4 reasons you are successful and unfulfilled

James (name and details changed to respect his privacy) is, by most measures, a successful executive in a multinational company. He has a senior position, makes good money, is married to the woman he loves and has two beautiful children. He works with interesting people and his job lets him travel the world. When you meet James the thought that comes to mind is that he’s got it all, and he certainly plays the part. He talks about the projects he’s led and the successes he has had. He shares with enthusiasm the details of the latest meeting with a famous figure, or some world leader.

In our first session together, I asked James why he thought he needed coaching. He answered that he thought having a coach is a great way to become even more successful (which is true!). This answer, a variation of “I’ve come this far and I want to go further”, is one I hear often. And it’s an answer that seems obvious, after all we’d all like to move forward in life. 

After working with James for a few weeks it became clear that he was running out of steam. He wanted a coach because he wanted someone to push him. He was losing his internal drive, and this was frightening for him. He wanted someone to help him do what used to be natural and exciting for him, but was no longer so. I could sense in James a feeling of no longer being truly happy about his life.

One day, emotionally drained, you realize that you’re fighting very hard to keep pushing forward

I’m guessing that if you’re someone who has been successful in your career, you will at one point have felt exactly the same way as James. And it’s a feeling that creeps up on you. You get used to going through the daily motions, and you’re moving ahead every couple of years so you don’t have time to stop and reflect about whether the next career jump is something that’s good for you. Then, one day, emotionally drained, you realize that you’re fighting very hard to keep pushing forward. It’s not as exciting as it once was, and it feels exhausting to go through one more day. To make matters worse, you are reminded regularly by the people you meet how lucky you are and how great it must be to be you. 

Where does this feeling come from? Why is it that after so much hard work to achieve the goals that you set for yourself you find that you are feeling empty and unfulfilled?

There are many reasons I’ve come across with people who are, by most people’s definitions, successful. I want to share four of them with you today, to help you think about whether you have fallen into one of these “success traps”.

1. You want more

You live in a nice house, which you own. You drive a nice car and you managed to get your kids into that great school with the amazing facilities. Last summer’s vacation to Switzerland was full of great memories and your family loved it.

But the house, while it’s comfortable, isn’t quite the house you dream of living in. The backyard is small, and the kids could really use a bit more space. The neighborhood is nice and people are friendly, but you hoped for something more upscale. Switzerland was great, but there was a nicer hotel that was just outside your budget.

This feeling of “if only I could reach this next milestone I would feel like I’ve made it” is a very common trap that many people fall into. Inevitably, when they do reach the next goal, happiness will feel like it lies in the very next milestone after that, just out of reach. It’s a never ending cycle that requires deep work to break out of. It's a problem because it's driven by a feeling of inadequacy, of feeling less than they are.

Often, when someone realizes they are stuck in this cycle, they will say something like: “but this feeling of being inadequate drives me forward. It is what makes me successful so I don’t want to lose it.” In other words, they would rather be unhappy and successful in the eyes of others, rather than happy and living modestly. But even that is an unnecessary distinction because you can be both satisfied and highly motivated.

2. You assume a linear path towards success

People who are trapped in a cycle of growth coupled with deep dissatisfaction often look at their life and career as being on a single, well planned, well managed path. They are very clear on where they’re going and success is just about getting there. They use metaphors like scaling the next summit, or driving faster on life’s highway. Sometimes that comes with a feeling of having already lived their future before it has actually occurred. They’re already bored of the things they haven’t yet experienced.

As a result of this way of thinking, people like that miss out on many opportunities and experiences that don’t fall within their narrow definition of what success for them looks like.

If you find yourself thinking this way, try thinking of your life as an adventure to be experienced and created day by day. You can still have plans, but plans are more guideposts rather than strict paths to walk. The more you find yourself holding on tightly to the future, the more you should try to let go and live in the present moment.

Another way of thinking about this is to let go of the concept of success as a single destination. Success is a feeling, and millions of different paths will get you there (and often not the one you’re on). Life is only linear when you look back, but going forward it can branch into so many different unexpected directions.

3. You measure your life by outdated metrics

As a young adult, it’s perfectly normal to think of success in terms of money and power. First of all, becoming financially secure is the most pressing need you have at that stage of your life, and that goal usually stands between you and other things that you might want to do in life.

It’s also the goal that you’re most exposed to at that stage of your life. Most of your school years are spent thinking about getting your grades up so you will be accepted into a good university in the career path of your choice and then land a good job. It’s a series of milestones whose primary goal is financial wealth. 

What happens, though, is that we get stuck with these same metrics all of our life. They become the driving force for every decision we make. The reality however, is that as our life evolves, our needs change as well. These needs evolve as a result of many things. Maslow’s famous hierarchy of needs is a great framework to help you think about “what’s next?” (there’s a long way to go after financial success). Another major influence is the life-stage you’re in. As we get older we enter different life-stages and assume different roles. If we’re still trying to do at 50 what made us happy at 30, we will feel a deep disconnect.

4. You fear the unknown

Whether we like to admit it or not, one powerful factor that holds us doing the same things even when we’re unhappy, is fear of the unknown. After all, the path we’re on has worked for us well, so why abandon it? We’re bombarded with stories of people who “had it all, and threw it all away”, under a subtext of “what an idiot”. People are always reminding us that we’re doing well, and that any deviation from what we’re doing would be considered not doing so well anymore.

Even if we get to the point where we think something should change, we’re then faced with the conundrum of “change to what?”. Where we are now feels familiar, and the familiar is always more welcoming than the unknown, even if it’s not necessarily a great place to be.

To complicate things further, highly successful people are driven by the need to be successful and, coupled with that, the fear of failure. And so, why let go of something that is working in order to venture somewhere that promises nothing but the risk of failure?

The human experience contains many layers of awareness and understanding, and while we might be aware of some fears there are others deeper still that influence our decisions in a big way. Do the work to uncover these fears and understand how they influence your life so you can take back control of your future.

Closing words

Success brings with it many rewards, but also many challenges. The most difficult of these challenges are the ones inside of us. After all, we hold inside of us the goose that lays the golden eggs, and as Aesop’s fable tells us, you should not mess with the goose.

But what happens when golden eggs are no longer enough? The fable doesn’t go that far. So I invite you to go on your own adventure, risky as it might feel right now, and find your answer to that question. After all, there’s no redo in life.

If any of these resonated with you, share your thoughts in the comments (or in a private message if you prefer).

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