Plans Failed? Here’s Why That’s a Good Thing.

Written by on 10 Mar 2015

“I love it when a plan falls apart…”


Said no one.




Even the most free-wheeling, non-compliant, and big-picture people among us (ahem, me) still hate to see a good plan go to waste.


Most especially when they (ahem, me) had a major hand in painstakingly, deliberately, and passionately creating said plan.


In the past, I’ve written about the beauty of planning to have no plan and the surrender of going with the flow, but what on earth does one do when a well-crafted plan utterly fails?


If it weren’t for a day in South Africa two years ago, I’d still be without an answer to that question.


Thankfully for me (and hopefully for you, too!), I was able to experience a full 48 hours where nothing… and I mean absolutely nothing… went as planned. For two days, my friends and I were forced to roll with the punches, take it as it came, and otherwise maintain a superhuman amount of flexibility in order to make the best of our (bad) situation.


I hesitate to say “bad” outright, because let’s be honest—how bad can your situation really be if you’re traveling around world?


Not that “bad”.


In the moment, however, the mind often chooses to see the worst. We were only in South Africa for a couple of days. We had carefully planned out our travel in order to get the most out of short time in country. We were nervous about "missing" something.


And despite all that work, all that care, and all that planning…


We failed.




But I learned through that experience—nay, I reminded by that experience—that despite what may seem like a tragic loss when a plan doesn’t quite come together, you just never know what amazing things are waiting around the corner to take its place.


Here’s what happened:


While we were on safari, during our copious amounts of down time, several SASers and I attempted to make plans for the rest of our time in South Africa. These plans included hiking Table Mountain, a biking wine tour, shark cage-diving, touring Robben Island, seeing Simonstown (penguins!), and a handful of other excursions.


As I aluded above, we did absolutely none of this.


Seriously, not one thing.


The first morning in port was a bit of a blur. For once, I got to sit back and observe the madness that is “making-plans-the-morning-of-arrival.”


Mornings in port were an interesting phenomenon. For about an hour, everyone who was still on the ship without a definite plan would attempt to feel out everyone else’s plans, try and determine the best one, then figure out a way to, as they say, “get involved.”


Talk about FOMO.


For those who had plans, the jockeying was merely your morning entertainment. For those facing a day alone (which for some is unthinkable), it was pretty stressful.


I sat their drinking my coffee and silently applauding my well-crafted plan…


That was until I looked outside.


From the deck of the ship, we had a direct view of Table Mountain. Yes, that was pretty awesome. What was not awesome was what I saw on top of Table Mountain that morning.


On certain days, depending on the weather and other variables, a thick, dark cloud will crawl over the top of Table Mountain, rendering it “un-hike-able,” if that’s even a word.


They (unaffectionately) call it, The Table Cloth.


Plan Number One: Hiking Table Mountain


Plan Result: Utter Fail


I had some incredibly resilient friends, so we were finding a place to hike, dammit.


Next best plan?


Lionshead Mountain.


That’s right, friends, I went hiking. And I have pictures to prove it! Good ones, even!


The weather was perfect, and the company was even better. We had a great time walking around, taking pictures, being silly, and other chaos. We made some risky hiking decisions (sorry Mom!), but it was all in the name of good photos.


Turns out, Lionshead is a 360 hike, so as you climb up and down, you get a panoramic view of Cape Town.


Way better than Table Mountain.


Alternate Plan: Hiking Lionshead Mountain


Alternate Plan Result: Raging Success


Once we finished our decent, we snuck in a quick lunch at the food court on the waterfront to prepare for our afternoon plans of biking in wine country.


We made it all the way to Stellenbosch, found a cab, made it to one winery, and then…


They lowered the boom.


In the true spirit of South African plans going awry, we were informed halfway through the tour that it would be cut short due to it being Good Friday.




Apparently I missed that little rule in Confirmation.


Either way, we were bummed.


Plan Number Two: Biking Wine Tour


Plan Result: Utter Fail


Once again, resiliency was determined to have a couple adult beverages, so we just started walking.


All the places were open, so it was just a matter of finding ones that would serve us.


Three wineries later, we had racked up the following ridiculous activities, in no particular order:


  1. We trapped a wasp.
  2. We orchestrated bounce-house races (think Ninja Warrior, but different).
  3. We drank out of a two-sided, South African, traditional, wedding cup.
  4. We took over 100 pictures of the countryside.
  5. We climbed over barriers to watch the sunset on the beach.


There were probably more, but hey, wine’s a funny thing when it’s mixed with two-year-old memories.


It was, in short, one of the most memorable afternoons of the entire trip.


Alternate Plan: Self-Directed Wine Tasting


Alternate Plan Result: Raging Success


The next morning we were handed the final—and most upsetting —blow of all.


Shark cage-diving…


Was cancelled.


Honestly, y’all, there are not enough words to describe the disappointment that rippled its way through our group.


Imagine cancelling your 7-year-old niece’s trip to Disneyworld the night before…


Then magnify that by SHARK CAGE-DIVING.






So that morning, we had to find a suitable substitute for our dashed dreams.


Plan Number Three: Shark Cage-Diving


Plan Result: Utter Fail


In our shattered state, someone suggested Cape Point.


We were in no shape to argue.


Little did we know that when we were choosing a cab driver, we were choosing yet another failure.


I’ll spare you the gory details, but this man was among the most disagreeable individuals I’ve ever met.


And trust me, I’ve met some sucky people.


We spent the better part of a two-hour trip in miserably awkward silence.  Silence, people! There was no physical escape.


But thankfully, once we arrived, we realized it was all worth it.


The Cape was stunning. The weather was wonderful. And we were able to see something that only a few individuals ever have the opportunity to experience.


Suck it, shark cage-diving.


Alternate Plan: Cape Point


Alternate Plan Result: Raging Success


We made our way back in the silent-mobile, and we spent the late afternoon at a local food market on the waterfront. I was feeling a little blue because the magically experience I had expected had never materialized. I was still so caught up in what could have been, and didn’t care to acknowledge that what had been…


Had been amazing.


On the walk back to the ship, the sun began to set.


And wouldn’t you know it, God blessed our last day with one of the most beautiful sunsets I have seen to date. And let me tell you friends, when you’re living on a ship, you see A LOT OF SUNSETS. Usually, you get your ohh’s and ahh’s all ready to go, but this one…


We were speechless.


It was in that moment that I realized, things could be perfect without being perfectly planned.


In fact, it was the perfect end to a (not-so)-perfect trip.


Or at least to a not-so-perfectly executed trip.


I was reminded, yet again, that even the best plans can fall apart. And sometimes, if you’re lucky, you wouldn’t have it any other way.




Now I want to hear from you!


  1. What’s the best surprise you experienced when carefully created plans failed?
  2. Who was there with you to experience that glory?


Leave a comment below.


Leave a Reply

Your email address will not be published.

Please visit Appearance->Widgets to add your widgets here