4 Things Every Entrepreneur Retreat Needs

The last weekend of January, I hosted my first-ever entrepreneur retreat called SPACE Retreat in the Great Smoky Mountains.

Before too much time passes, I want to share the philosophy behind this retreat for executives and entrepreneurs, as well as some practical tips for creating space for yourself, as needed.

Curate the right experience.

One of the men I invited to the retreat asked me via email if the focus was “serious business development.”

My vision for the retreat was still very much in process at the time, so I appreciated my friend’s question. It helped to galvanize my beliefs about how people actually gain clarity and set direction for their organizations and ventures. I’ve become convinced that more breakthroughs happen in rocking chairs than in conference rooms.

That’s why I didn’t want “serious business development” to characterize the experience.

Hard-working, ambitious people don’t need more programs on the weekend, another agenda to follow or to-do list to crush. Doers don’t need more stuff to do. They need more space to step back, ponder, dream, even let their minds wander.

The irony is that any of us can make space for free. We can do it anywhere and at any time. But we simply don’t.

We usually don’t treat something as simple as space seriously until we quite literally buy into it and put it down in our calendars. We pay a premium to sit still, be quiet, and write down our jumbled thoughts without needing them to be an actionable plan.

With the outflow of money comes a new set of expectations, and those expectations, in turn, bring breakthrough.

At SPACE Retreat, I served as the organizing principle. Granted, I used some questions and some homework to grease the works. But SPACE Retreat was still only 20% business retreat. The other 80% involved concentrating cool people in one place and watching cool things happen. Sparks flew.

Photo Credit: Carrie Jo Pinckard of Texture Photo

Invite the right people.

The group dynamics matter, of course. One person with the wrong attitude or expectations can ruin the experience for everyone else. I didn’t want the hungry, tactless bulldog type trying to dig information or an introduction out of the uber-rich and very private entrepreneur. (SPACE Retreat was never intended to be a “networking event,” though some of the attendees have since helped one another.)

I decided to think of the retreat as a dinner party, and I used that schema to curate the invitee list: “Who do I want to have dinner with?”

The second criterion for acceptance was just as basic, if nuanced: Who do I know who does stuff? For a weekend, I wanted to immerse myself in a community of interesting people with interesting pursuits. They don’t just talk about an app idea or island hopping in Greece or quitting a boring job. They scrape together a budget, book the ticket, put in their notice.

Michael Simmons wrote a Medium story I really liked, and in it, he builds on the thesis that the number one predictor of career success is regular exposure to new ideas and new networks of people.

Disruptive ideas, both in the macro and in the micro, very personal sense, help us piece together new beliefs, new strategies, new plans of attack — in a word, breakthrough.

We become the company we keep. So if you want to do more stuff, join a network of doers. This year, I want to make a habit of trying new things, which included hosting an entrepreneur retreat. I’d never done that before.

The retreat was just expensive enough that price became the third criterion. The retreat attracted inquisitive doers willing to pay for an experience, without a guaranteed return on investment, whatever that means. Everyone else opted out.

The last thing that comes to mind is generosity. I wanted folks who would come looking for ways to give.

Photo Credit: Texture Photo

Focus on the right things.

Success in business involves more than doing. We’ve got to work smart, not just hard, which means working on our businesses, not just in our businesses; developing ourselves, not just strategy. As businesspeople, we must value both contemplation and action, or we end up with lop-sided lives — heavy on resources, and light on meaning and purpose.

Take several steps back from your business, and you’ll see an exponential growth opportunity. You’ll notice a hidden point of leverage that you would miss in a blur if you were moving too fast.

The key is to sacrifice Urgent on the altar of Important.

SPACE Retreat is about just that, creating space: space to rejuvenate and dream; space to goof off and rub shoulders with other fast-moving men who need to slow down; space to rest.

Space is hard for go-getters because it feels unproductive.

More is more, right? Cram each hour with tasks and hustle. Scream to a halt right before bed, set your alarm, and get up early to do it all over again.

You do that for weeks and months on end, and stuff happens. But the right stuff? The stuff you care about most?

Are we using work to engineer a lifestyle or simply creating new jobs? A job is not an asset.

Photo Credit: Carrie Jo Pinckard

Pick the right goals.

A lot of us need to reconnect with our hearts. I’m not suggesting that we paint our faces, hold hands, and sing “Kumbaya” (though let’s keep that option on the table).

I’m suggesting that ambitious people can achieve more when their minds and hearts come into alignment. In fact, hosting these retreats represents better alignment for me.

Nothing shocks an entrepreneur more than achieving a certain level of material success and discovering that money didn’t cure his chronic discontentment.

Prosperity is a mindset, not a circumstance.

Prosperity is a mindset, not a circumstance.

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Space enables us to reopen some discussions we’ve had with ourselves for years: Why do you work so hard? What’s all of this about anyway?

Space dredges up better questions, and better questions bring clarity. Clarity, in turn, helps us to set direction and move forward with confidence.

So bring your sense of humor. Bring a bathing suit. Bring whatever you like to drink.

Maybe I’ll see you at SPACE Retreat 002 in Oklahoma in March, or SPACE Retreat 003 on the Clinch River in April. If not, I hope you’ll carve out more space in your life to breathe and dream.

You can nominate yourself or someone else here.

Regardless, I hope you’ll spend some time in a rocking chair.

Do your own entrepreneur retreat.

Photo Credit: Carrie Jo Pinckard of Texture Photo

Here’s what I would recommend:

1. Add “SPACE Retreat” to your calendar — two hours minimum. Make it a thing.
2. Leave your house, office, or other familiar environment where you usually work, and go someplace where no one will find you.
3. Turn off your phone.
4. Put your phone in another room or in your car.
5. Close your laptop and put it away.
6. Pull out a pen and cheap paper. There’s something about cheap paper that gives us permission to not have anything figured out. Our thoughts and ideas can be messy, disorganized, and mediocre.
7. Write down one or two questions you want to explore. You can use mine or come up with your own:

• What am I usually doing when I should be doing something else?
• If my own personal happiness were off the table, what would I do?
• What is the single most profitable project I’ve ever had?
• Who is my favorite client? Why?
• What was I doing when I was able to make the most money (output) with the least effort (input)? Could I replicate that?
• What are the things about my work that I most dislike? Could I offload those to someone else like a part-time 1099 contractor or a virtual assistant?
• What excuses do I make for myself on a regular basis? For example, “I don’t have enough time.” “There’s too much
• on my plate right now.”
• What is the biggest challenge in my business right now?
• With that challenge in mind, what changes or adjustments to I need to make in the areas of 1) cashflow, 2) people, 3) strategy, and 4) execution? (Hat tip to so Verne Harnish’s book Scaling Up for those four areas.)

1. Dive deep into those questions. Be honest with yourself. Don’t be a victim. Do be generous to other people who have achieved the kind of success you want. Have they stayed focused in ways you haven’t? Have they remained consistent with certain habits or activities?
2. Use your journal entries to map out a plan of attack and set goals.
3. Break down that goal into actionable steps.
4. Pick the first step, and add it to your calendar.
5. Find someone who can ask you about your progress, and ask them to ask.
6. Pick a painful amount of money. Write a check to your “workout partner.” Tell him or her to cash the check if you don’t follow through with your plan of attack. (Read “How to Finish Anything” for more context on this approach to meeting goals.)
7. Do.

I’m convinced that more breakthroughs happen in rocking chairs than in conference rooms.

Test that hypothesis, and let me know how your entrepreneur retreat goes.

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Originally published at Austin L. Church.