How to Have Planning Retreat for Your Business Any Time

In case you don’t know this about me yet, I *LOVE* to make plans.

I am a type-A list-maker, checker-offer, planner-loving freakazoid. 

So it makes total sense that my idea of an awesome vacation? Is a planning retreat with my mastermind buddies.  (I know. I’m a huge dork.)

That’s us at 10,000 Waves spa in Santa Fe last February, where we had just relaxed and detoxed after a day of working and planning. (Are we cute, or what??)

We were lucky enough to be able to do a planning retreat on the cheap; it’s only a 6 hour drive from Denver to Santa Fe, and we were able to stay rent-free at my in-laws’ house for the weekend while they snow-bird it up in Florida. 

But we’ve done other plan-a-thons as close to home as one of our group’s houses.  Here we are, working on our 2016 plans a few weeks ago.

The point is, building planning into my business routine has meant a HUGE return on investment for me, and it’s now an important part of my year. I couldn’t have accomplished nearly what I have without making big plans — and so I choose to make big space for them with a planning retreat.

If this sounds like something you’re interested in, I’ve put together some tips below from hosting a few of my own.

It pays to get away.

In my experience, it’s tough to do a planning retreat at home. It can be done! But it’s much more difficult to focus on your business when your family/the laundry/the pets/that wallpaper you’ve been meaning to take down are all vying for your attention. 

Now, that doesn’t mean you have to go far. If you can go to Hawaii always go to Hawaii, but if you can’t, it’s OK to find a more of a staycation vibe.  Borrow someone’s house in a different town, like we did. Take a hotel room in the city. Rent an Airbnb for the weekend.  Have a grown-up sleepover at a girlfriend’s house. Even if you go to a coworking space or the library for a couple of days, that works too.  Just get away.

If you can’t afford a big “trip” do it on the cheap (meeting rooms at your local library are FREE!). The point is to change up your environment.

It’s actually well known that getting out of your normal surroundings (and comfort zone) is a creativity booster, and this is a wonderful way to start your planning retreat in a conducive environment.

Enlist some buddies.

If you’re a micro business owner, like me, chances are you spend most days alone in front of a computer screen. I actually love working from home because I’m a bit of an introvert, but a planning retreat will feel more special if you have someone to share it with. 

Lucky for me, I have a wonderful local, in-person mastermind group that I meet with regularly, so I have a built-in group of planning buddies. 

Even if you only find one other person to plan with you, I think the community aspect really elevates a planning retreat to something more than just you, sitting in a room, making notes on a big old white board or sticky notes. 

Make a plan.

HA! Yup. I mean a plan for your planning.  (How dorky am I??) But actually, this step is pretty vital. Set a goal of what you want to accomplish, gather your tools (see below) and have all your supplies on hand (also below) before you ever get started.

This is ESPECIALLY important if your planning retreat involves other people. When we did our mastermind retreat in February, two of us had a LOT of work we wanted to accomplish, while the third was looking for more of a break from work. I wish we had talked about this more before we went! But it ended up working out fine. (She went for a run and other things while we worked.)

Create a very basic schedule you will follow. You’ll quickly discover: a weekend is not nearly as long as you think! 

Ask yourself:

• Will you work together, or separately?
• What do you each hope to accomplish?
• When will you have socializing BS time (because you know it’s gonna happen) and when will you really get down to bidness?
• What else do you want to do? (See the next tip!)

Come to a consensus and draw up a very basic schedule.  Here’s what ours looked like for a 3-day weekend (more or less):

Friday:

• Drive down to Santa Fe; stop for a picnic lunch 
• Arrive in Santa Fe around 4pm; stop for drinks at Zia Diner and pick up dinner 
• Dinner at home, get settled in, wine and chit-chat

Saturday:

• Breakfast at home.  
• WORK AND PLANNING OMG!
• 4pm reservations for private hot tub at 10,000 Waves (yasssss)
• 7pm dinner reservations at Joseph’s Table

Sunday:

• Clean up, pack, etc.
• Brunch at Tesuque Village Market
• Drive home.

As you can see, with everything else, we only ended up with about 6 hours of work and planning time!  When we do this again (OH YES! I said WHEN), I would like a little more planning time, maybe broken up more.

Plan for FUN.

Part of the beauty of a planning retreat is the RETREAT part! Even if you can’t afford to stay at a luxury resort and spa, you can recreate some of that feeling by planning in some fun.

Because we could drive to our destination and stay for free, we could splurge on a private hot tub and a really nice dinner out — even though some of us were on a tight budget!

Again, if you can go to Hawaii…  But if you can’t, bring a little of that feeling to you. Hit a local spa, go out for drinks or dinner somewhere swanky, get your nails done while you talk strategy, hang out by a pool somewhere — whatever works.

Gather your supplies.

When you’re getting ready for your retreat, start gathering your supplies.

Because we were doing a retreat-on-the-cheap, we took a lot of our food with us, some wine, and all our work and planning supplies of course.  We split up the meals equally so we all had something to bring.

Your circumstances will vary, and so will your list, but it might include:

• food, meals, snacks, alcohol, chocolate, etc.
• pens, paper, calendars, notebooks
• STICKY NOTES
• white board and pens
• music
• guides, courses, workbooks, etc. (See below!)

Get some help.

Not all of us can pay to go to a planning mastermind retreat with our favorite gurus! But thankfully, many of our favorite gurus make portable versions we can bring with us. 

Decide what you’re planning ahead of time. Are you working on a general, year-long business plan or something more specific like a course, your social media, or your brand?

Here are a few of my favorite planning resources:

• The Fresh Start 2016 Workbook from NiceOps.  I bought this in 2015, and went back through it again this year!
• The Create Your Shining Year in Biz Workbook from Leonie Dawson. Similar exercises, totally different flavor!
• Free Stress-Free Revenue Planning Guide from Tara Gentile. Because it pays to know your numbers
• Free Systems Chick’s Guide to Transforming Busyness Into Business from Natasha Vorompiova (signup in her sidebar).
• And Blogstorm (of course) to get your content marketing plan in place.

Awesome planners:

• The Mama CEO Planner* (awesome whether you’re a mama or not)
• The Passion Planner*
• The Day Designer*
• The Desire Map Planner

Note: The ones with an * have a FREE printable version you can print off to try out to find your favorite.  

My favorite planning system:

• Bullet Journaling

Whether you use a bunch of sticky notes or a beautiful gold embossed planner, planning is a VITAL activity for your business.  

I’d love to hear from you: Do you run a planning retreat for your biz? How do you like to do it? Do you have a favorite planning resource? Let us all know in the comments below!