Yesterday my team at the office held our annual off-site planning retreat. It is a great tactic to force us to step aside from the day-to-day hustle and really spend some time strategizing for the upcoming year. Many organizations do this in some form, but why not do one for yourself as an individual? Here are some tips for holding your own Personal Planning Retreat.





Our team holds their retreat before the end of the year. We run on a July to June fiscal year, so we tend to meet in late May or early June. This allows us to plan for the year ahead.

You can hold your personal planning retreat whenever you want, but choose a time that makes sense for you. Try to avoid extremely busy times, as you want to be able to focus and not feel guilty about being away for a day. If you have a day job, you might take a vacation day to do this, or use a weekend day.

A few timing options include:

  • Matching your office schedule: If you intend to do planning for your personal life and professional life at the same time (my recommendation!), then I’d suggest having your retreat line up with the operations schedule of your office. This way you can take your office needs into account when planning your personal efforts.
  • End of year: If you’re the type that is motivated by New Year resolutions, then holding your personal retreat at the very end of December might help you choose meaningful goals and sustain your efforts beyond the end of January.
  • Birthday: You might consider using your birthday as a trigger to remind you to have a retreat each year. Reflecting back on the past year and thinking ahead to the next is common at birthdays anyway, so you might as well put that thinking to good use.


Get away from your normal workspace. Our team holds their retreat off-site. We typically reserve a conference room at a hotel or meeting center. This year we went to our leader’s home.

For your personal retreat, you really need to escape your normal work surroundings. Otherwise you’ll likely find yourself getting sucked in to conversations with colleagues or checking your email instead of focusing on the task at hand.

Choose a location that meets your needs. You could work from a coffee shop, or check out a co-working space for the day. Borrow a conference room from a friend, or book a carousel at the local library. It doesn’t really matter where you go, as long as you can get away from your day-to-day work distractions.

Some things to look out for:

  • Plenty of space to spread out
  • Quiet (if you need it) or noise (if you prefer it)
  • An electrical outlet to charge your devices
  • Access to restrooms
  • Food and drink (either available for purchase or bring your own)


Writing an agenda in advance is critical for a successful planning retreat. For our team, we have a specific agenda with topics we’ll discuss, who is leading the discussion, and time limits.

Knowing what you’ll focus on helps ensure you’re prepared with materials and information the day of the retreat. Remember that this is a planning retreat. The goal is not to work on projects, but rather to think, plan, strategize, and brainstorm so that projects can be moved forward effectively.

Be sure to include time for breaks and lunch. You don’t want to burn out here. You can even treat yourself to something special. Get a fancy latte in the morning, and plan to grab lunch at a local restaurant if you’d like. This is your day.


Consider what items you’re planning on your agenda and gather any tools and information you might need. Our team planned to include a brainstorming session, so we brought along tools to use for that process. We also knew we’d be talking about reports that we needed to submit, so we brought along informational printouts to refer to.

Some items I recommend you bring:

  • Post It notes or paper and markers (for brainstorming)
  • Something to take notes – laptop, journal, paper and pen, etc.
  • Your calendar
  • Your to-do list
  • Your swipe file (if you keep a file of random ideas)
  • Chargers for your devices
  • A snack and beverages

During the Retreat


We always start our retreat with a discussion of our general goals for the following year. This is a great thing to do for yourself at your personal retreat as well.

For your professional goals, be sure to choose some goals that relate to your team. By choosing a personal goal that helps the unit meet their annual goals you’re helping the team and yourself. You can also choose other goals that are more personal, whether or not they are work related.

Here are some example goals:

  • In an effort to support your team’s emphasis on efficiency, set a personal goal to learn new software systems that will speed up your production.
  • If you’re aware that you have a hard time staying current on processes, whether it’s filing paperwork or answering email, set a goal to break the bad habit.
  • If you’ve always wanted to learn photography, set a goal to enroll in some classes or take a new photo every day.

Remember to choose SMART goals. These are goals that are Specific, Measurable, Achievable/Attainable, Realistic, and Time-Bound. Even better, choose SMARTER goals by adding in an Evaluation process and a step to Re-Do/Reiterate.

Evaluate Projects and To-Do List

For my personal retreats, I always do an “audit” of projects on my to-do list. This can take a couple hours (if you’re very busy) the first time you do it, but after that it is easier to maintain.

First, write out a list of any projects you’re currently working on or need to be working on in your work and personal life. Then, ask yourself if each project really needs to be on your list. If not, get rid of it. If yes, keep it on the list.

Next, be sure each project is broken down into the smallest tasks. Your goal is to identify the next steps for all your projects. Rather than write “Build Website” on your to-do list, break it down into sub-tasks, such as research web hosting companies, buy a domain name, outline website content, and more. Do this for every project.

Personally, I believe in having a master to-do lists with all my projects and their tasks on one list. (Okay, two – I have a work list and a personal life list.) This allows you to keep the full picture in mind when you’re setting deadlines and when you’re evaluating whether or not you can take on more work.

Plan Your Strategy

After you’ve identified all the tasks and projects, you may feel overwhelmed. I know I did the first time I did this. That’s okay! By getting all of this written down, your brain can stop trying to remember everything and you can form your plan of attack to get things done.

First, determine any hard deadlines for projects. Get those on your calendar and note the deadline on your to-do list. Then, looking at your calendar, work backwards from these deadlines to set personal deadlines for each task related to the project. Remember to build in time for thinking and brainstorming, when necessary. Also remember to build in time for others’ contributions – for example, give yourself time for having editorial content approved if this is a requirement for a work task.

The most important piece of advice I have here to to be sure to think of the big picture. Don’t commit yourself to two large work project deadlines the week after a family wedding will keep you out of the office for days. Don’t plan a family vacation for your busiest week of work.

Evaluate Ideas and Brainstorm

One more agenda item in your planning retreat should be to evaluate ideas and brainstorm. Hopefully you keep a swipe file – a file (or box, or computer document, or whatever) – of ideas. You know when you see something and think “Maybe I could use that idea for work?” or “That’s neat! I wish I could do that!”? Write those ideas down. You might not be able to use them at the time, but you never know when it might be handy.

Collecting ideas does not do you any good if you never look at them. As part of your retreat, go through your entire file and see if any of these previous ideas are now something you can use. If so, add them to your project and task list, assign your next steps and create your deadlines.

Your personal retreat is also a great time to brainstorm ideas for problems you’re having. If there is a challenge or need at work or in your personal life, schedule some time during your retreat to think about it. Be specific with your agenda, noting what topic(s) you’ll be brainstorming on. Then do some free writing or brainstorming exercises. For example, if you struggle to come up with a weekly topic for your blog, brainstorm a big list so that you don’t have to struggle each week.

Colored pencils and notebooks

Follow Up

Plan to Hold Yourself Accountable

Now that you’ve gone through the process of developing your strategy, updating your to-do list, and creating deadlines, plan to hold yourself accountable.

For our team, we went ahead and set the dates for our monthly staff meetings during our retreat. We put them all on our calendars, and set the format of our meetings. We’ll check in each month on the progress towards our goals. We also will have a mid-year and end-of-year check in with our leader on our individual goals for the team. We’re holding each other accountable.

For your personal self, set some time on your calendar to check in regularly on your plan, projects, goals, and deadlines. Get this on the calendar now, and guard that calendar space. Don’t move it to accommodate others – hold yourself accountable!

Treat Yourself

We always end our unit retreat with some sort of fun, team-building activity. Some years we have a book discussion. Other years we do an activity. One year we took a pasta-making class. We’ve talked about crafting or taking paddle boarding lessons for the future.

End your personal retreat by doing something for yourself. Try to pick something that gets your creative juices flowing, helps you to relax, or gets you moving. Take a painting class. Get a pedicure. Go hiking. Visit the zoo or a museum. Take some time out of your day to do something you ordinarily wouldn’t let yourself have time to do. Think of this time as reinvesting in yourself. Recharge your batteries and you’ll be better able to tackle the plan that you’ve outlined for yourself.



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