The Illusion of Being ‘Behind’: Sahil Bloom on Overcoming Time-Based Self-Doubt

In a recent LinkedIn post, Sahil Bloom tackles the pervasive feeling of being “behind” in life, using a decades-old advice column to illustrate how self-imposed timelines can hinder personal growth and the pursuit of dreams. Bloom frames this common anxiety not as a reflection of external reality, but as an “invented” construct that prevents individuals from taking meaningful action.

The core of Bloom’s argument centers on a letter published in the “Dear Abby” column in the year 2000. A 36-year-old man, who had dropped out of college but still aspired to become a doctor, wrote to Abby seeking advice. He calculated that by the time he completed medical school and his internship, he would be 43 years old. He asked if this was too late.

“I’m a 36-year-old college dropout. My lifelong dream was to be a doctor. I have a good job selling pharmaceutical supplies, but my heart is still in medicine. If I go back to college, get my degree, go to medical school, do my internship, and finally start practicing, it’ll take me seven years. In seven years, I’ll be 43 years old. What do you think?”

Dear Abby’s simple yet profound response, as recounted by Bloom, was: “And how old will you be in seven years if you don’t go to medical school?” This question, Bloom explains, served as a powerful catalyst for self-reflection, bringing to mind every instance where he, too, had felt “off track, behind, or lost.”

Deconstructing Invented Timelines

Sahil Bloom elaborates on how these timelines are “entirely invented,” often built from observations of the world and social media. He argues that these self-created maps dictate what people believe they “should have done by 25, 35,” leading to a paralyzing fear of starting later in life.

“We tie ourselves in knots,” Bloom writes. “We know what we really want, but we’re too afraid to go all in because going all in means exposing yourself to real failure, being completely naked.” This fear, he suggests, is a primary driver behind procrastination and the hesitation to pursue passions.

The Inevitability of Time and the Regret of Inaction

Bloom emphasizes that time is an impartial force, progressing regardless of whether one takes action or not. He supports this perspective with research cited from Cornell University, which suggests that while people may regret their actions in the short term, long-term regret stems predominantly from inaction.

“It’s never the things we did that haunt us, it’s the things we didn’t do.”

This research highlights a critical distinction: the enduring sting of missed opportunities versus the often-transitory discomfort of failed attempts. As Sahil Bloom points out, the “harsh truth Dear Abby nailed” is that time waits for no one.

The Power of Self-Permission

A central theme in Sahil Bloom’s post is the idea of self-permission. He questions how often individuals wait for external validation or cues before pursuing their goals, likening it to waiting for someone else to “tap us into our own life.”

Bloom’s ultimate message is one of empowerment. He asserts that individuals do not need external approval – not from advice columns, not from others, and not even from content like his post. The crucial step, according to Bloom, is to “just tap yourself in.”

“You get to choose. You’re not late, you’re not early, you’re exactly where your life has led you to be. And you get to decide where you go from here.”

He concludes by reiterating the central question posed by Dear Abby, urging readers to consider their age in seven years if they choose not to act on their aspirations. Sahil Bloom’s analysis encourages a re-evaluation of personal timelines and a proactive approach to achieving long-held dreams, regardless of perceived age or stage in life.