Nov 13, 2022 4 min read

Making It To The Top, Or Not

Blog covering my thoughts on what defines a successfully career, and some of the things that I’ve personally encountered along the way.

Making It To The Top, Or Not

A little while back, the only thing that I wanted to be, and the only thing that mattered to me at the time, was to be "promoted" to a director level. I use the term "promoted" since to me at least, this was the only measure of success. At the time I knew that I was missing something, so the urge to prove my success became greater. But the reality was that I was unhappy, stressed as well as being at the point of depression. A large part of my depression was driven by the fact that I had not been "promoted".

Legacy View of Success

A lot of this view of success that I had stemmed from the legacy view that we have of having a successful career. Namely the corporate ladder. Where we start at the bottom and then work our way up to the top. And if we some how didn't make it near the top, then we weren't particularly successful in our careers. I'm not saying that this was correct (it's not), but this was typically how many of us used to think. Thankfully things are changing.

Times Are Changing

Fairly recently, the only way to make a success and further your career was through management. Numerous job roles hit a ceiling and that was it. It was either management, or you would be stuck at your level indefinitely. But thankfully things are changing. We now see many organisations having two career tracks or pathways. Namely the traditional management pathway, but also a technical pathway. This means those who are not interested in management, now have the opportunity to further their careers without having to get into management.

Management is Hard Work

At one point I was directly managing eight people. To me this was a successful thing. I was making progress in my career. Oh how wrong I was! Firstly, managing people is hard! It involves a lot of time an effort. Not devoting that time and effort is not only unfair to those who you are managing, it can also cause issues within the team(s) that you are managing. And this is exactly what happened to me, I didn't allocate enough time (there are reasons, for which I won't go into), and the end result was issues that came about. By the way, these issues fester over time, so aren't things that suddenly appear.

While at times there are great things to managing people, such as seeing people grow and you helping them to do so. There are the less glamorous aspects of managing people. And let me the first to say, they are not pleasant at all. There are some awkward and difficult decisions and discussions that you will have to have. So much so, that you would try do anything to avoid having them (which obviously is never the answer).

The other side is the non-people side of management. The stream of meetings. The numerous documents that need to be created. The countless presentations to create. To a really technical person, these will likely sap the live out of them. Things become dull and monotonous.

Back to The Story

And this is exactly where I found myself. I knew that I was missing something. I knew that this path I was heading down was the wrong one for me. And this is when I switched roles. I went back to doing the hands-on technical stuff. I had my motivation come back. I got excited about doing things again! And that urge to become a director? The only question I had was why I was so fixated on it. I realised that at that point, becoming a director was perhaps the last thing I really wanted to become. The real turning point for me, was realising that I didn't have to have the title of director to acknowledge to myself that I was making a success of my career. What I needed to do was stop and look around and see the things that I had actually accomplished. Most importantly the people that I had the honour and privilege of helping along the way. Helping them grow their careers. I was looking into exciting technical things again. Using this to help with my current role, but also helping those outside of my role, in my personal capacity. And the best part of all of it? I was actually having fun doing it!

In fact, I'd go as far as to say since getting back into the more technical side of things, I've felt that I've actually furthered my own career. I recently had the opportunity to at least take the shot of trying for a Director of Security role. I thought about it, and came to the conclusion that it just wasn't for me at the point of time. I still have loads to learn, help and share from the technical perspective. So to me, this means further growth of my career.


The point I'm trying to make is that success should be something that only YOU define to yourself. Don't let others do it, especially in the old way of thinking! We are no longer stuck in the 20th century way of thinking. The way we work and the way our careers grow has radically changed. So don't be like me and attach yourself to labels such as director, VP, etc. While achieving those labels is a great undertaking, and certainly a great success, it is no longer the ONLY way to define a successful career. And while I write all of this, I still in some part still attach my own success to these labels, something that I'm trying to work on reminding myself that this should not be the case.

Just to point out that the people fulfilling the roles of the likes of VP, directory (or any management role) are doing an enormously important job. These are at times incredibly difficult roles. But the point I'm trying to make is that they aren't the only roles to define success and they most certainly aren't for everyone.

The final thing to make note of, career pathways are not rigid. They can, and perhaps should, adapt over time. Mine certainly has! Who knows, maybe in a couple of years time I might be drawn more to the management side of things, as opposed the technical side. So bear this in mind. Far too often I think we define success on labels, numbers, and other such measurements, rather than the most important measurement of all, accomplishments.

Also remember, titles are just that, titles. What you actually do, and what you are responsible for are far more valuable than any string of words (which many make up in things like their LinkedIn profiles any way).

Sean Wright
Sean Wright
Experienced application security engineer with an origin as a software developer. Primarily focused on web-based application security with a special interest in TLS and supply chain related subjects.
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