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The Hard Thing About Hard Things (2)

“The hard thing is not setting a big hairy audacious goal. The hard thing is laying off people when you miss the big goal. The hard thing is not hiring great people. The hard thing is when those great people develop a sense of entitlement and start demanding unreasonable things.”

Ben Horowitz opened his 2014 book The Hard Thing About Hard Things with this assessment. More than a decade later, these words are still as relevant as ever. The hard things haven’t gone away—they’ve multiplied.

Today’s growth leaders face Horowitz’s original challenges plus new ones: Should you automate this role or provide new training for your staff? How do you manage performance you can’t see? Do you deploy capital for AI while recession clouds gather? The fundamentals remain timeless, but context has grown more complex.

Why This Book Still Matters

Horowitz built Loudcloud during the dot-com crash transitioning the company from providing cloud services to creating software for managing those services. And he co-founded Andreessen Horowitz. His wisdom came from making painful decisions with incomplete information under pressure. While business has transformed since 2014, the psychological and strategic challenges he addresses are permanent features of scaling.

The book’s value lies in its examination of decisions with no good answers, only less bad ones. In an era of growth hacking content, Horowitz’s honesty about leadership’s brutal realities remains essential.

Four Timeless Hard Things (Made Harder in 2026)

1. Letting Go of Loyal People

Horowitz addresses one of leadership’s most agonizing decisions: demoting or firing someone who’s been loyal through difficult times. The emotional complexity hasn’t changed, but context has. In 2026, you’re assessing whether someone can adapt to AI-augmented workflows, thrive in hybrid environments, or navigate recession uncertainty—not just whether they’re talented.

The hard thing isn’t recognizing that someone perfect at $3 million of revenue isn’t right at $10 million. The hard thing is having that conversation when they sacrificed during lean years, when their institutional knowledge feels irreplaceable, and when you know that what made them valuable before now holds the company back.

2. Managing Your Own Psychology Under Pressure

“The Struggle,” as Horowitz calls it, is the lonely, grinding pressure of leadership when everything feels like it’s falling apart. This challenge has intensified dramatically. Today’s leaders manage AI adoption decisions that could make their business model obsolete if they’re wrong, dispersed teams they rarely see, and economic uncertainty while being told to “do more with less.”

The weight compounds. Every AI integration choice affects people’s livelihoods. Every staffing decision in uncertain times has no obvious right answer. You’re simultaneously the confident leader your team needs and the anxious executive questioning every choice. Horowitz’s core insight remains vital: you cannot successfully lead others through hard times if you cannot first manage your own fear, doubt, and isolation. No one else can do this work for you.

3. When Smart People Become Bad Employees

Horowitz addresses what happens when talented people develop entitlement or under-perform. In hybrid work, this has evolved. You’re managing people you can’t observe directly. High performers may produce less but claim greater productivity. Previously reliable employees may be disengaged but manage up skillfully during video calls.

The hard thing isn’t identifying under-performance—it’s making accurate assessments when traditional feedback mechanisms don’t exist. It’s distinguishing legitimate struggles from gaming a system with less visibility.

4. Deciding Whether to Sell

Horowitz explores the personal decision of whether to sell your company. This has new dimensions entering 2026. Valuations have compressed from 2021. Strategic acquirers are selective. Yet pressure to exit—from investors, partners, or exhaustion—remains intense.

The hard thing isn’t running spreadsheets. It’s knowing whether you’re selling because it’s right strategically or because you’re tired of The Struggle. It’s distinguishing prudent succession planning from giving up too soon while managing AI disruption, hybrid teams, and economic uncertainty.

The Hard Thing About Getting Better at Hard Things

Horowitz offers no magic formulas because none exist. What he provides is permission to acknowledge that leadership at scale is difficult, frameworks for thinking through impossible choices, and evidence you can survive decisions that feel unsurvivable.

For growth-stage companies navigating 2026’s complexities, this perspective is invaluable. The hard things remain navigable with clear thinking, honest assessment, and recognizing that feeling overwhelmed doesn’t mean failure—it means you’re leading.

Here’s My Take

The quality of your business equals the quality of your decisions under pressure. If you’re wrestling with the hard things—whether that’s organizational structure, performance management, or strategic direction—start with clarity about where you are and where you’re headed.

Take the Rockefeller Habits Checklist to assess your execution fundamentals. Strong systems don’t eliminate hard decisions, but they reduce the number of crises requiring them.

And join Carter Reports for practical insights on navigating the hard things every growth-stage leader faces—from AI integration to performance management to strategic clarity under uncertainty.

The hard things are permanent. Your ability to handle them isn’t.