“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. 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:
1. 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 break out in case of emergency. It’s 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.
2. Higher Tolerance for Ambiguity
A group of CEOs and board directors were polled last year about the leadership skills they now consider mandatory to prepare for the next crisis. The top skill cited? Tolerance for ambiguity.
Getting comfortable knowing that you do not—and cannot—know all the variables when making decisions is a skill honed over time. Implementing a pragmatic optimistic mindset shortens the learning curve and provides clarity in the process.
3. Shifting from Reactive to Proactive Leadership
Operating in reactive mode has consequences far beyond tactical or operational decisions. The social upheaval of Summer 2020 showed the exponentially dire consequences of reactive leadership. Legacy brands saw billions of dollars in messaging become irrelevant overnight. Control of the narrative was lost.
Just as actions have consequences, so does inaction. Especially in crisis, indecision is the enemy. Making decisions based on how the world is—rather than how we want it to be—results in forward-leaning leadership that inspires confidence and mobilizes execution.
Know Your Dragon: Why Most People Resist Pragmatism
With so many benefits to pragmatic thinking, it may seem surprising that more leaders don’t embrace it. But the truth is, realistic mindsets run counter to our hardwiring and trigger defense mechanisms.
The top three resistance points I’ve seen are:
1. Basic Instincts Are Primal
Choosing discomfort goes against our instincts. Moving forward with less clarity or more unknowns feels unsafe—even when the outcome is better.
2. Epiphanies Are Painful
The cost of truth is often discomfort. Like diamonds found deep underground, valuable realizations require effort, sacrifice, and pain. Acknowledging malevolence, chaos, and injustice—within organizations, communities, and even ourselves—requires a rare kind of honesty and ownership.
3. We’re Programmed for Blind Optimism
Our culture teaches us to associate “mindset” with feeling good. Anything that threatens that positive feeling is often resisted, even when it’s necessary for growth.
My Journey to Pragmatic Optimism
“You crossed the desert. Did you learn nothing?” — Greg Dulli
In 2015, I hit a personal and professional breaking point. Within five weeks, my business failed, my marriage ended, and my identity collapsed. Every assumption I had built my life on was shattered.
In survival mode, I realized I needed a mindset that could hold both optimism and realism. I didn’t need to believe the sky would never fall—I needed tools to handle it when it inevitably did.
So I went on a three-day solo retreat in the desert. What I discovered there became the foundation for the goal-setting and accountability systems I now use with myself and my C-Suite clients.
Getting real with myself brought clarity, confidence, and—ironically—more hope than before. There was no illusion, no filter. Just truth, and a way forward.
How to Start: The 3 Core Practices
1. Tell the Truth (Especially to Yourself)
“Above all, don’t lie to yourself.” — Dostoyevsky
Be honest with your team, your stakeholders, and most importantly, with yourself. Sugarcoating may protect egos in the short term, but truth builds trust and long-term success.
Start by telling yourself the truth—every day. When you don’t know what to do, start there.
2. Make a List (And Build Filters)
Create a decision-making system that accounts for reality. Your crisis list should include:
- All potential obstacles (even the improbable ones)
- Ways to mitigate each risk
- Immediate actions to begin mitigation
This list becomes your filter for clarity, even in chaos.
3. Create Accountability and Review Systems
“Do what needs to be done. Do it as well as you can. Do it that way all the time.” — Bobby Knight
Once you know what to do, build accountability around it. Set deadlines. Track progress. Reflect with your team. Adjust as needed.
Learn to Tell a Better (More Honest) Story
Leaders must be the steadying force during chaos. One of the most powerful tools I’ve used—and taught—is the creation of story maps: visual representations of your past, present, and future.
Knowing your story brings:
- Emotional Relief – You’ve assessed risks and know what’s in your control.
- Inspiration – Clear-eyed optimism is contagious.
- Focus – When you lead from grounded clarity, distractions fall away.
I’ve built hundreds of story maps with clients. Each one is unique—but the benefits are universal.
The Pragmatic Will Survive (and Thrive)
We live in what I call the New Zero—a post-COVID environment where everything changed. The split between leaders who proactively adapted and those who resisted is growing.
Ambiguity in every domain—economy, supply chain, regulation, culture—can paralyze leadership unless it’s countered with pragmatic optimism.
“You can’t avoid catastrophe, but you can develop yourself to deal with it honorably when it arrives.” — Jordan Peterson
Today, it’s not enough to survive disruption. You must find value in it, grow through it, and lead others to do the same.
Avoid the trap of blind optimism. Escape the paralysis of pessimism. Embrace the mindset that allows you to face facts with courage—and lead with clarity and purpose. That’s the power of being a pragmatic optimist.
