Fighting the Good Fight Isn’t Always Easy: The Days When Being Captain Feels Like a Burden

Even those who choose the entrepreneurial path are allowed to question it sometimes.


There are days in business when you see the iceberg coming long before impact. You know it’s there, you know it could sink everything you’ve built, but you’re not sure if you can steer away in time.

Today is one of those days for me.

There’s a financial obligation looming that I’m not sure I can meet. The kind that keeps you awake at 3 AM running calculations that don’t add up no matter how you arrange the numbers. The kind that makes you wonder if this time, you’ve finally reached the limit of what willpower and creativity can solve.

And you know what I’m doing about it? I’m writing this article, checking emails, and pretending the ship isn’t heading toward the rocks.

Do you blame me?

The Weight of Always Being Strong

People expect entrepreneurs to be perpetually optimistic, constantly motivated, always ready with another solution. We’re supposed to be the captains who never doubt the journey, never question the destination, never wish we could just be passengers for a while.

But here’s what I need to say today: sometimes I get tired of being the captain.

Sometimes I want to be the client who gets waited on instead of the business owner who does the waiting. Sometimes I want someone else to worry about cash flow while I focus on the work I actually love. Sometimes I want to clock out at 5 PM and let someone else handle the 3 AM anxiety about whether we’ll make payroll.

Is that too much to ask? Am I being unreasonable?

The Complexity of Loving What Challenges You

I know this is the life I chose. I know I wouldn’t trade it for anything, even on days like today. But just because something makes you happy doesn’t mean you’re not allowed to get frustrated when it’s not working the way you planned.

I love my family more than anything, but they drive me crazy sometimes. I love building Yati Group, but there are days when it feels like it’s trying to kill me. I love the freedom of entrepreneurship, but I hate the isolation of being the person everyone depends on for answers.

This isn’t contradiction—it’s complexity. You can be grateful for something and still be exhausted by it. You can believe in your path and still question whether you’re strong enough to walk it some days.

The Myth of Constant Encouragement

I spend a lot of time encouraging other entrepreneurs, sharing insights about building businesses and pushing through challenges. Today, I’m not feeling particularly encouraging. Today, I’m feeling human.

I make mistakes regularly. I get tired more often than I admit. I fail at things I should be good at by now. Some days, the gap between where I am and where I want to be feels insurmountable.

Are you surprised I’m not my usual encouraging self today? Did you think entrepreneurs are immune to doubt, frustration, and fear?

We’re not. We just don’t talk about it publicly very often because we think it makes us look weak or incompetent. But maybe that’s the problem.

The Pressure of the Entrepreneurial Image

There’s this myth that successful business owners have it all figured out, that we’ve moved beyond the struggles that plague “normal” people. That we’ve transcended worry about money, stress about the future, or frustration with setbacks.

The truth is messier. The truth is that building something meaningful is hard every single day, not just in the beginning. The problems get more complex, the stakes get higher, and the pressure to have all the answers increases with every success.

Sometimes the hardest part isn’t solving the business problems—it’s maintaining the facade that you’re always confident about your ability to solve them.

What Nobody Tells You About Fighting the Good Fight

When you choose entrepreneurship, people warn you about the financial risks, the long hours, the uncertainty. What they don’t tell you about is the emotional toll of being responsible for everything and everyone, all the time.

They don’t tell you about the guilt of disappointing clients when things go wrong. The weight of knowing that your decisions affect not just your livelihood, but your employees’ families. The isolation of being the person who can’t show weakness because everyone is counting on your strength.

They don’t tell you that some days, fighting the good fight feels less like heroism and more like stubborn refusal to admit defeat.

The Permission to Be Human

Today, I’m giving myself permission to be frustrated with the thing I love most. Permission to acknowledge that building a business is exhausting in ways that have nothing to do with work hours. Permission to admit that sometimes I don’t have the answers, and that scares me.

I’m giving myself permission to write about doubt instead of certainty, about struggle instead of success, about the days when entrepreneurship feels like a burden instead of a blessing.

And I’m giving you permission to feel the same way about whatever you’re building.

Why Honesty Matters More Than Inspiration

I could have written an inspiring piece about perseverance and positive thinking. I could have shared strategies for overcoming obstacles and maintaining motivation. Those articles have their place, and I’ll write them again.

But today, I think honesty serves better than inspiration.

Because when you’re facing your own iceberg, you don’t need someone telling you to think positive thoughts. You need to know that even people who’ve been doing this for years still face days when the problems feel bigger than the solutions.

You need to know that questioning your path doesn’t mean you’re on the wrong one. That feeling overwhelmed doesn’t make you weak. That wanting to be the passenger instead of the captain sometimes doesn’t mean you should give up the wheel.

The Strength in Admitting Struggle

There’s something powerful about acknowledging struggle without trying to immediately fix it or find the lesson in it. Sometimes things are just hard, and that hardness doesn’t need to be transformed into wisdom or motivation.

Sometimes it’s enough to say: this is difficult, I’m tired, and I don’t have all the answers right now.

That acknowledgment doesn’t make you a bad entrepreneur. It makes you a human one.

Tomorrow Will Be Different

I’ll wake up tomorrow and probably feel differently about these challenges. I’ll find new energy for problem-solving, remember why I chose this path, and get back to building something meaningful.

But today, I’m allowing myself to feel the weight of being captain. Today, I’m admitting that fighting the good fight isn’t always easy.

And somehow, that admission feels more honest than any inspirational message I could offer.

The Real Encouragement

So here’s my encouragement today: you’re allowed to have days when your calling feels like a burden. You’re allowed to question your choices without abandoning them. You’re allowed to be tired of being strong.

Those feelings don’t disqualify you from entrepreneurship. They qualify you as human.

The fight is still good, even when it doesn’t feel easy. Maybe especially then.

Be encouraged—not because everything is perfect, but because perfect was never the point. Building something meaningful was always going to be messy, difficult, and occasionally overwhelming.

That’s not a flaw in the system. That’s the system working exactly as designed.

And you’re exactly where you need to be, even when—especially when—it doesn’t feel that way.

The Ghost Town That Taught Me Customer Adoption: Why First Sales Don’t Mean Success

Most entrepreneurs celebrate too early—and lose customers they never actually had.


There’s a filling station five minutes from my house in Mbabane that taught me one of the most expensive lessons in business: the difference between a customer trying your product and a customer choosing your product.

When it first opened, this convenient new station was a ghost town for months. The only people you’d find there were petrol attendants standing in groups chatting as if that’s what they were hired to do, and shop attendants eager to greet you with wide smiles even when you were just buying gum. Cars were rare. The shop stayed empty.

I watched this painful slow start and assumed, like most people, that the business was failing. Fast forward six months later, and that same station is now the busiest in town. Drivers in the neighborhood have gradually discovered its convenience and made it their first choice for fuel and everyday essentials.

What I witnessed was a masterclass in customer adoption that most business owners completely misunderstand.

The Three-Stage Journey I’ve Observed

Through years of building businesses and watching this filling station transform, I’ve realized that customers move through three distinct stages before they truly become yours:

Stage 1: The Curious Trial

They try your product or service to see what you’re really about. How different are you? Do you deliver on your promises? This is exploration, not commitment. Most of my early clients at Yati Group were in this stage—testing our approach, comparing us to alternatives, seeing if we were worth their time.

Stage 2: The Validation Purchase

They buy again to confirm consistency. Was the first experience a fluke, or can you deliver reliably? This is the make-or-break moment that most entrepreneurs miss completely. I’ve learned that this second purchase is actually more important than the first—it’s where customers decide if you’re legitimate.

Stage 3: The Adoption Decision

They choose you permanently. By this stage, they’re not comparing anymore—they’re committed. When they need what you offer, you’re their automatic choice. You’ve achieved what marketers call “top of mind awareness,” but what I call customer ownership.

The Expensive Mistake Most Entrepreneurs Make

Here’s where most business owners go wrong, and I’ve made this mistake myself: they think they’ve won a customer after stage one. Someone buys once, and suddenly we’re celebrating, projecting growth, maybe even expanding based on these “customers” who were just taking us for a test drive.

I remember the early days at Yati Group when a client would engage us for a project, and I’d immediately start planning how to serve them long-term. I was counting customers I didn’t actually have yet. Some of those “clients” disappeared after that first project, and I couldn’t understand why until I learned about this three-stage process.

The truth is uncomfortable: that first sale doesn’t make them a customer. It makes them a prospect who’s willing to experiment with you.

The Critical Second Purchase Push

What I’ve learned through experience is that stage two—the validation purchase—requires the most intentional effort from the business owner. The customer has tried you once and now they’re deciding: was that experience repeatable?

This is where that gentle but strategic push becomes essential. Not aggressive selling, but making it irresistibly easy for them to experience your consistency. At Yati Group, I learned to treat every client’s second engagement as more important than their first. The first project gets them interested; the second project gets them committed.

Many businesses lose customers between stages one and two not because their product is bad, but because they don’t actively facilitate that crucial second experience. They assume the first good experience will automatically lead to more business. It won’t.

Building Your Customer Adoption System

Through watching that filling station’s transformation and applying these insights to my own business, I’ve developed what I call the Customer Adoption Acceleration System:

For Stage 1 (Trial): Make Trial Irresistible

Your goal isn’t to make money on the first interaction—it’s to prove value so clearly that stage two becomes inevitable. Price for trial, not for profit. Design the experience to exceed expectations dramatically.

For Stage 2 (Validation): Engineer the Return

This is where most businesses are passive when they should be strategic. Create specific reasons for customers to engage again quickly. Follow up systematically. Make the second purchase easier and even more valuable than the first.

For Stage 3 (Adoption): Become Automatic Choice

By this stage, your job is to stay top-of-mind and remain consistently excellent. This happens through what I call “investment marketing”—actions today that ensure when they need what you offer, they think of you first.

Why This Changes Everything

Understanding this three-stage process completely transforms how you measure success and allocate resources. Instead of celebrating first-time purchases, you start tracking progression rates. Instead of focusing on acquiring more prospects, you focus on moving existing prospects through the stages.

That filling station didn’t become successful because it suddenly got more convenient—it was always convenient. It became successful because enough people in the neighborhood moved through all three stages of adoption. The attendants’ friendliness wasn’t just nice service—it was stage-two facilitation, making it pleasant to return.

The Application for Your Business

Every business owner should ask themselves:

  • What percentage of my first-time customers make a second purchase?
  • How long does it take for customers to move from trial to validation to adoption?
  • What am I actively doing to facilitate the second purchase?
  • Do I measure customer acquisition or customer progression through the stages?

The filling station taught me that business growth isn’t just about getting people to try you—it’s about systematically moving them through a predictable adoption journey.

The Competitive Advantage

Here’s what I’ve realized: most businesses compete for stage-one customers. They fight over who can attract more people to try their product. But the real competitive advantage lies in stages two and three—in conversion rates and customer lifetime value.

The businesses that dominate their markets aren’t necessarily the ones that get the most first-time customers. They’re the ones that consistently move customers through all three stages of adoption.

That filling station is now the busiest in town not because it attracted more people to try it, but because it converted more triers into permanent customers. That’s the difference between a business that survives and one that thrives.

The question isn’t how many people have tried your business. The question is: how many have truly adopted it?

Why Some Calls Are Not Worth Receiving: The Job That Saved My Life by Rejecting Me

Sometimes the best thing that can happen to your future is having your backup plan fail.


I was rummaging through old files recently when I found an application letter I wrote on December 29th, 2008. It was for a marketing position at an NGO in Eswatini—a job I desperately wanted but never got.

A portion of the application letter.

Looking at that letter now, I realize it might be the most important rejection of my life.

The Desperation That Almost Derailed Everything

December 2008 was one of the darkest periods I’d ever experienced. I had just handed in my resignation from my first company, which I co-owned with two other directors. After irreconcilable differences tore us apart, I had to walk away from something I’d helped build.

I was frustrated, confused, and terrified about what came next. When I saw that NGO position advertised in the newspaper, it felt like a lifeline. I convinced myself it would provide the steady cash flow I needed while I figured out my next move. A safe harbor while I built something new on the side.

I crafted what I thought was a compelling application letter and waited for the call that would rescue me from uncertainty.

The call never came.

The Path I Almost Didn’t Take

Starting 2009 without any guarantees, I threw myself into the venture I’d been working on part-time—internet marketing. In Eswatini, this field barely existed. I was venturing into uncharted territory with no safety net, no steady income, and no guarantee of success.

I won’t lie: I was terrified. I had never done anything like this completely on my own, and I was essentially betting my future on something most people in our market didn’t even understand yet.

But nine years later, I can’t stop imagining how different my life would have been if that NGO had called me back. And I’m grateful they didn’t.

The Sliding Doors Moment

That rejection forced me onto a path that led to building Yati Group, discovering my capacity for strategic thinking, and ultimately creating something far more valuable than any salary could have provided. If I had gotten that job, I would have spent years building someone else’s dream while my own remained an unrealized side project.

The steady paycheck would have been seductive. The security would have been comfortable. And that comfort would have slowly killed the urgency that drove me to build something meaningful.

Instead of waking up each day knowing I controlled my destiny, I would have been trading time for money, passion for security, potential for predictability.

The Real Cost of Backup Plans

What I’ve learned since then is that backup plans often become primary plans by default. When you have a safety net, you don’t leap as far or fight as hard. When you have alternatives, you don’t commit as completely to the thing that could transform your life.

That job would have been my backup plan, but backup plans have a way of becoming the main plan when things get difficult. And building something meaningful is always difficult at the beginning.

If I had received that call, I probably would have taken the job “temporarily” while building my business on evenings and weekends. But evening energy and weekend hours are rarely enough to build something transformational. The job would have consumed my prime time and best thinking, leaving scraps for the dream that could have changed everything.

The Journey That Made It Worthwhile

Don’t misunderstand me—choosing the uncertain path wasn’t easy. Business has been brutal at times. I’ve experienced highs that felt like floating and lows that felt like falling straight into hell. This article right here will tell you the whole story about the lows

There were weeks when I went without a single payment, surviving on friends throwing me a few rands to tide me over. I have financial and emotional scars from those early years that remind me how close I came to failure multiple times.

But here’s what I discovered: there’s nothing like waking up knowing you own your time and control your destiny. When you’re building something that belongs to you, even the difficult days feel different. Even the failures teach you something valuable.

Money becomes important, but it stops being the primary motivation. Eventually, it becomes about the possibilities—what you could build, who you could impact, how far you could push the boundaries of what’s possible. Those possibilities keep you going even when the financial rewards aren’t immediate.

The Deception of “Safe” Choices

That NGO job felt like the safe choice in December 2008. Steady income, clear responsibilities, predictable career progression. But safety is often an illusion, especially in today’s rapidly changing economy.

How many “safe” jobs have disappeared due to technological disruption, organizational restructuring, or economic shifts? How many people who chose security over opportunity found themselves forced into uncertainty anyway, but without the skills and mindset that come from building something yourself?

The riskiest choice might actually be avoiding risk entirely. When you don’t develop the capability to create value independently, you become completely dependent on others to provide opportunities for you.

What Rejection Actually Teaches

That rejection taught me something invaluable: sometimes what feels like failure is actually redirection toward something better than you could have imagined.

If every door opened easily, we might walk through the wrong ones. If every opportunity materialized, we might settle for smaller dreams. If every backup plan worked out, we might never discover what we’re truly capable of achieving.

The rejection forced me to rely on my own capability rather than someone else’s validation. It pushed me to create opportunities rather than wait for them to be offered. It taught me that my future was my responsibility, not something to be handed to me by others.

The Calls Not Worth Receiving

Looking back, I realize there have been many calls throughout my journey that weren’t worth receiving:

The “opportunities” that would have distracted me from building Yati Group into something significant.

The partnerships that looked attractive but would have limited my growth potential.

The safe choices that would have provided comfort but prevented breakthrough.

The backup plans that would have become primary plans and kept me from discovering what I was really capable of building.

The Pattern of Productive Rejection

This experience taught me to look for patterns in the rejections and closed doors I experience. Often, what feels like rejection is actually protection from choices that would have limited my potential.

That job rejection protected me from spending my most creative and energetic years building someone else’s vision. Other rejections have protected me from partnerships that would have constrained my growth, opportunities that would have been distractions, and paths that would have led away from my real purpose.

The Question That Changes Everything

Now, when I face rejection or when anticipated opportunities don’t materialize, I ask myself a different question: “What if this rejection is protecting me from something that would prevent me from achieving something better?”

This doesn’t mean I don’t pursue opportunities or that I rationalize every failure as a blessing. But it does mean I’ve learned to trust that sometimes the path forward becomes clearer when certain paths are blocked.

For Those Waiting for Calls

If you’re waiting for a call that isn’t coming, for a door that isn’t opening, for an opportunity that isn’t materializing, consider this: maybe you’re not supposed to wait. Maybe you’re supposed to create your own opportunities.

That call you’re waiting for might represent someone else’s timeline, someone else’s vision, someone else’s definition of success. The opportunity you’re hoping for might actually be smaller than what you could build if you stopped waiting and started creating.

The Gratitude of Hindsight

Today, I’m grateful for every rejection that pushed me toward building something I truly own. I’m thankful for the doors that didn’t open because they forced me to create my own entrance. I appreciate the calls that never came because they prevented me from accepting less than what I was capable of achieving.

The job I desperately wanted in December 2008 would have given me a salary. The path I was forced to take instead gave me a life.

Sometimes the best thing that can happen to your future is having your backup plan fail. Because when there’s no safety net, you learn to fly.

Don’t stress about the call that isn’t coming through, the business deal that seems to be stalling, or the connection that promised to help but never follows through. You might just be better off without it.

The rejection that feels painful today might be the redirection that saves your tomorrow.

The Corporate Experiment: Why I Quit Being an Employee After 8 Months

Sometimes you need to lose yourself to remember who you are.


In November 2011, I did something I hadn’t done in six years: I took a job working for someone else.

My friends looked me in the eye and said flat out, “This isn’t you.” They were right, but I needed to find that out for myself.

After years of building my business, carrying the weight of everyone’s livelihood on my shoulders, making every decision, solving every crisis—I was exhausted. The idea of having someone else worry about where the next paycheck would come from felt like liberation. A steady salary, predictable hours, someone else’s problems to solve. For once, I could just be an employee.

So I spent a month weighing the decision, handed my business over to my inexperienced team, and walked into an open-plan office to become what I never thought I’d be again: someone else’s subordinate.

From King to Gatekeeper

On November 1st, 2011, I was directed to a cubicle right by the entrance where I literally became the department’s gatekeeper. Everyone who walked in had to pass by me, and I found myself lifting my head to acknowledge greetings like some sort of corporate receptionist.

I missed my office immediately—my space where I ruled, where I made decisions that mattered, where I controlled my environment. I tried negotiating for better space with the department administrator, but she recited some memo explaining why she couldn’t help me.

I was stuck as a gatekeeper.

It was surreal. I almost quit those first few days, but I forced myself to stay. I told myself I needed to learn what it meant to be an employee again, to understand what my own team experienced, to become a better leader by remembering what it felt like to be led.

What I discovered shocked me.

The Myth of My Own Work Ethic

Before taking that job, I had a very specific image of myself. I thought I was a natural early bird who sprang out of bed ready to conquer the world. I believed I was a working machine who could go twelve hours straight without breaks, Berrocca, or coffee. I actually hated public holidays because they meant wasted opportunities to get more work done.

I thought money didn’t drive me—that I could do more for less as long as I enjoyed what I did. I believed I was incredibly patient, capable of working with even the laziest team members without losing my cool.

Then I became an employee again, and I realized I was just like everyone else.

I dreaded going to work. I pulled myself out of bed and chased deadlines by their tails. By 12:30 PM, I was exhausted and couldn’t stop checking my watch, waiting for lunch break. I took short naps during lunch and came home drained.

I was a monster in the morning until I had my Berrocca and coffee. I highlighted holidays on my calendar and lived for weekends. I couldn’t wait for payday and got excited about memos announcing half days.

I was caught in the corporate grind, and it was grinding me down.

The Mirror I Didn’t Want to See

Taking that hard look at myself was devastating. I had stepped so far out of my own skin that I barely recognized the person staring back at me. The driven entrepreneur who controlled his destiny had become just another worker counting down the hours until freedom.

I started reminiscing about the “good old days” when I owned my time, controlled my schedule, and made decisions that actually mattered. I wanted to get back there as fast as possible, but I also needed to understand what had happened to me.

The Uncomfortable Truth About Ownership

What I learned during those eight months changed my understanding of work, motivation, and human nature forever.

When you’re building something that belongs to you, every hour invested compounds. When you’re working for someone else, every hour is just traded for money. The psychological difference is profound.

When I was running my business, those twelve-hour days felt energizing because I was building something. When I was working for someone else, eight hours felt draining because I was just completing tasks that served someone else’s vision.

It wasn’t about the work itself—it was about ownership.

The Great Deception of “Work-Life Balance”

Corporate life promised work-life balance, but what it actually delivered was work-life separation. Instead of integrating meaningful work into a life I designed, I was compartmentalizing someone else’s priorities into predetermined time slots.

The irony was devastating: in trying to escape the stress of entrepreneurship, I had traded ownership of my time for the illusion of security. But that security came at the cost of everything that made work feel like building rather than just doing.

The Day I Quit

After eight months, I packed my lessons and corporate experience into a small box, tucked them alongside my battered pride, and quit.

I remember walking back to my office for the first time as a business owner again. It was around 10 AM on a Tuesday, and the streets were empty. For a moment, I felt guilty—had I told my boss I would be late? Then I laughed at my own absurdity as I took a right turn at the traffic lights and headed back to my kingdom.

That feeling of driving to my own office, on my own schedule, to work on my own vision—it was intoxicating.

What the Experiment Taught Me

Those eight months weren’t wasted time. They were a masterclass in understanding the difference between being an entrepreneur and being an employee—not just intellectually, but viscerally.

Entrepreneurs aren’t superhuman. We’re not naturally more disciplined or motivated than employees. We’re just people who’ve chosen to tie our energy to ownership rather than security.

Context shapes behavior more than character. Put an entrepreneur in an employee context, and they’ll behave like an employee. Put an employee in an entrepreneurial context with real ownership, and they might surprise you.

The grind is the same; the meaning is different. Building a business is just as exhausting as working for someone else, but it’s the difference between exhaustion that builds something and exhaustion that just gets you through the day.

Time ownership is everything. The ability to control your schedule isn’t just a perk of entrepreneurship—it’s the foundation of everything else. When someone else owns your time, they own your potential.

The Lesson for My Team

When I returned to my business, I looked at my team differently. I understood why they watched the clock, why they needed clear direction, why they didn’t think like owners. They weren’t owners.

But I also realized that some of them could be, if I created the right conditions. If I gave them real ownership over outcomes rather than just tasks. If I let them control more of their own time and methods. If I shared the upside, not just the workload.

Some of my best builders today are people who made that transition from employee thinking to owner thinking because I remembered what it felt like to lose that ownership myself.

The Choice We All Face

Everyone faces this choice at some point: security or ownership. A steady paycheck or the uncertainty of building something. Predictable days or the chaos of creating value.

Neither choice is wrong, but they’re fundamentally different. And you can’t really understand the difference until you’ve experienced both.

My eight-month corporate experiment taught me that I’m unemployable—not because I can’t do the work, but because I can’t live with someone else owning my time and limiting my potential.

Some people discover they prefer the security and structure of employment. Others realize, like I did, that they’re willing to trade security for ownership.

The Real Return on Investment

People often ask if those eight months were a waste of time. They weren’t. They were an investment in understanding myself and my team better. They taught me why entrepreneurship is hard but why employment felt harder for me.

Most importantly, they reminded me that time is the one thing that, once lost, can never be recovered. Those eight months taught me to value my entrepreneurial freedom not as a burden I carry, but as a privilege I’ve earned.

Given the choice again, I choose the business grindstone every day. Not because it’s easier, but because it’s mine.

And that makes all the difference.