Advice, Software Engineer

The Real Reason Why You Haven’t Gotten Your Dream Job

And how to go about getting it!

“Have you found your dream job?”
I don’t know why, but I have a strong curiosity about people’s careers. In the midst of a 1:1 meeting, I asked my colleague that question. She looked at me puzzled but then replied with an unwavering certainty, “No, not really.”
Over the past decade, the above conversation replayed many times, with different people, at different places, but the answer was almost always the same –
No, not really…
Now, I can hear you asking me, “Dear Isabel, have you found your dream job?” My answer is “Yes, many times…” It’s not a short and sweet answer. Let me explain - I’ve found my dream job many times in my career. My dream job ten years ago was certainly not what I am doing right now. Likewise, my dream job right now will not be my dream job in a decade time. Because I know for a fact that I will grow out of my current job and will be ready for something different in the future.
The reason why you haven’t found your dream job yet is pretty simple - you don’t know what your dream job is. The use of the word “dream” have us fooled, it leaves us in a crippling place, optimistically and wishfully waiting.
Don’t wait no more. There is no better time like now to be in the driver seat of your own career. Today, I will share with you a simple two-steps process; first, how to understand what you actually want as a dream job, and second, how to go for that dream job in a pragmatic way.

Step 1: Know what your dream career looks like
Perform a 360º view of your dream career
My first advice is to perform a 360º view of your dream career. There is really no time like now to have clarity on what you really value in life and what your aspirations are. When times are good, you might be thinking everything is fine. You feel positive about most things. When times are bad, your mind really starts differentiating what’s important from what’s not. Your sense of self is amplified.
For example, you thought you were happy with your current job because of office perks like free food and funky office space. Your colleagues were a social bunch with whom you hung out outside of work. As a result, you generally looked forward to coming into the office each day, even when the job itself was mundane. But now, you realise that office perks and social aspect of the job do not matter as much as how you are spending your time and what impact you’re making to your community through your work when the world is in the midst of a pandemic.
Going through adversity gives you a good chance to reevaluate your assumptions and reset your priorities in life.
With that in mind, when performing a 360º view of your dream career, I’d encourage you to look at it from two main perspectives and six different angles - an internal perspective, your values, aspirations, and talents; and an external perspective, the kind of industry, environment and people that you’d like to work with. In other words, looking from within as well as looking outside-in.
Looking inwards - Values, Aspirations, Talents
Looking outwards - Industry, Environment, People

Looking inwards - values, aspirations, and talents
Here are some good questions to provoke your thinking when looking inwards include:
Values: Who do I want to be when I am not seeking validation and approval from others?
Values: When I look back at the past few years of my career, what were my proudest moments?
Aspirations: What am I doing when I am at my best?
Aspirations: If an external factor - such as money, recognition, social status - do not have any influence on what I do, how would I like to spend my time?
Talents: What skills come naturally to me?
Talents: What do people reach out to me for?

Looking within yourself is a reflection exercise; it’s when you quieten down voices in your head, still your mind and give yourself permission to feel your emotions and understand who you really are, you will discover what really fuel your soul. In fact, it is very liberating to not care about how other people perceive us, the social norms and conventions and just acknowledge your inner desires.

Looking outwards - industry, environment and people
Next, it’s time to take a look at the outside world - an outside-in perspective. Your career doesn’t happen in a vacuum, even when you’re a solopreneur or a startup CEO. As long as the law of supply and demand exists, there is going to be interaction and collaboration with others at varying levels in order to provide value through your job.
Firstly, take a look at what industries are thriving right now and what industries are aligned with your values, aspirations and talents. You need to realistic here; while you might say I love travelling and my life goal is to share my knowledge of travelling and to witness people enjoy new experiences that come with travelling, it’s going to be almost impossible to find a job in that industry when the whole world is in lockdown.
But before you completely discard the idea of your dream job, remember that whatever is happening right now is temporary. We will get through this pandemic; we don’t quite know how and when exactly, but we will definitely get through this. With this perspective, start thinking and preparing yourself for what you think you will need in order to get into the industry of your choice. Do research, educate yourself, learn what you can, so that when the time comes, you will be equipped with necessary skills and knowledge and be able to make a move to the direction of your dreams.
On the other hand, if the industry that you’re interested in is thriving during this time, such as health care, think about how you can offer you existing skills, experiences and knowledge so you can position yourself for success.
Next in the list of things to look at is environment. What type of environment would you like to work in? You might think this is not so important given almost everyone is working from home and working remotely. Let me remind you again that this situation is only temporary. It’s also important to acknowledge that after the pandemic, the way we work will be changed and we will never completely go back to how we worked before.
However, a working environment is much more than a physical location of your workplace. It’s about the culture and values of the workplace. Some questions to ask are: what are unspoken rules and unwritten laws of the company, how do decisions get made, how are people motivated and treated, what behaviours and qualities are valued by the company and so on.
The last piece of the puzzle for an outside-in perspective is people. People here do not only refer to your potential colleagues and team members, it also includes customers, vendors and partners. The most important aspect of People is the leadership that runs a company and the immediate manager that you’ll be working for. A Gallup poll of more one million U.S. employees concluded that the number one reason employees quit their jobs - a whopping 75% - is due to a bad boss or immediate supervisor. So how do you make sure that the tenure at your dream job isn’t cut short because of a bad boss? Leaders are humans too, and just as there is no flawless person, there is no perfect leader.
John Maxwell talked about 5 levels of leadership, with level 5 being the highest of the scale. But even the level 5 leaders aren’t perfect. The key is to find out what kind of leaders will bring out the best in you and help you achieve your goals. To help answer that question, you might like to ask yourself about the kind of people you enjoy working with. Are they those who are extremely competent, strive for excellence and expect the same from you? Or those who value harmony? Or those who give you much autonomy with little direction? Or those who provide you with constant reassurance and validation?
Different companies and leaders attract different types of people and when you pay attention to existing people that the company hire and promote, you can find out whether they are aligned with the values that you have and the aspirations that you want for your own future.

Second: Go forth and get that dream job
Now that you’ve gone through the 360º overview of your dream career, give yourself a pat on the back as understanding what you want is the most important step to making a progress in your career. Remember to write down your insights so that you can refer to them quickly and easily. This is where having a personal development plan comes in handy.
Whether you’re a manager or an individual contributor, you need to take control of your own career and have a personal development plan. If you don’t know where to start, you may check out my Career Planning Starter Kit.
With your new-found insights and a personal development plan, perform research on the market for companies that may be a match for what you’re looking for. Glassdoor and LinkedIn are a good place to start. After your search, if you are lucky, you will find one or more companies that are completely aligned with what you’re looking for.
More often than not, the reality though is that you may not find an exact match. Over the past 20 years in my career, I have never once worked for a company that’s 100% match of my dream job. Some companies align with my values, others align with my talents, I have worked for industries that were not my preferred choice, and I have been at companies where I didn’t feel like I belong. What I found have worked for me is that through the 360º career review, I was able to obtain clarity on what I was after, and prioritise them.
You may even find that the current company that you’re working for is matching a few things you desire but is not matching some. For example, the company shares the values you’re passionate about, you are able to utilise your talents to make an impact but it’s not in the industry that you’d like to work in. Upon realising this truth, your can decide on your next step - whether to start looking for a new job in a different industry, or whether to stay with your current company but build on the knowledge of your desired industry, or something else.

Is it a dream job if it doesn’t feel dreamy?
When I was young, I wanted to be a singer. Being a singer was my dream job. Because it felt dreamy for a five years old girl. Today, if someone appeared on my door step and asked me to quit my job in the tech industry and hop onto the entertainment industry to begin my dream job as a singer, I’d politely have to decline.
That’s the thing I want you to know. There is nothing dreamy about a dream job. Don’t be fooled by the idea of what your dream job could bring you - fame, freedom, financial benefits or whatever it may be. If you really want to get that dream job, you need to put in the hard work. You need to test the water, to understand whether it’s something you want. You need to be realistic. And last but not least, you need to take action. Don’t just dream, do.
Let me leave you with words of wisdom from the world’s biggest dreamer of all times, Walt Disney.
All our dreams can come true, if we have the courage to pursue them.
― Walt Disney

Do you want to learn how to grow your career? Of course, you do! I’ve worked in the tech industry since I started my career almost 20 years ago and I’ve seen first hand how technology is always changing and advancing. Likewise, your career needs to be evolving with time. That’s why I’ve created a Career Hub where you will find all the resources you need to not only stay current in the tech industry but also help you grow your career. To make it most relevant for you, I’ve categorised the resources into 3 different sections:
Individual Contributors (eg: Software Engineer, Developer)
Technical Leaders (eg: Tech Lead, Engineering Manager, Software Development Manager)
Executive Leaders (eg: CTO, Technology Director, General Manager, CEO)

Career Guide for Software Developers