If you haven’t defined success for yourself, someone else is probably defining it for you.
In my last article, Stop Keeping Score in Someone Else’s Game, I explored an idea that came out of several conversations about the familiar saying, “Comparison is the thief of joy.” The more I thought about it, the more I realized how often we measure ourselves against people who aren’t even playing the same game we are. Their priorities are different, their goals are different, and their definition of success might have absolutely nothing to do with ours.
Even knowing that, we often look at their scoreboard and use it to determine whether we’re winning or losing. That led me to this question: What if comparison isn’t actually the biggest problem? What if the bigger problem is that we’ve never intentionally decided what winning looks like for ourselves?
We spend an incredible amount of time working toward goals, building careers, raising families, and trying to create “successful” lives. How often, though, do we stop long enough to ask ourselves what we’re actually trying to accomplish? I’m not talking about what the world tells us we should want, or what the people around us are pursuing, but what genuinely matters to us.
How many of us are working incredibly hard to win a game we’ve never taken the time to understand?
Who Decided What Success Looks Like?
From a young age, we’re surrounded by messages about what success is supposed to look like. Do well in school, get a good job, make money, buy a house, and build your career. As we get older, the expectations shift. We start paying attention to job titles, income levels, business growth, retirement accounts, and all the other ways other people measure progress.
None of those things are bad… Many of them are worthwhile goals. The problem is that we often adopt these goals without ever stopping to ask whether they align with the life we actually want to live.
I’ve spent much of my professional life as an entrepreneur, living in a world full of scoreboards. Revenue, profitability, number of employees, number of clients… the list goes on and on. There are plenty of ways to measure whether a business is successful, and each metric has its place. They’re a necessary part of the game.
I’ve also met business owners, though, who have built incredibly successful companies, winning in all these areas, and still completely miserable. From the outside, everything looks fantastic. They’re making great money, their businesses are growing, and yet they’re exhausted, disconnected from their families, or trapped in roles they no longer enjoy. Somewhere along the way, the business they built stopped serving the life they wanted.
The Danger of an Undefined Finish Line
If you haven’t defined what your version of winning looks like, you’re essentially running a race with an undefined finish line, constantly chasing what’s next. You accomplish something you’ve been working toward, enjoy the success for a moment, and then immediately start thinking about the next goal. There’s always another opportunity, another challenge, another level you could reach. The finish line keeps moving because I never really defined where it was in the first place.
Imagine signing up for a race without knowing how far you’re supposed to run. You start running, and every time you think you’re getting close to the finish, someone tells you there’s another mile ahead. Eventually, you’d probably start wondering what you’re doing and why you’re doing it.
I think that’s how a lot of us experience success. We’re moving, working, achieving, and accumulating, but we don’t have a clear understanding of what we’re ultimately trying to create. Without that clarity, it’s incredibly difficult to experience the satisfaction that should come from making meaningful progress. We may never actually feel like we’ve arrived, which leaves us constantly striving.
Start With What Matters
So how do we begin defining success for ourselves? The answer starts with our values.
Defining our core values can sound like one of those exercises businesses go through during strategic planning sessions, where everyone sits around a table and comes up with a handful of words that eventually end up on a wall somewhere. When we do this work as individuals, working to really understand our personal values and begin using them to guide our decisions, they become incredibly powerful.
Your values establish what matters most for you, what deserves your attention, and what you’re willing to sacrifice for. They also help you identify what you’re unwilling to sacrifice, no matter how attractive an opportunity might seem.
Here’s an example. If I say my family is one of my highest priorities, that should influence how I structure my work, how I spend my evenings, and how I respond when opportunities come along that require more of my time. If I say my health matters, that should show up in the way I eat, move, sleep, and take care of myself. If I say my faith is foundational to who I am, it should influence how I treat people, make decisions, and approach the responsibilities I’ve been given.
Identifying our values is relatively easy compared to living by them. It’s one thing to say something matters… and another to consistently make decisions that show its importance. That’s where defining what winning looks like for us becomes more interesting. Once we’ve identified what matters most, we can start asking whether the life we’re building actually reflects those priorities.
The Difference Between Goals and Winning
Here’s another distinction I’ve been thinking about. There’s a difference between achieving goals and actually winning at life.
Goals are important – they give us something specific to work toward. They create direction, help us measure progress, and challenge us to grow. I have plenty of goals related to business, health, relationships, and personal development, and I don’t see that changing anytime soon. That said, we need to keep our goals in check. They are milestones… they’re not necessarily the ultimate definition of winning in our lives.
Let’s say one of my goals is to grow a business to a certain revenue level. That’s a measurable objective, and accomplishing it would be exciting, but what if reaching that goal required me to consistently neglect my family, compromise my health, or become someone I didn’t particularly like? Is that still a win?
What if I reached the goal, but along the way I built a company that required so much of my time and energy that I no longer had the freedom to enjoy the things I said mattered most? Is that winning? We can become so focused on achieving a particular outcome that we lose sight of why we wanted it in the first place.
For me, building a successful business matters, but it’s part of a much bigger life picture. I want to create meaningful work, create opportunities for others, build something valuable, and have the resources and flexibility to invest in what matters most to me, including my family. If I accomplish the financial goal but sacrifice everything else along the way, I can’t consider that success.
That insight changed my definition of winning in life. It isn’t simply about reaching my goals… it’s about reaching them in a way that aligns with the person we want to become and the life we want to live. That changes how I evaluate opportunities, make decisions, and measure progress.
What Does Your Scoreboard Look Like?
In the previous post about comparison being the thief of joy, I talked about the idea of understanding your game and figuring out how to score points. I keep coming back to that. If we know what matters most, we should be able to identify the actions and decisions that move us closer to those things. Those become the points we’re trying to accumulate.
If having a strong marriage is important, what does scoring points in that area look like? Maybe it’s spending intentional time together, stepping into some meaningful conversations, or simply being more present. If being a great parent matters, maybe it’s creating opportunities for connection, encouraging your kids, or helping them navigate the challenges they’re facing. If health is a priority, the scoreboard might include regular exercise, getting enough sleep, making better food choices, or consistently taking care of yourself.
These things can become much more intentional when we recognize them as part of our definition of success. Here’s what I find especially interesting. Many of the things that matter most in life don’t come with an obvious scoreboard. Nobody sends you a monthly report showing how you’re doing as a husband, parent, friend, or mentor. There’s no dashboard measuring how present you were with your family last week or how much encouragement you gave someone who needed it.
I’d argue that some of the most meaningful parts of our lives don’t lend themselves to easy measurement, and maybe that’s ok. Maybe we just need to get better at recognizing those wins instead of allowing the easiest things to measure to become the most important things in our lives.
Five Questions Worth Asking Yourself
If you’ve made it this far, I’d encourage you to spend a little time thinking through five questions. You don’t need to have perfect answers, and I suspect your responses will evolve as you move through different seasons of life. But I believe there’s real value in taking the time to consider them.
- What matters most to me? Not the things you feel you’re supposed to say. What relationships, responsibilities, experiences, and commitments genuinely matter to you? What would you regret neglecting if you looked back on your life 20 years from now?
- What does a successful life actually look like? Describe it without immediately defaulting to money, possessions, or professional accomplishments. Think about the kind of person you want to be, the relationships you want to have, and the impact you hope to make.
- What am I currently chasing that might not belong in my game? Are there goals, expectations, or commitments that you’ve adopted primarily because they’re important to someone else? Are you spending energy trying to achieve something that doesn’t really align with your values?
- How do I score points? What specific actions, habits, and decisions move you closer to the life you want to build? What does a win look like in your marriage, family, friendships, faith, health, and work?
- What needs to change? If you compared your current schedule, habits, and priorities to your definition of success, where would you find the biggest gaps? What’s one adjustment you could make this week that would move you closer to living according to what matters most?
These questions move the conversation beyond simply thinking about success and into what true winning looks like… and actually doing something about it. It’s one thing to have a general idea of what we value, and another thing to build a life that consistently reflects those values.
So, Are You Winning?
I want to leave you with one final thought. Imagine reaching the end of your life and looking back at everything you’ve accomplished. The career you’ve built, the money you’ve earned, the places you’ve traveled, the challenges you’ve overcome, and the goals you’ve achieved. Now imagine evaluating all of that through the lens of what matters most to you.
Would you be satisfied with the way you spent your time? Would you be proud of the relationships you invested in and the person you became? Would you feel like you made the most of the opportunities and responsibilities you were given?
Those are big questions, and it’s worth asking them now, while we still have the opportunity to make decisions that shape the answers.
Here’s what I’ve come to realize. If we never consciously define what winning looks like, we’ll probably spend much of our lives pursuing whatever definition of success happens to be in front of us. When we take the time to understand our values, establish our priorities, and define what success actually means, we give ourselves something much more meaningful to pursue.
When we’re playing our own game, the most important question isn’t whether we’re winning compared to everyone else. It’s whether you’re building a life that you’ll be glad you lived.
What next?
So we’ve defined the game we’re playing (not someone else’s) and we’ve gotten clear on what winning at our game looks like, defining our version of success. Here’s the last place I want to go in this three-part series… Let’s look at your calendar.
If you understand your game and what winning looks like, the we need to hold ourselves, specifically our calendars, accountable to activities that make winning possible. Connect with me here so you don’t miss this next blog, Your Calendar Doesn’t Lie.
– John
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What’s one of the most powerful unlocks when it comes to understanding fear and excitement? Purpose. In those moments when the two feelings rise up, purpose is often the guiding force that helps us see excitement rather than fear.
That’s why I created the Personal Purpose Guide to walk you through the same process I used myself: Reflect. Discover. Craft. Align.
Your purpose isn’t somewhere “out there.” It’s already inside you. You just need to find it—and choose to live it.
Here’s to making that a reality…
John
