Successful people love to share their stories—as they should. Their paths to conventional success involve overcoming challenges and persevering through hardships, reading like a modern-day hero’s journey. These epic stories are naturally intriguing to the masses, which explains the crowded market of books, news articles, and social media content about their successes. We hope that by learning their stories, we may find some untold insight into achieving success ourselves.
The problem with successful people’s sharing their stories, and with them, advice on how to do the same, is that they may not be the most reliable narrators. People remember the obstacles they overcame because overcoming them required effort, but they stop noticing the advantages they benefited from because people rarely remember what’s easy.
Lately, my LinkedIn feed has been full of founders telling people to quit their jobs, school, or both, and bet on themselves with their own business. What bothers me about the “quit and start your own company” advice is how reductive it is. It reduces entrepreneurship to a choice, one that tests a person’s courage and conviction in themselves. Essentially, it is the same American Dream I thought we had debunked, repackaged in Silicon Valley wrapping paper.
For every founder who succeeds, many more fail, as many as nine in 10. For every person who tries their hand at starting a company, there are many more who would like to but can’t.
That’s the issue with the advice being doled out right now: It lacks context. More specifically, it lacks context about privilege, that pesky little thing we have but refuse to acknowledge.
Every success story is the tip of an iceberg
Now in my 30s, I find myself on the giving end of advice, talking to college students from my alma mater, Dartmouth, and others who find me through LinkedIn. When people ask about my zigzaggy career, I tend to focus on how I followed my interests. I went from journalism to commercial real estate to tech marketing and eventually into management consulting. I like to talk about being willing to try something new when what I was doing no longer felt right or stimulating.
What I rarely think to mention is the Bank of Mom & Dad that helped make some of these choices possible, especially when I was a fresh college graduate with very little savings. Similarly, when I talk to Dartmouth applicants about getting into Dartmouth, my parents never even come up in the conversation.
I recall a conversation I had with my sister after graduating from Dartmouth. I was so proud of getting myself in there and graduating with an Ivy League degree that when she said, “You didn’t do it on your own,” it felt like a slap in the face.
“I did do it on my own,” I said, referring to the fact that no one from our family had ever gone to an Ivy League institution.
“No, you didn’t,” she said, and proceeded to point out that my parents and their financial support made it possible for me to focus on studying and extracurricular activities without worrying about anything else, like paying for SAT prep courses and the many standardized tests that make a college application stand out.
When framed that way, it was impossible for me to deny that my parents did play a role in my acceptance to Dartmouth. Acknowledging the context of my admission to Dartmouth doesn’t negate the fact that I earned my place at the school or that I worked extremely hard and pulled a lot of all-nighters to get good grades. It does, however, allow people to understand that I had advantages that maybe some others didn’t.
The way I tell my career story is the way I’ve seen a lot of founders talk about their entrepreneurial journeys online.
I dropped out of school with no plans, moved to SF, and slept on my friend’s couch until I made it.
I moved to the U.S. with a few dollar bills in my pocket and nothing else. I didn’t know anybody. I barely spoke English. I worked very hard and then I made it.
None of these details are false, and I’m not accusing these founders of lying. But I am pointing out that some things seem to be omitted, or at least not actively acknowledged. Not everyone had the opportunity to go to college in the first place, only to drop out. Not everyone has a friend who happens to live in the Bay Area with a couch for them to sleep on. Not everyone has the right to move to the U.S.
Tell the story, the whole story, and nothing but the whole story
If our goal is genuinely to help, rather than simply to get views and admiration, then we need to tell the whole story.
Sukhpal Saini, founder of several businesses, recently shared on LinkedIn that before going full time on his startup, he spent four years saving $250,000. He increased his income by moving from Canada to the U.S., taking on contract work, and, at one point, working three jobs simultaneously. His story is a useful reminder that “betting on yourself” doesn’t necessarily mean waking up one morning and quitting your job. Sometimes, it means spending years building the financial runway that makes taking that bet possible.
At the same time, his story raises another question: How many people have access to the circumstances that allowed him to build that runway in the first place?
Perhaps he was saving that for a future post, but I recently stumbled upon a post from one of OpenTrade’s founding members, Dylan Pak, that went a step further. Rather than simply celebrating the risks he was taking with his startup, Pak 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 what failure costs each of us can be radically different. Being able to take a risk because you know you’ll survive the downside is itself an advantage worth acknowledging.
I more than appreciate the founders who are pulling back the curtain on not just the unglamorous parts of entrepreneurship that are shareable on social media, but the really difficult parts that make entrepreneurship feel more uncertain. What I would like more of us to do, beyond sharing these reflections after the fact, is to share them as we are going through them.
If you truly are building in public as you claim and committed to taking people on the journey with you, then failure, which is an inevitable part of the process, is something you should share. A post about a loss may not generate the type of response a post about a win will, and there are genuine risks to sharing your failures before you know how they will be resolved, but there are benefits, too. Sharing what you haven’t figured out can help people connect with you on a more personal level and, who knows, perhaps even help you find your next win.
So share your failures now. Not after you’ve made it. Not after they’ve become a thing of the past. Share them while they’re happening, when you don’t yet know how your story ends.
When you’re asked for advice, acknowledge that you don’t know everything, that every person’s context is different, and that even with the same context, what works for one person might not work for another.
As for you, my readers, when you’re on the receiving end of advice, be critical of the stories you’re being told.
As you’re reading this, pause and question me too. How does someone get to publish in Fast Company? What privileges and advantages have I had that made this possible? Because before you go out there and copy my zigzaggy career, understand what I could afford to lose.