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#3 Pirates, Cowboys, and the open road

  • Writer: Christian D'Andre
    Christian D'Andre
  • Jun 17, 2024
  • 6 min read

Updated: Feb 14

I’ll be honest: I just had a bunch of ideas flood my brain like a tidal wave, and I’m going to try to connect them all. Lately, I have been reading a book by John Eldridge called “fathered by God. It’s a book about the stages of the masculine journey, and how God is a part of each of them, guiding us along the way. To make a long story short, he talks about a “cowboy phase,” in which he describes the young boy as someone who wants to get out there, drive on the open road, go out on adventures and ultimately test the limits of his own capabilities.


Although I had never had a particularly strong thing for cowboys, using the metaphor of a cowboy was working for me and his analogy was making sense for the most part. But then I had a mega-click moment. I realized that his description of cowboys almost matched the attachment I had grown to pirates: taking off into new territory, facing perilous adventure, acting a bit reckless from time to time. Oh, how I fell in love with the world of pirates because it described so perfectly the story of my life. Except, I hated this life of adventure that I had been sucked into. All the traveling, new places, different foods and hiccups along the way. It all made me sad. Nothing ever stayed the same! Nothing ever slowed down long enough for me to really capture it, to take hold of it, to understand it. Every time I would feel like I was getting the hang of things, everything would up and change again! It sucked!


However, if I could pretend to be a pirate, I could embrace the whole adventurous lifestyle. Though it still wasn’t quite me, it was at least something to get excited about. I kept asking myself: what would I be known for? What would be the one personal item that I would take with me if I were a pirate? Would I be the musician, bringing my guitar with me everywhere I went? Would I be the entertainer, needing nothing but my vibrant charisma to keep spirits high? Perhaps I would be known as the greatest fighter on deck. The ideas were endless, and I still sometimes draw upon this story to help me travel. 


But what then, does this have to do with toughness? Well, sometimes this is how life feels, isn’t it? Think about life on the high seas. It can be treacherous, no doubt! Not only is there the risk of drowning if you go too far from your ship and crew, but there are also storms that toss the boat about like a fresh caesar salad. I haven’t done a ton of sailing in my lifetime, but based on what I have gathered, it seems as though it would be like riding a bull! And I’m sure those storms don’t just wait until the middle of the morning, when the sun would be too hot anyway and the crew are already up and awake. 

NO!


Storms strike whenever they like! It is you who must be ready for it! You must be ready when the waves come knocking! With an “all hands on deck!” You must scurry, rushing to the nearest mast to hoist up the sails and batten down the hatches! It might be two in the morning or two in the afternoon. It doesn’t matter. Up you must go! Because choosing not to might mean choosing to drown! Does this still sound like the type of life you want to live?I mean, I feel like I already live this way sometimes. Although I’m not waking up at 2am to the splashing of the salty ocean spray, I did have my car break down on a Sunday afternoon when I was planning on relaxing. Is there that big a difference? Don’t we all live a sort of pirate-life? I don’t think that’s such a stretch to say. But then my heart burns with the question: can we learn to embrace the struggle? Can we learn to make something out of our messes when they arise, or is the silliness of the pirate story just part of the myth? I have a few takeaways, but I want to tie this back to our theme by asking this: what can we fall deeper in love with to help embrace the struggle? 


A pirate’s great love is his freedom. The ability to parade around the open seas with no one telling him what to do or who to be. He is truly a free man indeed. Every day on the open ocean is another day he has earned his right to be alive, and live in any manner he so pleases. Many a day, a pirate says to himself “that was quite the snag. I ought to be dead! And yet, I’m not!” How often do we rejoice over the trouble we narrowly avoided? How often do we truly embrace what we have salvaged? I’d venture to say not often enough. Let me give you a personal example.


Last weekend, I was nearing my wit’s end. I was exhausted, so I went to my oasis: the movie theater. I made it over and saw my movie like I always do. It was a normal day. But when I stepped back into my car, I saw that dreaded “check engine” light come on, and I felt my blessed vessel get a bad case of the hiccups. I managed to get her home and called a buddy to come help me figure out what was going on. And as he was driving across town to come to my rescue, I was fuming.


“How stupid is this! And on my precious Sunday, no less! I had all these plans, things I was going to get done! And now I’m stuck with the stupid car!” I thought to myself. Eventually we got it all figured out and we felt better, but as I am fleshing out this idea, I can’t help but wonder: is there a way I could have embraced this mess? I mean, sure, no one wants to have problems with the car or have their sunday interrupted, but isn’t there some way to keep this from becoming an absolute disaster? Could I deepen a love of something to help overcome my struggles such as this one? 


First of all, why do I get so focused on my love for what I had? I get so focused on what it cost me to fix the car, the time it took me to go to the dentist, and so on. I make a martyr of myself over all the useless crap that I have lost! What about the things I have gained? The car that’s up and running again? The teeth that no longer ache? Did I forget all the good that has come from my so-called “loss?” But even beyond that, try to stop and imagine how much worse things could have been! That stomach ache could have been your appendix. The rain could have turned into flooding. It could always be worse, and we need to start focusing on what we managed to salvage from the storm, instead of what we lost. 


And deeper still, don’t we value our lives? Our freedoms? We have started acting like certain things are to be expected, rather than gifts we are fortunate to have. And I’m not saying this to try to condemn, I forget this on my own worse days as well. I sometimes forget that I once had to work seven days a week just to pay the bills. I conveniently get amnesia, neglecting the times when the days of the week would blur together, losing their meaning altogether. I forget my own storms when the waves die down. And as such, I lose my gratitude for the sun shining down on me. 


And it’s so strange to me: we don’t want the storms to come, but it almost seems as though we’re miserable without them! The sun becomes less of a blessing, and more of an expectation. Here’s an idea: what if we turned the tides, and expected hardship to come whenever, and treated our blessings as something rare. I think our lives would be a whole lot better if we woke up excited that we didn’t get scurvy, than disappointed that we have to get the oil changed in our car (and with the way I eat, maybe I should have scurvy. Arr!) 


What if we jumped to when life’s storms hit, embraced what we managed to salvage, and rejoiced over the fact that we narrowly escaped drowning? What if we accepted the idea that life is full of storms, rough waves, and the occasional salty slap to the face? What if we, like the pirates in the movies, learned to fall in love with living, instead of neglecting it like we so often do? Is falling in love with life itself deep enough to overcome a few storms? I’m inclined to think so. But let me know what you think in the comments. Drop your email down below if you like my content, and until next time:

May Peace be your guide.


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