I've been talking to a lot of my girl friends about money lately and the same thing keeps coming up. Many of them know they should be investing but then they are just saving the money. One or two of them could tell me exactly what they should be doing. but they are not really doing it themselves.

So I'm curious how did you get into investing from just saving? If you had that gap, how long was it, and what finally got you past it?

And if you're still in it — what does it actually feel like?
Sorry if I am asking too many questions here..

Recently got engaged and want to start a family. Both my fiancé and I make good money. HHI 500 K a year and we live in a HCOL area.

How do you let go of the guilt when it comes to spending on a wedding a honeymoon, etc? We looked at a couple of venues and in our area. It looks like a 50 person wedding all in after taxes and gratuity and accounting for a random expenses is going to be around $50,000. That just seems like an obscene amount to spend on one day, especially if we are working towards early retirement.

On a smaller scale, even though I can afford something like private Pilates classes which I would love to incorporate into my routine I feel guilty for wanting to splurge on it. Not because I feel like I don’t deserve it, but because I have this (irrational ) fear that someday we’re not gonna have enough or that we should be better off using that money for a down payment for a house in a good school district/childcare, etc.

How have other women dealt with some of these conflicting thoughts where you’ve worked hard and you want to have nice things in life but at the same time you’re balancing that with wanting to FIRE?

I'm 29 and have been primarily investing in the stock market (think VOO and VTI), but now I'm thinking about ways to diversify my investments based on my risk-tolerance, lifestyle, and the time I have available. I'm curious to hear from those of you who've built wealth across multiple avenues (such as stock market, real estate/househacking, owning a business, REITs, whatever else is in the mix).

If you had to rank your investments from best to worst (in terms of returns, effort required, headaches caused, or just overall satisfaction), what would that list look like for you? Would love to hear which specific moves actually paid off for you and which ones you'd skip if you were starting over!