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The Startup Life: Great Doubt, Great Faith, and Great Effort

Here we are, starting the year at Groundwork! in our new BETA space, with a major renovation of our main work space planned for completion in the spring. You could say that we’re sitting pretty, especially considering that Groundwork! was nothing more than a “castle in the air” this time last year.

Thoreau quote

This is a favorite quote at the Groundwork! HQ


I think it might be interesting and useful to get down, dirty and transparent about how this whole “starting a coworking space” thing works. So I will be dedicating some posts to the nuts and bolts of our process this year. I’m going to start with the three pillars of Zen practice, which for me are three pillars for life in general and certainly for the startup life. These pillars are: great doubt, great faith, and great effort.

Great Doubt


My winding path to Groundwork! included painting hotel signs in Ecuador.


For a Zen student, great doubt is the big, burning question that brings a person to practice. This question could be something like, “What is this life?,” or “Why is there suffering in the world?” I think that entrepreneurs are motivated by a similar doubt. In a simplistic way, being an entrepreneur is about solving a problem that people face, and building a business around the solution. For me, entrepreneurship is more than simple problem solving. It’s about building the world I dream of.

When I hit thirty, I was living in Buenos Aires. I had recently left my job as a marketing director at a medium-sized company. There were many factors that influenced my decision to leave, but mostly I decided that my life was too short and my time on this earth too precious to work on somebody else’s dream.

I freelanced for a year, doing marketing and website design for clients while living in Buenos Aires. Then I got rid of most of my possessions and headed to a small beach town in Ecuador. I was searching for the perfect balance: the low cost of living and abundant fruit and seafood in Ecuador meant that I could live a healthy, simple life while working a few hours a week and surfing every day.

After a few months in Ecuador, the sunny facade started to crumble, and I realized that my life’s purpose was to do something more engaged, challenging, and stimulating. I headed back to the United States, seeing everything with new eyes after almost four years of living abroad. I observed my friends and family working long hours, spending time in cars, on smartphones, and in front of televisions. I saw people staying at jobs they didn’t like for security and benefits. I saw that many people were not connected to their communities and did not feel inspired to create new things.

A great doubt arose: do we have to live like this?

It seemed that something in our economic system was broken. And I started to dream of a way it could be different.

Great Faith

great faith

I stumbled across this image wandering the streets of Buenos Aires after a Zen retreat.


Our doubt needs a good dose of faith to keep us moving. I don’t see faith as a constant, unchanging belief in someone or something. It isn’t something we can put our finger on. It is alive and forever changing, and we need to feed the fire constantly.

For me, faith is the complete trust and surrender to follow my gut, and to explore my doubt. Faith means that if I dedicate my life to living my big, burning questions I will, as Rilke wrote, “live my way into the answer.” Doubt is a big, blinking light that says: “Pay attention HERE.” Faith is what propels us to take the first step in that direction. As our faith grows, it will eventually lead us to step off the cliff and place all of our trust in the universe. When you have great faith, you have the confidence to follow your gut into uncomfortable places that stretch you and force you to grow. As Thoreau famously wrote,

If one advances confidently in the direction of his dreams, and endeavors to live the life which he has imagined, he will meet with a success unexpected in common hours.


 Great Effort

whiteboard strategy

Each little step along the way is propelled by faith…


The final pillar of Zen practice is great effort, also translated as great determination. Great effort is our willingness to go after it again and again. In Zen, that might mean getting on the cushion and practicing earnestly every day. As an entrepreneur, it is slogging through the strategy, going after funding, setting goals, writing emails, blogging. Great effort is work. Even with the grandest, most powerful faith and doubt, we must do the work. Great effort can be downright boring, tedious, and unpleasant. As Paul Graham rightly pointed out in his essay on How to do What You Love, doing what you love does not necessarily mean you will love what you are doing every second of the day.

I can’t say that I love making sales calls, reading legal documents, or reworking cash flow projections over and over again. But I do love blogging. I love strategy. I love working with friends. And I love building Groundwork.

The interesting thing for me is that great effort is not tied to any sort of expectation about the outcome. Sure, as entrepreneurs we set goals and target numbers and we work like crazy to meet them. But ultimately my effort is not a numbers-hitting game. I don’t know the exact answer to my doubt, nor do I know where my faith will lead me. But I know I cannot ignore these things. I cannot ignore the fire burning inside me, and so great effort seems to be the only possible and appropriate way to live.

How ’bout you?

If this all seems grandiose to you, it is. But then again, so is starting a business. So if you’ve built any of your own castles in the air, take a look at your great doubt and great faith. If you find your faith is such that it propels you to take a few steps off the cliff of your own comfort zone, get ready. It’s time to work your ass off.

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1 Comment

  1. Freddie on January 14, 2015 at 12:25 am

    This is great that you two have started this organization! My wife had talked about doing the same in New Bedford a few years ago and sure enough, here comes one! Look forward to seeing what you do! I will watch closely! Maybe one day, we can start our own Castle in the Southcoast!

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