When Everything Goes Wrong: Lessons from Ben Horowitz
Books & Insights series: "The Hard Thing About Hard Things" by Ben Horowitz
On my friend Ruslan Fazlyev's recommendation, I'm reading Ben's second book. This book isn't about growth strategies or motivation. It's about what happens when everything goes wrong according to plan.
Horowitz went through the dot-com crash, sold his company during a catastrophe, and knew what it was like to look employees in the eye whom he had to lay off because there was no money left in the company account.
What strikes me most is how different this book feels from everything else in the business section. Most books promise you the secrets to success. Horowitz promises you nothing except brutal honesty about what leadership actually looks like when the world is falling apart.
What I Wrote Down
I recorded the insights that strongly resonate with my daily agenda:
Perfect solutions don't exist. Often a leader chooses between bad and very bad.
The right people are more important than the right plan. In a crisis, a team ready to fight to the end means more than everything else.
Leadership is loneliness. You bear responsibility for everything and everyone, even when you're not sure of yourself.
These aren't motivational quotes. They're field notes from someone who survived what kills most companies. The loneliness part hits differently when you've felt it. When everyone expects you to have answers and you're making it up as you go along, hoping your best guess doesn't destroy everything people are counting on.
The Real Face of Difficulties
I really liked the examples of difficulties and struggle in the context of entrepreneurship. Horowitz doesn't romanticize any of it. He shows you exactly what it feels like:
- Difficulties are not failures, but they can lead to failure if you are weak. They require strength and endurance that many may lack.
This distinction matters more than it seems. Failure is binary - you either make it or you don't. But difficulties exist in that gray space where everything depends on how you respond. Your company isn't dead yet, but it's bleeding. What you do next determines everything.
- Difficulties are a state when you feel like an idiot, but nobody fires you. These are moments of extreme self-doubt that turn into self-hatred.
The worst part about being in charge is that your mistakes don't get you fired - they get other people fired. You have to live with every wrong decision, watch it play out, deal with the consequences, and somehow still look confident while doing it.
- Difficulties are the feeling of complete isolation, even when there are people around. You're surrounded by people, but remain completely alone.
Your team needs you to be strong. Your investors need you to be strategic. Your family needs you to be present. But the weight of all those decisions sits entirely on your shoulders, and there's nowhere to put it down.
- Difficulties are the moment when you want to stop everything, but you can't. This is real pain and disappointment.
Other people have the luxury of quitting when things get unbearable. When you're the one everyone is looking to, stopping isn't an option. The machine keeps running because it has to, not because you want it to.
- Difficulties are trying to go on vacation to feel better, but it only gets worse.
I had to smile at this one. The problems don't pause your mental health. They compound while you're away, and somehow you come back more stressed than when you left.
- Difficulties require action, even when all decisions seem wrong. This is the ability to find the best path when there are no good options.
This might be the most important skill Horowitz describes. In normal times, you're optimizing between good and better. In difficulties, you're choosing between different types of pain, and not choosing is usually the worst option of all.
Difficulties are the path through chaos, where you must keep moving even if you don't see the way out. This is a constant effort not to give up and not to stop.
Movement becomes more valuable than direction. Even if you're not sure you're going the right way, standing still guarantees you'll lose. At least if you're moving, you can course-correct.
- Difficulties teach that your task remains unchanged, regardless of the odds. This is faith not in statistics, but in your actions. Statistics often don't help with moving forward at all.
When everyone tells you that 90% of startups fail, that information is simultaneously true and useless. It describes the population but says nothing about your specific situation. Your job isn't to accept statistical inevitability - it's to execute so well that you end up in the surviving 10%.
The Paradox of Growth Through Pain
Difficulties give birth to greatness, but this knowledge itself provides no motivation.
This is probably the most honest thing in the entire book. Knowing that struggle builds character doesn't make the struggle hurt less. Understanding that crisis forges great leaders doesn't make leadership easier while you're in the middle of it.
The transformation happens retrospectively. While you're living it, it just feels like drowning. Only later do you realize you learned to swim.
A Conversation with the Next Generation
I read it aloud to my daughter because she wants to be an entrepreneur, but I saw absolutely no anxiety in her eyes, as if I had read self-evident truths.
This moment made me pause. Here I am, deeply moved by insights that came from Horowitz's real pain, and to her they sound like common sense. Is this wisdom or inexperience?
Maybe it's both. Her generation grows up with stories like this as baseline knowledge. They enter entrepreneurship knowing that difficulties are part of the game, not exceptions to it. This might make them more resilient - or it might mean they underestimate what they're signing up for.
But her calm response reminded me that these hard-won lessons become part of the collective wisdom. Each generation builds on the previous one's scars. She'll face her own difficulties, but she'll start with a map that people like Horowitz had to draw while bleeding.
Why This Book Matters Now
Most business advice assumes things are going well and you want them to go better. Horowitz writes for when things are going badly and you need them to just stop getting worse.
That's a different kind of leadership. It's not about inspiring people toward a vision of success - it's about holding everyone together when success seems impossible. It's not about making the right choice - it's about making any choice when all options lead to pain.
The book doesn't promise to make difficulties easier. It promises to help you recognize them for what they are: not personal failures, but professional realities that separate the leaders who survive from those who don't.
What separates them isn't superior strategy or better luck. It's the simple, stubborn refusal to quit when quitting would be the most reasonable thing to do.
The hard thing about hard things isn't that they're complex. It's that they're hard. And sometimes, that's all you need to know to keep going.
