“I should have bought insurance earlier”

“I should have learnt investing earlier”

“I should have paid attention to my health earlier”

Regret Financial
Regret: Financial Decisions that went wrong

For years, I have been hearing these from clients, friends or just people I meet during networking session. They were also the ones who ask me to write an article about regrets – what they are, why we have them and how to get over them. For years, I have avoided writing this article in fear I would screw up and never get over it.

(Okay, that was a lame joke… I regret writing it.)

On a more serious note, I would like to write about this emotion called regret and how it appears in our financial journey and what we can do about it.


Peter’s Regret: assuming only the best can happen

Regrets Nothing will go wrong
Regrets: Assuming only the best can happen

Peter (not his real name) is 30 years old and a high flyer in a financial institution. As a friend, we were very proud of him as he is THE most responsible and capable person in our group. We have high hopes for him and believe that he will be the first one to reach the top of the corporate ladder. He is the type of person in your clique who seemed to get everything “figured out”.

On a rare occasion that I was chatting with him alone, Peter told me that life is good. He believes that people who are not at his level are just simply “not working hard enough”. For some reason, I steered the conversation towards financial planning and in particular insurance.

Peter: “CK. I’m 27 (at the time). I get Gold for my IPPT every year. Illness happens when we are older. We have to look at it on the probability angle. What are the chances of me suffering from a illness now? I will look at insurance when I’m 55 years old. That’s when I will need it the most.”

Being a new consultant then, I didn’t make a stand for him to be responsible for his financial decision. There were some sense to what he was saying and I wasn’t prepared to have long conversation about insurance on our chillax night.

Things changed 4 years later. In Peter’s annual health checkup provided by his company, he found out that his cholesterol issue went out of control. His LDL count is 300mg/DL and his total cholesterol is 7 mmol/l. The doctor advised Peter that this issue has to be addressed IMMEDIATELY.

According to the doctor, heart related illness (ie Heart Attack) is common for his health report profile and asked Peter if he had health insurance. I can’t imagine what Peter was going through. When I look at Peter that weekend, the vitality in his eyes that he once had was gone. It was replaced by a look of desperation when he realized his Health insurance covered for treatments… except heart related incident. I can remember one word that he used which made both of us quiet after that.


I never asked what he meant. It could have meant “how could this happen? It could have meant “How should we proceed from now?” Or it could have meant a deafening regret.

Peter remains bitter towards insurance companies now as he didn’t feel that one day, he will be rejected by them. Deep in his heart, he knew that it was his decision. Peter’s regret is a decision on thinking that some issue could wait and only the best could happen. There was a period he felt bitter, emotional and unjust as he felt this shouldn’t happen to him. Now, he is doing all he can to improve his health by exercising and hopefully, the insurance company will accept his risk profile one day.

Personally, I regretted not taking the stand for Peter that day. Seeing Peter bitterness towards insurance companies make me guilty and somewhat responsible for how he is feeling. There were some days I thought how things would be different if I made the stand for him. Every new prospect who refused an insurance program that I crafted reminds me of Peter. Peter has requested me to share this story with them and hopefully, they will not experience the same regret as he has.


Jane’s Regret: not doing it

Regret Not Starting Early
Regret: Not Doing It

Most people have regrets over what they didn’t do, rather than what they did do. In the end, we regret the chances that we didn’t take. In this very quota-table quote on regrets, Jane is one of them.

I was not part of Jane’s journey until she was 55. I met Jane in one of my Wealthdojo seminars. She is very full of energy, life and spirit. I would say she could easily pass off like a lady in her early 40s. In the eyes of her friends and myself, it feels like she’s already “there”. She could easily take time off to do what she likes, eat what she wants and travel anywhere. The very first time I met her, I thought that she is someone who probably had planned well for her finances. Until I asked her.

Jane: “CK. I don’t really have job security at my age. To be honest, I have a high pay which is why the company would want to get rid of me fast if the economy is not doing very well. I don’t have much saving. I wished I had started planning for my finances earlier”

I choked into my coffee silently. I looked at Jane who was looking down at her coffee. She look lost, tired and afraid. In that situation, I mastered some courage and ask why didn’t she start saving/investing when she was younger. Her eyes filled with guilt, looked at me and said.

Jane: “You know. It was very troublesome to learn all these finance stuff. Work was busy and during the time I wasn’t working, I wanted to spend time with my family and friends to de-stress. Looking back, I should have started earlier. I probably can retired by now.”

You could feel that the guilt and regret growing deeply in her. As if waiting for a sigh to happen, she exhaled.

Jane: “Will it be too late if I start now?”

It is never too late. The question is, why wait until it is too late.


Karen’s Regret: Obsessions

Regret Obsession
Regret: Do you have an obsession?

Karen is a 45 year old lady. I met Karen recently and she expressed her regrets with me during a time we had coffee. Karen is married with 2 children and have an weird obsession. She admits to me she has an obsession with bags and shoes. During our conversation, she will mentioned about her husband persistent attempts to stop her from buying bags.

Karen: “After all these years, he still haven’t given up on me. I’m glad.” She said it with a satisfaction on her face.

Karen: “I am already drained after working. When I get home, it is worse. I feel a lot of pressure from my growing children too. When my children get sick, I feel powerless. Many a times, my husband asked me what I fed them. It make me feel like I’m the one poisoning my children. I don’t like it. The only thing that I can make me happy again is to shop and maybe buy a bag”. She laughed but then paused in her tracks.

(Noticing that this could be deeper than a finance issue, I asked more about her family and will not be discussing the content of the discussion here)

Wanting to understand more of the expenditure pattern, I asked about the average price of her bags and the frequency of the purchases.

Karen: “I would buy 1 bag a week on average (*I choked in my coffee here) and it cost between $500 to $6000. I probably have around 150 of them at home now. They are probably worthless by now”

She looked at me in hope I would say something about the resale value. Unfortunately, I wasn’t an expert on luxury bags. I asked her if she would like to begin her financial journey now, probably save $500/month in a endowment where she can’t touch the money until maturity.

Karen: “I think $500 is too much. I don’t have much money to save. Actually, I just bought a bag last week…”

That was the last I heard from Karen. In her journey with money, I acknowledge it might be something more deeper than a finance issue. However, the obsession with bags (or any other items) cause a dent in her retirement planning. My personal estimate of her total retail bag price is around $200,000. Karen expresses regret in her action. However, I feel her regret is not truly felt at the moment.


Any other regrets?

Regret Proud of you
Regret: No matter what happens, I’m proud of you that you got through the past

I’ve struggled with decisions/FOMO throughout my life. But never felt I regretted on something. Of course, I’ve made mistakes, missed opportunities, hurt people unnecessarily, screw many things up. I’ve made cringe-worthy decisions so many times that I’ve developed incredibly resistance to regret.

Everything I’ve done wrong in the past is still part of what makes me who I am today, so why would I ever regret who I am today? That’s like slapping yourself in the face to prove to yourself that you’re can feel pain. There were many decisions I made in my financial journey which I do not appreciate now. However, this can only come with maturity, experience and hurts. Though the outcome was painful, it serves as a lesson for the future and I’m glad to say. I did not regret one bit.

I hope that these stories of regrets (of real people with frictional names) can guide you to make a better decision in your financial journey. We wish you all the best.


If you read until here, thank you again for your patience and your support over in 2019. I hope that in 2020, Wealthdojo can continue to value add you. Let us know what you think in the comments below. This is a working article. The above doesn’t represent my stock recommendation in anyway. Please read our disclaimer for more information.

I hope to nurture genuine relationships with all of my readers. Please feel free to contact me on my Instagram (@chengkokoh) or Facebook Page or my Telegram Channel!



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