STYLE Savvy: Shedding the Shoulds

Lisa Hess uncovers a small detail that could lead to big mistakes. 

There are many obstacles to organizing. Time. Habits. Lack of confidence. The shoulds. 

You know: I should do this or that. I should do it the way someone/everyone else does. I should be able to make this tool work. 

Each of these thoughts is a great big mountain between us and our organization destination. If you've been reading these posts for a while, I hope you've found some ammunition for fighting back against the first three. 

This post is about the last one.  

It’s possible that regular readers might have built up some ammunition against that one as well. Then again, I've been writing these posts for a long time — and last week, I found myself running squarely into that mountainside. 

The thing is, I didn't realize I'd run into the mountain. I thought I'd merely gotten stuck in traffic. 

Reasons or Excuses? 

Life has been busy and so, when I missed a scheduled appointment, I blamed the combination of busyness and interruptions to the routine that kept me moving forward as directed by my calendar — the one that enabled me to show up where I was supposed to when I was supposed to. 

To be fair, those first two were contributing factors. But there was another, more insidious factor in play. It was small enough to fit into my purse and was masquerading as an ally. 

My Portable Planner

I don't typically have a small planner in addition to my main planner and weekly planner because, well, that's a bit redundant. But, in order to stem the tide of appointment cards that are small enough to get lost in the recesses of my bag or end up on the floor of my car, I thought I'd give it a try. 

Help or Hindrance? 

The small planner is useful. Except when it's not. You see, in my hurry to find a cheap and easy tool, I purchased a planner where the weeks begin on a Monday. Logical enough, except that in every other planner and calendar I own, the weekly layout begins on Sunday. 

I didn't realize this discrepancy until I'd already gotten the planner home. Even then, I brushed it off. I'd adjusted to this set-up in a planner a few years back and I thought I could do it again. One might even say I should be able to do this.  

But the issue here isn't whether I should or shouldn't, or even whether I can or can't. The issue is that this is the wrong tool for the job because it puts an unnecessary obstacle in my path. 

It wasn’t until I was scheduling the follow-up appointment to the one that I'd missed that I realized the sneaky role this allegedly innocent planner had played in my predicament. Only then did I hear my own voice, captured here on the page more times than I can count, telling me that if the tool didn't work, I wasn't the problem.  

I simply needed another tool. 

A Planner in Hand? 

At this point, it's easy to fall prey to the sunk cost fallacy — I'd already spent money on this, so I had to make it work. But the financial cost was only one potential cost, and the possibility — or probability — of writing down the wrong date was an additional cost, and it was I was unwilling to incur. I'm someone who has an I need to see it personal style, which means that how things look on the page is a key factor as to whether that view will hinder my planning or facilitate it. And, honestly, I'm a bit greedy. I prefer to hold out for a tool that will go one step further: one that enhances my planning and eases my mind in the process. 

This floral traitor met none of those standards.  

Within a week, I'd replaced the offending planner with a freebie whose layout was a better match for the way my mind works. Although neither planner came with an ironclad guarantee that I'll show up where I'm supposed to when I'm supposed to, the replacement planner has an edge. 

Its layout makes it less likely I'll run face first into a mountainside. 

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Copyright 2025 Lisa Hess
Images: Canva