Small Actions; Big Learnings

On Christmas eve last year, I had 14 other spontaneous friends who tagged along with me to do an outreach for the homeless in a few locations of Singapore.

25 December 2020

It all started with a sprint of inspiration from a book and simple poll on my Instagram Profile asking my friends and acquaintances if anyone would be keen to help out in a project for a group of homeless (otherwise known as rough sleepers). There, I have many who have reached out and got started on planning this project since.

In doing this project, I’m truly heartened to see many of my friends and peers stepping up to help in their own ways; Some reposted about the project to share with their friends on their own accord, some came up with community mapping questions without anyone telling them to do so. And a lot of these actions require initiatives and self-directedness, which warms the clams of my heart seeing these many people wanting to do good for the vulnerable.

I’ve also realised that many people want to do good, but it’s always the question on where and how can one start? As a strong social change agent, I aim to experiment possibilities myself as an inspiration for others to take action in addressing the things that matter.

Project Givelah! is an initiative to give our homeless folks some blessings during the festive season to start 2021. With a care pack distribution as an entry point to start conversations, we wanted to find out more about the items that they might need while sleeping outside, instead of jumping into assumptions that they might need certain things which they don’t.

Watch this animation by Our GrandFather Stories to learn more =)

The Planning Process

During the initial stages of the project, many I knew always asked, “Do you want to collaborate with ABC Organization? Have you reached out to XYZ Organization?” While I could see their kind intentions to leverage on professional expertise, I personally am not keen to work with big organizations for a start.

It’s the idea about doing it yourself, and learning through doing it yourself.

In my opinion, I believe that there’s a lot of potential in a person to be part of a social change — that while volunteerism is strongly encouraged, more could be done than just monetary efforts.

For instance, if a group of our young individuals have the skill of making videos, would they be able to create content to raise awareness and be advocates for the issue? Likewise, if a particular someone has the capability to drive, would he/she be able to provide transport for actions to take place? Or, if a group of design students are passionate about bettering the lives of a certain disadvantaged group of people, would they be able to design a product or service with their acquired knowledge from school?

I see these skill-based volunteerism opportunities more valuable than just “donating a portion of my allowance for someone”, because money doesn’t necessarily solves everything. Sure, that it might just be the solution for that many possible outcomes, but sometimes what the vulnerable groups need, is more than just money. Perhaps they need a job, or a service where they can seek long-term help from. And I shall elaborate on my opinions about relooking volunteerism in the following medium articles.

For now, let me bring you through some key points and takeaways from the team.

Key Learnings

A wise lecturer once reminded us that:


Having to juggle my other commitments in life and this project at the same time is … quite tortuous. But when I’m reminded of the reasons why I even started this project in the first place, my fuel of eagerness came back to me right away. Similarly, I suppose this could be what most sole founders of organizations would have felt in their experience — that leadership is a lonely journey but it takes one person to start something for the rest to follow.

I wouldn’t say that I’m the best leader in carrying out this project, in fact there were many things that could be improved upon. I would also like to take this opportunity to thank the team and people involved, especially Mr. Liu for pushing me and getting the project started.

Insights Into The Issue

I recently chanced upon this video by TheSmartLocal where people share their experiences and reasons why they moved out from their Parent’s Home.

Interestingly I somehow connected the dots, and thought that maybe these are some of the possible reasons why people choose to be homeless by choice — that they require a space of their own, or an alternative that reduces family conflicts. And I wonder if the other 59,000 viewers thought about this too.

Don’t you think so?

When I sought some expert insights from people who have been interacting with the homeless, they said that another reason could also be that they want to be money-saving and don’t want to commit to renting a shelter.

During the outreach, although I personally didn’t manage to get any first-hand interaction with the rough sleepers, I realised that it requires some form of skill and experience to identify them. Together with the friends whom I was with, could only be sure that a person was homeless if we caught them already sleeping on benches or on the floor. I’m sure none of them wants to be spotted either — which makes the outreach process a little harder for us.

If anything, my biggest takeaway in this entire experience was to understand that people each have their own stories worth respecting and listening to. Even for the people who have offered to help in this project, that we have our own lives and commitments outside. And every reason we hear from people is worth acknowledging.

Individual’s Reflection


“Frankly, my initial perception of homeless people are just people who do not have homes and jobs, mostly beggars. Until the guest lecture in year 1 that really opened up a whole new world to me and got me interested in this community, because it seems like there’s so much stories each individual might have which draws me. I love hearing people’s stories or some people might call it kpo but I believe in listening with a heart.”

“That night, tbvh I was not prepared nor did not know what to expect because we came grabbed down from our meeting which was mentally tiring. To make it worse, at our first location, in one of the parks we visited, we failed to find any. It really dampened my mood at first, but as we walked further into the park, we discovered more lights and life. I was surprised given that it was past 11, during a pandemic. Personally, I would have left the place immediately, much less someone who is homeless and finding a comfortable spot to rest.”

Then, the word privilege and selfishness struck me. I don’t remember parks being that bright at night. “is it for safety purposes?” “is it because people complained that it was too dark for them to do anything at night?” these thoughts went through my head. For many of us, we have a shelter to return to after all our activities. But for the homeless, these parks might just be their shelter.

Then at our 2nd location, we finally located some homeless people. But when we met the first one. I was scared. I did not know how to approach. I felt anxious and worried. But why? What was I afraid of? That he would misunderstand and harm us? That he would feel we’re pitying him which some people may not like? In all honesty, I would say both. I’m guilty that I still have that bias or impression that they may be violent because of their lifestyle, to protect themselves from others. And on another hand, I was worried how he might think of our act. Will we upset his feelings and ruin his night? People do not like being pitied.

Then we distributed out the packs to other homeless people we saw, who were all already sleeping except for one “questionable” uncle. Not in the sense that he is suspicious, but that our conversation with him left me with many questions. He claimed that he lives nearby, but since his bicycle is parked here, he wants to watch it so that no one tries to open and steal the items in the storage behind the bicycle. While he claims so, I saw cardboards, personal belongings, some daily necessities and medication (if i did not see wrongly) which made me wonder if he really goes home after 4am or if he just lives there. If he has a home, why did he not just leave his things home? or why did he not park his bicycle near home? I had so many questions but did not pursue because the uncle spoke quite loud and there was another uncle behind sleeping. When we offered the gift pack to the uncle, he told us the milo and oreo was enough. the rest can give to others. That just reminded me of the entire theory of “many times, we’re giving based on what we think they need. Not what they really need.” kinda reaffirmed my belief and passion listening and genuinely understanding another person’s story.

After the whole thing ended, we found homeless people and gave out the gift packs. But then I realised, they were all males. Yea, it is easier for males since they can just sleep anywhere in public. but what about females? Who may be more vulnerable? Not to be sexist nor look down on females but they face more danger than males, especially in the night. where could they possibly be living then?

Hui Tian

“Similar to Xavier, having encountered the uncle with his bicycle who only requested for the milo and oreos, makes me want to do more of such outreach. It made me think about their needs, that maybe what they want are just food to go through their days as compared to bulky items. In the future, I want to invite my friends to interact more with the homeless together. This experience allowed me to see the issue with my own eyes, the situation that the people are in that I often neglect in my everyday life.”

I plan to walk around the places where the homeless will usually be at to befriend them and learn more about this community. I also plan to bring some food along such as milo and biscuits to distribute. Through the conversations, if there is anything that I am able to help, I would want to lend them a helping hand if circumstances allow!

Wei Liang

But I get the sensing most are homeless not by choice (even if they do have a house but can’t return) and there seems to be a gap in the system whereby people are waiting for rental house approval but meanwhile they have no house to stay so perhaps something could be done about this.


I felt slightly disheartened when we didn’t manage to find any of the homeless in the beginning. I wasn’t expecting the crowd at the location we were at, and I realised that there are quite a lot of groups out there offering help/support to the homeless community as we saw other gift packs given to them. We had quite a number of good conversations with the various individuals and through our conversations, we realised there are generally 2 types of homeless group. Firstly, those waiting to get a place and secondly, those who rather be alone and don’t want to rely on the government. With that being said, the number of homeless individuals can be only reduced/supported immediately for the first group of individuals as for group two, it will be difficult to change the group’s mind at the current state.

While chatting with the homeless, we realised it was quite hard to start the conversation to ask if they were homeless, but somehow figured out a way to do so without sounding offensive or assumptious. Some individuals were very open to speak to us while some find it hard to trust us. Most of the homeless who don’t want to rely on the government are generally not looking for any form of help, as though they have given up and only trust themselves. The main issues we learnt for the homeless would be their cleanliness (e.g showers, washing clothes and etc) and daily food.


On the distribution day, I have spoken to a few of the rough sleepers and I was shocked that in Singapore where we pride ourselves to be a country with full home ownership and HDB as an asset, there are still people who do not have a roof over their head. From the stories, I have heard stories about family conflict and how some are waiting for the keys to their rental flat. Through one of the sharing, I heard how this uncle have strain family relationship which leads to him needing to live separately, how he is adversely impacted by his health condition which impede his ability to work, how he have been rough sleeping for quite some time and yet he still remain positive and grateful for the small things that come along his way such as receiving whatsapp messages of well wishes from his friends. He also pointed us to places where we could find more rough sleepers so we could also share our care packages with the rest.

Another story was how one of the uncles rough sleep due to family conflict and he shared many tips and item suggestions that rough sleepers may need. Uncle shared that he is a salesman and takes pride in being a salesman for many years. Through this experience, I was surprised at how willing the rough sleepers are in sharing their stories with us which have so much for us to learn from.

Moving Forward: Part 2 of Project Givelah!

After raising funds to prepare care packs for 20 rough sleepers we’ve came across with, we’re now moving towards the second segment of the project — Donation Drive


Even as I’m writing this article now, I could hear the driving rain through my windows. And I wonder in nights like these, where would our rough sleepers go and seek shelter? Especially in this monsoon season, items like blankets and jackets are much needed!

Do drop me an email at or message via Telegram/Instagram @annat2m if you have any questions! For transparency and accountability check, if you could donate any of the items above, please add a new note in the yellow column on this padlet!

Thank you for taking time to read up on this article. We hope that some our learnings have given you some insights into the issue, if you’d like to be part of this second segment of the project with us, feel free to contact me! I’m happy to share more =)




Writing stories that matter.

Love podcasts or audiobooks? Learn on the go with our new app.

Recommended from Medium

Our four favorite Help Scout features

Office Design Renovation As Companies Rethink Office Life Post Lockdown

How we doubled Canva’s engineering growth rate in 6 months

Digital Exhaustion

Lookback at the Problems of Transport Industry 20 Years Before

Positive Reflection

The Socially Conscious Triad

Measuring the Moments of Kambr

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Anna T2M

Anna T2M

Writing stories that matter.

More from Medium

2 Tips for a More Fulfilling Career

List of 19 Influential Black Leaders in Tech

Graphic of profile images of influential black leaders in tech.

5 Principles of Sponsorship Evaluation

5 Steps in Making My Goals Happen