Back in the days when we all saddled up our horses before heading into the office, the fall marked a time of year filled with a blessing amid the chaos. While we were jotting down menus for Thanksgiving gatherings and getting deep into Christmas shopping lists, there would often be a simple yet thrilling entry into those last weeks of work prior to the start of a new year.
Typically, at this very time of year but decades ago, a company-wide notification would be sent reminding each employee that any unused vacation days must be used before December 31st.
Of course, in those days, there was no such thing as Personal Time Off (PTO).
In those days, time off was clearly defined as company holidays, sick time, vacation days, and for the ultra-lucky, a few no-questions-asked personal days. When we took a day off, we were tasked with defining it correctly on our timesheets meaning sick days were for being sick and vacation days were for being on vacation.
We wouldn’t dream of using sick days for anything other than projectile vomiting lest we jinx ourselves. If we did try to beat the system (once we were allowed to carry over a few unused vacation days into January), it was almost guaranteed that we would be caught shopping at Forever 31 by the boss we’d feigned illness to just hours prior. Oh, yes, hey, hi! So funny to see you here. I started feeling better after lunch (checks Swatch to make sure it is, indeed, after lunch).
There did come a time when hoarding days became the norm and we would use up those sick days first (regardless of actual illness), vacation days second, and we would hold onto those no-questions-asked personal days like they were our only lifeline to frivolity.
That was sometimes tricky as vacation requests had to be submitted months in advance and human resources was on the case if a future request came in marked as sick days. Oh, right, silly me. Of course that was my mistake. How would I know if I am going to be sick on June 17th?
When requesting vacation days, we often felt it necessary to offer detailed itineraries in case someone else requested the same day and the tiebreaker simply came down to who had the better plans. Mary’s going to volunteer at an orphanage in a third-world country for her vacation? I mean, wow. Yes. Um, sure, of course. I’m sure my entire family will understand the change in our beach week.
Back then, the great American railway had just opened so tickets to travel had to be purchased months in advance and there was always a looming vacation request question: Should I submit for approval first or buy the ticket first? What if I buy the ticket and Mary has to accept her Nobel Peace Prize on the same day? Eff you, Mary.
Back in the old days, the final quarter of the year activated human resource departments nationwide.
These months were dedicated to selecting the following year’s benefits which often resulted in higher payroll deductions for less coverage. These months were dedicated to winking at managers while telling them that employees who got great reviews could get great raises as if we didn’t all know that, in the end, we would a tiny cost-of-living bump rather than a merit-based raise. These months were dedicated to driving employees out of the office lest they have a single vacation day leftover that could potentially be carried over into the new year.
November often started with an announcement sent from the top down urging people to take any unused vacation days promptly and most definitely before year’s end.
The announcement frequently included words like “coordinate,” “pre-approval,” “adequate coverage,” or “should your workload allow it.” For those lucky employees who had saved those coveted no-questions-asked personal days off? They were the envy of the office.
For the rest, a peer-to-peer dance began as each figured out the best days to take off while promising not to interfere with a co-worker’s days off. The very, very unlucky–those with zero time-off seniority–simply faced a year-end in which they would be tasked with covering entire departments while sitting alone at work on both Christmas and New Year’s Eve.
In today’s world of unlimited PTO, much of that stress is gone but, in turn, many take less time off than in prior decades. With no real reporting, time off is often forgotten. With no real reporting, the tether to the office is never fully cut and many vacation knowing that the cost of unlimited PTO will be a work call or email interrupting a much-anticipated mojito.
Unlimited PTO sounded like a dream when companies first started shifting to this fascinating policy. Yeah, they trust me enough to take time off without a babysitter approving it! All I have to do is make sure I don’t leave anything critical undone, arrange a couple of back-ups, and I’m free!
Prior to unlimited PTO, families would gather around kitchen tables, each January, comparing notes against a calendar as heads of households prepared to submit vacation requests for the entire year. The earlier those requests were submitted, after all, the better chance of approval. It often didn’t matter if the vacation specifics were mapped out, just that the time off was.
Unlimited PTO quickly became a major plus when entering the job market.
Before this trend, switching jobs meant carefully weighing vacation time and the knowledge that starting with a new company meant returning to the bottom of the time-off Totem Pole. You might have hated where you worked, but at least you had accrued three weeks of vacation and were in the top five when it came to time-off seniority. We hadn’t yet entered a land where vacation time could be used in compensation negotiations. Woohoo! I was offered the job! Yeah, a nice bump in pay. Still, only three sick days, five vacation days, a single personal day, and, oh right, I’d be last in line for approval. Maybe I’ll just stay put.
PTO really was a dream. It still is, but only if you use it.
Have you taken your time off yet this year?
Have you taken at least a week to regroup, recharge, and regenerate?
Are you currently reading this in a panic because, DAMN IT, another year went by without an adequate break?
Here is your PTO-PSA.
Copy the note below, paste it into the body of an email addressed to you, and then press send. This reminder was probably exactly what you were missing. After you’ve done that, copy the note again. Paste it into a second email addressed to you. Now, schedule that email to go out at the end of October 2025. You’re Welcome.
Dear [Insert Your Name],
As we approach the end of the year, I encourage you to make the most of that unlimited time off. You’ve all worked incredibly hard this year, bringing energy, commitment, and resilience to your role. Your dedication has been vital to the success of your workplace and I’m sure they truly appreciate everything you’ve accomplished.
Taking time off is essential not only for your well-being but also for sustaining the high levels of performance that contribute to your employer’s success. Time off can improve overall productivity, reduce stress, and boost creativity – all of which benefit not only you but also your entire team.
Whether it’s a few days to recharge, time with family and friends, or an adventure to explore new places, stepping away from work can bring you back feeling refreshed and ready for what’s next.
The last months of the year can be a busy period for many. Let your co-workers and management team in on your plans to avoid a year-end debacle and to help your team plan accordingly.
Remember that time off is considered a part of both your compensation and benefits package – it’s there for you to use!
Thank you again for all your hard work, and enjoy your well-deserved time off!
Warm regards,
Jyl B
Head Bear
Bearlow Productions, a company definitely not affiliated with yours