How to leave a safe existence

Winnie Lim
The experimental years
6 min readDec 4, 2016

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The past year I had experienced a lot of anxiety, fear, shame and guilt while experimenting with my life. The lure of safety is very compelling while to walk away from the mainstream can be incredibly isolating. We live in such an utilitarian world of judgment, and even I have judged myself, much less others. But slowly I got better at reminding myself why I started doing this in the first place and why I should persist, though I am very much still a work-in-progress in trying to cajole myself away from safety:

I once thought I had the best job in the world, with the best life. Then I opened my own pandora’s box, as I plucked up the courage to uncover:

Strip away where I work, what I do, and what I have — and there is very little left, I have recently discovered. Who am I, without the layers I have put upon myself based on societal expectations, even without the ones people have consciously tried to put upon me…I had allowed my career to define me. It was my career, that determined whether I was worth a place in society, whether I was accomplished, whether I could even start being proud of myself.
Who am I?

It took me another year and change to make the leap to let go of my old self that I have so painstakingly built, in order to really seek to understand who I truly am. Another year later, I have barely begun to scratch the surface.

I have the tendency to project the future. I often use it to project the moment on my death bed, in order to minimize regret. Jeff Bezos, the founder of Amazon famously termed it the Regret Minimization Framework:

“So, I wanted to project myself forward to age 80 and say, “Okay, now I’m looking back on my life. I want to have minimized the number of regrets I have.” I knew that when I was 80 I was not going to regret having tried this.”

I tried to imagine what would life be like if I lived my life on the trajectory I was in, and there were a few best-case scenarios:

  • I become really successful at my job, helping to build and design something millions of people will use
  • I hop from job to job, hopefully I’ll learn something at every one of them
  • I start my own startup
  • I join a non-profit so I can collaborate with like-minded people on a cause
  • I have a successful exit, which therefore I spend the rest of my life doing what I want which may include distributing the capital I’ve earned

Imagine my horror when I realised none of those scenarios would make me come alive, or to be glad that I have lived, that my existence was worth its while. Any of them coming to fruition would have made a decent life, if not extraordinary, on most people’s terms.

That’s the man who never followed his bliss. You may have a success in life, but then just think of it — what kind of life was it? What good was it — you’ve never done the thing you wanted to do in all your life.
Joseph Campbell, The Power of Myth

But I am not most people. Most of the time I feel life is a non-cancellable expensive paid subscription that I didn’t know I want in the first place. What would make life in itself worth living? What is my bliss?

I don’t want to live an entire existence without even trying to know the answers.

Had I not made the leap, I would most likely be on a declining trajectory, because I was gradually getting more disenchanted with life. I may have still stayed alive, but I might as well not exist. Even if I had managed to delude myself that everything was fine, I would be on the trajectory of a safe linear existence.

Why do we live

…a question I ask myself each time I try to wrestle myself from the clutches of safety. Is the sole purpose of my existence just to get through all the responsibilities, obligations, debt of my life and get to my deathbed unscathed? Is it to leave a legacy, something that so many high-achieving people are obsessed with? Is it just not to break people’s hearts?

Do I resign myself to keeping myself alive just for others to live? What is it then, the story I can live for? What is the point of my life?

…f we are ever to give any gift to the world, it will have to come out of our own experience and fulfillment of our own potentialities, not someone else’s. — Joseph Campbell, The Power of Myth

I know as long as I do not have a good enough idea of who I am — why I must exist, I will always struggle to have the will to live, much less contribute meaningfully. I know deep within me my existence as it was, was not sustainable.

I don’t have any answers, but I am willing to search. I have glimpses, and I know what I do not want. I do not wish to lead a safe, linear existence. I don’t want to wish death upon myself all the time. I want to give life a real good shot, the best I could muster. I want to extend the edges of myself, to continually expand the way I view the world and my self in relation to it, in order to determine at the end, is life truly worth living for itself?

high variability extends the edges

I have lived an existence where it was defined by other people. Even the risks I took and the unconventional paths I walked on were modelled for by people before me. What about breaking of conventions that are less popular? Can I find my bliss — as Joseph Campbell has spoken of — by being a nobody, in a society that is obsessed with making somebodies?

Can I muster the courage to do something that would fill my heart with joy and pulsate with aliveness, even if no one else understands it?

I still don’t know what would make me determine life is worth living at my death bed. But I do have glimpses, and these glimpses are like faint guiding lights in a sphere of darkness.

At the very least, I want richness, width and depth. The past year, I have been learning to look at my life as a piece of fabric. I do not wish to be an expensive, coveted piece of silk or cashmere, but rather a weathered, multi-textured pieced-together patchwork.

Diversity and flexibility are bred out in exchange for maximizing certain variables that suit our purpose. But if conditions change, the species is locked into a narrow range of variety. Monoculture leads invariably to a loss of options, which leads to instability. — Stephen Nachmanovitch, Free Play

I just have to keep on being brave enough to let the colors in.

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