You’re Not an Entrepreneur Until It Hurts

How delaying discomfort delays your business

In this series, we’ve covered everything from my decision to leave Microsoft, to selling my time as a first step, to productising my skills, and to changing my entire mindset around income. Each of these parts were essential in helping me navigate the shift from employee to entrepreneur. But there’s one final point that needs its own post, because I believe it’s the single most misunderstood aspect of this entire journey: pressure.

More specifically, the pressure to make money.

For many corporate professionals, it’s the very thing they are most afraid of. But having now been on the other side of that fear for years, I can say this with confidence: the pressure to generate revenue is not just unavoidable. It is the one thing that will transform you.

Without it, entrepreneurship remains theoretical. It never becomes real.

The Comfort Most People Won’t Give Up

When I speak to people in corporate jobs who are thinking about stepping out on their own, the one recurring barrier that comes up is not usually capability, or strategy, or even belief. The thing they’re actually most reluctant to lose is the comfort of a consistent paycheck.

It’s the predictability. The known. The safety.

The idea that money will arrive on the 25th of every month is so baked into the employee mindset that it becomes difficult to imagine a life without it. And I understand that. I lived that. I budgeted around those dates. I built my life on them.

But if you want to build a business, you have to give up that rhythm. You have to stop asking, “How can I make this leap without ever feeling the heat?” Because the heat is the thing that forges the focus.

The Myth of the Cushion

Many people tell themselves a story: if I can just land a one-year contract, or secure a few months of guaranteed income, then I’ll leave my job.

And to be clear, if that’s the only way you can make the move, then do it. But don’t mistake it for entrepreneurship. What you’re actually doing is repackaging your employment. You’re swapping one boss for another, but the dependency remains. You haven’t confronted the real thing yet.

The real thing is what happens when there’s no fallback. When it’s just you, your product, and the demand to get money in the door. That pressure is intense, yes. But it forces an economy of thought and action that is only possible under that condition.

It forces you to let go of distractions. It forces you to get closer to your customer. It forces you to do what works.

A Story Worth Paying Attention To

A friend of mine built a company after leaving his previous job. He was given some capital by his former employer to help him get started. The idea was solid. The market opportunity was there. And the financial runway looked reasonable on paper.

But eventually, the business started to run out of money. They reached a point where they had less than two months of cash in the bank. They called it their “doomsday spreadsheet.”

That was the moment everything changed. The team stopped discussing long-term plans. They stopped refining strategy decks. They stopped waiting for the perfect customer.

They picked up the phone. They got in front of clients. They sold. The business turned around. Not because they found a new market or redesigned their offering, but because the pressure clarified everything. They did what needed to be done because there was no longer any room to do anything else.

And you have to ask, why did they not do this any earlier? When they had plenty cash in the bank? Well, there just wasn’t the pressure to do so. If a business has a cash runway of twelve months, they will start to make money by month twelve. If they only have six months, funny enough they will make money by month six. That’s just the way it goes.

The Pressure Is the Point

People think the pressure is what makes entrepreneurship hard. I would argue it’s what makes it workable.

When you are under pressure to earn, your entire business goes through a natural filtering process. All of the abstract, theoretical, overly-complicated parts of your plan fall away. What remains is what customers are actually willing to pay for.

That pressure forces you to discard anything that does not contribute to viability. You stop entertaining vanity strategies. You stop hiding behind theory. You stop doing things that feel clever but don’t make money.

Instead, you build around product-market fit. You start listening more. You start solving real problems. And you start making decisions that are grounded in reality.

Productisation Under Pressure

The products we offer at Blacfox today were not dreamed up in a vacuum. They were shaped by necessity. They were informed by feedback. They were refined by pressure.

We had to respond to what customers wanted. We had to get better at pricing, packaging, delivery, support, and outcomes. And that only happened because the demand for income was real and immediate.

Payroll is not paid by ideas. It’s paid by invoices that get settled because you delivered something someone actually wanted. And when that pressure is real, not hypothetical, but sitting on your bank statement, you learn fast.

You learn what customers care about. You learn what’s worth your time. And you learn to cut anything that isn’t contributing to the business staying alive.

The Real Sequence of Building

Many people get confused about the right steps to follow when building a business. They want a clean roadmap. But in truth, the steps are fluid. They evolve.

What doesn’t change is the role pressure plays at each stage.

You begin by facing the demand for income. That sets your initial direction. You throw a lot of ideas at the wall. Some of it sticks. Most of it doesn’t.

Then you discard what doesn’t work. You refine what does. You learn to see the patterns. You begin to detect what’s repeatable, and you tighten your focus around those elements.

Each year, you remove 20 to 30 percent of what no longer works. And what remains, over time, becomes your business. Eventually, you’re left with something that is stable, sellable, and scalable. And that thing only exists because you were forced to face the pain of figuring it out.

You Cannot Outsource the Pressure

I need to say this clearly. You cannot delegate this part. You cannot buy your way out of it. You cannot avoid it with good planning or excess funding.

You have to live it.

You have to wake up with the pressure to perform. You have to feel the discomfort of not knowing how the next month is going to work. You have to direct that pressure into smart actions. You have to focus through it.

That is where you stop thinking like someone who left a job and start thinking like someone who runs a company. And the earlier you embrace this, the sooner your business begins to take shape.

Closing Thoughts

Entrepreneurship is not a comfort game. It is a focus game.

If you pad yourself too much, you delay the moment where the learning actually starts. And if you delay it too long, you never build the instinct required to navigate forward.

The goal is not to suffer needlessly. The goal is to use the discomfort constructively.

If you're entering this phase now, don’t waste time fighting it. Use it. Let it shape what you build. Let it clean out the distractions. Let it make you sharper. And when you finally arrive at a product you can scale, you’ll know it wasn’t accidental. It was forged.

Thank you for reading this series.

If any part of this has helped you in your own journey, I’m glad. And if you're in the middle of it, I’ll leave you with this: The pressure is not in your way. It’s showing you the way.

Make it rAIn, KG