Premeditatio Malorum: A Founder's Guide to Negative Visualization and Building Resilience

Premeditatio malorum is a Stoic practice, the Latin phrase translates roughly as "the premeditation of evils," and it has been used by philosophers from Seneca to Marcus Aurelius as a tool for building resilience in the face of difficulty. It is also one of the most powerful daily practices I have found for helping founders and CEOs reset their perspective when anxiety and goalpost-chasing are running the show. In this piece I want to share exactly how I use it, and how you can too.

The Problem: How to Be More Resilient Without Just Enduring More Suffering

In the startup community, we often speak of resiliency as one of the key ingredients of being a successful entrepreneur. But nobody talks about how to actually become more resilient. The most common strategy I see in my many weekly conversations with founders and CEOs is to endure the suffering. The inherent belief seems to be “If I can only continue to suffer, eventually I will become more resilient.”

That strikes me as a tough setup.

In my own time as a CEO, and now in my work as a coach, what I have found more helpful is to experiment with daily practices that help to reshape the way I, or a client, hold the circumstances at hand.

Negative visualizations, rooted in the Stoic practice of premeditatio malorum, are one of the most powerful daily practices I have found for building resilience and optimism in the face of difficulty.

Here is how it works.

The Founder's Superpower (and Its Dark Side)

I see in many other founder-types a superpower I too possess. Like most superpowers, this one comes with a dark underbelly.

The superpower is to look at any market, product, or situation and quickly assess areas for improvement. It is this vision that allows us as entrepreneurs to envision the world as it might be rather than as it is. These insights enable us to build products and services the world does not yet have but from which it would benefit.

The dark underbelly here is the suffering this ability frequently causes in our lives. I will illustrate with my own.

In my work, for as long as I can remember, I have been plagued by a feeling that I am way behind where I ought to be.

Because I can see how things might be in another year or two, I look at today and deem it a failure. By extension, I look at myself and deem myself a failure.

I do the same thing in my life.

Left to my own natural instincts, I will spend only minutes a day enjoying the many wonderful parts of my life. By contrast, I might spend hours each day agonizing over the parts I wish were different.

In short, both in work and life, rather than celebrating what I already have, or what I (or we) have already achieved, I continue to move the goalposts. I tell myself, or historically also my team, that now is not the time to celebrate. The celebrations can come later. (But of course, because I keep moving the goalposts, later never comes.)

Sound familiar?

What Is Premeditatio Malorum? The Stoic Root of Negative Visualization

The Stoics believed that one of the most reliable paths to contentment was to vividly imagine losing the things you currently have. Marcus Aurelius did this with his family, his health, his empire. Seneca wrote extensively about the practice of imagining worst-case scenarios, not to cultivate dread, but to cultivate gratitude for what already exists.

Premeditatio malorum is often confused with catastrophizing or pessimism. It is neither. The distinction is intention and direction. Catastrophizing is involuntary and future-focused: "what if everything goes wrong?" Premeditatio malorum is intentional and present-focused: "what if I were to lose what I already have?" The first amplifies anxiety. The second reliably reduces it.

This is the practice I bring into my own morning routine and into my work with founders and CEOs who are building resilience at work.

The Two-Column Exercise: A Daily Practice for Building Resilience at Work

I have written at length about my personal morning practice and its value for leaders. This practice is an addition I reach for specifically when I am feeling deeply stuck in the problems at hand and out of touch with the wins or positive parts of my work or life.

The practice is negative visualization, or premeditatio malorum in its Stoic form. Some meditation teachers use it as a future-scenario exercise. I prefer to use it anchored in the present.

Here is the exact exercise, step by step:

1. Open a blank document or notebook and draw two columns.
2. In Column 1, list every "What if" you can imagine that would make your life or work dramatically worse than it already is. Examples: "What if I had not met my partner?" "What if my kids had not been born healthy?" "What if I had not found work I find meaningful?"
3. In Column 2, list the things you most wish would change, but frame each as a "What if" that invites the possibility that the change is inevitable and outside your control. Examples: "What if my son is being exactly who he needs to be right now?" "What if I will naturally and inevitably become a wonderful coach over time?"
4. Read each list two or three times, slowly.
5. In the following days, return to the lists for one or two minutes each morning.

That’s it! It is that simple.

Let’s talk about what we are actually doing here and what makes it so effective.

Negative Visualization vs. Pessimism: An Important Distinction

Why Expanding Your View Changes Everything

When you watch a soccer match, each player on the field inevitably has a zoomed-in experience of the game. She experiences the game only from her corner of the field and only from her personal field of view.

By contrast, the coach on the sideline and we in the stands or behind the television have a much broader field of view.

When we goalpost ourselves or our teams, we are often like that player. We are so zoomed in on the current change we would like to make that it is impossible for us to see the broader field of play or our broader life.

In life, speaking from experience, this causes us suffering often in the form of anxiety or self-criticism.

As leaders, when we fail to see the broader field of play, and when we fail to anchor ourselves and our teams in the broad successes and reasons for optimism, it is easy to fall into despair. This often leads to cultures where we never celebrate the wins because there is always more to do, and it does not take long before burnout comes knocking.

Building resilience at work, for most founders, is less about toughening up and more about learning to see more clearly. Premeditatio malorum is a tool for that clarity.

If you want to explore how practices like this fit into a broader morning routine designed for high-performing founders, you might find it worth reading about a morning routine for founders and CEOs.

I would love to hear how this practice resonates for you as you give it a try.

Part of owning our superpowers as founders is learning to control them and use them for good. If you find yourself spinning at times because all you can see is your work or your life as you wish it was, you are not alone.

The good news is, there is hope. We can learn to leverage our abilities for good and also how to protect ourselves and our teams from the dark underbelly.

And if the anxiety and self-criticism are running deeper than a daily practice can reach on its own, it might be worth exploring what navigating founder burnout looks like with real support.

Wishing you peace on your journey today.

-Matt

If now is the time to explore CEO coaching or a founder peer circle, reach out here.

Frequently Asked Questions

What is premeditatio malorum?

Premeditatio malorum is a Stoic practice whose Latin name translates roughly as "the premeditation of evils." It involves deliberately imagining the loss of things you currently have, your health, your relationships, your work, as a way of cultivating gratitude and resilience. Stoic philosophers including Seneca, Marcus Aurelius, and Epictetus all practiced and wrote about versions of this exercise. It is distinct from catastrophizing because it is intentional, present-focused, and designed to reduce anxiety rather than amplify it.

How does negative visualization help with building resilience at work?

Negative visualization builds resilience at work by disrupting the goalpost-moving pattern that is extremely common among high-achieving founders and CEOs. When you can only see the gap between where you are and where you want to be, you experience chronic dissatisfaction and anxiety. The two-column negative visualization exercise deliberately widens your field of view, anchoring you in appreciation for what already exists. Over time, this rewires the default toward gratitude and perspective, which are the foundations of genuine resilience rather than just endurance.

How is premeditatio malorum different from pessimism?

The key difference is intention and direction. Pessimism is involuntary and future-focused, "what if things go wrong?" It amplifies fear. Premeditatio malorum is intentional and present-focused, "what if I were to lose what I already have?" It cultivates gratitude. Catastrophizing is something that happens to you. Premeditatio malorum is something you choose to do, for a limited time, with a specific purpose. Practiced regularly, it tends to reduce anxiety rather than increase it.

How do you use negative visualization as part of a morning routine?

The simplest version is the two-column exercise described in this article. Set aside five to ten minutes, ideally in the morning before your day gets loud. In Column 1, write "What if" scenarios that would make your life dramatically worse than it already is, to cultivate appreciation. In Column 2, write "What if" reframes for the things you most wish were different, to cultivate acceptance. Read both columns slowly. Return to the lists for one or two minutes each morning for the next several days. The cumulative effect tends to be a quieter, more grounded relationship with the present.