Here’s the fantasy:

1. Book a private island for a week.
2. Stock it full of your libation of choice (I’m thinking Kahlúa but you do you).
3. Crack open a brand-new fabulous-looking journal to capture the stream of epiphanies, world-class ideas, and life-changing transformations that will surely flow out of you.

Here’s the reality:

1. You like the idea of a personal retreat, even if you aren’t sure what it means (or if it involves psilocybin). (There usually isn’t psilocybin.)
2. You have good intentions of planning a personal retreat.
3. You let the flow of life wash over you and then look! Another year down the drain without going on a personal retreat! (Insert the *wah wah* sound here.)

Remind me what a personal retreat is again, and why I want one?

• A personal retreat is a dedicated time where everyone else in your life buggers off so you can focus on “me, myself, and I.” (To be clear, you’ll be focusing on you, not me. But I’d be flattered if you went on a personal retreat all about me; be sure to drink lots of Kahlúa and tell me how it goes!)
• A personal retreat is an experience with yourself that provides clarity and growth (I know that sounds like gag-in-the-mouth corporate-speak, but I do mean every word: experience, clarity, and growth).
• I used to run CEO advisory boards, and we’d talk about needing “to work on the business, not just in the business.” As CEO of your life, let’s run with that. A personal retreat is you getting away to spend time ON your life, not just living IN your life (usually on autopilot, because that’s what happens when we don’t step outside the routine to see what’s really going on).
• Helpful clarification: a personal retreat is not a day to “unplug” with an exfoliating scrub at the spa or 18 holes on the golf course or riding on a downtown Philly bus tour. Those all sound fabulous and they are called “self-care” and “being a tourist” … and definitely not a personal retreat. (Self-care and tourism are important, and possibly the topic of a future blog post, but just not what we’re talking about today.) 👈But you can tack those things onto your retreat, of course … who am I to stop you from seeing the Rocky Balboa steps in Philly, after you’ve had an insightful day of working ON your life?!

How EXACTLY do I plan a personal retreat, like in 6 steps?

STEP 1: The When.

• Key point: If you don’t book time in your calendar this puppy will never happen.
• Minimum recommended time? 4 hours. Surely you can carve out an afternoon for a little You time?
• Maximum recommended time? I’d think after 5 – 7 days you’d be sick of yourself, but if you can handle 2 weeks of All Things You in Bali, go for the gusto.
• Ideal recommended time: 6 hours – 2 days.

STEP 2: The Where.

• Find an inspiring location. I’ve told you before (in a blog post? At a cocktail party? I don’t remember where) about my friend Kevin who used to take the train from Chicago to Kalamazoo for the day. He’d sit in a nice hotel lobby, get his life all sorted out, then hop on the train and be home for dinner that night.
• Something happens when we immerse ourselves in new and novel places. Our eyes open up to sights and sounds that lead to new perspectives—just what we want on a personal retreat. You don’t need a high-end budget to experience a refreshed environment (because we can’t all just zip over to Monaco for a long weekend on the PJ). Inspiration for places to retreat to:

* Forest preserves (if you’re the outdoorsy/ camping sort)
*A coffee shop that will let you loiter for a while (I did one once in the open eating area of a Whole Foods in Chicago and it was inexplicably insightful)
*A rented (or borrowed-from-a-friend) cottage/ cabin/ condo/ lake house/ Tuscan villa
*A local hotel for a “retreat staycation” (or even just the lobby, like Kalamazoo Kevin)
*One friend goes to a local monastery to write and reflect in a beautifully austere room, for a shockingly low nightly rate
*Google “retreat locations near me” (but maybe stay away from the highway rest stops)
*In case of emergency/ zero budget/ perilous resources: your home will do—if you sequester yourself away from the parasites people you live with, and if you can create a nice little space to get reflective and creative (I’m picturing a quaint attic or a cozy den or a padded cushion by a bay window, but any place will do if you’re not living in constant fantasy of living in a pretend movie set, like me)

STEP 3: The Why.

• We’re operating under an assumption that you want the aforementioned clarity and growth … but that can still feel squishy. You don’t want to show up at your retreat like a deer in headlights, writing “WTF?” on page one of your new notebook.
• Try answering this question: what would feel wondiferous to plan/ think through/ reimagine/ reflect on/ prioritize/ map out/ noodle about/ redesign/ blow up and rebuild? Pick one or two of those things and write them in all caps on a page. Examples from my clients include (in caps, for effect):

*GET BACK IN TOUCH WITH MY PRIORITIES IN WORK + LIFE
*REDESIGN THE WAY I WORK WITH CLIENTS
*MAP OUT MY CAREER PLAN FOR THE NEXT 10 YEARS
*DREAM UP MY IDEAL RETIREMENT (YEARS 1 – 5)
*BRAINSTORM WAYS TO LIVE WIDER (WITH VITALITY) AND DEEPER (WITH MEANING) ____
*IDENTIFY WHAT TO STOP, START, AND CONTINUE IN MY LIFE
*GOAL-SET WHAT I WANT OUT OF THE NEXT QUARTER
*REFLECT ON WHAT KIND OF BUSINESS I WANT TO BUILD, AND WRITE OUT THE FIRST 10 STEPS TOWARDS LAUNCHING IT
*WRITE OUT THE THINGS I AM PROCRASTINATING AND GET CLEAR ON ACTION STEPS FOR EACH ONE
*SCENARIO-PLAN WHAT WOULD HAPPEN IF I TOOK THE RISKS I HAVE BEEN AFRAID OF TAKING (I.E.: LEAVING MY JOB AND MARRIAGE)
*DRAW A MIND-MAP ON POSTER PAPER OF ALL MY PRIORITIES AND HIGHLIGHT THE MOST IMPORTANT AREAS OF FOCUS
*SCHEDULE MY IDEAL WEEK IN MINUTE DETAIL FROM THE MINUTE I WAKE UP UNTIL MY HEAD HITS THE PILLOW
*CREATE A “NO” LIST OF THINGS I NEED TO CURB/ EXIT FROM MY LIFE
*IDENTIFY AND CELEBRATE MY ACCOMPLISHMENTS OVER THE LAST 12 MONTHS

• What would make you feel like your 6/ 24/ 36/ 500-hour retreat was a success? What insights or answers would make you feel like the time was well spent? There’s your why.

STEP 4: The How.

• Once you’ve identified what you’d like to chew on, it’s really all about asking yourself big and important questions … and answering them honestly. (That’s what coaching is in a nutshell: asking questions and then asking probing questions about the answer, and then asking more questions about the answer to the probing question, and then valiantly trying to navigate out of the Q&A wormhole.)
• Want 10 Questions to Get You Pontificating Your Life? Sure you do.
  1. These are the things I am proud of over the last six months (accomplishments, tough-but-important conversations, wins, progress towards goals, books I read, mindsets I chose, things I made, etc.):
  2. These are the five words that describe how I want to feel in my life over the next six months:
  3. When I look back on my life six months from now, this is what I want to be able to say I did:
  4. When I look back on my life six months from now, this is what I want to be able to say I didn’t do:
  5. These are the things I am procrastinating, along with what I plan to do about them (if anything):
  6. Here is where I plot my life today on the “Astonishingly Alive” framework, and here are my observations about why I chose that plot point:
  7. My ideas for how to widen my life over the next six months with more vitality include:
  8. My ideas for how to deepen my life over the next six months with more meaning include:
  9. If I died tonight, here are five words I’d use to describe myself and my life:
  10. Here are my specific action steps that I want to take as a result of my musings above:

• Hungry for even more? Try this resource of “48 Life-Jolting Questions” if you need a kickstart.
• Fair warning: be careful not to have your retreat turn into a run ‘o the mill working session. I know it feels delicious to accomplish things, so if you have a report to write or a performance review to trudge through or a spreadsheet to chip away at, please don’t compromise your retreat time to just cross stuff off your list. (I’m feeling strangely defensive about this point! Maybe because I have steamrolled my own retreat days with to-do’s? Guilty as charged *insert gavel banging sound here*.)

STEP 5: The Return to Earth.

• Yay for you! You went on a retreat and learned things about yourself! You maybe even feel transformed, or at least like you’re on the cusp of everlasting, meaningful change. But then your life kicks into gear and you have to finish that PowerPoint for work and then pick up your prescription and then buy a birthday card and then respond to that urgent Slack from your boss and then mow the lawn. But what about the supposedly Transformed, New and Improved You? When are you going to fit your metamorphosis in? What about the “action item outputs” from your retreat? “Returning to earth” from a personal retreat is like coming back from a vacation where you swore that “things are going to be different in my life from now on!” … only with 12X more pressure. How does one avoid falling into the Life as Usual Trap?
• Steps shall be your friend. Epiphanies are great, but they’re ideas floating in the ether unless you turn them into actionable steps. Decisions are empowering but they’re worthless unless you take steps towards implementing. Brainstorms are fizzy and fun and then pointless unless you do something with at least one of the scintillating ideas. One at a time will work. Steps. What are the first three things you’re going to do as a result of your ah-ha’s? Steps.

STEP 6: The Frequency.

• I am a fan of a 6-hour personal retreat every quarter. Let’s math this up for a sec: 6 hours x 4 retreats a year = 24 hours. That’s one day every year of your life, you’re right. Because decimal places can powerfully and hyperbolically illustrate a point, take a look: that’s 0.0027% of your year. You are worth taking at least 0.0027% of your year to reflect on how things are going and where you’d like to steer your existence moving forward. (If you debate me on this I will give you the look I give with my right eyebrow raised—the look that demonstrates I BEG TO DIFFER.)

Q&A:

• Can I do this with a friend? Yes (*answered slowly as I think about how to nicely say this next part*), as long as your friend isn’t an asshole. Supportive, motivating people are cool to retreat with! Debbie Downers not so much. You be the judge.
• Can I sneak in a massage? Oh of course. I got all judgey a moment ago about mixing up the purpose of retreats and self-care-refresh-missions, and I’m not your Mom … you get to do what you want! It’s delicious to go away, have a crisp morning walk, then do some retreat reflecting, then get a fancy pedicure, then do some more retreat thinking + planning, then have a lovely lunch with a crisp glass of Sancerre … by all means, mix and match the reflection and recreation! Just don’t go for a spa weekend and wonder why you didn’t come back with deep revelations about your future.
• The Q&A section is now closed because this article is getting too long.

What’s next?

So there you have it: 6 steps towards having some quality, contemplative alone time with yourself, inclusive of 10 questions to seriously interrogate your reality. I dare you to devote at least a half day to a personal retreat and tell me it wasn’t time well spent. Last I checked, you only get one go at this life, so why not spend 0.0027% of your time each year towards making it one worth living?