Wing It Or Plan It: How Do You Go Through Life?

“He who every morning plans the transactions of that day and follows that plan carries a thread that will guide him through the labyrinth of the most busy life.” –Victor Hugo

“The problem with a plan is that you fill up the blank page of a new day with a ‘to-do’ list before you get there. And if you’re not careful there’s no room for anything else.” –John C. Parkin

Hello friend,

I am caught in an existential crisis at the moment. My head is trying to convince my heart that it would be better off if I would just go against my nature for the short-term. And even though I can see the logic in it, my spirit translates that logic as clipping my wings and putting me in a cage. Thus, the spirit is railing against “the rules” of the brain with all its might, fighting for its freedom as though its very life is being choked out. I cannot be contained!

I am leading my family on a big adventure to the mountains in a few weeks, complete with camping, sightseeing, special adrenaline-rushing excursions, and lots of restorative communion with Mother Earth and The Man In The Moon. I have been looking forward to this trip for what feels like forever, and I could not be more excited to get out there under the big sky and “sound my barbaric YAWP over the rooftops of the world,” as Walt Whitman once wrote.

I say I am “leading” not just because I have been out to the mountains before and feel at home in the outdoors, but mostly because my wife has given me complete responsibility for the planning and execution of this giant trip. Argh!

Other than the implicit pressure that comes with that responsibility–basically, “Make sure we all love it!”–I was initially enjoying the job as trip coordinator. I got to pour over maps–a favorite pastime of mine– to plan a general route that would cover a mix of my favorite memories from past trips and also some fun new stuff–like zip lining in the canyons and whitewater rafting–that will make precious new memories for all of us. There was a general vision in my head, but plenty of fluidity to allow for whims and spontaneity. We have a tent, and I was busy accumulating the other camping accoutrement. And the last time I was out there–just a couple of wee decades ago–there seemed to be campsites everywhere I turned. I figured that was about all there was to the coordinator job. Planning complete! Now back to the daydreaming…

Oh, if only it were that simple.

I had to go and start talking to people about it! From my siblings and friends, I was looking for insider travel tips for the national parks, camping suggestions, hidden gems, cautionary tales, and, as always, great personal stories of how the land and the adventure have affected them.

I started with my siblings, one of whom lives out there and two who have traveled extensively in the area. We met up recently for a leisurely family vacation, and the topic of this adventure was infused into nearly all of our conversations from the beginning. Far from confirming my happy memories and fantasies of open campgrounds and quiet trails in the forests–communing with Nature in blissful solitude–all I got were horror stories of how crowded the parks have become, what a nightmare it is to find campsites anywhere that haven’t been reserved (requiring multiple back-up plans), and how exorbitant nearby hotel prices are.

Instantly, I could feel knots growing in the back of my shoulders and the pit of my stomach. Stress. Dread. Despondence. This was not at all what I was expecting from the conversations, and definitely not the feelings I wanted to associate with my beautiful fantasy of a trip. And I was on vacation when all this came up! I didn’t want the feelings then, either!

I tried to let them slide by me: “Oh, I suppose I have a bit of research ahead of me when I get back home next week. No big deal.” But inside, I could feel the awful churning and the knots. These were not going to allow themselves to be stifled. Because I know myself quite well after all of these years with my journal, and I was absolutely certain of two things that would ruin a day–or many–on my dream adventure: 1) chasing around in vain all day trying to find a place to spend the night instead of exploring the natural wonders (and even the prospect of chasing around the next day), and 2) getting stuck without a place and being forced to spend an exorbitant amount of money on a high-season tourist hotel in some town away from where I really want to be. I am not willing to accept either of those options on this trip; it means too much to me. Hence, the churning and the knots.

They kept building and building for a few days as I labored at denial. At last, they got the best of me. While my children, siblings, and extended family frolicked in the laziness of a day at the lake, I closed the door to my bedroom and bunkered down with my books, maps, phone, and tablet. I needed to make some reservations.

Yuck! Even that word makes me feel constrained: RESERVATIONS. Maybe it is a silly class thing: I don’t want to be associated with something fancy enough to require “reservations” for me to get in or to keep other people out. Maybe it triggers my dislike of crowds and feeling cramped: if you need “reservations,” there must be limited space (and I hate limited space). And maybe it is just my natural distaste for the tedium of research and planning: I just want to be there and flow with it.

I see as I write this that the last one is a loaded issue for me. I do not appreciate the grinding of details and numbers and other minutiae that remove me from the experience of the thing. I want to be in Montana; I don’t want to plan the budget and research and book the hotels and campgrounds and excursions and plot the exact movements of the days so I can be in Montana. I just want to be there! The details only serve to annoy me.

I chide myself for this petulance, as I know it reveals the spoiled child aspect of my personality. I want things to be easy for me. I get irritated when I have to be bogged down with the details rather than the big picture, or if I have to labor too much to get what I want. It is the same stuff that I lecture my children about. But I am a middle-aged man! My frustrations reveal the part of me that has yet to grow up. It’s a little embarrassing.

On the other hand, I am trying to become more accepting of myself and allowing space for my imperfections. I get that I am a little bit spoiled. I get that Life is a challenge and things like making ends meet and getting to do all the things you want to do is not the norm, but I still expect that for my world. I have always had people in my life that have been sympathetic to my cause and have filled in the gaps of my personality quirks, most especially my parents and my wife.

My wife–bless her heart–does all the stuff at home that my mind (well, let’s be honest: every fiber of my being) rejects. She fills out forms and deals with insurance companies. She does product reviews and full-scale research for every major (and most minor) purchase. She looks at bank statements and retirement documents. She books airline tickets and knows the password for Amazon. She even talks to the cable company! All things that make me want to shut down and hide in a cave. It is why this trip-planning experience has proven to be such an odyssey of travails for me. All of this is her element and her role in the relationship. I am completely out of my water! It is quite pathetic, actually, because of course I understand that regular people do this stuff every day. My stress and the fears that my soul will be crushed under the weight of the planning are silly, no doubt, but I still feel them. (Thank God I live with a grown-up!)

I once heard discipline defined as “freedom within the form.” That idea has always stuck with me. Freedom within the form. It seeps into my mind now as I try to make sense of my predicament. It strikes me that what I need for this trip is not so much complete freedom but rather this freedom within the form. I need discipline. The only way I can feel free to wander freely along the streams and sit by the campfire gazing peacefully at the enormous night sky is to have all these reservations in place ahead of time. The only real constraint is knowing I have to be in certain campsites or hotel rooms each night of the trip. These are the milestones. What I do in between those nights–which mountains I climb or rivers I cross or roads I travel–is left to the stirrings of my soul. When I look at it like that, it is so much more palatable. Sure, I still have to go through this torture of research and reservations and holding myself to a plan in order to gain that disciplined version of freedom, but I suppose that is the price of the ticket to this show. Sometimes you just have to pay it (or so I keep telling myself).

I am addicted to Freedom and will always desire that ability to run wild and to wander without limits. I won’t ever stop preferring to trust in the Universe to provide and simply winging it. I will always want a big, wide-open space that is safe to play in so I can just do my thing. I suppose that in grown-up life, what makes the safe playground is plenty of money, things like health coverage and a low crime rate, and some well-made plans. Unless I can get someone else to provide all of that for me–“Anyone? Anyone? Bueller?”–I better get used to earning my freedom by working to create a big enough and safe enough form to play in. I may never become a happy planner–it is probably just not in the DNA–but I hope I can find the wisdom to summon that little bit of discipline that will make me a much happier camper. Yeah, I think I’ll plan for that!

How about you? Do you prefer to plan things out or fly by the seat of your pants? Open up your journal and process your preparations for some of your bigger life events and adventures. When it comes to the big stuff–trips, weddings, work events–do you like being the planner or just showing up and going with the flow? Does planning too many details or every minute of the day excite you or take the fun out of it for you? Which gives you more self-confidence: going into a situation knowing you have a plan, or coming out of a situation just fine despite entering without a plan? Do you tend to worry if you don’t know what is coming next? On a scale of 1-10, how spontaneous are you? What is the biggest thing you have ever just winged? How well did it work out? What did that teach you about yourself? What do you think about that idea of discipline as “freedom within the form”? Is that something like a middle ground between being an obsessive planner and a freewheeling floater? Does it work for you to lay down milestones–like me figuring out where we are going to sleep each night–and then give yourself freedom to do what you want between those markers? Does it give you more stress to plan hard or to be without a plan? How much can you plan for your next adventure before it becomes too planned? Where is that line for you? Are you the same way in your regular life as you are with special events? Are you good with the grind and details of things like monthly bills, insurance, taxes, retirement planning, subscriptions, and the like, or does that stuff feel like a completely different planet to you (as it does for me)? Do you feel like you need a “real adult” around to keep your life in order so that you can be “free” and wing it? Are you that adult for someone else? If so, do you hold it against them or just accept that we all have different strengths? Do life partnerships work better when there is one planner and one winger? Do you keep a real schedule that you access regularly? Do you appreciate its convenience or resent it for running your life? Whichever way you feel, do you think the plan is necessary for some degree of peace of mind? How has your planner vs. winger dynamic evolved as you have moved through life? Which way do you tend to be evolving toward in the long-term? Does that feel right to you? Leave me a reply and let me know: Do you plan your way through life or just show up and roll with it?

Gulp down every moment,

William

P.S. If today’s topic resonated with you, please share it and grow our web of contemplative beings.

P.P.S. If this way of questioning yourself invigorates you, consider buying my book Journal of YOU: Uncovering The Beauty That Is Your Truth at your favorite online retailer.

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