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Cliff Was Working Hard. So Why Did He Keep Destroying Everything He Built?

Cliff was tired. Tired of trying. Tired of beginning. Tired of explaining. Tired of watching other people’s lives seem to move forward while his seemed to circle the same drain.

He started a printing business. It failed. He tried selling clothes. That failed too. Then he opened a barbershop. A few months later, that was gone. Each failure seemed different on the surface. Different product. Different customer. Different location. Different excuse. But beneath them was the same man. And the same beliefs.

Unfortunately, Cliff couldn’t see that yet. All he could see was evidence that things didn’t work for him, that people didn’t support him, and that some people were simply born with advantages others would never have. And perhaps his father had been right all along.

“MEDIOCRE.”

Cliff was twelve when his parents separated. Until then, life had been reasonably predictable. His family was middle-class. There was food. School fees were paid. His mother cared deeply for him. His father was present, though “present” was not necessarily the same as emotionally available.

His father was imposing. Authoritarian. Certain. There were rules. There were standards. There was a right way to do things, and usually his father knew what it was. Anything below that was labeled mediocre.

Then the marriage broke. With it, something in Cliff’s understanding of the world broke, too. Suddenly, there wasn’t enough. The three older children had already left home to build their own lives. Cliff remained with his younger sister and his mother, watching the family structure he had assumed was permanent disappear. He did not have the language for what was happening inside him, so he made sense of it. Children do this remarkably well.

They rarely say:

“My parents are two complicated adults whose relationship has broken down for reasons that may have very little to do with me.” The mind prefers simpler explanations. People leave, and security disappears. Don’t depend too much on anyone. You are largely on your own.

Cliff couldn’t have put those beliefs into words; he only lived by them. Then high school arrived, and for the first time, freedom felt intoxicating. No father watching, no constant commands, no one asking where he had been every minute. There were friends, alcohol, girls, and the exciting chance to become someone different.

Unfortunately, the girls did not cooperate with the transformation. Cliff was rejected, then rejected again. At first, he laughed about it with his friends, but repeated rejection gradually ceases to be just an event. The mind begins to integrate it into his identity, shifting his perception from hearing: “She isn’t interested” to “There is something wrong with you,” then to “Women don’t want men like you,” and finally to “Women are the problem.”

Notice what had happened. An experience had become a story. The story had become a belief. The belief had begun to shape behavior. And the behavior would soon create more experiences that seemed to prove the belief.

Cliff became increasingly resentful, guarded, and desperate for approval. Ironically, this made him less appealing to those he sought approval from. He was unable to recognize this cycle, as most of us cannot see such loops when we’re inside them.

THE WORD WRITTEN IN RED

His final high school results were unimpressive. His father looked at them and delivered his judgment. “Mediocre.” Perhaps his father meant the grade. Cliff heard that description of himself. Years later, whenever he attempted something difficult, the word appeared in his mind.

MEDIOCRE.

Written in blood red, not ink, he sometimes suffered from severe headaches and retreated to his bedroom. One day became two, then several, until eventually Cliff would emerge and carry on. To others, he appeared as a young man lacking discipline, but internally, something more complex was occurring. Cliff yearned to succeed, yet success required being tested. Being tested carried the risk of failure, and failure meant confirming his father’s judgment.

One part of him pushed for success, while another secretly prevented him from discovering his true abilities. That hidden side was exceptionally clever. It didn’t simply tell him not to start a business, as that would have been too obvious. Instead, it encouraged him to start but without sufficient research. It urged him to start, then take criticism personally. It promoted choosing the cheapest options, even if it meant sacrificing quality. It advised withdrawing when things got tough, avoiding long-term learning. It suggested blaming external factors — like the economy, customers, competition, capital, connections, or upbringing — when failures occurred. Ultimately, when the business failed, he would claim, “You see? I tried.”

That is one of the most misleading forms of self-sabotage: movement without genuine commitment. You might be very busy, yet still cling to the very belief you’re trying to break free from.

SOMETHING TO MAKE THE NOISE STOP

Pornography appeared gradually, not as a statement or act of defiance but as a form of relief. For a few moments, Cliff could escape rejection and immerse himself in a different world. Later, alcohol and marijuana fulfilled the same role — they changed his mood without requiring him to make changes in his life. That was important because his life was painful.

One afternoon, he met an old friend from primary school. The friend listened. Really listened. There was no lecture, no fatherly judgment, no talk of potential. He simply seemed to understand. Then he introduced Cliff to marijuana.

The initial experience was extraordinary. For the first time in months, maybe years, Cliff’s thoughts settled into silence. The red word vanished. No more mediocre, no father, no failed ventures, no women turning him down, and no anxiety about the future. Only distance remained.

Cliff had not found peace. He had discovered temporary absence.

However, after enduring emotional noise for so long, absence can be mistaken for peace. He soon started smoking regularly with a small group of young men. And something else changed. They engaged in conversations — not superficial, but deep and raw. These were the kinds of discussions many young men rarely have. They talked about fathers, money, women, government, wealth, opportunity, corruption, failure, and life’s unfairness. Some ideas echoed Robin Hood, others sounded Marxist, and some drew from Rastafarian philosophy. Some were just angry young men trying to understand why life seemed easier for others.

Their conclusion was straightforward: the system was corrupt. Wealth was concentrated among the rich, while the poor had too little. Consequently, taking from the wealthy was not theft but correction. Cliff appreciated this argument, not because he scrutinized its reasoning, but because it eased a burden — responsibility.

If the game was completely rigged, his failures required no deeper examination. He did not have to ask why customers disappeared. He did not have to examine his discipline. He did not have to confront his fear of rejection. He did not have to admit how often he abandoned things. He had found people who could turn his disappointments into ideology.

And yet sometimes, when the marijuana wore thin and everyone became quiet, another voice appeared. Cliff… what if you haven’t found truth? What if you’ve simply found an echo? He would take another puff.

THE FIRST JOB

Initially, Cliff declined when they invited him to join a “job,” making up a reason. The second invitation was more difficult to refuse because he owed his dealer money for marijuana. Shame has a curious way of wrestling morality into complex issues. Eventually, they went out.

Cliff saw three young women lose their phones — an iPhone, a Samsung, and another costly device. It all happened so fast, almost too fast. That evening, inside a run-down single room, the men laughed as they counted their stolen phones scattered around them. Cliff looked at the devices. Each one was worth money, yet each also represented something more — someone’s photos, conversations, work, savings, or someone frightened on a street elsewhere. His stomach clenched at the thought. Suddenly, he heard a voice — not his conscience but his father’s. Mediocre.

He drank, but it didn’t help. He smoked, and the marijuana seemed strangely weak. Eventually, he was handed his share — twenty thousand shillings. Cliff looked at it, more cash than his failed businesses had earned in weeks. This was a dangerous sign — maybe it actually worked. By the next evening, much of the money was already gone. There was a girl he liked, drinks, a party, laughter. For one night, Cliff felt like the successful man he dreamed of being. The money wasn’t just capital anymore; it was a form of anesthesia. When the money vanished, so did the feeling. Despite vowing to stay away from the gang, Cliff found himself coming back.

AND THEN IT HAPPENED

The plan seemed straightforward: one motorcycle, multiple locations, quick movements, phones to be taken, then vanish. Cliff would serve as the lookout. They selected a busy area, which should have intimidated them. However, their past successes had bred overconfidence. Success often blinds. One phone turned into three, then six, and finally ten. The bag next to Cliff grew heavier, and so did the men’s recklessness.

Then one of them grabbed a woman’s phone. She screamed. They tried to intimidate her. One slapped her. The woman was known in the neighborhood. A man nearby rushed to help. The young men fought back.

They were unaware he owned a local gym or that others knew him. They underestimated how fast a crowd could change. The motorcycle wouldn’t start, and the three men ran, but they didn’t get far.

Cliff kept his distance, clutching the bag, as chaos erupted around him. People began shouting and hitting each other, blocking his view. Paralyzed, he stood frozen, every instinct urging him to run. Then, suddenly, clarity struck — he knew what was happening. Without hesitation, Cliff sprinted, pushing himself until his lungs burned. He dodged into an alley and vomited, remaining bent over for what seemed like an eternity.

When he finally looked back at the chaos, the three young men he had sat smoking beside him only hours earlier. The smell reached him before the full situation sank in. Cliff ran once more.

THIRTEEN DAYS

He couldn’t later recall how he got to his mother’s house. He remembered a gate, a wall, and hearing his mother’s voice somewhere. Then everything went dark. He stayed locked inside his room. Days passed — one, two, five, eight — without change. His mother knocked, but he hardly responded. His food remained untouched.

His mind kept replaying the scene repeatedly. Beneath the horror, a quieter, more troubling thought lingered: that it should have been him. If only he had stood twenty metres differently, or if someone had seen him with the bag. Maybe one of the others had pointed him out. Perhaps he had crossed at the wrong moment. That fourth body could have been his.

Cliff had long complained about life’s unfairness, but now he faced a different kind of unfairness — being alive while they were not. He had no explanation for why this had happened.

By the thirteenth day, Cliff felt physically weak after only drinking the water left outside his door. However, his thinking had started to change — not because his problems had vanished.

Trauma doesn’t automatically lead to wisdom. It doesn’t. Sometimes it destroys people, and other times it leaves wounds that take years to heal. However, Cliff started asking a different question — not: “Why has life done this to me?” but: “What am I going to do now that I am still here?” That shift in perspective transformed the atmosphere in his room.

THE PHONES

Then Cliff remembered the bag. The phones were still inside, turned off and concealed. He stared at them for a while. This wasn’t legitimate money. There was no noble explanation. No matter what story he constructed, those phones had been taken from innocent people.

Eventually, he reached out to someone he knew who purchased such devices. By the evening, he was holding close to two hundred thousand shillings. As he sat on his bed, he stared at the money. It didn’t feel like wealth; it felt burdensome. He was aware of its origin and what had happened to the people he had been with. Cliff made a decision — perhaps imperfect or morally questionable — but it marked a psychological shift.

He said aloud, “I’m going to make something of myself,” repeating it. “I don’t care how many times I get rejected,” his voice trembling. “I’m going to learn.” Then came a pivotal moment: “I am going to stop blaming everybody.” Unaware at the time, this simple declaration would transform much more than his business. When blame leaves, responsibility has somewhere to sit.

SAME MAN. SAME BUSINESS. DIFFERENT MEANING.

Cliff resumed printing, returning to a business he had previously failed at. He bought a suit, printed business cards, and began visiting offices. The old Cliff would stand downstairs, glance at the security guard and glass doors, imagine being dismissed by reception, and hear the manager saying no. Feelings of MEDIOCRE would fill his mind before he would leave.

The new Cliff still felt fear, but its significance shifted. Previously, fear indicated to stop; now, it signals that something matters. Rejection used to mean I was not good enough, but now it suggests not yet, not here, or not this person. Discomfort no longer meant something was wrong; instead, it became part of the cost.

Cliff was unaware that something extraordinary had occurred. The outside world remained mostly the same, but his internal understanding had shifted. This change in perspective influenced his behavior.

KNOCK ONE. No response. Knock two. Still nothing. Three. “We already have someone.” Four. “Leave your card.” Five. Silence. The familiar, dull voice returned. For a moment, Cliff hesitated on the pavement. He could just go home. No one would blame him. Five rejections should be enough, right? But then a new word emerged: Courage.

He crossed the road, approaching another office with its door and new opportunity. He knocked six times. The man inside listened attentively and asked questions. Then he inquired, “Can you do this?” Cliff almost responded immediately but instead examined the work. “Yes,” he said. “When?” “Tomorrow.” The client nodded in agreement.

Cliff left the office with his first meaningful order in months. Outside, he looked at the paper again — nothing extraordinary had occurred. There were five rejections and one acceptance. However, six months earlier, Cliff might have let the first rejection explain the other five before they happened. That afternoon, rejection had become information rather than identity.

THE FIRST SACRIFICE

Cliff faced a new choice: deliver the next day as promised or finish the work immediately. The old Cliff preferred comfort, but the new Cliff was increasingly intrigued by sacrifice — not suffering for the sake of suffering. Sacrifice as a trade. What must I give up to produce what I say I want?

He avoided the easy evening. He found a printer. Then he encountered another familiar temptation — opting for the cheaper option. Someone else could do the job at a lower cost, with better margins. However, the quality might suffer. Old Cliff would have accepted the lower margin, convincing himself that customers only valued price. If the client then complained, Cliff would blame the client for being “difficult.”

This time, he chose quality. He stayed until the job was complete. Rather than waiting until morning, he returned to the client’s office. The man was closing up. He looked surprised. “You’re back?” “Yes.” “But you said tomorrow.” “I finished.”

The man examined the work, paused, then looked again. Cliff’s heart started pounding. Suddenly, the familiar story resurfaced: He doesn’t like it. You’ve messed this up. You are — 

“This is very good.” Cliff almost did not understand the sentence. The man smiled. “Before I go, here is your money. Come tomorrow. I have more work for you.” Cliff walked outside, holding the payment. He stood completely still. Something had happened that felt strangely unfamiliar. A client was happy with him.

WHAT IF THE CLIENTS HAD NEVER BEEN THE PROBLEM?

That night, Cliff couldn’t sleep. This time, it wasn’t due to marijuana, alcohol, or anxiety. He was just thinking. For years, he had convinced himself that customers were difficult, demanding, unreasonable, and unappreciative. But now, something about that explanation felt unsettled.

This client had responded warmly. Why? Cliff reflected on the day. He listened attentively, delivered earlier than promised, prioritized quality, and valued the customer’s order. Then, an unsettling thought arose: what if the clients were responding to what he provided? This realization was more painful than blaming them, because if the customers influenced his failures, he was a victim. However, if his own actions contributed to the pattern, he bore responsibility.

Responsibility is terrifying. But it also holds power. He began remembering past customers. Calls he had ignored. Deadlines he had stretched. Complaints he had taken personally. Corners he had cut. The coldness he carried into conversations because he expected rejection before it arrived. Suddenly, he saw it.

He had approached clients as though they were judges, making every request seem like criticism, every question suspicious, and every correction feel like rejection. No wonder he resented them. He had never viewed himself as just serving a customer but had repeatedly stood before his father, waiting for one word: mediocre.

The business had not only been a business. It had become a courtroom in which Cliff’s worth was permanently on trial. And every time he feared losing the case, he sabotaged the proceedings.

SIX MONTHS

Nothing transformed overnight. There were bad weeks. Late payments. Clients who disappeared. Orders that went awry. People who promised work and never called. But something was different.

Cliff stopped interpreting every setback as prophecy. When a customer said no, he asked why. When a job went badly, he studied what had happened. When he didn’t understand something, he learned. When another business seemed more successful, he stopped asking immediately what unfair advantage they had. He began asking: “What do they understand that I don’t?” That single question changed the kind of information his mind looked for.

Previously, he searched for signs of unfairness. Now, he sought evidence of opportunity. Same world, but a different perspective. He read extensively, watched business videos, and spoke with printers more skilled than himself. He studied sales techniques, customer service, and profit margins. He analyzed the businesses he once admired.

And gradually envy became curiosity. Curiosity became learning. Learning became competence. Competence became confidence — not just motivational confidence. Evidence-based confidence. This is the confidence earned through consistently witnessing yourself overcoming challenges.

THEN CAME THE BIG JOB

Months later, Cliff was offered a contract far larger than anything he had handled before. His first thought was predictable. You can’t do this. Then the old word. MEDIOCRE. It still visited.

Beliefs built over years don’t evaporate because of one inspiring afternoon. But something else now existed alongside it. Evidence. Evidence of orders delivered. Evidence of customers returning. Evidence of rejection survived. Evidence of problems solved. Evidence of promises kept.

Cliff accepted a new job and completed it successfully. For the first time, he invested significantly in his personal growth. A coaching program that required him to travel abroad for a week. Previously, Cliff would have thought it was too costly. But now, he asked himself, “What might it cost me to stay the same?” He went. The program broadened his imagination. He saw businesses larger than his own. People operating at levels he had once viewed as unfamiliar. Ideas that once seemed exclusive to others now felt accessible and attainable.

E-commerce was no longer something mysterious that young men on the internet did. Sales was a skill. Leadership was a skill. Business systems could be learned. Negotiation could be learned. Even confidence, he discovered, could be partly built through practice. Possibility stopped looking like privilege. It began to look like something that could be approached.

YEARS LATER

Years went by, and Cliff’s story became clearer over time, as most stories do. People asked what had changed. He would sometimes say it was the day his friends died, at other times mention the nearly two weeks he spent alone, or describe it as a second chance. He claimed he never drank or smoked again after that period. Yet, the real transformation might have been more subtle.

Cliff had spent years unconsciously asking one question: “What does this prove about me?” A woman rejects me. It proves I am undesirable. My business fails. It proves I am mediocre. Someone else succeeds. It proves the system is unfair. A customer complains. It proves people don’t respect me. I feel uncomfortable. It proves I should escape. I am afraid. It proves I should stop.

His life had become a machine for converting events into evidence for beliefs he already held.

Then the question changed. A customer rejects me. What can I learn? Someone succeeds. What do they know? I feel afraid. What matters enough for me to act anyway? Business is difficult. What skill am I missing? I make a mistake. What must I change? Someone gives me an opportunity. How do I honor the risk they have taken on my behalf?

The events themselves were not necessarily more gentle; rather, their significance was different. This shift in meaning led to changes in behavior, which, over time, resulted in different outcomes.

BUT THERE IS AN UNCOMFORTABLE PART OF CLIFF’S STORY

We appreciate transformation stories because they help us categorize life clearly — before and after, bad Cliff and good Cliff, failure and success. However, human beings are more complex than that. Cliff’s transformation didn’t wipe away what had happened.

Three young men still died brutally. People were still robbed. The money he initially carried into his new beginning did not become morally clean, even though he later built a legitimate business. His father had wounded him, but his father did not make every subsequent choice for him.

His parents’ separation affected him, but it could not permanently absolve him. Society may indeed contain inequality, but inequality could not explain every self-destructive decision he made. Perhaps that is the most difficult part of growing up.

Two things can be true. You can have been wounded yet still be accountable for how you handle that wound. Similarly, being disadvantaged doesn’t mean you won’t sabotage opportunities, and experiencing rejection can be used as a reason to harm others later. Unfair treatment can lead to unfair behavior. Even if you work tirelessly, you might be doing so in pursuit of a belief that ultimately harms you.

Cliff had been involved in various activities for years — printing, clothes, barbershops, relationships, drinking, smoking, scheming, starting anew, stopping, and trying again. Despite constant movement, he made little progress, as his actions repeatedly led him back to the same result: mediocre.

That is what makes self-sabotage so difficult to recognize. Sometimes it doesn’t look like laziness. Sometimes it looks like tremendous activity.

THE QUESTION CLIFF’S STORY LEAVES US WITH

The key question isn’t just: What happened to you? Instead, it’s: What meaning did you assign to what happened? Because an event by itself is neutral; it’s the mind that interprets it.

Interpretation creates emotion. Emotion strengthens a belief. The belief creates a rule. The rule influences behavior. Behavior eventually produces results that can appear to prove the original belief.

Event → Meaning → Belief → Emotion → Behaviour → Result → Reinforced Belief

That loop can quietly turn into a life. Cliff’s father said one word: Mediocre. Cliff spent years collecting evidence to support that. But one day, a new possibility arose in his mind: Courage. Followed by Sacrifice, Responsibility, Learning, and Service. While his circumstances didn’t change immediately, his perspective did. And from that shift, new opportunities emerged.

Before moving on, perhaps sit with these questions:

- Which sentence from your past are you still trying to prove true?

- What does rejection say about you?

- What behaviors do you call “trying” that may actually be shielding you from fully exploring what happens if you commit?

- Where have you mistaken temporary relief for real peace?

- Whose approval are you still seeking through your work?

- Which group, ideology, or circle confirms the reality you already want to believe?

- Which challenges do you automatically see as reasons to give up?

And the most difficult question:

- If your current outcomes are partly shaped by the meanings you attach to your experiences, what new meaning might you need to reconsider?

Sometimes, the real prison isn’t the event itself but the meaning we assigned to it years ago — and never questioned again.

Talk. Clarify. Grow. Transform.

If this message stirred something in you, don’t let it fade.

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