Turning 40 is a milestone that often triggers deep reflection, and Paul Millerd embraces this in his latest newsletter with 40 raw, insightful musings about change, work, money, relationships, and parenthood. From abandoning a successful career to chasing a more uncertain but fulfilling path, Paul dives into lessons learned in the past decade. He discusses the importance of rewriting societal narratives, the struggles of financial independence, and how true success comes from defining life on your own terms. His reflections touch on the reality of work-life balance, the power of relationships, and how becoming a father redefined his priorities. If you're looking for both validation and inspiration for taking unconventional paths in life, this is a must-read. As Paul puts it, “Real change is slow and confusing. I want more people to know this so that they might feel permission to embrace the slow and more confusing journey of going after things that matter to them.”
Key Takeaways:
- Walking away from a stable career in his 30s was terrifying but ultimately his best decision.
- Changing direction can happen fast, but internal rewiring takes a lot longer than expected.
- Societal “scripts” from previous generations often lose their relevance and need to be challenged.
- “I’ve never looked back and regretted being more adventurous with my life.”
- Life will eventually push you out of your comfort zone—best to do it intentionally.
On Work:
- The desire to escape work is misleading; true success comes from transcending work.
- Freelancing and self-employment, even for a short time, teaches resilience and independence.
- His most satisfying work experience was writing his book—14 months of challenge and creativity.
- "Burning out happens faster when working for yourself because there are no limits, but this forces you to confront what really matters."
- Tinkering and following curiosity lead to unexpected opportunities.
On Money & Success:
- Achievements bring joy, but the danger lies in becoming addicted to the chase.
- Defining success on personal terms often creates tension with conventional expectations.
- Making less money after earning a high salary is a great way to figure out true priorities.
- Early financial success can feel hollow if it's detached from deeper fulfillment.
- “Money fears are the home of the deepest anxieties—dying, belonging, being loved.”
On Relationships:
- Marriage advice is often unhelpful; what matters is finding someone excited to build a life with you.
- The upsides of a loving relationship vastly outweigh the frustrations of dating.
- Cross-cultural relationships require embracing tension rather than solving it.
- Marrying later in life brought greater appreciation of emotional maturity.
On Parenting:
- Becoming a father was a humbling lesson in embracing the unknown.
- "Every time I’ve felt the pull to 'do more,' I try to think about the end of my life, realizing I won’t regret this time with my child.”
- He mourns the fact that he will have "less time" with his children compared to younger parents.
- Work-life balance is especially difficult as a dad, but prioritizing family is worthwhile.
- Disappointed that many peers are choosing not to have kids, though he understands why.
Life, Happiness & Miscellaneous:
- History offers perspective—humans have always been chaotic, but life is safer now.
- Leisure and deep rest are essential but undervalued in modern hustle culture.
- Politics and news do not contribute to happiness.
- Writing is powerful, exposing what you truly desire.
Recommended Books & Services:
- The Pathless Path & Good Work by Paul Millerd
- CrowdHealth (alternative to US health insurance)
- Nat Eliason’s Build Your Own AI Apps course
If you're eyeing a new chapter in life, Paul's reflections are a heartfelt guide to embracing uncertainty, redefining success, and making the most of the years ahead.
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