Road Trip to Yesville

This was written by my friend and fellow adventurer Joe O’Leary, the Wiser Amuser (

Says The Wiser Amuser:
Practice being selfless
without being yourself less.

Among the many things I love about planning a road trip is that “spending quality time alone or with someone” is always the plan and when your road trip is done and everything went according to plan, as it always does, you realize the quality time you spent had as much to do with what wasn’t planned as what was. Know what I mean?

Hence, the beauty of living in Colorado, where a lifetime of quality-time road trips abound profound.

“So no s#!t, there I was…knee-deep in hand grenade pins and out of bullets…”

It was 7:30 pm in Silverthorne, Colorado, three days before New Year’s Eve and just 90 minutes into a four-day road trip to Aspen with my sons, Kai (10) and Tragar (6). We hadn’t eaten dinner yet and I was hungry, but they were exercising their newly acquired super hero power. They asked for ice cream before dinner, and I’d said yes.

The temperature gauge inside my truck read 19 degrees, but as I stood uncomfortably at the Dairy Queen counter, things were heating up.

“How would you like your Blizzard?” asked the DQ clerk to Tragar (6), who turned to me, barely containing his excitement. “Whatever I want, right, Dad?”


He turned back to the clerk. “Okay…I want strawberries, raspberries, and Reece’s Peanut Butter Cup…in chocolate and vanilla swirl ice cream…with caramel, cherry-dip, and hot fudge…mixed in…please.”

With half a grin and two raised eyebrows, the clerk turned to me with a sort of amused curiosity. I smiled and nodded, yes.

“Dude, nice!” she said as she extended her fist to Tragar, which he met with a solid bump. “Anything for you?” she asked me.

“Yes, I’ll have the same.” And bump-bump went the fist-bumps all around into skyward-spraying fireworks – ZAP! ZOWEY! BIF! KAPOW!

I’m not sure which came first, my tendency toward self-inquiry and growth or my curiosity for the outside world, but I’m certain that neither would have evolved so openly or deeply or darkly or brightly without the other. And both are responsible for my sometimes-foolish love for a good road trip.

I could wax long-winded of road trip memories, from early childhood through high school and college right up to present day, but the point would be that I’m simply nuts about the quality time inherent in a road trip and the only proven remedy for my nuttiness has always been to have another one on the calendar. I’ve recently learned, however, that if my kids are along for the ride, there is a certain super hero power that goes a long way for making quality time happen.

The aforementioned road trip to Aspen had been on the calendar for a couple of months and my excitement to share a great bonding adventure with my sons only grew each day it approached. On the morning of our departure, however, I met an unexpected foe: impassioned resistance. As soon as I started the conversation about what we needed to do during the day to prepare for the trip, I realized suddenly that the only kind of bonding adventure my sons would entertain required electronic screens and Legos. The dark side of Christmas was upon me. I tried every form of logic and reason to help them see the greatness of my plan, but it fell on defiant ears.

In an instant I’d gone from Super Dad (in my own mind) to Super Villain (in theirs).

Says The Wiser Amuser:
To expand and grow your content.
To bolster your resolve.
To plant the seeds of intent.
To force you to evolve.
You might not like it now,
you might not feel its lift,
but time reveals the silent vow
in failure’s timeless gift.

For the rest of the day I rode a pendulum of confusion between my sons’ wails of protest –

How far is the drive? Four hours? Do you know how cold it is outside? What do you mean we can’t build Legos in the car? But he is so annoying. But he’ll hog the radio. They’re your friends not ours, Dad. Why do we always have to do what you want to do?

– and my own internal conflict –

How is it possible that they don’t just get excited when they hear the words ‘road trip?’ What if I can’t convince them to go? Or what if I do convince them to go and we have a miserable time? That would be worse. We are due for quality-time. I am NOT going to spend the next four days at home battling a mountain of Christmas presents preceding my presence. This is not part of the plan…

The whole point of this road trip with them was to connect and plant positive memories, but negatively-charged resignation was all I’d accomplished so far. How could I ensure a positive experience?

I’d struggled with that question all day until, in the final hour before our departure, I recalled a conversation I’d recently had with another dad who’d taken his 8-year old son to Mexico for three weeks. What stuck with me about his description of their trip was that he could not recall saying no. Not once in three whole weeks. They simply agreed on things and everything just flowed, he said. While he acknowledged, for my sake, that such a scenario is much simpler with only one child in tow, I just couldn’t shake the wonderment of everything just flowed.

That is the kind of greatness I wanted for our trip, I thought, but how can I get through the next four days safely and responsibly without having to tell my boys no? It wasn’t until I finished loading the truck and the boys were angrily buckling in that the idea hit me.

Before starting the engine I turned to them and said, “Guys, for the next four days, I will only say yes to you. I will not tell you no.” I paused to let the message register with them…and with me. They looked blankly at me and then curiously at each other to see if the other just heard what he thought he just heard.

“What do you mean, Dad?”

“I mean that I can only say yes to you on this road trip. I am not allowed to say no.”

“Yes to Everything?”


“So we can have candy?”

I paused for a breath and replied, “Yes.”

“And ice cream?”


“Ice cream for breakfast?”

“Uh. Yes.”

“And toys?”

Oof. Right. Note to self – desperation diminishes reason.

“Yes, but we need to establish some rules. First, we will have a daily budget and we are all three responsible for it. If we do not use up a day’s entire budget, we can roll it over to the next day’s budget. Make sense?”

“What’s the budget?”

“$50.” (I was making this up in the moment.) “Second, as your father I reserve the right to keep you safe, healthy, and alive, so if you ask for something that raises my concern, I will raise a yellow flag. A yellow flag starts a conversation where I can express my concern and we can discuss alternatives.”

“What if we have the conversation and we still want what we’re asking for?”

“Well, I guess as long as we are within our budget and I’m confident you’ll remain safe, healthy, and alive, then I can only say yes. Are we all in agreement?”

“YEAH! Yes. Definitely, Dad. Thanks. Let’s go. Woo-hoo!”

And so began our first Road Trip to Yesville.

Says The Wiser Amuser:
Sometimes not knowing what you’re getting into
will give you the chance to get through
what you wouldn’t if only you knew
all the crap it’ll make you do.

In the summertime, the drive from Boulder to Aspen is candy for the landscape-loving eyes. Hours of winding valleys, rock-walled river canyons, and major-mountain passes along every possible route. In the wintertime, however, though equally gorgeous, it can be a considerably longer ride and, if a storm hits the mountains, Aspen can be unreachable by car.

After making it safely and harmoniously up to the Continental Divide, through the Eisenhower Tunnel and down the other side of the pass into Summit County and the town of Silverthorne, we stopped for gas. Normally when I stop for gas the boys stay in the car and listen to music. On this occasion, however, I barely had the gas cap unscrewed before they were both out of the car and into the convenience store of the gas station. I finished filling up and went inside to find, quite literally, two kids in a candy store…with a $50 budget.

They didn’t see me walk in so I stood quietly out of view as they found one another at the far end of the checkout counter, Kai (10) reading aloud for Tragar (6) the plethora of lottery ticket options. Tragar, who’d already asked the clerk if they had shopping carts, was well on his way to exhausting the day’s entire budget by himself – red licorice ropes dangling over his shoulders to the floor, hot chocolate, Gatorade, a chocolate bar, bag of chips, silly bands, two comic books, a DVD movie, and a bald eagle/American Flag denim wallet. Kai was loaded, too, though to a lesser degree. I stood entertained, but conflicted. On the one hand, their excitement was contagious and the amount of loot they had already amassed in their arms was downright impressive. On the other hand, I had to figure out how to initiate our first yellow flag conversation without saying no. Nothing came, but as the lottery ticket discussion seemed to be evolving, the time had come. I stepped in, “Hey guys, how we doing?”

“Oh, really good, Dad,” said Tragar, “here, can you hold these?” He started handing me everything in his arms, as if preparing for another run through the place for god knows what else.

“Are you going to get anything, Dad?” asked Kai.

“Yes, probably some hot chocolate, but before I do, I need to raise a yellow flag.”

As soon as I started what I worried could become a sticky conversation – “Ok guys, my concern here is…” – Kai interrupted, “Wait, wait,” and without me uttering another word, he totally took over. “Tragar, remember we have a budget and we haven’t had dinner yet so we can’t spend too much here.” He then proceeded to guide Tragar through his choices and, to my pleasant surprise, they each walked out with a bottle of juice, a single piece of candy, and zero objections. I was stunned.

As we pulled out of the gas station, Tragar spotted the Dairy Queen and asked to go there. My first thought was to raise the yellow flag again, but I stopped myself and just said yes. An hour later we stopped for dinner in Vail and I was thrilled when both boys made healthy choices and ate every bite of their meals.

So that was day one of four. The next three were as challenging for me as they were paradigm-shifting.

During breakfast on the morning of day two, after I’d just granted Tragar a strawberry milkshake with whipped cream and six cherries on top (because he’s six) to precede his eggs and sausage, Kai granted me a no. “Dad, you’ve totally earned it, right Tragar?”

Tragar, a creature of pleasure who knows what he wants, cake, and when he wants it, now, stared blankly at Kai.

Kai, a creature of justice and eerily empathic, seemed to be grappling with the dynamics of our arrangement. I could tell he was tuning in to my internal struggle every time I said yes to something that defied our normal boundaries, like a strawberry milkshake with breakfast, for example. He knew they had a good thing going and the rules seemed to be a little too loose for his comfort. I have no recollection of any other time in my parenting when either of my kids have actually invited limits. In that sense, Kai granting me a no was like a plea for help. I raised six yellow flags on our trip. The first was for both of them at the gas station on the first night, the next five were all Tragar, with each ensuing discussion more complicated and irrational than the last. Kai wanted that chaos squashed and under control because, well, he’s also quite practical – his share of the budget was at stake. As it happened, I never used the no, but I did become more assertive at driving our activities in a way that kept Kai at peace and Tragar sufficiently satisfied.

Also on day two, we skied. We went everywhere on the mountain we all wanted to go. We rested when we were tired, we ate when we were hungry, and we drank hot chocolate because that’s just what you do. We cooperated all day. There were no yellow flags. Everything flowed.

On day three, we went to the Aspen Rec Center to go swimming. Two hours of water sliding, tackling and wrestling, lazy river chasing and kick board racing. It was fun and exhausting and as we showered and dressed I looked forward to some relaxation by the fireplace.

On the way out of the Rec Center, however, there was a climbing wall. Yes.

Next to the climbing wall was a large window overlooking an Olympic-sized ice-skating rink below. Yes.

On the way out to the parking lot there was a large sledding hill. Yes.

On any other trip, I would have said no to climbing, skating, and sledding because I was tired and not inspired, but all were within our agreed upon bounds and all ended up being a total blast.

Of the many great, unexpected twists of Yesville, perhaps the greatest and most ironic is how it empowered my sons to work their magic on me.

During our drive home, Kai expressed how nice it was to be able to ask for what he wanted without worrying how I would respond. To just be able to ask for anything. Even if I raised a yellow flag, he said, it felt okay because he knew we were going to come up with something that would make him happy. He thanked me for what had become his favorite Christmas gift. At this I suffered both sides of a broken heart, one of sweetness and one of sadness. Sweetness from his sentimentality. Sadness from having realized that “no” can sound the same to a child as “you’re wrong for asking.”

Yesville forced me to examine my parenting more deeply than ever before. For one thing, it hadn’t really occurred to me how often I say no to my sons when saying yes would actually produce much better results. Not just for them, but for me, too. I walk around with this “no, because I said so” parental entitlement. And oh how very convenient that is, but while it can ensure some predictability and preserve my authority, how much does it ultimately empower my parenting and, more to the point, their childhood?

At its best, no is an orientation tool, a parental compass for setting healthy boundaries. At its worst, no is an over-compensating implement of control that builds walls of limitation and worse, disconnection. This trip taught me what a lazy asshole I am at times. More often than I’m comfortable admitting, I’ve used no more for driving my own agendas than for guiding my children to growth and independence. Far too often I’ve behaved like a selfish dictator than as an enlightened leader.

No is the ultimate negative and its power is, ultimately, finite.

Yesville shifted my parenting paradigm to something that feels more infinitely valuable than the power of no. It gave my sons a sense of freedom and kept them oriented with simple, easy-to-accept boundaries. “Autonomy with limits,” a child therapist once suggested.

In Yesville, we enhanced our capacity to communicate, cooperate, and relate. We were kind, present, respectful, and loving – with one another and simultaneously within ourselves. Kai and Tragar were not only more open and engaging with one another, but when meeting new people they were generous and unselfish in ways I had not previously witnessed in them.

As was I.

My primary intention on this road trip was to plant positive memories. And is there anything more positive than Yes?

We’ve now completed several Yesville journeys since the first. The budget and the yellow flag remain solid. They look forward to the trips as much as I do, maybe more, as they are quick to let me know when I’m not cooperating well and am due for a trip to Yesville.

In Yesville, the lessons are abundant, as are the surprises, as is the growth in the magically-playful playground of quality time with my children.

Says The Wiser Amuser:
We glow
via Yesville’s green light
we go
through the timeless and the spaceless
we flow
with a budget and a yellow flag
we grow
enlightened within
we glow…

Go Adventure. Go Travel. Go Live.

As always, if you enjoyed reading this post, please share my blog with your connections and follow me. Thank you!


4 thoughts on “Road Trip to Yesville

  1. Nice article or even story! We will follow your blog 🙂 We also love to travel around the world and tried to capture every moments. It’ll be cool if you can check this out and share your view ! Love the way people embrace life and the unknown…

    Liked by 1 person

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