Financial Regrets: Lessons from Personal Experiences

Selling my flat lost me over £500,000

Andrew Montlake, founding partner and mortgage broker at Coreco

One of my most significant financial regrets is selling my flat in Highgate, a highly sought-after area in north London, to purchase a family home back in 2007. At that time, my wife was expecting, and we needed more space than our modest one-and-a-half-bedroom flat could offer. While I had some savings, they weren’t quite enough to keep my flat while also financing our new home, so I made the difficult decision to sell.

I sold the flat for £310,000, a considerable profit from what I originally paid, but now it’s worth around £700,000. Looking back, I regret not exploring alternative financing options to cover the shortfall. The rental income from the flat alone would have easily covered the mortgage. It’s ironic that, as a broker who has guided numerous clients through similar situations to build their property portfolios, I currently own only one property. Beyond the monetary loss, it’s also disheartening that it could have been a fantastic starter home for one of my children.

“I didn’t understand the need for a pension when I was young”

Chris Pitts, CEO of First Direct, a bank offering free access to financial coaches for account holders

My biggest financial oversight has been failing to recognize the importance of a pension early on in my life. Coming from a modest background, I lacked a financial safety net, making me acutely aware of the need to fund my family’s day-to-day expenses. This led to a mindset focused on immediate financial obligations rather than long-term planning. I concentrated on providing for my children while they were dependent on me, but I failed to look beyond their current needs.

Now, as I approach retirement, I realize my time for investment growth is limited. While I hope my cautious approach to saving will pay off, I often view my pension investments with uncertainty, wishing for a more secure financial future.

Not claiming child benefit for any of my four children

Anonymous reader

I regret not claiming child benefits for any of my four children. Due to my autism, filling out what others consider a “simple” form feels as daunting as climbing Mount Everest in flip-flops, and I just couldn’t manage it. My children are now adults, and I missed out on claiming this benefit before the two-child cap was introduced. Recently, I calculated that this oversight has cost me over £50,000 in total, which is a thought that genuinely makes me feel unwell.

Buying a £300 chair that I’m now too scared to use

Ben Gartside, senior reporter at The i Paper

While my worst financial mistake might be spending thousands on a sub-par university education, I also made one purchase that I cherish deeply. Last year, I bought a stunning designer Robin Day chair for my office, which I absolutely adore. It cost me £300 second-hand from a kind pensioner who wanted to help out a fellow design enthusiast.

The only issue is that I’m terrified to sit on it. This anxiety is irrational—I don’t mind if others or even my cats sit on it; I just can’t bring myself to do it for reasons I can’t quite explain. I love that chair and often find myself sharing pictures of it with colleagues, much like a proud parent shows off photos of their child. It symbolizes my progress in life, and I genuinely hope to sit in it more often in the future.

Relying on a dodgy financial adviser

Relying on a dodgy financial adviser

Jean Boshier, reader

Growing up in New Zealand, I had little understanding of finances. My parents struggled to provide for five children, leading to constant competition for limited resources. When my husband and I moved to London in 1972 with just £100, we started a successful business. However, after we split, I discovered the pensions he had set up for us in the 1970s were riddled with exorbitant commissions for the salesman who sold them. I had believed I wasn’t smart enough to manage my finances, but after educating myself, I realized I could take control.

Despite my newfound confidence, I sought the advice of a financial adviser for a significant decision involving an annuity. To my shock, I learned he would be taking a 3.5% commission from my interest payments—an astonishing cost over the years for a deal he probably spent minimal time on. Fortunately, I caught this in time, within the 30-day cooling-off period, allowing me to withdraw and reinvest elsewhere. This experience taught me to rely solely on myself for financial decisions, and I have since encouraged friends and my daughters to invest wisely, signing off emails to them as “Mrs. Buffett.”

“My pot could be much bigger now if I’d stashed some money away in my 20s”

Grace Gausden, Money and Business editor at The i Paper

I’ve always been prone to spending—a fact I’m not particularly proud of as a money editor. I enjoy buying new clothes, dining out, and traveling as much as possible. Although I’ve never been in serious debt (if you don’t count student loans), saving for future needs didn’t come naturally to me.

In my mid-20s, this wasn’t a pressing concern, but now that I’m in my 30s, I regret not saving more. My parents didn’t have a financial cushion to provide when I turned 18 or 21, though they’ve always been there to assist me when needed. The idea of starting from scratch to save for a house deposit felt overwhelming, so I didn’t pursue it.

However, I eventually began saving around the age of 26. Initially, it was a small amount, but as my income increased, so did my savings. My husband and I managed to save thousands, which went towards our wedding last year. With that milestone behind us, we’re now focused on increasing our monthly savings to eventually buy a home. We keep our savings in cash accounts, actively monitoring interest rates to maximize our earnings.

While our savings are substantial, I can’t help but think how much larger they could have been had I started saving earlier in life. Nevertheless, I’ve learned a valuable lesson, and I’m committed to saving as much as possible while cutting back on my frequent shopping sprees.

Not getting my head round investing sooner

Callum Mason, deputy Money editor at The i Paper

Aside from contributing to my pension, I only began investing in my late 20s. Instead, I opted for cash savings accounts, which, for the majority of my adult life, haven’t yielded significant returns due to low-interest rates. I was 25 when the Covid pandemic struck, and I realize now that had I invested in a stocks and shares ISA back then, I would likely have a much larger savings pot as I enter my 30s.

The reason for my delay in investing was my aversion to doing things with my money that I didn’t fully comprehend. Even when friends recommended investing, I hesitated. I’ve come to understand that one doesn’t need to be overly active in picking stocks and investments if that’s not appealing; there are plenty of managed funds available with relatively low fees if you shop wisely.

I believe investing is a great way for young people to enhance their income in an economy where pay raises are scarce and essential items, like housing, are increasingly out of reach.

Not saving into an ISA

Anonymous reader

My biggest regret revolves around not taking advantage of ISA allowances for myself and my three children. Despite knowing it’s a careless oversight, every April deadline slips by without action on my part. I repeatedly miss the opportunity to open an ISA and transfer my money there, leading to unnecessary taxes on my savings. In total, I estimate this has cost me around £3,000.

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