How To Take Your ‘Deep Work’ Even Deeper

This curated column is authored by leadership & startup consultant Benjamin Hardy

deep work

In Deep Work: Rules for Focused Success in a Distracted World, Cal Newport argues — like Tyler Cowen in Average Is Over — that our information economy is creating a growing divide between the successful few and mediocre many.

Deep work is:

  • Rare
  • High value
  • And non-replicable (i.e., not easy to copy/outsource)

Shallow work is:

  • Common
  • Low value
  • Replicable (i.e., anyone can do it)

The Beauty Of Abundance

The success of others is simultaneously your success. The more you create, the more you challenge me to create. Success breeds success — synergy. When I read a book or article that blows me away, I get pumped! I love that someone went there.

When Shaun White was training for the 2014 Sochi Olympics, he decided to opt-out of the European X-Games. While watching the competition from home, White witnessed one of his competitors’ stomp a trick in the half-pipe no one had ever seen before — the YOLO flip.

Rather than getting upset by the innovative audacity of his competitors’, White was electrified! He was so inspired he learned the trick himself and even a different variation of the trick never before done.

It’s incredible watching others push boundaries never before pushed. It’s especially fun when you’re inspired — rather than put-off or intimidated — by it.

Are you put-off or inspired?

This article is intended to push your creative boundaries and to assist you in doing your greatest work.

1. Try Stuff That’s Never Been Done Before, Then Generously Share It With Others

How can you be more creative in your work?

What are other people in your space currently not doing?

How can you shatter the status-quo?

Where’s your YOLO flip?

What are some dogmatic rules you’ve been following that are actually crippling your performance?

How can you more authentically establish your identity in your work, as opposed to imitating the work of others?

How could you rewrite the rules to the game?

I have a friend, Nate, who is doing some really innovative stuff at the real estate investing company he works for. He’s using strategies no one else is using. And he’s killing it. He told me he considered keeping his strategies a secret. After all, if other people knew about them, that’d mean less leads for him.

But then he did the opposite. He told everyone in his company about what he was doing. He has even been giving tons of his leads away! This has never been seen before in his company.

But Nate knows that once this strategy dries up, he can come up with another one. Nate makes pies — for himself and several other people. And yes, he is also the top-selling and highest-earning in his company. It’s because he constantly pushes new boundaries, then shares his ideas, resources, or information.

Inspire other people with your own YOLO flips, then keep making more.

2. Have More Fun In Your Work

Although most people stop playing when they become adults, it is one of the best strategies for going deeper in your work. In his TED talk, Stuart Brown said, “Play leads to brain plasticity, adaptability, and creativity… Nothing fires up the brain like play.” As Greg McKeown explains, “Very successful people see play as essential for creativity.”

There is a burgeoning body of literature highlighting the extensive cognitiveand social benefits of play, including:


  • Enhanced memory and focus
  • Improved language learning skills
  • Creative problem solving
  • Improved mathematics skills
  • Increased ability to self-regulate, an essential component of motivation and goal achievement


  • Cooperation
  • Team work
  • Conflict resolution
  • Leadership skill development
  • Control of impulses and aggressive behavior

My approach to writing is to have as much fun as possible. That’s what guides my writing process and my writing progress. For me, it’s like snowboarding — if I’m too serious about it, I’ve missed the point. So I’m just trying new tricks on my snowboard and pushing my creative boundaries because it’s fun. When it stops being fun, I take a step back and question my motivations.

3. Produce An Absurd Volume Of Work

In the book Originals: How Non-Conformists Move the World, Adam Grant explains that “originals” (i.e., people who create innovative work) are not reliable. In other words, not everything they produce is extraordinary. And the same is true for you. In order to produce your magnum opus, you’ll need to create a high volume of work. You have to kiss a lot of frogs to find your prince.

For example, among the 50 greatest pieces of music ever created, six belong to Mozart, five are Beethoven’s, and three Bach’s. But in order to create those, Mozart wrote over 600 songs, Beethoven 650, and Bach over 1,000.

Similarly, Picasso created thousands of pieces of art, and few are considered to be his “great works.” Edison had 1,900 patents, and only a handful we would recognize. Albert Einstein published 248 scientific articles, only a few of which are what got him on the map for his theory of relativity.

Quantity is the most likely path to quality. The more you produce, the more ideas you will have — some of which will be innovative and original. And you never know which ones will click. You just keep creating.

4. Remove Yourself Completely From Your Work Regularly

If deep work requires removing yourself from distraction, than going deeper requires removing yourself from your work.

Every year, Bill Gates takes two weeks off for his “think weeks.” Complete seclusion. Intense learning and thinking. Explosive creative breakthroughs.

Similarly, every seven years, designer Stefan Sagmeister closes his New York studio for a yearlong sabbatical to rejuvenate and refresh his creative outlook. In his TED talk, Sagmeister explains the creative breakthroughs he gets during his sabbaticals. Actually, it’s during the one year away from work that he comes up with his best ideas to pursue during the next few years of work.

In Deep Work, Newport explains that various companies are having their employees take an entire workday off, to completely unplug. What they’ve found is that this one day off increases productivity and job satisfaction.

I’ve recently implemented a one day/week “sabbatical.” On Thursdays, I wake up at 5:30 A.M. and drive two hours to Columbia, South Carolina. I have this spot I love there which is perfect for quiet reflection and meditation. The purpose is to refresh, reset, and to get inspired. Many people go out into nature for a similar purpose.

Doing this one day/week break from life has helped me feel more connected to myself, and happy with life. As a consequence, I’ve become more productive in work.

I challenge you to schedule in regular sabbaticals — in whatever form works best for you. Don’t do what’s convenient (you’ll always find an excuse to keep working). Instead, do what works best for you. Do you need weekly get-aways, bi-weekly, monthly, or quarterly?

5. When You Get Insight, Don’t Rush Off. Is There More?

The deepest connections come after the initial breakthroughs. Unfortunately, most people leave their deep mental-space the moment they get an insight. For most of us, this reflects our addiction to shallow.

When you start to get creative breakthroughs (i.e., deep work), don’t rush away from that thought premature. Instead, ask yourself, “Is there more to this idea?”

Keep your notepad near. Frequently, you will find there is much further and deeper connections than your initial conception. Actually, the breakthrough after the breakthrough is where the real gold is. You have to mine deep for the richest rewards.

After you make further connections, don’t rush off. Stay with it. Ask yourself again, “What have I missed? Is there still more?”

Make this a pattern in your deep work and you’ll be shocked and humbled by what you learn.

6. Re-frame Your Anxiety Into Excitement

Doing creative work can be “risky” according to Seth Godin. Deep work is not your safe logistical busy-work. It involves vulnerability and a chance of failure — often causing anxiety and fear.

When you’re anxious about what you want to do, the initial coping strategy is to calm yourself down. However, according to research done by Alison Wood Brooks, PhD, of Harvard Business School, “Anxiety is incredibly pervasive. People have a very strong intuition that trying to calm down is the best way to cope with their anxiety, but that can be very difficult and ineffective.”

Trying to calm yourself down will actually reduce your performance. Conversely, re-framing your anxiety as excitement can dramatically improve your performance.

You’re not scared. You’re excited.This is exactly what you want to be doing!

7. Re-frame Stress As Assistance, Not Resistance

In her famous TED talk, Kelly McGonigal, Stanford psychology professor and author of the NYT Best-selling books, The Upside of Stress and The Willpower Instinct, explains that how you feel about stress chemically alters your physical-stress-response.

If you perceive stress as a bad thing, then when you experience stress your heart-rate increases and your blood vessels constrict. This is bad for performance and can also lead to cardiovascular disease.

Conversely, if you perceive stress symptoms as a good thing — your own body preparing you to meet a particular challenge — your blood vessels stay relaxed even while your heart is pounding, which cardiovascular profile is extremely similar to feelings of joy, excitement, and courage.

8. Internalize The Worst Case Scenario

Psychological research by Julie Norem has found, that in some cases, it’s better to be a pessimist than an optimist. When you know the course of action you want to take, you’re better off imagining all the bad things that could happen if you fail.

According to Norem, “Defensive pessimism is a strategy used in specific situations to manage anxiety, fear, and worry.” Instead of being paralyzed by fear, defensive pessimists consciously envision the worst case scenario to escalate their anxiety and convert it into motivation.

As Adam Grant explains in Originals, “Once [defensive pessimists] considered the worst, they’re driven to avoid it, considering every relevant detail to make sure they don’t crash and burn, which enables them to feel a sense of control. Their anxiety reaches its zenith before the event, so that when it arrives, they’re ready to succeed. “

Tim Ferriss uses a similar approach when considering new endeavors or important decisions — what he calls, “practical pessimism.” Involved is Ferriss visualizing all the negative things that could happen if he proceeds. Instead of defining his goals, he defines his fears — “in excruciating details, the worst case scenarios.” For Ferriss, most of the perceived worst case scenarios aren’t all the bad or rarely occur. Even at most grim, getting back to status-quo is seldom difficult.

However, in the case of Lewis Pugh, the worst case scenario was death. In 2007, Pugh wanted to become the first person ever to survive a long-distance swim across the North Pole.

Two days before his attempt, Pugh took a dip for a five-minute practice swim, and lost all feeling in his entire left hand and the fingers of his right. The cells in his fingers erupted, and he was hyperventilating. He wouldn’t regain feeling in his hands for four months.

Instead of visualizing victory, Pugh imagined failure. “Great depths don’t normally hold any fear for me, but this is different,” he thought. If Pugh failed, he would die, and his body would sink over two miles to the bottom of the Arctic.

Focusing on the worst case scenario challenged Pugh to prepare more conscientiously, preparing him to mitigate against all possible risks. “Fear forces you to prepare more rigorously and see potential problems more quickly,” he recounted. Ultimately, he was successful in his quest.

Both Ferriss and Pugh use negative internalization to prepare themselves for optimal decision making and high performance. Not only does it help you prepare for the worst, but allows you to convert any anxiety into fruitful motivation.

9. Bounce Your Work Off Smart People With Different Angles

Michael Simmons, columnist at Forbes and co-founder of Empact, and I have recently started having “idea-hashing” conversations. We’ll switch-off, one week focusing on the ideas he’s thinking and writing about, and the next week focusing on the ideas I’m thinking and writing about.

Vocalizing your thoughts to someone else challenges you to make them less nebulous and more concrete. It’s also good to ask someone from a different field and with different life experiences to shed light on your ideas.

Similarly but different, it’s good to bounce your ideas off people who radically oppose your ideas. When you’re put on the defensive, it challenges you to rethink your ideas from different angles, allowing you to go deeper.

Don’t keep your deep work purely alone. Take your solo thought-children to other people and get different angles on them. This will allow you to get out of your tunnel vision.

10. Leverage Your Willpower

In a recent article about how he performs deep work, Ryan Holiday recommended exercising in the afternoon as opposed to the morning or evening. For Holiday, running in the afternoon allows him to work through his thoughts from different angles as well as come up with new ideas, so that when he gets back to his desk he has “fresh stuff” to work with.

From a psychological perspective, Holiday’s approach makes absolute sense. According to research, your willpower is strongest in the morning, after a night of regeneration. Consequently, the morning is the best time to do deep work, which Holiday also recommended.

Knowing the literature on motivation and self-regulation — which are foundational to willpower — many of my professors also exercise mid-afternoon. They use their mornings for hard mental work, then take a mental break to exercise around lunch. After their work-out, they feel mentally charged for a few more hours of afternoon work before the end of the day.


Deep work is blissful and highly rewarding. The better you get at deep work, the higher your income and greater your impact will be.

Connect Deeper

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