Successful investors - When did your day job start feeling financially pointless?

I’m at the point where the money I am making by moving money around in the market far overshadows my income from my 9-5. I’m staying at my job because I love it and I like the structure and community at the office—but if it ever got stressful, I would probably just dip.

Does anyone have any stories of when and how they realized their job was a much smaller piece of the pie than their other assets? And what was that transition like?

Ah, the ‘I make more money trading’ euphoria that precedes every correction.

Zen said:
Ah, the ‘I make more money trading’ euphoria that precedes every correction.

Been there, seen that—always feels like you’re a genius right before the market humbles you. 2008 and 2022 taught a lot of people that lesson the hard way.

Zen said:
Ah, the ‘I make more money trading’ euphoria that precedes every correction.

Haha, you’re so right. I’ve been through enough cycles that I’ve seen and felt this before. My best investment has been keeping my job.

I got to the point where I could cover my basic expenses with the 4% rule, but not all my discretionary expenses. Retirement funded, kids’ college funded. Then it all started to feel pointless. A bad day in the market and my year’s salary goes poof. Good day and you make it back. But my job was super stressful.

When you can pay your bills with dividends and interest and mow lawns on the weekends for pocket money, the grind seems pretty pointless, so I quit.

Ended up with a part-time remote position with flexible hours and kept my salary but billed hourly. Win-win. I work enough to fund my retirement accounts and have a few nice-to-haves.

@Sky
Sorry if this is a stupid question, but I’m super curious—what does it mean that you bill hourly if you’re salaried? I’m confused on how this works.

Tan said:
@Sky
Sorry if this is a stupid question, but I’m super curious—what does it mean that you bill hourly if you’re salaried? I’m confused on how this works.

I think he means he makes a similar rate in an unsalaried position.

Tan said:
@Sky
Sorry if this is a stupid question, but I’m super curious—what does it mean that you bill hourly if you’re salaried? I’m confused on how this works.

Yeah, sorry, I didn’t write that very clearly. I work hourly but at the same rate as my salary when I left.

Once my passive income streams became enough to pay my bills and I had enough F-U money to the point where I could go 5 years without having to work if my passive income stopped, I realized I wasn’t in love with my job and walked away.

@Blair
This is the answer—once your passive income reaches the level of your working salary, that’s a pretty good indication you can basically rely on your investments.

See how you feel in a bear market. Then you can consider leaving your job.

We’ve more or less been in a bull for like 13 years. Let me know how you feel when the multi-year downturn happens—or, in other words, don’t quit your day job unless you have multiple millions invested.

@Afton
It sounds like he does have multiple millions (say 2 million and up) if his gains far exceed his income.

Keir said:
@Afton
It sounds like he does have multiple millions (say 2 million and up) if his gains far exceed his income.

People on Reddit are prone to hyperbole.

Wylie said:

Keir said:
@Afton
It sounds like he does have multiple millions (say 2 million and up) if his gains far exceed his income.

People on Reddit are prone to hyperbole.

People on Reddit are also rather reluctant to believe that there are other Redditors who are late 40s or older and are reaching their FIRE goal.

We could have retired early (FIRE) in 2021 but keep working to increase our lifestyle in retirement. We’re also scared to commit and quit our good jobs.

I reached my goal for retirement at 50 if I was single without kids, but I’m married with kids, so I gotta keep working still. Families are expensive! College is 100% sorted out even if they all go to medical school. Retirement is done as long as we don’t have an extended bear market before I retire.

My dad was a co-founder at a VC firm in the dotcom era and retired when he was in his mid-30s for this exact reason (and to be present raising me and my sister). He still was up when the market opened every single day out of habit and passed the years with hobbies like collecting motorcycles, cars, building hardware, etc., and was extremely present in my life growing up. All this seems great on the surface but never seemed to bring him fulfillment, and it showed. Plus, I could always tell when the market was having a good day throughout childhood and adolescence. I’d say stick with the day job for a sense of forward motion and purpose—too much idle time without direction is never great.

Not going to lie—I’m surprised at how few people have stories of becoming independently wealthy on this post.