06/04/2013 12:22 EDT | Updated 08/04/2013 05:12 EDT

The Case For Failing In Your Twenties

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Businessman suffering stress.

The aptly-titled New York Times feature,"Kids These Days," profiles a group of young and driven twenty-somethings currently taking (or set to take) the world by storm. From fashion to technology to music, the article ultimately attributes this success to the resurgence of a Red Bull-guzzling, YOLO mantra lifestyle mirrored in the careers of predecessors such as Bill Gates (who started Microsoft at 20), Steve Jobs (who started out at 21) and the poster child for young CEOs -- Mark Zuckerberg (who founded Facebook at just 19). While the piece scrapes the surface of young people who have succeeded at launching exemplary businesses and careers, it also brings up a glaring point: Many more fail.

At 26, I find myself frequently cornered into discussions concerning so-called "quarter life crises." While they run the spectrum from remuneration to relationships, a unifying theme is the avoidance of failure and the pursuit of success in these realms. What I've taken away from these conversations is the resounding conclusion that failure is not tantamount to a lack of start-up capital and, in an age of widespread access to all kinds of information, it is certainly not due to a lack of know-how. Instead, it is self-engineered roadblocks and our own personal approaches to facing the F-word that hold us back. Nowhere is this idea more applicable than in the field of entrepreneurship, with its inherent affinity for risk taking. Here are some of the greatest lessons I have learned from my own failures and the failures of others:

1. Robert Frost may no longer be relevant

In what has become one of the most widely-recognized poems ever written, Frost writes: "Two roads diverged in a wood, and I -- I took the one less traveled by, And that has made all the difference." True though it may be that a career should be pursued out of one's own interests and not some perceived path, choosing the road less traveled by is really only advisable if you have some idea of where that road leads. It takes an element of practicality to turn ideas into plans, and the harsh reality is that not everyone is equipped to do so straight out of college. Many would argue that, at the end of the day, passion trumps being practical. But passion itself tends to come with a bit more focus and direction than merely 'following your heart' -- another played-out quote.

2. Money Matters

Money matters, and the truth is that many twenty-somethings (and older) are still coming to terms with its value. A central part of any business, whether it be a non-profit or a financial services firm, is financial sustainability. Few have articulated this as perfectly as Akili Dada, founder of Wanjiru Kamau-Rutenberg, said during an interview as part of the social enterprise web series, Cafe Impact: "You have got to feed yourself, you have got to be safe and I don't think you add value to the world by being unsafe, by being hungry and by being so miserable that the people you purport to help, would rather you were not in their lives."

3. Potential isn't good enough

Potential is a great thing to have if you're looking for an entry-level job, but starting a business and getting people to believe in that business enough to back it, requires much more. So if you are not 100 per cent confident in what you have to offer in a new product or service, don't expect anyone to be either. Any person who has ever attempted to complete a business plan knows it is quite possibly the most humbling experience you will ever go through, largely because it forces you to face the Achilles Heel of every entrepreneur: Self-doubt. As one person described it, "Writing a great business plan is like a good workout; if it's not a painful process, you're probably not doing it right."

4. Anything you can do, I can do better

Twentysomethings have good reason to be risk-averse: Our generation has been victim to the uncalculated risks taken by others, and it could be argued that the aftershocks of 2008's global economic crisis conditioned many into favouring job security over the potential exposure to failure that comes with striking out on your own. That being said, holding out on starting something because it may not necessarily be 'groundbreaking' ultimately refutes the principle on which modern society itself is based: Innovation. This is probably the most tragic cause of failure because it either stems from a glorified ideal of having to be the best or first at something or -- even worse -- a fear of competing altogether.

5. Acknowledge Fear

Acknowledging fear forces you to take stock of your strengths and seek out others who may be able to support your weaknesses. This is why many of the most successful start-ups -- from the accessible Refinery29 to the aspirational Moda Operandi -- tend to have a dynamic duo at the helm. Worse than fear, pride has broken families, launched wars and ruined many a man; why let it get in the way of you starting something potentially amazing?

6. Redefine Success on your own terms

Success has a different meaning for everyone. For some it's starting a family; for others it's founding a Fortune 500. It is a lot harder and takes a lot longer to succeed when you are striving for what someone else deems to be success as opposed to taking the time and introspection needed to find your own definition. Whatever you decide, it may not be perfect, but it is certainly valid.

In Worstword Ho, novelist Samuel Beckett provides a quote that transformed my definition of success, because it forced me to come to terms with failure as a by-product of taking a chance in its pursuit: "Ever tried. Ever failed. No matter. Try again. Fail again. Fail better."