Many independent professionals eventually reach the milestone they once dreamed of. The pipeline is full, income is stable, and their reputation precedes them. They've "made it" by every external measure - yet something feels off. The success they worked toward doesn't deliver the satisfaction they expected.
This paradox was the focus of a recent Outsized fireside chat featuring Anurag Bhalla, CEO and co-founder of Outsized, and Will Finn, General Counsel at ONE Championship and researcher at the School of Positive Psychology. Both speakers have spent years working with high achievers: Anurag supporting thousands of independents across global markets, and Will in his legal career and academic work on purpose and meaning.
Their conversation unpacked why fulfilment often escapes those who look successful on paper, how to distinguish between burnout and misalignment, and what it means to define success in a sustainable, purposeful way.
The statistics tell a sobering story: Gallup research consistently shows that 50-60% of professionals feel disengaged at work, regardless of achievement level. For independents, this disconnect can feel particularly jarring because they've specifically chosen their path and clients.
"I hear this constantly in our community one-on-ones," Anurag explains. "People have strong delivery records, good client relationships, solid income - but they still feel stuck. They achieved what they thought would make them happy, and now they're questioning what's next."
Will offers a psychological perspective: "This isn't a new phenomenon, but it's surfacing much earlier in careers now. Previous generations might have waited until their forties or fifties to ask these questions. Younger professionals don't want to wait decades before finding joy in their work."
The success paradox reveals something fundamental about human psychology. Achievement creates stability, which provides mental space for deeper existential questions. When survival needs are met, we naturally begin examining whether our work aligns with our values and sense of purpose.
Is pursuing purpose a luxury or essential to long-term success?
Historically, purpose was considered a "midlife crisis" problem - something you worried about after establishing your career. Today's professionals approach it differently. "Purpose-seeking is both a privilege and a universal need," Will observes. "It's a privilege because it only becomes possible once basic survival is secure. But it's also part of the human journey - we all eventually ask whether our work matters beyond the paycheque."
Anurag sees this shift reflected in the professionals Outsized works with: "Younger independents reject the 'grind first, find meaning later' model. They want fulfilment now, not as a reward for decades of dissatisfaction. This approach recognises that sustainable careers require both external success and internal alignment."
The conversation reveals a crucial insight: purpose has become infrastructure for sustainable careers. Professionals who ignore alignment questions don't eliminate them - they postpone them until the cost of change becomes much higher.
Can work itself provide meaning, or must it come from elsewhere?
Work often becomes our default identity. "What do you do?" is typically the first question in professional settings, suggesting that career defines personal worth. But can work really provide comprehensive life meaning? "Jobs can't love you back," Will states plainly. "Purpose emerges from meaningful activity - helping others, creating something valuable, serving a cause bigger than yourself. Work can be a vehicle for this, but it's not the only source."
Anurag references the famous story of President Kennedy visiting NASA: when asked what he was doing, a janitor replied, "I'm helping put a man on the moon." The same cleaning tasks became meaningful through connection to a larger mission. "Organisations can signal collective purpose, but individuals must make the personal connection," Anurag notes. "The janitor chose to see his work as part of something significant. That perspective shift is available to all of us."
This reframing suggests that meaning comes from how you choose to view your work, not just what the work involves. Purpose is created through perspective and ownership, not handed down through job titles.
How can independents tell if they're burned out - or fundamentally misaligned?
"Burnout" has become a catch-all term for work dissatisfaction, but it often masks deeper misalignment issues. Understanding the difference is crucial for choosing appropriate responses. "Your body often signals misalignment first," Will explains. "Recurring fatigue, frequent illness, cycles of disengagement that don't improve with rest. When someone consistently dreads work despite having manageable workloads, that's usually about fit, not exhaustion."
Anurag distinguishes between mental and physical symptoms: "Burnout is often mental before it becomes physical. Rest helps with genuine exhaustion, but it doesn't restore engagement. If you take time off and still feel empty about your work, the issue isn't burnout - it's alignment."
The key diagnostic question: does rest restore enthusiasm for your work? If breaks consistently fail to renew your engagement, you're likely dealing with fundamental misalignment rather than temporary burnout. This distinction matters because the solutions are completely different.
Social media celebrates dramatic "quit to find your purpose" stories, but such binary thinking can create more problems than it solves. Anurag shares his own experience: "During COVID, I felt completely misaligned with my corporate role. But instead of quitting immediately, I reframed it as functional rather than emotional. I treated it as a stepping stone, not an endpoint. I negotiated a sabbatical to explore starting a business, with the safety net of returning if it didn't work."
This approach allowed him to pursue meaningful work while managing financial risk. "You don't need to risk everything to make changes. It doesn't have to be binary." Will reinforces this pragmatic approach: "When you quit without a plan, you risk trading one struggle - unfulfilling work for another financial instability. Economic pressure can drain joy from even purpose-driven work."
Here's an example: someone who left a "horrific role" to pursue filmmaking found that financial stress made both situations feel like a struggle. "If I can't pay for the things critical for me and my family to live, then there's no point being in something that gives me joy, because now it's just a struggle - the same struggle as before, just in a different way."
Sustainable career transitions require patience, planning, and pragmatism alongside vision and courage.
The conversation reveals that true success requires integrating achievement with alignment thoughtfully over time. Key insights for independents navigating these questions:
As Will concludes: "You are already whole. Purpose doesn't make you worthy - it flows when you act from who you are." Anurag adds, "Do good consistently. Meaning isn't handed to you; it's created by how you show up every day."
For independents, the next definition of success goes beyond more clients or higher rates. The goal becomes building careers that honour both professional achievement and personal meaning. Rather than choosing between stability and soul, the challenge is creating work that serves both.
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