Want to succeed? Fail.

Total read time: 8 minutes

Cyclical Iteration. It’s a philosophy that underlies everything we do here at VaynerMedia, from development cycles to client strategies to administrative processes to sushi/sake team dinners.

What is iteration?

-It’s the systemic acceptance of short term failures to ensure long term success.

-It’s the embracing of the cyclical and chaotic nature of growth and the absence of formal long term planning.

-It’s the investment in human capital and relative disregard for protection of existing assets.

This systemic embracing of the inevitability and strengthening nature of human failure that pervades our company culture is, in my estimation, the surest indicator of our eventual success.

Fail harder, fail better.

“Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.” – Samuel Beckett

Iteration is not the process of stepping consistently forward. In fact, quite the opposite, it is predicated on the acceptance of stepping backwards.

Each cycle (or iteration) follows a classic trial-and-error pattern. The first few steps are usually incorrect, but they help expose the complexity of the problem and eventually lead to a more robust and often more innovative solution.

Iteration not only accepts short-term failure, it embraces it. Failure now leads to strength later on.

Seek failure and you will find real strength. Seek perfection and you’ll find weakness veiled as strength.

Disclaimer: I feel obliged to mention that this does not mean that as a company we are releasing substandard or half-cocked strategies or products to our clients. Quite the opposite — the iterative cycles take place internally and help us ensure we can deliver consistently great results.

Safe is risky.

“Safe is risky.” – Seth Godin

If your goal is to never fail (or admit failure), you’ll find that the more you acquire, the more frantically you’ll have to struggle to maintain your “winnings”.

You can’t monitor or control everything. No matter how much you try to keep everything moving consistently upward, something you’re not monitoring is going down.

You know, it takes so much damn energy and cognitive dissonance to convince yourself that you are unfailingly headed on the right path. Why not just admit that there are going to be peaks and valleys??

Sometimes you’re going to forget important things. Sometimes you’re going to do embarrassing shit. Sometimes you’re going to offend and disappoint people you care about or look up to or need approval from.

If you would just RELAX and be ok with losing a few battles, you’d find it’s much easier to win the war.

One of our greatest weaknesses as human beings is our inability to go beyond linear projection. You decide not to lose three battles in a row, because that translates to 9 and 18 in your head.

All important fundamental dynamics are so clearly cyclical, yet we can only take into account a singular slope in our projections, and that chains so many people to overly conservative or risk-averse approaches.

A risk-averse approach is safe in the short term and self-destructive in the long term. And not the fun kind of self-destructive. The slow, crippling, succumbing to death at 24 without realizing it until 42 version of self-destructive. No thanks.

Trust the actors, not the script.

In order to operate on a daily basis, human beings need to ignore a huge number of variables and attribute the continued functioning of those variables to an abstraction that some would call “faith”.

Corporate strategies and sitcoms like Two and a Half Men ascribe that faith to a rigid “plan”, and operate with an implicit wary distrust in the human actors involved.

Iterative strategies and genuine comedies like It’s Always Sunny in Philadelphia and Eastbound and Down have rudimentary guidelines for each scene but the director is happy to throw the script out the window on any given scene because her faith lies with the characters and the actors that breathe life into them.

Get attached to the people, not the product or the processes. The only asset that can flourish without attention and demonstrate true exponential ROI is a human asset.

Make more chairs.

When you get attached to your accomplishments, as a company or an individual, you’re putting your money on a commodity with diminishing returns.

Because anything you build is bound to wither eventually no matter how closely you protect or hoard it, you’re putting yourself or your company into a game of musical chairs; a game that degenerates into a dystopia ruled by scarcity and marked by fearful, animalistic competition between otherwise decent human beings.

The solution? Cut that cord, my friend. Put your faith in your future, not your past.

With each iteration you should focus on increasing your ability to do it faster and better next time rather than clinging to your creation, no matter how valuable it appears.

Anything man can build will inevitably crumble. The tires lose their traction and the hinges rust and the sheen fades. One of the saddest things to see is an organization or a person frantically patching together or attempting to bail out a decaying symbol of their past glory.

The second that glue starts unsticking, you want to confidently assess your dying creation like the million dollar man — “we can rebuild him”.

Don’t fear the reaper.

“Don’t fear the reaper (we’ll be able to fly)” – Blue Oyster Cult

What iteration really comes down to is letting the weak or old parts die the deaths they want to die.

If you don’t keep a healthy population of wolves inside, if you don’t have a certain modicum of ruthless killing in your organization or yourself, you’ll eventually find your business or your life unmanageable due to the unchecked, brimming caribou herd that will overwhelm the system.

So many things would be so much better if people could accept minor losses and deaths in the interest of “strengthening the herd”.

Imagine if you could actually “take a break” in a relationship before the relationship was over on one or both sides, how much more stable and secure would that relationship be?

Imagine if laws were repealed as often as they were passed, how much more accurate and fair would laws be?

I hate to get all Eastern philosophy and Yin/Yang on you here, but failure and death are a necessary counterbalance to (and enabler of) success and life.

If you do it right and embrace the failures in your personal actions, even the final, faltering act will be pleasurable.

Hell, I fully intend to have an open bar and a live band at my funeral.

Life’s a joke, if you let yourself exhale and you celebrate the little deaths instead of dreading them, you might be able to laugh at it again.