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Love ... Actually?

“It’s the Most Wonderful Time of The Year”

Those are the words that begin Andy Williams’ famous 1963 song.

Regardless of what you celebrate, the holiday season is magical in many ways.

From decorating sugar cookies with your children, to cuddling with your spouse in front of the fireplace, to waking early to open presents with your family ... the holiday season is truly memorable.

But what if you are single?

What if - rather than bake cookies with your kids - you find yourself eating raw Pillsbury Christmas Tree cookie dough straight from the box?

What if - rather than cuddle with your spouse - the only cuddling you're doing is with the throw blanket your ex purchased from TJ Maxx?

What if - rather than opening presents with family - you find yourself watching The Christmas Story marathon while drinking spiked eggnog?

While these examples are not personal in nature (ok ... maybe the TJ Maxx blanket), let’s face it: The holiday season can be tough on singles.

If you know, you know.


"Oh gosh Jared - here you go again!" you may be thinking. "Why should I care about relationships?"

While you may be happily taken, remember that 50 percent of American adults have or will experience divorce at some point in their lifetime. Furthermore, it is estimated that 30 percent of American adults are single at any given point in time ... meaning that many readers - or many of the employees you supervise - share my perspective.

In 2021 I experienced my first “single” holiday season since 2013. Although not an eternity, I was used to sharing the holidays with my (now ex) wife. And while I still enjoyed spending time with family and friends … the holiday season didn't quite seem the same.

For example, let’s discuss Christmas trees. In the past, putting up the Christmas tree was highly anticipated and marked the beginning of the holiday season. In our house, it was common to blast some holiday tunes, crack open a bottle of Moscato d’Asti, and share some laughs while decorating O Tannenbaum. And while my contributions were minimal, joy was felt whenever the tree went up.

This particular year, things were much different. Whereas many people quickly put up their tree after Thanksgiving, I postponed the event as long as possible. It wasn’t until mid-December when I decided I should probably do something … only to realize that my ex took every holiday decoration we owned other than a mini-Christmas tree (which I proudly displayed in the living room).

The extent of my holiday decorating in 2021.

Next, let’s discuss commercials. As a kid, I always enjoyed watching advertisements on television during the holiday season. Whether it was Anheuser-Busch with their famous Clydesdales prancing through the snow, De Beers with their “A Diamond is Forever” holiday ad (search for “Palladio” and thank me later), or Corona with a single lighted palm tree in the Caribbean … there was always something memorable about holiday commercials.

This particular year, the holiday commercials hit different. No, VRBO - I don’t want a private cabin getaway for my family of eight. No Lindt Master Chocolatier with your fancy white hat, I have no need for your holiday truffles. No local Lexus dealership, I am not interested in your December to Remember sales event.

Finally, let’s cover a topic in which all school leaders can relate: the holiday potluck. Potlucks are an honored school tradition, with the holiday version being the granddaddy of them all. The holiday potluck is a time for staff to celebrate the end of first semester while grazing on an endless medley of homemade dishes, dips, and desserts.

During potlucks, holiday break plans are a common topic of discussion. In the past, these conversations were pretty straightforward: “My wife and I are going to visit each other’s families and spend some time together.” But in 2021, I felt embarrassed by my answer. Whereas most employees spoke of making memories with a spouse and kids, I found myself saying “I’m going home to see my parents” as if I was a 19-year-old college kid.

Before I go any further, let me be clear that I am being overly dramatic on my assessment of singleness. As you're about to find out, things aren't really that bad if you stick to a few core principles and focus on staying positive.

However, I also understand that not everyone manages to stay so optimistic during the holidays. One recent study indicated that 88% of Americans identify the holiday season as the "most stressful time of the year." Add in the fact that educator stress levels have skyrocketed in the post-COVID era, and there is a good chance that the holiday season is difficult on you or your “single” employees.


Ok, take a deep breath.

There are ways to survive - and even thrive – while being single during the holidays. Although I'm admittedly still a work in progress, here are six ideas that have helped:

Routine: Breaking from routine is fairly common during the holiday season as most people savor the opportunity to sleep in late and lounge around the house. While on the surface being “lazy” sounds enjoyable, in reality I have found that downtime is when I’m most vulnerable to negative thoughts. Ironically, sticking to a schedule and keeping myself busy prevents me from having feelings of loneliness and regret.

Hobbies: The difference between my divorce in 2021 and previous breakups was that I had something to keep my focus - which was writing this book. Rather than wake up lonely each morning because there was no one to share a bed with, I woke up feeling excited about my writing. What is your passion area? Finding something that keeps you motivated will help you stay grounded during times of adversity.

Give: Giving presents and making donations are scientifically proven to be good for your mental health. And what better time to give than during the holiday season? When I found myself single during the 2021 holiday season, I committed to giving more than ever before. One of the most rewarding things I did was buy $1,500 worth of gift cards from local businesses to give away to employees, students, and families.

Social Media: I have a love/hate relationship with social media. As a school leader and content creator, social media is part of my job. However, spending too much time on social media is a recipe for disaster! Not only do I become envious of other people's lives, I am also tempted to creep on my ex. My advice: stay away from social media during moments of vulnerability. And when you do have to post something for work ... get in and get out as quickly as possible!

Embrace the Funk: Regardless of who you are, we all go through funks. When this happens, realize you are in good company and tell yourself the following: feeling joy is impossible without also feeling the funk. Down time should be viewed as learning opportunities. How can I grow from this experience? What mistakes will I avoid in the future? Remember - the funk will eventually end. And when it does, you'll be stronger as a result.

Focus On Yourself: Being single has some major advantages, one being that you now have time to improve yourself. What areas in your life do you want to upgrade? Apply for a new job. Invest more money. Take your dream vacation. Sign up for fitness classes. Start a side hustle. Many people realize that their full potential was being limited by a former partner.


Speaking of potential being limited by a partner, let's talk about settling.

My job has allowed me to meet hundreds of educators. And while most employees appear to be happy with their homelife, I can’t help but notice a small percentage of employees who are adversely affected by their romantic relationships.

For many adults there is this idea that being with someone - anyone - is better than being alone. And while at times I have been guilty of having those same feelings ... I have discovered that some employees are in really, really bad situations. When I hear their stories, I can’t help but think, “Why do they put up with that!?”

One of my favorite books about relationships is Relationship Goals by Michael Todd. In his book, Todd discusses the misconception that you can't be happy unless you are with someone:

If you're single, I'm sure many people have made you feel like you aren't enough without a significant other. The pressure to find a mate seems intense and unyielding, and being single can start to feel shameful. Your life seems incomplete or even like a failure. This kind of thinking can cloud your judgment until you find yourself rushing into relationships that don't suit you, settling on someone – anyone – just to satisfy others and calm your fears.

Consider your current situation.

Are you truly happy?

Or, are you settling?

For anyone who has read my previous work, you understand that I am a big proponent of refusing to settle in any aspect of life. Whether it be our jobs, our hobbies, our minds, or our relationships ... we have limitless potential.

"But Jared," you may be thinking. "We've been together for soooo long! And we have soooo much history together!"

In psychology, this is called the sunk cost fallacy. The sunk cost fallacy describes our natural bias to continue investing in something that is no longer serving us or might even be detrimental to us because of the time, cost, and effort we have invested.

Couples who are in bad or even toxic relationships will often stay because they feel like if they walk away, they will throw away everything they invested in the relationship. But rather than examine the past, people must consider the future.

Will I be happy with this decision 20 years from now?

Or, will I regret the relationship choices I made?

I'm not suggesting that we throw in the towel at the first signs of trouble. Couples should do what they can to salvage relationships, especially when kids are involved.

But when you’re still miserable after years of trying to make things work, sometimes it's better to cut your losses. While life might get very difficult at first, understand that in the long run you will be much, much happier.


The last thing I want to do is pretend to be a relationship expert. My track record indicates I have a lot to learn.

However, as school leaders we must understand the dynamics of relationships. Specifically, we must learn how to empathize with staff.

When the holiday season arrives, don’t assume that it’s “the most wonderful time of the year” for all employees. In fact – for some of your staff – the holidays could be the most difficult time of the year.


If you liked this article, you'll love my new book Learning Curve!

Learning Curve is 360 pages and PACKED with useful ideas on leadership, education, and personal growth.


1 則留言

Vicki St. James
Vicki St. James

Another amazingly insightful, engaging read,Dr. Jared Smith! Thank you for posting!!

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