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Advice For Young And Ambitious 20Somethings Who Think They Should Be Successful By Now

The one quote that has guided me thus far and still remains one of my daily mantras is from the Roman philosopher Seneca. He said,

“The most important knowledge is that which guides the way you lead your life.”

When I came across this quote in his letters many years ago, it provided both clarity and a grim realization: what knowledge was I currently absorbing to help me lead a better life? As if time stopped due to a bubble bursting, I realized how woefully underdeveloped my mind was for someone in college, and how I depended on traditional methods to enrich my mind when all the resources and tools were readily available. What was ultimately missing was a desire to learn and the habits to bring that desire to fruition.

What’s important at this age is to develop the skill of learning to change your mind—to be humbled, to put things into perspective, to challenge your beliefs and perception.

In Tiny Beautiful Things: Advice On Love and Life From Dear Sugar, a young writer writes a letter to Dear Sugar (author Cheryl Strayed), an advice columnist for The Rumpus known for her vulnerable, heart-warming but also very practical, down to earth advice, and asks:

“Right now, I am a pathetic and confused young woman of twenty-six, a writer who can’t write. I am up late asking you a question, really questioning myself. 


How do I reach the page when I can’t lift my face off the bed? How does one go on, Sugar, when you realize you might not have it in you? How does a woman get up and become the writer she wishes she’d be?”

Strayed  responds beautifully and with tough love as always [emphasis by me]:

“I’d write humility on one side and surrender on the other for you. That’s what I think you need to find and do to get yourself out of the funk you’re in. The most fascinating thing to me about your letter is that buried underneath all the anxiety and sorrow and fear and self-loathing, there’s arrogance at its core. It presumes you should be successful at twenty-six, when really it takes most writers so much longer to get there. It laments that you’ll never be as good as David Foster Wallace—a genius, a master of the craft—while at the same time describing how little you write. You loathe yourself, and yet you’re consumed by the grandiose ideas you have about your own importance. You’re up too high and down too low. Neither is the place where we get any work done.

We get work done on the ground level. And the kindest thing I can do for you is to tell you to get your ass on the floor. I know it’s hard to write, darling. But it’s harder not to. The only way you’ll find out if you ‘have it in you’ is to get to work and see if you do. The only way to override your ‘limitations, insecurities, jealousies, and ineptitude’ is to produce. You have limitations. You are in some ways inept. This is true of every writer, and it’s especially true of writers who are twenty-six. You will feel insecure and jealous. How much power you give those feelings is entirely up to you.”

The universe is strange in its own ways. The day I finished this book was the day that Maria Popova, one of my favorite writers, shipped a project with Holstee on her 7 lessons learned in 7 years of reading, writing, and living. One of those lessons ties beautifully with the admonishment above, said by Maria Popova:

“Expect anything worthwhile to take a long time.” This is borrowed from the wise and wonderful Debbie Millman, for it’s hard to better capture something so fundamental yet so impatiently overlooked in our culture of immediacy. The myth of the overnight success is just that — a myth — as well as a reminder that our present definition of success needs serious retuning. As I’ve reflected elsewhere, the flower doesn’t go from bud to blossom in one spritely burst and yet, as a culture, we’re disinterested in the tedium of the blossoming. But that’s where all the real magic unfolds in the making of one’s character and destiny.


Image from Holstee http://www.holstee.com/products/brain-pickings-poster


For a generation that is relentlessly labeled narcissistic, cynical, entitled, and lazy, it’s important to be humbled and reminded that the kind of success one desires usually requires decades of failure and self-reinvention. We want to believe—and are told at a young age—that perseverance and hard work are the keys to success. They are important, of course, but there is so much more to it than that: environment, relationships, time, luck, and a multitude of other factors that we have no control over.Screen Shot 2014-08-02 at 8.29.08 AM

The Great Discontent recently launched their first issue which contains a series of interviews with artists of all kinds sharing stories on beginnings, risk, and creativity. There were times when I would feel waves of goosebumps because the stories were so powerful, humbling, and human. These stories don’t represent fairies and geniuses, but people who were lost, stumbled, committed to a purpose, went through adversity, but eventually found their rhythm. The one pattern that I’ve noticed throughout all of the interviewees was the notion of nonlinear careers, many (risky) transitions, dealing with immense anxiety and financial crisis, moments of luck, and many of them weren’t successful until after a decade or two into their work.

Like the writer who wrote to Dear Sugar, it’s okay to feel self-doubt and even to have unrealistic beliefs about how successful one should be in their 20s. It’s not a disease, just a symptom of the times. The danger, however, is carrying around these delusions and ignoring wisdom from really smart people. Every day we should strive to put our life into perspective, to not be beaten by constant comparison, and to ultimately realize that our definition of success may fundamentally change as we learn and grow.

But what would be a post about 20somethings without talking about purpose or the meaning of life?

Hunter S. Thompson—one of my early heroes for pursuing the art of writing—received a letter from a friend asking his perspective on the meaning of life and how to find one’s purpose, a predicament of our times regardless of age. You can read the full letter here. What he says is worthy of meditation, not necessarily a prescription to life, but a very practical and equally difficult mindset to build when culture pushes for immediate gratification, safety, and comfort. It’s a piece of advice that I have been following for years and, after revisiting it from time to time, remains truer than before.

Thompson admonishes [emphasis by me]:

“As I see it then, the formula runs something like this: a man must choose a path which will let his ABILITIES function at maximum efficiency toward the gratification of his DESIRES. In doing this, he is fulfilling a need (giving himself identity by functioning in a set pattern toward a set goal) he avoids frustrating his potential (choosing a path which puts no limit on his self-development), and he avoids the terror of seeing his goal wilt or lose its charm as he draws closer to it (rather than bending himself to meet the demands of that which he seeks, he has bent his goal to conform to his own abilities and desires).

In short, he has not dedicated his life to reaching a pre-defined goal, but he has rather chosen a way of life he KNOWS he will enjoy. The goal is absolutely secondary: it is the functioning toward the goal which is important. And it seems almost ridiculous to say that a man MUST function in a pattern of his own choosing; for to let another man define your own goals is to give up one of the most meaningful aspects of life — the definitive act of will which makes a man an individual.”

The way I understand it: Mastery of a skill within a domain (writing, dancing, design, cooking, drawing, singing) begets the fulfillment of one’s desires (lifestyle, goals, aspirations, traveling the world).

Tiny Beautiful Things, Maria Popova’s manifesto, and The Great Discontent are the kinds of literature and visual reminder that helps us change our mind, put our life into perspective, but above all, to empower and remind us that what we desire to achieve in this lifetime is possible with the right mindset and determination.