The "On My Way" Paradox: 7 Traits of the Chronically Optimistic (and Slightly Unprepared)

Hey you! Yeah, you. The one who just told your friend/date/colleague you're "on your way," while simultaneously wrestling with a sock, searching for your keys, and maybe contemplating making a quick coffee?

Don't worry. You are so not alone.

It's a modern classic, isn't it? That little white lie we tell to buy ourselves exactly 3-7 more minutes. The digital equivalent of yelling "Coming!" when you were halfway across the house as a kid. "I'm on my way" has become shorthand for "I have acknowledged the plan and am currently in the process of attempting to leave, though several crucial steps may still be pending."

While sometimes it's just a one-off hiccup, for some of us (you know who you are!), it's a recurring theme. It's less about being intentionally deceitful and more about a fascinating blend of optimism, poor time perception, and perhaps a touch of chaos.

So, what's really going on with the folks who are perpetually "on their way" but still deciding which shoes to wear? It's not usually about disrespect; it's often tied to some surprisingly common traits.

Let's unpack the "On My Way" paradox and look at 7 traits often shared by these wonderfully optimistic (and sometimes maddening) individuals. And hey, maybe recognizing them in ourselves can be the first step to... well, maybe just leaving 5 minutes earlier next time.

1. The Time Optimist

This is perhaps the most defining trait. The time optimist genuinely believes they can accomplish more in less time than is physically possible.

They look at the clock (1:50 PM) and calculate: "Okay, leaving at 2:00 PM. Drive takes 15 mins. Perfect!" They don't factor in the 3 minutes to find their jacket, the 2 minutes to lock the door, the 4 minutes stuck behind a slow walker, the 1 minute waiting at a traffic light, or the 5 minutes circling for parking. Every transition is instant in their mental math.

Because in their mind, they are technically almost on their way. The remaining tasks are seen as negligible blips that won't impact the overall timeline. They believe they can warp time to make it work.

The Impact: This constant underestimation leads to a perpetual state of rushing and, you guessed it, often running late despite their best (optimistic) intentions.

Insight/Suggestion: If this is you, try adding a "buffer zone" to your time estimates. Whatever you think a task will take, add 25% more time. Seriously. It's not pessimism; it's realism disguised as self-kindness.

2. The Distraction Magnet

The world is a fascinating place, and the distraction magnet notices everything. This is a trait often linked to creativity and curiosity, but it's the archenemy of getting out the door on time.

They are supposed to be leaving, but on the way to grab their keys, they spot an interesting book title, remember they meant to reply to an email, get sidetracked by a notification, start watering a plant, or get lost researching something random online.

They might have started the leaving process, but their brain gets hijacked by something shiny. When they finally snap back to reality (usually after someone calls asking where they are), they realize they are nowhere near ready but reflexively say "I'm on my way" because they intend to be, momentarily forgetting the 15 minutes they just spent reading about the history of garden gnomes.

The Impact: Things take longer than expected, tasks get left undone, and the transition from "being at home" to "being out" is disjointed.

Insight/Suggestion: Try creating a "launch sequence" for leaving the house. A simple checklist (even mental): "Keys? Wallet? Phone? Jacket? Doors locked?" Do only these things in order without checking emails or social media during that final 10-15 minutes.

3. The Poor Planner (or Non-Planner)

Some people are just not wired for detailed planning, especially when it comes to transitions between activities.

They focus only on the main event (the meeting, the dinner) but don't think through the steps required to get there. Packing a bag, getting dressed, eating something quickly, confirming the address, figuring out parking – these are all individual hurdles that aren't accounted for in their mental timeline.

They might be ready in spirit, having conceptually agreed to leave. But the practical execution is where they fall apart. They only start thinking about the necessary steps when they are already supposed to be halfway out the door, leading to a frantic rush and the inevitable "on my way" text sent from their bedroom.

The Impact: Constant last-minute scrambling, forgotten items, and arriving flustered.

Insight/Suggestion: Try visualizing the process of leaving backward from the desired arrival time. "Okay, need to be there at 2:15 PM. Means leaving at 2:00 PM. Before that, need to be dressed (10 mins), find keys/wallet (5 mins), pack bag (5 mins). So, need to start the getting ready process by 1:40 PM."

4. The "Just One More Thing" Person

This trait is similar to the distraction magnet but more active. It's about trying to squeeze in one final task before leaving, often underestimating its duration.

"I'll just quickly finish this email," "Let me just load the dishwasher," "I'll just tidy up this one spot." These "one more things" invariably take longer than planned or lead to discovering another "one more thing."

They were almost ready, but decided they had "just enough time" to squeeze in one last productive (or seemingly productive) task. By the time they finish, they are officially late, necessitating the "on my way" text sent from their still-at-home location.

The Impact: Delays their departure and often leads to leaving tasks incomplete in a rush anyway.

Insight/Suggestion: Implement a strict "hard stop" time 15-20 minutes before you actually need to leave. When the alarm for the hard stop goes off, you must stop whatever you are doing and transition to the leaving sequence.

5. The Avoidant Procrastinator

Sometimes, saying "I'm on my way" when you're not is a form of mild procrastination or avoidance, particularly if the destination or activity is causing anxiety or just feels like a chore.

They delay the uncomfortable transition from being comfortable at home to facing the outside world or a potentially challenging situation. They might put off getting ready, finding excuses to stay put, or simply drag their feet unconsciously.

When the deadline is imminent (someone is waiting or the clock is ticking), they are forced into action but are starting from zero. Saying "I'm on my way" is a way to socially signal compliance while still being in the delayed-action phase. It buys them a moment while they mentally (or physically) brace themselves.

The Impact: Increased anxiety, missed opportunities, and a reputation for being unreliable.

Insight/Suggestion: Try to identify if there's underlying resistance to the specific event or leaving in general. Break down the "getting ready" process into tiny, less daunting steps. Focus on the positive aspects of the destination or activity.

6. The Comfort Zone Dweller

This trait isn't necessarily about procrastination but about a preference for staying put until the absolute last possible second. They dislike the idea of waiting.

They time their departure to arrive exactly on time, or even a minute or two late, rather than arriving early and having to wait. They maximize their comfortable time at home.

If any tiny variable goes wrong in their precise timing (traffic, finding keys, a red light), their perfect schedule is thrown off, and they instantly become late. They'll send the "on my way" text often just as they are actually walking out the door, having underestimated the travel time by a few crucial minutes.

The Impact: Often arriving stressed from rushing, potentially missing the beginning of events, and making others wait.

Insight/Suggestion: Reframe waiting time. See arriving 5 minutes early not as wasted time, but as a chance to relax, gather your thoughts, people-watch, listen to a podcast snippet, or simply transition calmly. Build that buffer in, not as wasted time, but as bonus peace-of-mind time.

7. The People-Pleaser (In the Moment)

For some, the "I'm on my way" text isn't about poor planning as much as it is about managing social expectations in the moment.

When someone calls or texts asking "Where are you?" or "Are you leaving now?", their immediate, almost automatic response is the answer they think the other person wants to hear, which is usually "Yes, I'm practically there!" even if they are not. They dread saying, "Actually, I haven't started getting ready yet."

It's a knee-jerk reaction to avoid sounding unprepared or disappointing the person waiting. They prioritize smoothing over the immediate social interaction over accurately reporting their status, figuring they'll just rush extra hard to make up the time (which usually doesn't work).

The Impact: While intending to smooth things over, it can actually erode trust and frustrate others more when their actual arrival time contradicts their text.

Insight/Suggestion: Practice being more comfortable with stating your actual status, even if it feels awkward initially. Something like, "Just starting to get ready, should be leaving in about [realistic estimate, plus buffer]!" is much more honest and allows the other person to adjust their expectations.

Beyond the Traits: It's All About Time Perception

At the heart of many of these traits is a fascinating aspect of human psychology: our often-flawed perception of time. We tend to be overly optimistic about the future, underestimate the time required for tasks we do often, and get easily absorbed in the present moment, losing track of minutes (which quickly become many minutes).

Recognizing these tendencies in ourselves isn't about assigning blame; it's about building self-awareness. It's understanding the why behind the rush, the scramble, and the little white lie.

Is Being "That Person" Always Bad?

For minor social engagements, a little tardiness might be a harmless quirk (though consistently making others wait isn't ideal). But when this behaviour impacts work, important appointments, or strains relationships, it's worth exploring the underlying traits and practicing small adjustments.

It's not about becoming a rigid, minute-counting machine (unless you want to!), but about gaining more control over your time and reducing your own stress levels from constant rushing.

Leveling Up Your Punctuality (If You Want To)

If you identify with some of these traits and want to change, remember that awareness is step one. Step two is gentle practice.

Experiment with buffers: Just try adding 10-15 minutes to your estimated leaving time. See how it feels.

Prepare in advance: Lay out clothes the night before, pack your bag, charge your phone.

Be realistic: Challenge your optimistic time estimates.

Communicate honestly: Practice giving more accurate ETAs, even if they reveal you're not "on your way" quite yet.

Wrapping Up the Paradox

The "I'm on my way but still getting dressed" phenomenon is a relatable window into common human traits – our optimism, our distractibility, our struggles with planning, and our complex relationship with time.

It's a paradox of intention vs. execution, often fueled by hoping time will bend to our will.

So, the next time you send that text, or receive it, perhaps you can do so with a little more understanding of the traits at play. And who knows? Maybe that understanding is the first step to leaving just a few minutes earlier tomorrow.

What trait do you identify with most? Share your thoughts in the comments below!