All Work and Play: Making Your Day Job a Little Dreamier

My first real, "grown-up job" was downright grueling.

As a Director of Teaching Interns and a Dean of Students, I spent my days sitting in meetings, auditing classes, and guiding budding educators. Nights were filled with one-on-ones, dorm rounds, and study halls—ensuring students were engaged and safe.

By 11 p.m., I was drained—exhausted, completely wiped.

And I loved every minute of it.

That first job remains the most demanding I’ve ever had. It also remains one of the most fulfilling.

Now, what if we could all have this experience...in every job we take?

Why Work Should Be Enjoyable

With work—and the fact that we all kinda "have to" do it—we've been sold a lemon.

We've all been told to find a good job, steady work, or a respectable profession. But rarely are we encouraged to seek work that excites, challenges, or aligns with our passions. We're told to prioritize stability over satisfaction, security over fulfillment. But I think work takes up too much of our lives to simply endure.

Why not aim for a role that offers purpose, connection, or even moments of joy?

With an average of 96,000 hours spent at work—more than we spend with family or on personal interests—it makes sense to figure out how to enjoy it.

How to love work today

The good news is that work can be enjoyable. And no, this doesn’t require finding a “dream job” or convincing your boss to approve budget for a ping-pong table (besides, some of the most extravagant playrooms are found in some of the most toxic workplaces). It does, however, require a shift in mindset and some intentional strategies. Here are three that have worked for me and others I’ve coached in their career journeys.

1) Love the Job You’ve Got

Until you land your dream job, focus on what’s dreamy about the one you already have. This isn’t about toxic positivity. I'll admit that there are plenty of workplaces that deserve a one-star Yelp review. But even in the most challenging environments, there are usually aspects of the work that bring satisfaction, curiosity, or even joy. The key is building the emotional muscle to recognize them.

Maybe it’s a particular task that energizes you, a colleague whose humor makes the workday bearable, or a moment when you feel a true sense of accomplishment. Lock in on those moments. Work isn’t just a paycheck—it’s a major part of your life. Until you’re in a role that’s fully aligned with your passions, finding joy in the small things will make each day more meaningful.

2) Advocate for More of What You Enjoy

Loving the job you have doesn’t mean settling. It means shaping your role to include more of what lights you up. I learned this firsthand during my time at Cirque du Soleil, where I went from working in philanthropy to a role where I was working with CEOs, clowns, coordinators, and contortionists (at the same time!).

Now, I get that not every job is a circus. But every job does have something worth appreciating—whether it's a skill you're honing, a project that sparks your curiosity, or even just the camaraderie of your colleagues. The trick is to shift your focus toward those moments and maximize the parts of your role that bring you the most satisfaction.

3) Look for What You Want

Most of us will make several career shifts in our lifetime. So, when you’re eyeing your next move, be intentional about what you’re looking for. It’s easy to focus on getting out of a bad job, but escaping a horrible situation isn’t the same as stepping into a great one. What do you actually want? More flexibility? More creativity? More leadership opportunities? More money?

Instead of just running from the things you dislike, start looking for roles that bring you closer to what excites you. To do this:

• Note what parts of your past jobs energized you. These are clues to what you should seek next.
• Talk to people in roles that interest you. Gaining insight helps you make informed decisions.
• Take small steps toward your goal. This can include learning new skills, networking, or testing a side project.

A Note on Ventertaining

If you've read my other posts, you know I'm big on avoiding ventertaining—venting as entertainment at work. Why? Because it stretches a three-minute frustration into an hour-long complaint session, making things feel worse than they are. Constant venting also rewires your brain for negativity, making complaints your default setting.

This doesn’t mean you should suppress frustration—processing emotions is necessary. But there's a difference between addressing problems and making them the center of every conversation. If you want to enjoy work, focus on what's right instead of constantly talking about what’s wrong.

Final Thoughts

Work doesn’t have to be a slog. Sure, there will always be tough days, long hours, and tasks we’d rather not do. But the difference between dreading your work and finding fulfillment in it often comes down to perspective and action.

?? Find what you love in your current role.

?? Advocate for more of what excites you.

?? Be intentional about where you go next.

With 96,000 hours of work ahead of us, we owe it to ourselves to make them count.

As the owner of CoWorks Leadership Strategists, Jay Guilford offers virtual and in-person workshops on leadership and teamwork essentials.