Introduction: Embrace Challenges, Conquer Goals

In the ever-evolving digital landscape, even the most tenacious and accomplished business leaders sometimes succumb to the temptation of throwing in the towel at the first sign of failure or adversity. This phenomenon is especially pronounced in the realm of digital entrepreneurship, where the journey to success is often marked by intense competition and rapid changes.

Take the rise of Netflix as an example – a game-changer that could have been countered by Blockbuster. Instead, Blockbuster struggled, stumbled, and eventually tapped out and quit. The lesson?

Quitting is a surefire way to ensure you never win. We know this – so we’ve also come up with gateway drugs to rationalizing quitting, and deciding to wing it is often one of them. People invent reasons and means to “make it up as they go along” – to wing it.

Reality Check: Making it up as you go along isn’t going to make it.

1. The Grit to Persist: Battling Through Challenges

In any new endeavor, when starting on foreign soil, it's all too common for individuals to abandon their aspirations when faced with initial setbacks or when the going gets tough. In the digital sphere, where expertise today can turn into inexperience tomorrow, adaptation is key. Things change at a breakneck pace, and the ability to endure growing pains and setbacks is a requisite for success. Will you lead your team through adversity, or will you walk away?

Failure is guaranteed – it’s priced into the journey.  Another guarantee is that quitters never taste victory.

2. Rise from the Ashes: Overcoming Failure with Resilience

A disheartening truth is that many individuals call it quits the moment they stumble or face their first failure. Instead of rallying their troops, gaining insights, adjusting strategies, and honing their efforts, they abandon their pursuits altogether. The process of growth involves enduring trials and tribulations, regardless of whether you're Steve Jobs or Forrest Gump.

For those who possess unwavering dedication, quitting isn't a consideration – it's about confronting failure head-on and growing from it.

3. The Illusion of "Winging It": A Mirage for the Uncommitted

While some may not technically quit, another peril lurks in the shadows – the notion of "winging it." This half-hearted approach is a hallmark of those who shy away from commitment and planning, reminiscent of modern jazz musicians whose improvisations quickly disconnected from harmony, rhythm, and melody transformed into noise, not music. That’s what happens when you wing it too long.

When’s the last time you bought a modern Jazz Album album? Me neither. How much splatter paintings are you buying these days? Me neither.

All that random improv quickly becomes erratic, off-the-reservation, grasping at straws, throwing spaghetti at the wall to see what sticks, until finally the noise is acknowledged. Then come the excuses. Instead of playing what’s planned out on the sheet music, all hell breaks loose, and chaos doesn’t deliver a positive return.

“Winging it” is the sanctuary of quitters.

Defining "Winging It" in the Digital Arena: Tactical Hands-On Hopium

Wingers are like gambling addicts who think they’re going to beat the house – constantly using company money to try!

Instead of meticulous planning, "wingers" embrace a different path, one fraught with pitfalls:

• They hire tactical vendors without a coherent strategy, akin to assigning a UPS driver to manage the entire organization's supply-chain logistics.
• Campaigns and marketing efforts become erratic, decimating the ability to compare this month's performance with previous periods due to the inconsistency and incoherence.
• Data collection grinds to a halt, revealing the shortsightedness of hasty "winging it."
• The existing data is left unexplored, a refusal to confront reality.
• Vanity metrics overshadow key performance indicators, prioritizing likes and followers over tangible web traffic, regardless of the cost-benefit analysis.
• Sabotaging the disciplined approach becomes the winger's norm, offering no constructive input and quick to criticize any planning effort.
• "Winging it" serves as a smokescreen, masking underlying issues like a lack of planning prowess, commitment, refinement, and follow-through.

Here's what unfolds for those who "wing it":

• They exhaust their budgets on fleeting social media or short-lived marketing campaigns that lack the sustainable momentum required for meaningful results. Attempting to cross the vast ocean of success in a frail canoe might yield outcomes, but the odds are rarely in their favor.
• They eagerly latch onto trends without discernment. Trends serve as a mask for previous miscalculations, offering a convenient diversion. This is why those who "wing it" are drawn to trends like moths to a flame – a quick switch, a fresh facade, and they believe they've repositioned themselves for success: "We've moved on to this platform now."
• In some instances, they may enlist experts as scapegoats. They cycle through marketing firms like a revolving door, all the while sidestepping the creation and adherence to robust plans. They orchestrate audibles at every juncture, only to assign blame to the marketing firm when things falter. This rinse-and-repeat pattern has become a cliché within the marketing realm.

Those who wing it, dismiss the disciplined work of making plans, setting goals, committing to them, and following through. Wingers have a quitter’s mindset before they start. They'll unconsciously do everything they can to instinctively look for opportunities to wing it, employing every tactic to obstruct, impede, delay, or even undermine a disciplined endeavor. It's a classic evasion mechanism to sidestep grappling with vulnerabilities, commitment hesitations, and the need for structured order.

Preferring to "wing it," they opt to employ disposable tactical vendors, furnish vague directives, and then conveniently allocate blame when things unravel. Refuse to embody this archetype; halt this damaging cycle now.ls. Don't be that person, stop this cycle.

4. Winging It Is Driven By Adrenaline & The Myth of Haphazard Success

Forget the .01% of exceptions that succeed by winging it; the rule is 99.99%. The “ready, fire, aim crowd” not only crash and burn, but they waste company resources in the process. They are as successful as modern jazz musicians. When’s the last time you bought an album? Me neither.

Victory in the digital realm hinges on determination, discipline, commitment, and integrity. If these traits don't resonate with you, the digital arena might not be your stage, as success here necessitates their constant application.

Unfortunately, the most significant casualty in this scenario is the organization itself. The organization emerges as the ultimate loser, unable to secure victories or glean insights. It lacks data, consistent endeavors, and polished strategies to showcase its investments. Regrettably, "wingers" are content with their improvisational approach, heedless of the detrimental impact it has on their goals.

Winning in the Digital Age takes grit, discipline, commitment, integrity and adaptation. If you're weak in these areas, you're in the wrong place, as this journey requires these skills every day over the long haul. People lacking faith in their ability to learn new things, commit to goals, or follow plans, see efforts like this as impossible.

5. Stripping the Ego: Confronting Fear and Taking Control

Admitting to fear is a step toward self-awareness. The digital world teems with opportunities and pitfalls, and acknowledging that a tech-savvy teenager could potentially outshine you with a smartphone and an app can be intimidating. Instead of resorting to "winging it" as a shield, a delayed form of quitting, confront your fears directly. This facade for quietly quitting only veers you off the path to your company's objectives.

Separating your ego from your concerns allows you to focus on the tangible goals of your digital endeavors.

6. Effective Strategies for Confronting Fear: Navigating the Digital Landscape

Instead of derailing your digital strategy or succumbing to fear, adopt more productive coping mechanisms. Consider implementing the following approaches:

• Identify the Wingers: Acknowledge the Tendency

Be candid with yourself and your team. Recognize whether you or others tend to follow plans diligently, refining them as necessary, or whether you're quick to abandon ship and resort to improvisation. Ask yourself: how effective has this approach been for you so far?

• Reflect on Progress: Evaluate What Works and What Doesn't

Pause to assess your strategies objectively. Determine what aspects are yielding results and which ones aren't. If the "winging it" mentality isn't yielding the desired outcomes for your organization, it's time to consider alternatives.

• Introduce a Prerequisite for "Winging It"

For anyone proposing an alternative plan or a significant deviation from the existing strategy, mandate a written plan, complete with a comprehensive cost-benefit analysis and a risk assessment. Present it to the team and seek their buy-in. If the proposed alteration is worth pursuing, it should withstand meticulous scrutiny.

• Whining as a Catalyst for Change: A Surprising Solution

Don't underestimate the power of voicing concerns. Transform complaints into constructive questions or actionable insights. Utilize tools like ChatGPT or journaling to reshape negativity into actionable steps. Embrace the fact that challenges can be daunting, blurring the line between genuine concerns and ego-driven reservations. Whining is acceptable. Quitting is not!

• Harnessing Peer Support: The Group Therapy Effect

Engage in sincere discussions with peers to unearth common fears and concerns. Cultivating an environment of open dialogue fosters mutual support and the sharing of strategies for tackling shared challenges.

• Delve Deeper: "Cups of Clarity" Workshops

Organize focused workshops or create dedicated "cups of clarity" sessions. Engage experts to address apprehensions head-on, capitalizing on education to alleviate uncertainties. Education often serves as the antidote to doubt. By seeking knowledge, you not only dispel your own fears but also enhance your confidence and capacity to steer your digital efforts.

Confronting fear isn't about evading it but about channeling it toward constructive strategies. By adopting these approaches, you'll be better equipped to navigate the intricate digital landscape with resilience and poise. Over time, you will learn how disciplined planning, commitment to

data-driven decision making are in fact superior approaches to winging it.

Conclusion: Evolve with Precision, Not Impulse: Navigating with Nuance

Instead of tossing the baby out with the bath water, or completely abandoning your plans, map and compass, take a sober assessment of the situation. Chances are, amidst the tempest of change, there lie opportunities to recalibrate and adapt your course rather than resorting to spontaneous improvisation or hitting the reset button.

As we traverse the digital wilderness, it's imperative to confront our vulnerabilities, face down our fears, and embrace strategic planning as our guiding light. Within every team, skepticism, cynicism, and half-hearted efforts serve as adversaries to triumph. By boldly acknowledging these shadows and confronting them head-on, we unshackle the potential for triumph that reaches far beyond the initial obstacles.

Always remember, in this realm where bytes and pixels reign supreme, surrendering or resorting to "winging it" is akin to forfeiting the game before it even begins. Discipline, endurance and adaptation are all part of the game. Seize the reins, welcome challenges with a warrior's spirit, and surge forward with the indomitable will to do the formidable work (DTFW) to succeed.