What to Expect When You're Quitting Your Career
January 22, 2022 8:18 AM   Subscribe

I'm ready to bail from my decades-long career in software design and do something I love for the ~7 years until retirement. I imagine that means a retail job, like in a bookstore. That means, most obviously, a big cut in pay. What can I expect and what should I plan for?

I've been unhappy with my career for a while now and this seems a good time to quit and do something I like for a while.

I'm not old enough to retire yet, but I have a bunch of money in savings. Enough to live on, my financial advisor assures me, if I also pick up some work.

So I plan to find something fun until I'm eligible for retirement. I expect it will be a retail gig, making probably 1/3 of my current hourly rate, part-time. I'm not looking for ideas for a new job. I have a whole list of those.

This is a big change for someone who's change-averse so I need to understand what's going to happen. This is how I expect my life to change:
- I'll have to spend less and pay closer attention to my bank balance.
- I'll have to find my own medical insurance.
- I'll be commuting to the workplace; no more WFH. (So my car might need more maintenance.)
- I'll probably need more than one part-time job.
- ummm... What else? What other changes will I see? What do I need to do before making the jump?
posted by booth to Work & Money (30 answers total) 18 users marked this as a favorite
 
The book Designing Your Life is based on a college course for those just starting their lives, but it has lots of good advice for life changes at all ages! (They also have a work version now). One really good piece of advice I've learned from this book is to "prototype" any life changes you plan on making before you jump all in. Based on this idea, I would recommend getting a weekend job at a bookstore before you quit your job. It may be a lot at once but after a couple of shifts you will probably know if that's what you want to do.
posted by beyond_pink at 8:31 AM on January 22, 2022 [11 favorites]


Pay is one thing, but our jobs have a much bigger impact on our lives than just pay.

You may experience a big loss of autonomy and self-determination on the job, from being able to use your judgement about how to solve problems to deciding when to go to the bathroom. The upside is that you can leave work at work, but it is good to realize there is a trade-off for that.

People may treat you differently. A lot of our status with others comes from our jobs, and if your job moves from something moderate status like software development to lower status like retail you could see some changes in the level of respect and attention people give you. This is obviously not everyone, and some people have a harder time with this change than others. Software development in particular is one of those occupations that is assumed to signify intelligence (especially to those who don’t do it haha), so you may experience a shift in how smart people think you are.

If you’ve never worked in retail or it has been decades, you might try it first. It has been a solid 25 years since I did it and I wouldn’t characterize it as “fun”.
posted by jeoc at 8:35 AM on January 22, 2022 [50 favorites]


You may experience a big loss of autonomy and self-determination on the job, from being able to use your judgement about how to solve problems to deciding when to go to the bathroom.

Or what shifts you get scheduled for when, and with how much notice.
posted by deludingmyself at 8:37 AM on January 22, 2022 [19 favorites]


The other thing that I will add is that juggling multiple part time retail jobs with commutes sounds very stressful. If you were doing things you actually loved like teaching some yoga, focusing on a jewelry-making business, selling art, pet sitting, etc this would probably be more fulfilling.
posted by jeoc at 8:39 AM on January 22, 2022 [7 favorites]


Working retail will likely mean working with more people in a superficial way, rather than working closely with a regular group. This can be very isolating if, like me, your primary mode of meeting people is through your job.
posted by SPrintF at 8:40 AM on January 22, 2022 [1 favorite]


Sometimes you change your life in a radical way, and then your life isn't radically different.

You change careers, and the same stresses and office politics follow you, even if you no longer work in an office.

You change cities, but it doesn't take long for it to feel like the old city.

You lose weight, gain weight, get married, get divorced, and so forth, and...I dunno. It's not the lightning bolt you'd imagined.

So I think you need to reconsider your expectations.
posted by champers at 8:52 AM on January 22, 2022 [5 favorites]


I'm not old enough to retire yet, but I have a bunch of money in savings. Enough to live on, my financial advisor assures me, if I also pick up some work.

This statement concerns me. You should be able to make this statement confidently without relying on your financial advisor and vague statements like "a bunch of money".

Your financial advisor is always incentivized to make your portfolio seem larger than it is and your chances of using it to subsidize/pay for your life to be higher than they are. If they don't, they seem incompetent and unable to deliver promised growth in the portfolio. In addition, they risk you going to a different financial advisor that has "the secret" to provide you with the lifestyle you want from the assets you have. Most prominently, the risks of failure are radically skewed between you and the advisor. If the advisor fails, they still get paid by you, and at most they lose one client (out of many clients). In the extremum where they lose their job, they go find another one. If you fail, you get paid by no one, and you lose the life you're looking for. After a certain amount of time away from software, you may find it quite difficult to return to software due to having an outdated skillset.

I'm ready to bail from my decades-long career in software design [...] I expect it will be a retail gig, making probably 1/3 of my current hourly rate, part-time.

This statement also concerns me. Average total compensation for a software engineer in the USA is about $122K - that's about $58/hour (with generally pretty good benefits). Average retail work is about $11/hour (with generally pretty poor benefits). This is going to be more like 1/5th to 1/6th your current compensation.

What else?

You may find that few places will hire you. I've known a couple people in engineering who decide to move into lower paying work and find that places are surprisingly unwilling to hire them even when employers are desperate for new employees. Decreasing someone's compensation (in general, even if not for you) by 80%+ tends to result in boredom and very quick turnover. Develop a story as to why you're looking to work somewhere, and why you won't just be leaving after a week or two.

You will also open the door to a large number of tax minimization techniques. These should be mentioned to you by your financial advisor, but at the very minimum, look up capital gains harvesting and Roth conversion ladders. If you do this, you will likely reduce your taxable income significantly, which pulls down your tax bracket. It can be advantageous for you to take advantage of tax preferences to low income folks to reduce the tax liability on your broader portfolio.
posted by saeculorum at 8:56 AM on January 22, 2022 [20 favorites]


I'm not old enough to retire yet, but I have a bunch of money in savings

Have you considered buying a little house that you could rent out (or a duplex or something like that where you could live in one side and rent out the other)? Depending on your location, this might be a reasonable way to make enough to live on without needing a retail job.

I worked in a bookstore in college and it remains my favorite job to date, though the experience might have been unique (independent store and not a chain, large group of employees who all were friends, etc). It paid next to nothing. One good step might be figuring out what you would likely make in retail, and then experimenting with that budget for a month while you still have your current job, so you know what the adjustment would be like.
posted by pinochiette at 9:03 AM on January 22, 2022 [9 favorites]


You may find that few places will hire you.

Yeah, I came here to say the same thing - it seems you might be overestimating how easy it will be to get a job. Yes, there are jobs out there, but that bookstore job? That's actually a rather plum retail job that can be competitive, and would rather hire a fresh-out-of-college English lit major. You're more likely to end up at a big chain store like Target, which is definitely not fun and going to come with all sorts of rules and regulations that you get with big corporations. Plus much more risk of COVID.
posted by coffeecat at 9:03 AM on January 22, 2022 [12 favorites]


So here are some downsides to working retail:

It's much much harder to schedule social outings and shopping, because you're going to be scheduled for all the hours you and your office job having friends set aside for that. ESPECIALLY if you're just part time. Part time often means you're at the bottom of the pecking order when it comes to picking shift times/etc.

Be sure to clarify what part time means hours wise, because it's super easy to end up working way more than a full time job working two part time jobs. OH and both jobs will think they're more important, so scheduling conflicts are going to happen and everyone's going to be mad at you.

Speaking of scheduling, do you have a lot of necessary appointments? Because scheduling those just became a lot more difficult.

There's all sorts of things you probably take for granted working from the office, like getting to take a break when you need it rather than on a schedule, having down time, etc. that you definitely will not have anymore.

You're probably not imagining a big enough cut in pay.

You don't get to be in a bad mood. No really, imagine your worst day at work, then imagine having to spend that whole day also dealing with people where the expectation is that no matter how shitty they are to you, you will smile and tell them to have a nice day, and mean it.

You're likely to be very tired at the end of a full shift. Like more than you'd think, so prepare to a good chunk of your off hours to just sort of mindlessly recovering. It's a tough job, especially as you get older.

So upsides:

Depending on the business chatting with the customers about something you're passionate about can be awesome.

IF you somehow manage to get on at a cool niche shop (my favorite place to work sold bird watching/feeding supplies) a lot of the downsides can be lessened, but the pay's probably worse , there's even some popular hobby shops where they expect you to "volunteer" first for an indefinite to make sure you know what you're doing. and there's no guarantee that just because the owner has the same hobby as you that they'll treat you like a human. At least there's company policies with bigger chains.

Oh and 7 years or so is probably just enough time to work your way up experience wise from "please take me" to being picky about what jobs you'll take.

Um.... those three are what I got, and they're all pretty qualified and depend on getting lucky and finding the right place to work.

Yeah, working retail sucks, even at fun hobby shops.

But hey, I don't know you or your list of possible careers, or anything like that. It's just that anyone describing retail work as "fun" really makes me wonder if they know what they're really in for.
posted by Gygesringtone at 9:05 AM on January 22, 2022 [16 favorites]


You may find that few places will hire you.

My wife is trying to do this now. She does not want to go back to the stress of daycare management, and can't get a call back to be a part-time preschool teacher or a retail gig. Everybody assumes she won't stick with it, I guess.
posted by COD at 9:07 AM on January 22, 2022 [1 favorite]


I am currently working in a bookstore for minimum wage! I have not retired, but have considered this a sabbatical. One of my coworkers did retire from his career and is doing this for fun and socialization. So I definitely have thoughts.

- If you have had a sedentary job, you are about to discover that you are Not Prepared to stand all day. Invest in good shoes and maybe cushioned insoles, and expect to spend the first month hopping directly into an epsom salt bath after work. (This mostly passed, for me, but my feet still hurt a whole lot of the time.)
- Get ready to spend all your time among people very much younger than you! This is my current favorite part - most of my coworkers are just-out-of-college early-20s kids, and they are delightful. But I really had to spend a while being consciously warm and unthreatening, and reining in my typically-filthy mind, so as not to come off as creepy or inappropriate, and I still have to be careful about giving unsolicited advice or behaving like I understand their lives because I was 23 once, too.
- It's probably a good idea to decide up front what your level of investment is going to be - do you want to move up the chain a little, have some responsibility? My experience has been that retail is so desperately understaffed in general right now that an experienced adult can put themself on that path , but retail also sucks as a career and if you're just looking for something low-stress, there's nothing wrong with just doing a simple job well.
- I dunno about you, but six months in, I'm ready to go back to my career. I have enjoyed this but I'm now pretty bored. If I were in a better financial position, I might look more closely at using my professional skillset in a part-time sort of way for minimal pay for a nonprofit. This is not to say "don't bother with retail," but you may find it's not how you want to spend the rest of your working years, and that's fine!

On preview, my experience has been 2-3 day callbacks and instant hiring - retail is so fucking understaffed right now - but of course YMMV. And I am genuinely having fun! It's much easier to have fun when your boss needs you much more than you need them.
posted by restless_nomad at 9:07 AM on January 22, 2022 [21 favorites]


(A caveat to that last bit, now that I think of it, is I got this job in the hiring ramp-up to the holidays and we are now in post-holiday austerity, so that may be very different.)
posted by restless_nomad at 9:09 AM on January 22, 2022 [2 favorites]


The advice I would give someone I care about is to wait til the pandemic is over.
posted by bleep at 10:01 AM on January 22, 2022 [12 favorites]


I worked in bookstores for years. It's work. It can be physically demanding, lifting heavy books and magazines. You are expected to be working all the time in a way that salaried workers don't typically experience. Lunches and breaks are tightly timed. Customers can be idiotic, rude, annoying, and they are ever-present. Customer will bring their small children, who will make incredible messes that can include pooping in the magazines. Not joking. You have to be 100% polite, calm and ignore their bad behaviors. There's a lot of drudgery and more stress than you think.

That said, bookstores are one of the best places to be. Readers are more interesting. When you sell books, you see trends as they are developing. You get some free books, esp. if the managers are nice. And your fellow booksellers are some of the smartest and funniest people you'll ever know.

It will feel bad to make a lot less money. Dealing with crappy health insurance is really horrible.

You have valuable skills. You could do part-time contract work. You could find a cool non-profit to work for. A change in environment can be great. See if you can get a very part-time retail job and see how it feels to you.
posted by theora55 at 10:43 AM on January 22, 2022 [9 favorites]


I know two people who are semi-retired and who work part-time at Home Depot. Both report it as a positive experience. One started at $14/hour (southern US).

I also know a retired teacher who works part time at an early morning school program. She loves it, gets to deal with the kids, with none of the burdens being in charge.

Just a few examples...
posted by rhonzo at 11:15 AM on January 22, 2022 [2 favorites]


My dad's retirement gig is driving a limo for a private company. The owner is a buddy of his, so this may not apply to every limo driving job out there, but he is able to pick up work when he wants or if he's got other plans he doesn't have to. He mostly works on weekends, but not every weekend. He lives in a small town about an hour away from two different airports, so a lot of his work is taking people to the airport or picking someone up.

He also picks up a lot of wedding-related gigs. He brings something to read while he sits in the parking lot waiting, or he makes phone calls. More than once he's been invited in to the rehearsal dinner/reception to eat, for free. He's a gregarious dude and free is his favorite price, so he's accepted and had himself a good time. He's 76 and has been doing this for several years now.
posted by Serene Empress Dork at 11:34 AM on January 22, 2022 [6 favorites]


I'm ready to bail from my decades-long career in software design and do something I love for the ~7 years until retirement.

Excellent!

I imagine that means a retail job, like in a bookstore.

Wait, what? Of all choices, how did you settle on this? First, what book store? Around me, they've all disappeared.

So many other possibilities. Myself, I left software after three decades and had a very successful second career as an ESL teacher. But dealing with bitchy customers? Now? No, thanks -‌- that's why I went back to school, after dropping out of college so long ago -‌- so I'd never have to do that again. As Shannon Wheeler asked in Too Much Coffee Man, "Would you rather work retail or have a nail driven through your hand?"
posted by Rash at 12:23 PM on January 22, 2022 [3 favorites]


Response by poster: I love you all. These replies are exactly what I needed. A couple further comments:
- I worked in a small bookstore briefly, between jobs probably 20 years ago. I loved it even though I didn't much like the owner. Everything else about it was great. And I worked on an as-needed basis at a small Oriental Carpet shop. So my retail experiences were all pretty positive. I figure my best retail hope is some small niche-y joint: book stores (we have a handful here), music stores (I think there's still a couple left), tea shops, etc. I might like working one of the many microbreweries around here, learning how to make great beer.
- I like the idea of taking a sabbatical of some sort. Then I could then take a class or do the "prototype" thing.
- I taught as an adjunct a few times but I never felt I was very good at it. And that caused stresses that I'd like to avoid. I never wanted to have my own business, but maybe there's something there...
posted by booth at 12:43 PM on January 22, 2022 [1 favorite]


- I'll have to find my own medical insurance.

I can guarantee you that unless you know someone who has non-employer-provided insurance right now, that this is twice as expensive as you're imagining and covers has as much, with higher copays and coinsurance. If you've gotten used to employer provided insurance that is at all good, this is going to be a shock.

If your employer current pays into a retirement plan for you (even just a trickle), make sure that your financial advisor has allowed for that change in your retirement savings.

The one person I knew who did this successfully many years ago went from radio broadcasting to the day shift a Domino's where I was an assistant manager. He was THE day driver, T-F (he played golf on Mondays) and I have no idea who he knew that he finagled that shift. But man, pizza is a hard way to make a living, even if you're the day driver; there's something about cornmeal in your hair...

I've a friend who is a manager at a big chain bookstore, and she got literally threatened just last week because they wouldn't open back up five minutes after closing for "just one little thing, please." Even if you've done retail before briefly, it's a lot when it's a long time. And it can be fun, any job can be fun. My wife periodically had fun being a jailer. But retail is a lot and it's a skillset like any other job.

In your shoes, I would definitely consider microbrewery before bookstore, though you're not going to get hired straight into brewing (especially as a part time employee) unless you know the owner. Even getting hired behind the bar is going to be a challenge at this point. Worker shortage or not, bartending is a skill, knowing tea and being able to recommend what people are going to like to drink is a skill, etc., and employers can absolutely get someone with experience versus having to train you. When we bought my wife's last set of really nice boots, it wasn't just "here's your boots, have a nice day!" It was "what do you wear, tell me about how you walk, where do you work, let's talk about the instep and toe box on these boots versus these boots."

Do you have any friends who have their own business who'd be willing to take a chance on you? Because that what a retail or food establishment is doing when they're taking on someone whose retail skills are rusty and who probably isn't used to taking orders for a living any more.
posted by joycehealy at 1:03 PM on January 22, 2022 [7 favorites]


I figure my best retail hope is some small niche-y joint: book stores (we have a handful here), music stores (I think there's still a couple left), tea shops, etc. I might like working one of the many microbreweries around here, learning how to make great beer.

Not to belabor a point: but I really think you're falling into the old trap of "What's the hardest job in the world? Mine. What's the easiest? Everyone else's." I REALLY REALLY suggest you do a lot more research. You probably could do an o.k. job at a microbrewery, but not nearly as well or as quickly as the person walking in with a degree in fermentation science from a state school. Did you know that's a thing? That's a thing. On the other hand, a larger regional brewery may actually need someone to help run whatever software they've got keeping everything in place. There's all sorts of software adjacent jobs involving music or books.

So I don't know, the single biggest quality of life improvement I've ever had was when I stopped working retail, and I've had good retail jobs. I think almost everyone I know that's gotten out of retail would agree with that. I can't imagine going back to that if I had experience that I could probably leverage into a nice office job somewhere.
posted by Gygesringtone at 3:13 PM on January 22, 2022 [8 favorites]


I figure my best retail hope is some small niche-y joint

Ok, but those aren't the places that are most likely to be hiring right now, because while the pandemic has been good/fine for essential stores (i.e. groceries, pharmacies) or big stores that can pivot to online, it's been brutal for small businesses that rely on foot traffic. Even if they haven't closed, they are less likely to be hiring - it's unclear if you've actually looked at job ads in your area recently to see what's there, but I'd spend some time doing that first.
posted by coffeecat at 3:59 PM on January 22, 2022 [3 favorites]


Honestly, from what I hear about retail, it's probably a lot worse in so many ways than your software job. Retail workers are treated like complete crap and are frequently abused, and everything everyone said in the thread about pay, insurance, standing, abuse, never having a consistent schedule, etc. I don't think it's going to be "fun" compared to your usual job, most likely. I have a friend who works in a business I'd consider to be "fun" (like people tell me I should work there) and I hear that they haven't been able to hire anyone in literally years because everyone who thinks it' d be "fun" to work there can't take the standing there for hours or moving heavy things and don't want to work weekends. The friend gets off the major legal holidays and that is IT, and they are so short staffed that it's a huge problem if they need a weekend day off.

I'm an office worker who has to do part time service work, which I haaaaaaaaaaate and am terrible at. What I have to deal with is probably cushy compared to a retail worker--my therapist says, "you get the same people screaming at you, except now it's over a sweater." But if there's anything I've learned by answering phones and emails, it's that you're there to take abuse. It's absolutely socially acceptable to abuse a service worker and scream at them and threaten to get them fired, and that can happen more easily in retail than in office jobs with more protection. My coworkers and I have been bitched out and threatened multiple times this week for the silliest of shit, like someone paying $1 when they didn't need to (why did she do this, who knows, but she demanded a refund for days), someone not following the instructions as to how to pay $5 (this is the one who was threatening us and my boss ended up paying something like $100 to shut this one up), someone paying $15 instead of $5 and throwing a shit fit and harassing my coworker when she was told she could get a partial refund...humans are awful. Anything involving money makes people especially crazeballs. The book Twenty-One Truths About Love features a character who hated teaching so he decided to start a bookstore, which is also stressful as fuck and not going well.

Since retail is so disposable, you won't have much in the way of protection from crazeball behavior and you are going to have to shut up and take it and smile, smile, smile. Retail may not be as complicated as programming, but it's probably a different stress instead of less stressful. Unless you read all of this and think "My current job still sounds worse than this," I would beg you not to do it. Seven years left of the hell of software design is probably still easier than abuse in retail.
posted by jenfullmoon at 4:06 PM on January 22, 2022 [4 favorites]


Years ago, back when I worked retail, I'd say that the very best thing about my job was the customers. And the worst thing? The customers. I can't imagine working retail in the middle of a pandemic (or even soon post pandemic). The horrible things I've read about how people are seriously punching down break my heart.
posted by kate4914 at 4:30 PM on January 22, 2022 [1 favorite]


Ideally your financial advisor has given you a year-by-year analysis assuming you retire now and earn an additional $X per year for the next Y years [with a specific number, rather than “pick up some work” - maybe you are being vague on purpose and already have that number], spending $A per year over the next B years and then - if this would change over time - $C per year over the remaining D years of your projected life. This should include the cost of health insurance/health care and taxes on any investment income, and can be adjusted as needed if you foresee more than two future phases.

If not, that is step one. From there, determine specifically what type of job you can get that will make $X/year, and how much you will have to work at that job, and decide if you want to be tied to that. I don’t have suggestions for what that would be or what to consider there, but lots of other people here are answering that part.

Or, if you could retire after 7 more years at 1/3 your salary, could you stand to work for another 2-3 years at your current salary (i.e. current position) and then just fully retire? This might or might not actually work, depending on the various tax issues that saeculorum references above - but your financial advisor should be able to run these scenarios through and determine how long you’d need to keep going at your current job so that you don’t have to depend on retail or other work. You could still do it for fun if you wanted to, but you wouldn’t need to. This might be a better option if you can stand to stay at your current position for a bit longer, since after retirement you could work retail or similar if/when you wanted to, rather than needing to.
posted by 2 cats in the yard at 4:51 PM on January 22, 2022 [2 favorites]


The (surprisingly wholesome by reddit standards) subreddit r/simpleliving may be able to help with advice for this too.

I know someone who left the finance industry to work as a bus driver and is much happier, not discounting your plan at all. Another option to explore (even as a back up) is the option of part time work in your industry where you get to keep some of the benefits of your job (a better salary, having the background knowledge) but it stops being so consuming and distracting from the rest of your life.
posted by hotcoroner at 5:01 PM on January 22, 2022 [3 favorites]


You will hate modern retail and your expensive, ineffective health insurance more than you can possibly imagine.

Don't.

Just don't.

Keep your soul-crushing, well-paying, healthcare providing job another year or two and sock away that extra cash and then retire once you qualify for Medicare. Don't swap it for a soul-crushing crap job with crap pay and no benefits.
posted by ananci at 8:37 PM on January 22, 2022 [6 favorites]


Having worked retail, and now working for an outsourcer who deals with call center folks every day, I also want to say this these “unskilled jobs” are HARD. Not just on your body (as mentioned above), but also they involve skills. Those super niche jobs, like working at a bookstore or tea shop? Those are the more desirable jobs, too, and so people who have put in their time at crappy big box stores and have retail experience are also going to want them more. And, while I’m betting you are great in the field you’re experienced in, you likely are going to be LESS experienced and LESS qualified in this specific field.

Yeah, it’s great having a job where you can leave work at work, but please don’t fall into the trap of thinking that lower paid jobs are throwaway jobs that anyone COULD do, but most people don’t have to do. You’re not overqualified for a retail job, you’re low key under qualified because your only experience sounds like it was decades ago.
posted by itsamermaid at 9:03 PM on January 22, 2022 [4 favorites]


I know this is turning into something like a unanimous pile on but, as someone who worked "specialty" retail (bookstores, cafés, candy shops) for 23 years and only got out just in time to narrowly avoid the pandemic--you don't want to do this. It's gotten so, so much worse out there.

However, if you're dedicated to your plan, work somewhere with carpet. It's grosser when people leak on it (and they will!!) but, seriously, mopping sucks, everyone hates doing it so they'll make the new person do it, and even at just a hair under 40 the last goddamn thing I want to do after standing up and smiling at people all day is slosh around in filthy water. Carpet.

Really, your best bet? Contact a temp agency and work shitty desk jobs until you retire for good. At least there'll be carpet.
posted by Grim Fridge at 10:59 PM on January 22, 2022 [3 favorites]


I have worked retail alongside people in pre-retirement. It seemed to work well for them because it was a congenial, low-stress environment. Retail isn’t necessarily the Lovecraftian nightmare people here are making it out to be (but I do think you should take the warnings seriously). I would caution you not to think of it as “doing what you love” unless retail is what you love. Selling books isn’t the same as reading books.
posted by Comet Bug at 12:22 PM on January 25, 2022


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