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I could have been rich! Biggest financial mistakes

180 replies

rememberitalltoowell · 06/11/2025 08:38

And how you come to terms with them?

I turned down a really well paid role for something else that didn't turn out as planned, and could only find much lower paying roles afterwards. When I work out what that decision cost me over the course of my career, we're talking hundreds of thousands!

OP posts:
FunnysInLaJardin · 06/11/2025 22:52

Tatwrap · 06/11/2025 14:08

I am a lawyer
in house
I earn very well and have a great home life balance

me too, although private practice

Otins · 06/11/2025 22:55

Franpie · 06/11/2025 18:54

I have a really awful one that I regularly try not to think about…

In 2013 I had an analyst working for me who recommended I buy bitcoin. The price had just fallen to around $50. We had all just had our bonuses paid out and he said he was going to use all of his £30k bonus to buy bitcoin and he strongly recommended I did too. Easy, guaranteed money he said.

I said that I never invest in anything I don’t understand. He proceeded to try and explain the concept of bitcoin to me but I still didn’t get it. He then almost begged me to at least buy £1,000 worth and see how it goes and he’ll be proven right. I ummed are aahed but ultimately decided to stick to my rule of never investing in something I don’t understand.

OP, if I had invested that £1,000 I would now be sitting on over £77million today.

So your analyst friend, assuming £1000 would now = £77m, and he invested his £30k, he’d now have £2310m????

Piknik · 06/11/2025 22:57

I've got three things that haunt me

  1. Landlord offered to sell us our rental property - a two bedroom split level two bed flat in a huge three story Victorian house in Maida Vale. It was 1996 and he wanted £65K for it. My dad said that sounded a 'bit punchy'...
  2. I was pretty much the sole visitor and friend to my extremely wealthy, utterly lovely Uncle (with no wife or children). When he turned around 90, he asked me if I needed any money. I did, but was too proud to say yes. So I said 'No. I'm fine'. He asked again a year later, and again, I said no. When he passed away, he left his entire estate of £14million to animal charities. I know... I know... but it still wish I'd been brave enough to ask for enough to cover my debts.
  3. I work in film/tv and I pitched the idea of an animated KPop band to a few people about five years ago, and then again about three years ago. Execs didn't understand the market. I can't even look at Demon Hunter merchandise without feeling furious.
Franpie · 06/11/2025 23:05

Otins · 06/11/2025 22:55

So your analyst friend, assuming £1000 would now = £77m, and he invested his £30k, he’d now have £2310m????

My analyst now leads a very different life!

We’re still friends on FB and his last update he was on his massive yacht off the coast of Turkey for the summer.

A few years ago he did invite us to his wedding. The most lavish thing I’ve ever been to, taking over an entire 5 star hotel in central London for the weekend.

He’s obviously cashed some in over the years to buy the boat and pay for the wedding!

Diydanny · 06/11/2025 23:09

AmpleSwan · 06/11/2025 11:02

I bought £20 of Bitcoin out of curiosity in 2011 when it was a new thing. I can't remember exactly how much that was in Bitcoin but it was more than one and less than two. I spent it on a some basic ditgital services, maybe a game subscription? That would be over 200k now...

Hope you are holding some XRP then

Timeforhector · 06/11/2025 23:15

ForeverDelayedEpiphany · 06/11/2025 21:28

I have to say, my biggest regret isn't financial but with my health.

I've got a permanent neurological involuntary movement disorder called tardive dyskinesia that was caused by an off label antipsychotic, prescribed for severe insomnia and anxiety after a head injury.

If someone offered me £10m and a huge house, I would say no if if meant I could be in rude health again.

Health is most definitely wealth 🙏 💯

So sorry to hear that @ForeverDelayedEpiphany
Which antipsychotic caused those issues?

Mumtobabyhavoc · 06/11/2025 23:15

Diydanny · 06/11/2025 23:09

Hope you are holding some XRP then

It was around $1000usd.

Mumtobabyhavoc · 06/11/2025 23:16

My mistake was mutual funds and some stocks that tanked. 😰

Poetnojo · 07/11/2025 00:03

One of my brothers told me about crypto currency when it was in its infancy, he said I should buy bitcoin, which was literally only a couple of quid each at the time. I thought it sounded like pie in the sky and I was budgeting every penny back then so I passed up on it. He himself bought some but cashed out when they went to a few hundred each. Another brother bought loads and is now very well off. I really regret not buying it.

ForeverDelayedEpiphany · 07/11/2025 00:08

Timeforhector · 06/11/2025 23:15

So sorry to hear that @ForeverDelayedEpiphany
Which antipsychotic caused those issues?

Thank you. It was a week of a first generation typical antipsychotic called Pericyazine 💔😢

Everyoneishangry · 07/11/2025 01:59

Marriage

RollerTop · 07/11/2025 04:03

When I was young. I was insanely shy and had v low self esteem. Literally hated myself. I look back in sadness of how I was and all the opportunities I've missed due to holding back and how it's moulded my life.

I did this with a guy I met at uni. He was cute and sweet and a bit nerdy but in a nice way. He took an interest in me and id never dated before. I didn't know how to deal with the positive attention so panicked and brushed him off.

He went on to set up a tech company which he went on to sell for hundreds of millions.

I always wonder what would have been if I had the courage to say yes.

Henrysmycat · 07/11/2025 04:08

I followed the money career wise. It cost me my health. I’m chronically ill now with life limiting conditions and earlier death chances. I’d give all the money back if I could have my health intact.

TheaBrandt1 · 07/11/2025 04:24

I was young and gorgeous and single and working in the City. Two guys from work asked me for a coffee. One I fancied and clicked with the other I just didn’t fancy.

Ended up marrying the one I fancied. When Dh heard about the other guy he said I’d made a massive mistake choosing him as the other chap was the only son of one of England’s wealthiest families (you will have heard their name it’s on lots of things). Stand by my choice but sometimes wonder!

InterestedDad37 · 07/11/2025 05:18

I had two extremely rich girlfriends when I was young (at different times, of course). One, I have no idea what her life is like (lives abroad), the other one is still a good friend, but our lives are rather different 🤣

Chillithai · 07/11/2025 05:44

Bobbingtons · 06/11/2025 21:03

You clearly weren't around in the tech boom of the early 2000s when the patent wars were going on and it was the whole west with mobile phone company's spending billions on acquiring and fighting patent battles. The best example is the defence of the 1 click buying patent Amazon held for 18 years.

As I said it was more complex than just a concept, it was a description of the process of achieving that result using software and hardware interacting in a specific way.

And the Apple bods and tech whizzes would have been beavering away on it, alongside a multitude of other ideas @Bobbingtons

Simplestars · 07/11/2025 07:17

Henrysmycat · 07/11/2025 04:08

I followed the money career wise. It cost me my health. I’m chronically ill now with life limiting conditions and earlier death chances. I’d give all the money back if I could have my health intact.

What was this? Could you share to educate us.

macshoto · 07/11/2025 08:38

Talked seriously with friends about moving all my money into Euros pre the Brexit vote and didn’t get round to it. Missed out on a significant overnight gain.

More readily correctable for others… didn’t start an equity ISA as early as I could/should have done. Even if it had only been a small amount each month, I would have a lot more savings now if I had started earlier.

Didn’t put as much effort into finding a mentor at a critical time in my career as I should have done. Got buried in doing the work, and didn’t focus on my own career trajectory when I should have done.

Henrysmycat · 07/11/2025 09:18

Simplestars · 07/11/2025 07:17

What was this? Could you share to educate us.

Two types of aggressive cancer, still not in remission, failing liver from medications and an autoimmune that keeps me in hospital 2-3 days per week. Can’t go even around the corner for holidays as I might need my hospital. My life expectancy is low as well due to all of the above.
I ignored some health signs due to chasing my career and insane amounts of work and stress. I got sick and left everything and can’t even do a few hours of work or even volunteering to get out of the house. I don’t wanna say more as it’s be identifying and I’m quite regular here.
I’d give it all back if I was well and could dream of seeing my children grow up and do their thing.

Simplestars · 07/11/2025 09:38

Henrysmycat · 07/11/2025 09:18

Two types of aggressive cancer, still not in remission, failing liver from medications and an autoimmune that keeps me in hospital 2-3 days per week. Can’t go even around the corner for holidays as I might need my hospital. My life expectancy is low as well due to all of the above.
I ignored some health signs due to chasing my career and insane amounts of work and stress. I got sick and left everything and can’t even do a few hours of work or even volunteering to get out of the house. I don’t wanna say more as it’s be identifying and I’m quite regular here.
I’d give it all back if I was well and could dream of seeing my children grow up and do their thing.

I'm sorry.

deste · 07/11/2025 10:02

My son and DIL invest in Bitcoin. Fly first class everywhere, my DIL flies half way round the world for a weekend to get her hair cut with a private car taking her the 3 hours from the airport and back. They use a private chef and have on occasion used a private jet.

if they go out for lunch think nothing of buying an expensive bottle of
champagne.

They have invested money for their siblings but dont throw their money about and never use social media.

Im very happy for them, they have no children but have a nephew and niece who will “want for nothing” .

Dyra · 07/11/2025 10:08

Believing in my dreams a bit too much and destroying my job prospects for nearly 25 years as a result.

Long story short, I was rejected from Medicine which did a number on my mental health. Turns out excelling at school without trying and inattentive parents gives you zero resilience and does not prepare you for the life's realities. Effectively gave up on my A-levels. Somehow still did okay, so opted to study Biology instead with the end goal of the graduate Medicine course. Realised about halfway through that the first year was entirely self funded. Something I could never ever afford, even back then when the fees were just over 3k a year. Somehow managed to "pass" with a third (which is basically worthless). Graduated straight into the 2008 recession and couldn't get a job. My already fragile mental health disintegrated into a depression that then lasted for the best part of a decade. Finally managed to get a band 2 post where the most I've managed to do is move sideways into another band 2 role a little over 11 years.

The sole upside of all this is that I met my now husband in this period and we have two wonderful kids. I'm (finally) looking to retrain next year and (finally) kick start an actual career that isn't minimum or living wage

But if I'd just thought taken some time to think, had some honest advice (rather than none at all), or taken a gap year or something; maybe, just maybe I would have built a career in that time and not lost out on hundreds of thousands of pounds of earnings and built a far better pension pot.

pottylolly · 07/11/2025 10:09

Reading these stories I am so, so glad I’ve taken every opportunity I had available to me. We always regret the things we don’t do.

Smallorveryfaraway · 07/11/2025 11:14

I wish I'd just stopped and planned when younger rather than hustling to fix short term problems. I would've chosen a different degree course which would've set me on a different career path. Can't afford to stop and retrain now, can't afford to start again at the bottom.
Secondly, really wish I hadn't stuck with my employer for so many years when I knew full well the most sensible thing to do is switch jobs every two to three years. I've let my career prospects shrivel and am about to be made redundant. Very concerned about my ability to get another job anywhere near the same salary level. Gutted.

kgfreo · 07/11/2025 12:34

What's for you won't pass you by.
That quote always settles me when I think of past "Could have, Would have, Should haves".

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