The Uncomfortable Truth About Success | Chase Jarvis

Here are the top 10 key takeaways from Chase Jarvis's raw and honest conversation about the uncomfortable truths of success.

1. Life is long, not short

The conversation challenges the common belief that "life is short." Chase Jarvis suggests that viewing life as long, rather than short, can profoundly change our approach to decision-making. When we believe life is long, we become more thoughtful and intentional with our choices instead of scurrying around making hasty decisions.

This perspective encourages investing time and energy into things that truly matter. It's not about rushing through experiences or milestones, but rather savoring them and making deliberate choices. Seneca's philosophy is referenced, noting that life isn't inherently short - we make it short by wasting so much of it.

2. Growth happens through incremental steps

Success rarely comes from dramatic leaps or single risky decisions. Instead, it's typically a series of smaller, connected steps that build upon each other. Ryan and Chase discuss how ventures often start with one decision that leads naturally to another, creating a path forward that wasn't initially planned.

This incremental approach to growth applies to both business and creative pursuits. The conversation points to Ryan's bookstore as an example - what began as a simple bookstore evolved when they needed to film there, then expanded when the neighboring building went up for sale. Each decision was a response to the previous situation rather than a grand, risky vision executed all at once.

3. Risk mitigation over risk-taking

Contrary to popular belief, successful entrepreneurs aren't primarily risk-lovers but risk-mitigators. They take calculated risks while finding ways to protect against potential downsides. The podcast references Richard Branson, who is often portrayed as a bold risk-taker but actually deeply focuses on "protecting the downside."

Branson's purchase of a 747 to start Virgin Airlines is used as an example. While publicly it appeared to be a huge gamble, he had pre-negotiated the price to sell it back if the venture failed. This approach of taking just one risk at a time while systematically removing other layers of risk is likened to peeling an onion - gradually making the business more secure through strategic decisions.

4. The distortion of success timelines

Social media and public narratives often distort the timelines of success, making it appear as though successful people achieved their status overnight. This creates unrealistic expectations and can be disorienting and demoralizing for people building their own careers. Chase uses the analogy of village life versus modern life to illustrate this point.

In village life, you would see someone like "Gary the hunter" develop his skills over time, witnessing his failures and progress. By contrast, modern culture often presents only the end result - the superstar at Wembley Stadium - without showing the years of work and struggle that preceded it. This distortion makes success seem unattainable when in reality it's a long process of application and effort.

5. Attention is about directing, not receiving

While our culture emphasizes getting attention as crucial for success, Chase argues that the real value lies in how we direct our own attention. The ability to focus and choose what we pay attention to is more valuable than receiving attention from others. This counterintuitive approach suggests that becoming skilled at directing your attention actually leads to receiving attention as a byproduct.

The discussion notes how fundamental attention is to human experience - from infants needing attention to survive to adults defining their lives through what they focus on. This shift from seeking attention to consciously directing it represents a more mature approach to both creative work and personal development.

6. Intuition as a crucial decision-making tool

Despite being undervalued in rational, data-driven environments, intuition emerges as a vital decision-making tool throughout the conversation. Chase shares how he worked on a book for over a year, then threw away 55,000 words eight weeks before his deadline because his intuition told him it wasn't the right book. This decision, while appearing risky, led to creating a much stronger work.

Intuition is described as a "muscle" that can be developed over time, allowing you to make decisions that data alone can't guide. The conversation suggests that intuition operates faster than rational thought and involves bodily sensations (hence "gut feelings"), drawing on cellular-level memories and experiences. Many of life's best decisions come from listening to this internal guidance system rather than purely rational analysis.

7. Success often requires letting go of control

Building something beyond a certain scale often means sacrificing the creative control and autonomy that attracted you to the work initially. Chase reflects on his experience with Creative Live, where scaling the company ultimately distanced him from the creative aspects he loved. What began as an artistic venture eventually required him to become a full-time executive.

This creates a paradox where success can actually take you further from your original passion. The conversation highlights how bringing in venture capital means you're no longer the ultimate decision-maker - someone else determines whether you can accept deals or how you should grow. Both speakers acknowledge that sometimes staying smaller or more boutique can be the braver choice, allowing creators to maintain their vision and lifestyle.

8. Constraints enhance creativity

Rather than limiting creativity, constraints can actually enhance it by providing direction and forcing innovative solutions. The conversation compares constraints to the structure of poetry - the limitations of rhyme schemes or formats like haiku don't restrict creativity but instead channel it in powerful ways. Similarly, personal constraints like "I won't travel more than X days per year" can lead to more thoughtful decisions.

Applying constraints to life decisions means setting clear boundaries about what matters most. This might include defining success concretely, setting a financial goal after which you'll retire, or determining how much time you're willing to allocate to a project. These self-imposed limitations connect you to reality instead of endless striving, providing "north stars" that guide decision-making.

9. The disconnect between external success and fulfillment

Chase describes a moment when he was at the apparent pinnacle of success - having just gotten off stage with Lady Gaga announcing the relaunch of Polaroid, with offers to buy his company and millions of followers. Yet in this moment of triumph, his wife asked him, "What are you doing? How much is enough?" - highlighting the disconnect between external achievements and personal fulfillment.

This stark realization illustrates how success can create a contradictory situation where you're unhappy with the life you've created yet spending all your energy trying to get more of it. Both speakers discuss how critical it is to recognize when you're pursuing things that aren't making you happy simply because others value them or because the economic logic suggests you should continue.

10. The importance of losing track of time

Ryan shares a personal rule: "If you don't regularly forget what day it is, you're not doing interesting enough work." This state of flow, where you become so immersed in what you're doing that time seems to dilate or disappear, is presented as a sign of meaningful engagement with life. It represents a break from the rigid structures that typically dictate our days.

The conversation references how disorienting yet revealing the pandemic was for many people when traditional time markers disappeared. This disorientation highlighted how much of our time awareness is tied to artificial constructs rather than genuine engagement. Both speakers suggest that regularly losing yourself in work, family time, or hobbies indicates you're living authentically rather than simply following externally imposed schedules and expectations.