Contemplative Entrepreneurship

“There is no greater gift you can give or receive than to honor your calling. It is why you were born and how you become most truly alive.” – Oprah Winfrey

In mid-May I took a short overnight retreat at Prairiewoods, a Franciscan retreat center in eastern Iowa. I was last there 4 years ago for a week-long silent retreat. As soon as I arrived I noticed how exhausted I was, but as I stepped into the woods I felt my spirit lift. My only fear was that an overnight retreat wouldn’t be enough to replenish me. My current budget and the schedule of my pet-sitting friend wouldn’t allow any more than that, so it would have to do.

Ode to a Coffee Maker

I rarely drink coffee in the afternoon, though it is a MUST first thing in the morning, but when I spied the coffeemaker in the guest house kitchen, I had to have some. As silly as it sounds, the act of scooping and smelling the coffee grounds delighted me. Several years ago, I bought a Keurig that I have become increasingly dissatisfied with; it works just fine but I don’t love the flavor. I intentionally schedule my life now so that I don’t have to hurry often, so why am I making coffee like I’m in a hurry? I savor the first cup of the day as I journal and contemplate the day before. Why waste it on so-so coffee?

Sitting with Sister Water

The next day I found my way to a bench by Dry Creek, which the sisters of Prairiewoods have dubbed “Sister Water.” The sound of a running stream is so soothing to me, and as I watched the water rush past in the full creek, I remembered something my mother said to me when I was in college over 20 years ago.  She was concerned about me, she said, because I was always pushing up stream. Truthfully, I had no idea what she meant at the time or what aspect of my life she was referring to. It’s only been in the past few years that I’ve recognized how frequently I expect things to be hard and thought that was just an indicator to work-strive-push even harder.

As I watched Sister Water flow naturally, I recognized that part of my exhaustion was from pushing upstream, trying to force things in my business that either won’t work or the timing isn’t right yet. It’s tiring work trying to make things happen. Also, the entrepreneurial culture exhausts me. I love many things about being a small business owner but the idea of working incessantly isn’t one of them. I left the full-time practice of law over two years ago to get away from workaholism and its attendant stress.

The Contemplative Entrepreneur’s Question

That’s when the idea of contemplative entrepreneurism came to me. It’s a mouthful, I know, and probably not at all original. But instead of working harder and doing more and getting to yes, I decided instead that I would focus on where things are flowing in my life and work. I asked myself:

“Where is there ease?”

There’s ease in my teaching. A new law-related teaching possibility has fallen into my lap. And where I once found teaching yoga at the VA Hospital difficult, there is now ease. I’m delighted to report that more veterans are showing up for class, so much so that we’ll be moving the class to a larger room next month. Also, I’m teaching an intro business class for new or soon-to-be health & wellness business owners on June 2, that I’m really looking forward to as fellow entrepreneurs sign up.

I also see ease in the part-time job I recently accepted. As a new business owner, my income is sporadic still. For a long time, I resisted the idea of accepting part-time work; it felt shameful, like I was admitting defeat. And frankly, I have come to love the freedom of setting my own schedule. Yet, once I sat down to think of what kind of part-time work I would enjoy, animals immediately came to mind. With very little effort, I acquired a part-time job as a kennel assistant at a dog training/boarding facility, where I get paid to care for dogs (and clean up after them), which I happily do every day of my life anyway.

Move Over Keurig

Once I returned home I bought myself a French press coffee maker – the antithesis of the Keurig. It takes time to make French press coffee – at least 4 minutes of brewing time – and it tastes incredible. I even froth milk for my dark-roasted coffee most mornings. It’s delightful to make the time for something I enjoy so much.

My ego screeches in fear that by practicing contemplative entrepreneurship I’ll never make any money; I’ll just continue to scrape by if I don’t hustle. In my heart I know otherwise. It isn’t hustle that has brought some of the best things in my life. Much of it has been gaining clarity about what I want, which takes time, and then waiting for the right time to act. You can’t force divine timing any more than you can force a good cup of coffee.

With gratitude,


Question for reflection: Where is there ease in your life that you can sit back and enjoy?

© 2018 Rachel Regenold

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