Why Most Career Plans Fail — and How to Change It

Most people who consider their career to be important spend a significant amount of time thinking about it, defining career paths, making plans…and yet those plans often fail. I will explain why, and how to design a better career model which actually works in real life, not just on paper.

The Perfect Career Plan?

When I entered university, I knew how my career should look like: Undergraduate degree, then straight into the financial industry. Three years as an Analyst, then Associate, and so on. It was all pre-defined, as those corporate careers very often are, so obviously it was all down to me: If I just work hard enough, things will work out. Input — Output; Action — Reaction. Simple, right?

I graduated in 2007, then started working in my first investment banking job. And I hated it — not so much the work, but the work culture in that place. After three (!) months I knew I had to leave, and I did: I went straight into private equity. This was the first diversion from the original plan, but I regarded it as an honour; after all, private equity is considered off limits until you have proven yourself in banking first. So I was happy.

Then, September 2008: Lehman Brothers is bankrupt. And Merrill Lynch, and many other banks going under along with them. My world was shaking: How could this be happening? I was doing well in my job, but the market segment I was in was broken so that, in 2010, I moved to another firm where business was still happening — my second diversion. And finally, in the job at a hedge fund which was widely regarded as the the golden ticket in the industry, I realised I no longer knew why I was doing it, why I was in finance and what purpose it held for me — I realised I looked for meaning in my work, and simply could not see it. This frustrated me deeply and I finally reached my breaking point, so I left on a Friday with no plan whatsoever, no direction. I only wanted to be out to be able to figure out what is next. Calling this my third diversion is a bit of an understatement.

The One Fatal Flaw in Most Career Plans

So let’s recap those three diversions from my excellent plan:

1. Changed company because of bad workplace culture
2. Financial industry meltdown
3. Lack of purpose

Now, which one of those could I have anticipated when planning my career as a budding undergrad? Could I have known the workplace culture in that particular bank, that particular office, that particular team? How about the financial crisis? Or the fact that I would have a serious awakening moment at the age of 28, prompting me to reconsider literally everything?

The answer is: Unless you are a psychic (a real one, not one with the crystal ball), there are events in your career which you cannot foresee. And here is why:

Life is not linear. B does not follow A, and more detailed planning won’t make it so.

The reason why almost everyone is led to believe that better planning (A) will lead to success (B) is largely to blame on the way we are educated and the way humans like to look at the world. We believe that if we add the right number of variables to an equation, it will account for the complexity of the world and enable us to make near-perfect prediction.

This is delusional thinking, because we do not account for complexity, meaning the interaction between those variables, the number of potential variables (hint: the answer is infinite), plus the element of time at which those interactions occur. The thought model which explains these relationships is called Systems Theory.

Without going any deeper into the theory, what does this mean for your career?

It means we have to accept that we cannot control every aspect of our lives. This realisation will enable us to develop a working career model.

Now, I can imagine this is not what you wanted to hear! It is not what I wanted to hear when I first heard it (“But I am the master of my own life!”),but consider this: In a linear world, the responsibility of your plans not working out is your fault. “If you had worked harder, you would have been promoted sooner.” “If you had studied a different degree back then, you would have been able to have the life you wanted”. Sounds familiar?

Once you realise that this model of the world is an incorrect representation of reality, those very common accusations become meaningless and, in a way, quite amusing.

Does this mean you are home free because life is just beyond your control and therefore you cannot do anything about it? Is career planning just an illusion? Not so fast.

How to Plan Your Career in the Face of Complexity

So how do we plan in a world where many things are outside of our control, and the complexity is set to throw a wrench into the gears of any carefully-constructed machinery?

For many people, career goals are very position-specific (“Associate in an investment bank within 6 years”). Some people even know which company they want to work for, and what they will be doing there. Those plans, as many of us know, hardly ever come to fruition. They depend on too many things we cannot control and most likely even know about at the outset.

Instead, let’s look at this: What do we want from our career? Is it really the Associate title in the bank, or is it something else? The lifestyle, the intellectual challenge? Whatever it is, those are your real career goals!

Having a specific job is not a goal in life. The desire behind this wish, however, is a valid and achievable goal.

So, to really come up with a career plan, do the following:

1. Think about the dream jobs you thought of when starting out.
2. Write down what these jobs mean to you — this can be literally anything.
3. Group those terms if some are related; e.g. emotional, tangible, etc.
4. Now, look at those items / groups: Which career paths would help you achieve what you have discovered as your driving forces?

This is the first step; it is meant to provide you with clarity on what really motivates you intrinsically, and which careers would be suitable for you based on those criteria. In general, you will find that your motivation is much higher if a career harmonises with your personal driving forces, and you are much more likely to succeed.

By now I am sure you see the difference between focusing on the manifestation of your true desires (“Associate in an investment bank”) compared to looking and nurturing whatever made you think of this career in the first place. It is this shift in mindset which will enable you to have a fulfilled career — because there are more than just one way to get there!

I spent many years going through this transformational process. After my first three diversions in my career, many more followed until I shifted my mindset to focusing on my personal drivers.

Once this had happened, I realised I was not diverting — I was just finding new ways to the same goal, only that I could it see it now.

What are your personal drivers? Have you found them, and have you managed to transform your career yet? Or do you need help? I would to hear your story!

Here are my LinkedIn and my Twitter — get in touch!