Freedom does not come free

real talk on experimenting with my life

Winnie Lim
The experimental years
6 min readNov 25, 2015


It took multiple attempts to write the original piece and I deliberately left out a lot of context to keep it simple, in the hope I can fill them in with separate posts later. Someone raised some valid questions in the response above, and I want to take the opportunity to answer them. TLDR: I am not rolling in a secret stash of cash.

Freedom does not come free.

On financial constraints

I do not have financial constraints for now, and that is by conscious design. I do not have any assets and hence no debt: no property, no car — to some people this is considered to be freeing, but as a Singaporean I can assure you that I am still filled with the same insecurities each time I see my peers accumulating assets. Philosophically I think security is illusory, but I am still a human being first and foremost, and like a lot of people, I do like having things and feeling secure.

I lived a relatively monastic life, as a massive introvert I do not go out often enough for me to spend too much money. All-in, it was enough to save a small sum of money over the course of three years I lived in the United States that is now my runway for this year of experimentation.

That small sum of money is all I have. I have no deeper pockets to reach into, I would rather live on the streets than to depend on anyone including my family. I will have nothing after this experiment, but I will have something priceless in return. It doesn’t make the lack of financial security any easier.

On dependents

I do not have any dependents, or even emotional co-dependents, and that is also by conscious choice. The only exception for now are my parents, whom I have to disappoint and worry each time I make a ridiculous decision like this. Like any aspiring-to-be-as-filial-as-possible-Singaporean child I would like to have the financial capacity to gift them a holiday or tell them they don’t have to worry for the rest of their lives, but right now, I am not sure I am even in the position to tell them not to worry about me. They do not depend on my financial support, only because they have traded off precious years of their youth and family time (with me) in order to have some economic independence today. I am very grateful for that, but there is some part of me who would perhaps trade that off for more time and presence with them when I was younger.

I had also consciously chosen to be emotionally free — staying single, no dogs, not even plants — so I can make decisions like this without impacting any entity I love.

The price that comes with having nobody depend on me is having nobody I can depend on. I am alone.

On privilege

I am massively privileged now, I will not lie. Even taking the financial ability to make this experiment aside, I am also privileged by the lottery of my birth. That I was born in a country that afforded me an education, safety and that I can have economic opportunities as a female. I was born to middle-class parents. I never had to starve. That is precisely why I want to do this now. I want to maximize the privilege that was given to me, not squander it. Just like startups using their capital for experiments in order to find their best shot of success, I want to leverage on my privilege in order to find the means to efficiently distribute it later.

I had the privilege of working in San Francisco that gave me some disposable income to even be capable of saving some money in the first place, but that was a result of an accumulation of similar risks I had taken over the course of more than two decades. That is another story to tell.

Sometimes having privilege makes it harder to attempt to take risks, because it is scary to lose that privilege, especially if we have worked really hard for it.I took more risks when I was younger and had less, because there was less at stake for me to lose.

On what I let go

It was very hard for me to give up the life I had built in the San Francisco in order to do this. It was the city that made me feel I belonged somewhere. I had to let down people who nurtured me to be capable of making this leap in the first place. Till today I still miss it, I miss the people. But life is always about making tradeoffs. I want to be a person capable of letting go of what was precious to me to do what is right.

It took an entire year to get the legal paperwork done for me to work in the US. I gave up a green card in progress. It would be an economically comfortable life for me if I continued on my previous trajectory, especially considering the effort I had to put in to even get there.

Nobody would question the life I had. Nobody would question my value to society. I was a designer working in a startup at the heart of it all, San Francisco, living in a rent-controlled apartment in one of the best neighborhoods there. On paper, I had everything I could possibly have.

But that still didn’t buy me the love I didn’t have for myself.

What do I plan to accomplish

On the surface, nothing. I just want to be, and that is the whole point of the experiment. Take away what I had, who is the human being I am?

Being — just having the space to be the person I am and do the things I would naturally do if I didn’t have external pressure like deadlines, expectations, conflicts.

How do I plan to get around that

Just being. I am not being flippant. Modern society has taught us that we need to plan, to measure, to prove ourselves with metrics, have a long list of accomplishments. There must be a strategy for everything.

I lived that life, it didn’t work out for me. It made me consistently burn out, depressed, suicidal, never feeling I was enough. I seemed to have everything, but it made me resent myself and the world more.

Is this selfish?

Maybe. At the end, it all comes back to my basic philosophical belief that we cannot give our best to the world if we cannot be at our best.

I want to spend the rest of my life giving my best to the world without feeling like I am about to collapse in exhaustion any given minute. And that will keep happening until I learn to see myself. I also have no idea what is actually “my best” without the standard measurements given by society, so I want to take this time to explore that.

Will I really learn to see myself with “just being”?

I don’t know. Hence it is a experiment. But knowing I had the courage to let go of everything I had worked so hard for — including stability, safety and security — is enough of a first step to get a glimpse of the self-love and respect I never really had and can possibly have.

If I said I was taking a year to study, nobody would bat an eyelid or think this is an exceptional thing to do. We pride too much on external learning and accomplishments, without realizing that perhaps what comes internally makes the fundamental building blocks to our lives. Without them, we are like a house of cards. The job we have may cease to exist, the formal education may cease to be relevant, money may disappear in an economic bubble, but self love and respect cannot be taken from us.



Winnie Lim
The experimental years