Jack Dorsey on How to Build a Future: Principles For Creators, Artists, and Entrepreneurs.

Jack Dorsey is one of the most successful and famous entrepreneurs in the world. He is the co-founder of Twitter and CEO of Square. Jack is known for his passion for exploring eastern philosophies and bringing community-oriented business solutions.

During his speech for “Startups School 2013”, he shared one of his brilliant thoughts, advice, and rules that I think are worth sharing.

During the entire speech, instead of giving advice strictly related to business, Jack focused on explaining the philosophy behind building new things. Based on his favorite books and personal tips he developed an interesting system that seems to be suited for all kinds of people who want to build and create new qualities in the world.

Five Lessons from “The Art Spirit” by Robert Henri

This book is about creativity through the lens of art teacher and painter Robert Henri. He covered the essential beliefs and theories that embodied his entire system of teaching. There are technical aspects as well as inspirations that touch the human soul.

This book is for everyone who wants to create and express themselves through all kinds of art, and for those who find wisdom and happiness in the process of creating.

There are the quotes that Jack Dorsey’s found the most helpful and valuable for the creators and people who struggle with their craft. I added on top of them some comments to better visualize the problems he touched.

Craft is essential.

“Art when really understood is a province of every human being. It is simply a question of doing things [...] When the artist is alive in any person whatever his kind of work may be he becomes an inventive, searching, daring, self-expressing creature.”

Jack changed the perspective on understanding what matters in terms of building. He stated that true innovators and makers shouldn’t be focused only on the end-product, but they should pay more attention to the craft itself. To this moment full of creating, failed attempts, and hopes. This is the moment where all the magic happens. Instead of just thinking about achieving, he focused on inventing through the work.

The cost of success is high and inevitable. But the reward is lucrative and long-lasting.

"The work of the art student is no light matter, few have the courage and stamina to see it through. You have to make up your mind to be alone in many ways. We like sympathy as humans and we like to be in a company. It is easier than going it alone but alone one gets acquainted with himself grows up and on, not stopping with the crowd.”

If you succeed, it means that someone has paid for it because your success is not necessarily positive for everyone. Jack emphasized the painful aspects of creating something meaningful. You will pay for your success, but if you have achieved it, you can enjoy it for the rest of your life. The stakes are high, as are the costs.

Lonely and sleepless nights of creation are an indispensable path of any creator who intends to build something bigger than himself.

Don’t copy. Innovate through your own vision.

“We are not here to do what already had been done. Know what old masters did, know how they compose the pictures but do not fall into the conventions they established.”

It’s so easy to fall in the footsteps of others, especially in some sort of developed fields, such as technology, especially in Silicon Valley. But the truth is you can’t copy someone’s way to success, you have to find your own way.

It’s good to use productively the legacy of others, such as the form of inspiration, but it’s shouldn’t be the actual plan, rather some kind of afflatus. You have to be a master of your own tools.

Rejections are an inseparable part of the journey. Don’t fall into the trap of acceptance.

“Don’t worry about rejections. Everybody that’s good has gone through it. Don’t let it matter if your works are not accepted at once. The better or more personal you are less likely they are of acceptance. Just remember that the object of painting pictures is not simply to get them in the exhibition. It is all very fine to have your pictures hung but you are painting for yourself, not for the jury.”

In my opinion, it’s one of the most meaningful quotes from the book. We as human beings have this unhealthy tendency to work so hard just to get acceptance in the world. Often the only way for us to check if we are doing something right is acceptance and some sort of positive feedback. But the truth is somehow hidden, it’s often invisible for others, we have to seek it out.

Be pioneer.

“The art student of these days is a pioneer. Must pioneer beyond the mere matters of fact. I believe the great artists of the future will use fewer words, copy fewer things. Essays will be shorter in words, and longer in meaning.”

The most important thing that all of the creators have in common is the passion for building for themselves. They build what they want to see in the world, and this is why they often win as big as it’s possible. Because they created something that never exist before - people will pay a lot for the new quality.

Lessons and rules from “The Score Takes Cares of Itself” by Bill Walsh

Bill Walsh is a towering figure in the history of the NFL. His advanced leadership transformed the San Francisco 49ers from the worst franchise in sports to a legendary dynasty.

Bill Walsch showed how being process- and detail-oriented brings about significant changes. He was entirely focused on improving the standard of performance, starting from scratch and figuring out every detail of the process that leads to the bigger picture. Instead of focusing on winning the Super Bowl, he said we should clean the locker or tuck in a shirt. Each step led to remarkable achievements.

This book is worth reading if you thinking about all kinds of leadership, whether is running the company or leading a team within a charity organization.

It all starts with the vision and purpose of the mission.

“Running a football franchise is not unlike any other business. You start first with a structural format and basic philosophy and then find people who can implement it”

The fundamental rule about creating all kinds of things is to start simply with an idea, purpose, and mission. Great things start with a small sparkle of vision that is the fundament on top you lay the rest. You start building structures and finding people who understand your vision, can contribute and implement it.

Six rules of establishing the standard of performance

“You start with a comprehensive recognition of reverence for an identification of the specific actions and attitudes relevant to your team performance and production.”

The first step to establishing a high standard of performance is to make everyone on the team feel like this is a place where they have a vote and where they belong. Recognize and appreciate each member separately and the members as a whole team.

“You’d be clear and communicating your expectation of high effort and execution of your standard performance.”

The second step is being clear with your intentions that others can align with is the key to efficient communication that leads to successful leadership within the organization.

“Let all know that you expect them to possess the highest level of expertise in their area and responsibility”

Third step: by relying on the knowledge and responsibility of others, you show that you first take them very seriously and second you value their participation very much. This contributes to the fact that everyone feels like a part of the team, which is why each of the members does their best to improve the whole team.

“Beyond standard and methodology, you teach your beliefs, your values, and your philosophy”

Four rule is that you want to have a team of people who feels connected to the organization, not the set of independent contractors who are indifferent.

“Teach connection and extension”

Five rule: It's better to be around people who know for what and why they're doing certain tasks.

“Make the expectations and metrics of competence the demand in action and attitudes from personal the new reality of your organization”

What’s important about building a team is that you need to set expectations around how people need to perform in the company. And it can be simple things, but without them, you will be reactive to the outside factors, and when it happens, you stop focusing on your vision. Then you collect and work on someone else's roadmap.

Bill Walsh also wrote about being a successful leader, here’s the list of his rules.

12 Habits of being a successful leader:

  1. Be yourself

  2. Be committed to excellence.

  3. Be positive (just probably the hardest thing)

  4. Be prepared. Good luck is the product of good planning.

  5. Be detail-oriented

  6. Be organized

  7. Be accountable

  8. Be near-sighted and far-sighted

  9. Be fair

  10. Be firm

  11. Be flexible

  12. Believe in yourself

There’s also rule number 13., which is to be a leader. And the most crucial insight is that a leader is a person who is focused entirely on getting up and showing, not telling.

This is also one of the hardest transitions that humans can make. Going from individual creation to person who can lead a team and bring up the sense of mission and purpose is a process full of ups and downs. But this is your process, not someone else.

This book is a story about an amazing turnaround from hard to managing ego-driven football players to a cooperative team winning four Super Bowls in a row just by bringing a sense of mission and focusing on these details.

“Daily Note” - Fundamental Tool of Exponential Growth

Bill Walsh inspired Jack Dorsey to create his own list.

He started doing daily notes and they turned out to be the most fundamental in his growth and establishment of the practices. The keyword is daily. His rule is about cultivating a habit and being consistent.

You have to view your notes on a daily basis. He wakes up to his iPhone notes, checks them throughout the day and before sleep.

“One of the fundamental things that I learned from it, is how to give you focus. How gives you something that allows you to really ignore everything else that’s going on all the other noise, allow you to focus on what’s most important”

Jack splits his daily notes into two parts - do's and don'ts. And it was this that contributed to his enormous growth and fostered the sense of a mission that he's cultivates daily.

Jack’s do-list:

1. Stay present

It’s easy to get trapped in the past or in a constant state of thinking about the future. Simply by reading this list he brings himself into the present.

2. Be vulnerable

Show people your mistakes, weak points, and fears because people can relate to them. They going through similar things. The best way to build a sense of communication and belonging is by connecting through authenticity.

3. Drink only lemon water and red wine

4. Six steps of twenty squats and push-ups throughout the day

5. Six steps of 30-second planks

6. Run for three miles

According to Jack, taking care of your physical health is a fundamental aspect in terms of productivity, mental clarity, and overall growth. You don’t have to follow or copy these rules, but it's worth paying attention to your physical health and considering how you can improve it. The effects can be holistic and beyond your expectations. Jack is also a fasting enthusiast, he eats only one meal a day (This is not advice).

7. Meditate

Jack Dorsey shared in one of his tweets that he specifically practiced Vipassana meditation, an ancient Buddhist meditation technique that frequently involves 10 days of silence. According to Jack Dorsey:

“Vipassana is a technique and practice to “know thyself.” Understanding the inner nature as a way to understand…everything. It was rediscovered by Gautama the Buddha 2,500 years ago through rigorous scientific self-experimentation to answer the question: how do I stop suffering?” [source: tweet]

8. Stand up straight

9. Say hello to everyone

10. Daily video journal

11. Seven hours of sleep

Jack’s to-do list is mostly about maintaining the physical health in order and keeping the mental clarity through an aspect that touches gratitude, meditation, sleep, and being present, which brings to mind his fascination with Eastern Philosophy.

Jack’s don’t-list:

1. Don’t avoid eye contact

2. Don’t be late

3. Don’t set up expectations for someone and not meet them

4. Don’t eat sugar

5. Don’t drink hard liquor or beers on the weekdays

Jack Dorsey didn't share all the rules on the don't list, as many of them touch his personal life. But what is in common with the previous one is that these principles are about maintaining physical health in good shape and its relationship with people and himself.

The CEO of Square established the fundamental steady-going pattern suited for him to achieve extraordinary things and it works pretty well for him, which doesn’t necessarily mean it will be your case.

Find your own pattern, that will suit you, but take into consideration a system that is oriented on daily execution. It's about a list that you could check throughout the day.

“Angoisse” by Serge Gainsbourg - strike a chords

The culmination of his presentation was sharing a fragment of his favorite song with the audience. This song was “Angoisse” by Serge Gainsbourg. According to Jack, this is a type of piece of art that is worth striving for.

This song revealed the essence of art. It captures how creation can be simple and complex at the same time. This song has a universal value because it resonates with everyone, and this is the endpoint of the presentation, it answers the question of what building a future is all about.

It's about a creation that you want to see in the world that strikes a chord with as many people as possible.

“What this song reminds me of is just how simple creation can be but also how complex it can be. How strong you have to be to get this deep, to get something this essential. To get to something that actually strikes a chord with so many people and potentially strike a chord with everyone on the planet. That’s why we’re all here in this room. We want to build something we want to create something that resonates with every single person on the planet.”

Summary:

I always wrote a few points that I considered crucial as the summary of a blog post. This time I leave Jack's quote, which in my opinion perfectly covers the essence of creating the future. Be pioneer.

“You are building what you want to see in the world. You are making a bet with the world that resonates with other people. Sometimes you’re going to win the bet. Sometimes you’re going to lose the bet. You put that loss on the shelf and you bring it back another day, but it’s up to you to make that interpretation to make that creation and to paint what you want to see in the world.”

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