Some people are used to showing up in the wrong place, at the wrong time, with the wrong stuff.

Others of us double-check our calendars, recheck that voicemail, look up an address once again, and plan for extra time for bad traffic conditions, because we never want to show up at the wrong place, at the wrong time, or unprepared. Some of the double-checkers and planners hate to be late, can’t stand being wrong, don’t want to let anyone down, or fear looking unreliable. Others have busy lives like houses-of-cards, with multiple kids to get to multiple places, many work obligations, and unpredictable metro area traffic conditions. If one card slips, the whole house falls down.

Over the last 13 months, the double-checkers, along with just about every other human being on our planet, have been shown that no matter how carefully we plan, sometimes unpredictability is unavoidable. Since Covid-19 appeared, we have all learned what it’s like to be surprised by plans going awry.

Covid-19 has spawned many new obstacles, even for those of us who haven’t been affected health-wise. Traffic may not be much of a concern, but maybe we have to plan for extra time to wait in a line outside a grocery store until numbers of shoppers are low enough to be admitted. We’ve gotten used to waiting in a parking lot until enough patients have been brought in to exam rooms or dentist chairs before we can enter a building. We’ve had to reschedule doctor appointments because of stay-at-home orders, Covid-like symptoms, or because an office located in a hospital seemed unnecessarily risky to go to at certain times.

And the planners among us have learned that not all obstacles can be avoided. There’s not always a way around or forward or through. Most startling of all the revelations brought to light by Covid-19 is that there’s not always an immediately obvious treatment or cure for an illness, anywhere in the world, for any amount of money, even though every one of us is at risk.

But many obstacles in modern life can be anticipated.

In my work as an architectural specifications consultant, I don’t know when I started doing useful, organized planning things such as putting into my work calendar the day and time by which to expect deliverables from my architect-clients’ other consultants. I work on multiple projects at one time, and can’t keep all this in my head. I know for certain that this practice has headed off some potentially missed deadlines and has uncovered some schedule changes that I had not been informed about – preventing problems for my architect-clients, their other consultants, and myself, because I knew to follow up with people when when I had heard nothing by the time I was supposed to receive something.

I wasn’t born organized or proactive.

As a parent of two teenage boys, I’ve watched them learn, grow, and develop all their lives. This observation has cast a lot of light onto the development of my own planning and organizational abilities. I figured out some of my practices on my own, and some were suggested to me. Not much was taught – or it’s possible that I just refused to absorb the tips that may literally have been taught in high school when I was 13. Most people need a bit of experience and context in order to absorb the skills they are taught. For many people, those planning and organizing tips won’t really stick in the mind long enough to be put into practice if there’s no actual experience to associate them with – often some shortfall experience is required. I will never forget hearing my 16-year-old neighbor give a good idea to my son, who was 14 at the time and had forgotten his shin guards, about putting everything he needed to go in his soccer bag on top of the bag the night before, but waiting to actually pack until morning, so he knew exactly what was in there in the morning, and didn’t have to unpack to double-check. This approach works for me, too, but it took me decades to figure out on my own! But this boy’s mom is organized enough to teach her son how to organize himself – and to give the tip to others!

As a careful planner myself (now), I take every opportunity to point out organizational tips to my kids in the appropriate context. Being teenage boys, they don’t always take my suggestions to heart. This was most obvious during my proofreading of my older son’s multiple college applications. I lost track of how many times I told him to redo and reupload his resume because he kept missing one of several capitalization or punctuation errors I’d pointed out, and I kept finding them in the “final” versions of his applications. I’ve always been a proofreader, which not everyone can be, and I’m happy to fill that role for people in my family – but the people I do this for need to plan ahead and take into account the time this will take and the time to go back and fix things if errors are found – especially before those college application deadlines!

It may have taken me a while, but I know now that I need to ask for other consultants’ specs in time enough not just for me to compile everything into the project manual, but also in time enough for me to report back to them so they can redo and resend things if I notice problems that they didn’t catch before sending – like when “track changes” “all markup” was turned on when PDFs were made and they inadvertently sent me documents not suitable for issuing, or when filenames are somehow not matching the files and we end up short one spec section yet have a duplicate of another.

Age and experience have taught me that systems don’t always work properly, even in first-world countries, even at well-established institutions. But if we add routine double-checking and some schedule cushion to our practices, we can avoid some problems.

Well before those college application deadlines, but after my son had sent in college entrance exam results, transcripts, letters of recommendation, and applications, I encouraged (ok, nagged) him to check all his college application portals to make sure that everything that he’d sent was actually received. Almost everything was… but almost isn’t enough. My son was able to head off a problem by figuring out well ahead of time that his ACT scores never made it to one of the universities he sent them to, and he was able to resend the scores before the application deadline. He would have never known in advance that his good test scores never got there and that his application was incomplete if he hadn’t double-checked that application portal. I think he will remember this experience, and I hope that he develops into a planner and a double-checker.

Through experience, I have learned to always send a followup email, with no attachments, after I’ve sent an email with a large attachment. Project manuals can be massive PDF files, and sometimes emails with such attachments don’t make it to my architect-clients when I send them. I have learned that the absence of a notification that my email didn’t make it is not an assurance that my email made it. So I always send a followup email.

Some system breakdowns simply cannot be planned for or worked around. This has been made very clear to me in the Covid era. A call from school about a sick kid always makes parents jump up and drop what they are doing at work, but getting a call from school about a kid with Covid-19 symptoms who needs to be picked up and tested due to a past exposure at school even after a quarantine is a whole new level of unplanned obstacle. This is the stuff we just have to take a deep breath about. It’s not nearly as tragic or unexpected as an emergency such as a Covid infection, a car accident, or a death in the family, but for many people, unexpected things like this have happened so many times in the 13 months, and they simply can’t be planned for. This has been a year of taking many deep breaths.

If our way is blocked, due to an avalanche, a car pile-up, or unexpected road construction, are we simply stuck? Sometimes we are. We’ll have to wait and be late, or we’ll have to turn around and we won’t make it at all. But sometimes, maybe, if we had factored enough extra time into the schedule, we can sort out a way around when we encounter an obstacle. When it’s truly impossible, we just have to take a deep breath.

Sorting out the truly impossible from the obstacle that we just need to grit our teeth and muscle around is something that many of us have been figuring out over the last 13 months. Some of the people who are habitually late and unprepared truly have more obstacles in their paths than the rest of us, through no fault of their own. But some, like the kids and teens among them, and those of us who know that we can always be improving, could benefit greatly from some thought and tips on planning and organization. None of us is born with these abilities, and most of us don’t figure it all out quickly on our own. I’m still working on it… and working on taking deep breaths, when that’s truly the only thing that can be done.