Starting a company is easy. Honestly, anyone with a laptop and a decent Wi-Fi connection can register an LLC and call themselves a CEO. But staying in business? That's the part where the floor drops out. Ben Horowitz, the co-founder of Andreessen Horowitz, basically blew the lid off the "sunny Silicon Valley" myth when he wrote about the hard things about hard things. He wasn't talking about how to set a vision or how to hire your first ten employees. He was talking about the stomach-churning, late-night-panic-attack reality of being the person who has to decide which of those ten employees to fire when the bank account hits zero.
Execution is a grind. But the psychological toll is a monster.
Most business books are written by people who want to sell you a framework. They give you a "10-step plan to success" or a "blue ocean strategy." It’s all very neat. It’s all very clean. Real life is messy. Real life is when your biggest customer leaves, your lead engineer gets headhunted by Google, and your board of directors is looking at you like you’re the problem—all in the same Tuesday afternoon. That is the essence of the hard things about hard things. There is no recipe for a mess that big.
The Psychological Struggle of the "Wartime CEO"
Horowitz makes a sharp distinction between peacetime and wartime. Most of us are trained for peacetime. We’re taught to be collaborative, to listen to every opinion, and to build consensus. That works great when the market is growing by 20% every month and everyone’s stock options are worth a fortune. But what happens when the market crashes?
In wartime, the company is facing an existential threat. Competition is trying to kill you. You’re running out of cash.
A wartime CEO doesn’t have time for a consensus-building workshop. They have to make hard calls that make people hate them. It’s lonely. You’ve probably heard that "it’s lonely at the top," but you don’t actually feel it until you’re sitting in a parked car at 11:00 PM because you can't face your family yet, knowing you have to lay off 30% of your staff tomorrow.
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The struggle isn’t just about the external metrics. It’s the internal dialogue. You start questioning your own intelligence. You wonder if you’re a fraud. This is what Horowitz calls "The Struggle." It’s the period where you realize that there is no "easy" answer, only a choice between two bad options.
Why Technical Debt and Culture Debt Will Break You
People talk about technical debt all the time. It’s when you write messy code to get a product out fast, knowing you’ll have to fix it later. But hard things about hard things often stem from "management debt."
Management debt happens when you make a short-term hire just to fill a seat. Or when you give someone a title they haven’t earned because you’re afraid they’ll quit. It feels fine in the moment. You think, "I'll deal with the hierarchy issues later."
Except later always comes.
Suddenly, you have a Vice President who can’t manage a lemonade stand, but you can’t fire them without a massive legal headache or a blow to company morale. You’ve traded a future crisis for a present convenience. High-growth startups are basically debt-collecting machines. They collect on every corner you cut during the "move fast and break things" phase.
The Real Cost of Hiring "Big Company" Execs
One of the biggest traps founders fall into is hiring the "trophy" executive. They see someone who was a Senior VP at Microsoft or Amazon and think, "This person will bring the structure we need."
It usually fails.
Why? Because big-company executives are used to moving things. They have a system. They have a staff. They have a brand name behind them. In a startup, there is nothing to move. You have to create the thing from scratch. The skill set required to manage a thousand-person department is 180 degrees away from the skill set required to build a sales process from a blank Google Doc.
If you hire someone who needs a support staff to function, and you don't have a support staff, you just spent $300,000 a year on a paperweight.
The Brutal Art of the Layoff
Nobody wants to talk about this part. It’s the ultimate "hard thing."
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When you have to let people go because you messed up the strategy or the funding fell through, it’s a failure of leadership. Own it. There’s a specific way to handle this that preserves the dignity of the people leaving and the trust of those staying.
- Do it fast. Don't let rumors swirl for weeks.
- The CEO must be present. Don't hide behind HR.
- Be clear about why. If it’s a market shift or a funding failure, say so.
- Take care of the people. Provide as much severance and outplacement help as the bank account allows.
If you handle a layoff poorly, the people who stay will never trust you again. They’ll be looking for the exit the second their LinkedIn notifications ping. You’re not just managing the people leaving; you’re managing the survivors' psyche.
Facing the "Unbearable" Decision
Sometimes, the hard thing is knowing when to sell. Or when to pivot.
Look at Slack. It started as a gaming company called Tiny Speck. The game, Glitch, was failing. It was a "hard thing." Stewart Butterfield had to tell his investors and his team that the thing they spent years on wasn't going to work. But he noticed that the internal chat tool they built for the game was actually pretty good.
That pivot required a level of intellectual honesty that most people simply don't have. Most people would have gone down with the ship because they were too proud to admit the original idea was a bust.
Intellectual honesty is the only way out of "The Struggle." You have to look at the data—even the data that says you’re wrong—and act on it immediately.
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Actionable Insights for the Hard Days
If you are currently in the middle of a business crisis, or you’re feeling the weight of the hard things about hard things, here is how you actually move through it:
- Stop searching for the silver bullet. There is no one move that fixes everything. There is only "lead bullet" thinking—doing the hard, boring, painful work one inch at a time.
- Tell it like it is. Founders often think they need to put on a brave face for the employees. Wrong. If you lie to them and tell them everything is great when the office is half-empty, they’ll see through it. They aren't stupid. Be honest about the challenges. It actually builds more loyalty than fake optimism.
- Find a peer group. You cannot vent to your employees. You shouldn't always vent to your board. Find other founders who have been through the meat grinder. They are the only ones who won't give you platitudes.
- Manage your own mind. If you lose your head, the company is dead. Exercise, sleep (if you can), and realize that while the company might fail, you are not the company.
- Focus on the "Why." If there isn't a deep, fundamental reason why your company needs to exist, you will quit when things get hard. The "hard things" are only survivable if the mission feels mandatory.
Business isn't just about the numbers on a spreadsheet. It’s a test of character. It’s about what you do when there is no right answer and everyone is looking at you. You might fail. Many do. But the ones who make it are the ones who realize that the hard thing isn't an obstacle to the job—the hard thing is the job.