Sahil Bloom’s ‘Deathbed Regret List’ Offers a Framework for Life Choices

In a recent LinkedIn post, Sahil Bloom shares a powerful thought experiment designed to clarify life’s priorities. Bloom recounts the story of Alfred Nobel, who, after seeing his own premature obituary, was motivated to change his will, leading to the creation of the Nobel Prize. This historical anecdote serves as the springboard for Bloom’s personal exercise: the “Deathbed Regret List.”

Bloom frames this exercise as a way to gain a preview of one’s legacy and make impactful changes while still alive. He writes:

“You don’t need a newspaper to print your obituary. You just need to ask yourself one question: ‘If I were on my deathbed today, what would I regret?'”

This introspective approach, Bloom suggests, is a more accessible and proactive way to confront mortality and its implications for present-day decisions. He emphasizes that unlike Nobel, individuals can initiate this reflection without a public announcement of their demise.

The ‘Deathbed Regret List’ Framework

Sahil Bloom details his personal experience with this exercise, listing nine potential regrets that emerged from his self-examination. These regrets span various aspects of life, from financial security and family relationships to personal growth and presence.

According to Bloom, the list included:

• Leaving family without financial security.
• Missing his son’s “Magic Years.”
• Not spending enough time with his parents.
• Lacking the courage to take significant risks.
• Avoiding challenging endeavors.
• Allowing important relationships to weaken.
• Neglecting physical and mental well-being.
• Succumbing to technology’s impact on presence.
• Losing perspective on contentment.

Bloom uses this list not as a definitive statement of failure, but as a diagnostic tool for present action. The exercise is intended to highlight areas where proactive effort can prevent future remorse.

Applying the Regret Principle to Decision-Making

The concept of projecting oneself into the future to inform present choices is a recurring theme in Bloom’s post. He draws a parallel to Jeff Bezos’s decision to start Amazon, noting that Bezos used a similar method of looking back from the future to assess potential regrets.

As Sahil Bloom explains:

“He projected himself forward, looked back, and asked if he’d regret not trying. The answer was obvious.”

This strategy, Bloom argues, can help individuals overcome inertia and the fear of failure by focusing on the greater regret of inaction. He advocates for using this forward-looking perspective to foster gratitude for the present and encourage incremental progress.

From Reflection to Action

Bloom concludes his post by urging readers to engage in their own version of this thought experiment. He posits that while most will not have the dramatic experience of reading their own premature obituary, the “Deathbed Regret List” offers a practical method for self-reflection and course correction.

In his words:

“You probably won’t get to read your own obituary. But you can do this exercise today. Project yourself to the end. Look back. What would you regret?”

The ultimate goal, according to Bloom, is to “snap back to now and feel the gratitude that comes from knowing you still have time.” He encourages taking “one action at a time” to align present activities with long-term values, thereby mitigating potential future regrets.