When I met Jimmy, he was going through a very hard time. He was doing design work. A poster here. A small job there. A thousand shillings if he was fortunate. But even those small jobs seemed to take an exhausting amount of effort.
He had to self-promote continually by calling and messaging people, explaining his capabilities, and persuading them of his skills. Often, he would almost beg for a chance to showcase his expertise. Yet, despite all this hard work, a client might only give him a single job before vanishing.
Jimmy didn’t just see it as a client disappearing; he interpreted it as something significant. This distinction is crucial because in the Clarity Room we’ve repeatedly discussed that what happens to us and what we make of it are not the same thing.
An experience occurs, and we assign meaning to it. This meaning begins forming beliefs. Beliefs influence what we notice. What we notice influences how we feel. Our emotions influence our decisions. And eventually our decisions become behaviors, habits, and even aspects of our identity.
Jimmy was unknowingly caught in that cycle. When a client disappeared, he thought, “Maybe I’m not good enough.” A week with no work made him believe: Perhaps nobody needs what I offer. Watching someone online make millions led him to think, “Something must be wrong with me.” In time, he concluded, “I am failing.”
That was the point where the real trouble began, as Jimmy was no longer just trying to solve a business problem but also trying to avoid a judgment about himself.
Sunday Jimmy and Monday Jimmy
Jimmy was raised in a Christian household. Sundays were for church, where he arrived early and spent much of the day with a community he truly valued. There was fellowship, faith, hope, and a sense of belonging.
For a few hours, the world seemed understandable. Then Monday arrived, bringing rent, an empty phone, and unresponsive clients. Monday prompted the question: What am I really doing with my life? Jimmy struggled with this contradiction. How could he feel hopeful in some contexts and defeated in others? How could he believe his life had purpose and still feel utterly lost when he looked at his bank account?
He tried harder, which is the typical advice we give: work more, market more, make calls, and put yourself out there. Jimmy had heard it all before. But advice has a flaw: it assumes the person can act on it. Jimmy was told to make sales calls, even though some mornings getting out of bed felt like a challenge. He was told to believe in himself, even though, in his view, the evidence suggested he shouldn’t. He was advised to network, but every unanswered message felt like rejection.
And slowly, his world became smaller.
The Comparison Machine
Another thing was happening: Jimmy was observing people online. The internet can be a powerful tool that distorts perspective if you don’t understand what you’re seeing. Someone somewhere claimed to have made a million dollars in just four months. Jimmy saw that. Then he looked at himself. Rent was hard to pay. Jobs were unpredictable. His phone stayed silent.
His mind performed some rather brutal mathematics. They made a million dollars, while I can hardly pay rent, so I must be a failure. Though it sounds absurd when stated, many of us make similar judgments daily. We compare others’ successes to our starting point, their public accomplishments to our private doubts, their highlights to our confusion, and their tenth year to our first. We then often mistake this conclusion for objectivity.
Jimmy wasn’t merely comparing income; he was measuring personal worth. This is a risky comparison because when money reflects a person’s value, every financial setback feels like a crisis of identity. A tough month shifts from “Business is hard right now” to “I am not good enough.” A rejected proposal turns into “People don’t value me,” and another’s success might seem like running out of time. Possibilities may appear limited, and temporary setbacks seem permanent.
Pressure begins to affect the mind in an intriguing way. It narrows choices, making you see only two doors: succeed right away or be considered a failure.
Jimmy began shutting down. He stayed in his room. He withdrew. He ruminated. And the less he went out, the less evidence he encountered that contradicted what his mind was telling him. This is where self-sabotage becomes particularly cruel. Because it does not always look like laziness. Sometimes self-sabotage looks like thinking. Planning. Watching another motivational video. Changing your strategy again. Researching. Waiting until you feel confident. Perfecting something nobody has seen. Telling yourself you are preparing.
Jimmy seemed inactive on the outside, but inside he was busy. His mind was running through scenarios — judging, comparing, replaying, forecasting — and criticizing himself. He was exhausted from futile work.
We Did Not Start With Money
When Jimmy came to me, I did not start by asking him to build a business plan. I told him something much simpler. Get out of the house. Come. Sit with other young men. That was it. I was not pretending there was a silver bullet hidden in a men’s meeting. There wasn’t.
But I knew something else. You cannot heal the wallet while completely ignoring the mind that operates it.
Jimmy needed something his room could not give him. New evidence. His mind already had plenty of evidence of failure. The unpaid bills. The clients who disappeared. The unanswered messages. The people online who seemed to be doing spectacularly better. Locked inside his room, his mind could recycle those facts indefinitely, until they became a complete story about who Jimmy was.
He needed competing evidence. So every two weeks he came and sat with other men. Different people spoke. Family, social life, money, legacy, self-development, and spirituality. These men included those who had experienced success and failure, built things, or were still exploring and figuring things out.
Occasionally, Jimmy would hear something that interrupted the story running in his head. Not enough to transform him, just enough to make him wonder: What if the story isn’t entirely true? That question matters. Transformation rarely arrives with drums and fireworks. Most transformation begins with a small crack in certainty.
I Was Not Ready to Attack His Problem
I could have sat Jimmy down and told him everything I thought was wrong. That would probably have been useless. We human beings are remarkably adept at defending beliefs that hurt us.
Instead, I opted for a slower method, as change rarely happens all at once. It occurs through small, seemingly insignificant, difficult things repeated long enough to create new evidence of who we are becoming.
Jimmy excelled at design, especially posters. I told him I needed his skills but wouldn’t pay for that specific work. Instead, we arranged an exchange: he would help with the posters and venue setup, and also be present — around people, conversations, work, responsibility, and me. That presence was more important than the posters.
While we arranged chairs, set up the venues, adjusted designs, and repositioned items, I gained a deeper understanding of Jimmy’s mindset. I listened to his beliefs, watched his fears, and observed how criticism often quickly shifted into shame. I also saw how pressure could lead to avoidance and how eager he was to impress others. Beneath his drive to impress, there was usually a quieter plea: Please don’t discover that I am not enough. This belief can lead to self-sabotage, as everything feels like a test of worth, making even simple tasks overwhelming.
You don’t just submit a poster; you submit yourself. When you get feedback, it’s not merely about your design but a judgment of Jimmy. Instead of making a mistake, you become one. That’s why sometimes Jimmy disappeared.
The Disappearing Act
This became a common pattern for him. Whenever faced with something important, the old Jimmy would occasionally resurface. Under mounting pressure, his mind would race with doubts: What if I disappoint them? What if I can’t deliver? What if it’s not good enough? What if Edwin realizes I am less capable than he believes?
Sometimes, he would disappear without warning — ignoring messages, delaying assignments, or failing to follow through on commitments. To outsiders, this might seem irresponsible, and occasionally it was. We should avoid using psychological explanations to justify behavior that requires correction. However, I was more curious about what lay beneath these actions.
I began to realize that Jimmy wasn’t shirking his tasks; rather, he was avoiding the emotional pain of potential failure. Recognizing this difference altered my approach with him. I was able to address the behavior directly without criticizing him as a person. For example, I could say, “You let me down here,” instead of, “You are a disappointment.” These two statements serve different purposes: one fosters accountability, while the other impacts his self-identity.
Jimmy needed accountability badly. But he also needed to learn that correction was not rejection, that feedback did not mean abandonment, that making a mistake did not require disappearing, and that you can be uncomfortable and remain present.
Hurt Is Not Always Rejection
This has become another valuable lesson for us: people will hurt you, sometimes intentionally, sometimes unknowingly, often without realizing it. These hurts can be small or large — careless words, missed invitations, criticism, silence, being ignored, or someone choosing someone else.
But another person cannot carry the entire responsibility for what happens inside you after every hurt. At some point, emotional regulation becomes your work. Jimmy had to learn something difficult: Not everything painful is rejection. And rejection, when it does happen, need not become a statement about your worth.
You can experience pain without breaking down. You can go unnoticed without vanishing. You can accept correction without needing to defend yourself. You can feel uncomfortable without seeking validation. You can stay present, breathe, and stay whole. This is not a sign of weakness. Sometimes, restraint demonstrates that true strength is emerging. And this is not a one-time lesson; it requires daily practice.
So I Showed Him My Own Mess
Modeling is one of the most powerful ways human beings learn. If you lead people and want them to develop a specific behavior, they need to see you demonstrate it firsthand. I shared my genuine experience with Jimmy, not a polished image, but the real story.
For years, I have deliberately put myself in situations that make me uncomfortable because I want to grow. Some things I do well. Some I flounder spectacularly. Some I attempt, fail, regroup, and try again. I showed Jimmy that.
The writing I committed to daily. The ten-minute exercises. The affirmations. The projects. The uncomfortable conversations. The events. The men’s meetings we organised every two weeks.
Those meetings would sometimes drain me completely. He could see it. Yet two weeks later, I would do it again. Not because it had suddenly become easy, but because difficulty was not the deciding factor. Meaning was. I had attached a different meaning to discomfort.
Jimmy often saw discomfort as a sign that something was going wrong. I wanted him to try a different perspective: perhaps something is developing.
The Brain Is Never Lied To
I kept telling Jimmy, “The brain is never lied to.” You can stand in front of a mirror every morning and shout, “I am confident!” I am powerful! I am unstoppable! Your brain may quietly respond: On what evidence?
Encouragement has its place, but superficial confidence can be fragile. Genuine, grounded confidence is different and more durable. This was a key lesson in Jimmy’s journey: avoid building empty confidence and focus on developing evidence that truly deserves belief.
Confidence is a judgment we make about our ability. Competence is the demonstration of ability through performance. The two need to align.
Rather than urging Jimmy to feel more confident, I focused on helping him become more capable. Create another poster. Engage with people. Organize another event. Teach a new skill. Follow through on commitments. Be present as promised. Challenge yourself with tasks slightly beyond your current skill level.
Seek feedback regularly, correct your work, and repeat the process. Focus on small, challenging tasks that are difficult yet manageable, ideally completed daily. These tasks should push you just enough to stretch your limits without overwhelming you. Over time, this approach leads to noticeable progress. For example, Jimmy’s brain began to process new and different information as a result.
“Edwin, I Have Done More in the Last Few Weeks…”
One day, Jimmy called me out of breath: “Edwin, I’ve managed to accomplish more in recent weeks than in months.” This moment was meaningful, but not because I convinced Jimmy of his potential — I hadn’t. Instead, Jimmy began convincing himself, step by step. He organized events, designed projects, spoke publicly, made connections, solved problems, endured difficult times, made mistakes, and understood that life goes on despite setbacks.
Every action served as a minor vote against the old belief. Perhaps I am useless. No, I helped organize the event. Maybe I struggle to work with others. No, I brought people together. Maybe I have nothing valuable to give. No, someone is using something I created.
This is why small behavioral experiments are so effective. They shift beliefs from the imagined courtroom to the real-world laboratory of life. Instead of repeatedly asking: Am I capable? Take action that produces evidence. Then ask, “What does the evidence indicate?”
Give More Than You Receive
Jimmy also became more sociable. This was interesting because both he and I have a streak of enjoying being alone. But I wanted him to understand that you do not need to become an extrovert to be an exceptional connector.
Connection is a behavior that can be developed through practice. We organized an event, then another, leading Jimmy to meet more people. Helping more people. Eventually, he embraced the idea of giving more than he gets, starting to train others for free and organizing sessions aimed at uplifting others. I observed a noticeable shift begin to occur.
Jimmy used to approach the marketplace with the question, “Who will pay me?” Now he started asking, “What problems can I help solve?” This marks a significant shift in his mindset.
I strongly believe in spending part of your early development serving, experimenting, and creating value where appropriate. Not because your work is worthless, and certainly not because people should exploit you indefinitely. But because a deliberate season of experimentation can teach you things money alone cannot.
Who actually needs this? What problem hurts enough that people want it solved? What am I unusually good at? Where am I still weak? What do people repeatedly ask me to help them with? What can I deliver efficiently? What would somebody eventually pay for?
Help enough people with genuine curiosity, and you often discover the business hidden within the problem.
Then Jimmy Started Teaching
Eventually, Jimmy started teaching editing. I found this brilliant because teaching acts as an honest mirror. You might believe you understand something, but then someone asks, “Why?” That’s when you realize you might not know at all.
If Jimmy wanted to teach, he needed to refine himself. His understanding had to be clearer, his methods consistent, and his skills easier to explain. Teaching developed competence, but an essential next step was gaining exposure to mastery.
Jimmy had the chance to learn from someone much more experienced. The core message was clear: improve yourself. Practice diligently. Embrace discomfort. Focus on self-growth even without external praise. Build your skills before expecting others to notice. This last part was challenging for Jimmy.
“Why Aren’t People Paying Me?”
There were times when his ego was hurt. He was working, helping, designing, teaching, and showing up. Yet, amidst all this, a voice inside would wonder: Why aren’t people paying me for all this? I understood the frustration, but sometimes the market proves to be quite blunt.
The market does not owe us applause for trying hard. It asks other questions. Are you useful? Are you distinctive? Are you dependable? Can you consistently solve the problem? Do people trust you? Would someone recommend you when you are not in the room?
Jimmy still had work to do.
I explained to him that there is a phase where the aim isn’t just to extract money from every activity. Instead, the focus is on developing mastery, gathering evidence, and building a reputation so that earning makes sense over time. The goal is to become known for something, excel in it, and be reliable. After all, skill alone without dependability is hard to sell.
Talent that disappears under pressure creates risk. This was one of Jimmy’s hardest developmental edges. He had to stop seeing reliability as a personality trait you either have or don’t. Reliability is behavior. It is built every time you do what you said you would do, especially when you don’t feel like it.
Self-Worth Is Not Self-Esteem
During this journey, a further distinction emerged: self-worth and self-esteem are connected yet not the same. Self-esteem tends to inquire: How am I performing? In contrast, self-worth considers the question: Do I still matter when I am not performing well?
Jimmy had fused the two.
If work was good, Jimmy was good. If the money came, Jimmy was valuable. If people praised him, Jimmy was talented. If clients disappeared. Jimmy disappeared emotionally with them. That is an exhausting way to live. Because performance fluctuates. Money fluctuates. Recognition fluctuates. People fluctuate. If your worth rises and falls with them, your entire internal world becomes hostage to circumstances.
Jimmy needed an internal foundation strong enough to say: I matter before the applause. And enough humility to say: I still need to improve my competence. That combination is powerful. Worth without competence can become entitlement. Competence without worth can become a desperate lifelong audition for approval. You need both.
Almost Two Years Later
It has not even been two years since I started talking to Jimmy. Sometimes I look at him now and am astonished by how far he has come. He is more confident, more sociable. He speaks, not merely in the timid way of someone trying not to make a mistake.
He has become a confident speaker in his own right. He teaches. He connects. He organizes. He contributes. He still has doubts. Of course he does. He occasionally falters. Of course he does.
Growth does not make you superhuman. Old beliefs occasionally knock on the door. The difference is that Jimmy now has more evidence to draw on when they do. That matters, because the goal was never to create a Jimmy who never doubts himself. The goal was to develop a Jimmy who no longer automatically obeys doubt.
The Smallest Next Step
When people face pressure, they often ask themselves enormous questions: What should I do with my life? How can I achieve success? Will I earn enough money? What if nothing works? These questions can stop us because they seek certainty about an unseen future. Sometimes, a better approach is to focus on smaller questions: What’s the next decision?
For Jimmy, it wasn’t about becoming financially successful but about simple steps: Can I leave the house today? Can I go to the meeting? Can I design this poster? Can I arrive on time? Can I organize an event? Can I teach what I know? Can I improve what I taught? Can I take on something more difficult? This is how life unfolds — through small decisions amid uncertainty, not leaps into certainty.
Becoming Jimmy
I think our journey towards self-worth and self-esteem is partly a journey of character. Resilience. Patience. Kindness. Courage. Dependability. Self-trust. The ability to face adversity without letting every difficult experience become a verdict on who we are.
Character cannot be downloaded. It has to be practiced. You place yourself on a path that asks something of you. You encounter difficulty. You discover a weakness. You work on it. You fail. You learn. You return. You stretch a little further. And slowly, your self-concept begins to rise to meet the evidence you are gathering. Your imagination changes too. You begin to see possibilities your earlier identity could not. Things you once considered impossible become merely difficult. Things you once thought belonged to “other people” begin to enter the boundaries of what you might attempt.
Then you move forward, one step at a time, into the unknown. With each step, you may not yet see everything that awaits. But maybe now there is a small, steady light within you — not a wild blaze of empty motivation, noise, or hype. Instead, it is a quieter, grounded glow, firm and evidence-based.
A light glow that says:
I have been in unfamiliar places. I have done difficult things. I have failed and remained intact. I can learn. I can practice. I can become.
And with every step into the uncertainty, that candle illuminates a little more of a world you have never visited. Things you have never done. Capabilities you did not know you had. Possibilities a younger version of you would have struggled to imagine.
That is the journey Jimmy has finally stepped into. Perhaps that is what confidence was meant to be all along. Not certainty that everything will work, but enough evidence of who you are becoming for uncertainty no longer to have the power to make you disappear.
Talk. Clarify. Grow. Transform.
If this message stirred something in you, don’t let it fade.
1. Join my LinkedIn Habit Coaching Newsletter: https://www.linkedin.com/newsletters/habits-with-coach-edwin-7399067976420966400/
2. Join my Habit WhatsApp Community at https://whatsapp.com/channel/0029VbAmKkOBvvsWOuBx5g3L
3. Join The Clarity Room at https://chat.whatsapp.com/HzoEAcKBM4lDHtzDnl6IL8
4. Ready to level up your life? Join my 12-Month Personal Transformation Program and let’s intentionally build the next version of you — with clarity, discipline, and momentum. Call or WhatsApp me directly at +254 724 328059, and let’s begin.
Comments
Post a Comment