The 7 Reasons Why I Have So Many Vacation Days

I begin by sharing that, as of today, I have more vacation days on the books than I have ever had since taking my first job as an Adult Probation Officer for Crook County over twenty-eight long years ago.

Not something that I would have expected to have or to be writing about at the age of fifty when I would rather be writing about more extensive traveling, rest, and relaxation instead of continuing my workaholic ways into my twenty-ninth year of full-time employment.

The reasons for my stockpile of vacation days are myriad but similar to why many other Americans do not take as many as we collectively should. Two or perhaps three reasons, by my count, are specific to my own unique set of circumstances.

Serving as an economic developer for a mid-sized Chicago area suburban community is how over ninety percent of our family’s income is derived. My wife’s part-time job, the capital gains and dividends that we collect, my side hustles like writing and selling unloved items on eBay, and the like, round out our income.

But our family’s typical eight thousand to twenty thousand-dollar months get paid by my crazy work ethic of showing up come rain, shine, or polar vortex day after day, month after month, and year after year.

The reasons boil down to a mixture of fear, duty, work ethic, and the ongoing pandemic. The reason why it may pique your interest is that some, or all, of these reasons, may apply to you as well. You may even have additional reasons that do not apply to me or are particular to your own unique set of circumstances.

My own reasons are as follows:

1. Fear of Being Seen as Replaceable

Lingering job insecurity is an unfortunate consequence of the seemingly never-ending tough economic times. It is not as if I have the greatest job ever, but I am keenly aware that there are not only people with economic development knowledge within the community that I work in but also some younger city employees that covet my position for if and when I move on from it.

There are still millions of unemployed and underemployed folks. People who would salivate at a job like mine, paying a six-figure salary and including (shitty) health insurance and other benefits like paid vacation and sick time.

There are numerous ways to address this fear, but if you too sense a correlation between job insecurity and unused PTO, then you must first combat the idea that taking a vacation is a replacement-worthy offense.

Personally, my role has become more pronounced and important since the worldwide pandemic began in March of 2020. But that does not mean that I could not be replaced with a younger, lower-paid version of myself.

2. I Fear My Return

I am the go-to point person on business- and development-related projects for a mid-sized suburb in the Chicago area.

An economic developer without businesses and developers to work with would be in for a world of pain.

So when I continually show up to my office like clockwork, I am quite adept at handling the business meetings that I typically have, the unending reports and social media posts that I do in my normal course of business, and answering the steady stream of business-related inquiries that I get per day.

Should I relax for a week and not look at my email or check my voice mail would ensure that I return to dozens of messages, mostly from people who were told that I was out and asking me to get back to them on Monday of my return if possible.

Of course, after many long years of working for local governments, I have mastered the art of prioritization. I will return the Mayor’s call first in any and all events, but the tenth video gambling, massage parlor, hair salon, or marijuana call of the month may just get deleted.

It often takes me the entire week of my return to catch up with what I missed while out, so even though I absolutely love going on vacation and would and should go more often, the dread sets in a day or two before my return and once I do, I sometimes question the wisdom of having gone at all.

3. They are Super Expensive

It is not as if I have never taken my family on vacation.

Whenever the four of us go anywhere together, it somehow winds up costing somewhere between five hundred and a thousand per day, all in and including airfare, accommodations, foods, tickets, fees, and whatnot.

Even spending a week visiting my father-in-law and his wife in Arizona in December 2019 cost around five thousand for an eight-day trip. Our lodging alone exceeded $2,500 including our final night in Vegas.

Having traveled to Denver twice recently, just me and my son, we spent somewhere around $1,500 each time, and we were not living lavishly by any means, just pretty nicely.

Whatever the case may be, vacations can be super expensive!

4. It’s Become Difficult to Plan

Before our son’s recent move to Denver, and especially before the pandemic hit, our family of four was busier and more highly scheduled than most prototypical suburban families.

During those times when there were breaks from work or school, we typically had holiday concerts, dance recitals, gigs, and whatnot taking up those slots. During some of those holiday weeks that many families went on vacation, we would have something to attend three or four nights.

Once you get into the mindset that a vacation is a chore or a pain to plan, you are setting yourself up for vacation failure.

Planning a vacation can be like any project at home or work. You need to break the task into smaller pieces, even as little as 20 minutes of your free time.

Create a plan and allocate two to four months to plan a short trip and twice as long to plan a major vacation. Check off tasks as you accomplish them and before you know it, you will have an entire vacation itinerary ready to go.

5. I’m a Unique Guy

If you were to ask the Mayor and City Council whether they thought I was a valuable employee and doing everything that I could to attract new business and investment to our city, you would get a mixed bag at best.

Nevertheless, there is nobody else in my city who knows exactly what I know and possesses the same skillset. I suppose that could be said of multiple employees, but I am not exactly one out of forty police officers or one out of fifty public works laborers, each of whom could be replaced by a similarly competent cop or laborer in relatively short order.

Despite ongoing efforts to digitize much of the information that resides in my brain, I possess a wealth of knowledge about properties, employees, landlords, developers, brokers, and what transpires behind the walls of the five hundred or so businesses in our city.

During a few days earlier this year when both my boss and I were going to be out of town, he asked me if that meant that all of the economic development in our city would just stop for that time.

I assured him that it would continue while I was in Denver and he was in the Florida Keys (paid for by his parents). The millennial that he is, he continued checking emails and voice mails the entire time, anyway.

Thus, besides coming back to a mountain of work, I do not want any major development projects to stagnate or lose momentum because I am enjoying a few days away.

After all, I want to keep the two-thirds of the elected officials that do not want me out on my side.

6. Our Company Culture

The “CEO” of our organization, known as a City Manager in municipal government, takes ample “vacation time.” However, the manager tells me about hours spent on phone calls with the elected officials and dealing with problems while out of state or even the country.

It is what is now commonly referred to as a “working vacation.”

There is never really a time without major accidents or crimes, water main breaks, deadlines to be met, or other things that require immediate attention in a mid-sized city.

So even though my former (now-retired Baby Boomer) boss would totally shut off the city while on vacation, the current millennial leadership is responsive 24/7/365.

Waiting in line for a ride at the Magic Kingdom? In comes a phone call from work. Spending a leisurely day at the beach with my daughter in the Upper Peninsula? In comes a call from work. Enjoying a dinner out in New Orleans with my sister’s family? Well, you get the drift…

I have fielded calls from work in each of the above situations, and guess what? Not one of them could not have waited until my return the following week.

But being the good little worker bee and “team player” that I am, I treated every one of the above calls, and many more, the same as if I was sitting at my desk on a Monday morning.

While not technically “a company,” I could say that it is our city’s culture.

7. My Stockpile

Under the unique terms of the city that employs me, we are allowed to “bank” or “keep on the books” twice as many vacation days as we are allotted every year.

By the same token, once we keep at least eighty hours on the books, we are allowed to cash out up to ten days per year.

I once resolved quite a few years ago when our children were younger that spending time with my family was more important to me than gaining a few extra hundred or thousand dollars here and there.

Well, that totally fell by the wayside last year, a year that under different circumstances I would have planned several nice family vacations before our daughter went off to college and our son to graduate school.

I will spare the details here about the enormous amount of stress that the pandemic caused for the business community in the town where I work, but suffice it to say that 2020 was both the most stressful work year that I have endured as an economic development professional and a year that I was only able to take six-and-a-half days off.

Not that I was ever officially classified as an essential worker, but the work that I did throughout the course of the pandemic to try to help as many businesses as I could made me feel as much.

So I trudged into work day after day, week after week, and month after month last year while most of my friends and relatives were working remotely and wound up taking only twelve hours more than one week off in the entire year.

My stockpile of days grew and I wound up cashing out the maximum amount of days allowed (ten), netting me an extra three-and-a-half thousand dollars of take-home pay, half of which went towards paying in taxes.

Therefore, the amount of vacation days that I have continues to grow, even as my desire to take time off increases. It makes me think often of the day four years from now when I will at least be eligible for a pension if I can succeed at remaining a de-facto essential employee and remain gainfully employed until then.

I would rather share details of how I make money while I sleep or work remotely in exotic cities whenever I feel like it like my rich younger brother does.

I end this long story of why I have so many vacation days on the books by sharing what happened when I asked my boss for the three days off between Christmas and New Year’s next month.

Because we are not traveling to visit my father-in-law in Arizona this year and my boss is taking that particular week off, I have been asked, or directed if you will, to “hold down the fort.”

I would be lying if I wrote that I am good with this or planning on giving my best effort.

Having been a working economic developer for over two decades, it is a given that any business owner or developer of any consequence will not be conducting any important business that week. They will be traveling or spending quality time at home with their own families. Just like I should be doing and you should too.

It will cause me to cash out a few more days and come into the office just to hang out, surf the web, order some nice lunches and go for as many walks as I can.

It may even wind up being better than being at home!