The Happiness Practices with Phil Gerbyshak

It’s kind of funny when I think about it—throughout my entire career, I’ve taught people how to use tools. Tech tools, communication tools, leadership frameworks, sales systems—you name it. And while the tools keep evolving arp speed, the way I teach them hasn’t changed a bit. I teach people, not platforms. I bring a human-first approach to everything I do. Whether it's helping someone close a sale, lead a team, or troubleshoot a network issue, I instill a deep sense of humanity into the process. Because it’s never really about the tool—it’s about the person using it.That’s been true for the last 20 years. And it will be even more important in the next 20.

The world has changed a lot since I first dialed into the internet using a modem, taught others how to use Netscape, or delivered top-secret messages while serving in the Navy. And it’ll keep changing faster than ever. But one thing hasn’t changed—and won’t: People still crave real connection, clear communication, and contagious energy that lifts them up.So what’s next?I’ve spent the last few decades teaching, selling, leading, speaking, writing, coaching, and creating. Now, I’m setting my sights on the next 20 years with a clear mission, a bold vision, and a whole bunch of momentum.

🚀 My Mission: To Amplify Human Potential Through Communication, Connection, and Contagious Positivity

Whether I’m on stage, behind a mic, in a classroom, on a Substack post, or having coffee with someone who’s just trying to figure out what’s next—I’m here to light people up and help them believe in what’s possible.I do that through:- Words that move people — written, spoken, posted, or podcasted.- Tools that teach — because we don’t need more theory, we need practices that work in real life.- Moments that matter — the 15-minute break at Multnomah Falls, the compliment to a stranger, the vulnerability shared in a training room.My mission is to show up fully, share generously, and help people become the most energized, inspired, and effective version of themselves—without burning out in the process.

🔭 My Vision: To Be a Global Voice of Human-Centered Success in a Technology-Driven World

We’re entering a world of AI-generated content, remote work, automation, and hyper-productivity.Here’s what I see:- More noise, less clarity- More hustle, less heart- More tech, less humanThat’s where I come in. In the next 20 years, I’m building a body of work that helps people stay grounded, connected, and happy in a rapidly shifting world. I’ll be:- 🎙 Speaking to organizations hungry for energy, engagement, and empathy- 🧠 Training teams to thrive with less burnout and more brilliance- 📚 Writing books and articles that feel like a deep breath of clarity- 📺 Streaming content that teaches and inspires in under 10 minutes- 🧰 Creating tools to help people build practices, not just chase goals- 💡 Mentoring leaders to lead from the front—with kindness and courageBecause if we’re going to thrive in the future, we need more than just faster tech. We need better humans. That’s my jam.

🎯 What Stays the Same

There are a few constants that will continue to shape everything I do:- Written Communication — because great writing creates great thinking.- Verbal Communication — because how we say it is as important as what we say.- Public Speaking — because transformation needs a microphone.- Teaching and Training — because we’re all still learning.- Sales Enablement and Coaching — because relationships move the needle.- Emotional Intelligence — because humanity is still the most valuable skill we’ve got.I don’t just want to do this work. I want to teach others how to do it too—so they can pass it on, ripple it out, and build teams, families, and lives filled with purpose.

🌍 Legacy, Not Just Longevity

I’m not in this to go viral.I’m in this to make a dent. To build a library of wisdom. To leave behind a body of work that helps people choose connection over chaos, humanity over hustle, and purpose over performance pressure.I want people to look back at something I wrote, something I said, or something I taught and say:“That helped me. That made me feel like I could do something meaningful—and still be me.”If you’ve ever read something I shared, listened to a podcast episode, heard me speak, or even just exchanged a high-five on LinkedIn—thank you. I’m not doing this for you—I’m doing it with you.

🙌 Want to Be Part of the Next 20?

Here’s how we roll into the future together:- Subscribe to The Happiness Practices – get the tools I use and teach to stay energized and inspired- Bring me in to speak – your audience needs more fire and more heart- Start your own happiness practice – because your joy is your responsibility- Connect with me on LinkedIn – let’s build a better network of good humans doing great things- Tell someone you appreciate them today – because that stuff multiplies

Final Thought

The next 20 years of Phil Gerbyshak won’t be built on trends or tactics.They’ll be built on timeless truths and transformative practices.I’m not trying to be everything to everyone. I’m trying to be something meaningful to those who want to lead, live, and love with purpose.Let’s make the next 20 years the best, most human, most joyful years yet.Let’s go.

From the military to tech, sales to social media, and now teaching, my career path has been anything but conventional. Along the way, I’ve learned invaluable lessons that have shaped my ability to reinvent myself time and time again. Here are 10 key lessons I’ve learned throughout my journey—from Navy cryptologist to sales leader to educator—and how each experience contributed to my ongoing reinvention.

Lesson 1: Sometimes the Most Unlikely Beginnings Lead to the Most Rewarding Careers

I started my career in the Navy in 1992, where my job as a cryptologist and delivering messages by hand might not have seemed like the perfect foundation for the corporate world. But it taught me how to handle responsibility, work under pressure, and solve problems—all skills that would serve me throughout my career. From living on a Coast Guard base in the San Francisco Bay area to spending a year in Korea teaching English to a young Korean boy, I learned early on that diverse experiences can provide the foundation for something much bigger.

The lesson here? Don’t underestimate the value of seemingly unrelated experiences. Every chapter adds a layer to your skills, resilience, and perspective, even if it doesn’t immediately seem relevant to where you want to go.

Lesson 2: Be Open to Opportunities and Embrace the Learning Process

After moving to Milwaukee in 1996, I started college to become a teacher, but I didn’t stop there. I also delivered pizzas and became a peer trainer teaching faculty and students about new technology. Those experiences taught me that no matter your role, you can always learn and grow.

What I realized is that even early in your career, the opportunities you take can be just as valuable as the degree or job you’re aiming for. The key is to be open, ask questions, and be curious about everything around you.

Lesson 3: Don't Be Afraid to Take Risks—Even When It Means Leaving College

In 1998, I made a bold decision. I dropped out of college to pursue a “real job” in tech support, which eventually led to my first sales job selling high-speed internet. At the time, the internet wasn’t nearly as fast as we now think of it, and there was a lot of skepticism around the promises we made to customers. But I learned that taking risks and stepping outside my comfort zone would be necessary to continue growing.

The lesson here? Calculated risk-taking is vital to career growth. Sometimes, leaving the traditional path can open doors to opportunities that might not be on your radar otherwise.

Lesson 4: Show Up and Be Ready to Learn—Even When It’s Hard

By 2000, I had transitioned into a stockbroker role and was working on a trading team. I was also responsible for teaching others how to use our online trading platform. After 9/11, I realized that technology was my true calling, so I transitioned into IT. Within two years, I earned my first management role, and eventually worked my way up to a VP of IT position.

The key takeaway? Show up fully, be ready to learn, and always look for ways to add value. This is how you rise through the ranks and start shaping your own career trajectory.

Lesson 5: Leadership is About Stepping Up—Even When You’re Not Fully Ready

In 2003, I finished my degree in computer science and took on a leadership role. About a year later, my manager decided to leave, and I was given the opportunity to lead the team. Even though I wasn’t entirely prepared, I stepped up and said yes. That decision was pivotal in my career. It taught me that leadership often comes when you least expect it—and when it does, you need to be willing to take that leap of faith.

Sometimes, leadership isn’t about having all the answers; it’s about being willing to step up and figure it out.

Lesson 6: Your Experience and Knowledge Are Valuable—Don’t Be Afraid to Share Them

In 2005, I started my blog, sharing lessons I had learned along the way. I was reading books and consuming other blogs, and I wanted to contribute to the broader conversation. It was a humbling experience, but it also taught me that sharing your expertise—even when you're not a household name yet—can make a huge impact.

In 2007, I joined David Zinger to write the Slacker Manager blog, co-authoring content on employee engagement and leadership. This experience taught me the power of collaboration and how sharing knowledge publicly can boost your credibility and open doors.

Lesson 7: Self-Belief Is the First Step to Reinvention—Everything Else Follows

In 2010, I decided to leave my corporate job, something I had been contemplating for years. People doubted I was really going to leave, and many thought I would fail. But I printed business cards, started networking as a consultant, and landed several consulting gigs with small businesses.

The key lesson? Self-belief is the foundation of reinvention. When you believe in your ability to solve problems and create value, you can step into new opportunities, even if others doubt you or question your decisions. Your belief in yourself is what will propel you forward.

Lesson 8: Clarity of Offer is Key to Digital Leadership and Sales Success

In 2013, I worked for a Silicon Valley software company and led the social media strategy. We made three major changes to our product’s strategy within 18 months, and as a result, our product didn’t sell well. Meanwhile, a more established product with a clear, defined space in the market continued to do well.

This taught me that clarity is essential. If your audience doesn’t understand what you’re offering or why they need it, they won’t buy. A clear, consistent message is key to success in sales and leadership.

Lesson 9: Tenacity and Simplicity Are Keys to Teaching the Unbelievable

In 2015, I returned to the world of speaking and training, teaching salespeople how to leverage social media. At the time, many people were skeptical about social media as a business tool, and it was up to me to show them its value. I had to simplify complex ideas and be persistent in explaining them until others understood.

This experience reinforced the lesson that teaching something new or controversial takes tenacity, courage, and the ability to break down complex ideas into simple, actionable steps. Persistence pays off when you're teaching others to see what they can’t yet fully grasp.

Lesson 10: Flexibility and Hustle Are Essential for Navigating Life’s Unexpected Turns

In 2022, I joined Bamboo HR in Sales Enablement, but by mid-2023, we moved to Ohio, and I had to give up that role. I pivoted again, working as a substitute teacher while I looked for a full-time position in education.

What this taught me was that you have to be flexible when life throws curveballs, and you have to be willing to do whatever it takes to stay true to your goals. Whether it’s working a second job to keep things afloat or stepping into a completely different field, staying adaptable and persistent is key to navigating life’s unexpected changes.

Happiness Practices with Phil Gerbyshak is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Throughout my career, these 10 lessons have been my guiding principles. From learning to step up as a leader before I felt ready, to teaching and simplifying complex ideas, to staying adaptable and flexible, each lesson has helped me reinvent myself at different stages of my career.

The road to reinvention is rarely straight, but if you’re willing to embrace these lessons and keep moving forward, you can build a career that’s uniquely yours, no matter where you start or where life takes you next.

"A meatball sundae is messy, disgusting, and ineffective. It's the result of combining two perfectly good items that don't go well together." Seth Godin

In this conversation I had with Seth Godin back in 2008, we talked about how we can AVOID the meatball sundae, the title of and topic of a book he published 10 years ago, that is STILL relevant today. I hope you enjoy it. 

Get a copy of Meatball Sundae on Amazon, for about the price of 10 meatballs are a really good sundae. Just don't eat them together.

In a world where adulting seems to dominate every hour of the day—deadlines, responsibilities, bills—it’s easy to forget that play isn’t just for kids. But when it comes to relationships, a playful spirit might just be the secret ingredient to lasting love.

Playfulness in romance isn’t about acting childish or dodging serious conversations. It’s about injecting joy, curiosity, and spontaneity into the everyday. It’s about sharing inside jokes that make no sense to anyone else, laughing at each other’s ridiculous impressions, and building a connection that can weather the storms of life by dancing in the rain, metaphorically or literally.

What Exactly Is Playfulness in a Relationship?

Playfulness is the art of keeping things light. It’s not a rejection of maturity but rather a bold commitment to finding joy together. It might look like tickle fights in the kitchen, goofy texts in the middle of the workday, or creating absurd nicknames that only you and your partner could ever understand.

Research shows that couples who share these light-hearted moments report higher satisfaction, stronger emotional bonds, and even greater resilience in times of stress. In other words, a well-timed joke or a burst of shared silliness can be just as powerful as a heartfelt conversation.

I find in my current relationship, and in relationships in the past, the more we are laughing, the better our relationship is doing. The less laughing, things got worse or they were already bad and we just stopped trying (that’s past relationships - we are trying to play all the time in my current relationship).

The Science Says: Play Is Serious Business

Playfulness might sound like fluff, but psychologists have found that it does some heavy lifting behind the scenes in relationships.

According to several studies, playfulness strengthens emotional bonds by creating positive associations. When partners laugh and joke together, their brains release dopamine—the feel-good chemical that enhances connection and trust. It also helps defuse tension during conflict, offering a “reset” button when conversations get heated or misunderstandings pop up.

Play also opens up space for creativity in communication. When partners feel safe enough to be silly or spontaneous, they’re more likely to approach problems with an open mind and a collaborative spirit. This is critical when you’ve got kids as they present a challenge into themselves.

How to Invite More Play Into Your Relationship

So how does one actually be more playful in a relationship? It doesn’t require a clown suit or a full-time comedy routine. It just takes intention and a willingness to break out of autopilot.

Here are a few simple ways to get started:

1. Embrace the Art of the Inside Joke Every couple has their own language—those shared references, silly phrases, or code words that trigger a smile or an eye roll. Cultivate those. They create a sense of intimacy that feels like a shared secret.

2. Create Micro-Moments of Fun You don’t need to book a weekend getaway to bring in some levity. Make funny faces across the dinner table. Add a ridiculous twist to your daily routines. Challenge each other to a sock-sliding contest down the hallway. It’s the little things that add up.

3. Don’t Take the Mundane So Seriously Not everything has to be optimized, scheduled, or turned into a life lesson. Dance while doing the dishes. Narrate your errands in the voice of a sports commentator. Be willing to let go of being “normal” in favor of being fully present and absurdly joyful.

4. Reconnect With Childhood Joys Board games, old cartoons, blanket forts—there’s magic in revisiting the things you loved as a kid. Shared nostalgia not only sparks playfulness but can also lead to surprisingly meaningful conversations about who you were and who you’ve become.

5. Keep the Flirt Alive Flirting isn’t just for the early days. It’s a playful way to say, “I still choose you.” That wink across the room, the spontaneous compliment, the playful teasing—it’s all part of keeping the spark burning bright.

The Role of "Ludus Love"

Psychologists have identified a type of love known as "Ludus," which centers around play, teasing, and lighthearted flirtation. While it’s often associated with more casual relationships, elements of Ludus can be essential even in long-term partnerships. By incorporating humor, spontaneity, and a touch of the unexpected, couples can avoid the trap of predictability and keep things feeling fresh.

Playfulness, when paired with trust and emotional safety, can create a dynamic where joy becomes part of the foundation—not just a fleeting mood, but a shared value.

What Playfulness Isn’t

It’s important to clarify what playful love doesn’t mean. It’s not sarcasm at your partner’s expense. It’s not ignoring hard conversations or using jokes to avoid accountability. True playfulness comes from a place of connection, not criticism. It’s about lifting each other up, not tearing each other down under the guise of “just kidding.”

Why It Matters More Than Ever

In an age of chronic stress and over-scheduled calendars, couples often slip into routine. Days blur into weeks, and romance becomes another task to manage. But play cuts through that fog. It reminds us that love doesn’t have to be so serious all the time. That joy isn’t a luxury—it’s a necessity.

When couples laugh together, they stay connected. They remember why they chose each other in the first place. They build memories that are filled not just with milestones, but with moments—spontaneous, weird, wonderful moments that don’t need to be captured for social media to matter.

The Takeaway

Playfulness is more than a nice-to-have. It’s a relational superpower. Whether it’s through a goofy dance, a made-up game, or a shared laugh at the end of a long day, injecting a little fun into your relationship can deepen your bond, improve communication, and keep the romance alive.

So lighten up. Let go of the need to always be productive or polished. Make room for play. Because sometimes, the key to lasting love isn’t grand gestures—it’s being willing to be a little ridiculous, together.

References

Aun, Wong, (2002); Antecedents and Consequences of Adult Play in Romantic Relationships; Personal Relationships 9(3), 279-286. https://doi.org/10.1111/1475-6811.00019

Baxter, (1992); Forms and Functions of Intimate Play in Personal Relationships; Human Communication Research, 18(3), 336–363. https://doi.org/10.1111/j.1468-2958.1992.tb00556.x

Brauer, Proyer, Chick, (2021); Adult playfulness: An update on an understudied individual differences variable and its role in romantic life; Social and Personality Compass; 15(4). https://doi.org/10.1111/spc3.12589 This research paper is summarized in the article How Playfulness Improves Relationships; Psychology Today, August 15, 2024

Gold, Timmons, et al (2024); A day in the life: Couples’ everyday communication and subsequent relationship outcomes; Journal of Family Psychology, 38(3), 453–465 https://doi.org/10.1037/fam0001180 This research paper is summarized in the article How Playfulness Keeps a Romance Alive; Psychology Today, April 18, 2024.

Metz, McCarty, (2007); The “Good-Enough Sex” model for couple sexual satisfaction; Sexual and Relationship Therapy 22(3), 351–362

https://doi.org/10.1080/14681990601013492 Proyer, Ruch, (2011); The virtuousness of adult playfulness: the relation of playfulness with strengths of character; Psychology of Well-Being 1(4). https://doi.org/10.1186/2211-1522-1-4

"The Best Present is Your Full Presence" argues that giving someone complete and undivided attention is a powerful and often overlooked ability. The author posits that in a world filled with distractions, intentional presence communicates value and can positively impact relationships and well-being. By silencing distractions and focusing fully on the present moment, individuals can reduce burnout, build trust, increase happiness, and become more effective in various roles. Ultimately, the text champions presence as a valuable gift that requires conscious effort but yields significant positive results in personal and professional interactions.

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This week’s article, "5 Simple Ways to Be Happier at Work This Week," presents practical strategies for enhancing workplace satisfaction.

I suggest small, actionable steps that individuals can implement immediately. These hacks include starting the day with a small accomplishment, connecting with colleagues, taking brief "joy breaks," focusing on progress over perfection, and identifying moments of meaning. I emphasize that consistent practice of these habits can lead to a more joyful and productive work experience. The article encourages readers to proactively cultivate happiness rather than viewing it as an elusive outcome. Ultimately, it frames workplace happiness as a series of conscious choices and small, positive actions.

Almost 20 years ago I wrote a book called 10 Ways To Make It Great!, about some of the things you could do to take control of your life and create (make) the life you were living (it) better (great). The title of the book came from the 10 chapters and this idea - and naturally, I included one additional chapter about going the extra mile, because why the heck not?

Anyway, I decided to upload the book to Google Notebook LM and see what it would create for an audio excerpt of the book. It turned out pretty good, if I do say so myself.

Here’s what Google Notebook LM had to say about what it created:

This collection of excerpts from Phil Gerbyshak's book, "10 Ways to Make It Great!", offers practical advice and actionable steps for personal and professional growth. Gerbyshak encourages readers to take control of their lives and make choices that lead to greatness rather than simply having a "nice" day. The text covers diverse topics including self-discovery through assessments, utilizing the 80/20 rule for increased effectiveness, the importance of continuous learning through reading and other methods, and building strong relationships. The author also emphasizes the significance of recharging and reflecting, finishing what you start, and consistently going the extra mile to achieve goals and make a positive impact.

I hope you enjoy it. And you’re welcome to buy 10 Ways to Make It Great! on Amazon if you want the full version.

I’m testing out creating an AI audio version (9:19 in length) on Wednesday of my Monday article for you so you can get another take on what I’m writing about, or to enjoy in a different way in case you prefer audio to text.

Let me know what you think as I’ll be continuing this for a while until I get enough feedback or until I determine it’s not useful.

This week is Seizenso, the funeral while you’re still alive. I hope you enjoy it.

Happiness Practices with Phil Gerbyshak is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Market volatility. Sustainability demands. Hybrid working. Opportunities and hazards of fast-changing technology and regulations. Companies and nonprofits face more daunting challenges than ever. How can we collaborate in our organizations—and with outside partners—to solve problems, innovate, and succeed?

The new book, Smarter Collaboration: A New Approach to Breaking Down Barriers and Transforming Work, offers groundbreaking solutions. 

Join us for a conversation with Dr. Heidi K. Gardner as we talk about the insights from this book and much more!

In a recent conversation between Michelle D’Atillo of Sōsh and yours truly, Phil Gerbyshak, we talked about resilience: how to be more resilient and what to do when it all goes sideways, so you can strengthen that resilience muscle.

With permission, I’m sharing the conversation from the Get Sosh Social Soup podcast with you in its entirety. I hope you enjoy it and it helps you in your happiness practice.