Should I jump ship from a job I dislike, but that's cushy and well-paid?

[fell-like-rain]

Currently, I'm a software engineer. I have done adequately at this as a career (about six years so far), but I don't really enjoy it. I would say my main issues are that the work is too abstract, making it hard for me to maintain motivation, and that I tend to go through cycles of procrastination. I get stuck on a problem, avoid working on it, feel progressively more down on myself as time goes by, then finish the work in a mad rush at deadline. I have had a variety of jobs at very different companies, and they all end up feeling the same- tolerable, but slowly grinding me down. I would say my main goals for a career change are to have work that's more immediate/in the moment, as well as having a clearer impact.

An idea I'm batting around is becoming a computer science teacher at the local high school. There's an open role currently, and my teacher friend who works there says they're pretty eager to hire folks, especially in STEM. I've spent a few years volunteering in high schools and with nonprofit orgs that work with teens, and I've talked with said teacher friend about the ups and downs, so I believe I have a clear sense of what I would be getting myself into. I also enjoy doing extended backpacking trips and the like, so the summers off would be very nice.

The stumbling block is that my current job is a. highly paid, and b. fairly cushy. I work 35ish hours/week, with 3 days WFH and 2 in-office, and the work is not taxing- plenty of time to do laundry, etc, during days at home. Especially as a first-year teacher, I'd definitely be working both harder and for longer. On the money side, I now make about $165k and would go down to $62k (getting this from the district's salary schedule). That's plenty enough to live on, as my expenses average $28k per year, but I'd only be saving around $25k instead of ~$93k.

My liquid net worth is about $400k currently. If I was planning to FIRE, I'd want about $700k. However, I don't think early retirement would be good for me, emotionally speaking, and I'd be perfectly happy to work another decade or two if I liked my job. So I don't need more money for any particular goals, but it is hard to step away from a firehose of cash.

So, to summarize...

Pros of switching:
(Hopefully) work that I enjoy more
Summers off for adventures
Carpe f*cking diem

Cons of switching:
Work will likely be significantly harder (and less flexible)
Pay much decreased
Possible unknown issues, e.g. I struggle with classroom management or can't stand admin/parent BS


Thoughts?

[oneday]

So, you're kind of describing a CoastFI situation, which is what I'm looking at for myself in the near future. So that's a vote for "do it!" If you don't like it, you can switch again.

[NV Teacher]

You ready for an honest opinion?  Do not go into teaching.  I started in 1989 and next year will be my last.  Teaching is nothing like it was even ten years ago.  Don’t get me wrong, teaching the kids is great.  If I could just teach I’d stay a few more years but the politics, the micromanaging, and the foolishness have made a once honorable and valued career almost unbearable.  Ask a few of the 330,000 teachers that have left the profession in the last five years and see what they say. The vast majority of schools are understaffed so the extra work is passed onto everyone else.  We didn’t have custodians for months.  Guess who was vacuuming and mopping floors, cleaning the bathrooms, and hauling trash to the dumpsters.  Check and see what the requirements are for getting a state license.  In my state you can get a job with a BS in almost any subject but while you are teaching full time you will be required to get a MS in education within three years.

[former player]

If that $400k net worth is in index funds then congratulations, your future retirement is already funded.  Now all you need to do is work enough to keep body and soul together, and as an educated, capable person you are unlikely to ever be short of options. 

Several years of volunteering in high schools and with teens is a pretty strong indicator that that is where you like spending your time.  I think you have very little to lose by trying out as a teacher, and a lot to gain - your present mode of work does not sound psychologically healthy for any length of time.

NV teacher is right about the disadvantages currently in teaching: I heard exactly the same from a recently retired teacher yesterday, here in the UK.  But things change, society's values change, there's no reason why conditions (and pay) for teachers shouldn't get better in due course rather than continue getting worse.  It's the future, which means no-one knows.

Good luck whatever you decide.

[Laura33]

The stumbling block is that my current job is a. highly paid, and b. fairly cushy. I work 35ish hours/week, with 3 days WFH and 2 in-office, and the work is not taxing- plenty of time to do laundry, etc, during days at home. Especially as a first-year teacher, I'd definitely be working both harder and for longer. On the money side, I now make about $165k and would go down to $62k (getting this from the district's salary schedule). That's plenty enough to live on, as my expenses average $28k per year, but I'd only be saving around $25k instead of ~$93k.

My liquid net worth is about $400k currently. If I was planning to FIRE, I'd want about $700k.

1.  Your spidey sense is telling you that you'd do better in a role that involves you with helping people on a daily basis.  Since you are already spending time doing that without getting paid, it's reasonable to see if you'd enjoy getting paid for it.  (That's no guarantee, of course -- there's a significant risk that turning a hobby into a career sucks the joy out of it.  But it's a good starting point).

2.  It's great to work 35 hrs a week.  But how many of those other unpaid hours are you spending trying to force yourself to work and getting down on yourself for not doing it?  I totally get it, btw -- I share your procrastination problem.  And IME, the anxiety and frustration that goes along with not being able to force yourself to engage can take over a disproportionate part of your non-working life.

3.  The potential new job pays enough to cover your current needs and wants, gives you summers to travel, and costs you $60-$65K/yr in savings.  How much is it worth to actually enjoy your life? 

4.  If you are worried about making the jump, what about working as an adjunct professor at a local community college to see if you still enjoy teaching when you're doing it on a daily basis?  If you're working 35 hrs/week, you have plenty of free time to try that for a semester or two.  It might also give you a sense of whether you prefer teaching kids vs. pending adults, as those are two very different things.

4.a.  And who knows, maybe the pressure of having that extra set of deadlines will push you to be more efficient with your time in your main job.  At least, that works for me -- the busier I am, the more I am able to get done in a shorter amount of time. 

5.  You currently have $400K saved, and you need about $700K in today's dollars.  If your investments average 4% above inflation, then your current 'stache will get you where you need in 18 years, assuming you don't add another cent.  So you are already on track to FIRE -- and you can substantially cut that time by adding even that $25K/yr you mention you'd have left over.  You've already said you'd be happy to work another decade or two if you enjoyed your job.  If that's actually true and not just something you tell yourself, then the new job certainly meets your financial requirements.

5.a.  And some public teaching positions come with a pension option that could further help (as a new hire, you'd likely not get the older, more generous option, but your expenses are low enough that even a few thousand a year could help significantly). 

[c-kat]

If you continue to save 93K a year and get 7% gains in the market you are only 2.4 years from your FI goal of 700K.  Only you know if you can work at your present job that long without it affecting your health, but if you could, you'd then be able to do anything you want. You could try teaching and quit if it doesn't work out and try something else.

A good friend of mine taught for years and hated each year more than the last. She finally quit and is the happiest she's ever been. It is a tough profession. However, that doesn't mean that you won't enjoy it. But if you're already FI you'll be fine either way.

[GilesMM]

If you love teaching, go for it.  Your current job sounds terrible.

[brandon1827]

My wife taught for 13 years. Echoing the sentiments of NV Teacher, it is so much more than just teaching and interacting with kids. You often take work home with you at nights and on the weekends, you very often are required to perform duties that have nothing to do with teaching, red tape is bountiful and ever-present, parent interaction can be extremely difficult and stressful, and the list goes on and on. My wife said a thousand times that if it was just teaching and being with the kids her job would've been great. It's all the other stuff (which will ultimately be the majority of your work) that makes it a terrible profession to be in. Constant cuts by federal/state government, being expected to continually do more with less, and very little support anywhere can make it a soul-sucking nightmare. I wish you the best of luck in making a decision. I would kill to make what you make and be able to work from home a few days per week. To someone like me, what you'd be giving up seems like a dream...but you have to do what you feel is best.

[JAYSLOL]

I would say my main issues are that the work is too abstract, making it hard for me to maintain motivation, and that I tend to go through cycles of procrastination. I get stuck on a problem, avoid working on it, feel progressively more down on myself as time goes by, then finish the work in a mad rush at deadline.

Dang, are we the same person?  This definitely describes how I struggle, sometimes with work, sometimes other areas of my life.  Anyway, I’d kill for a job that paid $160k and I only had to work 35 hours a week.  I’m making like 55 and half the year I have to work crazy hours.  If it were me I’d stick it out to at least hit the FIRE number which should only take 2-3 years, then jump into teaching or whatever as a retirement hobby.  It’s teaching, they’ll be just as desperate to hire in 2 or 3 years, and it might feel a lot less like a job if the money doesn’t matter. 

[oneday]

@fell-like-rain if you take the advice of JAYSLOL, be on the lookout for signs of burnout. You mention being slowly ground down, and that is exactly the path you don't want to get to the end of. The hard thing is that it happens slowly, so can be hard to detect when you've gone to far.

[mistymoney]

This is just cautious me, but with a high savings rate and cushy job, I would work the extra 2.5ish years to get to your fire number, then try teaching. A lot of people end up leaving teaching in a hurry and how will your procrastination work in marking homework and grading tests? Accountability to young ones being much less than a manager, et al.

During that 2.5 years - really focus on your life outside of work. Make it everything you want it to be. Then try teaching in a really low-risk situation because you have your fire number banked.

[GhostSaver]

I work in a kind of data analytics role (and your complaints about procrastinating and lack of engagement sound familiar) and my wife is a STEM teacher at an elementary school. So maybe my perspective is worthwhile.

I would stay in your current job and put away more of a stash for a couple years. I'm having a beer and a burger at my local watering hole after a bike ride right now. I'll be back on Teams/Slack/whatever in 20 minutes and no one will give a shit that I took a long lunch, especially because I had my phone on me. As much as the work can be tedious at times, this kind of freedom would be hard to let go. My wife neeeever has this kind of freedom during the school year. It's really helpful with my kids and with my sanity.

The flip side of the coin is that she gets summers off. The benefits for teaching can make salary understate total comp quite a bit depending on your state and district. And being an elementary school STEM teacher lets her duck some of the standardized tests and take-home grading, though she still puts in a fuckton of unpaid additional hours.

Anyhow, I like the idea of teaching as a community college adjunct for a year as an eye-opener. That could be an eye-opener in one direction or another.

The other suggestion Imhave is to try to tackle the procrastination or lack of engagement directly for a year. Talk to a therapist, try some new strategies in managing your workflow, etc. That might really make a difference in your happiness and satisfaction, and you'll bank another year's savings in that time. The option to go teach won't evaporate in that time.

Good luck! This is a nice choice to have.



Sent from my Pixel 6a using Tapatalk

[MrGreen]

I would say my main issues are that the work is too abstract, making it hard for me to maintain motivation, and that I tend to go through cycles of procrastination. I get stuck on a problem, avoid working on it, feel progressively more down on myself as time goes by, then finish the work in a mad rush at deadline.

This is how is was with software engineering for me. Burnout hit hard for me at the end. I survived 12 years in the profession but for the last three I was routinely bleeding PTO because I couldn't stand to be in the office 40 hours a week. Now FIREd for six years, I don't know if I can say I should have done something different because it got me to FIRE. However, I also had no idea what I would do alternatively and that fear, coupled with the high income, kept me from making a move. If you think your skills would easily allow you to go back to engineering in a year or two if teaching doesn't work out I'd say it sounds like a reasonable move. If you think you might struggle to be hired somewhere, that's a much harder decision.

[fell-like-rain]

@NV Teacher  @c-kat  @brandon1827

I appreciate the perspective on the state of teaching- it's definitely something that gives me pause. I don't think I would even be considering doing this if I didn't have a friend who works at this school to talk to. She definitely brought up some issues similar to what you all have mentioned, but doesn't sound like they rise to the same level of severity here. (It's a relatively well-resourced district in a state that values public education, which helps.) But I will certainly be keeping all this at the top of my mind.


@Mr. Green  @JAYSLOL  @GhostSaver  @mistymoney

Yeah, the temptation to just stick it out a while longer is real. I waffle back and forth between "you did this for six years, what's another couple?" vs "when are you going to take charge of your life and make a positive change?" I agree that staying would be, in many ways, the most sensible option- it's not like this job is killing me, I just feel pretty blah about it. There's a balance here between financial security and personal happiness, and I'm trying to find out where it starts to tip.


@GilesMM  @Laura33  @oneday  @former player

Thanks for the vote of confidence that this isn't a totally stupid idea. It actually crystallized in a very sudden way several months ago- out of the blue, a friend said to me, "Oh, you would make a good teacher", which idea I pooh-poohed at first. But then they pointed out that literally all of my volunteering is with teens and kids, and that I had spent hours and hours teaching them bike maintenance recently- oh, and that I was an undergrad TA for 3.5 out of 4 years of my bachelor's, which I have long cited as the best job I ever had. So it does feel like a well-trodden path, but with a big leap of faith at the end. But sometimes you gotta take leaps!

[jnw]

Try and find a way to enjoy the job perhaps?  Market is really overvalued right now and working & getting lots more money sounds like a good idea right now to me.. putting away as much as possible.

[MrGreen]

I ended up giving myself an ultimatum. I knew that I disliked the job enough that it would eventually kill my soul. So I gave myself a drop dead date, just in case I kept hanging around because the money was great and I couldn't bring myself to quit with nothing else on the horizon. I told myself that so many years was enough and that I knew it gave me a good start, but I wasn't going to become one of those middle aged men I saw who was clearly unhappy but felt like it was too late to do anything about it. Ironically, I found MMM after I'd already set my date and after finding this place and crunching the numbers I realized we were closer than I thought so I was able to FIRE instead of needing to look for the next thing. I'm glad I had my ultimatum though. I needed it psychologically.

[Laura33]

Thanks for the vote of confidence that this isn't a totally stupid idea. It actually crystallized in a very sudden way several months ago- out of the blue, a friend said to me, "Oh, you would make a good teacher", which idea I pooh-poohed at first. But then they pointed out that literally all of my volunteering is with teens and kids, and that I had spent hours and hours teaching them bike maintenance recently- oh, and that I was an undergrad TA for 3.5 out of 4 years of my bachelor's, which I have long cited as the best job I ever had. So it does feel like a well-trodden path, but with a big leap of faith at the end. But sometimes you gotta take leaps!

Isn't it nice when the universe speaks clearly enough that you can actually hear it? 

And isn't it even nicer that all your boring work and high savings so far has put you in a position where you can make the change without blinking if you decide you want to? 

I feel like I should be having a margarita for you or something.  (Or maybe you're just a convenient excuse)

[Metalcat]

There are TONS of careers where you can work with kids, and working with kids pretty much always involves teaching them.

I would explore those thoroughly before committing to teaching. I literally *just* yesterday was talking to my sister who is in the exact same position. She has a 6 figure job that she doesn't like, her specific position that she actually loves is getting eliminated and the positions left that she can have, she hates.

She was talking about becoming a teacher and I freaked and insisted she do something else. Her vision of what teaching is like is just NOT accurate.

Look into all of jobs that work with kids. Think expansively about this, and don't limit your thinking to teaching.

FTR, I worked with kids for decades in a volunteer and part time capacity. I worked in shelters, I tutored, I worked in camps, and was a children's science entertainer for awhile, which was my best job with kids ever.

Then I became a medical professional and I had to stop working with kids despite the fact that I loved it, because dealing with parents is FUCKING MISERABLE.

To this day I would love to work with kids, but not if I have to deal with their parents in any kind of significant way about anything serious.

I would rather be punched in the face. Daily.

[VanillaGorilla]

Have you considered retraining yourself to enjoy your current role more? I think most developers have struggled with what you describe - particularly the frustration accompanying low productivity. I've left jobs because I had nothing to do for months on end and ended up deeply unhappy. That experience actually drove my motivation to FI.

I switched to a small company with a much faster pace and have really enjoyed it. Switching from a large group to a team of one made my contributions critical, and the motivation of not wanting to let other teams down actually improved my state of mind tremendously. A few years and bit more maturity later, I've broken through my procrastination barriers and now promptly start new work items when I have a lull.

You could also be a bit more proactive about getting help from your manager or senior colleagues - when you're stuck or struggling to get going, reach out and ask for help. Pair program on a problem rather than avoiding it. or ask a colleague if you can use them as a responsive rubber duck (google rubber ducky debugging if you haven't heard of it). Tell your scrum master to hold you accountable on a daily basis rather than every two weeks. Your position is likely not particularly unique, and your colleagues might already have recognized your patterns and might be motivated to help.

Of course you can always look for a new job that suits you better, but recognize that any job is going to have challenges and parts that you don't naturally enjoy. Your current role has a lot of perks - 3 days WFH, good pay, good benefits, and doesn't sound like too much work if you regularly procrastinate for days.

[neo von retorch]

Currently, I'm a software engineer. ... I would say my main issues are that the work is too abstract, making it hard for me to maintain motivation, and that I tend to go through cycles of procrastination. I get stuck on a problem, avoid working on it, feel progressively more down on myself as time goes by, then finish the work in a mad rush at deadline.

...
Thoughts?

I've been writing code for money for checks watch 24 years. For sure, some of my favorites (at times) were very "non-abstract" stuff like when I worked on the web site and contest applications for a global chocolate brand, or even just web sites for companies that I'd drive past on the way home from work.

Another favorite was a sort of fleet management / car insurance company, and I worked in a basement. Go figure. But in this case, the people on the floor above me used the software, felt the pain of slow performance or the frustration of bugs, and I met with them personally, fixed their problems faster than they could believe, and got direct appreciation for my efforts. That position was good for other reasons - the team lead handled a lot of process automation that made it possible for me to focus / zero in on a problem area, get my hands dirty, go through the rapid feedback cycle, and fix things. But that lead also gave me a long leash. Sometimes problems were super clear and well-described, sometimes much less so, but I had the autonomy to figure out how to tackle the issues. My brain was on at work, and that was enjoyable.

A less favorable position was one where I was considered "junior", and the project was software-as-a-service, and I was given very small chunks, told how to write them, and the code reviews would nit pick until my code looked exactly how the "senior" dev would've written it themselves. Basically I was a cog in a machine doing abstract work, but having to do it in a very precise way. No autonomy. No way to relate to the bigger picture. Not even really any way to work on my skills.

I've hinted at it, but Daniel Pink writes about this in Drive - skilled knowledge workers tend to find flow and motivation in Autonomy, Mastery, and Purpose (or relatedness). It sounds like the positions you've been in haven't included room for one or more of those, especially relating to the big picture and feeling like there's purpose. Certainly teaching has an apparent purpose, directly affecting the educational outcomes of children and young adults. Presumably you can work on improving your teaching skills and work towards mastery, but I do wonder what the feedback loop is like for a teacher. You don't get to run experiments on children and see how they react to different teaching techniques. Their grades might reflect more on their own skills and interests. And children might tell you if they like you as a teacher or not, but can they give you detailed critiques? And can your peers or supervisors without seeing you in action? I don't know. Autonomy likely varies a good bit depending on teaching scenario. Can you write the curriculum, or your approach to teaching it?

Overall, I hope this is food for thought.

[sonofsven]

Currently, I'm a software engineer. I have done adequately at this as a career (about six years so far), but I don't really enjoy it. I would say my main issues are that the work is too abstract, making it hard for me to maintain motivation, and that I tend to go through cycles of procrastination. I get stuck on a problem, avoid working on it, feel progressively more down on myself as time goes by, then finish the work in a mad rush at deadline. I have had a variety of jobs at very different companies, and they all end up feeling the same- tolerable, but slowly grinding me down. I would say my main goals for a career change are to have work that's more immediate/in the moment, as well as having a clearer impact.

An idea I'm batting around is becoming a computer science teacher at the local high school. There's an open role currently, and my teacher friend who works there says they're pretty eager to hire folks, especially in STEM. I've spent a few years volunteering in high schools and with nonprofit orgs that work with teens, and I've talked with said teacher friend about the ups and downs, so I believe I have a clear sense of what I would be getting myself into. I also enjoy doing extended backpacking trips and the like, so the summers off would be very nice.

The stumbling block is that my current job is a. highly paid, and b. fairly cushy. I work 35ish hours/week, with 3 days WFH and 2 in-office, and the work is not taxing- plenty of time to do laundry, etc, during days at home. Especially as a first-year teacher, I'd definitely be working both harder and for longer. On the money side, I now make about $165k and would go down to $62k (getting this from the district's salary schedule). That's plenty enough to live on, as my expenses average $28k per year, but I'd only be saving around $25k instead of ~$93k.

My liquid net worth is about $400k currently. If I was planning to FIRE, I'd want about $700k. However, I don't think early retirement would be good for me, emotionally speaking, and I'd be perfectly happy to work another decade or two if I liked my job. So I don't need more money for any particular goals, but it is hard to step away from a firehose of cash.

So, to summarize...

Pros of switching:
(Hopefully) work that I enjoy more
Summers off for adventures
Carpe f*cking diem

Cons of switching:
Work will likely be significantly harder (and less flexible)
Pay much decreased
Possible unknown issues, e.g. I struggle with classroom management or can't stand admin/parent BS


Thoughts?

Have you taken a vacation recently? A good one where you do exactly what you want, where you want, with who you want?

[zolotiyeruki]

I've been in a sort-of-similar situation.  I took a 25% pay cut to jump to a job with a shorter commute and more interesting work.  It was a fantastic jump for me any my family, but I wouldn't recommend the same for you.  I was a lot younger, with a lot fewer assets and a much longer expected career path.

Here's my vote:  suck it up, find a way to enjoy your job more, and stick it out for a few more years.  At that point, you're free to pursue whatever future you want.  Roughly speaking, every year you stick at your current job accelerates your retirement date by 2-3 years.

I know several people who are or have been teachers, and all the complaints you've seen mentioned are very, very real.  It doesn't matter if it's in "a state that values education."  You'd still have to deal with all the garbage.

Try and find a way to enjoy the job perhaps?  Market is really overvalued right now and working & getting lots more money sounds like a good idea right now to me.. putting away as much as possible.

^^^ This.  You have a lot of flexibility to control your working conditions.  Instead of giving up on your current job, take some time to brainstorm ideas for making your job more enjoyable.  Start by recognizing that it's called "work" for a reason, and adjust your expectations accordingly.  Figure out your triggers for procrastination, and work out how you can overcome them.  I often struggle with procrastination and inertia, and find it helpful to identify what the sticking point is.  For me, it's often simply a matter of getting started.  Once I've started, it's easy to keep going.

And the feeling of having all your work done and cleaned up and your to-do list decluttered is amazingly liberating.  For me, that's a carrot I can use to generate some motivation and momentum.

[marbles4]

I made a similar move almost two years ago. I had an extremely cushy and boring high-paying finance job in which I'd worked for over 10 years, and quit abruptly to take a middle school math teaching job making less than a third of my prior salary. I was already financially set and I wanted to make a difference in the lives of kids. I also started down the road of concurrent teacher licensure requirements, which was no small undertaking. Also had a 10 and 7 year old at the time...

Wow. I was not prepared for what a teaching career looked like and a first-year teacher trying to fulfill licensure at that. (In addition to the obligations of raising my own family). I was immediately chastened and nearly had a nervous breakdown from the workload / stress.

I didn't even last the first semester.

I ended up retiring - at least for now. Instead, I volunteer in the local school tutoring math to kids who struggle in that subject. I love it and it scratches my itch to make a difference in the lives of kids without having to sacrifice every free moment of my life.

This isn't to say you shouldn't give it a try. I tell everyone that if I'd never gone down the path myself, I would never have known what it was like. Your outcome could be totally different, but wanted to share my experience.

[CrustyBadger]

Your two job choices could not be more diametrically opposed.

I've been teaching for 21 years and have *just* cracked the 6 figure salary barrier. At year 22 my pay will be $117,000, and that's only because I added a MA degree plus an additional 60 graduate credits to my resume AND this is a pretty well paying school district, all things considered. And that's a teaching job where you have no options to WFH, no daily flexibility to even take a phone call or easily take an hour off here or there; and a lot of variables and oversight from higher up that can make your life miserable if you are in a bad school.

I do love teaching, and I think it's a great option for someone who enjoys it, but there are a lot of drawbacks. Sure, the summer vacation is wonderful, but it is unpaid - teachers either don't get paid for those weeks, or the district withholds about 15% of each paycheck for our "Summer Pay" find.  If you have children it is great to have federal holidays and spring breaks schedule that line up with their schedules as well, but that's a small thing and not relevant if you don't have kids.

I wonder if there are jobs you could be qualified for, maybe in an education field, that would allow more time off, even without pay, for one or two summers so you can get that backpacking trip in? Or take leave without pay in Sept/Oct for 6 weeks so you can have some extended travel time? I just can't imagine leaving a job that pays $165,000 and has easy, flexible working conditions, until you are actually ready to retire.

Another thought I had was whether you might have any thoughts you could be ADHD? Some of the things you mentioned can be symptoms of it. I was finally diagnosed a couple years ago and started taking medication, and I noticed a lot of my procrastination disappeared as a result. With ADHD I think people get reinforcement from having discrete tasks that get accomplished quickly (you get a little ding of satisfaction that can keep you motivated) and without those immediate reinforcers you can lose momentum and focus. Just something I wanted to mention.

[Dreamer40]

I kept my sort-of-cushy well-paid job then rage-retired when I was 40. I lasted as long as I could and now I’m free. I thought I would have more interest in a “fun/rewarding” hobby job afterwards but it turns out that work kind of sucks and it’s more satisfying to not do it.

So I would stay put and keep aggressively growing your stash.

[FIRE 20/20]

Two things strike me about your posts.  First, it seems like you know what you want to do and are looking for permission.  If you know what you want to do and if doing what you want won't screw up what you have then I would make the leap.  It seems pretty clear that you really want to try being a teacher and you have enough insight into the plusses and minuses to make a reasonable decision. 
The other thing that strikes me is that you said "I don't think early retirement would be good for me, emotionally speaking, and I'd be perfectly happy to work another decade or two if I liked my job."  With $400k saved and expenses of $28k / year, you only need to bring in a very small amount of income each year, and you said you want to keep doing something. 

These are just a few examples, but imagine you make the jump and after a year or two of teaching you absolutely hate it.  You could find another job as a developer and turn the firehose of money back on.  You should need less than $10k in income each year, so you could work part-time as a bike mechanic (you mention that you taught kids this in an earlier post), you could be a tutor for individual students taking C.S. at the high school or local college.  My local library has a youth coordinator who works with the math tutors, D&D club, arts groups, and the the 3D printing lab - something like that might be available near you (even part-time). 

The point is that with significant financial assets, multiple skills, a desire to keep doing something productive, and low expenses, you have far more options that just staying where you are or being a teacher long-term.  I don't see much harm in giving it a shot and seeing what happens.  If you love it - great!  If you hate it - there are a plethora of options for someone in your position. 

[Villanelle]

This probably sounds a bit "back in my day", but... I think teaching in schools is different than it was back in my day, and in almost entirely not-good-for-teachers ways.  My friends who teach--who are leaving their jobs in droves--seem to spend more time dealing with IEPs and disruptive children who can't be dealt with in any meaningful ways than they do teaching.  And the expectations for outside-school work, which were always significant, have become almost crushing.  I wouldn't touch a traditional teaching job with a ten foot stick of chalk.

Have you considered being a childrens' librarian instead?  Lots of room for creativity--more than most public school teaching jobs--and much less parental interaction.  You'd likely need an MLIS degree though, in order to be a full librarian, but there may be para-professional library jobs.  I was heavily involved with volunteering at a library and creating summer reading program challenges, displays, book recommendations, science projects, and more was incredibly fun and rewarding.  While I was a volunteer, this kind of thing is mostly done by paid staff.  (Which also brings up the point that you may be able to get the reward you are looking for from a volunteer position, which is the ultimate in flexibility.)

If your dream is truly to be a teacher, go for it.  But make sure you want all of the reality of that job, not just the rewarding parts or the parts you immediately think of that don't include the other stuff. 

[NV Teacher]

This probably sounds a bit "back in my day", but... I think teaching in schools is different than it was back in my day, and in almost entirely not-good-for-teachers ways.  My friends who teach--who are leaving their jobs in droves--seem to spend more time dealing with IEPs and disruptive children who can't be dealt with in any meaningful ways than they do teaching.  And the expectations for outside-school work, which were always significant, have become almost crushing.  I wouldn't touch a traditional teaching job with a ten foot stick of chalk.

If your dream is truly to be a teacher, go for it.  But make sure you want all of the reality of that job, not just the rewarding parts or the parts you immediately think of that don't include the other stuff.

You speak the truth.  Too many of my job responsibilities don’t focus on teaching at all.  I have always been able to balance the “extra” stuff that I am required to do with my teaching duties and have been fairly happy.  About five years ago that balance shifted dramatically.  It seems like the “extras” now consume more of my time, efforts, and energy than the actual task of teaching does.  Then you add in the political climate towards education that currently exists in this country and it’s becoming increasingly unsustainable.  My district is going to start the new year with about 1500 unfilled classroom positions.  That’s roughly 35,000 students without a licensed teacher in the room.  I read somewhere that there isn’t really a teacher shortage in this country, but that the current culture in education has made it so unpalatable that the people who were willing to work in education are no longer willing to do so.

[CrustyBadger]

The job of a high school (I'm presuming?) Computer Science teacher might have less pressure than other teaching positions. It's probably not a tested subject (except if you teach AP) and probably isn't required for high school graduation, so I think there would be a lot less scrutiny on things like grading, homework assignments, and even documentation for IEPs as long as you provided the required accommodations for classwork and homework assignments. But if administration decides to move you into teaching Algebra 1, that might be a different story.

[Metalcat]

IDK, it was a long time ago, but we had tons of tests in programming class.

[GhostSaver]

IDK, it was a long time ago, but we had tons of tests in programming class.

Standardized tests from the state? When people in education refer to "testing" these days, that's generally what they mean. It has truly gotten out-of-hand in the US in the past 10-20 years.

My early elementary kids spend, conservatively, 1-2 weeks of classroom time on those tests every year. Teacher performance is evaluated using the kids' test scores so you'd better pray you don't get a classroom full of chucklefucks for two years in a row.

Sent from my Pixel 6a using Tapatalk

[NV Teacher]

IDK, it was a long time ago, but we had tons of tests in programming class.

Standardized tests from the state? When people in education refer to "testing" these days, that's generally what they mean. It has truly gotten out-of-hand in the US in the past 10-20 years.

My early elementary kids spend, conservatively, 1-2 weeks of classroom time on those tests every year. Teacher performance is evaluated using the kids' test scores so you'd better pray you don't get a classroom full of chucklefucks for two years in a row.

Testing has most certainly gotten out of hand..  Here are some that my district/state requires.

MAP - given three times a year in reading, math, and science.  Each test takes 60-90 minutes.
WIDA - given once a year to all second language students in reading, listening, speaking, and writing.  Each test takes 30-60 minutes.
SBAC - given once a year in reading, math, and science.  Each test takes 60-120 minutes.
AIMSweb - benchmark tests given three times a year in fluency, comprehension, math concepts, and computation.
AIMSweb - progress monitoring tests given every week, every two weeks, or every four weeks depending on the data collection requirements.

And don’t forget the end of unit tests for the core subject areas and the assessments required for the computer programs the district has purchased and requires students to use on a daily/weekly schedule.

It seems that we just go from one testing window to the next throughout the entire school year.

[Wolfpack Mustachian]

And of course the class time used for preparation for the big end of course tests and the fact that if there is class time after the big tests, it's pointless to try to get anything accomplished because all parties involved realize that anything else is essentially pointless from any accountability standpoint.

[Metalcat]

IDK, it was a long time ago, but we had tons of tests in programming class.

Standardized tests from the state? When people in education refer to "testing" these days, that's generally what they mean. It has truly gotten out-of-hand in the US in the past 10-20 years.

My early elementary kids spend, conservatively, 1-2 weeks of classroom time on those tests every year. Teacher performance is evaluated using the kids' test scores so you'd better pray you don't get a classroom full of chucklefucks for two years in a row.

Sent from my Pixel 6a using Tapatalk

Thanks for the clarification. I'm in Canada, so that's not at all what "testing" means to me.

[CrustyBadger]

IDK, it was a long time ago, but we had tons of tests in programming class.

Sorry, yes, of course there will be classroom tests and final exams in a Computer Science class, and projects to grade.

I was using teacher shorthand for either 1) state mandated tests of minimal competency required for graduation or 2) state mandated tests to show school ratings on certain subjects (generally English, Math, and maybe Science, possibly other subjects. Usually Computer Science is seen as an elective; I don't think there are many states that include passing a CS class as a graduation requirement.

It's often considered lower pressure and stress to teach in a non "high stakes testing" subject or grade.

[Verdure]

I lean toward the go for it camp, and a couple of years ago when my DH was in a theoretically cushy job with great benefits but was deeply unhappy I encouraged him to quit and take a part-time job in a helping profession that he finds deeply rewarding. After 14 months it transitioned to a full time position and it has turned out to be a hugely positive move for him and us. (Happy spouse, happy house).

But if you don’t feel ready to take the leap, may I suggest a middle road? A lot of posters have suggested sticking it out with your current job until you reach FIRE, and a couple of posters have mentioned the challenges of trying to fulfill the education requirements for licensing while in the first year of teaching. Have you thought about pursuing that while staying in your current job? I don’t know the requirements for your state, but for instance, could you start working on a masters in education now while still working your current job, which is lot fewer hours than you’d likely do as a first year teacher.

You might feel more satisfied with sticking it out for a bit knowing you are making positive steps towards your goal, and it could make the transition easier if you don’t have to take classes while you’re starting out. You’d also start out with a larger support network having made connections in the field through your classes. And kind of moot if you’re FIRE, but you’d probably start at a higher rate of pay if you are already certified.

Also, I gotta say this immediately struck me too when I read your post. My ADHDer spider senses were tingling. :-)

Another thought I had was whether you might have any thoughts you could be ADHD? Some of the things you mentioned can be symptoms of it. I was finally diagnosed a couple years ago and started taking medication, and I noticed a lot of my procrastination disappeared as a result. With ADHD I think people get reinforcement from having discrete tasks that get accomplished quickly (you get a little ding of satisfaction that can keep you motivated) and without those immediate reinforcers you can lose momentum and focus. Just something I wanted to mention.

if you think that might be possible, it’s worth looking into bc more tools (whether meds or not)  to deal with it could help either in your current job or as you go through the massive transition to a new career.

Finally, a bit to say on this: 

Have you considered being a childrens' librarian instead?  Lots of room for creativity--more than most public school teaching jobs--and much less parental interaction.  You'd likely need an MLIS degree though, in order to be a full librarian, but there may be para-professional library jobs.  I was heavily involved with volunteering at a library and creating summer reading program challenges, displays, book recommendations, science projects, and more was incredibly fun and rewarding.  While I was a volunteer, this kind of thing is mostly done by paid staff.  (Which also brings up the point that you may be able to get the reward you are looking for from a volunteer position, which is the ultimate in flexibility.)

I am a public librarian and I deeply love my job, but people are also leaving our profession in droves, I think Villanelle’s point that you may enjoy being a volunteer more than having a paying position is an excellent one, but turning towards librarianship to avoid the downsides of teaching, particularly to avoid parental interaction, could be out of the frying pan into the fire. However, if you achieve FI, then your options to pursue fulfilling work aren’t limited to paid positions, and if you find teaching isn’t the right fit, you have endless volunteer, part-time, and underpaying options.