Questions To Ask If Your Dream Career Feels Constantly Out Of Reach


A dream career is a goal to strive towards. Forget the Monday morning blues – you just know that a role like this would see you going to bed with a smile every Sunday night. There’s just one problem – you’re not actually sure that ‘dream’ careers exist outside of, say, Hollywood movies and big business. Surely, the rest of us are doomed to trudge along in the dreaded 9-5? Or, are we? In truth, regardless of how high up the ladder they are, anyone can carve themselves a career to love. However, you can’t simply stumble into a job like this; you have to create it carefully for yourself. Here, we’re going to consider some of the most important questions to ask yourself in order to start doing precisely that.

# 1 - What are you Good at?
As soon as we start thinking about dream jobs, most of us jump right into considering our hobbies and private passions, but this is unfortunately where a lot of people fall short. For one thing, monetising your passions is often a double-edged sword, and can soon see you losing all the love you had in the first place. There’s also every chance that you simply won’t have the skills necessary to thrive in a career chosen this way. After all, a love for reading doesn’t mean you can succeed in publishing, just as a passion for medical shows probably won’t make you a great doctor. To overcome this glitch, it’s worth reframing the question from ‘What do I love?’ to ‘What am I good at?’ This is a vital distinction, and it’ll see you choosing a career based solely on what you can actually do. That way, you’re far more likely to feel comfortable, confident, and successful in your role, all of which will help you love your job.

# 2 - Where do Your Weaknesses Lie?
Dream careers should absolutely revolve around your skills, but you may soon fall out of love with any job if you don’t also consider your weaknesses. After all, understanding where you might struggle in a role can help you decide a) if you’ll need to put particular work into improving and b) if that required work is worthwhile. So, be honest – where do you struggle the most in the working world? Let’s say you have ADHD and struggle with tasks like focus and organisation. While there are luckily now fantastic work ADHD coaching schemes to help with all of this, you’ll probably still struggle to thrive or feel fully comfortable in roles such as team management. That knowledge allows you to strike a potential problem career off your list. Even more importantly, it allows you to lean into careers where these weaknesses can instead become strengths, such as careers in the arts, where creative restlessness can result in far better output overall. Or perhaps the opposite is true. Maybe you really struggle to conceptualise ideas and prefer to work in a structured, straightforward environment, such as manufacturing or role delegation. Simply be honest with yourself about what doesn’t work, and what that means for your desired work environment overall.

# 3 - Which of Your Skills Should You Actually Use?
It’s easy to assume (especially in keeping with our first point) that your dream job will be a career that utilises all of your skill sets. After all, this is a sure path to a role that allows you to truly shine. But did you know that you don’t necessarily need to apply all of your existing knowledge to be happy in a role? In fact, aside from setting the bar impossibly high, maxing out your knowledge base in this way could lead to an exhausting career that’s not actually as enjoyable as you think. Not to mention that it’ll leave you with very little progressive wiggle room (which can also have a major impact on job enjoyment!). It’s far better to cherry-pick the career skills that you can genuinely see yourself leaning into and enjoying. Who cares if you don’t end up using that IT course you finished in college, or you never put your leadership training to use? If those things don’t fill you with excitement, then replace them with more personally useful skills, whatever that means to you. Simply ask what skills you value the most, which knowledge sets you are most likely to expand, and where you can see growth within those specific interests. That way, you’re far more likely to end up with the strong foundations for a career worth loving.