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Success is a word that carries so much weight. From the time we’re young, we’re taught that success looks a certain way—climbing the corporate ladder, earning a steady paycheck, getting married, having kids, buying a house, and securing a retirement plan. It’s a checklist that’s been laid out for us before we even have a chance to ask ourselves: What does success actually mean to me?
For years, I chased a version of success that wasn’t fully mine. I spent time building a career in digital media, working my way up until I landed my first director role. On paper, it looked like I had made it. I had the title, the salary, the external validation—and don’t get me wrong; this had been my dream since seeing Sidney Shaw in Brown Sugar in the early 2000s. But something was missing. Deep down, I knew I wanted more—not in the sense of a bigger paycheck or a fancier job, but more alignment, more freedom, and more purpose.
Still, the idea of stepping away from that structure was terrifying. What would people think? How would my family react? I wrestled with those questions for a long time before I finally left my corporate 9-to-5 to start my own wellness business and focus on freelancing on my own terms. And let me tell you—society does not make it easy for us to take that leap.
As a queer Black woman, I already knew what it was like to navigate spaces that weren’t built for me. The pressure to “succeed” in a way that felt familiar and acceptable to those around me was even heavier because, for so many of us, stability isn’t just a personal desire—it’s a survival tool. When you come from communities where financial security has historically been precarious—due to employment discrimination, wealth disparities, generational barriers, job insecurity, workplace bias, structural inequities, you name it—choosing an unconventional path can feel like an unnecessary risk. But I knew in my spirit that I couldn’t keep living for other people’s expectations. I had to make a choice: follow the script or carve my own path.
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One of the hardest parts of redefining success is dealing with other people’s perceptions. There are members of my family who still see me as someone who just quit work and chose to be “unemployed.” They don’t see the multiple deadlines I work against each month as a freelance writer. They don’t see the long hours I put into running my own business, managing my website, maintaining my newsletter, marketing myself on social media, and creating YouTube content to build my presence. They don’t see the collaborations I nurture with other practitioners, the constant self-education, or the energy it takes to carve out a sustainable livelihood in the wellness space.
To them, success is tangible—it’s a paycheck, a stable job, and a routine they understand. And because I don’t fit into that mold anymore, my work is often dismissed or misunderstood. I work from home, which doesn’t help disprove their narrative. But the truth is, entrepreneurship is not for the faint of heart. It requires resilience, adaptability, and a deep commitment to something bigger than financial security. The challenges are real—financial instability, self-doubt, and navigating an uncertain path while still trying to take care of my mental health. But at the end of the day, I know I’m walking a path that’s true to me.
Unlearning Society’s Definition of Success
If you’ve ever felt stuck between external expectations and your own vision for your life, you’re not alone. Letting go of what society deems “successful” isn’t easy, but it’s necessary if we want to live authentically. Here’s what I’ve learned in my journey of redefining success:
1. Give Yourself Permission To Want Something Different
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We don’t have to follow the blueprint that was handed to us. The first step in redefining success is giving yourself permission to step outside of the expected path. That might mean pursuing a creative career, prioritizing rest over hustle culture, or choosing a lifestyle that values freedom over stability. There’s no one way to build a meaningful life.
2. Redefine Your Metrics for Success
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Instead of measuring success by how much money I make or how many clients I have, I’ve learned to measure it by impact and alignment. Am I doing work that feels fulfilling? Am I growing? Am I using my gifts in a way that feels meaningful? Shifting the focus from external validation to internal fulfillment changes everything.
3. Accept That Some People Won’t Understand—And That’s Okay
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Not everyone will get it, and that’s fine. Some people are deeply attached to traditional definitions of success, and your choices may challenge their worldview. But their inability to understand your path doesn’t make it any less valid. At the end of the day, you are the one living your life—not them.
4. Find Community in Like-Minded People
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When you step off the conventional path, it can feel isolating—especially when people around you don’t understand. That’s why it’s so important to surround yourself with people who do get it. Connecting with other entrepreneurs, creatives, and unconventional thinkers has helped me stay grounded in my decision. Whether it’s through online communities, networking spaces, or personal friendships, finding people who support and uplift you is invaluable.
5. Honor Your Own Timeline
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One of the hardest lessons I’ve learned is that success isn’t about reaching a particular milestone by a certain age or keeping up with anyone else’s timeline. Some seasons are about building, some are about learning, and some are about simply surviving. Just because you’re not seeing immediate results doesn’t mean you’re not moving forward. The work you put in now—whether seen or unseen—is laying the foundation for something greater.
The Freedom in Defining Your Success
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Despite the challenges, I wouldn’t trade this path for anything. The freedom to build something on my own terms, to pour my energy into work that feels meaningful, to wake up every day knowing I’m walking in alignment with my values—that, to me, is success. It’s not about checking off society’s boxes; it’s about creating a life that feels whole, authentic, and fulfilling.
So if you’re feeling the tension between external expectations and your personal truth, I encourage you to pause and ask yourself: What does success mean to me? And once you have that answer, hold onto it—because that definition is yours to claim, shape, and live by.
Steph R. Long is a Chopra-certified Ayurvedic health educator, meditation instructor, and well-being coach. She’s also the founder of holistic wellness and coaching practice SRL Well-Being and the former Deputy Director of Enterprise for Refinery29 Unbothered, where she oversaw health, wellness, and spirituality content. For more wellness insights, follow her on Instagram and YouTube, and subscribe to her podcast.
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