How to be a Pragmatic Optimist

A real optimist wakes up every morning knowing lots of stuff is broken,
and more stuff is about to break
.” – Morgan Housel

Blind optimism is no longer an option for leaders or individuals who want to thrive long term in a business environment rife with ambiguity, scarcity and rapid change.  

But if optimism were a choice, how would your life and business change? What if you could start each day confident that, come what may, you will not only survive, but thrive?

I believe that option exists—that it is possible to reframe your perspective and expectations, to acknowledge and quantify uncomfortable realities while maintaining a positive mindset and energy. I call this pragmatic optimism.

Embracing a more pragmatic approach to planning and adding a no-BS reality check to your decision-making filters produces clear, measurable results in both individual and corporate growth and sustainability. The top three results I’ve seen include:
Building resilience. A Harvard Business Review article on the topic cited “a staunch acceptance of reality” as the single most important characteristic of both resilient individuals and corporations.

Resilience is not, in my experience, a triage tool to be broken out of a glass emergency case when in-crisis. It is instead a lifestyle. “Toughness is experiencing something that is subjectively distressing, leaning in, paying attention, and creating space to take thoughtful action that aligns with your core values.” – Brad Stulberg

To self-reference one of my past posts, “You are going to suffer. Be grateful.”  Embrace an unfaltering view of your circumstances and get comfortable doing so—it’s how you’re going to survive.

Higher tolerance for ambiguity. A group of CEOs and board directors were polled last year which leadership skills they now consider mandatory to best prepare for and thrive through the next crisis. The number one skill set cited was a tolerance for ambiguity.

Getting comfortable knowing that you do not and cannot know all of the variables that exist when making decisions is a skill honed over time and experience. Implementing a pragmatic optimistic mindset shortens the learning curve and provides clarity in the process.

Shift from a reactive to proactive leadership mindset. Operating in reactive mode has consequences far beyond the tactical and operational decisions made while feeling you have no choice or voice in the conversation. The social upheaval in Summer 2020 demonstrated the exponentially dire consequences of a reactive mindset, as legacy brands watched billions of dollars in messaging campaigns become irrelevant. Control of the narrative was lost, literally overnight in some instances.

Just as actions have consequences, inaction does as well, and they’re just potentially exponential in effect. In times of crisis more so than others, indecision is the enemy. Making decisions based on how the world actually is at any given point in time, rather than how you want the world to be results in forward-leaning leadership which inspires confidence in those tasked with executing your vision.

Know your dragon: Why do most people resist pragmatism?

With so many proven benefits of pragmatic thinking and decision filtering, it may seem shocking that more executives and leaders don’t lean in and embrace the concept. The truth is that “realistic” mindsets like this run opposite to our hardwiring and trigger numerous defense mechanisms as a result. The top three struggles I have encountered with leaders trying to become more pragmatic are:

Basic instincts are primal.  It is contrary to our basic instincts to choose discomfort. That makes it harder to move forward with less clarity or more unknowns than when we’re on a more predictable path with less valuable outcomes.

Epiphanies are painful. Like most things of great value, the cost of attaining treasure iis relative to its worth – diamonds aren’t stumbled upon while casually walking a path, they are down in the mines and securing them requires sacrifice and discomfort. It is no fun to admit and accept the shadow side of positive outcomes. Acknowledging malevolence, chaos, and injustice both in a corporate culture and broader society—as well as within close knit communities, teams, and personal circles—takes a special kind of fundamental perspective on one’s world and rewards self-validation and ownership of that perspective without apology..

We are programmed for blind optimism. The terms mindset, perspective, and worldview have been set as cultural norms to elicit the “up” feelings of traditional optimism. No one hears the term “mindset” and has an instinctive association with proactively making decisions with the potential to threaten that “up” feeling.  Instead, individuals are wired to protect those feelings and devalue anything that suggests they do otherwise.

My personal journey to becoming a pragmatic optimist wasn’t easy.

You crossed the desert. Did you learn nothing?” – Greg Dulli

What sparked my interest and adoption in a pragmatic optimist mindset? Why do I actually care about enough to embrace it myself and share with those around me who rely on my guidance and mentorship?

Back in 2015, I was in crisis and survival mode—literally. In a five week period, my business failed, my marriage abruptly ended as my professional and personal life and identities collapsed simultaneously. My perspective and the global assumptions supported by “proof points” built over the years were not only challenged but destroyed.

In survival and triage mode, I came to the harsh realization of what appeared to be contradicting needs. I had to find a way to possess a positive outlook to start healing and growing again, both personally and professionally, but with a perspective I could trust. I needed a higher degree of confidence that the sky wouldn’t fall—or, rather, to know the sky would eventually fall again, but to possess the tools and resources to mitigate and minimize the consequences of the next crisis.

More importantly, to shorten the time it takes to survive and thrive from those inevitable crises.
To quote one of my favorite takes on an old saying: “What doesn’t kill you will try again.”

To find these answers, I embarked on a three-day solo retreat to the desert. The process I created there, while reviewing what happened and planning my next steps, became the foundation for the actionable goal setting and accountability systems (both internal and external) I now use for myself and with my C-Suite clients. 

In addition to having an actionable plan that was executable moving forward, there were emotional and psychological benefits of change. I was not only more focused on the challenges ahead but inspired and relieved all at once. By getting more realistic, I became even more optimistic and hopeful about my future and outcomes than before, because there was no filter providing false security. I found clarity and comfort in self-honesty.  A high-level overview of that process was posted here.

Show me the way.

With the intention of developing a pragmatic optimistic mindset and leadership profile the obvious question is, how to begin your transformation? While transitioning your mindset and execution style still takes time and experience, there are three fundamental pillars to all of the deeper work ahead on your journey:

Above all, don’t lie to yourself.With respect to Dostoyevsky’s timeless quote, tell the truth—to your team, your stakeholders, and most importantly to yourself. Being honest in your assessment of a given situation may be difficult, and the urge to sugarcoat is strong. This is especially challenging when communicating with investors or clients, as it’s easy to believe that you may lose their advocacy, support, or business if you paint a realistic picture. 

But the truth eventually comes to light, and the negative consequences of not being truthful to stakeholders are almost assuredly worse than any negative outcomes that result from being transparent. It may be hard at first to avoid sugar coating for most people, but it’s simple and easy to remember to be truthful with yourself. Start there. As Jordan Peterson says, “When you don’t know what to do, tell the truth.”

Make a list. Create systems and filters for decision-making, not only for yourself but also to share with key stakeholders when it’s time to ask for their engagement, advocacy and support. At the most basic level, a list of ideal outcomes for you and your business on the other side of a crisis should include:

* All (no matter how improbable) known potential obstacles to your success based on the information available to you at the time;
* Ideas to mitigate the risk of each event on the list;
* Actions that can be taken immediately in service of mitigating those risks.

Create accountability and review processes. “Do what needs to be done. Do it as well as you can. Do it that way all the time.” – Bobby Knight. Once you decide what needs to be done and are committed to doing it, create accountability structures, both to yourself as the leader and to your external stakeholders.

Set realistic deadlines for each action item on your list. At the onset of a crisis, this should be weekly or even daily. Set calendar reminders and schedule stakeholder conversations to reflect on progress, review success metrics, and confirm your next action items—or, when necessary, update or pivot to new action items, refresh the list, and proceed accordingly.

Learn to tell a better, more truthful story.

The health and capability of any leader is paramount in a crisis as they not only need to withstand pressures in order to perform, but they must also inspire and hold together their key team members and customers. Fortunately for those willing to accept the challenge of developing the mindset of a pragmatic optimist, there are overwhelming benefits nurturing both themselves and their stakeholders.

The acquisition of those benefits begins with telling a story. Learn (and learn to tell) your story as a company, leader, and individual. I am a big fan of ‘story maps’—visual representations of the data points that comprise the story of your business and yourself as a leader. There are many formats story maps can take from basic three-act structure to Hero’s Journey or Heroine’s Journey and beyond. 

Knowing where you have been, where you are, and where you’re going is essential in order to gain:

Emotional relief. You will have an honest and accurate representation of your current location on those story maps because you have identified, acknowledged and mitigated risks which allows you to see what is realistically in your control, thereby allowing you to let go of everything else. Hold on tightly to what you deem essential and let go of the rest.

Inspiration. Embracing an honest transparent view of your situation brings a strange and special clarity that helps to inspire confidence in your stakeholders. Clarity also provides you with the emotional and mental bandwidth to be inspirational to others and feel inspired yourself.

Focus.  Confidence that you are making decisions from a realistic perspective allows you to focus on next steps with minimal distraction. Proactive leadership is derived from a mindset rooted in security and serenity rather than vagueness, fear, and scarcity.

I have created hundreds of corporate and individual story maps with clients over the years and while each story is different, the benefits for you and your stakeholders of communicating a crystallized narrative are undeniable and exponential relative to the labor of creating them.

The pragmatic will survive and thrive. 

Too many variables exist in what I call “The New Zero” environment that didn’t as few as two years ago. By this, I am referring to the fracture in a business’ lifeline pre- and post-COVID era.  

In the New Zero, two groups of leaders emerged: Those who proactively took control to build a new foundation of resilience and measurable growth, and those reluctantly dragged their organizations into a new business era without plan or clear perspective. Only one of these groups will survive and thrive.

Whereas in past crises, specific sectors or businesses were hardest hit, this is the first time in at least a century where everyone was affected both personally and professionally, with no ability to forecast with certainty. Even months ahead can be unclear with regards to everything from revenue to supply chain to physical and literal lockdowns.

Ambiguity and risk in the areas of the economy, supply chain, regulation, finance, health, lifestyle, social structures, cultural acceptance, and politics all contribute to hesitation in decision making and ultimately, if unchecked, towards cementing a reactive, scarcity mindset.

You can’t avoid catastrophe but you can develop yourself to deal with it honorably when it arrives.” – Jordan Peterson

Stakeholder relationships are more complex than ever. It is no longer ‘good enough’ to survive a negative or unexpected outcome. Leaders need the capacity to find value in those experiences and not only grow but thrive. 

Those who can emerge from pessimism and avoid blind optimism reap tangible, pragmatic benefits and creative, optimistic but still measurable value for themselves and their stakeholders moving forward.

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