Finding The True Work Of Your Life — Steve Schlafman & Matt Yao
Here are the top 10 key takeaways from this fascinating conversation between Paul Millerd, Steve Schlafman, and Matt Yao about finding meaningful work, redefining ambition, and creating sustainable career paths that prioritize fulfillment over traditional success metrics.
1. Slowing down is more powerful than speeding up
The traditional approach to career transitions involves pushing harder and moving faster. However, this often perpetuates the same patterns that led to dissatisfaction in the first place. Steve discovered that his "high output" mentality was actually counterproductive to finding meaningful work.
True transformation requires stepping back and creating space for reflection. This means resisting the urge to immediately fill time with new projects or activities. The cocoon phase becomes essential for unraveling old conditioning and discovering what genuinely matters.
When we slow down, we give ourselves permission to examine our motivations and patterns. This process allows for deeper self-awareness and more intentional decision-making about our future direction.
2. Work scripts from childhood shape adult career patterns
Both Steve and Matt carried powerful messages about work from their upbringing. Steve's single mother worked two jobs while his father didn't pay child support, creating a deep association between hard work and security. Matt's immigrant parents achieved success through relentless academic excellence, embedding similar achievement-oriented patterns.
These early scripts become unconscious drivers in our careers. They influence how we define success, how much we're willing to sacrifice, and what we believe is necessary for survival. Many people spend decades following these inherited patterns without questioning whether they truly align with their values.
Recognition of these patterns is the first step toward freedom. Once we understand how childhood messages influence our choices, we can begin to consciously choose different approaches that better serve our adult selves and circumstances.
3. Money beyond basic security doesn't increase happiness
Steve's experience in venture capital taught him that incremental increases in income don't translate to meaningful improvements in life satisfaction. Despite receiving substantial bonuses, he consistently felt unchanged and unfulfilled. This realization became crucial in his decision to leave a lucrative career.
The relationship between money and happiness plateaus once basic needs are met. Additional wealth often comes at the cost of time, relationships, and personal fulfillment. Many high earners discover that they're trading the things that actually matter for financial gains that don't significantly impact their wellbeing.
Understanding this principle provides freedom to make career choices based on meaning rather than maximizing income. It allows people to prioritize family time, creative pursuits, and personal growth over relentless financial accumulation.
4. Ambition can be redefined beyond career achievement
Traditional ambition focuses on climbing corporate ladders, increasing income, and gaining status. However, true ambition can be oriented toward creating a good life across multiple dimensions. Steve's friend Jonathan reframed this beautifully: "I always thought I wasn't ambitious until I realized my ambition was to have a good life."
This expanded definition of ambition includes being present for family, maintaining physical and mental health, nurturing creativity, and contributing meaningfully to others. It recognizes that success isn't just about professional achievements but about crafting a life that feels fulfilling and sustainable.
Redefining ambition allows people to pursue their goals without sacrificing their wellbeing or relationships. It creates space for a more integrated approach to life where career success supports rather than dominates other important areas.
5. Nature provides wisdom about sustainable rhythms
Human work culture is modeled after machines that can run continuously without rest. However, this approach ignores the natural cycles that govern all living systems. Nature demonstrates the importance of seasons, periods of growth followed by dormancy, and the necessity of renewal.
Professional athletics has begun to recognize this truth by prioritizing recovery and rest as much as training and practice. Athletes now use recovery equipment, incorporate yoga and meditation, and understand that peak performance requires strategic downtime. Knowledge workers can learn from this approach.
Embracing natural rhythms means accepting that productivity ebbs and flows. It involves working intensely when energy is high and resting when renewal is needed. This cyclical approach often leads to better long-term results than constant high-intensity effort.
6. Taking breaks requires overcoming deep-seated fears
Both Steve and Matt experienced significant anxiety about stepping away from traditional career paths. Common fears include falling into obscurity, losing professional edge, being judged by former colleagues, and running out of money. These fears are often more powerful than the actual risks involved.
The fear of being forgotten or becoming irrelevant can be paralyzing for high achievers. There's also anxiety about explaining career gaps to future employers or clients. Many people worry they'll be seen as lacking ambition or commitment if they prioritize anything other than continuous professional advancement.
Overcoming these fears requires building a support system of people who understand alternative paths. It also involves examining whether these fears reflect actual risks or inherited conditioning about what constitutes a successful life.
7. Finding good work requires extensive experimentation
Matt's sabbatical involved trying multiple projects simultaneously including blogging, a climate newsletter, and a podcast. This experimentation phase helped him discover what energized him and what felt forced. Many people need this exploratory period to understand their authentic interests and talents.
The key is approaching experiments with genuine curiosity rather than predetermined outcomes. Some projects will resonate deeply while others will feel like obligations. Pay attention to which activities create energy and which drain it. This internal feedback provides valuable guidance about future direction.
Experimentation also involves testing different working rhythms, environments, and collaboration styles. What works for one person may not work for another. The goal is discovering your unique combination of interests, skills, and working preferences that create sustainable engagement.
8. Jealousy dissolves when you find your authentic path
When people are pursuing work that doesn't align with their values or interests, they often experience envy toward others who seem more successful or fulfilled. This jealousy indicates misalignment between current activities and authentic desires. It's a signal that something needs to change.
Once someone finds work that genuinely excites them, competitive feelings tend to disappear. Instead of feeling threatened by others' success, there's often genuine excitement and curiosity about different paths. This shift indicates movement toward authentic work that feels personally meaningful.
The absence of jealousy becomes a reliable indicator of alignment. When you're doing work that fits your unique combination of interests and skills, other people's achievements feel inspiring rather than threatening. This creates space for collaboration and mutual support rather than competition.
9. Supportive relationships enable unconventional choices
Both Steve and Matt emphasized the importance of partners who support their non-traditional career paths. Steve's wife Eliza actively encouraged his transition away from venture capital and reminded him they didn't need maximum income to be happy. This support provided emotional safety for taking risks.
Supportive relationships create permission to prioritize fulfillment over financial maximization. When partners share similar values about what constitutes a good life, it becomes easier to make choices that prioritize time, health, and relationships over income and status.
Without this support, the pressure to conform to traditional career expectations can be overwhelming. Having even one person who believes in your alternative path can provide the confidence needed to persist through uncertainty and external judgment.
10. Apprenticeships offer personalized learning for career transitions
Matt's apprenticeship with Steve demonstrates an alternative to traditional job searches or formal education programs. This people-first approach prioritizes learning from someone whose path you admire rather than finding the perfect role or company. The relationship becomes the foundation for professional development.
Apprenticeships allow for flexible, real-world learning that adapts to individual needs and interests. Rather than following a predetermined curriculum, the learning evolves based on projects, challenges, and opportunities that arise. This creates more relevant and immediately applicable skill development.
The apprenticeship model also provides mentorship, networking, and gradual transition into a new field. It allows people to test their interest and aptitude in a supportive environment before fully committing to a new career direction. This reduces risk while maximizing learning and relationship building.