In Pursuit of the “Dream Job”: Why Does Choosing Your Ideal Career Seem So Difficult?

A common theme I’ve noticed when speaking with other people in my age range (20s to early 30s) is that we all strive to find our “dream job.” Some may already have an idea about what their dream job is and are actively pursuing their career of choice. But others are left wandering, feeling lost and directionless but are still absolutely adamant that they must have a dream job and that answers will just come to them at some point.

More and more, I find myself contemplating why people (especially those my age) feel this way. We are constantly dissatisfied yet unable to locate the source of our dissatisfaction. I’ve tried reading articles, searching forums and social media threads for answers.

Why does picking a “dream job” seem like such an unattainable goal for some? How can one pick and pursue their ideal career? Is the pursuit of a dream job even something that a person needs to live a fulfilling life? Let’s try to unpack these questions one by one.

Why is it hard to pick a dream job?

The idea of a dream job is something that has been ingrained into the minds of every young person. “Find a job you love so that you’ll never have to work a day” is the common saying.

We are not only told to be productive and find work; we are expected to love the work we are doing. We are expected to make this job an integral part of our identity.

When we’re children, teachers don’t ask “what do you enjoy doing?” or “what sort of work would you see yourself doing in adulthood?” The question is always “what do you want to BE when you grow up?”

We are taught that what we do for a living defines us on a personal level. It determines our worth and value in society.

This reason, I believe, is why so many struggle with finding their “dream job.”

If my job is who I am, then I must immediately know what it is that I want. Or else who am I?”

The reality, however, is not as simple. Yes, there are people who have a clear path and know what they want to do and how to pursue what they want to do. But for many, it’s not as easy.

There are people who are directionless, perhaps, because they have many different interests and are a jack-of-all-trades; they find it hard to stick to just one path and excel in it. Instead, they try many things, which, to the untrained eye, may look like aimless wandering.

There are people who do have an idea about their skills and what they would like to do. But what they lack is a plan to get them there.

For traditional jobs like the medical field or corporate work or a law career, there are clear paths from A to B to C (for example, get your bachelor’s degree -> go to medical school -> internship -> residency -> doctor).

Non-traditional careers, like art or theater or even business, have no clear “roadmap” so those who want to pursue this are left doing a lot of guesswork and taking a lot of risks. They don’t know how to get from point A to point B because they don’t even know what point B is. Measuring your progress becomes a lot harder and, so, many feel frozen in place.

There are some who pursue a career that they’ve been told would bring them satisfaction. But when they follow that path, they find that it’s not what they really want but the idea of course-correcting or changing their life in any way makes them feel like a failure.

Why are we so hard on ourselves when we don’t immediately know and land that dream job?

I remember when I was in high school, we had a “career fair” but it wasn’t actually about showcasing any careers. All that happened was that various college and university representatives told us about what courses and programs they had to offer and how much the tuition would be. I reached out to my school principal and asked whether it was possible to also have career guidance seminars for those of us who aren’t sure yet. The principal dismissed my suggestion and just said “you should know already.”

I was about 14 or 15 years old at that time. Now that I’m in my 20s, I find it even more absurd to expect someone that age to already know what they want to do for the rest of their life.

And I think this is another problem with the “dream job” idea: that you’re expected to pursue it and stick to it for the rest of your life.

That’s a lot of pressure to put on an adolescent’s shoulders. “By now, you should know what you want to do. And you should have a clear plan to get there. And once you’re there, you stay there because that’s your dream.

Many carry this mindset even through adulthood. When, in reality, people change. Your interests change. Dreams change. The job market, economy, and environment also constantly change.

What you thought you wanted at age 15 is likely not going to be what you want at 30. But we live our lives believing that this is the case. That you can only have one dream job because this is an essential part of who you are.

Life, in reality, is a constant exploration. You’ll never really know what you want or what you’re good at unless you experience things first. And with more experience comes a little more clarity.

Instead, young people are frozen in a state of indecision because they feel that once they pursue a path, they can’t go back. They’re afraid of choosing “the wrong job” and regretting it.

So, how do we combat this? How do we take some of the anxiety and stress out of the pursuit of dream jobs?

I think we can start by reframing how we think of career paths. Choosing a path typically isn’t a straightforward road with a clear beginning, middle, and end. Rather, it is a long, extended “middle” with many twists and turns. Sometimes, life deals you an unexpected hand and you don’t end up in a job you thought you wanted. That doesn’t mean you’re stuck there forever or that your experience is meaningless. Every new experience is an opportunity for learning and growth.

One story that always comes to mind whenever I think of unusual careers is Steve Jobs. In a 2005 Stanford commencement speech, he shared that he audited a calligraphy class . He didn’t think it would be useful or would help further his career in any way. At the time, he was a college dropout and not really what people would see as someone with a clear vision or direction in life.

But if he hadn’t dropped out of college, he wouldn’t have stopped by that calligraphy class. And if he hadn’t been in that class, we wouldn’t have the different fonts and typefaces in our computers and laptops today.

Yes, that one calligraphy class became the inspiration for Apple’s typography.

When we’re looking back at our lives and reflecting on our journeys, it’s easier to see the connections, how each experience enriches the next. But connecting the dots while you’re going forward, while you’re still walking an unknown path, is impossible. So, be kind to yourself. Celebrate progress instead of expecting perfection right off the bat.

By reframing your mindset to one of learning and growth, you’ll find that you won’t feel as pressured to get it right immediately. And you’ll start enjoying the journey a little bit more.

How can you pick and pursue a career that actually suits you?

Now to the more complex part: How do you pursue your dream job?

Well, you must have a plan to get there.

How do you make a plan? You have to set goals based on what you want to achieve.

How do you know what you want to achieve? You have to first know yourself.

It may seem simple, but many people struggle with this. Knowing yourself–your true and authentic self–is a process, a continuous learning curve.

Human beings are complex. We don’t just want one thing; we want many different things. And often, our different wants and needs are in conflict with one another. This makes it hard to know what exactly to prioritize.

For example, a person may want to establish a business and become their own boss. But they also crave financial stability and security, which is not easily achievable when you’re first building your business. So, they can’t decide whether they should stay in their office job, where they are unsatisfied, or take a leap of faith and use their savings to start building their dream company, which could also possibly fail and bury them in debt. This situation may be further complicated by other wants, such as their desire to be respected and validated by their boss and co-workers. Or if they have people who depend on them to provide.

The point is: sometimes, there is no right or wrong answer. People are free to decide their fates, and this can sometimes feel overwhelming instead of freeing.

I fully admit that I’m no expert on finding dream jobs. However, I feel the desire to speak about this anyway because I think this is something that a lot of people struggle with and I want to at least help people gain clarity on their own little by little.

If you want to know yourself better, here are a few questions you can start asking yourself:

  1. What are your hobbies and interests? (You don’t have to be “passionate” about any of them. Just list down things you like, enjoy, or are curious about. This can help you narrow down specific fields.)
  2. What are your skills? And are you willing to pursue further training/education to meet your goals?
  3. What are your priorities in life? (Family, money, career development, growth, passion, stability, etc.? Try to list all of the items you can think of. And then try to rank them from most important to least important.)
  4. What are your values? And does your ideal work align with them?
  5. What was your favorite subject in school and why? (This can help steer you to possible career options)
  6. Which do you prefer doing most: problem-solving, creating, organizing, socializing, researching, or enterprising? (Rank these from most like you to least like you)
  7. Do you have any work/internship/volunteer experience? If so, what drew you to these experiences? What parts did you enjoy most? And what parts were you unsatisfied with? (Try to understand why in your mind.)
  8. Does your work dictate your lifestyle? Are there things you wish to change about it? (Do you prefer a flexible schedule or 9-5? Remote or onsite work? Work on weekends/holidays? etc.)

These are just some of the questions I can think of. They may not provide you with all the answers. But perhaps, they can give you a head start.

Once you know more about yourself, it’s easier to do research on potential jobs that may interest you. Or you could even forge your own path. Who knows?

This is only the first step, and the first step is often the hardest one to make. You can’t make plans when you don’t know what to plan for. So, knowing yourself (your wants, needs, strengths, weaknesses, skills, limits, etc.) is really the key. (Maybe I’ll make a separate article about the next steps–creating a roadmap for your career path and assessing what you need to achieve your goals–but let’s leave it here for now.)

Is a dream job necessary to live a fulfilling life?

If you had asked me this years or even months ago, I would’ve said yes, with absolute certainty. However, my view on this has really been changing. I don’t know if the pandemic is giving me tunnel vision or if I’m just starting to see the world more realistically.

I have asked many people who are older than me about whether they feel satisfied in their chosen careers. Many of their answers enlightened me. One person said that his job wasn’t what he wanted to do at all but he learned to enjoy it eventually. Another person said that finding satisfaction isn’t about being passionate about your job but about finding a job that you don’t hate and then pursue what you love (whether it can be monetized or not) in your free time.

Perhaps, the idea of a “dream job” is overrated. And that we’ve all hyped ourselves into believing that if we just find this one perfect career, we’ll be happy and satisfied.

The reality may just be that… our identity and self-worth doesn’t have to revolve around what we do for a living. That what we pursue professionally shouldn’t have to be the ultimate goal or achievement.

There is so much more to life than just work. Though, yes, having a job is necessary to survive (which means that it’s pretty important to find work that you tolerate at the very least), perhaps our real goal should be to find greater balance between our personal and professional lives.

To find something worth living for (whether this be our family, friends, favorite hobbies, travel, pets, or anything you can think of) and see our careers only as a way to fund the lifestyle we want.

The answer really depends on each individual. And I’m sure many will disagree with this sentiment.

If you find a job you’re passionate about, great! If your work isn’t what you would’ve wanted but is helping you pursue the things you love in your spare time, I’d say that’s also pretty great.

The key takeaway from this whole blog post is this: Don’t be so harsh on yourself when you don’t have all the answers yet. Life is about learning and growing. Try to enjoy the journey.