For two years before we took off on our one year journey, that has turned into seven, we were actively planning. You know, the checklist type of planning.

You might not know this about me, but I’m a pretty focused and organized person. I am great at taking a giant, impossible seeming task, breaking it down into it’s component parts, and making things happen. We decided, on a Sunday afternoon drive, that we would fold up our static life and take our kids on a grand adventure. That very afternoon we set our launch date: April 1, 2008. Two weeks later I had a binder in my kitchen full of the detailed plan from zero to launch that would take 23 months to complete. We hit the ground running.

There are lots of ways to prepare for a RTW trip.

I know people who’ve made the decision to leave and within a month, they’re gone. Poof. They dropped it all like a hot rock and just took the plunge. I admire that, and it simultaneously terrifies me. I’m far from saying that “my” way is “the” way, or even a better way than simply diving in. The argument could be made that we “wasted” two years that we could have spent on a beach somewhere. I get that.

The thing is that I think most people fall more in my direction, the direction that tends to worrying about minutia, planning extensively, and trying their level best to make “responsible” decisions and prepare “properly” for any big life change.

This question, from a reader, got me thinking about it:

I remember coming down to “the one month before launch” moment and hyperventilating. In spite of my binder and 22 months worth of four week calendars, each with its own checklist, covering everything from gear selection, physical training, test trips, the education of the children, saving, quitting a job, remodeling a house to prepare it for sale, skills acquisition, healthcare and immunizations, to route planning, destination research, and language learning. I attempted to learn Arabic, in addition to polishing my fluency in French and Spanish. The Arabic did not go well. We could not possibly have been better prepared. We’d left nothing (and I do mean nothing) to chance. We were responsible parents of four, we carried that mantle with sacred reverence. We would not drop the ball. We’d done everything right. And we were terrified.

I can count the nights I slept through, in that final month, on one hand. I burned the candle at both ends. I made lists on top of my lists. I looked at my little children, who were eagerly counting down the double digit days with stickers on the fridge (they’d been adding a sticker a day since the “400 days to launch!” mark) and I prayed that I’d done enough. That we hadn’t missed something glaring and obvious and potentially tragic.

The day we departed was a banner day for our family. The joy and justified satisfaction in lifting off, knowing that you’ve done your level best and earned every single bit of the victory is a singular experience. The absolutely gut wrenching, terrifying feeling of free-fall that comes with closing the door on everything you know and opening the door to everything you don’t is also unparalleled. And I think the reader is right, it is even more so for families. We parents are freakish about giving our kids the very best of what we can, and there is a prodigious amount of second guessing inherent in any outside the box move a family makes.

At the time, I couldn’t see it any other way than from where I stood. I couldn’t imagine the “irresponsibility” of launching any other way. I had to, for my own sanity, for my own psychological health, dot every i and cross every t. I just had to. If I hadn’t, and something had gone awry, I would not have been able to live with myself. Making my best effort at covering all of the bases abroad, just like I do at home, was crucial to my ability to loose the bow lines and set my little family adrift in the world.

Of course from where I sit now, the landscape looks entirely different. Now, taking the leap, plunging into pick-an-unknown in the world, and living outside of our comfort zone has actually become our comfort zone. That’s weird, isn’t it? Now I know that a good 80% of what I planned contingencies for was unnecessary. At least 75% all of the route planning and destination research I did went unused. Even better, a good 98% of my late night worry sessions over the many, terrifying, worst case scenarios that could have ensued were a senseless loss of sleep over nothing. It turns out that the worst case almost never happens, and the world is, by and large, a lovely and safe place to raise kids.

If I could time travel back to 2006 or 2007 and sit myself down with that big binder and a cup of tea, I would tell myself a few important things:

We all make the very best of what we have, at home, or abroad, and all of the determination and problem solving and energetic effort to make sure life runs smoothly goes with you when you take off. You’ll be leaving behind your stuff, but not your resourcefulness.

There will be hard things, you’re going to lose every penny you’ve saved for this trip in about 8 months… that’s going to suck… but it’s also going to be the catalyst for the most important, best choices you’ll ever make in your life. I’d spike my own tea with a stiff shot of bourbon, listen patiently to all of my, “But… but, but… what if…” worries, and then I’d insist that my former self calm the heck down.

Show me the mother who does not quietly obsess about this; I don’t believe she exists. In my favor is the fact that I, myself, was road-schooled for a couple of years, and I know, from the kid’s perspective, that those were the best two years of my educational career.

What I learned was unparalleled, and my book learnin’ didn’t suffer either. I’ve always known, first hand, the gifts of an outside the box childhood. If I could go back and show myself clips of my kids now, at 13-19, my young mama self would have wept with relief, and disbelief, and gratefulness.

I could never have imagined what a great teacher the world would be or the doors that she would open for my young people. There is no question that they are different people for having had the experiences they’ve had. Of all the worries I harbored in my mama heart, not a one turns out to have been founded. It would have been a relief to have been able to see that up front.

The type A personality in me laments the fact that I would have packed and prepared very differently if I’d known we’d be on the move for most of a decade, instead of the year we planned for. I probably wouldn’t have been able to hear myself at that point, as I was so focused on my lists.

I’d love to be able to play back the reels and show myself the highlights and the pivotal moments. Even when we’ve come back, for periods of time, we aren’t really “back.” Of course I knew, before we left, that it would change our world, but I don’t think anyone really knows just how profoundly a good long walk in the world affects the layers of who we are. It’s not about whether we bodily return, it’s about the impossibility of returning intellectually, socially, emotionally, or psychologically to the place that we began.

I’d probably need to pour my earlier self another drink to deliver this message. I so enjoy planning and controlling the variables. I’m not a big fan of surprises. I couldn’t imagine then that both of our careers would change in addition to our approach to family life, building community, and the logistics of how we live life and plan for the future. I think I’d have been excited to know that it would all work out, in the end, but it also would have given me more things to lay awake worrying through and dreading. Maybe I’d only tell myself half of the truth on this point, out of kindness.

So what’s my advice to the guy who’s down to the wire and sweating his big launch, wondering what he’s missed?

The earlier me, who’s still under the hood here somewhere, would congratulate him on preparing to the best of his ability, it’s always important to do our best. The road weathered me would smile, offer to buy him a drink, listen to his worries, and look hard for any obvious holes in his plans. Sometimes we do miss something that matters, talking to people who’ve done what we want to occasionally helps!

Then, I’d smile at him, and I’d start telling him stories. I wouldn’t tell him what I’d go back and tell myself. He’s not me; he wouldn’t listen. Instead, I’d tell him stories about beautiful people and exotic places.

• I’d tell him about how living in Tunisia made my kids different, and how Guatemala has gotten under our skins.
• I’d let him see my eyes tear up as I remembered hearing my Dad tell the boys ghost stories of his younger adventures in Africa as we fell asleep on the Sahara, on Christmas Eve.
• I’d let him see the joy I have in having given my children camels for Christmas, elephants, Angkor Wat, New Zealand brown trout, train rides, and Ho Chi Minh for birthday presents.
• I’d blow him away with the spookiness of night diving with sharks on the Great Barrier Reef for Halloween.
• I’d let him hear my kids chatter excitedly through their list of “best and worst” and argue about the finer points of what it’s like to live under various political structures.

I’d pour him a drink, we’d sit on the porch of my yellow cottage on my favorite lago and I’d do my best to tip the scale of “worries” to “worth it.”

If you’re knee deep in trip planning, what are your biggest concerns? If you’re experienced with planning this type of adventure, what advice do you offer to first-timers? Tweet us @bootsnall, or me, personally, @edventuremama