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How Ryan Holiday Optimizes His Productivity

Ryan Holiday is a best-selling author and media strategist who found himself drawn to the concepts of marketing and ancient philosophy. Dropping out of college at age 19, Holiday has since released seven books, becoming a trusted voice in the two very different worlds. He’s the ex-marketing director at American Apparel (causing a bit of a stir) and deeply interested in stoicism, inspiring a few of his books including The Obstacle is the Way, The Daily Stoic, and Ego is the Enemy.

Holiday has gathered timeless truths and effective habits for staying productive from his readings and valued mentors, most notably the author Robert Greene, while maintaining his own creative agency advising clients like Google and TASER as well as authors Tim Ferriss and Tony Robbins.

Holiday’s Habits for Staying Productive and Gaining Wisdom

In various interviews, Holiday talks about waking up early and taking his time in the morning. He’ll always finish a workout and spend time with his son while his wife catches up on sleep. Then when he’s ready, he’ll write, but only for a few hours before finally catching up on emails and phone calls.

“Sitting down and writing, while not difficult, is uncomfortable and can be unpleasant, especially when it’s not going well,” said Ryan in an interview with Nir Eyal. “In my opinion, you want to keep it in a brief, flurry of constructive time and then you move on and you go to something else.”

He also reads hundreds of books each year, meets strict book deadlines, and aims to see opportunity within the struggles. Holiday’s habits have come from trying different ways, those other ways not producing the results, and then settling on this system and more or less sticking to it. So, how can you create similar habits to find something that works?

How to Build Habits for Productivity Like Ryan Holiday

1. Make reading a priority and create a commonplace book.

Most successful people read a lot and Holiday is no exception. He doesn’t speed read or have a secret method. He just makes a lot of time for it.

Holiday tells the Simplify Podcast, that he’ll “swarm” around a topic that fascinates him by reading anything and everything he can find on it until he understands its essence. Holiday attempts to know so much about that one single thing that he can tell if an author is right or not.

Holiday feels that “swarming” it’s more efficient, as opposed to reading about a variety of topics and starting from square one each time you return to the original subject. He also doesn’t just read, he actively takes notes and keeps a commonplace book. Holiday chooses to only read physical books, making notes in the margins. He’ll wait a week after finishing and then transfers those notes onto 4×6 index cards.

Organizing these cards into boxes makes up his commonplace book. It can be anything that strikes Holiday – quotes, facts, his own summaries. He labels the cards by topic and can refer back to them when writing a book or an article. “You never know when an interesting anecdote may come in handy for your next book,” Holiday explains. It’s also incredibly helpful for absorbing the knowledge and actually learning something from the books he reads.

2. Focus on only the things you can control.

This idea is rooted in stoicism, the ancient Greek and Roman philosophy that Holiday practices in his daily life. Stoics assert that we don’t control the world around us, we control how we respond to it. Holiday knows the importance of making this distinction and creating a schedule with these ideals in mind.

In that same interview with the Nir Eyal, Holiday says he worked on finding a system that makes it harder for the “resistance” to take hold. That means creating a routine where you have the least possible opportunities for distraction and are being realistic about the fact that you’ll probably get distracted anyway.

To avoid distractions, Holiday uninstalled Facebook on his phone, uses InstaPaper to read articles when the mood strikes (instead of scrolling to find content), and doesn’t have voicemail set up.

“When I’m thinking about my routine, I know that there’s going to be distractions,” said Holiday. “I know that it’s not going to go well sometimes. I know that I’m going to have a million other tempting influences or things to work on. So, you try to create something that’s robust that can resist that but also you’re not spending all your time fighting it.”

As the lessons of stoicism teach, when something doesn’t go well, instead of being upset about it (which does nothing), you can look at it as an opportunity. “As a writer, if I learned a painful lesson, can I make that into an article or am I just going to sit here and be upset about it?”

3. Take ideas from people smarter than you.

Holiday has gotten comfortable saying “I don’t know”. He’s not afraid to borrow ideas from people he admires and it’s probably a reason why he’s been so successful. Basically, you don’t have to do everything on your own.

In a discussion with Tim Ferriss, Holiday started making a simple to-do list. Ryan uses those 4×6 notecards he loves so much and writes 5 to 6 big items to finish. Crossing them off as he goes, it gets ripped up at the end of the day and feels great.

Tucker Max is to blame for his self-proclaimed embarrassing iTunes playlist. Holiday listens to the same song on a loop to “space out and get into the zone”, reporting that it helps his productivity substantially.

4. Make time in the mornings.

Holiday aims to start each day peacefully without jumping into the chaos of his inbox or social media. Most people check their phones as soon as they open their eyes and are instantly in work mode – or distraction mode. Instead, Holiday has learned to be more productive by getting to work only after he’s had a chance to think and taken a moment for himself.

Use this time wisely. Cook a large breakfast and enjoy it with your family. Write in a journal or read while adding to your commonplace book. Get a solid workout in. “Exercise will make you productive,” writes Holiday. “It will clear your mind, process any negative energy, and give you a win every day.”

Add these daily habits to your list:

  1. Choose three physical books about one topic that you’re insatiably interested in and make it a priority to read the entire stack in one weekend. Stick with one subject at a time instead of reading a stack of books about various topics.
  2. Take reading notes – write notes in the books you’ve read and once you’re finished, let it simmer in your mind for a week before returning to them and writing down what you marked on 4×6 notecards. File the notecards by topic in your commonplace book and aim to add 25 notes each week.
  3. Remove social media distractions – control distractions by deleting the Facebook app from your phone, using Instapaper to read articles, and deleting voicemail (or have your voicemail tell callers to send you an email).
  4. Listen to a mentor each day – find a mentor, even if it’s only on the internet, and watch one YouTube video per day about their daily routines. Test out one habit at a time to find what works for you and add a new habit (or adjust a current habit) weekly.
  5. Wake up one hour earlier to start the day peacefully, whether it’s for a workout, cooking a large breakfast, starting your next book, or writing in a journal.
  6. Listen to the same song while working – make a playlist of one song on repeat to use the next time you have a big assignment.

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