Tomorrow I get on plane and start a 25,000-mile journey around the world (I’ll share my first stop at the end of this article).  The purpose of the trip is to have a little fun and to hopefully inspire and encourage each of you to be intentional and proactive with your own plans and dreams.  With that in mind, I thought it would be good to start with something practical.  What’s the process I use for trip planning?  How can you use it to plan exciting trips before and during retirement?  Here’s the process I use:

Start early

Each year, around this time, I sit down to plan our travel for the coming year.  Starting early is often a must if you want to make reservations at popular places.  It also gives you time to digest trip expenses and coordinate logistics (e.g. time off work, childcare, dog sitter).  And don’t underestimate the benefits of anticipation.  Booking early also means months of excitement and anticipation for you and your travel companions.  Can you book a trip last minute?  Absolutely (see also Travel Roulette).  But booking early often means more availability, more time to pay, less stress and more anticipation.


Repeat after me: “Planning a trip takes effort and it will cost me some money.”  Taking a trip is awesome, but planning a trip takes effort and a willingness to spend money, make decisions and even take a few risks.  Those things introduce friction into the process that cause many people to quit.  Push through this resistance by acknowledging ahead of time that the planning will have its challenges, but it will be worth it.


Throughout the year I jot down ideas and save articles related to places that look fun or interesting.  When I sit down to plan, I whiteboard a bunch of potential ideas and then we talk about them as a family.  We highlight several ideas depending on what we’re in the mood for, our budget, time frame and type of trip (e.g. outdoor, city, learning, relaxing, strenuous, group trip, etc.).

Basic Research

Once we have a list of places, we start doing some basic research.  What is the best time of year to visit?  What are the main things to see and do there?  How many days do you need to do what you want to?  What do available flights look like?  What lodging options are available?

Initial bookings

Once I’ve done the basic research and have the broad outlines of a trip, I try to get the big things settled.  For me, that usually means airfare and lodging.  Once those are booked, the trip is real (woohoo!).  And by getting them done early, you can take advantage of more availability (especially if you’re booking tickets with frequent flyer miles) and lower prices.  As I mentioned earlier, it also gives you time to digest expenses.


Once you start booking things, it’s important to get everything organized and outlined into a day-by-day itinerary.  The easiest way I’ve found to do this is by using the TripIt app.  When you get confirmation emails from airlines, Airbnb, rental car companies, and the like, just forward them to TripIt and it instantly creates a new trip for you and organizes all the details into an easy to read itinerary.   I can’t say enough great things about this app.  There’s a free version, but the paid version is totally worth it if you travel often.

Deeper research

At this point, I usually buy a few books to start doing deeper research about the place we’re visiting.  If we’re going to a city, I like the City Guides from Lonely Planet.  If we’re casting a wider net, I’ll get the country book by Lonely Planet or Rick Steves and I’ll also usually get something from Eyewitness Travel because the pictures help to give me a sense of the place.  I’ll also use the internet to visit tourist bureau websites, blogs, and travel sites like Trip Advisor where thousands of other travelers have written reviews and talked about their favorite things to do at the place I’ll be visiting.  As I find things that look fun or interesting, I’ll book them or make reservations and forward the details to TripIt.  This includes things like walking tours, restaurants, sites we want to see, activities we want to do, etc.  I leave room for flexibility and serendipity, but I try to give the trip enough structure so that we’re making efficient use of our days.  Once everything is planned and the departure date nears, I figure out what to pack


“When preparing to travel, lay out all your clothes and all your money. Then take half the clothes and twice the money.” – Susan Heller

What type of trip?  The first step to packing is to think about what type of trip you’re taking.  What’s the weather like?  What types of things will you be doing?  Packing for a ski trip is different than packing for the beach.  Packing for a destination wedding is different than packing for a camping trip.  Think about what you’ll be doing, what the weather will be like, what kinds of clothes and gear you’ll need and plan accordingly.

Pick a good bag.  Your luggage should match your trip.  If you’re hiking the Grand Canyon, invest in a quality backpack.  If you’re taking a quick weekend trip to celebrate your anniversary, a simple weekender duffel will do.  If you’re planning a three-week cruise, get yourself some sturdy luggage with a bit of capacity.

Lay it all out.  Lay everything out that you plan on taking and look through it with an eye on paring it down to the essentials.  Do your outfits mix and match?  Can you pare back bulky items, like shoes?  Are you taking things that you can just as easily buy at your destination?  If you take too much stuff, it’s stressful.  If you don’t take enough, it’s stressful.  Really think through what you’ll need and what you’re likely to use and try to strike the appropriate balance between not enough and too much

Pack it efficiently.  Once you have everything finalized, pack it up.  The goal is to get the maximum amount of stuff in the minimum amount of luggage, without exceeding the 50-pound weight limit that most airlines impose.  That means use packing cubes, compress, roll instead of fold, etc.  In other words, pack that bag like it’s a clown car.

What I’m taking

One of my inspirations for this trip is the pioneering female journalist Nellie Bly.  She approached her editor in 1888 with the idea of turning the fictional account of Jules Verne’s Around the World in 80 Days into reality and writing dispatches along the way.  All she took with her was the dress she had on, an overcoat, a few changes of underwear, some toiletry items and 200 British pounds.  Everything she packed fit into a small handbag.  Here’s what I’m taking:

  • The clothes on my back (shirt, jeans, belt, shoes, watch)
  • A 25-Liter Patagonia Black Hole Backpack
  • Two shirts, two pairs of lightweight pants, socks and underwear
  • A few toiletries (toothbrush, toothpaste, deodorant, floss)
  • A lightweight vest and a hat for cooler weather
  • My MacBook and phone so I can connect into my office and communicate with clients and people back home.
  • An Anker charging block
  • A Field Notes journal and pen
  • One paperback book (Meditations by Marcus Aurelius)
  • My passport, credit card and some cash

I’ll buy anything else I need as the trip progresses.  That includes clothes, which I will buy as needed (probably just a shirt here and there) and then donate when it’s time to change.  That might sound expensive at first, but it will almost certainly be cheaper than the baggage fees I’d pay if I were checking luggage on ten different flights.  It should be a fun and interesting experience and I’m looking forward to talking with you along the way.

The first stop is…drumroll…Hong Kong via Los Angeles.  I’ve got some fun things planned, including a visit to a famous street market, a hike called the Dragon’s Back, and plenty of food sampling.  I’ll talk to when I get there.  Until then…

Be Intentional,


3 days in Hong Kong
Around the world in 18 days