Quit the 9-5 and go remote?

[PricklyPete]

Have you done it? Has it worked out the way you intended?

A little backstory, I just turned 40 and am doing well in upper/middle management. I actually do enjoy my job for the most part. We live in a medium size city, near decent schools, and generally enjoy it a lot. We are on track for a very comfortable retirement at age ~55 (just about when the last of our 3 kids heads to college).

All of that being said, my heart is living in the mountains and we spend a good amount of time up there. It is always our goal to move there in retirement. My wife has spent several weeks up there this summer with the kids (me doing long weekends). It has got us thinking...why don’t we just live up here. The schools are amazing, really family friendly town, amazing amount of activities for kids of all ages. Some of the best mountain bike trails in the state. Great skiing. Problem...not really job friendly up there. Given that I work in tech, I can go the route of remote work. No one is going to give me a remote VP job...but I imagine I can find some programming jobs. While I have been in management for a while...I have always kept my fingers in the tech (doing POCs, mentoring, personal projects, architecting projects, etc).

Problem is that this will likely be a considerable drop in salary (50% maybe). We should be able to combine the city house and mountain condo assets to buy a house for cash in the mountains...so that releases some financial burden...still thinking retirement will be further off than 55...but not sure if I would care. My wife will probably work a bit once our youngest is in school (2yrs), so that will help some (although I kind of already factored that in with the 55 retirement plan).

Thoughts? Who has done something similar and are you happy with where the path has taken you?

 

[lxskllr]

Dunno, but you should do what makes you happy, and maximum $ ≠ maximum happiness unless you're shallow. You need to figure it out.

 

[Ns1]

if you got comfortable job prospects and don't feel like climbing the corp. ladder anymore, fuck it, go remote and live that life.

 

[ImpulsE69]

I have sort of done that, but I didn't go from management to grunt...I was just a grunt given more freedom. A few things (and there's been a few threads on the whole remote work thing already)...

1. You have to have INSANE amount of initiative and concentration. You can't be the 'babysitter'.
2. Most likely you will be required to travel more than you do now
3. Something that is going on for us right now is we have new upper management that wants face time - so we went from working 100% remotely to our entire group (group not team) is required to be in the office 16 hours a month for 'facetime team building'. This put a staggering damper on my overall plans to travel week to week and they put a freeze on hiring anyone outside of 3 key cities (which is a whole other story). Basically we are bracing ourselves for some major changes of which if they are too many I'll most likely be looking for another place to work.

One major thing is you won't have much face time with your bosses most likely. This may not be an issue depending on your boss and culture. Just keep in mind that you are just another 'remote worker' and your status will really revolve around your ability to sell yourself over a phone or email.

 

[PricklyPete]

I have sort of done that, but I didn't go from management to grunt...I was just a grunt given more freedom. A few things (and there's been a few threads on the whole remote work thing already)...

1. You have to have INSANE amount of initiative and concentration. You can't be the 'babysitter'.
2. Most likely you will be required to travel more than you do now
3. Something that is going on for us right now is we have new upper management that wants face time - so we went from working 100% remotely to our entire group (group not team) is required to be in the office 16 hours a month for 'facetime team building'. This put a staggering damper on my overall plans to travel week to week and they put a freeze on hiring anyone outside of 3 key cities (which is a whole other story). Basically we are bracing ourselves for some major changes of which if they are too many I'll most likely be looking for another place to work.

One major thing is you won't have much face time with your bosses most likely. This may not be an issue depending on your boss and culture. Just keep in mind that you are just another 'remote worker' and your status will really revolve around your ability to sell yourself over a phone or email.

This is a bit of my concern. In a past job, I did a lot of remote work. I would sometimes feel siloed if I didn’t have a fruitful conversation with my boss weekly. This is something I have made sure to do with any remote workers I have had over the years since...trying to connect weekly.

I have zero interest for travel. I have done that before, and just not interested. A company I used to work for would likely jump at the idea of me working for them again...but not sure if they would be ok with minimal travel.

Oddly, the idea of going remote feels less liberating at some level than being in a city like Denver. The amount of tech jobs here/coming is ridiculous...so if you have any expertise/experience...you can get a job without blinking.

If I became unhappy with my remote job (travel, work, boss, whatever), I feel like my mobility to another job would be more limited.

 

[PricklyPete]

if you got comfortable job prospects and don't feel like climbing the corp. ladder anymore, fuck it, go remote and live that life.

This is my thoughts. To be honest, this would likely be a multi year plan in the making. I’m not terribly impulsive, so the idea is just starting to ruminate in my head. We would likely give it a year of trying to kive at a reduced salary asa test (and banking the extra to shore up college accounts and give us a nice buffer).

We would want to do it within the next 3 years (before the oldest hits 2nd grade) to keep the school/friend shock on the kids relatively minimal).

 

[Ns1]

I would sometimes feel siloed if I didn’t have a fruitful conversation with my boss weekly.

Ask your boss about daily 15 minute standups. I'm sure he'll love the idea.



In all seriousness, I'm in a similar position. I got about another 5 years of hitting the corporate ladder, and then I'm willing to take less money to do 90%+ telecommute. Gotta start planting the seeds now....

 

[PricklyPete]

Ask your boss about daily 15 minute standups. I'm sure he'll love the idea.



In all seriousness, I'm in a similar position. I got about another 5 years of hitting the corporate ladder, and then I'm willing to take less money to do 90%+ telecommute. Gotta start planting the seeds now....

I’m the boss that gets my teams to do 15 minute stand ups...I’ve got that covered

I honestly enjoy the corporate ladder...so this isn’t as much about hating my job as much as living my “dream”. I also enjoy plugging away at programming and family/life is a higher priority...so seeing an opportunity to make that happen has gotten me a bit excited.

I will certainly miss my job and we will miss certain aspects of the city (it will only be 2.5hrs away)...but I think we would be happiest raising our kids and enjoying the shit out of life up in the mountains.

 

[repoman0]

I've thought about this too. It wouldn't even be a job change for me because I could fairly easily take my work remote. I know of a small handful of people who have done so at my company successfully. I'm 28 so not married (soonish maybe) and no kids ... main things holding me back:

1. GF would have a much harder time working remotely. She definitely could but she's legitimately good friends with many of her coworkers ... and she's only 25 and already doing extremely well career-wise (promoted twice to lead software eng) and advancements would be slower.

2. I can entertain myself pretty easily without a whole lot of social interaction but still not sure if I'd enjoy living so far away from friends. I make new friends slowly and have cultivated my group for the past 10 years

3. No idea where I want to settle -- Eastern Mass/NH/Maine, coastal NorCal or Colorado mountains. I love different aspects of each. Currently living a few miles north of Boston.

 

[PricklyPete]

I've thought about this too. It wouldn't even be a job change for me because I could fairly easily take my work remote. I know of a small handful of people who have done so at my company successfully. I'm 28 so not married (soonish maybe) and no kids ... main things holding me back:

1. GF would have a much harder time working remotely. She definitely could but she's legitimately good friends with many of her coworkers ... and she's only 25 and already doing extremely well career-wise (promoted twice to lead software eng) and advancements would be slower.

2. I can entertain myself pretty easily without a whole lot of social interaction but still not sure if I'd enjoy living so far away from friends. I make new friends slowly and have cultivated my group for the past 10 years

3. No idea where I want to settle -- Eastern Mass/NH/Maine, coastal NorCal or Colorado mountains. I love different aspects of each. Currently living a few miles north of Boston.

Fortunately the friend thing will not be an issue. Already have a few good friends up there from going there regularly in the last 4+ years. On top of that, three of my close friends in Denver have moved their families up there...so if anything, friends are kind of a motivation. Still, we would be leaving quite a few friends behind.

The bigger issue that I failed to mention is that my sister (who has kids close image to mine) just moved a few blocks from us in the last year. This is honestly our biggest hurdle and potentially might scuttle the whole idea. I feel like our moving away would be a pretty huge dick move. Family is important to me.

 

[ponyo]

I wouldn't. It seems like you have pretty sweet gig and setup right now. I would continue to do the temporary mountain stay but live in the city setup like you're doing now. Liking something part time doesn't mean you'll like it full time. It's not the mountain living I would be concerned with. It would be the drastic cut in the finance and the mental and emotional aspect and consequences resulting from that action. All I know is not having to really worry about money is great freedom in itself.

 

[Mai72]

Do what makes you happy, but of course weigh the pros and cons. How many years do you have left on earth? You might die from a heart attack tomorrow. In fact, at my job a co-worker died from a massive heart attack. Just 2-3 years away from retirement too. Life is extremely short, and this incident was just a reminder of how little time we have on this planet.

My sis works for a small startup out of Boston, and she works remotely in PA. She makes about $120k a year. It can be done.

 

[PricklyPete]

I wouldn't. It seems like you have pretty sweet gig and setup right now. I would continue to do the temporary mountain stay but live in the city setup like you're doing now. Liking something part time doesn't mean you'll like it full time. It's not the mountain living I would be concerned with. It would be the drastic cut in the finance and the mental and emotional aspect and consequences resulting from that action. All I know is not having to really worry about money is great freedom in itself.

I totally get where you are coming from and this has been discussed by my wife and I. We have zero financial arguments. We’re both responsible and I make enough that we have no issues meeting financial obligations/goals. So this is definitely a point to consider...is the financial ease worth giving up.

 

[s0me0nesmind1]

One thing I want to stress - and this is similar to compensation, promotions, etc...

Before you make any quick moves - Your first step should be to just propose or discuss the topic with your current employer. Depending on your boss, department, etc... they might be open to you doing whatever it is you want to do. The point simply being, before you go taking pay cuts - employers these days are often willing to cut some corners to keep talented people around instead of trying to train someone new in hopes that they are just as good as you.

 

[s0me0nesmind1]

I totally get where you are coming from and this has been discussed by my wife and I. We have zero financial arguments. We’re both responsible and I make enough that we have no issues meeting financial obligations/goals. So this is definitely a point to consider...is the financial ease worth giving up.

I think the point he is making is that discovering mountains and shit seems awesome on a part time vacation basis - but consider if you would get bored with it long term or something.

 

[Ns1]

I honestly enjoy the corporate ladder...so this isn’t as much about hating my job as much as living my “dream”. I also enjoy plugging away at programming and family/life is a higher priority...so seeing an opportunity to make that happen has gotten me a bit excited.

I will certainly miss my job and we will miss certain aspects of the city (it will only be 2.5hrs away)...but I think we would be happiest raising our kids and enjoying the shit out of life up in the mountains.

It's like we're dopplegangers. Except I'm already in the mountains and making that 60-90 minute daily commute each way.

 

[PricklyPete]

One thing I want to stress - and this is similar to compensation, promotions, etc...

Before you make any quick moves - Your first step should be to just propose or discuss the topic with your current employer. Depending on your boss, department, etc... they might be open to you doing whatever it is you want to do. The point simply being, before you go taking pay cuts - employers these days are often willing to cut some corners to keep talented people around instead of trying to train someone new in hopes that they are just as good as you.

Good point. I would certainly do that...but I would be the first “remote” VP level person and honestly I don’t know if I could do my job remotely. Who knows. I’m certainly not doing anything rash...this would be a 2-3 year transition and I certainly wouldn’t make any commitment until I got the job I’m happy with.

 

[repoman0]

Fortunately the friend thing will not be an issue. Already have a few good friends up there from going there regularly in the last 4+ years. On top of that, three of my close friends in Denver have moved their families up there...so if anything, friends are kind of a motivation. Still, we would be leaving quite a few friends behind.

The bigger issue that I failed to mention is that my sister (who has kids close image to mine) just moved a few blocks from us in the last year. This is honestly our biggest hurdle and potentially might scuttle the whole idea. I feel like our moving away would be a pretty huge dick move. Family is important to me.

Sounds like you're at least on the hook for talking with your sister about it then if you're going to start seriously thinking about it. Who knows, maybe she wants to move to the mountains too! Especially if you're talking about a 3-5 year plan. (did I make that up)?

I don't particularly care about being near my family so luckily that's one less thing to think about ... my GF on the other hand very much cares. BUT, her parents will be retiring to Florida within the next few years so that will make any potential big move much easier. I think they plan to buy a small condo wherever we end up, or I will build an apartment above a garage or something.

 

[purbeast0]

I have been trying to land a remote position for like over a year now. I'm not looking hardcore or anything and am looking for pretty specific types of jobs with companies that seem good and have a high paying salary like what I make now, but I haven't had any luck yet. I may eventually try to find a slightly lower paying job if that means I can land one, but for now I haven't had any luck. I've worked remotely before on a serious side gig and loved it.

 

[ImpulsE69]

I have been trying to land a remote position for like over a year now. I'm not looking hardcore or anything and am looking for pretty specific types of jobs with companies that seem good and have a high paying salary like what I make now, but I haven't had any luck yet. I may eventually try to find a slightly lower paying job if that means I can land one, but for now I haven't had any luck. I've worked remotely before on a serious side gig and loved it.

I know I love it, but are there really that many remote jobs in Cali (you're from Cali right?). Most of the remote jobs are only remote jobs because someone lives in some no name city away from Cali and talent isn't as focused outside of major cities. One thing I love about mine is that I live in a dirt cheap area so while I may not make as much as I'd make somewhere else, I don't need to, granted I like low key and not living the city life which isn't for everyone.

 

[PricklyPete]

I think the point he is making is that discovering mountains and shit seems awesome on a part time vacation basis - but consider if you would get bored with it long term or something.

This is valid and my wife and I have specifically called out that being at our condo is relaxing because it is vacation and we leave our daily grind in Denver. It being everyday will definitely cheapen the experience...but I’m fairly sure we’ll still love it. I’m in the mountains all the time anyway in Denver...just a lot more people and traffic.

 

[PricklyPete]

It's like we're dopplegangers. Except I'm already in the mountains and making that 60-90 minute daily commute each way.

Nice...although a 60+ minute commmute sounds rough. Mine is max 15 (kitchen to office) and that seems PLENTY.

 

[sdifox]

No rush hour commute = instant win

 

[purbeast0]

I know I love it, but are there really that many remote jobs in Cali (you're from Cali right?). Most of the remote jobs are only remote jobs because someone lives in some no name city away from Cali and talent isn't as focused outside of major cities. One thing I love about mine is that I live in a dirt cheap area so while I may not make as much as I'd make somewhere else, I don't need to, granted I like low key and not living the city life which isn't for everyone.

I'm in MD near DC.

 

[ImpulsE69]

I'm in MD near DC.

Ah, gotcha. My boss is in MD.