It’s funny how often we chase “success” without ever stopping to think about what it really means to us, right? We might repeat motivational slogans or flip through countless self-development books, but how often do we pause to ask ourselves: “How do I define success—on my own terms?”
Back when I was in digital marketing, I spent years striving for external markers: promotions, raises, bigger clients. Later, as a freelancer (and now here at DM News), I realized I’d never really considered if those conventional benchmarks made me feel genuinely successful—or if they were just expectations I absorbed from everyone around me.
Success is personal. It’s shaped by our unique experiences, passions, and goals. If you’re not sure where to start, here are five questions I’ve found especially helpful in my own journey toward defining success in a way that truly resonates.
Let’s dive in.
1. What would a good week/day look like?
It can be overwhelming to plan out your entire life in one sitting. I’ve definitely had moments where I tried to envision every detail—where I’d live, what my relationships would look like, how big my savings account would be. It felt like trying to juggle a thousand different things at once.
For me, a more realistic place to start is with your smaller units of time: months, weeks, or even days. After all, our lives are made up of a collection of these smaller segments.
When I first went freelance, I was borderline obsessed with mapping out the next ten years. I had visions of traveling the world, working from chic cafes, and achieving some elusive level of “freedom.” But I quickly learned that focusing on the day-to-day was far more tangible—and far more motivating.
So, consider this: what does a good day look like to you? Is it spending a few hours on meaningful work without distractions? Taking an hour to exercise? Having dinner with close friends or family? Reading a book you’ve been meaning to dive into?
Similarly, think about what a good week would involve. Would you schedule enough downtime to recharge, or dedicate certain days solely to creative projects?
In defining success, your vision of a good day or week can serve as a compass. Once you understand those daily or weekly goals, you’ll have a more concrete sense of what success might look like for you over the long haul.
2. What would you do if money were no object?
I came across this question from the late British philosopher Alan Watts, who challenged his students to think beyond mere financial security. It’s a question that has followed me around since: “What would I be doing if I wasn’t worried about paying bills?”
It’s not about ignoring reality. We all need to pay rent, buy groceries, and manage our finances.
But this question forces you to peel back the layers of your current lifestyle. It asks you to imagine a scenario where financial limitations don’t exist. When you do that, what emerges? Is it a shift from your current job toward a passion project you’ve always wanted to pursue? Or maybe you’d embrace more time for family or philanthropic work?
Back when I was juggling client projects in digital marketing, I asked myself this question. The answer involved writing about the psychology behind daily decisions—something I was drawn to but never fully pursued because it didn’t seem like the “profitable” choice at the time. Eventually, I realized how important it was to lean into that passion, even if it meant taking a leap of faith.
Your answer to “What would I do if money were no object?” might point you toward a unique version of success—one shaped by genuine interest, curiosity, and joy rather than just a paycheck.
3. What actually makes you feel fulfilled?
It’s easy to get sucked into advertising, social media, and the seemingly endless chatter about what it means to be successful. Luxury cars, designer wardrobes, flashy vacations—all those shiny images can leave you feeling that true success must align with them in some way.
But take a moment and think: what truly fills you up on a deeper level? Is it having more free time to spend with people you care about? Contributing to a bigger mission or cause? Learning new skills and continuing to push the boundaries of your abilities?
For instance, I once thought landing high-profile corporate clients was the ultimate professional milestone. But after working 60-hour weeks, I found that the frantic pace wasn’t fulfilling.
Sure, I was earning a decent income, but I felt drained. Over time, I discovered that having a schedule that allows me to write thoughtfully—and still get outside for a hike along the California coast—brings genuine contentment.
As Greg McKeown has said, “If you don’t prioritize your life, someone else will.” That quote hit me hard when I first stumbled on it. If you’re not clear on what genuinely fulfills you, it’s easy to chase success on someone else’s terms. Asking yourself this question can help you zero in on what truly nourishes you from the inside out.
4. Who do you truly want to impact?
I’ve mentioned this before in a previous post, but it’s worth repeating: success is rarely a solo sport.
We might imagine ourselves scaling mountains alone, but real, lasting satisfaction often involves the positive effect we have on other people—our families, friends, colleagues, community, or even a global audience.
Ask yourself: who do you want to serve, help, or inspire? It might be your immediate circle, or it might be people around the world who share a similar struggle or dream.
Your definition of success might hinge on making a tangible difference to their lives. Figuring this out can provide immense clarity. Once you know who matters most in your success story, you’ll find you’re far less swayed by irrelevant opinions or passing trends.
5. What do you want to say on your deathbed?
So this one might sound a bit intense (maybe even a little morbid), but honestly, it’s helped me—and it might help you too.
When everything is said and done, and you’re looking back at your life, what do you hope you’ll be able to say? What experiences, relationships, contributions, or adventures will you be most proud of?
I started asking myself this after a late-night conversation with a mentor, who once said, “You don’t want to wake up one day realizing you lived someone else’s dream.” That stuck with me. It pushed me to think less about immediate wins and more about the long game—about building a life I’d be proud to look back on.
Maybe you want to say you stayed true to your values. Maybe you want to say you showed up for your family. Maybe you want to say you took the risks that mattered.
Whatever it is, this question can act as a powerful filter: it reminds you to focus on what’s really important, not just what’s urgent or flashy.
It’s not an easy question, but if you can answer this honestly, it’ll give you a strong, grounded sense of what success means to you—not just today, but for a lifetime.
Putting it all together
Defining success on your own terms isn’t a one-time thing—it’s an ongoing conversation with yourself. Your answers to these questions might shift as you grow, learn, and experience new chapters of life. And that’s a good thing.
The important part is that you’re asking them. You’re taking the time to step off the treadmill of default expectations and tune into what really matters to you. Because at the end of the day, success isn’t about checking off someone else’s boxes—it’s about living a life that feels right, meaningful, and true to who you are.
So take a breath. Get curious. And start defining success in a way that’s entirely, unapologetically yours.
