About Leo Ariel
Leo Ariel is a former Amazon software engineer who graduated from Cornell University. After just 10 weeks at Amazon, he made the bold decision to leave his $170,000/year position to travel the world for 12 months, visiting 12 countries. During his travels, he co-founded a tech startup focused on exclusive content platforms for creators. Leo is also a prolific writer on Substack, documenting his journey in his series "One Year of Travel, New Year New Me."
Episode Summary
- Leo shares his journey from Cornell University to Amazon, where he worked as a software engineer in a mostly remote role making $170K at entry level.
- Despite having an ideal setup on paper, Leo was deeply unhappy and felt drained after every meeting, leading him to make a radical decision to leave.
- He discusses the courage it took to leave after just 10 weeks (plus 12 weeks of internship), going against conventional wisdom about staying at companies for longer periods.
- Leo traveled to Bali, Portugal, Vietnam, South Africa, Argentina, Colombia, Australia, Japan, and Spain among other destinations.
- He shares how he met his co-founder at a digital nomad meetup in Argentina and started building an exclusive content platform for creators.
- The conversation explores Leo's intuitive approach to decision-making and goal-setting, centered around happiness rather than rigid plans.
Key Takeaways
- Happiness should be the primary framework for making decisions - if you're unhappy, address it rather than waiting for external validation or timelines.
- Sometimes the right decision is to leave quickly rather than staying to "look good on a resume" - the question to ask is "for what?"
- Self-awareness is foundational - you cannot make authentic decisions without understanding yourself first.
- Your first major independent decision can be transformative - Leo describes leaving Amazon as "the first decision I made for myself."
- You don't need a detailed plan to take action - intuition and happiness can guide you effectively.
- Financial constraints can be more flexible than we think - Leo thought he had 6 months of savings but stretched it to complete his full year of travel.
Productivity & Success Habits
Leo's approach to productivity is distinctively intuitive and unconventional. Unlike many professionals, he keeps his calendar completely empty, finding comfort in flexibility rather than structure. "If I had a lot of things on there that I didn't want to do I would look at that and that would probably give me anxiety," he explains. His writing process for his Substack newsletter is driven by genuine enjoyment rather than obligation - he happily spends 20+ hours on a single postcard because he finds the work fulfilling. Leo views documentation as part of his creative process, counting activities like taking photos and even thinking about content as part of the work. His philosophy centers on making things easy for himself: "I don't really force myself to do anything." Rather than following strict routines, he responds to what feels right in the moment, which paradoxically allows him to get significant work done including building a startup, writing long-form content, and maintaining multiple content series simultaneously.
Final Thoughts & Advice
Leo's core message is refreshingly simple: follow your heart and trust that things will work out. He emphasizes that the 9-to-5 path is just one option among endless possibilities - traveling the world, being a solopreneur, or creating your own path are equally valid choices. However, he stresses that self-awareness is the prerequisite: "It all starts with self-awareness... a lot of people in the world they're very happy with the 9 to 5." The key is knowing yourself well enough to understand what will make you happy. He cautions against regret as the worst outcome - calculating that if you work until 65, you're giving up 50% of your best active years to something that may not fulfill you. His parting wisdom: "Follow your heart, follow your guts, what makes you happy. Listen to fewer people if that's what it takes. Learn to know yourself - self-awareness - and yeah just follow your passion and trust that things work out."
Notable Quotes
"I think meeting him is what for me I only do something if I think it's possible. Right, I'm building a startup. I call it building a billion dollar business and might sound ambitious but I think we can get there."
— Leo Ariel On the mindset behind starting his tech startup with his co-founder.
"It was actually the first decision I made for myself. Everything prior was made for me. I didn't choose which neighborhood to live in, I didn't really choose which school to go to... this was really the first break that I'd see define my year."
— Leo Ariel Reflecting on why leaving Amazon was such a pivotal moment in his life.
"For what? Right, I know that I don't like this, why would I stay here for another year? It wasn't like I needed the money to feed my family."
— Leo Ariel Challenging the conventional wisdom about staying at jobs for a minimum amount of time.