Take a Thinking Retreat for Clarity & Strategy

If you can’t see where you’re going, how will you get there?

Josh Clark
7 min readSep 28, 2022
Photo by Jason Strull on Unsplash

As an entrepreneur, a thousand things scream for your attention every day.

But 99% of them won’t move you any closer to the life you dream of living.

Because the most impactful thing you do isn’t putting out fires.

It’s occasionally rising above the day-to-day fog and looking into the distance to determine where you want to go — a month, a year, or five years into the future.

Without getting clear on what you’re working towards, you end up spinning your wheels and getting nowhere.

Most of your time is spent in action.

To be most effective, you also need time to think and to plan.

That’s why seven years ago I started taking regular Thinking Retreats, and they’ve transformed my life and my business.

Some of my best ideas and biggest breakthroughs have been because I’ve taken time to rise above the fog.

What is a Thinking Retreat?

A Thinking Retreat is time away from your ordinary routine and responsibilities to get clarity on the future you’re trying to build and what steps you need to take to get there.

I got the idea from Bill Gates, who famously goes on two seven-day “think weeks” a year to spend time in deep thought and reading.

With small kids at home and day-to-day responsibilities in my business, I only go away for one to two days at most.

At minimum I do this at the start of each new year, to reflect on the prior year and plan for the upcoming one.

Sometimes I’ll do one at the start of a new quarter.

And sometimes as a “In Case Of Emergency Break Glass” tool, like recently when I had two key team members quit my company at the same time.

They were leaving for very different reasons, but the sucky timing and unexpected turn of events sent stress soaring and forced me to change my strategy for the next 6–12 months.

As a result, I did a Thinking Retreat, because:

  1. Situations like that can make you feel like a failure, feel discouraged, feel like giving up, feel like you’ll never “get there” (just stop me anytime)… and you need to get your head in a better place
  2. I needed to get clarity on what my strategy and priorities should be based on new circumstances

So in addition to figuring out priorities, I also shifted my perspective back to a place of positivity, which was even more important.

Planning A Thinking Retreat

So you’ve decided you want to do a Thinking Retreat. Now what?

Take the time

The first step — and the hardest — is actually taking the time to do it!

You might look at your calendar and think there’s no way you can make it happen anytime soon. That’s okay.

Look ahead on your calendar as many weeks into the future as it takes to find 1–2 days when you can get away. Put it on your calendar, and book a hotel.

Some people won’t understand what you’re doing. That’s okay, too. I’m giving you something I wish someone had given me a decade ago — permission.

Book a hotel

“A hotel? Can’t I just got to my office on a Saturday when no one’s there?”

Do. Not. Go. To your office.

Even with no one around, there will be some thing left undone on your desk, some note reminding you of a project, something to distract your focus.

And even if there’s not, when you’re at your office your brain is saying “I know this place, it’s time to get some work done!”

You need to get in a new environment that tells your brain “I’m here to think, to dream, and to plan.”

I personally like to book a hotel room with a view I can see from a table or desk. The more windows the better. It gets the inspirational juices flowing.

Special Tip: The hotel day rate

If you’re only getting away for a day and not an overnight, most hotels have a “day rate” that is steeply discounted — typically 50% off.

You can call to book it ahead of time, or if you already know they offer a day rate, just show up that morning and tell them you need a room for the day to get some work done.

Some co-working spaces rent private offices that can work for this too.

If you are booking overnight, be sure to ask for both an early check-in and a late check-out, to give you more time.

Even doing that, I typically will start my retreat at a Starbucks because the hotel won’t be ready until around mid-day.

What To Do On Your Thinking Retreat

Your calendar is blocked and your hotel is booked.

Now what the heck do you actually do??

Either at the beginning of the retreat or in the days leading up to it, I’ll make a list of the things I want to accomplish to consider it a success.

For a retreat at the start of a new year, this is my agenda:

  1. Reflect on the previous year — Wins, goals, lessons learned, travel, highlights
  2. Dream about the upcoming year — What would make it the best year ever? What should you focus on?
  3. Create specific, measurable goals for the new year with deadlines and at least one actionable step for each
  4. Create a first quarter battle plan to begin accomplishing goals

Other retreats, like the one I went on recently, are more about gaining clarity in a particular season. For those I’ll start with a list of questions I simply want to spend time trying to answer.

For a general Thinking Retreat, here are some questions to choose from:

  • What do I want out of life?
  • WHY do I want it?
  • Why do I want my business to grow?
  • What do I want life to be like 12 months from now?
  • What should my top priorities/goals be for the next 6–12 months?
  • What defines success in each area of life (marriage, family, business, spiritual walk, finances, etc.)?
  • How should I structure my time to accomplish my goals and meet my priorities? What does my Ideal Week look like?
  • What are the things that only I can do?
  • What should (key team member) be doing?
  • What should (my business) be doing to grow sales?
  • How are our processes working? Where must they improve?

On most retreats I spend the entire time just trying to answer some of the above questions, and still don’t feel like I’ve “finished” by the time it’s over.

Which brings me to final piece of advice.

My Best Advice

On my most recent retreat — you remember, the my-team-is-leaving-and-I-feel-like-giving-up one? — the best breakthrough I had, the one I really needed, wasn’t even something I worked to get.

I was just in the right place at the right time.

When I showed up at the hotel to check in, my room wasn’t ready. I hadn’t eaten lunch yet so I picked up a sandwich and went to a nearby park, where I found a picnic table with a view.

As I sat there, to my left I watched a homeless man pulling a trash can on wheels, going from one park trash can to the next collecting recyclables. He had no shoes on his feet, and his clothes were ragged.

Next, to my right I watched an elderly couple arrive and make their way to a park bench. She was pushing him in a wheelchair, and helped him onto the bench. They sat next to each other, talking, reading books, and enjoying the day.

In that moment, contrasting the homeless man on one side of the park with the elderly couple on the other, I was filled with a deep gratitude for life.

I was nowhere near that man’s situation, having to collect trash to make a buck. And I was on a path to enjoy a lifelong romance with my beautiful bride.

I pulled out my phone and wrote the following:

I am a blessed man.

I have a beautiful wife who loves God and supports me fully.

I have three amazing, beautiful children who fill me with joy.

I am in the prime of my life. My family and I are healthy. My parents and siblings are alive and healthy. I own a business that has provided for us for nearly 15 years. I have begun creating other streams of income. We have more than we need.

My goodness. Life is good.

Only four years ago, I dreamed about, hoped for, and believed for the life I have today. And here I am.

It feels so ordinary. It feels so normal. It’s easy to forget how good I have it. I need to more often remind myself of just how good life is.

I didn’t plan that moment. I didn’t go on the retreat consciously thinking that what I really needed was to find a fresh sense of gratitude for life. Yet it had found me, and it was exactly right.

So my best advice is simply this: be open.

If you try to force breakthrough, it won’t happen.

If you try to pressure answers to come, they won’t.

Take some time away on a Thinking Retreat to gain clarity or define goals, and you’ll be more set up to succeed in building the life you want to have.

Open your calendar and book it today.

Hi! I’m Josh. 👋🏻

About Me: Who I Am & What I’m Working On

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Josh Clark

7-figure business owner helping you make your life a little bit better • Topics include personal growth, business, writing, and living life with intentionality