Five Gifts That Upgrade Your Thinking

Can you be grateful for things that make you uncomfortable—even anxious?

Most of us instinctively associate gratitude with pleasant experiences: moments of joy or good fortune. But what if some of the most valuable gifts in our lives are the ones that challenge us, unsettle us, or push us to think differently?

If we define goodness not only as what makes us happy but also as what makes our lives meaningful, successful, and morally grounded, then some surprising experiences begin to look like gifts.

In this installment, I explore a family of gifts that exemplify this kind of goodness.

I call them epistemic gifts. The word epistemic refers to knowledge and understanding, so epistemic gifts are experiences that expand our knowledge, deepen our perspective, and sharpen our ability to think clearly.

Some epistemic gifts are obvious: the education we receive or the skills we acquire that improve our job performance.

But, in this piece, I focus on five less obvious epistemic gifts: critical feedback, self-awareness, wisdom, questions, and what I call the epistemic stretch.

Critical Feedback

The ability to embrace critical feedback as a gift can be difficult—especially when the feedback is poorly delivered. Yet much of our growth comes from people who tell us what we need to hear, not just what we want to hear.

I’ve devoted an entire article to this topic and encourage you to read it.

Self-Awareness

We often devote considerable effort to understanding other people. But how well do we understand ourselves?

Developing self-awareness may be one of the most valuable epistemic gifts you can receive. Consider these three areas:

1. Your motives. Do you know what drives you? We often don’t fully understand why we do what we do. Why do we spend hours obsessing over which photo to post on social media? Why is it so difficult to leave a relationship we know is unhealthy? Questions like these reveal deeper motives, fears, and desires.

2. Your triggers. Have you ever noticed yourself “overreacting” and wondered why? If you are typically calm and easygoing, what explains a sudden burst of anger or frustration? Identifying emotional triggers can illuminate your hidden vulnerabilities.

3. Your coping strategies. What are your default responses when you feel stressed? Are these strategies healthy? Do they serve you well in the long run?

Self-awareness is a gift because it interrupts the autopilot that often governs our behavior. When we step back and examine our motives, triggers, and coping habits, we gain the freedom to make more intentional choices.

Wisdom

Wisdom is possibly one of the most valuable epistemic gifts we can receive.

One of my favorite perspectives on wisdom, advanced by Igor Grossman, focuses on the ability to make sound judgments in complex situations that lack clear-cut answers. This involves integrating multiple perspectives, recognizing the limits of our knowledge, and making more tentative predictions. In short, wisdom requires intellectual humility.

Wise thinkers avoid simplistic slogans or absolutistic rules like “Always be optimistic” or “Never doubt yourself.” In a previous article, I’ve even cautioned against assuming we should simply be grateful for everything that happens in our lives.

Wisdom requires discernment, adaptability, and flexibility. Here’s an example: My father once offered a wise insight: optimism and pessimism are neither inherently good nor bad. Instead, they can be strategically useful depending on the timing of a goal.

When striving toward a desired outcome—such as earning good grades or securing a job—optimism can provide the motivation needed to persist.

But once an outcome is beyond your control—such as waiting for exam results or a hiring decision—optimism becomes less useful. In those moments, a small dose of pessimism can help. If the outcome exceeds your pessimistic expectations, you’ll be pleasantly surprised. And if it doesn’t go your way, pessimism can soften the sting of disappointment.

I’m grateful to my father for this wise advice, which has served me well in my career.

Questions

Closely related to wisdom is the practice of asking the right questions.

Much of our mental energy goes toward searching for answers: what decision to make, what path to choose, or how our future will unfold.

But identifying the right questions may be just as valuable as finding the right answers. Answers tend to be situation-specific, whereas good questions can guide us in many situations.

Here are a few that have been particularly useful for me.

1. To guard against impulsivity, I often ask: “Would my future self, seven days from now, think that what I’m about to say or do is a good idea?” If the answer is no—or I’m unsure—it’s usually a signal to pause.

2. When deciding how to spend my time, I focus on values alignment, not time management strategies. I ask: “Is what I’m doing right now consistent with my values?” If not, what would better align my actions with those values?

3. When I previously served in a leadership role, I often asked questions like: Who benefits from this policy? Who doesn’t? Who receives the most attention, and who deserves more? Which groups might be systematically excluded? These questions helped me become a more inclusive leader.

What guiding questions have helped you make better decisions?

Epistemic Stretch

How open are you to engaging with viewpoints that challenge your deeply held beliefs? When you encounter such perspectives, are you disgusted or curious?

Here, I introduce a term: epistemic stretch, which occurs when you seriously engage with an alternative worldview that differs from your own.

Sometimes an epistemic stretch leads you to change your mind—at least partially.

But an epistemic stretch could also mean making a genuine effort to understand another perspective deeply—not to refute it, but to grasp it as its proponents see it.

Of the five epistemic gifts discussed here, this one may be the most challenging. When we’ve deeply held views on politics or religion, it’s tempting to assume those who disagree with us are foolish or malicious.

But an epistemic stretch leads you down a different path.

When we genuinely try to understand opposing viewpoints, we strengthen our critical thinking, develop intellectual flexibility, and become less self-righteous. We may even reach a point where we can say: “I disagree with this view, but I understand how someone could arrive at it.”

In that sense, an epistemic stretch does more than improve your thinking—it deepens your empathy.

If you want to cultivate epistemic stretches, here are three suggestions.

First, go directly to primary sources. Often, we think we understand opposing views because we have read critiques of them. But what we actually possess is a caricature. To understand a viewpoint fairly, read the original works of people who hold those views.

Second, beware of outgroup homogeneity bias—the tendency to assume members of an outgroup all think alike. Exploring the diversity within a worldview you oppose can enrich your understanding. Start by learning about less extreme viewpoints within a worldview, and you might find, surprisingly, that these can enrich your thinking.

Third, build authentic friendships with people who hold different beliefs. When genuine relationships develop, conversations about difficult topics become opportunities for learning rather than debate.

The Takeaway

Let’s return to the list of epistemic gifts: critical feedback, self-awareness, wisdom, questions, and epistemic stretch.

You may realize that some of these gifts are already present in your life—you simply haven’t recognized them as gifts. Perhaps a challenging experience pushed you to reflect more deeply about yourself. Maybe a mentor asked a question that changed the way you think.

Take a moment to reflect on the people or experiences that allowed these gifts to take root in your life. These are reasons for gratitude. If someone helped you become more self-aware, wiser, or more intellectually flexible, let them know. Thank them.

At the same time, you might notice that some of these epistemic gifts are not yet fully present in your life. Consider this an invitation to cultivate them.

Seek out feedback that sharpens your thinking. Ask questions that challenge your assumptions. Become curious about viewpoints that differ from your own.

These experiences may feel uncomfortable at first. But they expand your mind, deepen your empathy, and strengthen your ability to navigate a complicated world.

In the long run, they may become some of the most valuable gifts that deserve your gratitude.

This is the 6^th article in a mini-series on the Varieties of Goodness.

If this article resonated with you, you may also enjoy my Psychology Today blog Gratefully.