Luck Appears When You Show Up: Notes from UA 250

Lottery UA 250

Reentering the world of long-distance travel after a month’s absence, there’s a moment that comes when I realize what it’s all about.

It’s hard to predict the precise arrival of the moment, but I never miss it.

Sometimes the moment arrives in the taxi ride to the airport, but that’s usually too early. There’s still some uncertainty at this point. The baggage in my mind takes up more weight than the bag in the back of the taxi.

Did I forget something? Do I have enough money, the right passport, the MacBook charger I keep leaving behind?

I have to know that all is well before the moment can arrive, and you can never be sure all is well until you’re at your gate and see the ground personnel preparing to begin boarding.

Sometimes the moment arrives in the terminal of my hometown airport, as I settle in at the Starbucks across from C9 and deal with as many urgent emails as I can before giving up the task and enjoying my surroundings.

Often it’s a day or two into a trip, once I’ve left America and passed through one of the many hub cities I visit several times a year: Hong Kong or Singapore, perhaps, or Abu Dhabi if I’m headed another direction.

When the moment arrives I can feel the tension in my shoulders relax. I carry this tension everywhere: there’s so much to worry about! I hope I never stop worrying. Better to worry and build than relax and let things go. There’s not enough time to let things go.

But once the moment arrives, there’s no worrying for a while. There’s only the road ahead, filled with long flights, late-night walks in big cities, and time to think.


Once we’re airborne on United 250, I review the itinerary for the current excursion. I’m not going all the way around the world this time, but it’s a respectable group of segments for a thirteen-day trip:


The itinerary is fairly normal, at least as much as mine tend to be. But I know the life I lead is abnormal, and I try to remain in grateful awareness of this fact as much as possible.

I’d never claim I built this life all by myself. I’ve had advantages and privilege and plenty of second chances.

But I also know that there were plenty of forks in the road where I made the right choice. I took a risk, chose the numbers, and my numbers came up.

You know how people wish you good luck? Next time they do, tell them that luck favors the prepared. Luck appears when you show up.

If you played the lottery over and over for an infinite number of times, sooner or later you’d win big. The problem with winning the lottery is the uncertain investment: odds are, you’d have to buy a lot of tickets to hit the jackpot. It’s a poor strategy for retirement planning.

But in the lives we lead, we can keep taking chances. We can try over and over.

You can raise your hand at any time and say, “Pick me. I’m ready.” Even better, you can step forward and say, “Hey, everyone. I’m doing this thing one way or another. Look out!”

There’s a cost to every choice, of course: the road not taken, the path not pursued. But the far greater risk is to remain paralyzed with indecision. Better to keep buying tickets in the lottery of life. Better to keep moving, selecting a new direction when one choice doesn’t work out as you’d hoped.


I’m East Coast bound today, flying to Washington, D.C. on a Star Alliance award ticket booked through United. This ticket connects to a South African Airways flight, where I’ll then begin a Round-the-World ticket the next day.

Four-and-a-half hours after takeoff, the plane descends to Dulles as I reflect on the choices I’ve made and the luck I’ve stumbled upon. I think about my next flight, fourteen hours to Johannesburg with a refueling stop in Dakar.

Changing hemispheres is always fun. On the way to the airport this morning I braced for the cold air in Portland before heading to even colder air in Washington. Then, without much effort on my part, my next outside step will be directly into the South African summer on the other side.

This is life, friends. Travel ties it together for some of us, but if you’re not on the road I hope you can feel it too.

See you next from the outside world.

Comments here.


Image: Pinelife

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    • Ragnar says:

      I think that certain edge of uncertainty can definitely be a force that makes every day feel a little more urgent. Something I definitely missed after I went back home and decided to resign to an imaginary fate. Needless to say after being introduced to people like you Chris, and others in the “perpetual travel lifestyle” community online, I’ve been inspired to take steps to make my own reality. Hopefully I’ll experience that same feeling(as in actually remember my passport) in a few months when I leave for the first leg of the journey; Thailand.

      Have fun!

    • Viv Maguire says:

      Absolutely agree, keep turning up there’s more chances of luck Enjoy your journey and thanks for turning up! Enjoy!

    • Mike says:

      Nice! I use the word “fortunate” instead of “lucky” to describe something good that happens because you showed up. I know that “fortunate” technically means the same thing as “lucky” (via the goddess Fortune), but that’s not really how we tend to use the word.

      And funnily enough, I just wrote about this just a few days ago, in fact (see the link on my name).

      It feels much better to say we’re fortunate, not lucky. We’re in charge, not the Fates.

    • Angela says:

      I couldn’t agree more. One of my all time favorite quotes is “Opportunity dances with those already on the dance floor.” (By H. Jackson Brown, Jr.) Nonetheless, it always good to be reminded!

    • Joseph Bernard says:

      Yes to keep going, keep doing and keep exploring. No to worry.

      From my perspective worry is useless. It’s a fearful and contracted response to the ego-mind. It never causes action. Too often worry can be a barrier to fully allowing the moment to guide you. Action is from finding a focus, having an intention, then creating a plan and doing it.

      Have a wonderful trip and enjoy the gifts of each moment.


    • a terrible husband... says:

      Safe travels! In my world, I’m not travelling around the world or even around the country. My challenge is at home – making sure I “show up” in every sense of the word even when it’s just the four of us. Great stuff.

    • roberto says:

      hey Chris, I run a computer business in Johannesburg. I enjoy your writing also because i have a pretty mobile lifestyle. Yet I will be in town for the next 2 1/2 months, so if you are around this neck of the woods and you want some info you can send me a mail. I am Italian but I have lived her for a long time both in Jhb and Cpt, otherwise have a great trip and yes, the harder I practice, the luckier I get 🙂 I think it was a famous golfer that said that, maybe even a South African one actually…

    • Chris says:

      Thanks, Roberto – nice to connect with you. Johannesburg is a short stop this time but I hope to return to beautiful RSA more in the future.

    • Christina says:

      “Luck appears when you show up”…love it! A great reminder to keep moving forward and taking those chances, just when I needed it!

    • Caelan says:

      ‘Fortune favors the bold.’ – Terence

      Stay brave, and keep moving. Luck will continue to follow you on your way.

    • Ryan says:

      Hey, awsome post, Chris! I share the love you have for the airport, and the flight. This article reminded me what it was like to feel the excitement and that calm joy of knowing you’ll be soon traveling at remarkable speeds to places you may never have been before, and quite far away. I’m looking forward to a trip to the Dominican Republic this spring, and this is a great mental/emotional warm-up. Thanks!

    • Pooja Dang says:

      Chris, you’ve done it again – What a fantastic post and reminder. Your book ‘The Art of Non conformity’ changed my life. As I continue to grow my life coaching practice, you continue to inspire me. Nothing left to say except YOU are AWESOME.

    • karen says:

      In the cycle of nature, there is no victory or defeat, only movement. Don’t give up. Just keep going. Moving forward. (a note I made from one of Paul Coelho’s books)

    • Rebecca Stafford says:

      Dear Chris, thanks for the timely post

      I’d like to elaborate on your suggestion that the non-conformist is in greater danger from decision-paralysis than the ‘wrong’ decision

      Fear is useful stuff and should be respected. Therefore I have evaluated my fears (aka night terrors) around my business launch. My report informed me that my main reasons for not going ahead with my business plans relate to fears of being criticised as not being good enough.

      My fears are normal – as in a common response to putting your work out in the public arena – but they are not USEFUL to me.

      Fortunately I have realised that there is something SO much more terrifying than people thinking or telling me that my work is crap

      -and that is being at the end of my life and realising that the only reason I didn’t publish work that was so important to me, and had the potential to help many people, is that I am scared of the opinions of people who don’t matter.

      No, I’ll be looking back and thinking, “Yeah, that terrified the hell out of me and I did it!”

      I still feel anxiety in relation to my business launch, but less frequently and less severely.

    • Jacqui says:

      I hear you! A few of my favourite words I have read in the past:
      – Luck: where preparedness meets opportunity.
      – Even if you are on the right track you will get run over if you just sit there.
      – To turn a ship it needs to be moving.

      I know that some people have thought I have been lucky but they have absolutely no idea of the work that has gone on behind the scenes to bring me to that point. That’s ok, and I want to keep on creating more luck! 🙂

      Enjoy your tip Chris.

    • Elan says:

      Thank you for your post Chris. A short 3 months ago I first watched you on your ‘Becoming a Travel Hacker’ course on Creative Live. I bought that course and studied it. I remember being excited to see that you were starting your Round the World ticket in January from Johannesburg – my home town! ‘Luckily’ I took heed of your advice and have begun implementing your strategies. In the past week I’ve booked 6 tickets for myself and my family all through points we’ve earned in just 3 months of travel hacking. A huge achievement considering I live in a place where we don’t get massive credit card sign up bonuses like the US. Luck to me is when preparedness and opportunity meet. Thank you once again.

    • Kabamba says:

      “This is life, friends.”
      Absolutely loved that 🙂

    • Alexander Dziri says:

      Love the lifestyle you’re leading Chris, enjoy your travels!

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