Cup 1 | Buster Benson

Date: Tuesday, October 29

Location: Cafe Cumaica, San Francisco, CA

I found Buster in 2011 when I came across a site he built, 750words.com.

The site, inspired by an exercise in The Artist’s Way, unsurprisingly, encourages people to write 750 words everyday. It’s not blogging. It’s a private place to store unfiltered, spontaneous, thoughts online. The intention is to create a habit of writing three pages (approximately 750 words) daily to clear your mind and get the ideas flowing for the rest of the day.

As Buster says on the site, you can’t get to 750 words “without running into your subconscious a little bit… 750 words takes a bit of effort, and it never fails to get me typing things that I have wanted to articulate without realizing it. And that’s the point”. It’s an exercise that helps you figure out what you’re subconsciously thinking.

The first time I tried it, I was 180 words into my first post I realized, this is hard. I’d run through the typical things, yesterday I did a, b and c. Today I’m doing to x, y, and z. I couldn’t think of anything else to say. 

Writing more required going deeper into my psyche. 

The process taught me how hard the brain works to avoid deep thoughts. It’s scary to venture into the darker spots in the sub-conscious that are often buried under layers of shallow, safe, things like to-do lists, sports scores and weather forecasts. As a 22 year old, I was so focused on what I wanted to become I was afraid to look closely at the person I  already was—what if I didn’t like what I found? 

But I stuck with the exercise and over time grew more comfortable with my thoughts. I also got to know Buster better. 

Or at least the online version of Buster. The 750words FAQ page led me to Buster’s personal site and various social media channels. I was instantly intrigued—he was so transparent online.  

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I found his online presence was honest, self-aware and unapologetic: this is who I am, this is what I believe, this is who I love and this is what I do

It’s rare to find that online, which is why I wanted to meet Buster. 

I emailed him and a week later we were sitting at Cafe Cumaica, two blocks from the Twitter office where he’s worked for the past year after moving with his wife and son from Seattle. 

Meeting him was exactly what I expected it to be. As a deep thinker myself, I greatly enjoyed our conversation about 750words, life, work, and what it all means in the big picture. 

Buster said he made 750words because he likes to tinker, build, experiment, and find ways to be a better human. He wanted a safe place to store his thoughts online and knew others would too so he built it with others in mind and has watched it grow organically. 

750words wasn’t his Buster’s first attempt at self-improvement. He’s interested in the quantified self and often looking ways to learn more about himself and the world. Our conversation, which was both fascinating and honest, revealed that Buster’s continuous tinkering, learning, and self-reflection has helped him discover who he is and, more importantly, he seems satisfied with what he’s found. 

A self-proclaimed over sharer, Buster has a very public life. His ideas and stories live in all corners of the internet—the obvious places like Twitter and Instagram to more unique places like Medium and LiveJournal (where his online life began). His contributions to the online world are a balanced mix of current events, general musings, and photos of his wife and adorable son Niko—not to mention his fascinatingly boring (his word not mine) goal to take a picture every night at 8:36

I told Buster I was impressed by his openness—it takes a lot of confidence to show the world who you are. His response was that he had insecurities like everyone else but, despite that, thought privacy was overrated. 

To me, that was Buster saying, This is who I am, why hide it? 

When he was younger and living in Seattle, he had several groups of friends and a slightly different identity in each group. Keeping the different stories and identities separated started to wear him down so he hosted a “Worlds Collide” party where all his friends could meet. The party didn’t cause his life to implode and afterward he decided to be the same, authentic, Buster wherever he went. 

That’s what he is doing today. Buster online is like Buster offline. Who he is at work is who he is at home and out with friends. 

When meeting someone that seems to have a sturdy grasp on the world and where they fit into it (or at least a better grasp than yourself) it feels right to ask them the questions that keep you up at night. 

I confessed to Buster a thought that’s been holding me back for awhile, 

"I worry I’m not creating enough value".

Is what I want to do enough? Should I be doing something better? 

Buster said he used to think about that a lot too, he used to worry about creating something meaningful for the world. But creating value is such a nebulous thing: what is valuable? Does it count if you help someone else create value? What if you create a lot of value but no one knows you were the driving force? Or what if you never fully understand the value you create? 

He said people try to save the world, but to some extent that’s an insecure desire. You want to create meaning for the world to prove to others that your life was meaningful; that you deserved to be here. 

Yet the reality is that just being born gives you a right to be here. 

Alternatively, if you knew who you were and you loved that person, you wouldn’t be so concerned with doing something to get others to love you; to remember you. Then time spent worrying about creating value could be invested in more productive things like learning, practicing, enjoying the people around you, etc  (which would quite possibly lead to a greater impact anyway). 

That will stick with me for a long time. 

Discover who you are and what you love, then spend your life investing in yourself and the things you care about. 

You can spend your whole life chasing meaning and value but ultimately in this chaotic and unpredictable world the majority of what happens in life is far beyond your control and, from Buster’s perspective, often depends on luck. 

If you can shift your focus to creating the best version of yourself —instead of meaning for an uncertain world—odds are high that you’ll live a good life and likely create something that makes the world a bit better in the process. 

Which goes back to me in 2011, struggling to write 750words because I was afraid to be authentic, because I felt pressure to be something to someone else. Just like Buster said, I had to prove my worth so I was searching to create external meaning.

I still use 750words frequently. The difference is that for the most part 750 words is easy to hit. I’m growing more and more comfortable accepting the real me—from the wonderful and fantastic parts to the flawed and unsavory ones that I formerly worked so hard to avoid.

It’s tough work to figure out  who you are, what you believe, who you love, and what you do. 

But if you have the courage to figure it out, you’ll live an authentic life. That, as my conversation with Buster revealed, seems like the best way to live. 

… 

Thanks to @jeannineyeah (officially my unofficial editor)!

Feeling Alive | A big update

This is the last of post of my three part series about why we love quotes but often ignore their advice. You can find the other two here and here

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Writing makes me feel alive.

It has since my early years in college when I was struck with a strong desire to share stories and ideas with the world.

At the time I didn’t know how to tell my own story and I didn’t have the courage to put my own authentic ideas out into the world for anyone to see.

My solution was to tell the stories of others. I started, msuCatalyst, a website sharing insights and stories about interesting students, faculty and alumni of my university. I could share ideas and stories, help students pick up life tips and keep my own story and ideas to myself where they felt safe.

The first dozen times I reached out to someone asking for an interview I was certain the answer would be no. Why would anyone be interested in sharing their story with some random sophomore? To my great surprise, the opposite happened—people were honored to be asked and excited to share their story. It wasn’t just around campus, either. During a summer internship in San Francisco I started a discussion in a LinkedIn message for Michigan State Alumni and five, five!, people responded they’d love to meet and pass along the wisdom they’d gained since college. The meetings were exhilarating and I loved the challenge of condensing their insights into interesting articles.

As with many college passion projects, it fizzled after the second year; however, my penchant for learning from people did not. With two years of college under my belt and guidance from an exceptional teacher, I decided to tackle a bigger challenge: 52 Cups of Coffee.

My experience meeting 52 new people from all parts of the world was life-changing, challenging, emotional, fun, unpredictable, thought-provoking, rewarding, terrifying, uncertain, joyful and more. Experiencing the ups and downs of the project made me feel alive. I can’t count the number of times I walked out of a coffee meeting on cloud nine, my mind racing with new ideas or my heart full after feeling a deep connection with a person I’d only just met. But it wasn’t just me. 52 Cups readers felt it too, and I’d feel the same exhilaration when I’d read a kind comment or email from someone positively influenced by the story.

52 Cups was one of the hardest things I’ve ever done, but also the most meaningful. I will never forget the indescribable feeling of satisfaction I experienced the day I posted the 52nd Cup.

So why, then, was my next major life step taking a 9-5 job doing very technical marketing for a tech company in San Francisco?

Because when I wasn’t busy writing stories in college, I was getting a degree in Marketing.

Marketing degree =  job in marketing after college.

Right?

Connecting with strangers and sharing stories wasn’t a real job. It was a hobby. My default assumptions what that hobbies don’t pay bills, degrees pay bills, which meant it was time to find a job in marketing. So I did. I found a great job at a great company with great people—and I was miserable.

When you follow up a year spent doing something that makes you feel alive with a 9-5 desk job (and 90 minute commute) it’s tough to be happy. But that didn’t stop me from trying. I found endless reasons why staying at my job was the right choice and chasing a crazy dream to travel and talk to people was far-fetched, foolish and irresponsible.

There was clearly a void in my life so I subconsciously started looking to fill it. This led me to conversations with good friends and lots and lots of reading. The emerging trend was that true happiness and success came from taking risks and chasing passions. This was the motivation behind this three-post series: advice tells us to chase crazy dreams, but the majority of people aren’t. Why? Are people wrong or is the advice wrong.

I decided there was only one way to find out: I started saving money so I could quit my job and jump back into the world of meeting people and sharing stories. Writing that sentence makes it seem like such a simple decision—like I just woke up with the confidence to trade in a stable, well-paying job for a life filled with uncertainty. I didn’t, I spent weeks filled with anxiety second guessing myself and the decisions I was making.

A major turning point was the night I received a text with a link to the The Risk Not Taken, the personal account for Bonobos founder, Andy Dunn. In the story was a line that echoed what Cup 30 told me about uncertainty and worst case scenarios:

The day after the Decision Elf visited me in the shower I saw a close friend at Stanford. I informed him of my decision — against an intimidating financial backdrop — to start a company instead of taking the job. I’ll never forget what he said because it rang true to the moment:

You’ll never starve, and you’ll always have a place to sleep. Worst comes to worst, you can always stay on our couch.

The post helped me see that I have supportive friends and family looking after me, employable skills, and a tough heart: if I made a decision and failed, I would find a way to pick myself up and make the most of the situation. I realized I would rather fail chasing a something important to me than succeed at a job that felt empty.

So I quit to travel and launch a fresh round of 52 Cups. 

And last Tuesday, I sat down at a lovely cafe in San Francisco to drink Cup 1. It was amazing. I left feeling alive. I remembered what it felt like to be doing something you love. 

Where will it all lead? I have no idea. But, despite the fear and uncertainty, it feels right. It’s going to be an adventure and I hope you’ll come along for the ride (you can now subscribe to get the Cups in your inbox!). I’ll be posting Cup 1 next week(!) and have fun updates to share soon.

At the end of 52 Cups round one, I shared this take away:

Because I know that if I can continue to figure out what I love to do, find the courage to do it, and do it well— life will work out—and have a lot of fun in the process.

It’s time I took my own advice and start to feel alive again.

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Thanks to @jeannineyeah (officially my unofficial editor) for reading this.

Conspiracy Theories and Quitting

This is the second in a three part series about why we love quotes but often ignore their advice. Read the first post here.

When you want something, all the universe conspires in helping you to achieve it.

This is a line in The Alchemist, the international best-seller written by Paulo Coelho, about a boy on a quest to Egypt after recurring dreams lead him to believe there is treasure there waiting. Ralph Waldo Emerson had a similar quote: “Once you make a decision, the universe conspires to make it happen”.

My simple interpretation: when you fully commit to a goal, opportunities emerge.

You can find countless quotes that share the same core thought: take risks, have faith, or to be cliche, just do it.

So why aren’t more people taking risks?

The surface level answer is that risk taking requires a great deal of courage and a healthy dose of trust. We can have a list a mile long with solid reasons why we should take a risk, but never take it because of the dialogue of dangers running through our minds:

  • It might not work.

  • You’re going to lose all your money and go broke.

  • You’re not smart enough to make this work.  

  • You don’t have the right skills for this.

  • Everyone is going to judge you when this fails.

Courage is having the ability to see these thoughts are rooted in fear, not reality and faith is trusting that regardless of what happens, you’ll figure it out and land on your feet.

Here’s my confession: I’ve spent the bulk of the past three (or more) months thinking about quitting my job. My comfortable and stable job at a fast-growing company with great team members and awesome benefits—a job that seems silly to leave.

Why? The simple truth is that while the job was an incredible learning experience, it wasn’t the right fit for me and the longer I worked the more apparent it became that I was avoiding doing the work that I truly loved.

I have never worked on a project that made me feel as alive or fulfilled as 52 Cups and I slowly realize that I needed to jump back into the world of conversation and adventure.

But I kept stalling. I told myself that no rational person quits a great job to travel and write about strangers they meet. And continued to tell myself I couldn’t quit, despite my growing unhappiness. It was a running dialogue: it’s irresponsible to quit your job, it won’t work, you will fail and be judged, you’ll go broke, you’ll never find a new job, you’ll ruin your career, etc.

It seems overly dramatic and harsh to write it out, but at a point in time, these irrational thoughts seemed very rational to me (and I’d be surprised if I’m the only one that’s ever had thoughts like these). Fortunately, I have truly wonderful friends that believed in me at a point when I didn’t exactly believe in myself and their encouragement helped me realize the worst case scenario wasn’t nearly as dramatic as I’d led myself to believe.

Someone very close to me sent a link to this fantastic post by the Bonobos founder, Andy Dunn, titled The Risk Not Taken (absolutely worth the read), which eloquently conveys the same realization my friends help me understand:

You’ll never starve, and you’ll always have a place to sleep. Worst comes to worst, you can always stay on our couch.

In the event of utter failure, I am fortunate to have wonderfully supportive family and friends that would love me whether my project succeeded or failed. The type of friends that would let me crash on their couches (which I did several times during my nomadic year). Friends that would happily forward my resume along to hiring managers. 

My worst case scenario is that my big vision doesn’t work out and I have to find a “real job” again. That doesn’t seem half bad and I realize how fortunate I am to be in such a situation. 

What all of these great conversations with close friends taught me is that it’s not failure that I’m afraid of—because deep down I think I believe that I’ll land on my feet—what I’m afraid of is discomfort.

My life is comfortable. I have a steady income that provides security and predictability. Why rock the boat and jump into a world that is unstable and unpredictable? Why leave a nicely paved road for a rocky dirt path? (What other ridiculous metaphors can I insert here? There are so many to chose from.)

But, like Paulo Coelho predicted, as I became more and more consumed with the idea of leaving my job to travel and write, small encouraging things started to happen that made the idea seem more and more appealing. Nothing crazy, a few thoughtful emails from people sharing how 52 Cups had inspired them to start a project, friendly tweets from people finding the project, wonderful encouragement from the people that know me best.

These small things compounded until I reached the tipping point: the excitement of jumping into the project outweighed the fear of discomfort. 

So I gave my notice at work.

And today is my last day.

Monday I jump headfirst back into the world of conversation and adventure, without certainty as to where it will lead but trusting that this is the right move that will lead me where I need to go.

And I hope you’ll be a part of the adventure. 

Stay tuned! 

Thanks to @jeannineyeah (officially my unofficial editor) for reading this.

 

Good communication is as stimulating as black coffee, and just as hard to sleep after.

—Anne Morrow Lindbergh

Ran across this sentiment and had to share it. Over the course of my 52 Cups, I so often left a meeting and pulled out my notebook as quickly as possible so I could write down all the ideas running through my mind; ideas inspired by great conversation.

It’s been too long since I’ve felt that feeling and I think it’s time to fix that.

More details to come.

:)