Walk into any motivational seminar, scroll through a LinkedIn feed filled with productivity advice, or sit in a therapist’s office, and you will encounter some version of the same ancient wisdom: the best time to plant a tree was twenty years ago, but the second best time is now. The quote appears on Instagram with serene forest imagery, in business books about overcoming regret, in climate change manifestos, in recovery programs, and in the hearts of people wrestling with the gap between who they are and who they might have become. Its persistence in contemporary culture speaks to something deeply human: the simultaneous weight of past inaction and the stubborn possibility of the present moment.
We live in an age of perpetual self-optimization, where the future is always being mortgaged to perfect some version of ourselves that perpetually recedes. This quote, attributed to Lao Tzu, the legendary founder of Taoism, offers a strange kind of comfort—not the comfort of absolution for past failures, but something more austere: the acknowledgment that regret is real, time is finite, and yet the only moment in which we possess any power to act is the one we inhabit right now.
Lao Tzu remains one of history’s most elusive philosophical personalities, a semi-legendary sage whose very existence scholars continue to debate. According to traditional Chinese accounts, he was born Li Er in the state of Chu during the 6th century BCE. At that time, the Zhou dynasty was fragmenting into warring territories and the moral architecture of Chinese civilization seemed to be collapsing. He served as keeper of the archives at the royal court of Zhou—a position that would have granted him access to the accumulated wisdom of dynasties past. Even so, he witnessed the corruption and artificiality spreading through court politics. Unlike Confucius, his great contemporary, Lao Tzu grew increasingly disillusioned with human institutions and the pretense of social order.
He viewed the court as a theater of false virtue, where ritual substituted for genuine morality and rigid rules replaced the spontaneous wisdom of nature. Unable to bear the hypocrisy any longer, he determined to withdraw from the world entirely. As Lao Tzu traveled westward toward the frontier, the gatekeeper Yin Xi recognized him as a sage. Yin Xi entreated him not to depart without leaving behind his teachings. Reluctantly, Lao Tzu agreed to record his wisdom before vanishing into the wilderness, never again to be found by human eyes. Whether Lao Tzu was a single historical person, a composite of many thinkers, or a literary creation assembled by later Taoist communities may never be definitively settled—but the ambiguity itself feels fitting for a philosopher devoted to transcending fixed categories.
The Best Time to Plant a Tree Was 20 Years Ago
At the frontier gate, Lao Tzu composed the text that became the Tao Te Ching, also known as the Daodejing. This work contains approximately 5,000 Chinese characters organized into eighty-one brief chapters. It is one of the most translated and reinterpreted texts in human history, second only perhaps to the Bible and the I Ching in its cultural reach. However, the quote about planting trees does not appear in the traditional Tao Te Ching, at least not in those exact words. This caveat deserves acknowledgment: the aphorism has been widely attributed to Lao Tzu, yet its precise origins are murky.
It may represent a genuine principle from Taoist thought compressed into memorable form. Alternatively, it may be a modern creation in the spirit of Lao Tzu, born from the need to express Taoist ideas in language that resonates with contemporary anxieties. Various forms of this quote have circulated across cultures and time periods—sometimes attributed to Lao Tzu, sometimes to unnamed sources, sometimes to figures like Confucius or Buddha. What matters is not the archaeological certainty of authorship, but rather the degree to which the sentiment captures something essential from the Taoist worldview. In this regard, the best time to plant a tree was 20 years ago successfully captures that essence.
At the heart of Taoist philosophy lies the concept of the Tao—often translated as “the Way,” though no translation captures its full resonance. The Tao is not a God or a law, but rather the underlying principle of reality itself. It is the spontaneous and nameless order from which all things emerge and to which all things return. To live in accordance with the Tao requires cultivating wu wei, often rendered as “non-action” or “inaction.” A more precise translation might be “effortless action” or “action without forcing.” Wu wei describes the state of moving through the world in perfect alignment with circumstances, without rigid intention or forceful will. A skilled musician does not calculate each finger movement. Water does not strain to flow downhill. A master archer releases the arrow and becomes surprised by where it lands.
This is wu wei. The Tao Te Ching repeatedly uses water as its primary metaphor for virtue: water is the softest substance, yet it wears away the hardest stone; water always seeks the lowest place, and yet nothing can overcome its power. Lao Tzu distrusted the Confucian emphasis on names, rituals, and explicit moral codes. He viewed such constructs as artificial overlays that separated humans from their authentic nature. The best time to plant a tree was 20 years ago—this quote reflects that philosophy perfectly. It acknowledges the irreversible loss of time past without demanding that we crush ourselves with guilt. It presents action in the present not as something heroic or strained, but as the natural, obvious thing to do.
This aphorism carries profound implications about the relationship between time, regret, and agency. The first line acknowledges the way things are—not merely as a statement of fact or cause for despair. Rather, it is acceptance itself. To deny that twenty years have passed, to pretend that the optimal moment is still before us, would itself be a violation of wu wei. It would be a failure to see reality as it is. Taoist philosophy begins with acceptance of what is, not resistance to it. But the second line pivots away from passive acceptance into something more radical: the recognition that the present moment remains the only moment in which transformation is actually possible. This is not cynical.
It does not say that your action today will achieve what action twenty years ago would have achieved. Instead, it offers something subtler: your relationship to time itself must shift. You cannot undo the past; you can only cease struggling against the immutable fact of its pastness. In ceasing that struggle, you liberate energy for work in the present. The tree you plant today will be smaller than it would have been. You will not see its full maturity. But a smaller tree is still a tree, and it is still alive, and it will still grow. This is the Taoist middle way between despair and self-deception, embodied in the wisdom that the best time to plant a tree was 20 years ago.
Understanding What This Wisdom Really Means
Taoism became one of the three great philosophical systems that shaped Chinese civilization for millennia. It operated in constant and creative tension with Confucianism and Buddhism. Confucianism emphasized ritual propriety, social hierarchy, and moral self-cultivation through external disciplines. Taoism countered with an emphasis on spontaneity, harmony with nature, and the wisdom of letting go. Many practitioners viewed these systems as complementary rather than opposed: one might be Confucian in public life, serving the state and following social norms, while remaining Taoist in one’s inner practice.
This inner practice cultivated simplicity and non-attachment. Buddhism, arriving in China around the first century CE, found rich common ground with Taoism in concepts of non-self, impermanence, and the liberation that comes from releasing rigid attachments. Together, these three traditions wove themselves into the fabric of Chinese art, medicine, martial arts, literature, and statecraft. The aphorism about how the best time to plant a tree was 20 years ago speaks to a sensibility that pervades this civilization: patience, long-term vision, ecological awareness, and a humble recognition of one’s place within natural processes much larger than individual ambition.
Western discovery of Taoist philosophy occurred largely in the twentieth century. Various translations and interpretations mediated this process, sometimes illuminating and sometimes distorting the original vision. Arthur Waley’s 1934 translation of the Tao Te Ching was poetic and accessible, though it presented a romanticized version of Lao Tzu as a kind of proto-anarchist pacifist. D.C. Lau’s 1963 translation aimed for greater scholarly precision. Stephen Mitchell’s 1988 version takes considerable interpretive liberties, becoming a favorite among New Age practitioners and business leaders seeking wisdom without the scholar’s apparatus. Ursula K.
Le Guin’s later translation offered a feminist perspective on texts often read through masculine frameworks. Each translation made Taoism available to new audiences, but the process inevitably involved selection, emphasis, and reinterpretation. The quotation about planting trees perfectly exemplifies this process: it circulates widely in contemporary culture precisely because it offers something the modern West desperately wants. It gives permission to stop dwelling in regret and permission to act now—all packaged in the authority of ancient wisdom. It appears in self-help books, on motivational posters, and in business seminars about overcoming obstacles and embracing change. The best time to plant a tree was 20 years ago has become perhaps the most domesticated form of Taoist philosophy in the contemporary English-speaking world.
Why Taking Action Now Still Matters
This quote endures in everyday life because it refuses false comfort on one hand and paralyzing despair on the other. All of us harbor regrets: opportunities we missed, decisions we reversed, time we wasted, years we spent in the wrong career or the wrong relationship or the wrong state of mind. The weight of this accumulated pastness can be crushing. Modern psychology, from Freud onward, has trained us to excavate these regrets, to analyze them, to seek to understand how they shaped us. This has value, but it can also become a trap—a way of endlessly processing the unchangeable past while the present moment slips away. Different wisdom emerges here: acknowledge that twenty years have passed and that you are not where you might have been. Feel the reality of this fully.
Then, having accepted it without resistance, turn to the only ground on which you can actually stand—the present moment. This is not a call to suppress regret or to practice toxic positivity. It is a call to metabolize regret into acceptance, and then to allow acceptance to become the foundation for action. In relationships, it might mean recognizing that you cannot undo years of distance or misunderstanding, but you can reach out today. In careers, it might mean accepting that you cannot recover lost time but you can learn something new this month. In environmental action, it means acknowledging that we have already damaged the climate irreparably, but we can still plant a forest today. The best time to plant a tree was 20 years ago reflects this essential truth.
The philosophy underlying this practical wisdom reflects what scholars of Taoism call the principle of “return” or “reversion”: all things in their extreme age return to their roots, to simplicity, to the uncarved block. After years of striving, of accumulating achievements or possessions or knowledge, there comes a moment when the wise person recognizes the trap. What was gained through complexity and artifice binds us, while what truly sustains life is simpler. The young person full of ambition and regret about roads not taken might benefit from remembering that the ultimate Taoist goal is not to accumulate impressive accomplishments.
Rather, it is to live in harmony with one’s nature and circumstances. The tree you plant today, modest as it may be compared to the forest you might have grown over two decades, is still more real and more valuable than the fantasy of what you would have accomplished in that lost time. This represents a profound reorientation of values: away from maximization toward sufficiency, away from hypothetical perfection toward actual adequacy, away from the tyranny of optimization toward the freedom of good enough.
In our contemporary moment, saturated with information and velocity, the Taoist concept feels not anachronistic but urgently necessary. We are told to be always improving, always optimizing, always grappling with what we should have done differently. Social media amplifies this tendency by presenting curated versions of others’ lives that make our own choices seem inadequate. This quote arrives in this context as a liberating whisper: stop calculating the interest on your lost time. Your neighbor’s tree is bigger because they planted theirs earlier, but that tells you nothing about the value of planting yours today. The second-best time is now—and this second-best is not a consolation prize.
It is the only time that has ever actually mattered, because it is the only time in which human beings can genuinely act. The past is written; the future is still imaginary. Only the present is real, and you have power in this real present moment. This is not a promise that your action today will produce the same results as action twenty years ago would have. It is something more important: a promise that your action today will produce results, and that this is enough. The best time to plant a tree was 20 years ago—and now is the moment when wisdom becomes action.