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© 2026 Rob McKinnon.
All rights reserved.

Chapter 9

How to Navigate Your Career

Years ago I was hailing a cab from downtown Chicago to O’Hare airport. Cabs were scarce, so I ended up sharing one with a stranger who, it turned out, worked for The Wall Street Journal in New York. It didn’t take more than a few questions on my part — and openness on his — to learn that he was frustrated at his job and quietly wondering if he should make a change. As we headed west on the Kennedy Expressway, I offered him some free coaching.

By the time we pulled up to his terminal, he was looking at his career through a different lens. Not because I had answers, but because the right questions had finally surfaced.

The Leadership Challenge

If you’re reading this chapter, there’s a good chance you’re contemplating a change in your own career. You wouldn’t be alone. Two or three times a month I sit across from someone who is. Maybe one of these is true for you:

  • You’ve been let go.

  • You’ve been approached about a promising new role.

  • You’re no longer growing and want more challenge.

  • For one reason or another, the future doesn’t look good where you are.

  • You’re burned out and need a change.

  • Or something else entirely.

Whatever the cause, you are evaluating the part of your life that commands more hours than any other single activity. That alone deserves intentionality. On autopilot, we tend to reduce our criteria for a new job into two variables: title and pay. Bigger title, better number — done. But for your long-term fulfillment, those two variables won’t carry the weight you’re putting on them. When the next opportunity for change comes, it pays to be as intentional as possible.

The Leadership Opportunity

Before we consider the questions I asked my cab companion, let’s look closely at the word “vocation” itself. When most of us hear vocation, we think of something we make happen - climbing the corporate ladder. We think, “vocation is something I define and do. It’s how I make something of myself.”

I gained a different perspective on career years ago, reading Parker Palmer’s little classic Let Your Life Speak.1 Palmer reminds us that the root of vocation is the Latin vox — “voice.” Navigating vocation well means pausing to listen for that voice that is calling you into the future. We capture this meaning when we say someone is “living out their calling.”

So, a first question to ask is: what is that voice calling you toward? I want to suggest it is calling you toward an intersection of two primary roads that cross one another, and a third road that also matters but isn’t as decisive as the first two.

The two primary roads are 1) your Great Passions and 2) your Great Abilities. Each of these requires some time to truly discern. We don’t come right out of high school or college and have clarity on either of these. In fact I would suggest that most of us don’t figure these out until somewhere in our early to mid-40s. But we can be intentional about discerning them, and leaning into them more, as we listen to that voice calling us.

The First Road: Your Great Ability. Here’s the question to ask yourself: What am I better at doing than 95% of the people I know?

You’re good at many things. But what rises to the top — what is truly unique about you; what sets you apart from others? This ability can be subtle and nuanced. One of the challenges in discerning your great strength is that you will tend to assume, “Well, can’t everyone do this?” You won’t see it as special because it comes so naturally to you.

This is not necessarily a technical skill. As a leader, your greatest ability is often more about presence than performance. It might be the way you make people feel safe enough to tell you the truth. It might be the way you can walk into a room full of conflict and lower the temperature without saying much. It might be a knack for seeing two steps further around the corner than anyone else on the team. These are real abilities, and they can be more valuable than any technical skill on your résumé.

The Second Road: Your Great Passion. The question for this one is just as direct: What do I love doing so much they wouldn’t have to pay me to do it?

This is the activity, or the way of being, that you reach for every chance you get. It’s fun. When you’re doing it, you feel alive and you feel free. Time bends a little.

The Intersection of Your Great Ability and Your Great Passion. Now let’s put these two together. They intersect where you are doing that thing that you are so good at and that you love to do. They are opposite sides of a flywheel.

Think about any GOAT2-level athlete you admire. I’ll use Michael Jordan, watching him in the Netflix documentary The Last Dance. Jordan was one of the greatest at basketball. And Jordan loved to play basketball. For him it never felt like work. What do you do with something you love? You do it as much as you can. So he played all the time. What happens when you play all the time? You get better. What happens when you get better? You have more fun. Can you see the flywheel effect of these two characteristics of passion and ability and how they feed one another?

Every chance you get on your vocational journey, listen for that voice calling you forward. Whether in your existing job or as you change jobs, the goal is the same: move closer to that intersection. Closer to the place where what you do best and what you love most are the same activity.

The Third Road: Compensation. The third road towards the intersection of your calling is compensation — being rewarded fairly for what comes out of your great ability and great passion. I said earlier this isn’t as critical as the first two, and you might push back with “but Rob, the money is very critical!” In ways, of course, it is. We all need to make a living,

But survey after survey tells us the same thing: compensation is rarely what workers name as the most important thing in their job. If you are working at the intersection of your great passion and your great ability, I believe you will find a way to earn a satisfactory living.

Your vocational journey is too long, and the hours are too many, to navigate on autopilot. Every time you come to a fork in the road of your career, listen for the voice. Discern your great ability. Tune into what you love to do. Make a move toward the place where they meet. You will likely be rewarded in more ways than just your paycheck.

The Autopilot Leader

The Intentional Leader

Treats vocation as something to engineer through willpower and ladder-climbing

Treats vocation as a voice to be listened for — a calling to be discerned, not manufactured

Evaluates a career change primarily on title and pay

Evaluates a career change against the intersection of great ability, great passion, and fair compensation

Dismisses their natural strengths because “anyone can do that”

Pays close attention to what comes naturally to them but is rare in others

Chooses roles for the compensation, then tries to manufacture passion and ability afterward

Clarifies passion and ability first, then trusts that fair compensation will follow

Notes
  1. Parker J. Palmer, Let Your Life Speak: Listening for the Voice of Vocation (San Francisco: Jossey-Bass, 2000).

  2. GOAT: Greatest Of All Time

© 2026 Rob McKinnon.
All rights reserved.