I've read on it a bit but wouldn't say I'm any sort of expert. I do have a good friend who's more or less ran that path since I've known him dating back to 2008 and he's a few years older than me and set to stop working at 50 (he's 45 now) and I've definitely leaned on him for some advice, along with his personal financial advisor.
Based on your previous post (#159), you seem to be following the FIRE (financial independence, retire early) philosophy. I'm trying to do the same.
The theory behind FIRE is simple (so simple, in fact, that it probably seems mundane). Essentially, you're trying to build a large enough nest egg so that, at a certain point, you can retire and live off of your portfolio. It doesn't mean that you
have to stop working. But you wouldn't need to work, if you didn't want to.
You only need to figure out two things - how much money you want to spend each year, and how quickly you want to draw down your portfolio. There have been a number of academic studies on the second point. If you plan to withdraw 4% of your portfolio each year, it's highly improbable (but
not impossible) that you'd outlive your nest egg. In other words - if you want to spend $60K annually, if you have a $1.5M portfolio, it's unlikely that you'll deplete your funds during your lifetime. (Obviously the $60K spending requirement will increase over time due to inflation, but investing in stocks, over the long run, should at least kept pace with inflation). If you realize you're depleting your portfolio too quickly, you either have to reduce your spending and/or get back to work.
In my case - I'm targeting a 0% withdrawal rate. In other words - once I retire, I don't want to ever touch the capital (barring an emergency). I'd want to live 100% off of my investment income. The goal is to leave a seven-figure portfolio behind. After my wife and I die, some of that will go to charity, and some will go to family - I need to revisit the split. Obviously this means I need to build up a much larger nest egg to achieve this.
A nice thing about investment income, at least in Canada - it's taxed at a much lower rate than normal income ie salary. Someone earning $50K in salary in Ontario, in 2023, would pay roughly $10,400 in income tax, along with payroll taxes (CPP and EI). Someone earning $50K in dividends (from public company stocks - the rules are trickier if we're talking about a private company) would pay exactly $600. (This assumes no other sources of income in both examples). That's a 21% effective tax rate vs a 1% effective tax rate - a huge difference. In fact, you could earn $100K in dividends (double!) and still end up paying less in payroll & income tax than someone who earns a $50K salary.
Like I said - the theory behind all this is simple. For most people, their expenses will rise roughly in line with their income. I'm still spending roughly the same amount as I did a decade ago (when I earned one-third of what I'm making now). I definitely indulge more than I used to (for example I spent close to $3K last year to fly to Europe to see a concert - something I never would have considered when I was younger). But, for the most part, I try not to have too much "lifestyle inflation". I've never been interested in having a big house or a fancy car (even though now I can afford these, if I wanted). In fact, I've been driving the same car since 2010 - my income has increased fourfold since then. I like hiking, playing guitar, reading, watching hockey, seeing concerts - most of which are inexpensive hobbies. You need to strike a balance (nobody should work 80 hours a week, or deny themselves any life experiences for the chance to save up and retire at 40 - you can still get hit by a bus tomorrow). But trying to save half of your raises tends to be a good approach (that way, you build a nest egg, while still getting to enjoy some of the benefits of a higher salary).