The Power of Letting Go, 2040’s Ideas and Innovations Newsletter, Issue 178

Kevin Novak
8 min readSep 19, 2024

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Issue 178, September 19, 2024

The Autumnal Equinox has made its annual appearance, and if you are anything like us, the change in seasons is bittersweet. On a simple level, we are leaving the sentimental idea of happy, sunny, summer days behind as we cross the bridge to winter’s edge. If we’re more realistic, we have to admit that the Summer of 2024 was the fourth hottest on record, and by August 15, 29,917 fires burned more than 5.2 million acres. It was also a time when it was nearly impossible for first-time homeowners to buy houses and food prices went through the roof. In happier news, Deloitte’s financial well-being index rose for the third month in a row in July, reaching a four-year high of 102.6.

Deep Reflection

But we’re thinking deeper and more focused on what we choose or are forced to let go of when things change. And note that we are based in the Northeast, so our bias is definitely fixed on the four-seasons model. Aside from stowing our summer gear, water sports equipment and nostalgia for 15 hours of sunlight each day, there is a non-specific seasonal sadness about saying goodbye.

Parker Richards writes in The New York Times, “No matter how much we love autumn, a seasonal change can be a time for reflection. We mull over what we’ve experienced, what we’ve lost, and what we’ve gained. We think about our own choices, and how we’ve dealt with another few months of life. The year is more than half-done, after all.” He cites author Cody Delistraty who observes that “the end of summer is a space for grief, not the intense, soul-racking kind that comes with the loss of a loved one, but the kind that comes with reflection.” Going further there may be a sense of grieving “about how we may have failed to achieve what we wanted with the season,” says Richards.

Organizational Workforce Grief

We know something about grieving as it applies to business and organizational transformation. We have written in our strategic playbook, The Truth About Transformation, about the fear of letting go and facing an unknown future, particularly changes that challenge an individual’s concept of their work selves and how they contribute. In short, the role they play.

Transition in an organization, very similar to how we seek to manage a personal transition, is a process that requires significant work — and reflection. For leaders and change agents seeking to transform an organizational construct and its related systems, they must recognize they need to apply significant energy, thought and plans to get the individuals within a workforce to be comfortable with change. And acceptance of change is not easy. Stefan Lehner, a coach, and educator based in Paris created a transformation curve from William Bridges’ Transition Model (created in 1991) to illustrate the grieving journey as it pertains to business. It’s a useful paradigm for leaders to adapt to ensure they are leading change, not forcing it, and knowing how to let go in a healthy way.

We wrote several weeks ago asking, “Does substance always matter?” We propose that there are some rare instances across society as well as organizational transformation and change when a leader is so dynamic and inspirational in their communications — or, individuals are so hungry for a vision of the future that embraces optimism and possibility, that they need little if any substantive detail to align everyone.

Most organizational change and transformation are only going to be successful if there is substance that focuses on helping individuals across the workforce to identify and redefine themselves and their roles while recognizing the importance of advocates for organizational change. If the advocates and leaders do not recognize the human factors at play and still believe trickle-down, command-and-control, “just do it” tactics will work dooms the effort from the start.

More on Grief’s Correlation to Change

On paper, grieving looks straightforward, and the phases of the process and recovery make sense. At the same time, we all know from personal experience that going through such a journey can be intense in business life. It can trigger emotional issues such as fear, anger, and holding onto legacy beliefs. It can also prompt tunnel vision in refusing acceptance or even consideration of the positive potential of the change(s).

To make it more complex, resistance is typically held at a subconscious or unconscious level, often unrecognizing where the fear, anger and anxiety have their roots. The inherent attributes of being human make it difficult for us to identify the source of grief, openly discuss it, then release it and adjust.

The grieving journey (letting go and acceptance) starts with the introduction of transformative change and passes through each employee’s personal stages of denial, anger, sadness, rebellion, and fear. Negotiation with oneself and others precedes acceptance which then unlocks new patterns and activation. All these steps lead to redefining individual roles and the acceptance of oneself in the professional setting.

The transformation curve is illustrated below.

Source: (Lehner, Stephen. (Nd).

It’s one thing to experience this curve personally if you are dealing with a crisis like death or a divorce, but it’s altogether another to mobilize an entire organization to be in alignment and work through change management. The organizational experience of letting go is in a meta way, a sense of grieving with the aspiration of gaining acceptance and activation for a better future.

But to put the grieving experience and what we let go of in a business context, we believe that we don’t let go often enough. We hold onto things that no longer work at a 100% level. By nature, we often seek out the familiar. We stick to what is known and comfortable. We prefer a routine with predictable execution and mechanical repetition requiring little deep thought. Human nature is driven to conserve energy at every turn.

As such, we don’t clean out our emails and digital files often enough, and we don’t let go of systems and processes that have become irrelevant or irresponsible. We grab onto the past as an explanation for the decisions we make in the present, often preferring a past that we remember as more comfortable. And we often defer to the past even if it is no longer applicable now or the near future. We make the same mistakes over and over and excuse them as coincidence, we live in complete denial, or believe it is someone else’s fault.

Every individual bears a responsibility to hold themselves accountable to ensure when transitions are needed, they recognize, thoughtfully consider, and embrace them.

The Power of Letting Go

If you are stuck and holding on instead of moving away from a challenge that has created dysfunction and disruption, the warning bells should be ringing to pause, step back and evaluate the situation. Ask yourself why you aren’t letting go. Author David Specht writes on LinkedIn and advises a three-step letting-go analysis:

  • What is the long-term impact? “Will this problem still hold significance in a year’s time, or is it a temporary hurdle?”
  • Assess the damage. “Consider the long-term repercussions of prolonged conflict. Is it causing irreparable harm to relationships or the business’s reputation?”
  • How does it affect your professional image? “Reflect on how your handling of the conflict reflects on you as a leader. What impression does it leave on your peers, superiors, and team members?”

And we would add the following:

  • What is my fear? Where is my anxiety coming from?
  • What do I need to know and understand to envision my new self?
  • How can I redefine myself to ensure I am professionally growing and letting go of what I need to let go?
  • Can I rise to the occasion and be part of something bigger and better?
  • How can I contend with ambiguity?
  • How can I embrace reflection?
  • How can I be honest in identifying the impediments that prohibit me from accepting transitional change?

The key to letting go is to recognize “when a situation is not worth the ongoing stress and tension. Be prepared to make the difficult decision to move on for the sake of your mental well-being and the overall health of your business,” Specht adds.

Pick Your Battles

When should you pivot? When do you move on? How do you let go? Take a page out of self-realization philosophy to “empower yourself to focus on what truly matters.” Specht adds, “Not every battle is worth fighting, and not every setback is a defeat. Embrace change, adapt to challenges, and keep moving forward. The key is to stay true to our principles and lead with integrity, no matter the circumstances.”

No Regrets

The idea of no regrets can be complicated. Cornelia Channing writes in the New York Times that having no regrets “Seems like a bit of wisdom. After all, regret is a dirty word. It suggests a dark, anxious way of looking at the world and calls to mind sleepless nights spent stewing over past mistakes. Who wants to live that way? Wouldn’t it be better, and healthier, to simply move on? No regrets. It’s a nice idea. But is it real?” Whether it’s real or perceived, Channing says regret could teach us something.

As it turns out, writer Daniel Pink believes there is power in regret “and that it should not be thought of as something negative and shameful, but rather embraced as something helpful and instructive. What we regret, can teach us about who we are. It helps to reveal what we want, what we fear, what truly matters to us and what doesn’t. It is an emotion that can help us tune our moral compasses, strengthen our values and keep us from repeating the same mistakes over and over again.”

Embracing Human Defaults

At 2040, we are proponents of learning from the past and not holding it so tightly that it inhibits us or pulls us back deferring change for comfort. We each play a role in an organization comprised of a collection of individuals who all have their own sets of beliefs and outlooks. But remember, we are more the same than we are different. And fundamentally we react in similar ways within individual variations.

We each step through the phases of transition regardless of our professional and personal situation. As leaders, change agents and proponents of transformation, we must all embrace the power of letting go, learn how to aid others in the transitional process, recognize the role of grief and find the path to activation.

If you want to learn even more about embracing transitions in organizational change and transformation. Get your copy of The Truth About Transformation.

Explore this issue and all past issues on 2040’s Website or via our Substack Newsletter.

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Kevin Novak

4X webby winner, CEO and Chief Strategy Officer @2040 Digital (www.2040digital.com), IADAS Member, Speaker, Author, Science Nut