How to Cure Anxiety With Play

I think it was the book that Charlie HAD to write, perhaps literally to save his own life.  — Ryan Holiday

The key to curing to anxiety is to play it away.

I don’t experience anxiety the way Charlie did before he wrote Play It Away: A Workaholic’s Cure for Anxiety, but I knew I needed to read this book.

And not because I consider Charlie a friend. (We interned together for Seth Godin in 2008 and have stayed in touch since).

Since taking the entrepreneurial path I definitely feel much more anxious. Not to mention the level of uncertainty and discomfort I consistently face and what that does to my once unshakable confidence.

[Side note: It’s also been an incredible growing experience in which I’ve learned more than I ever could at a 9 to 5 — both about business and myself. As with anything, there are good days and bad and anybody that says otherwise is full of shit.]

Beyond that, I’m a full fledged workaholic and I know Charlie knows what that feels like because often he was the only green dot on gmail when I was still plugging away at 2am on a random week night.

These days I make sure I get my 7-8 hours of sleep, but I hoped his book would have remedies for the other emotions I’ve been feeling of late.

Play It Away did not disappoint. Charlie did a fantastic job avoiding the “I’m a privileged Millennial with 1st world problems” diatribe.  His willingness to be honest and showcase his vulnerability during his rediscovery of play was refreshing and relatable. I enjoyed the book immensely.

In fact, I already feel better and I hope to revisit his book, and this post, on those days where I feel like I’m just grinding away.

Below are some of my favorite takeaways from Charlie’s book.

On Experiencing Anxiety:

Every moment was exhausting. I eyed everyone like they were judging me, pitying me, or trying to manipulate me. My attention was constantly divided. One half of me pretended to be normal while the other half tried to keep it together.

I felt fragile, weak, and hollow.

I was ashamed, because I couldn’t explain it without feeling like a failure. How could I possibly be so miserable and unhappy? What right did I have to feel this way? Couldn’t I just tough it out?

The Primary Source of Anxiety:

The primary source of my anxiety was me. I was the creator of my own suffering. I just couldn’t see it.

[Editor’s note: Love that he takes responsibility for his anxiety rather than pointing fingers.]

On Workaholism:

Because my entire life revolved around work, life stopped being fun. Each week, I felt increasingly sick, exhausted, and apathetic.

On Why We Work So Much:

Status. Money. Guilt.

How to Know if You’re Experiencing Anxiety? Ask Yourself:

  • Do I feel guilty or anxious when I’m not working?
  • Have I stopped playing with my friends?
  • Do all of my daily activities revolve around building a more successful career?
  • Am I sleeping fewer than eight hours per night?
  • Am I consuming stimulants multiple times per day to hide my exhaustion?
  • Am I sitting still and staring at screens for most of my waking hours?
  • Do I interact with people primarily through screens?
  • Am I indoors all day long, depriving myself of fresh air and sunlight?
  • Do I depend on alcohol or drugs to cope with social situations outside of work?


On the ‘Life is Serious’ Mentality:

Somehow, I managed to suck the joy out of every single aspect of my existence. I was so intensely critical of life that I blocked my ability to enjoy it.

I was convinced that the real world was a miserable grind for adults, and that I needed to work even harder if I wanted to enjoy life. Someday, I’d be rich and permanently successful. And when I reached that point, I would allow myself to stop worrying and be happy.

The Solution to Workaholism Induced Anxiety:

I really don’t function well when I approach life as Work. I have to think of life as Play.

When I tackle my work with a sense of play — voluntarily, because I’m inherently attracted to it — my creativity and optimism soar. I fall in love with the process.

On Vampires (Someone who Drains Your Energy When You Interact With Them):

You can never relax or be yourself around a vampire, because you’re too busy trying to avoid their emotional assault.

On (Trying to) Live Up to Other People’s Expectations:

I felt spoiled and embarrassed whenever I had to explain why I’d left (two cool gigs) – I had no desire to do the work. I wasn’t interested in what I was doing anymore, and no amount of money or prestige could excite me enough to work on things I didn’t want to work on.

And yet, I still felt obligated to live up to people’s expectations.

This pressure I felt to make it was such a burden, until I realized that I would never be content. I’d be working harder and harder just so I could keep regaining everyone’s approval. No level of success would ever be enough because I would always be chasing the world outside of me. What was the point of working so hard if I wasn’t doing it for myself?

On What Work *Should* Feel Like:

Work shouldn’t feel like indentured servitude; it should feel like a game you would willingly play because it’s rewarding and it energizes you.

On Healing Your Mind:

Playing on a regular basis is an investment in your health and happiness. (Click to tweet).  Not only does it allow you to have fun with your friends while exercising, it also turns your thoughts off for a while so your brain can recharge.

On The Effect of Play on Your Work:

Play, it seemed, had the power to make our work easier, faster, and more enjoyable.

On Getting Enough Sleep and Pruning Your Digital Information Diet:

To me, sleep was a necessary evil that cut into my productivity. The endless stream of digital information I was taking in every waking hour only compounded the problem. My mind never had enough time to shut down, relax, and digest everything that poured in during the day. No wonder my mental health was shot.

On the Importance of Observing Your Thoughts:

My thoughts only had power when I granted them that authority.

On How to Deal with Stressful Thoughts:

How long would it take for your panic and shame to turn into apathy and annoyance? That’s how you should think about your stressful thoughts — as a room full of obnoxious people trying to wind you up. You can either let them harass you every single day, or you can practice not responding to them.

On Venting to Yourself and Practicing Gratitude Through Writing:

It’s impossible to heal your anxiety if you’re constantly scolding yourself for not feeling normal. You need to be loving and supportive. The best way to do that is by quietly venting to yourself and practicing gratitude through writing.

Write down every single thing you’re currently worrying about. Don’t filter your words or resist your feelings. Be brutally honest about what you are going through. Expose your fears and insecurities so you can see them outside of yourself.

Then write down at least one reason why you’re grateful for every single thing you’re worried about. It doesn’t matter how awful or irredeemable that source of stress has been; come up with one reason why you’re thankful to have experienced it.

On Being Male:

We usually don’t discuss feelings because it’s always been off-limits, so it makes us really uncomfortable. Almost every man has been raised to value how he thinks more than how he feels, and because a lot of our feelings aren’t easy to rationalize, we block ourselves from expressing them.

On the Importance of Releasing Frustration:

You can’t be happy and awesome and stoic all of the time. Screw perfection, screw poise – just let go. (Click to tweet).

On Enhancing Your Environment:

The first step is to pay attention to how you feel in the rooms you spend the most time in – your bedroom, your living room, your kitchen, and your office. Eliminate any possessions in those rooms that make you feel annoyed or overwhelmed or tired.

On Work as a Game:

Instead of killing myself for future success, I work to feel alive right now.

In Conclusion:

You don’t need to be on vacation in order to play. You don’t even need to stop working. You can always do it. Play is a state of mind — it’s a way to approach the world. Whether your world is a frightening prison or a loving playground is entirely up to you.


I’ve shared a lot in this post and I hope Charlie doesn’t mind. If you experience anxiety, are a workaholic, or just want to improve your quality of life, I still recommend you pick up a copy of the book for yourself.

Different parts will resonate and you’ll latch on to different techniques in order to cure your own anxiety. For example, I breezed through the “heal your body”section because I’ve previously implemented a lot of that chapter’s advice into my life, but spent quite a bit of time thinking through Charlie’s advice for healing my mind.

You might also like Preventing Burnout: A Cautionary Tale in which Charlie discusses his journey, including what it was like to work with Tim Ferriss for 3 years.

And here’s my other book reviews.

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Photo Credit: abhiomkar via Compfight cc