trespassing for the view

The Big Idea: no plan is often the best plan.


Have you ever lost control while driving on a snowy or slippery road? Where the backend of your car fishtails, and you can’t help but wonder, “How’s this going to end?”

Years ago, I remember thinking, “This ain’t good!” as my friend’s sedan skid through six inches of snow, downhill, sideways, towards a cement curb. I grabbed the passenger door and braced for impact. Curbs look like military-grade barricades when you’re unintentionally sliding toward them. As the inevitable happened, and we smacked the barricade so hard it snapped the car’s control arm, the front wheels of our front-wheel-drive vehicle were immobilized.

In full disclosure, we chose to drive through a blizzard just to slide through abandoned side roads. It was fun. When we were in control, that is. Paralyzed and helpless, it was no fun waiting in the cold for help to arrive. As the sun set, I debated how long we’d last before having to eat the feathers in our down jackets.

Whether it’s losing control of your car, your career, or any other life choice, losing control sucks. Let’s just be honest. We all love control. Which also means we love having a plan.

Plans provide us a sense of certainty, and predictability, you see. Even the most spontaneous of people create plans. Type B folks just create shorter-term plans with less warning. They still expect events and experiences to turn out as they envision.

The trouble with our love of control and planning, however, is that life rarely unfolds like we tell it. Have you noticed that? You might demand your manager notice your creative genius and promote you to your rightful position within the company. That doesn’t mean it’ll happen. It’s why for every book that’s been written about making it big and achieving your destiny, just as many pages have been written about taming anxiety and finding inner peace.

Simply put, life doesn’t always go according to plan.

I think that’s okay, though. Actually, I think it’s a good thing. I’ll go so far as to say that, often, not having a plan is the best plan.

Now, before your inner Type A cries objection, did you know that paintings rarely turn out like they do in the artist’s head, before getting started? Paintings, music, books. All art changes with each small brush, note, or keystroke. The artist learns from the paint and print already impressed on the canvas and page. From there, they know how to direct the next stroke a bit differently.

In the same way, we don’t always know what’s best for our lives. We learn what’s best by living.

But to truly live, we have to ditch the plan once in a while. All plans require predictable inputs and accurate assumptions. We’re not omniscient, so we can’t possibly account for all of the options and permutations as we create our plans.

More importantly, our lives are defined by our relationships, and relationships rarely develop as we expect (that’s not my opinion, study after scientific study concludes that relationships are the only thing that leads to a happy, meaningful life).

It’s why we say, “People are people.” People are different from everything else in the world. We all have emotions, spirits, hopes, fears, frustrations, and individual identities. These things are much more subjective than what we can quantify within a spreadsheet. It’s possible to calculate if your annual earnings increased or decreased. There’s no formula that says if your relationship with your in-laws improved over the holidays.

So, while we yearn for control in life, and we hate to feel like we’re sliding out of control, we have to embrace the reality that when it comes to creating meaningful relationships, no plan is often the best plan. Memories and human connections are too brittle. They can’t be forced to fit our molds – they’ll crumble under pressure.


Our favorite memories are the ones we never expected to make. We don’t plan them. We can’t plan them, in fact. I’ll show you what I mean: think about the memory that makes you smile brightest.

Okay, are you smiling now? Not yet? That’s the wrong memory, then. Pick a new one. Choose a moment that makes you laugh.

Are you giggling? Okay, good. That moment you just recalled – was it planned? Were you trying to create it?

I’ll bet not, because when I think about the time I’m smiling widest, it’s not my wedding day. Although it was an amazing day, I did a lot planning for that day. I (obviously) knew it was coming. Instead, I think about the night my wife and I waded into the icy waters of Lake Michigan, to climb a fence protecting a park that overlooks Chicago’s Ferris Wheel (the fence bordering the lakefront was, understandably, shorter than the rest of the fence).

As we left my apartment for a dinner date, I’m fairly certain I didn’t say, “Hey, I have this great night planned. First, we’re going to soak our pants in ice-cold water. Then, we’re going to watch people riding the Ferris Wheel, but we won’t actually ride it. Great, right?!” That night just, well, it just happened.


Married before 30 was never part of my plan. I always assumed that if I wanted to do and see things in life, I’d have to cram them into the decade before a wife, kids, and a mortgage. I was wholly mistaken, of course, but I didn’t understand that until I was ready to marry my bride (I did say living and learning is better than sticking to our plans, right?).

So, when first I started seeing this girl, Erin, who I eventually married, I was skeptical. I assumed that spending time together would throw a wrench in my plan. At the time, I wanted to focus on myself. I was building a company, racing Ironman’s, traveling, and generally doing the things I thought ambitious 20-something’s should do. I had a timeline, and I was going to stick to it.

Erin is very pretty, however, and she was interested in doing the things I liked doing. That was a very convincing combination. So after she signed up to race the Chicago Triathlon, I figured there couldn’t be any harm in seeing her for a few days each month. We started meeting at Lake Michigan’s Ohio Street Beach to swim at 6 a.m. every Wednesday morning. What guy could resist a beautiful girl joining his favorite sport?

No man, that’s who. Less than two months later, I threw the whole, “I’m just really focused on my career right now,” line right out the window. There was one specific night that convinced me. It was the night we watched the Ferris Wheel in the moonlight. While we were trespassing for the view, I ended up seeing that Erin’s worth far more than any of the selfish plans I’d created for myself.


I looked down at a text from Erin. “Great! Thanks! I’ll drive, we can park at my office downtown,” it read.

Chicago’s famed Ferris Wheel was getting an upgrade. It would be taken down and replaced after a final weekend of offering free rides to the city. Erin really wanted to go, but she hadn’t found anyone willing to go with her.

“Sounds good. I’m going to nap for 30 minutes, then I’ll meet you out front,” I tapped out my reply.

It was late, I was exhausted, and yet, I’d not only agreed to go with Erin to Navy Pier, I was excited about it. Something had changed. On most nights, I was in bed by 9:30 p.m. On this night, I was taking a nap to be ready for a 9:00 p.m. excursion.

In the two months before this night, Erin and I had met to swim in Lake Michigan every Wednesday morning. We’d cycled through the forest preserve. We’d raced a triathlon. But never had we seen each other, just to see each other. Strangely, that meant something to me.

I tried to nap, but instead, I thought about why this night felt so significant. We were just friends, right? Thirty minutes came and went as I restlessly waited for Erin’s text. My phone buzzed, right on time, and I scrambled down the stairs from my loft to the street. 

“Hey!” Erin said as I climbed into her Jeep.

“Ready?” I asked as she turned onto Lakeshore Drive.

“Very,” she nodded. “I haven’t been to the Ferris Wheel in ages.”

As it turns out, neither of us were ready for a four-hour-long wait time. When we arrived, we found an endless line of people snaking through Navy Pier, the Wheel’s iconic home.

“Woah, I was not expecting that,” Erin groaned.

“We can wait here if you want?” I offered, hoping she wouldn’t actually ask me to wait in line until one o’clock in the morning.

She shrugged. “I don’t think it’s worth it. Do you?”

“No, not really. I think we need to find a new plan.”

“Fine by me. Any ideas?”

“Yes, food,” I said. There’s no bad time for food, in my opinion. “Looks like there’s a good Mediterranean place close by. The portions look huge,” I pointed to the reviews on my phone.

Erin laughed, “Sure, we can get falafel! I haven’t had falafel in a while, either.”

Minutes later, as we sat in a restaurant booth, I scanned the menu for falafel. Clearly, there was a mistake. Falafel wasn’t listed anywhere.

“Welcome guys, can I get you something besides water?” Our waiter asked as he greeted us.

“Yes, falafel,” I said confidently.

He shook his head, “I’m sorry sir, we don’t serve falafel.”

“Oh, strange. Well, could you ask the chef to make falafel? She was really looking forward to it,” I explained.

“I’m sorry sir,” he shook his head. “I’ll give you both a minute to look at the options.”

“Strike two,” I said to Erin.

“So much for that,” she sighed.

As we picked the second-best options on the menu, we managed some small talk, and we studied each other. Each of us wanted to figure the other out.

Unbeknownst to me, Erin had been hoping that I’d take her out on a real date, in real clothes – not another swim date in wetsuits. She wondered if I knew, figuring there was no way she’d been able to conceal her butterflies.

Meanwhile, my thoughts centered on what to do after we ate. The flutter I felt as I climbed into Erin’s Jeep told me I didn’t want to be just friends. Friends eat and say goodnight. People who are more than friends linger. They find ways to avoid saying goodnight.

I hadn’t planned anything else, however. Our original plan was foiled. Then I supposed the extra-large Mediterranean portions would content me for the night. I wasn’t into dating, remember?

I was uncertain of whether Erin was open to a relationship, so I didn’t want to force anything. If I suggested something too overt, like chocolate fondue for desert, it’d seem inconsistent. People don’t go from swim caps to sexy foods in the same week. So, I figured we should just wander around for a while.

After our waiter returned to the table, I quickly handed him my credit card. “I’ll get this one. You can get it next time,” I told her, implying I wanted there to be a next time.

Bellies full, we started roaming the city. Without an agenda, we eventually found ourselves in the place that was most familiar to us. We stood on the sands of Ohio Street Beach, looking out over the waters we’d swam in just a few days earlier.

“The Lake is way creepier at night,” Erin remarked, pointing at the abyss that was the boundless, featureless Lake Michigan after dark.

“Sure does,” I agreed. “But the Ferris Wheel looks way cooler in the moonlight.” I pointed at the towering, signature wheel located a few blocks south from the beach.

“I bet the view is even better over there,” I said as I turned toward a waterfront park built between the beach and Navy Pier.

“Yeah, I bet. Too bad the park’s closed. We’d have to like, climb the fence or something,” Erin laughed.

“Good idea!” I exclaimed. “The fence is even shorter down the waterline.”

“Nate, I was kidding.”

“I’m not. We’ll only have to go thirty yards into the water. We can take our shoes off and roll our shirts up. It’ll be worth it.”

To be honest, I don’t remember how I convinced Erin that soaking our pants in exchange for a better view of the Ferris Wheel was a worthy trade. Maybe I said one of those movie lines, “When you look back on your life, how do you want to be remembered?”

Regardless, a few minutes later, barefoot and dripping lake water, we scaled the fence protecting the park. We ran into the center of the park and stood, side by side, gazing at the bright white lights rotating against the backdrop of the Ferris Wheel’s red spokes and the night’s black sky.

“Totally worth it,” I said to Erin.

“Definitely,” she said back.

It was a moment that was special enough on its own. We didn’t need to add many words. Besides, don’t we remember the feelings we feel, not the words we say?

My heart was beating so fiercely I thought it might break the silence. Which was unusual, because I’d climbed my fair share of fences. I’d been given a free ride home in the back of a squad car before. So, clearly, trespassing wasn’t to blame. Instead, it was who I was trespassing with.

It was cheesy, but as I looked from the Ferris Wheel to Erin’s glowing smile, I thought to myself, “I had the better view all along.”


I don’t think our grandparents shared our obsession with planning. They couldn’t, really. Their environment, technology, and mobility didn’t permit the same degree of control we’re afforded today. Instead, they relied on people.

My grandmother used to talk about her mother riding to neighboring farms to collect eggs, milk, butter, and flour to bake her a birthday cake. People pulled together back in the day. They needed each other.

I don’t think I could have done it. Relying on other people for something as simple as a birthday cake, I mean. That’s not me. I like the modern luxuries that give me control over things as complex as air travel. If my plans are scrambled, no problem. A-List status moves me to the front of the line, and I can switch my flight without paying any penalties.

So, during a week of literally having travel, food, errands, bills, and the rest of my life in the palm of my hand, I’m tempted to think I possess the same degree of control over my relationships. But, when that mindset is applied to romantic relationships, it’s not called convenience, or technology. It’s called selfishness.

Not long into dating, I quickly realized that Erin’s plans weren’t my plans. We were, and are, very different. So, if I wanted our relationship to succeed, I had to give up some of the control I’d grown accustomed to in my modern, single life.

That was frustrating because I wanted all the benefits of a relationship, with none of the reciprocity. Now, I’m not suggesting I was some type of angry toddler screaming I’d never share my apple juice. Selfishness is much subtler, and more surreptitious, when you’re an adult.

Sure, I liked exploring our city and tasting different restaurants – when it worked for my schedule. And yes, I liked meeting new friends and family – when I wasn’t tired from a long day at work. It was in these moments of feeling busy or tired that I noticed self-interest creeping into the quiet of my thoughts.

I’d go through the motions. I’d eat and I’d greet. But it was perfunctory, and empty of my heart, because I couldn’t do my thing on my time. On the other hand, by sacrificing my plans, I could have made a full-blooded and affectionate deposit into our relationship.

That is much easier said than done, however. We spend years and years acclimating to influence. As we mature, personally and professionally, we plant the seeds of control. We earn incomes, we develop interests. Those are good things, too. But like thick green ivy that’s pretty to look at when contained, our own interests, freedoms, and abilities can quickly become weeds that choke out everything else around it.

Don’t misunderstand me, please. We’re walking a very thin line here. Co-dependence and spineless relationships are what we produce when we don’t cultivate our own plans and personalities. But, left to grow wild, our default preference for control produces selfishness and mere compliance, not sacrifice and compassion.

We must deny ourselves without losing ourselves, you see.  

For example, in my experience, the perfect environment in which my selfishness germinates are social plans being sprung on me at the last minute. Generally speaking, I need an hour head’s up so that I’m mentally prepared to be “on.” I’m what you call an “ambivert.” I can be very charming and outgoing – when I summon the energy to be. It’s not my natural disposition.

So, if I’ve planned to write, hike, or otherwise spend a Saturday morning as I choose, and Erin asks me to do something that wasn’t in my plan, sacrifice is required. Either on my part, as I forgo my preference in favor of Erin’s priority, or on Erin’s part, as she recognizes that her plan has collided with mine.

This is the stuff that relationships are made of. Sacrifice is the glue that holds even the most unlikely of relationships together. A pure focus on the other’s interests is what makes relationships work, whether they be romantic, familiar, or collegial.

If we’re in it for our own happiness, we’ll never find it. But if we deny our happiness to focus on giving joy to the other, we’ll be filled up.

So in the end, this all comes down to the delicate balance of knowing when to stick to our plans, and when to ditch them. Other people rarely follow the plans we make, and nobody is naturally self-effacing. When these conflicting forces converge, we can’t try to control the other half of our relationships. We can’t bend the wills and desires of others to align with our own. Relationships are far too brittle. They crumble under pressure.

Instead, when it comes to making memories and building bonds, the plan that works best is often no plan at all. If we’re ready to put the other first, ahead of our selfish interests, we’ll find ourselves feeling far more fulfilled.

Is there someone significant in your life that’s talked about a new restaurant, or a new adventure? Would that thing throw a wrench in your plans? Maybe you don’t like eating Mediterranean. Maybe you don’t enjoy giving up your free evenings.

If so, I’ll bet that if you eat that meal, or try that thing, with the person you love – without expecting anything in return – you’ll find yourself with a new favorite memory.

As backward as it sounds, quit narrating the story and you’ll find the happy ending you’ve been planning for.


Want to read more?

don’t stop now, download a free preview of my latest book Living Forward, Looking Backward to read more stories just like this