12 Steps for Hosting Your Own Entrepreneur Retreat

The last weekend of January 2016, I hosted my first-ever entrepreneur retreat called SPACE Retreat in the Great Smoky Mountains. That first retreat became a yearly occurrence, and an experience I look forward to each autumn.

This post covers the philosophy behind these retreats for 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 first 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 didn’t want “serious business development” to characterize the experience because I believe that more breakthroughs happen in rocking chairs and journals than in conference rooms and meetings.

Hard-working, ambitious people don’t need more programming on the weekend, another agenda to follow, or an additional to-do list to crush. Doers don’t need more doing. We need more thinking, and that thinking must be predicated on ample space to step back, ponder, dream, or even grieve.

Don’t you often have some of your best ideas when you’re in the shower, on a walk, or otherwise not hyper-focused on problem-solving? Don’t the best solutions sneak up sideways when you let your mind wander?

The irony is that any of us can create more space for thinking 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 for thinking and dreaming 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 spill jumbled thoughts into a journal without needing them to be an actionable plan.

With the investment of money in an experience designed by someone else—or, something as simple as a hold in your calendar too expensive to move—comes a new set of expectations. You expect enhanced clarity, and that expectation makes you more sensitive and attentive to your own thoughts and feelings.

Breakthrough comes. Why? When we pay, we pay attention.

Invite the right people.

At the first SPACE Retreat, I was the organizing principle. I personally knew and invited each person there, save one.

Granted, I used some icebreaker questions and journaling assignments 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.

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 one hungry, tactless bulldog type trying to dig information or an introduction out of the one wealthy 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, island hopping in Greece, or quitting a boring job. They scrape together a budget, book the ticket, or 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.

Orthogonal thinking involves new and non-obvious connections. Think of your thinking as a stew, and new people with experiences very different than your own throw in vegetables and spices you’ve never heard of. The result may numb your lips and take your mind to new places.

We become the company we keep. So if you want to do more stuff, join a network of doers. I never want to lose the habit of trying new things, and meeting new people only encourages that. Hosting a yearly entrepreneur retreat was something I had never done, but eventually it became something I was quite comfortable with and a way to meet new people, have new ideas, and dream up new things to try.

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.

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 lopsided 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 smart, kind, interesting entrepreneurs and solopreneurs who need to slow down and make space.

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.

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 her chronic discontentment. Money solves money problems, but not your other problems.

Prosperity is a mindset, not a circumstance, and contentment is a spiritual practice, not a state.

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.

Do your own entrepreneur retreat.

My friend, nothing is stopping you from grabbing a journal and finding a rocking chair.

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 no one will find you.
3. Turn off your phone. Better yet, leave it in another room or in your car.
4. Close your laptop and put it away.
5. Pull out a pen and cheap paper. For a SPACE Retreat, I recommend cheap journals over expensive ones. A cheap journal will give you permission to be messy, disorganized, and mediocre.
6. Write down several questions you want to explore. You can use mine or come up with your own:
   a. What am I usually doing when I should be doing something else?
   b. What are the things that have added the most joy, meaning, and purpose to my life lately?
   c. What is the single most profitable project I’ve ever had?
   d Who is my favorite client? Why?
   e. What was I doing when I was able to make the most money (output) with the least effort (input)? Could I replicate that?
   f. 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?
   g. 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.”
   h. What is the biggest challenge in my business right now?
   i. 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.)
7. 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?
8. Use your journal entries to map out a plan of attack and set goals.
9. Break down those goals into actionable steps.
10. Pick the first 30-minute sprint, and add it to your calendar.
11. Find someone who can ask you about your progress, and ask them to ask. Bonus: 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.)
12. Take definitive action.

Yeah, 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.

When you’re ready, here are 3 ways I can help you:

1. Freelance Fixes. This short guide walks you through 6 small but important “fixes” that you can make to raise your income without working longer hours. People really seem to like it.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make  6 figures as a freelancer.
3. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.