How to Discover What Your Dream Might Be

How to Discover What Your Dream Might Be

If you’ve followed my writing and work for some time now, you may have come across this question (or similar variations):

If time, money and energy didn’t matter, what’s one thing that you must do in your life such that when you look back at the end of it, you can say that it was well-lived?

Basically, this is my expanded version of “What’s your dream?”

This question commonly leads to two kinds of scenarios.

1. If you’re a big dreamer like me, and have taken some steps to try out some of your dreams, you may find it difficult to narrow down and focus on which dream is most important for you right now.


2. You’ve lived your life according to what everyone else seems to be doing, and while you may have an idea of what you’d really like to do when you retire, the concept of “my dream” sounds completely foreign to you.

Or it typically appears along the lines of wanting to have more money (which is still linked to your survival, not so much a dream), to travel (perhaps just to get away from your job), or to find love (which is common for many single people because we think that by a certain age we’re supposed to be married and pop out babies).

Either way, both scenarios presents a similar issue: when you have no clarity about your dream, you don’t know where to even begin to take action towards crafting a worthy and meaningful purpose for you.

So today I decided to share my two cents worth on how to discover what your dream might be.

From what I’ve learnt along this journey so far, our dream is something intricately tied to the core of who we are, which is essentially who we’ve always been, ever since we were born.

If you’ve observed young children before, each one behaves in different ways, and they are not embarrassed or afraid to express who they are. Some are noisy, active, extraverted and curious. Some are quiet, mellow and prefer to play alone.

And when you ask children what they want to be when they grow up, they’re often sure and excited about their answer, even if it changes from time to time.

Well, we were all like this once, we were once excited about and connected to our dreams, and we used to actively imagine what our lives would be like when we grow up.

Then as we get older, we enter into a world where expectations, rules and responsibilities are placed upon us, and we’re slowly conditioned by well-meaning adults (who often don’t know better), to give up the silly whims of childhood (including our dreams and imagination), and to enter the real world.

We’re told to study hard, get good grades, get into a reputable degree program, get a high paying stable job, find a compatible partner, and so on… and amidst the struggle for survival in our current physical reality (which is a legit thing we all have to prepare for), we adopt the ways of the society and culture which surrounds us, and we slowly lose sight of what truly matters to us.

We toe the line, we stop questioning things, we accept the status quo, and we accept that life is supposed to be the way everyone says it is, and what everyone else seems to be doing. And anything that strays too far from that is not acceptable. Or we view such people as “daring”, “unconventional”, “different”, and secretly wish we could be more like them, when really, we have the freedom to choose that kind of life too, if only we didn’t stop ourselves.

This happens to us all at some point in our journey, and whether you’ve lived a conventional life or bounced around from dream to dream trying to figure out which one is “right” for you, we are so disconnected from who we truly are and what truly resonates with us, that we don’t even notice the clues about our dream that have already shown up in our lives.

It took me a very long time to start paying attention to these signs, but once I realised they’ve constantly been appearing, I looked back on my journey so far and started to see they have always been there.

When something is worthwhile and meaningful as a purpose for you, as a dream for you to pursue, it would have already appeared in your life in different forms, usually as incidents we write off as “random” because we don’t see where they fit in the grander scheme of our lives.

But as we get older, the benefit of hindsight increases, and we’d have more instances to look back on to pinpoint how this dream has constantly been trying to show itself in our life, if only we had given it more attention and time.

The Many Signs of My Artist Dream

I was 28 when I rediscovered my childhood artist dream and realised this was it all along for me. At the time I was in my final semester of my BA in Songwriting and Music Business, and I had enrolled in several classes outside of my major because I realised my ten-year-long dream of being a professional singer-songwriter had never really been right for me.

One of these classes was “Introduction to Drawing”. In the middle of the second drawing assignment, I had been drawing for hours in the studio on campus when I suddenly had a flashback of a memory when I was 8 years old, drawing at the dining table after I finished my homework. I remembered being asked what I wanted to be when I grew up, and I said I just wanted to draw. That was when I learnt that “artist” is the name of the profession of someone who draws.

I was excited about this… and then I was told that artists don’t make money and I should do something else instead. Because of what I was told, I started to feel like it was “wrong” for me to be drawing, so I stopped (outside of what was necessary for school assignments), and I completely forgot about my artist dream ever since.

When I had that flashback, I found myself questioning if being an artist was my purpose all along, which led to further reflection upon my life, and slowly, many seemingly random events came back to me.

Just the previous semester, I had enrolled in a creativity class, where the teacher had asked us to take up a creative project for that seamster which wasn’t something we’d normally do. At first I had wanted to do a painting on canvas, but when he asked if I had experience in it and I said no, I went with my second choice instead (which was to write a short story).

A few months before that, I was assisting at a Catholic students retreat, where the team had a few minutes to draw a poster to represent us. I ended up drawing most of the elements in it, and everyone was so amazed by my abilities. I was rather surprised by this, because to me, those drawings were not really refined and I knew I could draw better if we had more time. Plus I thought then that everyone was able to draw like I could, so I never thought anything special about my artistic abilities.

In my first undergraduate program as a Psychology major in Singapore, while I was having second thoughts about pursuing a career in psychology, I remember making a few trips to the local Borders bookstore, trying to find answers to my direction in life in the Christianity (I was a devout Catholic back then) and self-help aisles. On one of these trips, I somehow wandered into the art section, and spent hours poring through book after book on the master artists. Around that time, I also wrote a paper about emotions and art in Salvador Dalí’s work for one of my psychology classes.

Going back to earlier than that, in high school I was always doodling in my school textbooks while bored in class, and whenever there was a chance for artistic expression in our assignments, I’d always embrace it and go all out, even when it wasn’t compulsory or graded. One year, I sat next to the best artist in class, who was always drawing cute cartoon animals in her textbooks, and I started to draw cute animals too.

I also recalled trying to take up painting as a hobby in my teens, though I ended up getting too busy with schoolwork to keep that going consistently.

And when I was 12, in my final year in elementary school, I had somehow joined my school’s arts and crafts club. To this day I haven’t been able to recall why I had joined, but I remember when I was there, I enjoyed it so much that I wished I had joined a couple of years earlier.

There were more of such random instances which I haven’t shared here, but I believe it’s enough of an example to show you the ways in which your dream has probably already appeared in your life in some way, big and small, and all the signs you need to figure out your worthy and meaningful purpose have always been with you.

It’s just a matter of whether you’ve noticed them or not, which is a process that gets easier with the benefit of hindsight and experience.

Interestingly, even after I got that flashback to my childhood dream in that “Introduction to Drawing” class, more signs came my way.

For one, the professor mistook me for an art major based on the quality of my assignments, and then told me at the end of the semester, “I can’t believe you’re graduating as a songwriter. But it’s okay, I believe you’ll do art someday, and one day I’ll walk into a gallery and see your name on a painting.”

Secondly, when I paid a visit to my college’s career counsellor, I did the Myers-Briggs Perosnality Test and a career test, and both test results indicated that my top career is “artist”.

Thus in the same way for you, the signs that point you in the direction of dream will continue to appear in various forms — your childhood ambition, a hobby, having friends with that same interest, getting positive feedback in a skillset you didn’t even know you had, career tests, personality tests, aptitude tests, and so on…

And when you’re able to notice and pinpoint these memories and instances in your life, you’ll then have more certainty that there’s something here worth exploring, which could be your dream and a worthy and meaningful purpose for you.

It’s not usually an in-your-face kind of answer, but at least it will give you just enough clarity to get started on the journey to see if it’s the right path for you.

“Sky Painters” (2013), Acrylic and mixed media on canvas, 12 x 12 in. SOLD.