Here’s What I Think a Good Life Actually Looks Like

A nice house, money in the bank, a good-looking partner, and career wins are great—but I’ve learned that they don’t actually make me that happy. Here’s what does.

Photo by ROSSER / LEBEAU

People say the “American Dream” is dead. It feels pretty old-school to even talk about it. But that doesn’t change the fact that we’ve all been taught to chase certain markers of a good life: Millions of dollars in the bank. An attractive partner. A beautiful home. A fancy job title. 

I’ve been very fortunate in this lifetime to be living the classic American Dream (or in my case, a Canadian living the American Dream). I have made millions, I have a beautiful wife and a nice house, I’ve made ‘an impact’ and I’ve sold a company. This is what many people are working towards; a North Star of what we’ve been told will make us happy. 

As someone who has played the game and gotten the things, I’m here to tell you that I don’t think these should be our goalposts for a good life. From my own vantage point of having attained the things that so many people are striving towards, I’m here to plant a stake in the ground and offer my humble view of what those goalposts should be—and what actually makes a good life.

Before you dismiss this post as a thinly veiled humble brag, I will be the first to tell you that I have gotten a lot wrong. Over the years, I certainly haven’t been the happiest or most alive guy. My wife and I really struggled to enjoy our relationship for the first four years we were together (I’m proud to report that we have been more or less crushing it for a solid 1.5 years now!). I haven’t always been great at managing my energy and I’ve dealt with various illnesses and ailments. I’ve been tightly gripped and stressed when there isn’t much reason to be. I have complained to my friends a lot. And the list goes on.

Over the last year, however, and especially the last few months, I’ve really felt that I’m living a great life. I’ve finally found a flow where I feel content and happy much of the time. I feel connected. I feel alive. My relationships are in great places.

Why am I sharing this? My intention is simple: I’m just a guy who’s had his fair share of struggles trying to experience peace and joy in this life. I think I’ve finally discovered what actually works for me, so I’d like to share it. 

*Drum Roll Please* 

Here’s my take on what a good life means for me:

• A loving and secure connection with a partner/spouse

• A connection to spirit/God/nature/creator (or whatever name you want to use)

• A sense of belonging to a community that interests me

• Loving and secure connections with close friends

• Good health and enjoying moving my body

• Learning and growing

• A loving connection with my family

• A connection to nature and animals 

• A sense of purpose (knowing that I’m spending my days doing something I enjoy that benefits others)

That’s my list. It’s pretty simple, and as you can see, it’s significantly more connection-based than goal-based.

How did I realize this? I became curious about my own happiness, and I began to tune my awareness into what was working and not working for me. Let’s consider travel. My wife Jane and I have been on some really nice luxury travel experiences. And for me, the amount of luxury or how nice the area is has very little to do with my enjoyment. What majorly moved the needle was how connected I felt on these trips. How connected was I to the people I was traveling with? How connected to myself? How connected to Jane? Time and time again, the main indicator of whether we would enjoy a trip was the amount of connection we experienced. 

Looking into my own unhappiness provided another major clue. If I were to create a formula for what makes me miserable, it would be pretty straightforward: Just make sure I’m alone, preferably with a screen in front of me all day, and a gigantic, never-ending to-do list. If that trifecta is in place, you can be pretty sure I won’t be enjoying myself. 

What’s the antidote? For me personally, counteracting excessive busyness and screen time with wellness practices like exercise and meditation doesn’t cut it. Instead, I need to have meaningful, in-person conversations regularly. When I have at least one (preferably two or three a day), I feel joyful and alive. I’ve also noticed that simply taking the dog for a walk and striking up a conversation with whoever I pass in the park makes a big difference for me. Again, it all comes back to connection. 

I’m not going to pretend that having a big house or a beautiful partner isn’t a nice thing to have. But I can tell you that it is possible to have a beautiful house and partner and be perfectly miserable. My wife’s beauty has not wavered in the 5+ years that I’ve been with her, and we’ve had both happy times and unhappy times. Clearly, her appearance wasn’t what was making me happy. It was the secure, loving connection we’ve built through dedication, persistence, and a consistent commitment to honest communication. 

The Upshot 

While these are just my reflections, based on my coaching work, there’s an important and more universal conclusion to be drawn here. 

When a normally high-functioning client comes to me in a time of deep stress or unhappiness, there’s usually one thing going on: a breakdown in connection. It might come in disguise, but there is almost always a relational problem at the core of their unhappiness. 

A working relationship may not be where it needs to be. A tough conversation needs to be had. Feedback needs to be delivered. A conflict needs to be resolved. They are experiencing a lack of flow in connection. If I’m able to support them in “un-kinking” the hose, the connection flows again and they are able to experience more peace, joy, and aliveness. Even though all my clients have big goals and missions they are trying to live into, it’s often a connection-based challenge that they bring to our coaching sessions.

At this point, I might as well brand myself the ‘connection guy’. I’ve written about Relational Abundance, the idea that our lives are mainly enriched by powerful connections with others. I’ve written about how big things get done through a combination of focus and personal relationships. I’ve made the case for interpersonal growth as the inner work we actually need to improve ourselves and our lives, rather than more traditional forms of “personal growth” like meditation retreats, psychedelic journeys, and self-focused therapy and coaching. I’ve written about the importance of being a physically social being. 

Every day, I coach my clients to become the best versions of themselves and live the best lives they can possibly live by focusing on enhancing connection. And it’s a constant reminder for me of what really matters—and what happiness and success truly look like.  

To wrap it up: If you want to enjoy life, if you want to experience more aliveness, if you want to make more money, if you want to get big things done, if you want to have a great marriage, if you want to build a beautiful loving family, if you want to have a great community, the path is clear. We must focus on cultivating connection and living a lifestyle that orients towards connecting with others in meaningful ways. This leads us more in the direction of living in a neighborhood where neighbors connect, instead of being separated by a long driveway with a gate. It means getting involved in your community in whatever way you can. It means “making the first move” and putting yourself out there in many social interactions. Not being afraid to strike up conversations with people you encounter in your daily life. It means having the courage to work on and improve the relationships that are most important to you. It means resisting the pull to isolate yourself at your house behind a screen.

I’d love to hear from you: What does a good life look like for you? Dig deeper here: Is it connection or attainment-based—or something else entirely? What is something you can change today to nurture the important connections in your life?