My Self-Employed Journey – Part 1: Why and How I Become Self-Employed

Growing up, I didn’t know what I want to be. I went through the same motion that everyone goes through: go to school, go to poly/uni, find a job. I enjoyed my time in school, however, I didn’t exactly enjoy my working life.

When I was in my first job, I figured, maybe I didn’t enjoy working because I didn’t like my role, so I changed job. Well, after changing to my second job where I held a different role, I still didn’t like what I do.

I love the friendships that I made with my colleagues and bosses, don’t get me wrong, but I just didn’t find any meaning or purpose in what I do. I didn’t feel that I contributed anything to the world. I felt that I was just merely wasting my time on earth.

Up to that time, I knew I didn’t like my industry. But I still didn’t know what I like. As a millennial, I grew up believing that we have to find our passion to live a meaningful life (which I now know is not entirely true, but that was my belief at that time). I lived my life by Steve Job’s commencement speech at Stanford.

So, I set out to find my passion.


My Soul Searching

My soul searching process involved a lot reading self-help books, listening to Steve Job’s speech over and over again, staring out of the window on several long bus journeys, scribbling on napkins at Starbucks brainstorming what life could look like if not like this, traveling solo to foreign countries that I’ve never visited before to force myself to get out of the comfort zone, et cetera. I did all of these soul-searching while still holding a job.

Here are my realizations after soul-searching.

There are 3 important things that matter in my life: consistent passive income, travel the world, and physical activities.

To my young, restless self, the answer seemed to be either working a sales job with high commission or starting a business.

I was young and didn’t have any dependent, and I was lucky I didn’t have to support my parents or siblings, so I felt that it was the best time to take risk.


My first foray into self-employment was being a real estate agent. I naively thought that real estate agent can earn 10-50k a month with just a few hours of work (each viewings are just a few minutes long, right?).

After closing several room rental deals over 3 months, I realized it was a highly stressful job and I didn’t have enough passion for the job to ride through the stressful times. And worse, I didn’t have the required skill to be a successful agent, namely speaking skill, negotiation skill, confidence, etc. So I quit.

Next, I created an e-commerce site to import food into Singapore, but I abandoned it after realizing that import licensing was a complex thing that I didn’t want to get myself into. I also started an F&B stall, which I abandoned after 2 weeks because of the lack of patrons, and I lost S$4k (rent deposit, gas deposit, purchase of ingredients and materials) from this failed venture.

I learned soap-making and wanted to start selling homemade artisan soaps. I learned jewellery-making and started selling a couple of pieces. I got my hands on some superfood and created an e-commerce store to sell it. These start-up businesses didn’t last.

After failing multiple businesses, I learned an important lesson or two.

First, I failed because I was doing things that didn’t matter to me. Soap, jewellery, superfood, cooking, closing deals didn’t matter to me.

Second, I’m glad I tried early and failed early. That way, I learned what I liked and what I disliked early, and I can move on sooner. I won’t know I dislike something until I try it.


The One That Matters

I love writing. I’ve been writing blogs for fun since I was in secondary school. I continued writing through university and my readers were mainly my uni friends.

When I started working, I shut down my blogs because I didn’t want my colleagues and bosses to know my personal life (or rather, my past life).

In between those failed ventures I mentioned above, I started writing again. I started a new website and wrote about things that matter to me.

As time goes by, I found my ikigai through this work. I found the intersection of what I love, what I’m good at, what the world needs, and what I can be paid for.

Of course, the journey from finding the ikigai to ensuring the ikigai becomes sustainable takes time. For me, it took 7 years. (Thank God it’s less than a decade!)

2022 was the year I took the leap of faith to become a self-employed person to work full-time on my ikigai. After being self-employed for a full 1-year, I decided it’s time to share my journey here.


I won’t reveal what my ikigai website is, because that’s not the purpose of this article. I’m not writing this article to brag or to sell you a course on how to run a successful website.

Instead, I’m sharing my journey to be a self-employed person because I want to help people who are at the crossroads but not sure whether starting a business is the right path, people who want to start their own small business but don’t have the conviction to do so.

Another reason is because I don’t see many people sharing their small-business entrepreneurship journey in Singapore, so I wish I can give some insights based on my own experience.

And nope, PrudentDreamer is not the ikigai. PD is just my creative outlet in the personal finance space. If it ends up being an ikigai for me, that’s a bonus.



Back to the question in the title, why did I decide to be self-employed? To be honest, it’s still a question I struggle to answer. I can’t pinpoint a specific reason. All I know is, I want to do a meaningful work and I want the freedom to work when & where I want to. This doesn’t mean that running a business is all rainbows and unicorns, I’ll share the pros & cons in future articles.

And how did I become self-employed? By brainstorming a list of things that I might enjoy doing, trying out various business ideas from the list, working on the one that gives me ikigai on the side while working full-time, and finally taking the leap when my gut told me to.

I’ll be sharing the pros & cons of being self employed, what to prepare before jumping the ship, how I budget for inconsistent income, etc, in future posts. If you have any questions regarding self-employment, let me know in the comments!

If you find this post helpful, feel free to buy me a coffee :)

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