PDF Summary:The Humor Habit, by Paul Osincup

Who decided that seriousness is a sign of maturity? In The Humor Habit, comedian and business consultant Paul Osincup presents a comprehensive approach to incorporating humor into daily life as a way to combat stress, boost your happiness, and even improve workplace culture.

This guide will explain Osincup’s concept of chronic humorlessness: people’s tendency to give up on laughter and play as they grow up. We’ll then explore how you can cultivate your sense of humor by practicing some of the key principles of comedy and intentionally consuming more humorous media. We’ll conclude by discussing how you can create a work environment that embraces humor and fun.

We’ll also provide background information from psychology and neurology to help explain why Osincup’s methods work, and we’ll compare his ideas to those in other books such as Atlas of the Heart and The Power of Fun. Finally, we’ll offer actionable advice to help you start applying Osincup’s principles to your own life.

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Principle #2: Take the Gifts You’re Given

The second principle Osincup shares is to be on the lookout for what he calls gifts, which are instances that you can easily turn into funny moments. These are often moments when someone (including yourself) makes an inconsequential mistake or phrases something awkwardly, thereby creating an opportunity for you to gently poke fun at them.

(Shortform note: The Incongruity Theory of Humor explains why these minor missteps often lead to funny moments. According to this theory, people laugh when something unexpected happens—the incongruity between what you expect and what actually occurs creates psychological tension, which you resolve by laughing. So, when someone does something incorrectly or says something in a strange, unexpected way, it creates humor.)

Principle #3: “Yes, and…”

Finally, Osincup urges you to keep in mind the phrase “yes, and,” which is the foundation of any successful improv performance. This means accepting what’s happening at any given moment (“yes”) while looking for opportunities to make that moment better (“and”).

For example, if your company is supposed to give a presentation to an important client and your presenter calls out sick, this mindset means accepting reality as it is (“yes, our presenter isn’t here”) and then looking for any opportunities the situation presents. (“And this is a chance for us to show how adaptable we are!”) For instance, you might divide the presentation among your remaining team members so that each of them can brush up on a small section and present it to the client.

This last principle can be especially difficult because it goes directly against people’s desire for control: their urge to say “no” and try to change things, or to compromise by saying “yes, but.” Continuing the previous example, this would mean either cancelling the presentation (saying no) or, perhaps, trying to reschedule it. (“Yes, our presenter is absent, but we could do it another day.”) However, neither of those responses would be as impressive as pulling together your presentation despite a key person not being there.

“Yes, and…” as a Radical Acceptance Practice

Osincup’s description of “yes, and…” has strong parallels with what psychologist Tara Brach calls Radical Acceptance. Most notably, Brach says that there are two key elements to radical acceptance: recognition and compassion.

Recognition is the practice of acknowledging what’s happening to you at any given moment and your reactions to those events without immediately trying to judge or change anything. In other words, it means saying “yes” to everything you experience, both externally and internally.

Compassion, the second part of radical acceptance, means responding to those recognized experiences with kindness and love. This creates the second part of yes, and: “Yes, this is what I’m thinking and feeling right now, and that’s OK.”

The combination of recognition and compassion creates a strong mental foundation that lets you face each moment as it comes with calm acceptance. As a result, you’re able to take thoughtful, deliberate action to make the best of every situation—much like Osincup describes the practice of accepting what’s happening and looking for opportunities to improve upon it.

Training Your Brain for Comedy

To close out the topic of cultivating your sense of humor, Osincup says that comedy will start to come more naturally to you with time and practice. Not only will you hone your comedic skills, you’ll actually change how your brain works by practicing the principles of improv and watching or reading humorous media. There are two reasons why this happens.

The first reason is simple: You’re more likely to notice things that are relevant to your interests. This happens because your senses are constantly taking in more stimuli than you could ever process consciously—your subconscious mind filters out most of that information, leaving only what’s most likely to be useful. This is why, for instance, you might hear about a particular actor for the first time and suddenly start noticing them in numerous shows and commercials.

(Shortform note: This is similar to life coach Jim Kwik’s concept of dominant questions. Kwik says that thinking is merely the process of asking and answering questions, and dominant questions are queries that constantly run in the background of your mind. Such questions act as powerful filters, causing your brain to prioritize information that can help you answer them. So, if one of your dominant questions becomes “What funny things happen in everyday life?” your mind will stop filtering out those funny moments. As a result, you’ll start finding the humor in things that would have seemed completely unremarkable before.)

The second reason comedy will come more naturally to you is a phenomenon called neuroplasticity—your brain physically changes and develops depending on how you use it, just as muscles that you frequently use become stronger. So, if you’re regularly training your comedy “muscles,” you’ll recognize and create humorous moments more easily.

(Shortform note: Neuroplasticity is a powerful tool with benefits ranging far beyond rebuilding a sense of humor. In The Brain That Changes Itself, psychiatrist Norman Doidge goes into more detail about how neuroplasticity works and its potential for improving people’s lives. For instance, the brain’s ability to form new connections makes it possible to treat learning disabilities, and even severe brain damage, by retraining neurons to fire in desired ways. Research on neuroplasticity has also led to therapies for stroke patients and people with other neurological issues.)

Bringing Humor to the Workplace

Now that we’ve talked about how to cultivate humor in your personal life, we’ll discuss how you can promote a work culture that embraces laughter and fun. Remember that stressed workers not only take more days off, they also cost their employers significantly more in healthcare expenses. As we’ve discussed, humor is a powerful tool for fighting stress, which is why Osincup argues humor in the workplace isn’t just enjoyable, it’s also profitable.

We’ll start by discussing how you can help your coworkers or employees understand that you’re a safe person to joke around with. Then we’ll go over Osincup’s argument that you’ll actually get better results in the workplace if you focus on creating a fun environment, and let the funny elements emerge naturally from there.

Humor Requires Trust and Safety

First of all, Osincup explains that using humor effectively, especially in professional settings, requires you to first earn others’ trust. This is because it’s absolutely crucial for people to understand you’re laughing with them, not at them. He presents several strategies to help you accomplish this. Note that these methods are especially effective if you’re in a leadership role at work, but even if you’re not, you can use these strategies as much as your situation allows.

The author’s first suggestion is to lead by example; be the first one to crack jokes and make lighthearted comments. When leaders actively engage in humor and fun, it makes team members feel safe to do the same.

He also suggests using self-enhancing humor—acknowledging your quirks and experiences in positive ways—rather than self-deprecating humor, which might undermine your credibility. For example, an expert in their field who ends a suggestion with an ironic, “but hey, what do I know?” is actually highlighting their expertise by making a point of downplaying it. On the other hand, a new employee who jokingly calls attention to their lack of proficiency may be sabotaging themselves without meaning to.

(Shortform note: Osincup says to avoid pointing out your shortcomings because doing so could undermine you, but others disagree. In Right Kind of Wrong, Amy Edmondson (best known for developing the theory of psychological safety within organizations) writes that leaders candidly telling stories about their mistakes is a powerful way to build a positive work culture. If, for example, the CEO tells a story about how their mistakes cost the company a valuable customer, employees will learn that it’s OK to make mistakes and talk about them—which, in turn, will make it easier to learn from those mistakes.)

Finally, Osincup acknowledges that comedy doesn’t come naturally to everyone. If you’re struggling to create a humor-positive culture, it’s possible to delegate your “humor responsibilities” to people who are better suited for them. This might mean working with a team member to build some humor into your presentations, finding someone with a fun personality to help you run meetings, or even consulting with outside experts about how you can make your workplace more entertaining.

Choose the Right Kind of Delegation

In Free to Focus, CEO and productivity expert Michael Hyatt describes several kinds of delegation, each providing different levels of autonomy (and therefore responsibility) to the worker you assign those tasks to.

The strictest type of delegation only allows your worker to follow step-by-step instructions that you provide, meaning they have little to no autonomy. This is likely not appropriate for creating humor, because if you were already comfortable with comedy, you wouldn’t need to delegate this responsibility in the first place.

The next type of delegation gives your worker free rein to research an issue, and they can make suggestions if requested, but you’re still responsible for making final decisions. In this context, that might mean they come up with a number of different jokes or fun ideas, and you choose which ones to use.

Finally, the most autonomous type of delegation means that your worker can make decisions on their own, such as letting them directly edit your presentation to make it more entertaining.

Only you can decide the type of delegation that best suits your needs. However, Hyatt does emphasize the importance of clarifying exactly what you expect the other person to do and how much freedom they have in deciding how to get it done.

Making Your Workplace Fun, Rather Than Funny

Although we’ve been discussing principles of comedy and humor up to this point, Osincup makes the case that it’s often better to cultivate fun in the workplace, rather than focusing on being funny. This is because a fun environment will naturally create moments of humor and laughter. On the other hand, trying too hard to be funny can make others feel awkward and uncomfortable, and it’s often annoying as well.

To that end, the author provides some guidelines about creating a fun (not necessarily funny) work environment:

1) Make your own fun: Look for little ways to entertain yourself at work and add some levity to your workday. For example, you could get a funny calendar for your desk or imagine an amusing character reading documents to you.

2) Seek out new challenges: People love using their skills to tackle new and interesting problems. Therefore, one of the most effective ways to promote fun in the workplace is to seek out such challenges. For example, you could volunteer to take on a special project or look for opportunities to expand your role within the company. If you’re in a leadership role, think about how you could offer those challenges to your employees—perhaps by asking for suggestions about a challenge the company’s facing, or asking an experienced employee if they’d like to train a new hire.

3) Be inclusive: If you’re organizing something fun for others, whether it’s a big event or just something to enjoy while in the office, make sure that as many people as possible are able to take advantage of it. For example, organizing a bowling night for your team would exclude anyone with health conditions that prevent them from bowling. On the other hand, treating your team to dinner at a casual restaurant would be unlikely to cause any issues.

What Makes Something Fun?

Osincup offers specific tips for creating fun in the workplace, but what exactly makes a space or activity “fun” to begin with? In The Power of Fun, Catherine Price says that a truly fun experience—the type of experience that leaves you feeling energized, inspired, and happy—has three crucial components which align fairly closely with the three guidelines we just discussed.

The first component of fun is playfulness, which Price describes as a mindset of curiosity and experimentation. A playful person will try something new just to see what happens, rather than because they’re trying to accomplish a particular goal. If you’re playful, then you make your own fun, like Osincup suggests: You’re always on the lookout for something entertaining or interesting to try.

The second element of fun is flow, which describes those times when you’re completely absorbed in a task. Flow happens most readily when you’re involved in an activity that’s meaningful, enjoyable, and challenging (though not so challenging that it becomes frustrating). This matches up closely with Osincup’s second principle of seeking out new challenges or offering those challenges to your workers.

The third part of Price’s definition is connection: the feeling that you belong where you are. She says you may feel strong connections with places, pets, or even meaningful objects—however, it’s most common for a sense of belonging to emerge when you feel understood and appreciated by other people. For example, some people feel perfectly at home when they’re alone in nature, but most people enjoy a nature walk more when they have a friend or loved one along. This ties directly into Osincup’s third guideline: It’s important for as many people as possible to feel welcomed and appreciated in any attempt at workplace fun.

Consistency Is Key

Finally, Osincup argues that doing fun activities consistently is more important than which specific activities you do. Small daily, weekly, or monthly practices have a much greater impact on company culture than occasional big events. Just like family routines (such as eating dinner or watching your favorite show together) create feelings of structure, understanding, and comfort, workplace routines help employees learn what’s expected of them and cultivate a sense of belonging.

(Shortform note: Greek anthropologist Dimitris Xygalatas has spent his career studying various types of rituals, and offers one explanation for why these habitual acts or ceremonies help to build strong cultures: Rituals bring people together both literally and figuratively. Xygalatas explains that such practices often involve people dressing alike, moving and speaking in unison, and experiencing the same emotions at the same times. Those shared acts and experiences build strong connections between people, and therefore are powerful community-building tools.)

These practices could be as simple as including an amusing anecdote or picture in daily emails to your team, encouraging everyone to wear funny T-shirts on Fridays, or having a monthly theme and encouraging people to decorate their desks accordingly. Just make sure to also give employees enough free time to do so.

Osincup promises that, with time and consistent effort, you can develop both a personal mindset and an organizational culture that embraces fun, reduces stress, and supports everyone’s well-being.

(Shortform note: Fun routines in the workplace can help build a positive and healthy work culture, but they can also backfire if they come to be seen as “mandatory fun.” When employees feel obligated to participate—or, worse, if non-participation gets them branded as antisocial or “not team players”—such activities will foster resentment instead of happiness and team spirit. Therefore, it’s crucial for employees and management alike to understand that these fun routines are optional, and that nobody should feel pressured to participate if they don’t want to.)