Whimsical Wellness: Channelling Our Inner Child 👶

Time machine to Sam circa 2002: a keen affinity to playful poses

From the clickety-clack of a Lego tower snapping perfectly into place, to the fresh evergreen scent of scaling Vancouver cedar trees, play has been a formative part of my personality and self-concept. Through my days of random frolicking in sandboxes and seesaws, I’ve realized that adopting play into all aspects of life is a happiness hack. Even today, my commitment to the art of improv comedy grounds me in feelings of openness, spontaneity, and joy against a busy backdrop of business life.

While my own lived experiences are not exclusive, the concept of play falls out of fashion as we mature into a world of responsibilities. The transition from childhood to adulthood often erodes our sense of curiosity and wonder in favour of productivity and momentum. The shift from playfulness to mindfulness naturally takes shape as life stressors take over, leading us to crave mental stability over free-flowing fantasy.

As mainstream mindfulness boasts substantial benefits through routines that help us reset and relax, recent literature suggests they are not a one-stop-shop to optimizing wellness. Modern methods like meditation and reflections have been commodified and are treated as a magical panacea for life’s ailments, perhaps to a fever pitch.

Revisiting and reframing play as a wellness mechanism may be an authentic antidote to our mental and emotional health. This claim gives rise to a key question: How might we incorporate ‘play’ in practical ways to build towards a mindful and happy life?

To address this pressing prompt, I’ve developed a framework around a new concept I have coined: whimsical wellness. This model combines scientific theory and personal experiments to achieve one simple outcome: inviting moments of play to enhance your mental and emotional health. I’ll also examine the impact of contemporary “fun-first” digital solutions that embrace a layer of whimsicality in their UX. Let’s start playing!

Today’s delicious nutritious content menu

🧠 I. The Philosophy of Practical Play

To prime our deep dive into the whimsical wellness framework, we need to first understand how the premise of play has evolved over the years. Superficial coverage of this topic has been pervasive in mass media outlets, so I wanted to take a scholarly spin and unearth as many peculiarities from the datasets as possible.

Understanding the Progression of Play

In recent years, other non-profit organizations such as the National Institute for Play (NIFP) and the US Play Coalition have attempted to codify and democratize the values of play for all. While these initiatives provided the groundwork for credible conversations, they lacked the staying power to scale the messaging to play-deprived masses in corporate America. The problem is compounded when we benchmark against the research-heavy mindfulness movement, which tends to do a better job persuading and enticing skeptics through detailed data points.

I think the root issue driving the rejection of play is a lack of accessible and tangible methods to even get started. This is particularly problematic when we consider that very few are raving about play in our social circles. The founder of Ness Labs’, a virtual gym for the mind, presents the playfulness as a practice (PaaP) system. She argues there are two broad channels to kickstart this process:

  • Direct play: Specific activities such as live-action games and stimulating exercises to provoke exploration, discovery, and creativity.
  • Indirect play: Playful reframing of situations such as through imagination, improvisation, and pleasure in learning and knowledge-seeking.

With this bimodal lens, it becomes easier to appreciate how having options helps alleviate the pressure of “force-fitting” play into our lives. We often talk about mapping and measuring life at both a personal and professional level, but I argue that a choose-your-own-adventure approach at a playful level helps us stay more present.

The fact that a simple reframe of unassuming everyday events can help stoke our child-like curiosity is already a significant babystep in cultivating a healthy mind.

Considering Gamification

At the mass market level, data-driven gamification has been tested at great lengths throughout the years to simulate playful energy in consumer applications. In this case, we embed the touch and feel of games directly into our workflows, indirectly bringing us one step closer to a free-form playful nirvana.

Unfortunately, the main limitation of traditional gamification is that its primary goal is not to encourage play for the sake of the act itself. By design, to “gamify” is to imbue an experience, task, or activity with just enough of a playful element to drive broader goal-oriented outcomes. For example, Robinhood’s animated, socially-oriented user interface breaks the barriers of public market investing. Calm’s daily short-form meditations and sleep stories pull in game-like repetition to make mindfulness more accessible. And TikTok’s content creation engine feeds on attractive pop culture trends, as users embrace song, dance, and play as forms of social proof. All of these high-growth products have compelling value propositions, but the jury is still out whether they help foster a sustainable practice of play for the long-term.

While gamification provides a fractionalized version of play, proactive and consistent efforts to embody a whimsical mood are key to improve wellness.

Applying the Scientific Method

To my surprise, further discovery suggests that there have been decades of in-depth systematic studies on how play interfaces with prescriptive wellness and happiness outcomes. Laura Richardson, an industry design leader, developed The Periodic Table of Playto characterize all the unique channels that birth opportunities to play:

Exhibit 1. The architecture of play at the molecular level

While the model was initially applied primarily to children, we can extract these building blocks and extrapolate them to fit our personal circumstances. Taking the model persona of an ambitious, early-career, time-starved tech professional, we see glimpses where these elements organically (albeit erratically) enter — hacking together side projects with no-code tools, experimenting with productivity hacks, or joining an online fellowship. Through our persona, the underlying disconnect we uncover is viewing these activities solely for advancement and ambition, forgetting the exhilaration and enjoyment of the activity itself.

It’s funny how the widely-used tech vernacular holds so many close parallels to the vocabulary of play. Just as chemical elements are commonplace in both the DNA of humans and nature, it’s really reassuring to me that the periodic table of play is equally as pervasive. Creativity is our source of oxygen. Imagination becomes the equivalent of hydrogen, while improvisation acts as the carbon link to constantly generate more nourishing byproducts — playful ideas. Aside from the geeky chemistry comparisons, I think the most important takeaway from the science of play is just one simple truth:

Play still exists in many different forms as adults, even if we don’t recognize it.

🧪 II. The Elements of Whimsical Wellness

Bernie DeKoven, the author of A Playful Path, suggests that while defining “play” can be a nebulous task, there is one concept that is closely associated: rules. He drafts out four potential drivers that blend play and rules together: rule-seeking, rule-breaking, rule-making, and rule-changing.

I think this view of reconfiguring rules creates a pipeline of emergent perspectives, cognitive tools, and wellness enhancements as we adopt the classic tech mentality of moving fast and breaking things. My revised philosophy of play seeks to overwrite the rigid rulebook that binds us too tightly to the reality of recurring routines. Doing so replaces painful drudgery with a greater probability for high-impact discovery.

In order to convert the theoretical literature into more tangible, actionable wellness practices, I have constructed a custom mental model that leverages Richardson’s periodic table elements with DeKoven’s rule-based principles to alchemize into a personal “Playful Playbook”:

Exhibit 2. Playful Playbook: systematizing ways to live whimsically

My business school teachers would be proud to see me blend and graph all the atomic components together using the ubiquitous 2x2 matrix. I saw a way to integrate greater flexibility into this model by accommodating different personalities, with a bias for action measure on the y-axis and a risk tolerance scale on the x-axis. The outcome is that each quadrant represents a distinct orientation of a play strategy:

  • Rule-Seeking: For those who like to stick to the essentials, this strategy has the lowest barrier-to-entry and minimal friction to our standard workflows. The most important consideration is to explicitly carve out space for these pastimes, so they can be rebranded as true moments of pleasure over productivity.
  • Rule-Changing: For those who have a higher risk tolerance and want to tinker with new passion projects, constructing personal quests or challenges can be a super useful way to morph and stretch ideas. I make this approach meaningful through writing, exploring environments in-depth, and capturing life moments.
  • Rule-Breaking: For those who seek opportunities for creative destruction, rule-breaking is an exciting method to actively go against the grain. For business and tech types, I find that sprinkling in artistic activities helps activate the less-exercised parts of our brain. Painting, acting, and sculpting are all fun favourites.
  • Rule-Making: For those who enjoy pushing the boundaries and characterize themselves as creators or entrepreneurs, the rule-making quadrant is likely the most fulfilling. As we grow older and develop a greater awareness of what energizes us, becoming a builder inherently incorporates play into the mix.

To experiment with my own framework, I initiated a week-long regimen. To make the exercise more formal yet retain a high degree of fun I branded each of these principles as “playfulness interventions”. These were positioned as evening rituals to incentivize greater consistency and to not majorly interfere with my daily work rhythm. You could even think of these tactics as soothing self-therapy techniques!

Exhibit 3. My personal pathway in weekly experiment form

Digging a bit deeper into my process, there are three patterns of activity that emerged from my documentation process, representing a surprising yet refreshing outcome:

  • Reflecting on playful things that happened that day with the associated people and feelings
  • Recording how playfulness was used in new ways throughout the day
  • Recalling how many times something “playful” occurred during the day

By placing play at the forefront, I re-gained the comfort and confidence of a curious child. How could I tell? Maybe an ephemeral sensation, but I felt at ease, at peace, fully whimsical despite all the external chaos within the week. The silver lining to tapping into the Playful Playbook is that actions taken do not have to be any less productive than activities we normally associate as value-adding or growth-oriented. Knowing this, I can distill down this new framework into three core tenets:

Whimsical wellness is a worldview engineered to empower and inspire.

Whimsical wellness is unintrusive in structure and unlimited in possibility.

Whimsical wellness is a new sort of mental insulation against the suffocating heat of day-to-day anxieties and agitations

📱 III. Whimsicality in the Wild

While our framework shows being whimsical is largely accessible within our immediate surroundings, many new ventures are also piloting unique solutions that incorporate elements of play. I’m confident that these inventive products can shift gamification from a gimmick to a viable tool for both pleasure and personal care.

🧩 Childlike Concepts — “Experiment In Public”

Play typically involves tactile and interactive elements, introduced when children gain the motor skills to touch and feel things. By extending this to broader tech use cases, the following products reimagine conventional wisdom in clever, differentiated ways:

Exhibit 4. Welcoming a playful era of consumer apps
  • Monet: This platform refreshes the long-lasting dating app concept through the construction and sharing of drawings to find romantic love and platonic friendships.
  • The Landing: This social design platform expands the Pinterest feel of shareable moodboards and encourages users to digitize their home furnishing decisions.
  • Playne: This virtual game environment aims to build meditation habits through a world-building premise — the more you meditate, the more the landscape expands.

🌳 Digital Immersions — “Find Your Flow”

When we play, we interact with an environment. As play sessions derive their value through being exploratory and experiential, the following web applications transport the user to a completely separate universe filled with open possibilities and heightened sensations. I find myself gravitating towards these platforms as a way to combat my autopilot internet browsing mode and reinstate a sense of flow!

Exhibit 5. Immersing in new-age nature concepts
  • Tree.fm: This soothing app centers around nature escapism, providing a spontaneous soundscape that helps us appreciate our physical world and offers a wellness refresh. My favourite way to traverse nature in a digital setting.
  • A Soft Murmur: This web experience leverages the toggling of ambient sounds to transport the user into any nature-based terrain. Custom realities are realized and remixed to tackle mental stress in life and facilitate flow state in work.
  • Weavesilk: This simple interface situates the user on a dark screen and equips them with freeform silk threads — an “interactive generative art” activity. One of the most unique wellness boosters and creativity enhancers that I’ve seen!

👥 World Builders — “Connect With Others”

Play often involves the participation of several hearts and souls, facilitating the ability to connect with ourselves, others, and our community. With the advent of digital gathering grounds that supersede static Zoom rooms, these solutions manifest the feeling of peer intimacy. Try these platforms in your next cross-functional group event!

Exhibit 6. Expanding social and professional playgrounds
  • Gather.town: With a recent $26M Series A from Sequoia Capital, Gather represents the new-age approach to hosting group occasions (weddings, conventions, office hours) and providing serendipitous spaces for lighthearted social interactions.
  • Mozilla Hubs: Unlike Gather, the Hubs platform avatarizes the experience through 3D models, private virtual meeting rooms, and natural media sharing extensions, all through a playful level-editor called Spoke.
  • Topia: Similar to Gather, this solution builds on the spatial audio and video capabilities to simulate the characteristics of real-time in-person connection. With pure customization and an artistic focus, the app incentivizes having fun.

The common thread that links all of these applications together is the willingness of the creators to orchestrate experiences that place child-like whimsicality at the core. By truly prioritizing design and development efforts around a central playful mission, there is minimal separation away from the pure leisure and imagination these tools aim to maximize.

💡 Epilogue: The Powerful Potential of Playfulness

Mixing elements of whimsical, wonder, and wander into the DNA of budding tech products and our everyday decision calculus can result in countless benefits. By resisting the temptation to apply conventional mindfulness as a plug for all mental health issues, we unlock a timeless technique that transcends age and experience. Summarized in a quick mantra that I just made up but which probably exists on some deep motivational quote moodboard: To play is to live, to live is to play.

Reflecting on the connection to new-age technology, I love how digital user experience stalwart Marek Pawlowski frames the idea of whimsical product outcomes:

There is a rare moment where people’s relationship with a product or service evolves to take on new meaning. The orbit of their behaviour becomes eccentric, no longer solely derived from the purpose of the original creation, but rather possessing gravitational force of their own.

If we view our adult lives as one long infinite game where winning is not the core intent, then the most important principle is to keep showing up and playing. Beyond maintaining our well-being at tip-top shape, I believe play is the ultimate driver for churning continued creativity — a one-way ticket to developing a kaleidoscope mind.

It turns out being “childish” as an adult is cool after all. 😎

Till our next playdate,




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Sam Wong

Sam Wong


Aspiring product manager, armchair philosopher, and avid improv comedian. https://samwong.co