrong, it’s a neverending process, like training your muscles: you can’t go the gym 3 times per day in January and expect the results to last the rest of the year).

One of its basic principles promotes making a clear distinction between things that are under our control and those that are not. This type of detachment reframes your perspective: instead of emotionally reacting to all the things that you can’t influence, such as what other people do or think, you’ll be more focused on things that you directly control.

Here’s one of the examples of how I applied this to building The CEO Library. Back in 2017, when we had just started the website, we wanted to publish at least one interview with an entrepreneur per day, every day of the week, to see how much it contributes to the growth of our project.

I’m talking about doing cold outreach, emailing highly successful and busy entrepreneurs, who live in different corners of the world and from different cultures, and asking them to share how their favorite books shaped their journey – a topic that requires a lot of time and energy from them.

Since it’s not under our control whether people accept our invitation, we focused on something else: to be the best at researching and reaching out to 30 leaders per week. That was our target.

Doing a thorough research and writing personalized emails increased our odds. Half of the entrepreneurs we approached accepted our invitations from the first contact, and most of the rest replied after the follow-up email (well, sometimes there would be multiple follow-up-emails, depending on how much I admired them 😀 ).

By focusing on the lead measures, we hit an 80% success rate, which is almost unheard of when it comes to doing cold outreach.

Eventually, we readjusted the frequency and settled to publishing only one new book-talk per week, as we were producing a huge quantity of valuable content that was hard to keep up with, but I digress.

Two basic stoic exercises that you might find valuable in your day-to-day life:

1. Practicing negative visualization.

The core idea of the negative visualization exercise is to imagine all the bad things that could happen in your life, such as losing a family member or a friend, being ill, losing all your possessions in a fire, etc.

We’ve gotten so used to the way things are, what we have, our relationships and so on, that we start taking them for granted and become complacent. This exercise can help us be more grateful and remind ourselves that we’re damn lucky.

You can also apply this in your career decision-making process or when you’re planning a new project at work.

One year ago, I attended an event where Iulian Stanciu was interviewed (he’s the CEO of eMag, the biggest Romanian online retailer). At some point, he talked about how his business is preparing for the moment when the biggest players in the world (especially Alibaba group) will enter the local market. Will this save his business when that happens? Nobody can know. But it surely increases the odds to survive and at least he’ll be able to say that they did everything that was in their power, instead of complaining.

Here’s another stoic-inspired exercise that you might relate to more: if the traffic is bad because of the weather, no amount of yelling, cursing and stressing about it will change the way things are.

What we can do instead is visualize in advance the way things could go wrong and take the appropriate measures. In this case, leaving earlier to beat the traffic, or putting on a raincoat and taking public transportation. Or just accept the situation and try to turn it into something productive, such as using that time to listen to a new audiobook or make some phone calls you’ve been postponing.

Ask yourself what’s the worst thing that could happen. Define those fears and risks, and figure out what you can do to build a moat and prevent them from happening.

2. Staying uncomfortable

This one’s the physical version of the exercise described above: stay uncomfortable. Do limited-time experiments where you cut out things that you take for granted. The purpose is to be prepared in case we actually have to face physical hardships and sh*t hits the fan.

Here are a few examples how you can stay uncomfortable:

– Drinking only water for some set period of time (most religions have some sort of fasting included in their rituals). I’m sure you know a lot of people who are always hangry (hungry + angry 😛 ) if they don’t eat for ~2 hours, although the human body can easily go for days without food.

– No coffee for one month. I’ll tend to get cranky if I don’t see coffee first thing in the morning, so, from time to time, I’ll just cut it off completely. I do this whenever I feel like I’m becoming too dependent on it. It also makes me appreciate the taste more afterwards.

– Taking cold showers or going out in the winter without wearing a jacket. I’ve been doing this ever since I was a kid and I remember how the grownups were always outraged. I had no idea back then (it was just another stupid way to reject authorities), but exposing myself to the elements made me more resilient. Running in the park during cold winter days has the same effect.

As humans, we’ve been on an evolutionary path for a few million years, dominated by two challenges: cold stress and calorie scarcity. It was only in the recent years that we solved both. We’re keeping ourselves comfortable, warm and safe in a cocoon of technology, and forget that our bodies are built to endure the natural variations of our planet.

Please note that this is not an invitation to do anything stupid – there’s a clearly defined line between a little cold versus doing things that aren’t safe. It’s one thing to expose yourself to cold when you can always just call a cab and go home, or enter the nearest coffee shop to warm up, and it’s a completely different thing when you go for a trip in the mountains, where you can see a radical weather change in just a few minutes and your life is under threat. You don’t mess with that.

– Staying without your phone for a whole week. Gee, I wonder how our parents ever survived without being permanently connected.

– Walking everywhere you go instead of taking your car (don’t know about you, but I’m living in a city where owning a car is way too affordable).

– No eating out at restaurants or buying new clothes for a few months.

– Josh Waitzkin was describing in his book how he’d train under the worst conditions: playing loud, rock music, or in noisy parks, and so on, in order to simulate the difficult conditions that helped him perform under pressure later. Josh is one of the biggest American chess icons (8 time National Chess Champion), a martial arts champion (several National and World titles in Tai Chi Chuan and Brazilian Jiu-Jitsu), and has written what I consider to be one of the best books about how to learn.

So, in case you were wondering why I always refer to stoicism or Ryan Holiday’s articles in these newsletters, now you understand. 😛

If you want to learn more about stoicism and don’t know where to start, these are two books that I’d recommend:
1. The Obstacle is the Way
2. Marcus Aurelius – Meditations

P.S. keep scrolling for more awesome stoic resources.


1. Stoicism And Digital Minimalism: An Interview With Computer Scientist And Bestselling Author Cal Newport
Still waiting for my Amazon order of Cal Newport’s new book. In the meantime, I’m enjoying his media tour materials and all the interviews that have been released these days. I especially loved what he says in this interview for the Daily Stoic (one of Ryan Holiday’s projects and the only daily newsletter I’m subscribed to). Here’s an extract:

The other reason that seems to keep people glued to their screens is that it fills a void. Life is hard. This hardness is especially manifest during those periods of downtime when you’re alone with your thoughts. People avoid these confrontations through constant, low quality digital distraction much in the way that people of another era might have dealt with these difficulties with heavy drinking. But this is just a bandaid over a deeper wound.

2. David “DHH” Heinemeier Hansson: The Entrepreneurial and Unstoppable Stoic

An oldie but goldie: a great interview with one of my favorite thinkers and stoics in the world, David Heinemeier Hansson, co-founder of Basecamp, the successful software company that recently turned 15, and co-author of the book ‘It Doesn’t Have to be Crazy at Work‘.

3. Twenty-First Century Stoic — From Zen to Zeno: How I Became a Stoic

An essay by William B. Irvine, author of one of the best modern books about stoicism, where he explains what some people might misinterpret about stoicism. Here’s a short quote:

When they hear about negative visualization, people often get the wrong idea. They think the Stoics advocate that we spend our days dwelling on all the bad things that can happen to us. This, of course, would be a recipe for a miserable existence. What the Stoics in fact advocate is not that we dwell on bad things but that we contemplate them, a subtle but important difference. They also recommend that we engage in negative visualization not constantly but only a few times each day and for only a few seconds each time. Our negative visualizations, then, will take the form of fleeting thoughts.

Visualizing in this manner has the effect of resetting the baseline against which we measure our happiness, and it can have a profound and immediate effect on that happiness. As the result of negatively visualizing, we might find ourselves taking delight that we still possess the things that only moments before, we took for granted, including our job, our spouse, our health — indeed, our very existence.

4. Why you should define your fears instead of your goals

I saved the best for the end. This TED talk was given two years ago given by best-selling author, entrepreneur, investor and podcaster Tim Ferriss. He talks about how stoicism has saved his life. Many years ago, he was navigating some dark waters, considering suicide, and practicing stoicism has helped him overcome his fears.

I’ve been sending this to everyone I know who deals with panic attacks, anxiety and depression. His talk with doctor Peter Attia is also amazing, if you want to dig deeper into details.

5. Serial Entrepreneur Brian Scudamore on Digital Detox and Books That Made a Difference in his Entrepreneurial Journey

This is our recent interview. We talked to Brian Scudamore, founder and CEO of O2E Brands (comes from ‘ordinary to extraordinary’), the banner company for 1-800-GOT-JUNK?, and many other successful businesses.

His entrepreneurial path started in 1989, when he noticed a pickup truck advertising a junk removal service. He decided to start his own junk removal small business to pay for college, invested $700 from his savings to buy a truck, and founded ‘The Rubbish Boys’ (tagline: “We’ll stash your trash in a flash!”). Brian went on to pioneer the professional junk hauling industry and conquered the market.

In 1997, although ‘The Rubbish Boys’ hit $1 million in revenue, his team wasn’t the right fit for the company, so he laid-off the entire staff and almost started from scratch. He hired a team who shared his goals and vision, adopted the motto: ‘It’s All About People’, and also changed the name of his business in ‘1-800-GOT-JUNK?’. Since then, the company experienced considerable growth.

He’s gone on to successfully apply the business formula to the painting, moving, and home-detailing industry. Brian founded WOW 1 DAY PAINTING, a service that paints the house in one day (obviously?), the moving house service You Move Me, and Shack Shine, a house cleaning service. All these were built under the umbrella company O2E Brands (‘Ordinary 2 Extraordinary’).

Last autumn, Brian released the book “WTF?! (Willing to Fail): How Failure Can Be Your Key to Success”, where he shared his failures and lessons learned on the entrepreneurial roller coaster.

When he’s not working, he’s biking or spending time with his family in Vancouver, where he’s based.

From our book-talk you’ll learn more about he enforces a “going dark” vacation policy in his companies, his struggle with ADHD, the one book that helped him successfully scale his businesses, tips for first-time entrepreneurs on how to handle the need to be in control, and more. Read the full interview with Brian here.

End note:

I’m working on a guide on the topic of stoicism. If you’re practicing stoic exercises in your day-to-day life and want to share your experience with others, I’d love to include your thoughts! They might be life-changing to others. Just write a few paragraphs about it, hit reply to this email and send ’em over 🙂

Till next week. Stay uncomfortable.

– Cristina

The text above was sent in February 2019 as part of our weekly newsletter. If you enjoyed it and want more similar emails delivered straight to your inbox, subscribe here.

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