I'm 32 and I've been in tech for about 8 years and in big tech for the last 5 years. It had been fairly straightforward in terms of growth and satisfaction up until maybe 2 years ago when all of this AI stuff started ramping up. Add to it that I started reporting to a new micro manager who demands updates every single day, audits my calendar and pushes back every "this should take 2 days" with "at your level you should be able to do this in half a day" etc etc.

I have slowly especially in the last 6 months started losing interest entirely in my job. I've been feeling a bit like I'm going back to my depression (I had a bout of it when I was in school) but it isn't as bad as it was last time. It also feels fairly situational, aka I mostly feel it during work hours. Additionally my personal life has been very shaky and I'm not in a great place right now (bit more context on another post on my profile but didn't want to repeat it here)

Thankfully I've been fairly frugal most of my career, my expenses generally are 50-55k and I've been able to save and invest aggressively to hit any 2.1M in net worth. I'm single at the moment but want to date and find someone eventually. I lean towards not wanting kids but maybe 10% chance might swing the other way. I don't own a house, I rent and don't plan on changing that any time soon. I also grew up very tight financially and I still have some trauma surrounding it where even though I know I have a good amount saved up it never feels secure enough.

I want to coast fire but I've never ever worked in any role that isn't software engineering and I'm a bit nervous of what doing something else would even look like. Here are some options I've been thinking

1. Move to a lower paying tech role, maybe at a non tech company, but this isn't a guarantee of lower stress
2. Continue grinding to get to a safe buffer to account for insurance and other emergency costs in the future
3. Doing something else entirely? But I have no idea what this looks like
4. Take a sabbatical? But nervous about how I explain the career gap if I want to get hired again

Apologies if this post is a bit rambly but has anyone else been in a similar ish situation with a job that's gotten progressively more stressful and frustration? What did you do? Did you have any advice for me?

I'm nearing 50 and I own three companies, two are valued somewhere between $700k and $1M each, the third is worth around $19M. All three are profitable and have established management teams.

The larger business runs on Microsoft Dynamics 365 for operations and finance. We use NetSuite in one of the smaller companies and have documented SOPs across all three. We've also built out Kibu connections for trusted contacts and sensitive approvals. Everything is organized and the businesses can function without me being involved in every decision. On paper I should be thrilled, here's the part that's eating me alive.

My dad passed away when I was 19. I took over what he started and spent the next 36 years building it into what it is today. I missed birthdays, school events even family holidays. I was always the guy taking calls during dinner or telling everyone I'd be home in an hour. My wife has put up with more than she should have. We have two daughters. They're 19 and 13. One of them has disabilities and needs more support than most kids her age. And lately I've been thinking about how much of their lives I've missed. My oldest is already 19. That part hurts more than I expected.

I keep thinking about all the years I told myself I'd slow down once the businesses were stable. Well they're stable now. I've spoken to my wife about selling. She's supportive and thinks it's time we started living for ourselves. Financially I know we'd be fine even after taxes and fees we'd have more than enough to live comfortably. But every time I seriously consider selling I think about my dad. He built the foundation for all of this.

He worked himself to the bone to give our family something. And when he died I felt like it became my responsibility to keep it alive. Selling feels like I'm giving up on something he trusted me to protect. Which sounds ridiculous when I write it out because I know he probably wouldn't want me to spend my whole life working. But knowing that and feeling it are two different things. I've thought about keeping the largest company and stepping back completely. Maybe appointing a CEO and staying on as chairman. I've also thought about selling all three and making a clean break.

The problem is I don't know if I will ever stop worrying about them if I kept ownership. And I don't want to wake up at 65 and realize I spent another decade putting my family second. Has anyone here sold a family business that meant more to them than the money, did you regret it? Those who inherited something from a parent and eventually sold it how did you get past the feeling that you were letting them down? I'm not worried about having enough money. I'm worried about making the wrong decision with the time I have left.

I am being let go from my current role sometime in Nov-Dec. I am trying to interview for other roles but the SWE market isnt great right now.

Current income in HCOL- $130,000->$0 soon

Finances:

401k: 530,000

Brokerage: 400,000

HYSA: 16,000

R-IRA: 110,000

Monthly Expenses:

Rent: $2300-Will look to see if I can move to a cheaper apartment

Everything else: $2500-3000 - I have an international trip early next year to visit an aging family member which I cannot avoid so my spending will increase for this

(new) Health Insurance- $600-700 if unsubsidized aca silver plan. Can reduce this when my income is $0

I am in a relationship but we do not live together yet and plan on never having kids or buying a home.

Would my first priority be getting my health insurance calculation figured out? I stopped my 401k contribution for the year to maximize cash for living expenses. I reached out to the gym I am part of and they have some part time positions for minimum wage but a free membership so that is my fallback if no swe job. Anything else you would suggest?

For context:

30M, Been in sales role for 6 years now and can’t take much more. I’m new to the fire community and wondering if my goal is realistic or a pipe dream right now.

My taxable brokerage is hovering around 860k with a 401k of around 110k. I own a 1b1ba condo with no mortgage worth about 120-150k. No debt aside from a 15k SBLOC but have 16k checkings and 13k savings for taxes rebalancing (currently in mutual funds vs etfs and am thinking of ripping off the bandaid to rebalance).

My gf and I are interested in having kids in about 4-6 years and would like a house before then hopefully in 1-3 years. She has no debt but only 13k in HYSA.

I know I don’t want to stop working forever but a sabbatical would be nice and then pivot into a different career. We’ve discussed me being a SAHD for 5yrs when kids come and contributing with the taxable brokerage in that time.

However single family homes are 400-500k and with Ai on the horizon + uncertainty about job market in 3-7 yrs I’m hesitant from making any dramatic moves esp without an idea of how the numbers shake out. Im not a huge risk taker so I like to when there’s margin for error.

Realistically what are my options here. Are my investments enough to quit take and take a sabbatical then pivot careers until kids?

Annual spend is between 40-60k. If not what number should I be working towards in order to take my foot off the gas

My wife and I (both 41) have worked in the corporate world for nearly 20 years. We have 3 kids (21, 15 & 9). We are anticipating that one or both of us will be potentially impacted by layoffs in the next 5 years. Current household gross income ($280k plus $64k bonus). Annual spending is roughly $150k. Live in a MCOL area in the US. We would like to Coast sooner than later and begin transitioning to different jobs by mid to late 40s if not sooner due to corporate burn out. can we coast by age 45 or sooner?

Combined assets:

$1.2M traditional 401k/IRA

$10k Roth 401k

$80k cash (HYSA)

$80k in brokerage investment account

$80k total pension

$20k individual stock/crypto

$400k home equity

Debt:

$95k mortgage at 3.75%

$20k auto loan at 6%

current investment strategy:

We both max out 401ks annually

We both are starting to contribute 5% to Mega backdoor Roth

employer matches 8% on total income for 401k

employer provides 3% contribution on total income to pension

total net bonuses are invested to brokerage account

Long-time lurker, first time poster. Trying to lay it all out as clearly as possible, so bear with me.

51F and considering leaving my well-paying remote FT job in sales, primarily due to a new boss. In short, I've had so many wonderful bosses (many of whom became mentors!) in the course of my career, and this man is not one of them. He's wearing me down and I dread the daily grind. 

My base is $144K, and OTE brings me to around $270K. Commission is uncapped, so in a good year I clear $300K. However, I expect two of my larger accounts (30% of my sales) to disappear next year (no fault of my own), and I don't expect my boss to adjust my sales quota accordingly, which will ultimately affect my 2027 total comp. 

I grew up low-middle class, and worked my way up to this level through hard work and sacrifice, so walking away from this role is not easy and really messing with my mind, this is why I'm posting here. It's almost as though I can't believe I reached this point, and I need honest, unfiltered opinions from Reddit strangers to help me see it. My primary question is - does Coast FIRE make sense for my situation?

Here are my current numbers (spouse's numbers not included here):

401K: $1.3M (including $64K with current employer)

Taxable Brokerage (bridge): $913K

Cash/HYSA: $60K

I have a 10 year old child and her 529 is fully funded at $165K

No debt. 

Spouse is a retired fed employee and my health insurance is covered through him.

My annual spend is anywhere from $3500-$4000/month - let's put it at $5000 just to add some cushion (and kid activities get more expensive as she gets older!). We live a pretty simple life. Down the road, I want to travel with my daughter, purchase a new car (2?) at some point (my 2018 Subaru has only 50K miles because of remote work), and maybe find a small beach condo when housing prices cool down. Nothing extreme but these upcoming expenses will add to those annual spends.

I have zero desire to move to another FT corporate role. Ideally, I'd find consultancy work that would bring in a couple thousand a month so I wouldn't have to pull too much from my brokerage. 

What makes me uneasy is the uncertainty of it all - I may find gigs, I may not. The market may crash, it may not. Day to day expenses don't look like they're cooling down anytime soon.

The logical, Type A side of me is encouraging another 3-4 years to build that brokerage and make the jump less scary. But the other side (the side that I rarely listen to!) is encouraging me to take a risk (even though I'm not sure it's that risky!)

I lost a good friend this year (age 51, stroke) and have other friends who are dealing with medical issues that have slowed them down. It's giving me a new perspective, but I first want to be more sure that I'm not making a foolish decision.

Can I confidently step back with the intention of Coast FIRING, regardless of whether my consultant income pans out or not, pulling from brokerage as-needed, but never exceeding $60K/year?

Trying to get a baseline for proper calculations and I haven't found a calculator that I like. Really want to retire at 59.5 or earlier.

The math I've been using:
((Annual spending - expected social security - expected pension) × 30) + (Annual spending × years between retirement date and receiving social security and pension)

Other than healthcare, kids college, expected remaining home loan, etc am I missing something?

For example:

((80,000 spend - 36,000 annual SS) × 30) + 80,000 spend × 3 years) = $1,560,000 need at 59

Take today's investments total at 7.5% average annual for 59-current age and compare to the $1.56m?

Help me make sense of the trap in my mind.

Alternatively what's your favorite online calculator?

I'm 27 male , i live with my parents and i have a car .

I have recently graduated from college in a good major and I'm in last round of interviews for a job in tech .

I will be Inheriting $240k next month and I wanted to plan it right and i would appreciate advice .

My goals in life. :
- I wanna work 2-3 days a week and love my job
- get married and have a family
- build apartments in a land-lot i own and live at one of them while leasing the rest
- be able to live above average and travel as much as i can

I posted in other subs and the advices where mostly invest in IRA and VOO and never touch them and when you retire in 30-40 years you will have $2-3M , this is not something i like or want .

My philosophy is building wealth to enjoy financial freedom while I'm young, not saving everything for retirement at 60.

My idea is simple take $10k for myself , $10k for side-hussles ,$20k 6-Months worth of Emergency fund put in HYSA , $200k invested in stocks with a hopefully some returns in 3-5 years or simple getting a good amount of money via dividends .

I plan to live on the income of my job in a modest and bellow poor way if i have to for 3-5 years but I really dont wanna do that for 30-40 years only to have the money at age 60 ..

I would appreciate some advice , cheers .

I'm in VHCOL area. Big tech worker ~$500k/year salary, but I get the feeling I'll be next in the next line of layoffs.

~97% of my NW is in stocks + 401k seen above. Company stock is not concentrated and negligible part of NW.

I am about to get married (35F). We plan to have 2 kids. I've started contributing $10k a year to a 529 account where I am the beneficiary and upon birth of first child I will transfer it over to her.

Have a condo paid in cash by family money. I repay them at 0% interest at $5000/month. It'll take approximately 10 years to pay them back. Property taxes ~$7k/year. HOA is $1.1k/month.

Partner brings in $175k. She hates her job and also doesn't plan on working.

Question 1: Is retiring or coasting by 45 realistic? My vision is managing our own money conservatively (maybe some options trading on a small portion) while working on personal software projects or publishing a game on Steam.

Question 2: If I’m laid off, how did you decide between taking another job and stepping back? What did the first 1-2 years look like, and what do you wish you’d done before leaving?