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 picked out at TJ Maxx?

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

While the examples above are not personal experiences (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 this topic?"

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 the employees you supervise - share my experiences.

This was my first holiday season being “single” since 2013. While not an eternity, I had gotten used to sharing the holidays with my (now ex) wife. Whereas I still had a wonderful break spending time with family and friends … the holiday season didn't quite seem the same.

For example, let’s discuss the “putting-up-the-Christmas-tree” tradition. In the past, putting up the Christmas tree was one of the most looked-forward to events of the holiday season. This is when you play Christmas music, crack open a bottle of Moscato d’Asti, and turn your living room into a picture worthy of the ‘Gram. And while my decorating contributions were pretty minimal, there was a sense of excitement whenever the tree went up.

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

Next, let’s discuss holiday commercials. As a kid, I always looked forward to holiday commercials. Whether it was Anheuser-Busch with their famous clydesdales prancing through the snow, De Beers with their “A Diamond is Forever” holiday commercial (search for the song “Palladio” and thank me later), or Corona with a single palm tree lit up with lights … there was always something memorable about holiday commercials.

This 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. The holiday potluck is a staple in many schools and district offices. It is a time for staff to bring their favorite dish, celebrate the end of the first semester, and to share holiday break plans. 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.”

This year, this answer got a little more tricky. Whereas most employees spoke of doing amazing things with their families and kids, I had little to share other than going to my hometown to see my parents. With no disrespect to my family (love you guys!), at 39 years of age shouldn’t I be doing something much more “adult” than saying “I’m going home to see my parents?”

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 stays so optimistic during the holidays. One recent study indicated that 88% of Americans feel that the holiday season is the "most stressful time of the year." Add in the fact that educator stress levels have skyrocketed in 2021, and there is a good chance you or your employees are going through difficult times.


Ok, let's take a deep breath. There are ways to survive - and thrive - during the holidays while being single. Although I'm still a work in progress, here are six ideas that have helped:

Routine: One of the easiest things to do during the holiday season is to break from routine. While the idea of not setting an alarm and lounging around the house sounds enjoyable, in reality I have found that downtime is when I dwell too much on the past or aimlessly browse social media (more on this below). Instead, I have found that I feel more relaxed and fulfilled when I stick to a schedule.

Hobbies: The difference between this breakup and previous breakups is that I have something I am intensely focused on - which is publishing a second book. Every day wake up excited about getting to my office so I can do more writing (which likely sounds painful to many of you). What is your passion area? Finding something that keeps you motivated will help you stay focused during times of adversity.

Give: Giving presents is scientifically proven to be good for your mental health, and what better time to give than during the holiday season? This year I committed to giving more than ever before. Want to know what felt really good? Buying over $1,200 in gift cards from local businesses and giving them away to employees and board members.

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 also am tempted to creep on the pages of my ex. My advice: stay away from social media during times 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 how successful you are, we all go through funks in life. When this happens, realize you are in good company and tell yourself the following: There is no way I can feel happy and content in life without feeling the funk. When bad things happen, view them as learning opportunities. What have I learned 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 all kinds of time to improve yourself. What areas in your life do you want to improve? Apply for the job you always wanted. Commit more of your finances to your retirement plan. Sign up for a fitness class. 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 this idea of settling.

My job allows me to get to know hundreds of employees on a personal level. Having worked in four large schools/districts, I've had the opportunity to connect with well-over 1,000 employees.

While most employees appear to be very happy with their home-life, 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 some 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 and messages in this society have made you feel like you aren't enough without a significant other. The pressure to find a mate seems intense and unyielding, and you feel it from all sides. You didn't have a date to your best friend's wedding last spring, and he's been trying to fix you up with someone random ever since. People at your church whisper when you come around, “She's still single? What's wrong with her?” Your parents keep pressuring you to hurry up and marry someone because they want grandkids. All of that can make you start to feel like you're “less than.” 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. But these types of hasty decisions have serious consequences. Our high divorce rate may have less to do with bad marriages and more to do with bad singleness.

Consider your current situation.

Are you truly happy?

Or, are you settling?

For anyone who has read my blogs or my book, 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 it might suck as first, understand that in the long run you will be more happy.


Listen: the last thing I want to do is act like I'm a relationship expert. If my track record is any indication, I have a lot to learn.

However, as leaders we must learn how to empathize with our staff.

As employees return to our buildings this week, please understand that many are going through difficult times in their lives.

As leaders, we must understand these differences and do what we can to support staff.


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