Salary can give success a number, but it is not enough to tell you whether your life is a success. I learned that when I took a lower-level, lower-paid job to learn something new—and found that knowing the trade-off did not stop salary from feeling like failure.
The Enoughness Question matters more than another salary benchmark
The Enoughness Question. Eileen’s personal lens asks what money is meant to make possible, rather than treating a higher salary as the default definition of success. There is no universal amount of money that is enough. For me, earning more stopped being a useful answer once it could no longer explain what I wanted from my life. The better questions are whether I will regret the life I am leading now, whether my 80-year-old self will thank me, and whether my eight-year-old self would look up to me.
Salary can become an incomplete measure of success
I miss being a student because success was clearly defined. My mom made it simple. She boiled it down to a single number: my rank in class. It did not matter if you scored 97. If you came third, you still had room for improvement.
The metric changed once I started working, but the principle did not. I still had one number to measure myself against. My grandma compared with her neighbours how much each of their granddaughters was earning. I felt proud when she won because it meant I had made her look good. Privately, I would use the salary tool the Straits Times publishes every year to see what percentile I sat in for my age and sector. I did well. Sometimes, just for the sting of it, I would scroll the Reddit HENRY forum, short for high earner not rich yet, and feel lousy compared to the 20-year-olds who had made millions exiting a company or inheriting from a rich uncle.
A deliberate pay cut can still feel like failure
But I lost the scaffolding a few years ago when I changed jobs. The new role was at a lower level and paid less. I knew that going in. But it still messed with my head. I felt like I was failing whenever I measured myself by my current salary versus what I could have been earning, even though I told myself I was trading the money for learning something new.
For readers weighing a similar transition, switching industries mid-career in Singapore is one practical version of that trade-off.
For the first time, I had to find a new metronome. That pulled me into a midlife crisis. What is life about, if not the next pay band?
Pleasure and service are useful tests, not universal answers
I asked around. The two most common answers were these.
Pleasure. A friend in his sixties told me I was thinking too much. He said life is about chasing pleasure. He ran his first marathon at 40, podiumed in his age group, and now flies overseas for ultramarathons. I tried his answer. I travelled so much that my sister joked I did not deserve to be Singaporean because I was hardly in the country. But travelling did not give me what I was looking for. The clearest moment came last month, when I was window shopping in China. I walked into a mega store and saw a line of women waiting outside a fitting room. The whole scene looked silly from a distance. I wanted to shake them and wake them up. What are you wasting your time on all this for?
Service. Other friends have skipped pleasure and built their lives around someone or something else. My friend is a single father. His whole life revolves around his daughter. He sends her to school, works a bit, packs her lunch, picks her up. He would be lucky to have time to exercise, never mind sit and think about what his life means.
More income does not define what you want
A variation is service to a higher cause. Another friend used to chase pleasure as far as money would take him. He has eaten $600 steaks and drunk $2,000 wine. He told me the food was out of this world but the pleasure was fleeting. He has given up chasing pleasure and now spends his life preaching the word of God. He says that is the one thing that has not dimmed for him.
I know service is bigger than kids or faith. People build lives of service to a community, a craft, a country, a cause. I have not yet found one that picked me, and I have not gone looking hard enough. Maybe that is on me. For now, it is not the answer.
Since neither pleasure nor service worked, and people have been asking it for thousands of years, I went looking at what people more accomplished than me had done with the same question. Three of them stayed with me.
Three ways to define success beyond salary
1. Can you build a life that counts for something?
Musk has talked openly about hitting this existential crisis as a teenager. Pop culture has it that he found his answer after reading The Hitchhiker’s Guide to the Galaxy. In this science fiction, a supercomputer takes millions of years to work out the answer to life, the universe and everything, and the answer is the number 42. The joke is that nobody knew what the question was.
Most people use that anecdote to explain Musk’s whole business empire. He is making us interplanetary through SpaceX, building AI to give us tools we do not yet have, and using Twitter to give people a public square where they can think out loud together. He wants to widen the extent of what humans are able to think, so one day we can come up with a better question about why we are here.
I think that explanation oversimplifies things. Musk has named Nietzsche as a big influence, and most people do not know much about Nietzsche beyond the cliché that he was a nihilist who said life has no meaning. That is only half right. Nietzsche did say life has no built-in purpose handed down to us, but his point was about what people do with that fact. He thought people respond in one of two ways. Most fall into herd mentality, where you let the people around you decide what is respectable and chase that. That was me with my class rankings and my salary. The rest fall into nihilism, where you decide nothing matters and you disappear into food, sex, work, scrolling, and routine to numb the confusion.
Nietzsche wanted you to do neither. He wanted you to decide for yourself what matters and live by it. He called the person who manages this the Übermensch, German for “the overman” or “the one who goes beyond.” He meant the person who climbs above the herd’s standards and the nihilist’s despair to create their own. Most people want a comfortable life. The Übermensch wants a life that counts for something. That, I think, is what Musk is doing.
But Musk sets the bar at world-changing legacy, which is hard for someone unspectacular like me to use to determine the meaning of my life. I needed something more attainable.
2. At 80, will I regret this?
I found that in Jeff Bezos. Bezos was 30 in 1994. He was a senior vice president at D.E. Shaw, a hedge fund on Wall Street, one of the youngest on staff at that level. He came across a statistic that the web was growing at 2,300 percent a year. He thought selling books online could work. He went to his boss, David Shaw, with the idea. Shaw told him it was a good idea, but a better one for someone who did not already have a good job. Bezos went home and thought about it for 48 hours.
He came up with a thought experiment. Picture yourself at 80, looking back. Which choice would you regret less? He decided that at 80, he would not regret trying to start an internet bookstore and failing. He would regret not trying at all. He quit the hedge fund, drove to Seattle with his wife, and started Amazon out of his garage. Amazon did not turn a profit for the first seven years.
Bezos’s test is the modern version of something Nietzsche had asked a century earlier. If a demon comes to you in the middle of the night and tells you that you must live this exact life again, on loop forever, every joy and every humiliation, do you curse him or can you say yes? He called it the eternal recurrence.
That is now my guiding rule for making difficult decisions in life. But Bezos and Nietzsche only help me work out what I do not want. I was still missing a way to picture what I do want. Eileen Gu gave me that.
3. Would your eight-year-old self look up to you?
Eileen Gu is the Olympic skier who competed for China and went to Stanford. A reporter once asked her if she thought before she spoke and whether she could walk through her thinking. She gave the usual lines about being introspective and journalling. Then she said something that clicked for me. She can choose what she thinks. By choosing what she thinks, she becomes the person she wants to be. The person she is becoming is someone her eight-year-old self would have looked up to.
That last part of her answer made something click for me. Would the eight-year-old version of me look up to who I am today? The eight-year-old version had clearer ideas about what a fun and fulfilling life looked like than the adult version does. The eight-year-old me thought SGD 4,000 was a lot of money and would not have wanted much beyond that. She would have spent the rest of her time on something she was passionate about.
A personal definition of enough makes life feel like your own
It is not a coincidence that the three answers I kept all point in the same direction. Bezos asks if your 80-year-old self will thank you. Nietzsche asks if you would do the whole life again. Eileen Gu asks if the kid version of you would look at you now and feel proud. Three different angles on the same question: will I regret the life that I am leading now?
I have found my answer. It is private and I will not publish it.
That is why this is not my usual post with the answer wrapped in a bow. Yet I still wanted to share this because I hope you’ll consider this question. We have 900 months on Earth, about 75 years, and most of us are already a third through it. Time runs like a toilet paper roll. The closer you get to the end, the faster it runs out. For those in your 60s, if you want to plant a durian tree, plant it now. It takes 15 years to grow a tree from seed. Wait too long and you will not be around to taste it.
Quotes that informed my search
Marcus Aurelius
Marcus Aurelius was the Roman emperor from 161 to 180. He kept a private journal between battles on the Danube frontier, writing notes to himself about how to live. The journal was published after his death and is now called Meditations.
“Human lives are brief and trivial. Yesterday a blob of semen; tomorrow embalming fluid and ash.”
“Your life is almost used up, and instead of treating yourself with respect, you have entrusted your own happiness to the souls of others.”
Wee Kim Wee
Wee Kim Wee, our second president, wrote a collection of essays called Glimpses and Reflections in his last years.
“We have not come to this planet merely to work, slave, sacrifice and suffer and then take leave. At some point of time in one’s life, it is important to seek quality life. Quality life is not about chasing the almighty dollar, but finding contentment.”
Albert Camus
Albert Camus, the Algerian-French Nobel Prize winner, opened his book The Myth of Sisyphus with the hardest question.
“There is but one truly serious philosophical problem, and that is suicide.”
His answer was that you do not kill yourself, and you do not lie to yourself with hope of some future redemption either. You live anyway, in plain sight of a universe that offers no reward for it.
Compare that definition of enough with the practical choices involved in leaving full-time work for a portfolio career, deciding whether an AI course is worth paying for and switching industries in mid-career.
Frequently asked questions
Is there a single amount of money that is enough?
No universal figure is offered here. The eight-year-old me thought SGD 4,000 was a lot of money, but the point is not to find a salary target. It is to find a definition of success that salary alone cannot provide.
Why did a lower-paying job feel like failure?
I had knowingly traded pay and seniority for the chance to learn something new. Yet, after years of using salary as my measure, comparing my current pay with what I might have earned still made the decision feel like failure.
What can I ask myself when salary no longer defines success?
Try the questions that stayed with me: Will my 80-year-old self regret not trying? Would I live this exact life again? Would my eight-year-old self look up to who I am today?
Are pleasure or service the answer?
They can be meaningful answers for other people, but neither settled the question for me. Travel did not give me what I was looking for, and I have not yet found a cause, community, craft or faith that feels like my answer.
How I make time to write while working full time
I work full time, so if I only wrote when I have an uninterrupted hour every evening, I probably wouldn’t have built much of a LinkedIn presence.
What I do is collect my stories while I’m walking, cooking or tidying the house in a “story bank”, then sit down and edit them into articles later.
I’ve tested a few dictation tools over the years, including ChatGPT and Wispr, but Typeless is my favourite because it understands my Singaporean accent. It’s also smart enough to edit out my “em’s” and “ah’s”, copyedit my rambling, and use numbered bullets whenever I start making a list.
The tool I use is Typeless: https://www.typeless.com/?via=eileen
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