Sailing With Phoenix: “I Quit My Job To Sail The World & Discovered My Purpose” - Here’s The Secret To Finding Yours
In this episode of The School of Greatness, Oliver shares his story of leaving behind an unfulfilling corporate career to pursue his dream of sailing around the world. After receiving a severe medical diagnosis and spending three years in depression, Oliver made the decision to sell his possessions, buy a sailboat, and document his journey on social media—despite having no sailing experience.
The episode covers Oliver's year-long preparation for solo ocean voyaging, during which he taught himself boat maintenance, electrical work, and navigation. His story includes overcoming a broken rudder during a storm and his unexpected rise to social media fame, where he gained a million followers within days of setting sail. Through his experiences, Oliver discusses how following one's instincts can lead to significant life changes and finding one's purpose.
This is a preview of the Shortform summary of the Jun 18, 2025 episode of the The School of Greatness
Sign up for Shortform to access the whole episode summary along with additional materials like counterarguments and context.
1-Page Summary
Oliver's Personal Background and Motivation For Change
Oliver's journey began with significant challenges, including placement in special education programs throughout his school years. Despite these obstacles, he developed a strong work ethic. His life took a dramatic turn when he was diagnosed with an elderly spine condition - a case so severe it shocked his orthopedic specialist. This diagnosis led Oliver into a three-year period of depression and weekend partying as he struggled to cope with his mortality.
Oliver's Decision-Making Process to Pursue His Dream
After eleven years in an unfulfilling corporate job, Oliver made a bold decision to change his life. Despite being in debt, he quit his job, sold all his possessions, and liquidated his 401k to purchase a sailboat. Encouraged by his brother, Oliver began documenting his journey on social media. An accidentally released video became the catalyst that gave him the courage to fully commit to his dream of sailing around the world with his cat.
Oliver's Ocean Voyage Preparation and Execution
Oliver spent a year preparing for his solo ocean crossing, teaching himself essential skills including boat maintenance, electrical work, and navigation. His preparation was put to the test when, six days into his journey, the boat's rudder broke during a storm. Despite the dangerous situation, Oliver remained calm and managed to fix the problem, demonstrating the resourcefulness he had developed during his preparation.
Oliver's Unexpected Social Media Fame and Impact
Within just 12 days of setting sail, Oliver's story went viral, garnering over a million followers. Lewis Howes notes how Oliver's authentic sharing of his journey captivated audiences worldwide. His story particularly resonated with viewers, as evidenced by one mother who reported her son and his friends eagerly awaiting Oliver's updates. Oliver remains humble about his influence, encouraging others to trust their instincts and take action toward their dreams, no matter how daunting they might seem.
1-Page Summary
Additional Materials
Counterarguments
- Oliver's decision to quit his job and sell his possessions could be seen as financially irresponsible, especially considering his debt and the liquidation of his 401k, which could have long-term consequences for his financial security.
- The decision to embark on a solo ocean voyage with limited experience could be criticized as reckless, given the inherent dangers of sailing and the potential for life-threatening situations.
- While Oliver's story is inspiring, it may not be a practical or advisable path for everyone, especially those with dependents or without the means to take such a risk.
- The rapid success of Oliver's social media fame might set unrealistic expectations for others who might think that such an outcome is easily attainable.
- Oliver's encouragement for others to trust their instincts and take action towards their dreams does not acknowledge the importance of planning and considering the potential risks and consequences of such decisions.
- The narrative may oversimplify the complexities and challenges involved in making such a drastic life change, potentially minimizing the difficulties others may face in similar situations.
- The focus on Oliver's individual success story might overshadow the collective efforts and support systems that are often necessary for such endeavors, including the role his brother played in encouraging him to document his journey.
- The story does not address the potential environmental impact of sailing and the responsibility sailors have to protect the oceans, which could be an important consideration for those inspired by Oliver's journey.
Actionables
- You can develop resilience by setting a daily challenge that pushes you slightly out of your comfort zone, such as waking up an hour earlier to work on a personal project or speaking to a new person each day. This practice helps build the habit of facing and overcoming small challenges, which can translate to greater resilience in more significant life events.
- Start a "Change Journal" to document your journey towards a personal goal, noting down not only achievements but also the emotions and challenges you encounter. This can be a physical notebook or a digital blog. The act of writing can provide clarity and accountability, and sharing your journey with friends or on a small-scale social media platform can offer support and motivation from a community.
- Create a "Skill Swap" group with friends or community members where you exchange knowledge on essential life skills, such as basic home repairs, cooking, or financial planning. Each person could teach something they're proficient in, fostering a supportive environment for learning and preparing for unexpected challenges. This can be done through casual meetups or virtual sessions.
Get access to the context and additional materials
Oliver's Personal Background and Motivation For Change
Oliver's journey and his determination to overcome personal challenges illustrate the transformative power of adversity into motivation for change.
Oliver Faced Learning Disabilities From Special Education To High School Graduation
From first grade all the way through high school, Oliver was placed in special education programs. Despite the feeling of being unable to do school properly, Oliver developed an unwavering work ethic and determination. He learned to lean into this work ethic, believing that through sheer effort, he could accomplish anything he set his mind to.
Oliver's Spinal Condition and Mortality Awareness
Diagnosis Led Oliver Into Depression and Uncertainty
Oliver's life was thrown into disarray when he was diagnosed with an elderly spine condition. He had long endured neck pain, ignoring it until it became so severe that he sought medical attention. The diagnosis, which indicated that his spine was akin to someone over the age of 120, shocked even his orthopedic specialist, who had never seen anything like it in a 20-year career.
This revelation plunged ...
Here’s what you’ll find in our full summary
Oliver's Personal Background and Motivation For Change
Additional Materials
Actionables
- You can harness your work ethic by setting a personal challenge that aligns with your values, such as volunteering for a cause you're passionate about or starting a small project that benefits your community. This allows you to channel your determination into something meaningful, providing a sense of accomplishment and purpose beyond your regular work.
- Create a wellness plan that includes activities to counteract stress and promote mental health, like joining a weekly dance class or starting a hobby that encourages mindfulness, such as painting or gardening. These activities can provide a healthy escape and help you manage feelings of depression or anxiety.
- Init ...
Get access to the context and additional materials
Oliver's Decision-Making Process to Pursue His Dream
After eleven years in a corporate job he hated, Oliver took a leap of faith to pursue his dream. His journey involved significant sacrifices and a commitment to overcome fears and challenges.
After Years in a Hated Job, Oliver Sold Everything to Buy a Sailboat
Oliver Liquidated Assets and Left to Sail the World
Feeling unfulfilled and questioning his life choices after a health diagnosis, Oliver decided to quit his job, even with $10,000 in debt and rent due. He suddenly chose to sell everything he owned, including liquidating his 401k and selling his cars. Without a clear plan or even a boat in mind, he committed to the idea of buying a sailboat to travel the world. After a month of searching, he found a vessel capable of the journey.
Brother's Encouragement Led Oliver To Document Journey on Social Media
Overcoming Fear, Oliver Commits To His Dream
Oliver’s brother played a significant role in his decision-making process. Encouraged by his brother during a pivotal conversation, Oliver decided to commit to his dream. This commitment led him to work tirelessly to learn to sail and prepare the boat, dedicating most of his hours each day to the endeavor.
Over time, Oliver began documenting his journey on social media. An unintentional release of a private video on social media ended up giving him the courage to leave his job and solidify his commitment. Despite initial self-doubt and a lack of social media knowledge, Oliver dedicated himself to improve his skills and post daily ...
Here’s what you’ll find in our full summary
Oliver's Decision-Making Process to Pursue His Dream
Additional Materials
Counterarguments
- While pursuing dreams is commendable, liquidating a 401k and selling assets can be financially risky and may not be the best decision for everyone, especially without a clear plan.
- Social media can be an unpredictable source of income, and relying on it to fund travels could lead to financial instability if not managed properly.
- The decision to leave a stable job and go into debt to pursue a dream may not be advisable for individuals with significant financial responsibilities or those who do not have a safety net.
- Documenting one's journey on social media and gaining a following requires a lot of time and effort, and success is not guaranteed.
- The advice to take risks and chase dreams regardless of how they seem might not take into account the importance of planning and the potential consequences of impulsive decision ...
Actionables
- You can start small by selling unused items and saving the proceeds for your dream project. Begin by identifying items in your home that you haven't used in the past year. Use online marketplaces like eBay or Facebook Marketplace to sell these items. The money you earn can be set aside in a separate savings account specifically for funding your dream, whether it's traveling, starting a business, or learning a new skill.
- Create a support network by sharing your aspirations with friends and family who can offer encouragement. Write down your goal and share it with at least three people whose opinions you value. Ask for their honest feedback and any advice they might have. This can help you gain different perspectives and possibly even a mentor who has experience in the area you're interested in.
- Use a fear-setting exercise to confront potential failures and plan for them. Take ...
Related Shortform Content
Get access to the context and additional materials
Oliver's Ocean Voyage Preparation and Execution
Oliver devoted a year to intense preparation for a daring solo ocean crossing, including overcoming personal hurdles and mastering various technical skills essential for the journey.
Oliver Prepares Boat For Ocean Crossing
Oliver’s preparation for the voyage was extensive and focused on self-sufficiency. He isolated himself to concentrate on the tasks necessary to ready his vessel for the ocean crossing. After purchasing the boat, he spent about a month replacing outdated components, such as 15-year-old lines and rubber elements crucial for the boat's performance.
Oliver Learned Boat Maintenance, Electrical Work, and Navigation to Become Self-Sufficient Sailor
Despite a limited amount of sailing knowledge, mainly informed by YouTube videos, Oliver committed himself to mastering boat maintenance, electrical work, and navigation. This involved adopting several trades, including becoming an electrician, a diesel mechanic, and a plumber, all within a year. This rigorous training helped him become a self-sufficient sailor able to face the demands of an ocean voyage.
Part of his mental preparation involved overcoming discouragement and self-doubt. After receiving a life-altering diagnosis, Oliver was initially hindered by indecision. It took him two years to commit to buying a boat and beginning his journey. To overcome this, he focused on addressing each immediate problem one step at a time, transforming his challenges into manageable tasks.
In Challenges and Close Calls, Such as a Broken Rudder in a Storm, Oliver Stays Calm, Resourceful, and Focused On Solving Problems
During the voyage, Oliver's resilience was tested. He mentions that one can expect things to break on such an undertaking, underlining the necessity to have both resources and skills to address these issues. For Oliver, the worst-c ...
Here’s what you’ll find in our full summary
Oliver's Ocean Voyage Preparation and Execution
Additional Materials
Actionables
- You can build resilience by setting a personal challenge that requires incremental learning, such as growing a garden from seed to harvest. Start with basic gardening research, then progress to selecting seeds, preparing soil, and daily care. As you encounter issues like pests or weather damage, you'll learn to troubleshoot and adapt, mirroring the problem-solving skills needed for larger endeavors.
- Enhance your ability to stay calm under pressure by practicing mindfulness during routine tasks, like cooking. Focus on the sensory details and steps involved, and if something goes wrong, like a dish burning, use deep breathing and logical thinking to resolve the issue without panic, training your mind to react calmly in unexpected situations.
- Develop a step-by-step approach ...
Related Shortform Content
Get access to the context and additional materials
Oliver's Unexpected Social Media Fame and Impact
Oliver's journey from an aspiring adventurer to a social media sensation exemplifies how a single decision can capture the hearts and imaginations of people worldwide.
12 Days After Setting Sail, Oliver's Story Went Viral, Gaining Over a Million Followers on Social Media
On the day Oliver set sail to cross an ocean, he shared an accidental post on TikTok that turned his life around. Struggling for survival out at sea, he went viral, gaining over a million followers within just 12 days of his departure. Lewis Howes, during the interview, reflected on the incident when Oliver's video, unintentionally shared with all his bosses, became a pivotal moment that catapulted him to online fame.
Thousands, Captivated by Oliver's Journey, Find Inspiration and Hope in His Leap of Faith
The video clip that went viral was an embarrassing yet serendipitous occurrence that influenced Oliver's decision to embrace his new path. As Oliver documented his journey on social media, comments began pouring in. These comments revealed his story's power as it brought people together. A mother recounted how her son and his friends were glued to their phones, waiting eagerly for Oliver's next update, and Oliver acknowledged this communal aspect as the coolest thing. Lewis Howes underscored how Oliver's authentic sharing and dogged pursuit of his dreams captivated and inspired an audience that grew exponentially.
Oliver Is Humbled by His Story's Ability to Inspire Others
In disbelief, Oliver watched as the number of followers climbed, as people cheered him on his path toward Hawaii. He expresses that the real impact of his viral fame might only hit him fully upon his arrival in Hawaii. Despite the surreal experiences and the remarkable nature encounters, like dolphins joining him, he remains aware of the dream-like sensation it brings to his online audience.
Oliver' ...
Here’s what you’ll find in our full summary
Oliver's Unexpected Social Media Fame and Impact
Additional Materials
Counterarguments
- The rapid gain of followers may not solely be due to the inspirational nature of Oliver's journey but could also be attributed to the algorithms and the nature of viral content on social media platforms.
- While Oliver's story is inspiring to many, it's important to acknowledge that not everyone has the means or circumstances to take such leaps of faith, and for some, the responsibilities of daily life may not allow for such adventurous undertakings.
- The impact of social media fame can be fleeting, and while Oliver is humbled now, sustained attention and influence often require continuous effort and can come with its own set of challenges and pressures.
- Trusting instincts and taking the first step is valuable advice, but it's also important to balance this with careful planning and consideration of potential risks, especially in endeavors that involve physical danger like crossing an ocean.
- Oliver's story, while resonant with many, might not ...
Actionables
- You can harness the power of social media to share your personal journey by creating a dedicated hashtag for your adventure, whether it's learning a new skill or changing a habit, and posting regular updates to connect with others who might find inspiration in your story.
- By documenting your progress and the challenges you face, you create a narrative that others can follow and relate to. For example, if you're learning to play the guitar, use a hashtag like #MyGuitarJourney and post short clips of your practice sessions, sharing both successes and setbacks.
- You can cultivate courage and take action on your aspirations by setting a "First Step Day" where you commit to initiating a project or goal you've been hesitant about.
- Choose a date and publicly commit to it by telling friends or posting on social media. For instance, if you've always wanted to start a blog, declare your "First Step Day" as the day you'll publish your first post, and use the buildup to that day to prepare and gather support.
- You can find and connect with others who share your quest for purpose by starting a virtu ...
Get access to the context and additional materials
Create Summaries for anything on the web
Download the Shortform Chrome extension for your browser
