The Beauty of Improvisation

Deep Work + Deep Play + Deep Love = A Fulfilling Life

If you were invited to share your life’s work with one million people, would you risk messing up when you could follow the script? 

In the early days of TED, Chris Anderson used to have each speaker write and memorize a complete script to make the best use of the time. Although this strategy produced many world-class TED Talks, it also held back those who thrived in improvisational environments—such as professors explaining complicated topics to their students.

“Today, we don’t have set rules,” Anderson wrote in TED Talks, “We just have suggestions for helping speakers find the mode of delivery that will be most powerful for them.” What’s more important than the rule is that speakers are empowered to speak in their most comfortable, confident, and passionate way.

We sure can prepare too much.  

Melinda Gates reflected in her memoir The Moment of Lift

When I’m overprepared, I don’t listen as well; I go ahead and say whatever I’ve prepared, whether it responds to the moment or not. I miss the opportunity to improvise or respond well to a surprise. I’m not really there. I’m not my authentic self.

The more effort we put, the more attached we are to the outcome. Such focus may throw us off track when the situation is different from our plan (and there will always be surprises). Instead of focusing on controlling every detail, why not direct the energy to the present moment?  

During my final mentorship session for Building A Second Brain, I decided to do something different.

Instead of frantically cleaning up my Roam space two hours before the session, I pulled back the curtain and shared the messy outline of this newsletter. Instead of teaching some well-thought principles, I listened to the questions and wonders of the students. Instead of enforcing my agenda, I created space for the community to reinvent themselves in the breakout rooms. 

When everyone got back to the main room, impromptu conversations flew from one student to another and filled me with gratitude and awe. 

As Gates noted, “I guess what I need to role-model a little more is the ability to be open about the mess. Maybe I should show that to people.”

The more comfortable we are, the easier it is to live out our whole selves. 

The best things in life usually aren’t planned.

Martin Luther King was one of the most prepared speakers in U.S. history. In addition to his innate talent and thorough training, he often spent more than 15 hours preparing every syllable of his Sunday sermon. Dr. King was no stranger to memorizing, and his preparation set him up to improvise for the most critical moment in his life.

On August 28, 1963, Dr. King had twenty minutes to prepare his most important speech. He had no time to write a script. He had to improvise for the first time in his life. 

If you look at the actual footage, you might notice moments when Dr. King rambled. Yet, those early falters didn’t throw him off track. He spoke each word with force and fully absorbed the energy from the crowd. As the speech rose to its climax, Dr. King turned to the audience and looked for something to say.

“Tell them about the dream, Martin!” Mahalia Jackson yelled.  

Jackson was referring to something Dr. King had been preaching in church. At the moment of maximum danger and opportunity, I Have A Dream was improvised.

Dr. King went on to preach a dream of freedom and justice. A dream where little black boys and black girls would join hands with little white boys and white girls as brothers and sisters. 

That rest was history. 

Dr. King not only thrived with improvisation but also created a dream with his deep work in public speaking, deep love for people, and deep play at the present moment.  

You can improvise daily too.

When I first started LivingOS, I streamed my talk shows to thousands of viewers each week. I was very stressed until I stopped focusing on myself. When I began to focus on the whole experience, I picked up subtle details and improvised on the spot. Instead of worrying about what to say, I took a deep breath and focused on connecting with my guests.

When I do interviews, I prepare just enough to ask good questions, but not so much as to be distracted by the detailed agenda. When I give talks, I prepare my favorite stories and trust the host to bring out the best of me. When I write newsletters, I research the bullet points and leave the rest for serendipitous play. 

After a thousand hours of improvisation, I came up with this equation: 

Deep Work + Deep Play + Deep Love = A Fulfilling Life 
  1. Deep Work is being fully present on a single task. When you are entirely absorbed in the flow, you can exercise the muscle without certain expectations. By removing that friction, you get to focus on the most important thing—creating something meaningful in life and enjoying the flow.

  2. Deep Love is loving yourself, including your inner critics, unconditionally. Research shows that the improvising brain shuts down your inner critics and lights up your self-expression. When you replace your critical voice with love, you get to embrace new ideas and create flashes of brilliance. 

  3. Deep Play is awakening your creative self and bringing playfulness to everything you do. Alex Soojung-Kim Pang defined play as voluntary, intrinsically rewarding, mentally and physically engaging, and imaginative. When you bring fun and play to what you do, you get to bring forth your unique gift to the world effortlessly.

You can bring deep work, deep love, and deep play to everything you do. 

Stuck with a tedious task? Put on some lively music. Stressed by a big project? Start with the part you love the most. Tired of your wellness routine? Focus on the benefits it could bring to your loved ones. 

That, my friend, is the recipe for a fulfilling life.

Listen to my conversations with executive coach Leland Franklin and Jamie Kim (Spotify | Anchor).

Read Steph Smith’s awesome playbook on creating high-quality content online.

Support the creative work I’m doing by buying me a coffee.

Enjoy life. I recently reconnected with surfing 🔒 and am heading to Tahoe tomorrow.

To a fulfilling life,


This piece is inspired by the 30 events I did for Model Breakers. I hope this inspires you to improvise more in life.

Special thanks to Chris Liu, Ju-Han Tarn, David Gaynor, Dani Trusca, Christine Cauthen for providing feedback on early drafts.