Gen Z Isn’t Cooked: Finding Purpose in an Age of Despair

If you dive into books or articles on building great organizations, you’ll find no shortage of frameworks, models, or operating systems. I’ve studied and used pieces of nearly all of them for about a decade now. But none quite fit the kind of organizations I’ve worked in: organizations created to solve big problems and create lasting impact.

After a decade of leading organizations, I’ve come to learn that every healthy and effective organization is built upon four foundations – Impact, Talent, Operations, and Ownership. And when these foundations are built well, they allow every corner of the organization to fire on all cylinders.

Greetings from day one of my week of PTO. Seemed like a fitting time to talk about one of my favorite benefits: unlimited time off.

A lot of people say unlimited PTO is a scam. And in many companies, it is. But that’s not a failure of the policy; it’s a failure of leadership.

I stand behind unlimited PTO 100%. We use it at my organization, and we make an effort to ensure it gets used. And that’s the key: leaders have to take responsibility for making it work.

You have to build a culture that respects time off. Make it clear people aren’t to be bothered when they’re out. Do a regular inventory of who hasn’t taken time and ask why. Then fix those barriers.

Most of the time, what stops someone from taking PTO isn’t laziness or neglect; it’s guilt. They don’t want to burden their team. Or maybe they’re in the middle of a big project. Or they treat PTO like a golf score, where the lower the number, the more impressive it looks.

Those are all management issues. If someone feels like they can’t step away, that’s often on leadership. Do you have a contingency plan so people can unplug? Are your timelines so inflexible that a few days off will derail everything? What message are you sending – directly or indirectly – about time off?

Your team is too valuable to screw up with a poorly executed unlimited PTO program. Build the systems to make it work.

I’ve sometimes seen a desire to throw $100,000 in salary and benefits at a “bandwidth problem” when it’s really just a prioritization problem.

Sometimes, hiring is absolutely the right decision. But sometimes, the better solution isn’t hiring, it’s doing fewer things better.

Before you hire, ask these questions:

• Are we trying to do too much? The instinct to say yes to everything creates artificial capacity problems. What if the issue isn’t a lack of people, but a lack of focus?
• Can we cut or pause lower-priority projects? Every initiative competes for attention. Which ones could you shelve without meaningfully impacting your core objectives?
• Are we clear on what actually created results? If you can’t identify your highest-impact activities, adding more people just increases the confusion.
• Could we streamline operations or automate some work first? Process improvements and automation often free up more bandwidth than a new hire, without the ongoing cost.

Hiring should be a strategic growth move, not a reflex to wrangle chaos. Sometimes the real answer isn’t adding people, it’s tightening focus.

One of the reasons I struggled in Spanish class was that I often confused the past tense with the imperfect tense. They looked similar, sounded similar, and both referred to the past… but they weren’t interchangeable.

Strategy and tactics are like that. Easy to confuse, but they play very different roles. It’s a common mistake, and I experience it often.

Think of strategy as the destination and tactics as the directions.

A good strategic goal should be simple and brief:

Increase brand saliency with Gen Z
Diversify donor base across three new geographic regions
Create a strong culture with above-average retention rates

The tactics are in the weeds: partner with Gen Z influencers, host fundraising events in X, Y, and Z cities, launch monthly employee surveys.

A quick gut check to help differentiate the two:

• If changing it would shift the overall goal, it’s the strategy
• If changing it would leave the goal intact but change how you get there, it’s a tactic

Strategy sets the direction, and tactics are the steps. If you and your team aren’t clear on the difference, you’ll end up debating details when you should be defining goals.

Sometimes, “building the plane while you fly it” is unavoidable. You just have to take off, move fast, and figure it out on the way.

But here’s the real question: Are you building the plane with duct tape or rivets?

Too often, “building the plane as we fly it” becomes an excuse to cut corners. “Just get it done. We’ll fix it later.” But later rarely comes and temporary becomes permanent. And you’re left flying a patched-together machine at 30,000 feet.

Yes, getting thrown in the deep end can be a great way to grow. But what if you used the chaos to take a beat and build something that lasts?

Even in the rush, you usually have a choice.

Ever look up a recipe and find a short novel before the recipe itself?

Or maybe you received an email from someone, and after three paragraphs, you still don’t know what they want.

Maybe it’s a report or memo that buries the top line info in fluff and filler.

One of the best ways to get a response, earn respect, and win is by getting to the point.

It doesn’t mean being cold – you’re still a human communicating with another human, so respect is a must. It means being concise and clear.

Say what you mean and say it early.