Lessons from an Aspiring Entrepreneur: It’s harder to not have a job, than to actually have a job.

It’s post-ZoukOut, on Monday. I’m sure all the half-hungover corporate-slave friends I have out there want to kill me for saying this right now but… I’ve come to the realization that it’s harder to NOT work, than actually working. Let me explain:

When you work, you have money. You wake up and go to work everyday (though you probably don’t want to), and you have routine and discipline. You have a support system of co-workers to interact with everyday (whether you like them or not), and you might meet your friends after work for dinner. You catch up with your family about what you did, and bitch about your bosses and theirs. At least, you have progress to talk about.

At the end of the day, you are tired, but you have purpose. (And money.)

Friends tell me that they admire my courage coming out of the corporate world to try and start my own thing. They tell me that they want to be like me. It sounds like the perfect plan – starting your own elusive business and joining the ranks of the New Rich (read Tim Ferriss’ blog for more context on the concept of New Rich).

Everyone wants to hear your success story, but no one really reads about or understands the failures that you go through first.

The reality is that I’m almost reaching the 6-month mark where I have been officially jobless, although most of it was spent exploring and working on some business ideas. In the interim, I’ve done lots of sleeping, reading, learning, meeting people, and gained more knowledge and advice than I could have ever hoped for. Sure, it’s an exciting chapter in my life. But friends and family question me, and at the end of this 6 months so far, what do I have to show for?


At least, there has been a bit of progress lately and things have just started moving forward. However, I’m frankly very disappointed in myself that it’s taken this long for things to get moving. I should have done what I’m doing now, in the beginning.

I sit at home most of the time stuck in my own head, only occasionally interrupted when my Granddad asks for help or when I hear my neighbours quarrelling about this and that. I feel like I’m lost in my own world, and no one understands.

I have all the time in the world now, but what am I doing with myself?

Dear God, are you there? Where are you?


7 thoughts on “Lessons from an Aspiring Entrepreneur: It’s harder to not have a job, than to actually have a job.

  1. It’s easy to say how you would do things differently if you knew what you know now. Never give up, you are richer if you have learnt from the lessons of the last 6 months.

  2. Hi Estelle,

    I am very surprised to read this post as I felt that you were writing the first half of my 2012, so I really understand what you’re going through. I spent more than six months doing nothing… or so I thought. But actually, looking back, I was really trying to figure myself out during all these time. Of course, I’m still guilty of being lazy and in the comfort zone and being a couch potato at home but, really, I was actually on a spiritual journey to discover myself.

    I can tell that you spend a lot of time and energy on self-development, I hope I’m not wrong. I think you would have pick up many things during your mini-retirement, intangible as they may be. I think when we suddenly have no job, we are caught off-guard with having too much time on our hands that we don’t know what we should do. I also asked myself that question: OMG I HAVE SO MUCH TIME IN THE WORLD BUT WHY AM I WASTING IT?! I felt so guilty. But now I know I spent the better part of my mini-retirement learning to enjoy doing the things I do without feeling guilty about it.


  3. I have worked for the Army since i was 19 and am probably thinking of coming out next years after 23 years…your above reflections are indeed refreshing and true. Well, just wanted to say well done, thanks and all the best in all your endearvous. Cheers.

  4. Stay strong little one. Get someone work with you to get the juices going. Even if you want to skype me I am in for that. Got to jet to work, reading this has made me late…oppppsss

  5. I never thought someone like me exists in the Asia-Pacific region. You know, people who want to create their own businesses but are currently jobless… It’s difficult because once you commit, you are going to commit till the end… unless we’re thinking about unsustainable businesses that we see a lot these days. Hang on Estelle. I myself am trying hard to face the social pressures of being jobless everyday -_-

  6. Sooooo true.. left corporate slavery after 20 years to start business and still looking for that elusive first client.s. Me.. a set routine helps where I try to push this Sisyphean rock up that hill. I also try to learn something new every day or how to do something better…. Share your pain and wish you luck and success.

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