Successful people often share the struggles behind their achievements without acknowledging the hidden advantages that made those risks possible. Truly helpful advice tells the whole story.
Successful people love to share their stories—and rightly so. Their paths to conventional success involve overcoming challenges and persevering through hardships, reading like modern-day hero’s journeys. These epic narratives are naturally intriguing, fueling a crowded market of books, articles, and social media content. We consume them hoping to extract the secret formula for our own success.
The problem? Successful people are rarely the most reliable narrators of their own journeys. We vividly remember the obstacles we overcame because conquering them required immense effort. Conversely, we easily forget the advantages we benefited from, because people rarely notice what comes easily.
Lately, my LinkedIn feed has been flooded with founders urging people to quit their jobs, drop out of school, or both, and "bet on themselves." What bothers me about this “quit and start a company” mantra is how reductive it is. It reduces entrepreneurship to a mere test of courage and self-belief. Essentially, it’s the same American Dream we thought we had debunked, repackaged in Silicon Valley wrapping paper.
This advice lacks crucial context—specifically, context about privilege. For every founder who succeeds, nine fail. And for every person who tries to start a company, countless others would love to but simply cannot afford to.
Every success story is the tip of an iceberg
Now in my 30s, I find myself on the giving end of advice, mentoring college students from my alma mater, Dartmouth, and connecting with professionals on LinkedIn. When asked about my zigzagging career—from journalism to commercial real estate, to tech marketing, and finally management consulting—I tend to focus on how I bravely followed my interests. I highlight my willingness to pivot when a role no longer stimulated me.
What I rarely mention is the "Bank of Mom and Dad" that made those leaps possible, especially when I was a recent graduate with virtually no savings. Similarly, when advising Dartmouth applicants, my parents' financial backing never comes up in the conversation.
I remember a conversation with my sister shortly after I graduated. Proud of my Ivy League degree, I was stung when she said, “You didn’t do it on your own.”
“I did do it on my own,” I replied defensively, pointing out that I was the first in our family to attend an Ivy League school.
“No, you didn’t,” she countered. She proceeded to point out that my parents’ financial support allowed me to focus entirely on studying and extracurriculars, free from the stress of paying for SAT prep or the myriad of expenses that make a college application stand out.
Framed that way, I couldn't deny her point. Acknowledging my parents' role doesn't negate my hard work or the all-nighters I pulled; it simply provides the necessary context that I had advantages others did not.
The omitted details of the "hustle"
I realize I tell my career story the exact same way many founders tell theirs online:
“I dropped out of school with no plans, moved to San Francisco, and slept on a friend’s couch until I made it.”
Or:
“I moved to the U.S. with a few dollars in my pocket. I didn’t know anybody. I worked relentlessly, and then I made it.”
None of these details are inherently false, and I’m not accusing these founders of lying. But crucial elements are omitted. Not everyone has the opportunity to go to college just to drop out. Not everyone has a friend in the Bay Area with a spare couch. Not everyone has the legal right or financial safety net to move to a new country.
Tell the whole story
If our goal is to genuinely help others rather than just farm views and admiration, we need to tell the *whole* story.
Take Sukhpal Saini, a serial founder who recently shared that before going full-time on his startup, he spent four years saving $250,000. He built this runway by moving from Canada to the U.S., taking contract work, and juggling three jobs at once. His story is a vital reminder that “betting on yourself” doesn’t mean recklessly quitting your job on a whim; sometimes, it means spending years quietly building the financial runway to make that bet possible.
Yet, his story also begs the question: How many people have access to the circumstances required to build that runway in the first place?
Dylan Pak, a founding member of OpenTrade, took this transparency a step further. Rather than just celebrating the risks of his startup, he explicitly acknowledged the privilege that allowed him to take them: *“If OpenTrade fails, I still have food, shelter, education, and another chance.”*
Failure is still failure, but the *cost* of failure varies radically from person to person. Being able to take a massive risk because you know you will survive the downside is a profound advantage—one worth acknowledging.
Share your failures before the ending is written
I deeply appreciate founders who pull back the curtain on the unglamorous, uncertain realities of entrepreneurship. But I want us to go a step further: share these reflections *while* you are going through them, not just in hindsight.
If you are truly "building in public," you should share your failures as they happen, before you know how the story ends. A post about a loss might not generate the same dopamine hit as a post about a win, and sharing unresolved struggles carries genuine vulnerability. But it helps people connect with you on a human level, and it might even help you find your next win.
When you are asked for advice, acknowledge that you don’t have all the answers. Admit that every person’s context is different, and what works for you might not work for someone else.
And as for you, the reader: be a critical consumer of the success stories you consume.
As you read this, pause and question me, too. How did I get to publish in *Fast Company*? What privileges and advantages paved the way for me? Because before you go out and try to replicate my zigzagging career, you need to understand exactly what I could afford to lose.