Consider the story of James, who from an early age was obsessed with projecting an image of success. After graduating from an elite college, he worked in a high-paying corporate job he didn’t particularly enjoy. The salary allowed him to pay his sister’s medical bills, something that mattered to him deeply. As James climbed the ranks, his promotions afforded the luxuries he craved — a BMW, tailored suits, and memberships in exclusive clubs. To fund it all, James worked punishing hours, neglecting both his health and relationships. At night, he would often lie awake, haunted by a deep-seated feeling of emptiness as the silence of his massive house echoed back his unresolved anxieties.
James owned a huge home designed to entertain guests and flaunt his materialistic accomplishments. Yet behind the shiny facade, he constantly felt anxious, unsettled, and disconnected from his work. The handful of interests he once enjoyed faded as work consumed his time and drained his energy. In his loneliest moments, which occurred almost daily, he wondered whether his relentless pursuit of success was really worth it. He felt like he had a pebble in his emotional shoe but didn’t know how to remove it. The intense pressure led to frequent migraines and creeping hypertension, warning signs he routinely ignored to meet his next business target. James was obsessed with “What do I want?” to the detriment of “How do I feel?”
James needed money so much because he knew himself so little. The pursuit of money justified his avoidance of meaningful self-reflection.
While helping his sister made James feel good, it was outweighed by the painful discovery that no amount of quantifiable success in his outer journey could compensate for the gaping void in his inner journey. Winning the wrong game only magnifies the inherent emptiness of playing it.
Compare James with Alyssa. Alyssa didn’t care about fancy possessions or social status. She worked a modest, part-time job in insurance that paid the bills, but her true calling was her side hustle. She crafted rustic furniture from reclaimed wood and other materials. Alyssa sometimes wondered if she’d made a mistake turning down full-time job offers. But every time she stepped into her workshop, the doubt melted away and she got lost in the therapeutic, tactile creative process.
For Alyssa, success was an inward endeavor. It was about self-expression, ornamenting the world with her unique creativity and delighting customers who could sense the life she breathed into each piece. When Alyssa faced difficulties, she always reminded herself why she chose her work, enabling her to see no challenge as insurmountable. Alyssa wanted the business to grow, but even if it stayed small, she knew she would still feel satisfied with her work at the end of each day.
James optimized for the outer journey, but despite being financially successful, his daily subjective experience was to suffer in comfort. Alyssa optimized for the inner journey. She wasn’t wealthy by conventional standards, yet she richly enjoyed each moment in a way that James could not even imagine. While James tossed and turned in bed, stressed by the day’s events and woke up poorly rested, Alyssa slept peacefully and deeply, rising with boundless energy. Alyssa grasped an important distinction that James had overlooked — comfort is empty while peace is revitalizing.
James constantly operated from a sense of lack, forever chasing more to fill an emptiness he couldn’t articulate. Alyssa, in stark contrast, understood that she was already complete and that everything she accomplished was merely an extra gift. She moved through life like she was playing with house money, approaching each day with joy and curiosity rather than anxiety or desperation.
Alyssa was aware of the quantification bias, the psychological tendency to overvalue the things that can be quantified at the expense of those that cannot be measured. She observed that because money is easily quantified, it tends to be overvalued at the expense of well-being metrics that resist concrete measurement. She realized that our failure to widely quantify attributes like energy levels, creative output, and inner peace may obscure their significance, but this does not diminish their importance.
Alyssa understood that while money is replaceable, time is irreplaceable.
There is a sequel to this story. Alyssa’s drive to produce high-quality artwork resulted in more and more client referrals. As demand increased, she quit her part-time job and hired others to assist her. Her mother fretted about the uncertainty, pleading with her to keep the insurance job for “just one more year.”
But Alyssa could sense the momentum, so she quit her job and doubled down on what was working. Before she knew it, she had ten full-time staff. She made more money than she could spend. There were also economic downturns and, at times, her business suffered. Despite the challenges of running a business, Alyssa never rushed her work and always enjoyed giving full attention to her creative expression. After all, the primary reason she went into business was to enjoy delighting customers with unique artwork.
As you reflect on the contrasting journeys of James and Alyssa, consider which elements of their lives mirror your own. Are you drawn to the allure of sophisticated outward appearances like James? Or do you align more with Alyssa’s approach, prioritizing the inner journey over the outer journey, placing a premium on the creative process and finding meaning in the impact your work has on others?
To embody Alyssa’s experience, ask, “In which specific activities have I been completely present? What experiences have I had where time stopped?” Make a list. Then choose the most important activity for you. Carve out sacred time for that activity and observe how you feel before, during, and after that activity. Then use the quality of that experience to question how you will spend the rest of your day.
Ask yourself, what needs to change?
This article is an excerpt from Chapter 3 of Choose Your Work
Footnote
she was playing with house money: The expression “playing with house money” refers to the idea that if you go to the casino and win, say $100, that $100 is called “house money.” So if you lose it, you’re not concerned because the money was not yours before you arrived.
Dan Dobos writes about decision making, personal growth, human potential, fulfillment and helping people choose the work that they are meant to do. He is the author of Choose Your Work.