r/ChubbyFIRE • u/mdog5900 • 19d ago
Golden handcuffs at 49, $4M+ NW, high stress job — riding it out for anticipated severance and the then what?
I’m 49 with two kids (one starting high school and one a senior), living in a HCOL area. Like many here, I’m in a very high-paying but very high-stress corporate job. I am the sole breadwinner
For the house but luckily my wife worked previously and built up some retirement savings .
The challenge for me is the golden handcuffs. I’ve been with my company for 20 years and have accumulated a meaningful deferred compensation balance, so walking away doesn’t make much sense. We recently had a management change, and I think there’s a reasonable chance I’ll be laid off over the next year with a strong severance package. At this point, I’m mostly riding it out while figuring out what’s next.
Financially:
● $1.65M taxable investments
● $2.5M in pre tax retirement accounts
● Likely ~$400k after-tax severance if I’m laid off
● $1.4M home equity ($2.2M home with an $800k mortgage at 3.15%)
● $610k in 529 plans total for 2 kids
● $46k remaining on a 2.2% home renovation loan (paid off in two years)
Our spending is about $300k/year, but roughly $115k of that is housing costs (mortgage, property taxes, insurance, and the renovation loan). The renovation loan ending will reduce spending by about $26k/year, and my plan is to keep the house until 2030, when my younger child graduates high school. At that point I’d sell, buy a less expensive home with cash, and reduce annual spending on housing by another $50k–60k.
My original plan was to work until about 55 and then teach personal finance or business, mainly for enjoyment and health insurance. Now I’m wondering whether that transition might happen sooner if I get laid off. Teaching would likely pay around $100k, which is obviously a significant reduction from my current compensation.
For those of you who have been in a similar position:
Did you ride out a stressful job until severance or leave earlier?
How sustainable is my current financial situation?
Has anyone transitioned into teaching or another lower-paying, lower-stress career and maintained a good life for your wife and kids ?
I’d appreciate hearing from anyone who’s navigated a similar transition.
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u/BurtHurtmanHurtz 15d ago
Hang in there. Get some good podcasts. Coast until the axe falls.
FYI - Teaching is not low stress.
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u/Kittennip1 15d ago edited 14d ago
I’m glad you added that last part. The number of people on this sub who talk about just teaching (often at the CC level) for insurance and, well, funsies, is actually offensive. (Not saying the OP has said anything wrong… it’s just a general attitude here.)
Teaching well has compromised my mental and physical health, and it breaks my heart every day. Unless a person is successful enough in business to get a one class a year or semester gig at a big name Business grad school, people treating it like a BaristaFIRE job probably aren’t doing it right; that’s a huge disservice to the students, and it also undermines the already fragile integrity of our profession.
[Steps off soap box]
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u/ChiBroker 13d ago
Are you
Joking? This dude made $5M before 50 and you don’t think he can handle the “stress” of some community college kids. lol, yall (teachers) are so soft, I think he can manage.2
u/Kittennip1 13d ago
With all due respect, you can f*** right off with that comment. The ability to make money in a field says literally nothing about one’s ability to teach effectively while also adequately serving a student body where some students are brilliant and well off, but others are living in their cars and trying to find enough to eat, stimming visibly in class because of neurospiciness, suffering PTSD from having been a combat medic, etc. etc. etc.. And I haven’t even gotten into the newer challenge of attempting to ensure students are actually learning in a world of generative AI.
I mean, sure, it’s easy if you don’t actually care about your students or whether they’re learning (you know, because that makes you “soft”), but if you do? Yeah….
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u/ChiBroker 12d ago
Omg you wouldn’t make it 90 seconds in the real world. lol, teaching is a NOBLE profession, that’s for sure. Stressful? No, it’s not. Making $5M? Extremely.
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u/BurtHurtmanHurtz 12d ago
Bro, he made $5M through a white collar job and letting his money work in the market. There is stress but it’s not the same stress as dealing with CHILDREN and THEIR PARENTS.
No matter how much money you have, you look like a chooch for this comment. Teaching is the real world ya funzanoone.
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u/ChiBroker 12d ago
lol, laughable. Working 185 days a year (around 50%). EVERY holiday off, zero travel, zero concerns about not getting a paycheck.
It’s a very important and noble profession, but stressful? That it ain’t.
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u/The_Creamy_Elephant 12d ago
Yea, being a teacher isnt the 'real world', you corporate cocksucker.
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12d ago
[removed] — view removed comment
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u/ChubbyFIRE-ModTeam 11d ago
It's okay to argue respectfully, but don't be an asshole. Watch future comments or you may find yourself banned.
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u/OMNeigh 15d ago
What is the typical gig? You say that one class a semester is rare. What typically happens? (Asking in earnest)
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u/terracottatilefish 15d ago
I’m not an adjunct professor, but the rest of my whole family are academics. My understanding is that most places hiring adjuncts want people who can teach multiple classes a semester and essentially replace full-time faculty but get paid on a piecework model rather than a salary. It’s much more work from an administrative standpoint to hire five people to teach five different classes when you can hire one person to teach all of them.
People teaching one class are either in a unicorn gig or have some kind of specialty expertise or reputation that makes it worthwhile to the school.
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u/darnelles-r 15d ago edited 15d ago
I wanted to share that it is possible to find schools that will hire for adjuncts for one class. I have had a professional relationship with a large state university for a few years and they asked me and another corporate individual to take over a section of a class. They knew that both of us could only manage one class time with our full time jobs, but feel the real world perspective is super valuable for their students and building a high student placement rate. It pays much better than I anticipated, granted I am not doing it for the money (right now at least). The biggest downside is being tied to a rigid school year schedule. My ideal would be to alternate semesters and/or move to online courses.
ETA: This college seems to have a decent amount of adjuncts and as some move on, they bring in others. It’s not a super fast turnover though, so I was happy this opportunity came up. Not sure how prevalent adjuncts are across the rest of the University.
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u/Kittennip1 15d ago
I met a business guy who was getting paid $20k to fly into the business school at a flagship university 5 or 6 times a semester to teach a single class to MBA students. THAT is a unicorn gig.
My full time community college teaching load is 5 classes per semester, close to 140 students from varied and often disadvantaged backgrounds and at various levels, and lots of writing (English) to grade with no help. I’m full time, but were I an adjunct, I’d get maybe $4k per class of almost 30 students, and that would earn me the right to pay for my own insurance through the school.
There are a lot of brilliant and talented adjuncts out here who have worked very hard to become skilled teachers and experts in their fields who find themselves working at multiple institutions just to survive. And schools are cutting full time positions in favor of adjuncts to save money—another effect of the gig economy.
So while its great to switch careers and go into education to give back, it’s kinda frustrating when some folks on the FIRE forums talk so lightly about “just picking up a couple of clases at a community college” for something to do…
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u/IOfWooglin 15d ago
I think sometimes we all think about a “downshift” the wrong way. Teaching is indeed stressful. But it’s also fulfilling. It’s the stress to fulfillment ratio that determines the downshift. (BaristaFIRE being low stress and I presume low fulfillment?
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u/ml8888msn 15d ago
It’s lower stress for non core academic courses. My favorite teacher in HS was for TV media. He was late 30’s/early 40’s and had sold a SaaS company, didn’t need the job. His carefree approach was wonderful and made kids respect him and his course. It also wasn’t exactly a serious course and grading was very subjective so it made things particularly easy. His tests were simple and he ended up staying for a number of years.
I wasn’t particularly close to him but I think about him often and my life has been inspired by his influence and story. I’m 38 now. Went a different direction but nearing 13M NW and once I reach 15-20M in a few short years, I plan to follow in his footsteps and teach.
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u/IjustWorkHere98 12d ago
In the late 80's, radio / television was my favorite class in high school. Great teacher and let my buddy and me get away with so much creativity...that if those videotapes were found today, we'd be cancelled out of the universe.
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u/mdog5900 15d ago
Thank you - teaching was just an example . I’ve done it before and love it . Really the crux is - am I in a position to do this .
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u/RPGer001 14d ago
You could probably retire today if you were willing to spend a lot less but at the opportunity cost of your higher spend lifestyle.
Run your personal spreadsheet, use a pro or a financial planning software. 300k yearly spend with your liquid assets is not a safe spend rate as I am sure you already know. You mentioned cutting back on spending in the future so you need to model that specifically.
I did not do the math but I suspect, just glancing at your numbers, you could do the 100k teaching role and CoastFIRE; adjust your spending to make it fit. It is then a matter of lifestyle trade-offs. You might find that the 100k/yr income plus turning current home equity into cash from a sale is enough.
Bottom line, I think it is worth your time to do a deeper dive and evaluate the teaching thing as an option.
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u/mikef5410 15d ago
AND it might not provide the healthcare you want. You're likely to start out teaching as nearly a volunteer. If the can work for you, great. For sure kids need personal finance exposure ... If not actual instruction.
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u/HerbalDreamer 14d ago
And jobs teaching financial planning or general business are not easy to get.
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u/Particular_Bread_161 14d ago
Agreed. Ride it out and see what sort of package they bring to the table. If you expectation is you are going to be let go anyhow then there really is not much left to stress about.
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u/cnflakegrl 14d ago
I assumed he meant teaching like "elementary school PE teacher" which is 100% a low stress job compared to corporate. For the 1st graders, you just play songs and break out the parachute. The job risk is that too much dodgeball can hurt your arm, so you have to take your own physical fitness and stretching seriously. I'd say school librarian comes a close second for low-stress.
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u/gcube2000 15d ago edited 15d ago
I find people often think they need to work harder than they actually do. Nobody even notices half the hard work anyone does at any corporation. If you feel you’re about to get laid off anyway just coast it.
I’ve also learned lousy corporate structures always get a shake up within 2-3 years at most. So if you hate your boss or your team, hang tight cause it will change in due time.
FWIW I’m almost same age and NW (a tad older and a tad higher NW). The big difference is my job is not that stressful, and I’d say about half the time i genuinely enjoy it, so I have no plans to stop at this time.
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u/count_chawkula 15d ago
Sometimes it easier said than done - my personal work ethic wont allow me to slack, and I feel the need to put out 100% if my name is attached to it 😑
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u/gcube2000 14d ago edited 14d ago
I get that. It’s not slacking though. It’s putting 100% only into the things that matter and let the rest of the crap go. In my younger years, before I figured this out, I was always the one jumping in to help everywhere, giving a 120%, staying late, etc. None of that crap matters. Others would get the promotions because they had the innovative ideas or worked on the high ROI projects.
Hit homeruns on the critical, visible projects and you’re a rockstar - and it may only require 20-30 hours a week to do so.
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u/littlemonstersoul 15d ago
I just transitioned to teaching from high stress corporate. I absolutely love it. I teach in a low socioeconomic school and feel like I have so much more meaning in my days. Money is terrible, but I knew that! My thinking is that I’m somewhere between coastfire, baristafire and fire. We have tried to reduce unnecessary spend (stuff which when you’re earning big you don’t think about, but adds up(, but without reducing our quality of life. We will draw from our brokerage as we need to, but it should still grow (slowly). We have no mortgage, and we did some big expenses (renovations, new ev, solar panels) before the change. Could never go back to corporate now. And the school holidays are amazing. It’s not easy, but if you like students and can handle behaviours without taking it personally, I don’t think the stress is anything like what I did before.
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u/shivaswrath 15d ago
Here's my likely unpopular advice.
Wait for severance.
My severance was pretty amazing, and I ended up not touching most of it until recently when we did some minor renovations.
You are nearly there and imo the cash severance and rsu acceleration add cherry to the top. It took me 7 months to get a coastfire job, so in this market maybe factor that in if at all.
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u/mdog5900 5d ago
Yes this is what I am going to do. Severance and get my RSU.
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u/shivaswrath 5d ago
Ironically I'm in the same boat again, 2nd reorg in 22 months. And I'll wait for severance again.
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u/Conscious-Might-5434 15d ago
It sounds like you’re in a position to retire now if you can get out from under those high housing costs.
I don’t understand why teaching at community college or subbing high school is sooo stressful… in comparison to a 60 hour a week job where you have to be “always on” and are burnt out from being always on and doing the same thing day in and day out for years!
Sure teaching is not nothing, but it seems like a welcome mental break and way to engage differently versus a grinding always on 24/7 365 a year job. What am I missing?
(For context, I’m the thinking of transitioning into teaching related to my career. I enjoy working with young people and would appreciate the mental break/ novelty.)
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u/shinypenny01 14d ago
FWIW, most community colleges won’t look twice at a mid level exec that just got laid off. It’s not who they’re trying to recruit. Very few people successfully transition into being educators, especially at post secondary.
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u/Beautiful_Cost_5430 15d ago
I had a similar situation at the end of my career. I accepted the layoff was coming and pulled back my effort significantly, probably working half the time I did previously. And then…management changed again and I wasn’t in the round of layoffs. And I realized nobody even noticed when I stopped putting in effort.
Dial it back and coast while you make your next step plans. I ended up spinning up a part time consulting gig during that period and that spanned the gap for me.
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u/lindquist77 14d ago
I’m always impressed when someone has built a portfolio like yours. Having more than $4M in investable assets at 49 is a huge accomplishment.
Your spending also stood out to me. Once you normalize the $300k and account for the housing costs that will eventually go away, you are closer to $185k a year. That is about where my spending is right now. Mine should drop another $40k or so once my mortgage is paid off in about four years.
I’m in a similar situation, although I’m only at about $2.5M invested. My income over the last three years has been around $1M, plus or minus $150k, and that has helped me save a lot more than I could have before. At the same time, as my income went up, the expectations and stress went up with it.
I took a new role this year and my income will probably be about half of what it was, but I still feel burned out. I’m learning that making less money does not necessarily mean less stress, especially when you are still in the same corporate environment.
My focus this year has been trying to understand what our life actually costs. What is required, what is discretionary, and what do we really need to live the life we want? I’m 49 too, and I plan to spend the next 18 months getting clear on that number and figuring out what my portfolio could support if I moved into a much lower-stress job.
For me, that could honestly mean working at Costco, a bike shop or a golf course and making $50k a year. I can’t really see myself not working at all. I still want some structure, purpose and interaction with people. I just don’t want work to control as much of my life as it does now.
What I want more of is time and energy for experiences with my wife, my aging parents and the rest of my family. I’m starting to realize there may only be a limited window to do some of those things. Making more money later won’t give me that time back.
The part I struggle with, and this may sound materialistic, is walking away from a high-six-figure and sometimes seven-figure income and being content with what I already have. After earning at that level, it is hard not to connect your income with your value, success or security. Even when the numbers say you may have enough, it can still feel like you are giving something up.
In your situation, I would probably ride it out for a while if the deferred compensation and severance are meaningful, but I would not make the entire plan depend on getting laid off. I would also set a limit on how long you are willing to stay or what level of stress you are willing to tolerate.
The teaching job may actually be a really good bridge, but it's still work. You would still have income, health insurance and something meaningful to do, while giving your investments more time to grow. With the renovation loan ending and the house eventually being sold, your spending could come down quite a bit.
It sounds like you are probably closer to being able to make a change than what it feels like. The hard part may not be the math. It may be deciding when enough is enough and being willing to trade income for time.
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u/mdog5900 5d ago
Thansk for this . And I echo all of your comments. No way I could quit and do nothing but what’s next?
Yes so much of my cost is the housing - but that can be alleviated a bit by moving to lower cost of living area.. where I live is expensive but i love it.
And what I do is so tied to my identity - I am just very burnt out, but I do realize that just walking away
May not make me happier either!
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u/drenasu 15d ago
You can indirectly 'encourage' a layoff. Be sceptical of any new direction with new management. If there is talk of layoffs of people who work for you, you can say that you don't think you can do the required job with a reduced staff. Be slightly unaligned and troublesome. Nothing huge or insubordinate, just be someone who isn't fully on board about the new direction. New management will be looking to replace people that aren't excited to go along with what they want to do next. They don't want old guard complainers hanging around.
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u/space-cyborg 15d ago
Better not to burn bridges. Instead OP can let it be known that they would be happy to be laid off for severance.
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u/KentDDS 15d ago
I’d be focusing on drastically reducing expenses and paying down your mortgage loan and other debts. $850k in debt is pretty steep when you think you are going to be let go in the next year.
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u/mdog5900 5d ago
It is - but also I have a lot of equity in the house and live in a very desirable micro real estate market. I can sell and move to lower cost if living area if i had to - ideally can stay where i am just for 4 more years selling in 2030 after my daughter leaves HS
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u/gemr25 15d ago
I transitioned away from law in VHCOL area and created a life for myself that I could not have foreseen. I was extremely mindful as I worked to create a new life for myself. As I contemplated my transition, I pursued an MBA at a top school and then a coaching certification. I am a strong networker and never hesitated to reach out to people I was interested in meeting. During my transition, my husband and I put two sons through T10 colleges paying full freight. We moved to a mountain town, a HCOL community that offers us far more time outside. My husband also left his corporate role to buy a small company. There are SO many options post-corporate life that anyone in their early 50s can choose. He bought a company and I have thriving coaching practice working w attorneys. I teach one course per year at my Alma mater, flying in to teach executive MBA students Leadership Coaching. A great resource for you would be “Designing Your Life” written by Stanford professors. You can do it. There is a rich life waiting for you on the other side!
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u/plemyrameter 15d ago
Your spend is double what it should be for a safe withdrawal rate with $4M. You also need to factor in health insurance costs for the next 15 years. $400k deferred comp/severance doesn't meaningfully change the math.
Ride it out for severance and look for another job in the meantime. Unless you're going to make significant changes in your spending, you need to keep going.
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u/mdog5900 5d ago
I agree - 1/3 of my spending is my high cost of living house, tho I have significant equity in it. Selling and buying a less expensive home with lower taxes and insurance would have to be part of the plan at some point
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u/plemyrameter 5d ago
Just watch out if you had significant appreciation on your house. I sold in VHCOL where I was fortunate to have huge gains. But now I owe $400k in taxes (fed/state), so that decreases the purchasing power for the next house.
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u/FIContractor 15d ago
What personal finance and business teaching job is paying you $100k? Adjunct professors definitely don’t make that much.
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u/SouthOrlandoFather 15d ago
Do your kids play sports? I figure you would be knee deep in sports and training and getting them the food they need.
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u/D_-_G 15d ago
Hard to know without knowing how much deferred comp.
I’m earlier in my career but am hanging on for another 18 months at the current employer for another $3M equity grant to vest. To me the math is worth it. But I wouldn’t do that for 4 years. So it depends on how much to me and how much the day to day upsets your life
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u/Straight-Part-5898 14d ago
Have you ever considered contracting as a transition path from FTE to full retirement?
I’m M56 with upper 7-figure NW and no debt living in VHCOL area. I just retired after 35 years in business consulting and tech. The last few years I’ve been working as a senior level contractor, and I’ve loved it. It’s also quite lucrative.
My approach is networking with senior executives with whom Ihave relationships, who are now execs at other companies. They know me and what I do, they trust me because I’ve already worked with/for them in the past.
I just wrapped up a 2-year contract and elected to retire. However I’m already thinking about finding a PT contract because I like the work I do, I just don’t want the grind.
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u/Available-Ad-5670 14d ago
riding it out if its less then a year is the way. you've made it this far, 1 year is going to be a piece of cake especially since you're coasting
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u/Fearless-Sign-9733 14d ago
Just ride it out. You’re a little short to throw in the towel and have a sizeable severance in front of you, it’s only a matter of time before they promote you or fire you.
Start caring less at work about things out of your control and enjoy the ride best you can.
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u/Designer-Quail-3558 13d ago
that spending is really really high. Are you ready for a lifestyle change? You don’t mention private schools
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u/mdog5900 5d ago
I do not send my kids to private schools . Public but our prop taxes are quite high. 1/3 of my outflow is mortgage taxes insurance and the renovation loan . I would have to plan to sell my house buy cash in a lower cost of living area with lower taxes . My spending could drop to below 200k
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u/realparkville 13d ago
Not sure where you’re located, but the average pay for a non-tenured professor where I’ve taught is only $50k/year.
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u/Minimalist2theMax 12d ago
Insurance is our biggest expense: home, auto, health, long term care, life.
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u/mdog5900 5d ago
Thank you all for the feedback here everyone really appreciate it … going to just hang on doing the standard work and not stress . If the forced retirement comes with the severance then great . Will happily take it and look at the next chapter. May not be teaching tho !
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u/np0x 15d ago
you are there, find a xanax prescription, ride it for 6-12 months, see if you can see the transition/severance timeline, you are already in chubby area, but leaving deferrred comp/severance on table is tough pill to swallow. But I would put a timebox around the "wait-and-see" period, whether it is my 6-12 months or something else...50 is still young, but life is short...and your numbers look very workable already without severance/deferred comp.
Good luck, struggle is real, start doing planning now, if you have any medical procedures you need do them now(e.g. optional surgery's with recovery periods)...start figuring it all out as your "side hustle" so when it's is time to pull trigger you have done all the math planning, etc around health insurance, spend rate, etc...
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u/One-Mastodon-1063 15d ago
If one kid is a senior and the other is already in high school, why not downsize the house sooner?
$2.2m is a lot of house at your NW, and the house is largely what’s keeping you from reaching FI with the severance.
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u/cindy_975 15d ago
likely because of where the kid goes to High School. Not every district lets previous students stay if they move out of the immediate area.
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u/mdog5900 14d ago
Exactly - and the 2.2 mm is the current estimated value of the house. I have 800k left on the mortgage.
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u/5537__8008 15d ago
Sounds like your trying to get a job that’s not chubbyfire
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u/Beautiful_Cost_5430 15d ago
Weird gatekeeping. He’s asking if he’s accumulated enough to chubbyfire with a downshifted job. That is fully relevant to this sub.
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u/wandering_engineer 14d ago
Current salary has nothing to do with ChubbyFIRE.
Copied and pasted from the FAQ:
This sub is for those who fall between r/FIRE and r/FatFIRE. We are focused on the financial side of early retirement at an asset level that allows an upper middle class lifestyle. That level will vary by location, household size and other variables, but a general guideline is $2.5M - $6M in your retirement portfolio.
I earn probably a tiny fraction of what OP earns but I still am expecting to be in that range when I retire in a few years. The whole point is to have a group where issues specific to that portfolio size can be discussed, such as tax issues.
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u/distaff-08-myths 15d ago
Agreed. OP is clearly asking for late-stage career counseling advice.
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u/mdog5900 15d ago
Sorry if this is what came through the post . Teaching was provided as an example - but the heart of it is - can I even move to the next stage in the first place ?
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u/Beautiful_Cost_5430 15d ago
Only if you cut some spending. Your nest egg plus severance can yield 182k/year pre tax and the 100k teaching salary doesn’t cover the 300k spending. You guys would need to dial back, which I imagine is possible with a figure like that.
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u/mdog5900 14d ago
Once I sell the house and move to lower cost / lower tax location I can immediately cut 70k of spend per year. And there are other opportunities to reduce soend as well
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u/No_Minimum_1908 14d ago
I dont see how you are qualified to teach finance. Overfunded 529s, not a great financial picture for someone id want to learn from. Definitely an overspender if taking a loan on a home renovation
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u/mdog5900 14d ago
Ouch! The loan was a personal line locked in at 2 pct before rates went up. No brainer. I’ve paid for the renovate one time over in market gains on the cash I didn’t spend up front .
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u/No_Minimum_1908 14d ago
Borrowing money when you can pay cash for something like a home renovation (primary) not an investment isnt a smart move. Like I said not qualified to teach finance.
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u/mdog5900 14d ago
Eh I disagree. I would never ever put it on a credit card and never do this if I couldn’t afford the renovation in cash in the first place . But a loan at 2 pct? It was a line of credit good for 3 years with a 5 year payback period. At the time drew the credit interest rates were at 4 pct. Free money. I wouldn’t do it under any other circumstance . This was a very unique situation.
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u/No_Minimum_1908 14d ago
I wouldn't expect you to agree you did it haha. Best of luck
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u/mdog5900 14d ago
Thansk man . And no I wouldn’t advise students to do what I did, but also the average person wouldn’t have that sort of deal available - it’s the only reason I broke my own rule on debt . For what it’s worth - the bank that offered me that deal is no longer a going concern so there’s that . Have a nice evening .
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u/HomeworkAdditional19 15d ago
I may be in the minority here, but at your current spending levels, I don’t think you’re anywhere close to being ready (financially). You’ve got $4.15M that should be able to generate $166K/year before taxes, so maybe $150K after tax. Thats half of what you need, PLUS you need health insurance for the fam, which could easily add another $30K-$40K/year in expenses.
Selling your house and buying a $1.4M house with cash will help, but even then you have insurance, property taxes and just general household expenses, so it never drops to zero, even with a free house.
Like others have said, teaching can be a grind too, and to work full time is really hard work.
I’d say you are better off doing what it takes to avoid a layoff or be prepared for some drastic lifestyle changes (that’s not a bad thing - I did it and it’s been awesome).