A Goal Is Not a Script. It’s a Compass.

Of the many goals I’ve set for myself over the years, two stand out: Married by 27. CEO by 45.

One happened right on schedule. The other, years later.

This month, as I turn 45—nearly a year into my first CEO role and three years into marriage—I’ve been reflecting on what the pursuit of those goals taught me. Success isn’t about hitting a specific date on the calendar. It’s about having direction, staying committed, and accepting that some ambitions take the scenic route.

The Goal That Landed

In my early 30s, I hit a major career milestone: Partner at McKinsey & Company.

I remember the mix of pride and relief. Pride that the effort had paid off. Relief that the long nights and high-stakes meetings hadn’t been in vain. But almost immediately, another question surfaced: what now?

Partner gave me influence, but I wanted to make decisions, drive outcomes, and be accountable—the way the corporate leaders I advised were. In an operating role, your choices ripple through employees, customers, and communities. You scale your ability to drive change.

So I set a new goal: CEO by 45.

That goal gave me clarity. It shaped what I pursued, what I declined, and how I focused my energy. It didn’t prevent wrong turns—there were roles I didn’t get and opportunities that evaporated—but it gave me a way to reorient after each setback.

Fast forward: nearly a year into my CEO role at HackerOne, the timing aligned with the goal I had set more than a decade ago. And yes, I felt the same pride and relief I did when I made partner—along with a healthy dose of now what?

The Goal That Took Its Own Time

Not every goal happened on time. In my early 20s, I set a goal to be married by 27.

There were flaws in that plan. First, 27 was a semi-arbitrary number—far enough out to be plausible, but not so far that my biological clock would weigh too heavily. And second, to get married, you have to date. To date, you have to not be working 24/7. Let’s just say I didn’t structure my calendar with romance in mind.

So, no marriage at 27. In fact, there were years when I quietly wondered if I had missed the window. Instead, I got married at 42—at the right time, to the right person.

Looking back, the story isn’t as simple as “career first.” Yes, I poured myself into becoming partner and, eventually, CEO—and that left little space for dating. But marriage isn’t something you can schedule. It depends on meeting the right person at the right time. Even when I did make time to date, I held a high standard for the kind of partner I wanted and wasn’t willing to compromise on that. All of this pushed the timeline out. Yet when it finally happened, it was with the right person, at a point in my life when I could bring more perspective and stability to the relationship.

The goal that slipped was inseparable from the one I achieved. In the end, both came true—just on different timelines.

Goals as a Compass, Not a Script

The power of a goal isn’t in predicting the future. It’s in providing direction.

The CEO ambition was built deliberately: thousands of hours sharpening my craft, choosing roles that stretched me, and surrounding myself with mentors and sponsors who pushed me to grow. Mastery depends less on brilliance than on where you consistently put your time.

In my 30s, I didn’t know it would be HackerOne. I didn’t know it would follow several more years at McKinsey and a seven-year tour at F5. The goal was never a script. It was a compass that helped me recognize the right opportunities when they appeared.

Goals give you focus. Ambition gives you fuel. Priorities set the pace. Flexibility keeps you moving.

Advice to My Younger Self

If I could whisper back to my 30-something self—ambitious, impatient, discerning—it would go something like this:

• Set the goal. Even if it shifts, it gives you direction.
• Do the work. Mastery is built in the hours nobody sees.
• Stay open. The best opportunities often appear off the map.

What Now?

Just as past goals gave me direction—even when the timelines shifted—the ones I set now are less about fixed dates and more about guiding the impact I want to create, the milestones I want to reach, and the life I want to live along the way.

Naming a goal sharpens focus. Looking ahead, I’m working on three:

• Build a future where security outpaces threats.
• Take a company public.
• Explore every U.S. national park with my wife—plus 1–2 new countries each year.

These aren’t fixed endpoints. They’re milestones along a path. Even imperfect goals provide a compass.

I’ll leave you with the question I’m asking myself—one that applies as much to organizations as to individuals:

What goals are you setting today that will keep you moving forward, even if the route or pace changes?