How late in your career did you take a gamble on change ?

Apologies, long term lurker and don't post often but I'd love to hear other's experiences.

Aged 44, I've been a Private Investor for fourteen years. Investing has given me a good lifestyle, however at a cost, mentally, emotionally. I've nearly given up many times, my style is stressful and it's isolating being behind screens all day.
I'm not at a point where I can stop and maintain the same living standard. Three more years and I could be close to that figure but I'm not sure I have three left. I have a couple of business ideas but fear is pushing me to stay and secure myself better first. Even if successful it'd be a few years before I could draw anything decent from a new business.

- Did you burn out in your job / sell a business and take a gamble on something new later in your career ?

- Or did you take early 'retirement' from a higher to lower paying job and adjust your living standards ?

- Am I just suffering from 'the grass is greener' and running your own company, managing staff etc is just as / more stressful - but perhaps more rewarding and opportunity to grow ?

Can you reduce the amount of work you do in investing? And move your time into building a different business?

I'm 53 later this year and am changing jobs. I start a new role next month. I cannot stand working for my current employer anymore. Too much incompetent people there.

I looked at how much longer I could tolerate it against my re-sale value and time spent before I retired. I think I'm making the best choice I have done in years.

I switched from a PAYE job in IT to self-employed clockmaker aged 52, taking a decent voluntary redundancy package.
I had already paid off the mortgage, and had been repairing clocks as a sideline for 10+ years, so not a massive leap in the dark.

Thanks for the replies. On paper three more years to get to a better NAV make sense, just in practice not so much.

To reply to some comments-
- Unfortunately my investing style requires me to be in front of the screens from 07.30-16.35. I’ve tried reducing hours but I can’t really.
- Employment I’m definitely cautious about. I have friends with businesses and a constant stress seems to be finding decent people.
@anotherusername I have a fair idea of what I'd like and a number that requires. My kids are nigh on adults and I know my passions and where I’d like to be to enjoy those.
@clockworks I've been thinking along these lines, should I start as an evening sideline and see if there's any traction. I prefer to be fully committed to something but I'd have to get over that.
@Steve H A key question I keep asking myself is the same 'How much better will it pay later and how long might that take' - therefore the earlier you start the better - if you believe.

I would say that early 40s to early 50s is the optimal time to be starting out on your own or making big career changes.

All things being equal, you retain the physical and mental capacity to get stuck in, do the hard-yards and posses sufficient enthusiasm and ambition to maintain this. Plus, you have experience; not necessarily of your chosen field but of how the world and people work. There is risk but hopefully, you'll be a fair way through the mortgage and have a handy financial cushion. You may need take a temporary step back on the more lavish aspects of your life but they will return sooner than you imagine.

And.... should it not pan out as you expected, you are still young enough to bounce back.

Between 2005 and 2019, I had a quarter share in the company that employed me. It did OK but with the other director due to retire in 2019, I started to think about something a little different. A perfect storm of Brexit, Covid and a reclaimed R&D Tax Credit forced my hand. I set up a brand new business entirely on my own in January 2020, a week before my 53rd birthday. I have't looked back since. I'm working harder than I ever have but have never enjoyed work as much as I am now and financially am in better shape than I've ever been.

More than one person has asked if I wish I'd done it years ago. The answer to this is no. If I'd done it earlier, I don't think I would be able to be doing what I am now.

It sounds to me that you are in your perfect storm right now so give it a go!

I started my second career in my mid 40s so not decrying it at all but I found that it has to enthuse you enormously to overcome the energy you had in your 20s/30s.

I suppose I'm a 'private investor' too - but it's a big engine at low rpm that chonks out enough for me to live on and the rest, on average, goes up.

What doesn't fit in your description is that you should be getting richer - and then you can either do less or move to lower risk stuff. Basically taking your foot off the gas. Or do all your gains get taken in overheads etc? If so can you spend less and get a more relaxed life that way? Or do you mean you invest for a client and take a salary?

@Simpo Yep my NAV increases each year, of course each one is different. I'm not your standard buy/hold style and it's that I'm exhausted with.

@Panamax An investor in shares, mainly UK Stocks. My annual ROI would be an outlier compared to most due to my method, size and is relative to the risk, drawdown, time that entails. It's much more hands on.

I definitely won't continue past a further three years, thats 100%. The decision I'm making is whether I grind out some more to achieve a higher NAV and better financial security before I take the leap and new risks.
That's why I was interested in what others have done and how it worked out for them.