How to Take Risks (an Experimental Episode) | Marissa Schneiderman

Oct 27, 2023 Episode Page ↗
Overview

Dan Harris and Senior Editor Marissa Schneiderman discuss the importance of risk-taking and experimentation in life and work, drawing on insights from past guests like Adam Grant and Brené Brown. They also share behind-the-scenes details of their new newsletter and meditation app.

At a Glance
19 Insights
45m 12s Duration
15 Topics
6 Concepts

Deep Dive Analysis

Introduction to Risk-Taking and Experimentation

Podcast's Recent Experiments and Newsletter Launch

Adam Grant: Seeking Discomfort and Acceptable Mistakes

Applying Minimum Viable Product to New Ventures

Balancing Ambition with Sanity: The 'Middle Way'

Rick Rubin: Redefining Success and Creative Risks

Unexpected Learnings from Experiments and Live Shows

Examining Motivation: Self-Interest vs. Service

The Power of Intention Setting for Projects

Sarah Cooper: Embracing Mistakes and 'Keep Fucking Up'

Personal Comfort with Failure and Impermanence

Gender, Neurodiversity, and Workplace Risk-Taking

Brené Brown: Vulnerability, Armor, and Innovation Culture

Fostering Open Communication and Direct Feedback

Newsletter Details and Future Content

Minimum Viable Product (MVP)

An approach to launching new projects by releasing a basic version that is 'good enough' rather than perfect. This allows for early feedback and continuous iteration based on user input, reducing initial pressure and enabling quick adaptation.

Sanely Ambitious

A team approach to pursuing goals that balances a desire for growth and new ideas with the need to avoid burnout. It involves brainstorming many ideas, then carefully selecting the best ones and planning their execution in a manageable, sustainable way.

The Middle Way (Effort)

A concept derived from Buddhist teachings, illustrated by tuning a stringed instrument. It suggests finding the optimal balance of effort—not trying too hard to the point of tension, nor too little to the point of laxity—to achieve a desired outcome.

Intention Setting

The practice of consciously defining one's purpose or desired outcome before engaging in an activity or project. It helps align actions with specific goals, such as building a successful business while also aiming to help people, creating a reinforcing positive cycle.

Vulnerability

Defined as the emotion experienced during moments of uncertainty, risk, and emotional exposure. It can involve feeling unsure, taking chances, or showing emotions without knowing how others will perceive them.

Armor (Vulnerability)

Protective mechanisms people develop to cope with vulnerability and uncertainty, often stemming from childhood experiences. Examples include perfectionism, cynicism, control, or exerting power over others, which can hinder innovation and creativity in a culture that punishes failure.

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Why is it important to take risks and experiment in life?

Taking risks and experimenting helps individuals grow, achieve great things, and get comfortable with discomfort. It allows for learning from mistakes and adapting, leading to unexpected positive outcomes beyond traditional metrics.

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How can one balance ambition with avoiding burnout when pursuing new ideas?

It's helpful to adopt a 'sanely ambitious' approach, which involves brainstorming many ideas, then carefully selecting the best ones and planning their execution in a way that doesn't exhaust the team. This aligns with the 'middle way' concept of finding the right amount of effort.

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How should success be measured when taking creative risks?

Success is subjective and not always material; many great works of art were not recognized in their time. It's important to judge experiments holistically, as they may lead to unexpected positive outcomes or learnings that aren't immediately apparent through conventional metrics.

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How can one overcome the fear of making mistakes?

It's important to recognize that mistakes are part of the process and that there will always be another chance to try again. Meditation can help by fostering a sense of humor and willingness to make mistakes, understanding that even through errors, one can walk an 'unerring path.'

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What is the role of vulnerability in personal and professional growth?

Vulnerability, defined as experiencing uncertainty, risk, and emotional exposure, is crucial for innovation and creativity. Cultures that punish failure prevent people from innovating, as innovation inherently involves iteration, failure, and learning.

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How can leaders foster a culture where risk-taking and failure are acceptable?

Leaders should actively encourage risk-taking and iteration, understanding that innovation requires allowing people to fail. They should also model vulnerability and open communication, ensuring team members feel safe to provide direct feedback and share ideas without fear of negative judgment.

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How can one improve interpersonal communication, especially when giving feedback?

Direct communication, even if uncomfortable, is ultimately kind and beneficial for everyone involved. It's important to be respectful and timely, following principles like 'say that which is true and useful and at the right time,' and to set positive intentions before conversations.

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What is the purpose of intention setting?

Intention setting helps align one's actions with a clear purpose, such as building a successful business while simultaneously aiming to help people. This dual intention can create a positive, reinforcing cycle where being helpful contributes to success and vice-versa.

1. Seek Discomfort & Take Risks

Actively put yourself in situations where you might fail, be judged negatively, or embarrass yourself to foster significant personal growth.

2. Embrace Impermanence of Discomfort

When experiencing discomfort or fear, remember the principle of impermanence, knowing that the uncomfortable feeling will eventually change.

3. Evaluate Holistically, Not Just Metrics

Judge risks and experiments holistically, rather than solely by traditional metrics, as they often lead to unexpected positive outcomes or valuable learnings.

4. Practice Sanely Ambitious Brainstorming

Generate many ideas, then allow them to settle before selectively executing the best ones in a way that avoids burnout for yourself and your team.

5. Set Clear Intentions Daily

Practice intention setting regularly (e.g., morning, before exercise, before sleep, before meditation, before projects) to align your actions with desired outcomes.

6. Communicate with Truth, Usefulness, Timing

When communicating, especially when giving feedback, ensure your words are true, useful, and delivered at the appropriate time.

7. Cultivate Self-Awareness of Motivation

Diligently investigate your motivations for actions, acknowledging natural self-interest while also being open to a desire to help others.

8. Allow for Failure in Innovation

Create a culture that explicitly allows for failure, as it is a necessary component of innovation, creativity, and iteration.

9. Start with Minimum Viable Product

When trying something new, don’t put pressure on yourself to perfect it immediately; instead, aim for a minimum viable product (MVP) and iterate based on feedback.

10. Maintain Momentum, Don’t Stop

Even when uncertain about the outcome, continue working and putting things out there rather than stopping entirely.

11. Differentiate Acceptable vs. Unacceptable Mistakes

Learn to tell the difference between acceptable and unacceptable mistakes, balancing the pursuit of excellence with knowing when ‘good enough’ is sufficient.

12. Don’t Dwell on Past Mistakes

Instead of punishing yourself by thinking about every past mistake, accept them as they happened and get excited about what you’ll try next.

13. Focus on the Present Moment

Avoid ‘cheating on the present’ by dwelling on past mistakes or anxieties about the future; stay focused on what is happening now.

14. Prioritize True Self Over External Input

In creative endeavors, prioritize being true to yourself and your passion over listening excessively to well-meaning external input, especially after achieving success.

15. Identify Your Emotional Armor

Become aware of the forms of ‘armor’ you use (e.g., perfectionism, cynicism, control) to manage uncertainty, risk, and emotional exposure.

16. Practice Meditation Regularly

Engage in regular meditation practice to develop a sense of humor about your mind’s distractions and a greater willingness to make mistakes.

17. Foster a Culture of Mistake Acceptance

As a leader, explicitly message that it’s okay for your team to make mistakes and demonstrate moving on quickly from them to create a safe and productive environment.

18. Sign Up for Newsletter

Sign up for the 10% Happier weekly newsletter to receive life hacks, cultural recommendations, podcast news, and upcoming events.

19. Download Meditation App

Download the new 10% with Dan Harris meditation app to access guided meditations, weekly live Zoom community sessions, and ad-free podcast episodes.

I think that seeking discomfort, though, is about much more than just confronting unpleasant or unwanted thoughts. It's also putting yourself in situations where you are likely to fail, where you might be judged negatively, where you might even embarrass yourself.

Adam Grant

Success isn't necessarily material success. Many of the great works of art that we look at now as great works of art were in their day not considered that.

Rick Rubin

Nobody knows. That's the thing. Nobody knows.

Rick Rubin

If you're out there thinking about every mistake you've ever made, don't. You did it exactly the way you were supposed to. Get excited about what you'll try next time, because there will be a next time?

Sarah Cooper

I once described my career as a triumph of narcissism over fear.

Dan Harris

Erring and erring, I walk the unerring path.

Zen expression (quoted by Dan Harris)

You can't expect people to innovate and create if you don't allow people to fail. Because by definition, innovation is iteration, failure, and iteration.

Brené Brown

Clearness is kindness.

Brené Brown (quoted by Marissa Schneiderman)

Say that which is true and useful and at the right time.

The Buddha (quoted by Dan Harris)

Daily Intention Setting

Dan Harris
  1. Set an intention upon waking in the morning.
  2. Set an intention before exercising.
  3. Set an intention before going to sleep.
  4. Set an intention before meditating.
  5. Set an intention for various projects, aiming for a twofold purpose: building a successful business and helping people.

Giving Effective Feedback (Buddha's Rules)

Dan Harris (attributing to the Buddha)
  1. Ensure what is said is true.
  2. Ensure what is said is useful.
  3. Deliver the feedback at the right time.
five or ten years
Delay in launching newsletter Dan Harris's self-assessment of being late to the newsletter trend.
three months
Duration of Marissa's silent meditation retreat A significant personal risk taken by Marissa.
10 years ago
Time since Marissa worked in Silicon Valley Context for Marissa's past professional experience.
32
Marissa's employee number at a startup Her early role at a company now valued in billions.
in college
Age of ADHD diagnosis for Marissa Marissa was diagnosed with ADHD later in life.
every day
Frequency of detention for Marissa in first grade Due to talking too much, reflecting early experiences with being different.
nearly 10 years ago
Time since Dan Harris wrote '10% Happier' Reference to the book's publication and his public panic attack.
2018
Year of Dan Harris's 360 review The review provided feedback on his communication and directness.