Lacking Ambition… Maybe Not?

This is going to be quite an emotional post, which is rather out of the ordinary and perhaps not that befitting of this blog? But well, documenting this piece of reflection just felt damn necessary on this Saturday morning. I really had to get this out of both my chest and mind. And nothing beats writing it out if this was to be done in a clear and coherent way.

Even though it’s the June school holidays and I have been “enjoying” the past couple of weeks off from work, I have actually been in a funk for the best part of this period.Yes, I know how ungrateful I am. By immersing myself from one game to another but not really enjoying them at all, I am probably insulting everybody who’s yearning for a good break.

But the fact was that something was eating at me constantly from the inside, but I made all attempts to avoid addressing it, perhaps till a couple of days ago.



A few weeks ago, we caught up with some of our JC classmates over dinner. Since the Mrs was taking a sabbatical and I had just made a career change, our lives inadvertently became “the topic”.

And quite naturally, during the conversation, we subtly explained our positions with regards to personal finances, semi-retirement and my potential career as a self-employed tutor in the long-run.

The topic moved on and everyone shared some updates about themselves. Interestingly, when Mrs 15HWW suggested to one of them who’s practicing medicine to downshift and become a GP, we heard a no-no reply. 

Because, that would be LACKING AMBITION.


Call me perceptive (or too sensitive), but the sense was that what both of us were doing smacks of a lack of ambition to them. And somehow, I was concerned, not just because they are some of my dearest friends, but because they might be right.

And it isn’t about downshifting and limiting my material desires. I still stand by that.

Instead, I am probably lacking ambition with what I want to do in my life. I.e, selling myself short. I have coasting along in life for the past 4-5 years, choosing some of the safest routes to get to financial independence and navigating through small hurdles. Things are getting a little too predictable, a tad dull.

With pre-conceived assumptions, I was actively limiting my boundaries with my choices. And subconsciously, I might have known it all along.

With more time, I understand myself better and better. What I can and can’t do. What I should and shouldn’t do. On hindsight, during the past week, I was probably just trying to escape from REALITY, and avoid making a HARD DECISION. 

I might lack professional ambitions, but definitely not life ambitions, even though I might have lacked guts to attempt to realise them.

But not from this moment. Onwards, Mr 15HWW!

The most straightforward path might not be so suitable after all. 


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38 thoughts on “Lacking Ambition… Maybe Not?

  1. Andreas G. Schmidt

    What you describe occurs quite often and shows me that your classmates do have a very narrow perspective on life.
    Everybody has to define for themselves what success and what ‘enough’ means for them. And then have to grow a thick skin, listen to what others have to say and then decide whether it fits to our definition of success, values and ‘enough’ or not.
    Reading through your blog I think you are very ambitious with very clear goals. Something many ‘ambitious’ people totally lack, because they do not know when it is ‘enough’

    1. My 15 HWW Post author

      Hi Andreas,

      Actually, I wouldn’t say that their perspectives are narrow. They are a lot that can understand the math behind early retirement, just that they might find my prescribed lifestyle a bit “less interesting”.

      But you are right that many in this world do not know when it is “enough”.

      When I wrote this post, actually I was thinking along the tacomob line. You’ve got a great blog running and will be taking some time to read through your articles.

      Once again, thanks for popping by and of course, the sincere encouragements!

  2. B

    Hi 15hww

    Sometime in the past i’ve written a post on being “unambitious” for financial independence wannabees which i think resonates in your post.

    The thought of having just enough for everything makes one looks unambitious but i would argue that only truly by knowing ourselves we are able to derive the conclusion. At this time, i think we are all somewhat trying to find out more about ourselves so dont feel too bad about making some changes to what you feel are required to be changed.

    1. My 15 HWW Post author

      Hi B,

      At our age, nothing’s really fixed and cast in stone. There’s more than enough time to change course if we need to, not to mention “minor adjustments”.

      I generally feel it’s more prudent to make small changes to our philosophy along the journey than to be “closed” and stick to something steadfastly.

      Ah, the changes to our life after close to two years maintaining this conversation online… =)

  3. LP

    Hi 15hww,

    Haha! Then I’m the epitome of lack of ambitions! I remembered the amount of peer pressure that told me that my job isn’t a job, even coming from my parents and close family! Oh, you’re a graduate, and you don’t have a proper 9 to 5 job? What a waste! When I go to social occasions, people gave me the blank look when I told them I’m a tutor.

    Seriously, all these doesn’t matter, but it took me quite a while to develop that quiet strength to release it. Then one day, I decided I should show others how great my life is!

    The thing is, my ambition is not aligned with others. Let them make them own battle with the corporate world, while I chill in a cafe with a cup of hot tea and a book, with my wife besides me. I dare say that most pple will not have as meaningful a job as mine, and I still love it after 10 yrs! I’m like a craftsman, and I will take a whole lifetime just to try to perfect my craft.

    So be it.

    1. My 15 HWW Post author

      Hi LP,

      There’s no doubt that what you did took great courage. I am about to find out soon enough.

      Actually, I don’t blame our parents for having that mindset and discouraging us from a hunter lifestyle. It’s unpredictable and humans are generally not conditioned for that ever since the agricultural age. But as a society, we are moving up the Maslow hierarchy of needs and many in our generation are looking not just for stability.

  4. Richard Ng (Invest Openly)

    15HWW : Follow your heart and do what you think is right and happy about, I don’t think our life should be defined by pure ambition alone. If that’s the case, many of us (including myself) will fail miserable!

    Keep going and keep smiling 😉

    1. My 15 HWW Post author

      Hi Richard,

      You’re the epitome of “keep going and keep smiling”, judging from the feed that appears on my FB. Alot to learn from you there. =)

  5. kyith

    i think they are right to a certain extend. we know that what we are doing is creating a margin of safety in life. That pretty much is understood (by us more or less)

    but the issue is, usually the most crazy work is done when you dont ahve that MOS. When things are on the line.

    you hear of stuff where people have 5 mil but still driving themselves harder to find the next unicorn.

    at a certain point you realize there is some truth to that.

    the solution to that i felt, is to have some harder to achieve goal for yourself to keep moving.

    lets just say that, getting to $XXX for margin of safety is not a simple and unchallenging goal by itself.

    1. My 15 HWW Post author

      Hi kyith,

      Well said, my friend. For the best part of the last decade, I have been making choices that have helped to create a greater margin of safety in my life.

      But I guess it’s time to be a little more adventurous and put a little more on the line and embrace new and more rewarding challenges.

      Hope to meet up with you soon again!

  6. cheekykoon

    Trust yourself and many others who are onto the path of early retirement.

    I have Mr Money Moustache ambition on my mind all the time. “When I have kids, I will not deny him time and say I have to work and unable to see you for your birthday party etc.” This mental awakening says a lot about modern living and the indoctrination of “values” unto us when young.

    Who are we working for anyway?

    1. My 15 HWW Post author

      Hi cheekykoon,

      Yeah, therefore I really want to work for myself and my own goals. Taking back full control of my time seems like a step in the right direction.

  7. Singaporemm

    Hmm, reminds me of what ERE said, about how peoples self worth and feeling of value are very tied up with their jobs. I guess there is a lot more to satisfaction and achievement beyond just a job.

    In fact, I would actually say that I gain more satisfaction making muffins and growing vegetables than like, doing work. Took me awhile to reconcile myself with it. But in the end, so long as you’re happy with your life, it’s alright even if you didn’t do XYZ. Hope you find a balance and a way out of your funk soon.

    Interestingly, GPs make a shit ton of money while not doing very difficult work. Just saying.

    1. My 15 HWW Post author

      Hi Singaporemm,

      My self-worth has a lot to do with what I spend most of my time doing, and unfortunately, it’s closely tied to a job right now.

      Not surprising, since a job takes up half of our waking hours on average, at the very least. I too find greater satisfaction from composing a good blog post or after a good run/swim rather than one-to-ones with management. I am out of the funk now and hopefully won’t slip into another one soon. Although it’s a matter of when, not if.

      I seriously feel that making lots of money doesn’t exactly mean one has more ambition than the other who is earning far lesser. It’s hard to compare and needs to be weighed more holistically?

      Anyway, you’re growing vegetables? Curious to what you are growing. Chilli/pandan or something more substantial?

  8. Small-Time Investor.

    Hi 15wwh

    This is common among people , many even up to 40s do not know what they want either too. Ambition to many in sg maybe climbing up the corporate ladder .

    I had a colleague who wanted to climb up the ranks so he can be more “chill” and “lax” on top of the added remuneration .

    I asked him ” so what are you going to do if you have 1 million sgd now ? ”

    He answered ” that have to depends on….” (with heaps of explaination. )

    in my heart , i thought, clearly he has no idea of what he wants for now.

    1. My 15 HWW Post author

      Hi Small-Time Investor,

      Many people are “institutionalised”. And I don’t mean it to be a negative thing.

      It’s what happened to us when we were young and continue on after we reach adulthood. Some people enjoy the hierarchical structure and their ambition is to climb to the top. Nothing wrong with that if it’s your cup of tea.

      But some of us are just built differently and mainstream success might not be that suitable.

  9. Alvin

    As you rightly pointed out, you are more aware about yourself after that incident.

    Should look at the meetup as something positive. Getting closer to what you want in life.

    Somehow I feel excited about what you gonna do next 🙂

    1. My 15 HWW Post author

      Hi Alvin,

      Firstly, apologies for not making it for the event you painstakingly organised. The funk probably led to the flu. Aargh…

      Yup, without the downs, the ups sometimes loses a bit of its shine. Will keep you updated on my plans the next time we meet for a chill lunch.

  10. Frugal Daddy

    Hi 15hrww

    Interestingly, I felt I am lacking of corporate ambitions too. However, after the numerous goals and dreams explorations that we have did, I reassured that I am on the right path.

    Dull and predictable is part and parcel of life. You don’t get excitement all the time. Just like a true love can’t make your heart beat faster every time for the next 50-60 years. A normal and simple love can still be a true love. Just an random example used.

    Have fun enjoying your life.

    Frugal Daddy

    1. My 15 HWW Post author

      Hi Frugal Daddy,

      Thanks for reaching out to me privately. Appreciate your kind advice and suggestions.

      If the things I am doing predictably gives me happiness, I doubt I would be upset and there wouldn’t be cause for change. But if it’s predictably causing me some pain and frustration, then not changing cause might be a recipe for disaster.

      Hope you had a good Fathers’ Day celebration with your family yesterday!

  11. Createwealth8888

    After nearly 40 years of working, I have known the truth in the corporate world. Lack of ambition and lack of real hard work; it is quite impossible to climb very high up in the corporate ladder.

    1. My 15 HWW Post author

      Hi CW8888,

      When you climb very high up when you do not have the natural ability, it can be quite tiring to stay up at the top. Besides money, status and power are two other rewards. Of which I have very little interest in too.

  12. Joyce

    A lot of people tie their sense of self to their jobs…it’s probably not very healthy in the long run I think and I guess the reunion is just food for thought of who are your real friends…

    1. My 15 HWW Post author

      Hi Joyce,

      I still believe that this bunch are good friends that will offer us help in times of need. I survived JC when many of them lent me homework to copy and notes to revise.

      As human beings, it’s hard not to be judgmental and I do not blame them if they really do think I am lacking ambition, especially considering how unsatisfied with life too. It’s just like how a successful trader making 50% returns might look at an index investor who is unhappy with his 5% returns.

      If you’re unhappy and not making changes when your circumstance allows you to, one is likely lacking ambition.

  13. AK

    Hi 15HWW,

    I am a very lazy fellow. I just want to be comfortable. Is that wrong?

    Ambition? Sounds like lots of work. Some people have lots of it. Some people have a bit of it. Some people don’t have any. So? What’s new? Some people are hairier than others. ;p

    ‘I choose a lazy person to do a hard job. Because a lazy person will find an easy way to do it.’ – Bill Gates.

    Bill Gates is a wise man. 😉

    1. My 15 HWW Post author

      Hi AK,

      Interestingly, I do regard myself as lazy.

      But even lazy people do have some form of ambition. Like I mentioned in my latest post, I really don’t think you just want to be comfortable. *wink*

  14. Jared Seah - SMOL

    Hello 15HWW,


    So many of your readers have read your words but they have not “read” your heart…

    Your JC friends were “right” hor?

    Glad that event was a catalyst and wake-up call.

    Come to think of it, this post was never about what your JC friends have said 😉

    Coming from a grasshopper, I would say the same to you – you are NOT “ambitious”.

    I’ll do one better than your JC friends; I’ll give you a kick!

    Your wife has done it already.

    What the hell is holding you back!?

    Onwards 15HWW!

    P.S. “Onwards” is the war cry from my Gan Eng Seng Secondary School, I like!

    1. My 15 HWW Post author

      Hi SMOL,

      Can trust you not to hold anything back. And you are right that at the end of the day, it’s not what they said.

      It was how I felt about myself, at this point in time, when I don’t want to do what I “should” do.

      I do deserve the kick up my ass. =p

  15. EnSabahNur


    I think the important thing is to make a distinction between working hard for the sake of money and working hard because it is a challenge to oneself or a way of betterment.

    There are many ways to make a living in this world, and who is to say which is better than another?

    Working hard because it is a way to self-improvement, now that is different. I agree with you. If we constantly take the safest route, we lack challenges that push us out of the comfort zone. Without that, we stagnate, or worse, atrophy.

    1. My 15 HWW Post author

      Hi EnSabahNur,

      Well said. I don’t want to work hard because of some external validation (i.e. resume looks better). It has to be intrinsic and a challenge that I want to take on deep down.

      And yes, I was atrophying. Maybe even wallowing in my comfortable misery that’s somewhat self-imposed.

      Thanks for your clear insight.

  16. Rolf Suey

    Hi 15HWW,

    I have to agree to you that you are lacking work ambition but not life ambition. Somehow since “work” (need not be corporate but something u like to do consistently for few to many hrs a day for many yrs) is also important part of our life.

    I think end of the day, we still need both work and life ambition balance.. Even when we are beyond 60..

    First we should probably figure out who we really are, “what r we good at or not good at” then from there develop our work ambition.

    It’s better late than never. Keep searching do not settle. Do not ever use FI as an excuse for u to stop searching ur work ambition.

    Ps: I like Onward bcos I was from Gan eng Seng also!!! that is motto of my life

    1. My 15 HWW Post author

      Hi Rolf,

      Working beyond 60? I agree with you! That’s why I have never advocated full retirement. Semi-retirement is just about right.

      I wanted to be FI to “escape” from something. But I can’t escape forever and I simply can’t delay this search for something that is a better fit for me.

  17. RB35

    Hi there 15HWW, I have faced the same issue too. My contemporaries have told me that I lack ambition as I don’t want to be a hermes clad MD calling the shots.

    In fact my ex girlfriend dumped me because she thought I was the least ambitious investment banker she came across (in part that was the reason :D). When other junior bankers were talking about climbing the ladder, all I could think about was what make my new dragon age character was going to be. When others were talking about what holidays they were taking, I was talking about new investments.

    I have come to realise that ambition does not mean the same thing to everyone. Just because one’s ambition may not involve corporate aims do not make them less ‘ambitious’ than others’. In the same vein they do not make it more ‘ambitious’ as well 🙂

    Sometimes if folks just wana do the corporate threadmill hustle, you gotta respect their views and let them do so. Please do not encourage them to leave the rat race, otherewise who gonna be the consumers that will fund our investments??

    1. My 15 HWW Post author

      Hi RB35,

      I learnt something the other day from another blog that describes myself quite aptly. 不想管人也不想被别人管。

      Perhaps that’s really my ambition, to move to that stage in life. Quite lofty, eh?

      That’s a scary gf to have, in my opinion. I can’t imagine my wife dumping me just because I can’t march to the same tune as countless others. Perhaps people like us are just the contrarians, and there will always be the majority that are willing to fund the lifestyles of capitalists.

  18. GP Blogger

    Dear 15HWW,

    Best of luck for your new found ambition.
    I really feel that we should live life on our terms.
    I considered myself as a lazy person but now I know that I am in great company. I think Laziness is a part of mindset to not to blindly follow things. most of the time the routine stuff just does not interest us.

    My work & life ambitions are very different from my peers & sometimes I wonder whether what I have decided is the right path. Then wandering a little I then return to the lazy path praying to god to give me the strength & the courage to do the right thing, to be lazy.

    1. My 15 HWW Post author

      Hi GP Blogger,

      Seems like I found a kindred spirit. =)

      Especially after a quick browse and read on your blog. Most people’s lives are running on auto-pilot and many fail to stop and contemplate why they are doing “this” and if there’s a need to continue doing “this”.

      Hope you are feeling much better now after your recent BIG decision.