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How Taking Solo Retreats Benefits Founders and Entrepreneurs


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A while back, I flew from Minneapolis to Panama City and then took a water taxi to a backpacker resort. Before I knew it, I was swinging from an aerial circus hoop suspended from a sailboat over the sparkling Caribbean Sea. Though it wasn’t technically a work trip, I considered it good for business. I embraced play and disengaged, breaking some of the always-on conventions of entrepreneurship by taking a brief pause from my clients — as a mental health professional with a focus on entrepreneurship, podcaster, speaker, writer and mom.

I escaped to an “aerial and sail” retreat organized by the Paper Doll Militia. As an entrepreneur, it was exhilarating to suspend my responsibilities and spin and twist and torque, practicing aerial arts, a hobby of mine. If you were watching, you would have seen me skipping along the sandy beach with a huge grin on my sun-dappled face.

I’m a big advocate of solo retreats for founders and entrepreneurs. But I find that most of my clients — primarily business owners — put their needs aside and think first of sending their team on an off-campus mission to build culture, cohesion or the next big idea. They see arranging a retreat for their people as a great investment in the long-term success of their business. But a retreat for themselves? Indulgent. Trivial. Logistically impossible.

Related: This Founder Makes Sure He Has One Life Changing Solo Trek Every Year

Business leaders have difficulty stepping away. A Harvard study of CEOs found that those who did manage to take a break worked during 70% of their vacation days, leaving little room to recharge or reconnect with family, never mind reflecting on business or life goals.

I’ve been asked many times: What is the ROI of a founder retreat? That’s harder to answer, at first glance. The importance of corporate retreats is constantly reinforced as a business priority. Entrepreneur.com, for example, has at least a dozen stories on its site about corporate retreats, including these about the how and why of organizing one.

A quick search for “founder retreat,” “solo retreat” or “entrepreneur retreat” yields comparatively little. There is an interesting piece for business travelers and top executives who want to find a place to unplug, and another about the benefits of stepping into nature for a 20-minute break here and there (which I highly recommend). But I’d like to add something else.

The ROI of a founder retreat

Entrepreneurs are a primary business unit. We are core functions of our business, and we are also worthy of investment, fine-tuning and recharging. If we are in top form, that helps our businesses function.

A body of evidence shows restorative experiences, such as vacations, bring sharpened attention, mental clarity and inspired insights. An often-cited study commissioned by New Zealand Air in 2006 found a few days of vacation caused people’s reaction time to jump by an impressive 80%. And if you want a creative solution or fresh perspective, travel to a foreign country or spend time in nature. A brain wave is more likely to hit when you’re not at your desk or staring at your phone.

Being an entrepreneur can take up all our inner space. Tackling daily to-dos leaves limited bandwidth to consider the big-picture direction of our businesses — and our lives. The urgency of shipping or networking overshadows the seemingly non-urgent, existential questions. Am I happy? How can I improve my relationships? What do I want to accomplish in my work?

Retreats offer the opportunity to linger on big questions. Regular retreats make it possible to notice changes over time and to assess whether the default settings are still optimal. It’s possible that underneath the standard thoughts that permeate life there are some truly creative ideas waiting for space to be birthed.

I’ve known entrepreneurs who’ve decided on big changes after the quiet space of a retreat: the decision to sell a company, pivot into a new direction, pursue a new set of philanthropic activities or start a new company alongside their existing work. I’ve also known entrepreneurs who’ve decided to leave a personal relationship, pursue adopting a child or relocate their family to a new city based on the clarity that emerged during a focused retreat.

Setting aside time to bring attention to your personal growth and professional activities helps direct your energies and serves as a litmus test for when to say “no,” instead of churning through the pros and cons of every opportunity. A retreat saves this energy. It makes “no” easier and “yes” clearer. When you don’t make time for these big life questions, it also affects the business.

Related: 7 Ideas for Sabbaticals That Will Recharge You for Success

How do you retreat?

A retreat is different from a vacation, which might be an all-inclusive, drinking Mai Tais on a beach situation or a backpacking trip through northern Thailand. When I went to the retreat in Panama, I was seeking to improve my strength, stamina and skills with some of the world’s best aerial coaches. It was an escape, but also a deep dive into something I love.

My clients have told me they appreciate these other dimensions in my life, and that I was on a sailboat pursuing my hobby. I’m showing it’s possible to carve out time from my responsibilities. That said, I have the support of my clients, colleagues and family. I also gave myself permission to take this time away.

The holidays are coming. For many of us, November and December are when we look ahead to booking a retreat for our teams. What about you? If you can’t take the leap into a retreat, ask yourself “why not?” What is holding you back? Why don’t you think you need or deserve this? What support system can you put in place at your business to make it happen? Give yourself permission to take a retreat, confident that investing in yourself will generate positive returns.

Related: 4 Tips for How Entrepreneurs Can Unplug and Recharge During the Holidays



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