This Year, We’re Gonna Plan Like It’s 1999

“What we seek is the experience of being alive.”
— Joseph Campbell

Before your life became something you scrolled through, it lived on paper. It was you on your twin-sized bed, No Scrubs blaring through a boombox, thoughts pouring out as a neon glitter gel pen scratched across the pages. Writing things down wasn’t about productivity or perfect time management. It was how you made sense of what was happening inside your head. Ideas didn’t need a project timeline. Dreams didn’t need a curated Pinterest board. They just needed somewhere to land.

In those moments, planning felt intimate. Your notebook held secrets, hopes, half-formed plans, and wildly hopeful visions of the future. You wrote because it felt good to see your thoughts take shape and explore the edges of your inner world. There was comfort in the ritual: the sound of the pen, the weight of the paper, the certainty that this page belonged to you alone.

Life felt slower because you were present for it. Long before calendars synced themselves and reminders buzzed in your pocket, paper quietly did what it has always done best: it helped you feel connected to your own life. That sense of presence is worth returning to.

When Planning Lost Its Place

Planning didn’t disappear when it went digital. It scattered.

Calendars moved to screens. Notes splintered into apps and voice recordings. Tasks multiplied, duplicated, and resurfaced in new places, each one promising to make life easier, faster, more efficient. What had once lived in a single notebook was now spread across platforms, devices, and alerts that haunt us day and night.

Digital tools lured us in with the promise of an easier, more organized life. They made information searchable, schedules shareable, reminders automatic. Planning gained speed and scale. Each new app downloaded with the hope of saving time and energy. But in the pursuit of digital perfection, planning stopped being where thinking happened. It became where thinking was stored and forgotten in a digital wasteland we romanticize as a “cloud”.

More tools didn’t give us more focus. They gave us more places to forget things.

Instead of sitting with our plans, we learned to react to them. Instead of deciding what mattered, we captured everything and trusted we’d sort it out later. The tools multiplied, but focus didn’t. What once felt contained began to feel endless, overwhelming, and inescapable.

Research helps explain why this shift feels so different. Studies have shown that simply having a smartphone nearby, even when it isn’t being used, can occupy limited cognitive resources and reduce available attention and working memory capacity, as part of the brain remains occupied with the possibility of distraction (Ward et al., 2017). Digital multitasking compounds this effect. Constant task-switching increases cognitive load, making it harder to hold context, prioritize meaningfully, and think through decisions instead of reacting to them.

Handwriting works differently. Writing by hand engages broader neural systems tied to memory, sensory processing, and decision-making. It slows thought just enough to give it shape. This explains why ideas feel clearer and more anchored on paper.

In the pursuit of digital structure, we lost cohesion. And without cohesion, even the most powerful tools start to feel heavy. That’s why your smartphone feels less like support and more like noise.

Four Ways to Give Your Planning a Place

1. Decide where your thinking lives

Before planning scattered across screens, it had a physical home. There was one notebook or planner, one place where ideas showed up consistently. You didn’t have to swipe right five times to find a half-typed note. You knew where to look.

Giving your planning a place starts with choosing a single, physical space for your thinking. Not for every reminder or appointment, but for decisions. Priorities. The things that require you to slow down long enough to understand them.

Let paper be the first stop, not the backup. Before something becomes a calendar event or a task in an app, write it down. Let it pass through the page so you can decide what it actually is before deciding what to do with it.

Clarity gives you back authorship over how you spend your time and energy.

2. Write it out before you sort it out

Digital tools encourage you to capture data first and look for meaning later… if you remember it exists. You collect everything quickly, trusting that clarity will come once it’s all filed, tagged, or scheduled. Paper asks you to do the opposite.

When you write things down by hand, you can’t collect everything. Space is limited. Time is slower. You have to choose what’s worth the page. That limitation forces discernment. You have to ask yourself what matters, what doesn’t, what’s noise, and what’s still unfinished.

Let the page hold the mess before you try to make sense of it. Half-formed thoughts. Reactions you don’t yet understand. Ideas that don’t belong in a system yet because they’re not ready for one. Writing before organizing gives you a chance to see what’s actually there instead of immediately sorting it into boxes.

Understanding isn’t found in the structure itself, but in the act of deciding what deserves structure at all.

When organization comes too early, it replaces thinking instead of supporting it. This is how we end up with endless notifications, bloated notes apps and the overwhelm of apps we forgot we had. When we write things first, we can decide what really needs digital structure. This makes digital tools useful instead of overpowering.

3. Sit with your thoughts long enough for them to settle

Our brains were never created for constant stimulation. Planning didn’t used to happen alongside constant interruption. There wasn’t a device within reach, waiting to pull you out of your own head the moment things got quiet. There was no siren call tempting you to scroll when boredom sets in.

To give your planning a place again, you have to protect the space where thinking actually happens. That often means putting your phone on silent or leaving it in another room. Think back to a time before smartphones. You could read a book or doodle without wondering who might be trying to reach you. You were unreachable unless you were near the house phone, and that distance gave your mind room to wander without interruption.

Leaving your phone out of sight is a small act, but a meaningful one. It’s a way of choosing not to outsource your attention so your thoughts finish forming before something else asks for them.

This part is harder than it sounds.

We’ve grown used to filling every pause with input. The moment thinking gets uncomfortable or slow, we reach for a screen. Scrolling has become a reflex because these tools are designed to steal focus. Breaking that pattern can feel unsettling at first. Restless. Almost itchy.

But that discomfort is a threshold that leads to clarity and intention beyond superficial TikTok trends. Raw dogging your own inner life for a few uninterrupted minutes is how thinking deepens instead of disperses. It’s how ideas move past the obvious and into something more honest. More surprising.

At first, your mind will look for escape. Technology has trained our brains to seek constant, artificial stimulation. When you deny your brain the cheap high of digital dopamine, it will feel uncomfortable. Then, slowly, it will start to find its way and begin to wander. To connect things. To imagine. To surface what’s actually been waiting underneath the noise.

By creating this clear space, you will find enough stillness for your thoughts to finish a sentence.

4. Leave room for thinking that doesn’t need to go anywhere

Before planning became synonymous with structure, it was also a place for optimism. There’s freedom in the naivety of our dreams before life convinced us to be practical and realistic instead of whimsical and ambitious.

You wrote things down without knowing what they were for yet. Ideas didn’t need to justify themselves. They didn’t have to turn into goals or action steps. They were allowed to exist simply because they were yours.

Every page doesn’t need a perfect layout or even a purpose. You are allowing space for thoughts that aren’t ready to be organized yet. Ideas that want room to breathe before they’re asked to perform. Abstract before structure. Curiosity before clarity.

Paper holds this kind of thinking in a way digital systems struggle to. Apps are designed to resolve, to close loops, to move things forward. Paper lets ideas linger. It allows optimism to exist without interrogation or limitations.

Sometimes the most meaningful planning happens when you’re not planning at all. Some epiphanies only happen when you’re thinking for thinking’s sake, letting possibility stay open, and trusting that structure can come later.

That’s where your life starts feeling like it’s yours again.

What Was Never Lost

“I don’t know what I think until I write it down.”
— Joan Didion

You don’t need to rewind your life to 1999 to get this back. You don’t need the twin bed, the glitter pen, or the conviction that a single notebook entry might unlock some grand destiny. What mattered then wasn’t the era but it was the absence of interference. The fact that thinking had somewhere to go without being interrupted, evaluated, or immediately put to work.

Somewhere along the way, we convinced ourselves that we must manage everything at once: our schedules, our goals, our ideas, our anxieties. We turned to a machine for execution to meet the demand. In this pursuit, we were quietly stripped of the tools that allow us to make sense of ourselves and design our futures with intention and passion.

Paper doesn’t rush ideas forward or demand outcomes. It doesn’t reward urgency or punish wandering thoughts. It allows thoughts to arrive unfinished and stay that way for as long as they need. In a world designed to keep everything moving, that slowness is where we can mold the life we really want. Some ideas just need a place to stay long enough to tell you who you are. Analog tools create that space in a way digital never can.