By Julian Lighton
Many senior leaders fail to experience fulfillment, not because they aren’t successful, but because they haven’t stopped to define what success means to them.
Intro: “Am I successful?” I have often asked myself. I am sure you have too. How would I know? After decades of hard work and achievement, many senior leaders face a dilemma – their ‘success’ on paper simply doesn’t align with a sense of career fulfilment. Many leaders fail to experience fulfilment, not because they aren’t successful, but because they haven’t stopped to define what success means to them.
The Success Paradox
My answers have varied by the stage of my career I was in, the people I spent time with, and through the process of research and reflection. These answers have shaped my opinion of myself, my identity, and a good deal of my happiness. If you are going to spend a third of your life on something, shouldn’t you know what success looks like? Shouldn’t it feel like success?
So, how can you define success to achieve true fulfillment at the top of your game?
Success is paradoxical. You can feel successful from the size of your bank account, the title after your name, or the way others laud you, but you can also feel empty, sad, and full of regrets.
There are, however, some ‘symptoms’ commonly associated with the success paradox, and spotting these can help you assess why you might be feeling unfulfilled:
1. Deferring happiness
It’s easy to fall into the trap of postponing happiness and fulfillment to a future point, often tied to achieving a specific goal or circumstance. It’s the belief that “When I get X, I’ll be happy,” but the X constantly moves further away, leading to a perpetual state of waiting for happiness rather than experiencing it in the present.
2. Not knowing what you want
Not knowing what you want or having misidentified it can cause extreme pain. A sense of time running out and of life force wasted can bring severe consequences in other areas of life like family, friends, and health. If these other life pillars are neglected, many leaders end up with external accomplishments but internal emptiness or a complete imbalance with success in one area but failures in others.
3. Losing sight of “enough”
One of the most common issues among high-achieving professionals is the inability to know when enough is enough. They cannot switch off the pursuit of money, power, prestige, and influence because their identity has become too tightly bound to achievement. This is the identity trap. You start to believe you are your job title, your income, your corner office. You achieve one milestone and immediately raise the bar again.
4. Achieving loneliness
Many high achievers climb the ladder only to find themselves isolated at the top. This kind of loneliness often stems from an achievement-driven life that lacks relational intention. If you’ve spent years optimizing every moment for performance and progress, you may have inadvertently deprioritized the people who give your success meaning.
Measuring Your Success
So how can you combat these symptoms of the success paradox? How can they recognize that you’ve gotten to where you wanted to be – and enjoy it?
It’s time to pause and look back on how far you’ve come. The goal is to recognize your success and let yourself be satisfied with it, rather than being restless. Here are four steps to achieve this:
1. The Success Thermostat
We all have an inner thermostat for different aspects of our lives, such as:
- Career success
- Personal health
- Relationship with partner
- Relationship with friends
This thermostat regulates our view of our life experience. It is adjustable, but only with awareness and internal work to adjust our view of reality.
Where is your success thermostat set? Think of the life pillar categories above that you want to focus on. Think of a range between zero and one hundred, with one hundred being the most successful and self-fulfilled. Where are you now? Why? What is driving this? What would more success look like, and how different would you feel?
2. Who came on the journey with you?
Success is rarely solitary. Whether you closed the deal, finished the program, or started your venture, who helped get you there? And whom did you enjoy it with? Take stock of how your network has:
- Grown in numbers and breadth, and
- Increased in quality and depth of relationships.
Write that down, and then answer these two questions:
- Who are the core five or so people who have helped the most? Have you thanked them? When was the last time you did so?
- How have you learned to be better at relationship building (earning trust, conveying warmth, understanding others) with them and others? What could you do differently here? What does this tell you?
3. Make meaning of success
If you make the key shift from asking “What did I achieve?” to “What did it mean?” and “What did I learn?”, you’ll be closer to enjoying true success and feeling fulfilled. Take time to reflect on these questions about your success. Write down your answers.
- Has it brought you closer to being the person you want to be?
- Does it reflect your values?
- Has it connected you with others?
- Would your twelve-year-old self be proud of what you have become?
- What would your seventy-five-year-old future self say about where you are?
4. Celebrate success
Even when people reach extraordinary heights, they often don’t stop to celebrate. You don’t want your life to be only early mornings and hard sprints. It can’t just be discipline and struggle. You not only need to win, but you need to enjoy the win. Ask yourself:
- What reward motivates you?
- What symbol would you use to mark your progress?
- Whom do you want to share this with?
- What’s a small but meaningful ritual you could adopt for finishing a goal?
Changing your Perception of Success
Career success is a matter of your individual perspective, and, being happy with what you have achieved is a choice. By actively measuring your success with meaningful metrics that matter from your own perspective, and by celebrating it in ways that reinforce connection, purpose and joy, you will not only get what you want out of your career but also know it when you do.
Julian Lighton
