Our family’s global migration to a new boat made me wonder: Why do some things work out so smoothly and easily, and other things are so difficult and tough?

After all, our first trip from Tahiti to California (which should be easy) was so crazy difficult; and then the next 3 legs across the world to the Seychelles (which should be super tough) was actually piece of cake.

What gives? Why are we in flow sometimes; and totally not other times? Is it luck of the draw, alignment of the stars, or some sort of skill/mindset??

An insight from my brother Dylan helped me understand this. 

He recently shared this at a career presentation for high school students. Referring to landing a job, he said, “Luck is opportunity plus preparation. You can control your own preparation. You can’t control opportunity, but you can be ready for it. When both happen, you get luck.”

Interesting. To explore this idea, I gave aspects of our trips a grade out of 10. This helped me get a grasp on why we had poor luck on one trip, and such great luck on another.

Here’s how I thought about our two very different experiences:

During our Tahiti-SF leg we had POOR LUCK! Normally an easy, direct 8hr flight. But was extremely tough! Read more about this crazy trip in our last post.

• 6/10 for preparation. We failed to identify some mission-critical things.
  • We THOUGHT we prepared well.  We spent weeks planning the bags, weighing them multiple times to ensure they were below the 23lb / 50lb thresholds;
  • we coordinated a taxi, van, huge tahitian guy to help, and managed to get everything to the airport.
  • BUT — we got the wrong carry on bags, slightly large, which caused absurd problems.
  • And most importantly we didn’t double check Zoe’s visa requirements for USA, which was mission-critical. BIG error.
• 2/10 for opportunity. The stars were not aligned.
  • I mean come on. The French Bee check in people were unfriendly, sticklers for rules beyond the call of reason.
  • Zoe got her travel authorization for USA (aka the ETSA) just 45 seconds after the check in desk closed. Just not fair.

In constrast… our next part of the voyage was completely different.

For the SF-Seychelles leg we had AMAZING LUCK. This was a gigantic trip of 30hrs with 2 stops, with 18 bags, and 2 toddlers. So much could go wrong. Yet it went super smooth and easy. And incredibly full of serendipity!

• 9.5/10 for preparation. I have to admit, we were READY.
  • We tried to nail every detail possible, and learn from our mistakes on the last trip. First off, we got 4 Samsonite carry on bags from FB marketplace at to replace our crappy carry ons that gave us so much grief with the airlines last time (being slightly “too big”)
  • We bought seat extenders for the girls to get better sleep — they worked remarkably well! Worth their weight in gold for sleeping. Check an example.
  • We did the Travel Authorizations for Seychelles a week in advance, paying extra for their premium support (since we’re sailing out of the country, it’s way more complicated).
  • We had 3 cars driving us to the SF airport, and 2 vans picking us upon arrival in Seychelles.
  • It wasn’t 10/10 because our bags weren’t perfectly packed, there were several bags a few pounds over which we had to shuffle last minute at the ticket counter. Luckily opportunity was on our side (see below). And we could have planned our lounge access for Dubai better.
• 10/10 for opportunity. The stars were aligned, there is no question.
  • A storm had battered SF the day before, the so-called atmospheric river, grounding dozens of flights. Lots of traffic lights were broken that morning, and we even saw a car crash real time as we drove to the airport. Thankfully we relayed this to all 3 cars, and we made it safely to the airport. Ufa!
  • Our United check in lady was from the South Pacific, and she was SUPER kind and helped us navigate bags costs to save hundreds of dollars. With 13 checked bags, 3 adults and 2 kids, this took a full hour.
  • Just after security, when we start struggling with our huge load (they take away luggage carts at security), our friend Tracy, an airline stewardess, showed up to help! Unbelievably helpful.
  • I stopped at a lounge to get a cappuccino for Sabrina, and ran into one our NICU nurses from our girls’ birth at UCSF. Definitely random!
  • The first flight to NY was completely full and they asked for volunteers to check in carry-on bags. We happily consented as they promised to send them all the way to Seychelles. So we had 3 less bags to deal with, we were so happy! During this time, the United gate agent was incredibly friendly and helpful; so it wasn’t just our South Pacific lady that made service a priority.
  • While at our gate in San Francisco, Sabrina ran into an Australian friend of hers from when she used to work at Mountain Camp – he was on our same flight from SF to NY. More serendipity.
  • Our NY flight was quite late, we had to run to the next flight for Dubai, but since we had checked in those extra bags, we made good time and made the flight. Ufa.
  • The passenger seated behind us on our Dubai flight saw us arrive with our kids and arsenal of bags, and promptly asked the flight attendant to be moved further away to another seat. The twins are like cavalry, scaring off anyone in their way haha! The result is we got 2 rows to stretch out, which was glorious! (Nice work girls!)
  • Upon arrival in Dubai the United pilots let the kids visit the cockpit and sit in their seats! The twins were star struck and thrilled 🙂
  • Dubai Airport was easy — they had a Lego Store! enough said! We spent our 7 hr layover between two lounges, courtesy of our credit card Priority Passes (we’ve been working on that for awhile, it is very helpful for sanity)
  • The Emirates flight was very delayed on the tarmac, but the sweet stewardesses fell in love with the twins and took multiple souvenir Polaroids of them for us. Emirates took it to the next level.
  • Arriving in Seychelles, our boat manager Vincent picked us up, he moved our boat to an easier loading spot, and everything was super smooth for the arrival at our fancy new home!

As I think about opportunity vs. preparation….

Opportunity comes in its own time. There’s ways that people try to tune into this — astrology, I Ching, intuition. Although opportunity is mostly* driven by forces beyond our control, we can be ready when it shows up. How? By being present and having good energy.

There is no question, good energy prepares us for opportunity. Case in point, going to the great show by Miles Jay and his dad the night before my flight gave me a boost of energy, even though I was feeling rundown and going out late would normally be the last thing on my mind.

As a result, I started the trip tired, but stoked. You know what I mean? Fairly low energy (tired), but great energy (positive). Our language doesn’t have enough words for the nuances of energy. We need to invent some more.

*I said “mostly driven by forces outside our control”, because although a lot of opportunity appears random, I believe there is actually a lot of opportunity that is based on the foundations we’ve laid in the past — such as good conversations with random people, cultivating relationships with loved ones, having integrity in all our affairs, etc.

Preparation is within our control, but WHAT we prepare is the true art. After all, do we prepare what is mission-critical — or just the huge number of non essential details?  This is a big take away from Seamanship, our success as sailors. The challenge is that we can put way too much time into some systems, but overlook critical systems. This is understandable, because often they are hidden.

Many travelers spend way too much time preparing for a trip by trying to control every possible outcome — what hotels they will stay, what tours they’ll go on every exact day.  But the reality is we can’t control the outcomes, we can only control our preparation, our ability to adapt quickly as changes demand.

Hence those are my two take aways for good preparation: 1) do what is mission critical, even if it’s invisible; and 2) prepare extensively so we can adapt quickly, not control every outcome. 3) raise your energy so you’re positive & stoked. With these ingredients I find I’m better able to stay open to different possibilities is where the pockets of serendipity arise .

The final goal? Staying centered and having fun.

To paraphrase Franklin Roosevelt, “There is no planning, only preparation.” Things don’t usually go according to plan ; but planning is critical so that we are prepared for anything.

And as Forest Gump reminded us, “Sh*t Happens”. The stars don’t always align. Opportunity comes and goes. All we can do is get ready!

Thinking about preparation and opportunity helps us maintain equanimity: the ability to stay centered in any situation. And this makes everything a lot more fun. Especially when the stars align 🙂