Traveling Product Manager

It’s fitting that I’m writing this from the exit row of an MD-80 this evening on the way home from a customer visit.  I almost didn’t get the exit row, but I did.  I tried for an upgrade to first class, but I was 15th in line – it was a busy flight with a lot of high-status frequent fliers ahead of me.  But I’m thrilled to be in the exit row, with the lap-room available to type up these tips that will help you travel.

You can love to travel or hate to travel.  Either way, there are a lot of little things you can do that make travel easier.  At first, many of these seem like small inconveniences, but over time, you can adopt many of them as habits.  And the rewards add up – every little thing you do that makes it easier to be on the road makes travel better (or at least less onerous).  This is my first trip in almost a year – I’ve been doing all of my traveling for 2008 virtually – with GotoMeeting, WebEx and DimDim.  I’ll be back on the road again, so I’m dusting off what I remember from my road-warrior days, to make it easier now.

Frequent Flier Programs
When I first started traveling, I was on the road every week.  My travel agent suggested that I sign up for every frequent flier program, and every hotel rewards program.  So I did.  Over time, I found that focusing on a single airline provides the best payback – because you earn status that lets you

  • Go through shorter security lines at the airport.
  • Get on the plane first and grab the luggage space you need in the overhead compartment.
  • Reserve the “premium” seats – like exit row.
  • Get “bonus” mileage credit for the travel that you do – leading to free flights or upgrades later.

Status is a key component of the loyalty/stickiness programs that airlines run.  They need a way to differentiate their “fly from A to B” product from everyone else’s “fly from A to B” products.  As you fly more and more in a single calendar year, you increase in status from ‘regular passenger’ to ‘acknowledged passenger’ to ‘appreciated passenger’ to ‘of course we can, Mr. Sehlhorst.”  On American, that path goes from ‘Aadvantage member’ to gold, then platinum, then executive platinum.  Once you earn a particular status in a given year, you retain that status for that year and the following year.  Each year, your status, if not re-earned, drops one level.  So if you earn platinum status in 2008, you keep it for 2009, then drop to gold status for 2010, and back down to ‘regular passenger’ in 2011.

The right airline for you may be different than it is for me.  The airlines that fly into your “home” airport may be different than mine.  And the flight schedules from your home airport to wherever you tend to go may be more or less convenient on one airline or another.  Personally, I fly American Airlines whenever I can.  I know and like the planes, I like the “by price and schedule” implementation for booking flights online, and I especially like the service I’ve received as a platinum status flier over the years.  Apparently the customer service is even better for people who reach executive platinum status, but thankfully, I don’t have first hand knowledge.  Always a bridesmaid, never a bride.

American also has a program where once you reach a million miles (traveled or otherwise earned), you become “gold for life” – so even when you travel infrequently, you still have some status/perqs.  When you reach 2 million miles, you become platinum for life.  As someone who’s halfway between the two, who has enjoyed the benefits of platinum off and on (mostly on) for the last decade, I find that carrot to be pretty compelling.  Traveling with your family at the holidays is SO much easier when you have status, if something goes wrong one year (and it has).

I’ll add a connection, or wake up an hour early or pay a few (but not a lot of) extra dollars to fly American on any given trip.  Knowing I’m a little closer makes the trip better for me.  For you, picking the best schedule, or the cheapest flight, might be better.

My most valuable tip: When someone else makes a reservation for you, you usually get bad seats.  First – make sure your frequent flier number is associated with the reservation.  Second – fix your seats.  And if the flight is really full, check again 96 hours and 48 hours and 4 hours before your flight, a better seat may have opened up.  That’s how I made it to the exit row a few hours before my flight tonight.  I was in a middle seat on an oversold flight.

Frequent Sleeper Programs
The hotel chains have the same game going as the airlines.  “Stay at our hotels, and earn status and points.”  I probably have a dozen memberships, and they vary in quality.  Rather than go into details, I’ll say that I feel that the Starwood chain (Sheraton, Westin, W, St. Regis) has the best program.  As a Starwood member, I have never been prevented from reserving a room using “points” instead of cash (aka a free room).  When I was a platinum Starwood member, the complimentary room upgrades were always a very nice surprise, and happened frequently.  The only downside is that I can’t always find a Starwood property where I’m travelling.  If I can’t, I lean towards Marriott and Hilton as distant second place competitors.

Frequent Driver Programs
Is there anything other than Hertz?  I can always find a good rate on the cars I rent, usually get a one or two class upgrade on the car, and don’t have to wait in line – Hertz gold is free, and you get “status” from them for your tenth rental in a given year.  Your 40th rental in a year gets you “crazy status.”

Did I mention that I don’t wait in line to pick up (or drop off) the car?  Maybe every rental company has that service these days, but I’m blissfully unaware.

Frequent Traveler Intelligence

Bar none, the best place to learn everything about being a frequent traveler, and to get the best intelligence and insights about all of the programs is  Check out the “miles buzz” forums – there’s one for each major airline, hotel, and car rental chain.  Once you get good at maximizing the rewards you get from the travel you have to do, you get exposed to the extreme sports version of frequent travel – the mileage run.  People actually figure out the cheapest ways to fly 16 segments from Boston to Tokyo and back over the weekend, so they can earn that next level of status for the year.  It is an insane world.  The next time I’m on the edge of executive platinum, I might just try it.  I’ve let that brass ring slip through my fingers year after year.

You also learn really obscure stuff – like the sequence in which meals are passed out in first class (it varies by flight direction) – so if you are really craving the glazed chicken, and hate the idea of veggie pizza, pick the right seat.

Another very handy site is  You’re trying to pick your seat for a flight on an MD-80?  Where do you want to sit?  Seatguru shows you a map of most planes, as they are configured by the different airlines.  On that map, you see if a seat has shortened or extended legroom (it varies within the planes), has a power outlet for your electronics, or if anything else is especially good or bad about a particular seat.  Desperately need power on that late night flight home so you can write your blog post?  Better make sure your seat has a power port. has proved to be really useful too.  Every time I travel to a new city, I bookmark the page for that city in my browser.  Over time, the list has become pretty long, but with all the banner ads and animation that clutter the site, I love that I only have to click once to find out how to pack.  There are probably some much better desktop widgets that you can use to find out the weather without ever going to the site – but what was around 10 years ago was never compelling.  Add a comment or shoot me an email if you have a favorite weather-checking solution.

You can also check flight status online or have your airline send you a text message (or voicemail) if there are changes to your flight schedule.  Those can be pretty handy things.  You can even request an upgrade to first class over the phone while you’re driving to the airport if you want to try for an “impulse upgrade” at the last minute.

Your Computer on the Road
Over the last couple of years, I’ve increased my use of software as a service for my computing needs.  It turns out that this provides some interesting benefits when you’re on the road.  Being able to backup (and more importantly, recover) your work on the road used to be almost impossible.  You had to carry two laptops (or one laptop and two hard drives).  But if your bag was stolen or lost, you were in trouble.

My “solution” is a work in progress, as I try out different services and different behaviors.  Here are some things I do, and how I get value from them.

Taking Notes

I use Evernote instead of OneNote.  I got hooked on OneNote a couple years ago – for me, the compelling feature was good search and an intuitive organizational metaphor.  Evernote does that too – with a slightly less polished UI.  But Evernote allows you to syncronize your notes across machines.  So I can access the tool on my client-provided laptop, my personal laptop, and my desktop.  And they stay synchronized.  If I’m on the road, and my laptop dies, I can access my notes from any machine through a web browser.  After a brainstorming session, I can take a picture of the whiteboard and stick it in a note (and Evernote will index and search the text within the photo too!), and I don’t risk losing the insights from that meeting.  Oh Evernote has an iPhone client app too.  That might be the killer app for some of you.

Disaster Recovery

My off-site backup is done with Carbonite.  I pay $50/year, for unlimited off-site disaster recovery – currently at 184GB.  Using Carbonite is dead simple – I installed it, and then any directory I wanted to back up (work documents, family photos, whatever), I just right clicked and added it to Carbonite’s list of things to back up.  Every file in that directory (and every directory underneath it gets backed up).  Add more files to that directory, and they automatically get added to Carbonite’s backup.  I’m in the middle of re-ripping our CD collection for the third time now (after hard drive failures over the years).  This will be both the third and the last time.  This takes care of my primary computer at home, and happens all the time, in the background.  For $50 per year, I have a ‘never think about it’ solution – most importantly protecting our family album, personal records, and work files.  It is also highly secure (the data is encrypted before being transmitted, and is stored in encrypted format).
On-the-road disaster recovery

I am currently using subversion (and TortoiseSVN) to make archival backups of all the files I create for work while I’m on the road.  This may be too geeky for most people, but it is free for me (since I already pay for the server to host  If I finish a presentation late at night, then someone accidentally drops a piano (or a fog lifter*) on my laptop the next morning, I can still wow the client.  I have to explicitly backup each file I want to save.  It looks like you can subscribe to a hosted subversion service for $50 (and up) per year, if you don’t want to install it (for free) on your own server (various prices).

*A fog lifter is a quadruple-espresso that friends of mine used to drink to start the day (or extend the night) when they worked on-site at a client in Cupertino years ago.

Back-From-The-Road Backups

I have used Scooter Software’s Beyond Compare tool for years.  It is a file-comparison tool that is great for what it does.  When I was programming a lot, I got addicted to it.  It is also extremely good at copying files and synchronizing directories between computers.  And it can be scripted, so you can automate processes.  I use Beyond Compare to push updates from my laptop to my desktop when I return from a trip.  If subversion is a scalpel for refined work, this is my backup chainsaw, where I just keep a current copy of an entire directory structure backed up (weekly-ish) to the desktop.  And that structure is then backed up off-site by Carbonite.  This helps a bunch when moving to a new laptop, replacing a failed hard drive, or just upgrading your hardware.  I have used SyncToy too, which is also good, but seems to take a lot longer when dealing with very large sets of files.

After files are synced to my desktop (backup  #1), Carbonite backs them up offsite automatically (backup #2).  And for those urgent files while on the road, subversion is there too (backup #3).  On-site, off-site, controlled-by-me and recovery-as-a-service.  Overkill?  Maybe.


I do a lot of email.  I have personal email accounts (Google, Yahoo, and OtherInbox), I have client email accounts (MS Exchange, Google Apps, and Lotus Notes, so far), and of course Tyner Blain work email (Google Apps).  I’ve used both Thunderbird and Outlook as IMAP clients to (1) give me the ability to read and write email while offline, and (2) provide an “onsite backup” of my data that otherwise lives only in the cloud.  There’s no clear winner for me yet on the email front.  Probably Thunderbird, but frankly, I don’t spend a lot of energy worrying about “backing up in case GMail goes down.”  And when I am away from an internet connection, it makes for a nice break from email.  If I absolutely have to draft an email, it is probably for a client, so I’ll use their solution (usually Outlook).


I know most people like Google Reader.  Fine.  Keep using it.  I’ve become impressed with Omea Reader as an offline feed reader.  I like having access to the blogs I follow, even when offline.  It allows me to “surf the web” when on a plane.  When I have access online, I start with the product management river of news.  Offline, I can manage those subscriptions as a sub-folder in Omea.


I keep a 2.5″ external hard drive in my laptop bag.  It is the drive I had left-over when I upgraded my laptop drive.  I stuck it in a $12 case (hooray Frye’s!), reformatted it, and put a bunch of mp3 files (ripped from my home CD collection, sync’ed with Beyond Compare) on it, and installed winamp.  Sometimes, you just need some Velvet Revolver, Vivaldi, Erin Ivey, or Diana Krall while you work.  For travel, I have some cheap Sony earbuds for regular use, and eShure noise-isolating headphones for the flight.  Both are easy to slip in a pocket or laptop bag.


I have become truly addicted to my iPod shuffle.  But I never use it for music – I never shuffle.  I use it for listening to podcasts and audio books.  On the way out on this trip, I listened to the Tipping Point by Malcolm Gladwell.  On the way home, a Rymasoft webinar with Luke Hohmann, president of Enthiosys.  I also would rather listen to This Week in Tech (or whatever) than listen to whatever happens to be on the work-out-room tv when I’m slogging it out on the treadmill.  Also – bring a book.  For this trip, User Stories Applied, by Mike Cohn.  Sometimes, you just need the feel of a book.  Also – if you fall asleep listening to a book, you’ll never find your place again.  Much easier with a book.

That’s way too much.  The first flight was too long, I guess.  Hope some of these ideas help you make travel a little less painful or a little more enjoyable.  Any tips you want to share with folks?  Add them below.

5 thoughts on “Traveling Product Manager

  1. Thanks Kevin,

    I am growing happier with Evernote with each new release. I haven’t found myself clipping anything yet, but I love using it to take notes on a variety of topics. I even used it to capture this article while I was on the plane. Then when I got home, I synced the data, and used another machine to publish the article.

    I really like the promise of DimDim, and hope to be able to use it for more collaborative activities in the future. Today, it is already useful for “push” presentations that are 90% one-way communication.

    Also – good job, as a community manager, staying on top of your product mentions – other companies would benefit from noticing that.

  2. Scott, I have never seen a more thorough review for travel, business or pleasure. Excellent job!

    Here’s my take on a few of the topics:

    Seat Guru: I love this application! It’s most useful for international travel. I use it regularly to make sure I’m in seat I can stand for hours on end.

    Weather: I fly Delta regularly, and some time ago they started sending an email to make sure the flyer is ready. On that email they include a link to Weather Channel for the city your flying to. I’m sure other carriers do something similar.

    Feed reader: I used Omea for a long time and liked it. I ended up changing to Google Reader so I could access it from any machine. With the Offline feature you can read feeds on the plane.

    Entertainment: I’m right there with you on podcasts and ebooks. That’s the best use I’ve found for my shuffle.

    One extra: Noise-canceling headphones are a must. You have to balance socializing with your neighbor (I’ve gotten a lot of mileage from that) with keeping sane on a flight. When it’s time to stop talking, the headphones make the trip much easier. Most people use Bose; I’ve used them and love them. However, I got a pair of Jabra headphones last year (for about 1/4 the price) that work equally well.


  3. @MRH – thanks again! On weather from the airlines… American, when I checked in early, the tickets that printed out (in addition to having some ads) had weather forecasts for the destination cities.

    Noise cancellation is a huge win too. I have a pair of eShure in-ear noise isolation headphones that I replaced my old Bose set with a couple years ago. Much easier to travel with, and just as effective. They’re also really great when mowing the yard.

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