When I was about twenty-five, I attended a seminar where a speaker offered a definition of success that I later learned came from Earl Nightingale, often called the Dean of Personal Development. Success, he said, is the progressive realization of a worthwhile goal.
At the time, it sounded abstract. I thought success meant status, good health and money, and the feeling of having finally arrived.
Now I think I get it.
The key word there is ‘progressive’, because people don't get their energy and the feeling of success from standing still, at work or in life. They get it from moving forward.
Nowhere is this clearer, or more misunderstood, than inside organizations.
Where Promotions Fall Short
Most corporate career models rely on a ladder of promotions, and there is nothing wrong with that. Organizations need structure. Someone has to own decisions, lead teams and carry accountability. A promotion also sends a message that this person has done better work and solved harder problems than most around them.
The trouble starts when the promotion becomes the only measure of growth, for the organization and for the people in it. Organizations assume a new title will keep people engaged. People assume a new title means they have grown. Both treat growth as a series of fixed checkpoints, and that fails people in one of two ways.
1. The Arrival Fallacy (When Milestones Arrive)
When a high performer hits a milestone (a promotion or salary bump), adaptation sets in. Within a few months if not weeks, the new title and compensation become normal. And worse, if the day-to-day nature of their work hasn’t fundamentally changed, the thrill of arriving soon turns into the feeling of being stuck, especially when they know their capability has outgrown their daily tasks. Psychologist Tal Ben-Shahar calls this the arrival fallacy.
2. The Cost of Delayed Rewards (When Milestones Lag)
The second failure is the reverse: the milestone that comes too late, if it comes at all. Economists talk about this through life-cycle models: money and resources don’t have the same value across your life. Regular rewards in your twenties and thirties give you choices and the freedom to take risks. You feel successful because you can see yourself moving. But the same rewards years later in life give you a feeling of regret or at best relief, like settling an old debt, a kind of pay back for all the past stress because the years when you needed that reward the most have passed by.
Organizations that don’t recognize these two gaps risk their best people slipping into minimum effort mode and eventually leaving.
What Actually Keeps People Moving
If titles quickly lose their shine and delayed rewards leave you with regret, what actually drives lasting fulfillment and high performance?
In her research at Harvard Business School, Teresa Amabile identified the Progress Principle: the single greatest driver of daily motivation is the feeling of making progress on work that matters.
But progress on what? Doing the same work faster feels like progress for a while, until it doesn't. For progress to keep feeling real, the work itself has to get harder.
The aim isn't fewer problems. It's moving from simple problems to harder ones, one step at a time. As physicist David Deutsch argued in The Beginning of Infinity, civilization only advances by solving problems that create better, harder problems. David Epstein highlights a parallel in Range through the concept of ‘desirable difficulties’: the idea that some struggle helps us learn more deeply. Inside organizations, people feel successful when they move on to harder challenges.
A simple way to see this is three levels of work, roughly matching junior, mid-level and senior roles. At level 1, people follow set procedures. At level 2, they redesign how the work flows. At level 3, they work on overall direction. In short: operational, then systemic, then strategic.
When people stay at one level longer than they need to, whether by their own choice or the organization's, their work stops stretching them. Real career growth comes from being stretched: the problems you solve have to keep getting harder.
The question for senior leaders is how to keep people moving up those levels without waiting for a title change. That means changing how work is handed out and how people are rewarded.
Check problem difficulty, not just title or tenure: Don't wait for annual cycles to change responsibilities. Track the complexity of problems your critical talent is solving. In my view, if a top performer's work hasn't gotten harder in a long time while their skills have clearly grown, they are a flight risk, whatever your retention policies say. So when individuals demonstrate competence, give them harder work straight away, rather than making them wait for the promotion cycle.
Pay for skill, not just team size: Many career ladders push strong specialists into managing people just so they can be paid more. Some of them are great at their work and have no wish to manage. Pay people for what they can do, not for how many people report to them. Build separate paths for managers and specialists, with equal room to grow.
However, not every manager can redesign career tracks or pay bands. Those decisions sit higher up and move slowly. But every manager decides what work their people do tomorrow. We can give them harder problems before they ask and clear their way so they can see their own progress. That is often a bigger reward than the title they are waiting for.
Titles tell people where they stand. Harder problems tell them they are moving.
And if you're the one waiting for a harder problem, no organization or manager can do your growing for you. They can open the door to harder work, but only you can walk through it. Waiting for someone to hand you a bigger challenge, or for the next promotion cycle to prove you've grown, is handing your career to someone else.
Now back to when I was twenty five. I think I understand now what the speaker meant. Took me years to understand that success isn't arriving at a finish line, because there isn't one. It is the progressive realization of a worthwhile goal: one harder problem after another.