My life just tapped me on the shoulder and told me it's time to grow up. Questions about switching a job after years of doing it and maybe being pigeonholed in it inside!
September 20, 2011 3:42 PM   Subscribe

My life just tapped me on the shoulder and told me it's time to grow up. Questions about switching a job after years of doing it and maybe being pigeonholed in it inside!

TL;DR - I'm looking to dramatically change my life in several regards, but I'm presently lacking the confidence to do so. I'd love to hear other people in similar situations who have done a 180 of sorts and find out how to do it myself.

Where to start… I'm 30, work with my father in Real Estate in NYC and make roughly $100,000 a year. I recently broke up my girlfriend (a positive move on my part, but an emotional one none-the-less) which really made my look at my life in general. My relationship with my parents is less than good, and the fact that I work with my father means that at the end of the day, they still have some control over my life to some extent. At present we are cordial, but I have nothing in common with them. My mother is very controlling and manipulative to my father and she is living a pipe dream that a project of hers will change the world. My father seems to have given up on life and has no desire to change his ways or learn new things which would in turn help his relationship with his family as well as help his business.

Leaving my job would mean that I can break the ties with my parents. I would still see them, but I wouldn't feel that they have something over on me, and the thought that they do have something over me is a constant nightmare. Additionally, my father is getting older. If he wasn't in the business I would not be able to sustain it myself. This is also a fear of mine, and I'd rather preempt it instead of having do deal with it in a 'world crashing around you' scenario. The only problem here is that my job has perks that I probably can't find anywhere else, and that because it is a specialized job (real estate broker) I feel that I've pigeonholed myself in terms of having a resume that pops as well as earning anywhere close to what I'm presently making.

I really do need to make $90,000 to $100,000 a year, minimum. I would like to make more, and hey maybe it's possible but I cannot take a job that makes less than this. The idea of having 14 vacation days is also pretty terrible. Right now I can take off whenever I like, but alas, if you aren't making commissions you aren't making any money. I'm very techie, creative and someone who likes to work problems through. I have friends that work at Google & Facebook and I envy them because they get to work for a company that they love working for. I could see myself at a startup, and I'd work my ass off to make sure it succeeded, but I want to be passionate about the job, not just have another job. My resume hasn't been touched in 6 years, and there isn't too much on there that pops from beforehand (plus I doubt employers would care). In person I have a great vibe, and I learn things very quickly. Resume wise I'm probably not hirable, but as far as getting things done, especially in tech, I pop. (Most of my friends who work at Google ask my why I'm not in tech in the first place).

Please note: I understand that a new job will most likely have more restrictions and I get that. I am more than willing to put in my dues.

So there is my life dilemma. Have you been in this situation? I'd love to hear it. Have you jumped ship and made it work, please tell me your story. Work for a company that you think could use me? (I'm not that hopeful here but hey it can't hurt!)

ANON because I don't need people to find out who I am.
posted by anonymous to Work & Money (30 answers total) 7 users marked this as a favorite
What about doing the same job at a different company? Otherwise, entering a new field while hoping to make $90,000 a year . . . um, yeah.
posted by WorkingMyWayHome at 3:56 PM on September 20, 2011 [7 favorites]

TL;DR - I'm looking to dramatically change my life in several regards, but I'm presently lacking the confidence to do so.

You need to do the things that you're afraid of before you stop being afraid of them.

There are no shortcuts.

I really do need to make $90,000 to $100,000 a year, minimum. I would like to make more, and hey maybe it's possible but I cannot take a job that makes less than this. The idea of having 14 vacation days is also pretty terrible.

Then you don't really want that much change that badly, from what I can tell, and I wouldn't be accusing anyone of having pipe dreams about changing anything if you're going to throw out a line like that.

When you're ready to make real sacrifices for real change and real goals, then you'll know what to do.
posted by mhoye at 4:05 PM on September 20, 2011 [22 favorites]

You don't so much lack the confidence as you lack the will. Your post shows a tremendous amount of confidence, so much confidence that you'd have to be a truly exceptional person for it to be warranted.

Unless your own or familial connections can get you a lateral move to a related industry, any situation you find for yourself is going to be less privileged than the one you were born into.
posted by pseudonick at 4:24 PM on September 20, 2011 [9 favorites]

Think about the path that will carry you from where you are now to where you want to be. The "from where you are now" part is important, and I think there are plenty of people who make a jump based on where they want to be, without really considering the path, which necessarily starts from where you are now. So, to address the "where you are now" part, maybe you should take stock of your credentials, your skills, skills you could acquire over a reasonable frame of time, and your professional connections. Then figure out where you want to be, specifically. You want to be "in tech." Can you be more specific? For example, do you want to write code? Do you want to identify markets or emerging market trends? Do you want to help secure financing? Do you want to be the financing?

If you want to write code, but you have no programming experience, then your path is long and arduous. If you want to help secure financing, and you have a record of finding buyers for properties, and you have some financing credential (MBA? I have no idea), and you know some rich folks that you could get to angel invest, and you know some projects worth the risk, then maybe your path may be more reasonable.

Based on what you've written, it seems that you are in a pretty sweet spot, and day-dreamy about something different. And where you are now is a great move to be somewhere, but maybe think evolution, not revolution.
posted by everythings_interrelated at 4:26 PM on September 20, 2011 [2 favorites]

Where to start… I'm 30, work with my father in Real Estate in NYC and make roughly $100,000 a year.


The idea of having 14 vacation days is also pretty terrible.


I really do need to make $90,000 to $100,000 a year, minimum.


You have it really easy. Put some serious savings away before you decide to switch jobs on the erroneous premise that you'll have it this easy again. You may hate the job and want to switch immediately, and there are things more important than money. But in terms of opportunity, you may have a good opportunity now to put away enough money that you have the enviable position of working in a role that you love even if it pays peanuts.
posted by Inspector.Gadget at 4:41 PM on September 20, 2011 [24 favorites]

From the OP:
@ WorkingMyWayHome: Simply changing companies is not an option for me. I need to be out of this business.

@ mhoye: You are right, there are no shortcuts. A major change like this for me will require changes all around. I get that. I think I'll need to take a finer brushstroke to my finances to see where I could really make due though. I have a mortgage, selling my home is not an option, and renting it while trying to find a cheaper place would be a step in the wrong direction with more headaches (and zero advantage).

@ pseudonick: Damn, you are good. Confidence is something I do certainly have, and it is indeed the will to move things forward. My parents can't help me (nor do I want them to) but my friends probably can, or will at least give me a helpful boost.

@ everythings_interrealated: Ideally, I want to be an idea man. What does that mean exactly? Well, I like problems and I'm good at coming up with solutions. For example, no matter the product, I feel like I could come up with an ad or gimmick that achieved a goal for said product. So on that hand, advertising comes to mind (what I went to college for - Bachelor of Science in Marketing). On the other hand, I like tech in the sense of usability (user interfaces and in general just making things better through simplifying them). I can't code, and realize that that ship has sailed. Besides I'm not a 'behind the scenes guy' in that regard. I like to meet with people, and that is the one thing I can honestly say I like about my current job, meeting people.

All these questions about my life have come up in the last few days, but they are some of the strongest feelings about anything I've had in a while. Just rereading what I wrote above is empowering. I put it out there and I can see that this is the seedling I need to really go forward and make this change. Thank you guys so far, and I hope to hear some more people chime in. I've already called some friends to have a sitdown and see how I can even start this job hunt.
posted by jessamyn (staff) at 4:56 PM on September 20, 2011

I'll bite: "Idea people" are a dime a dozen. Everyone has ideas. Everyone thinks their ideas are great.

What's valuable is the person who can take the idea, see who the potential customers are, hook those customers up in a business structure that enables people like me (software developer, general implementer of cool stuff) to build solutions for those customers. Often times that involves coordinating multiple developers, providers of temporary capital, things like that.

So, if you're really an "idea man", take one of those ideas and make it reality. Find your customers, make a case to capital providers, and find the people who can put together a team to develop your idea and ship it (we're out there). There are a ton of us out here who love build stuff, who need guidance in matching what we love to build to the needs of customers ('cause we don't make those connections automatically), and both we and the customers want to find those people. We're actively seeking those people.

What we too often find are people who say "yeah, I'm more of an ideas person", which usually means "I write bad sci fi in my head". Don't be that guy. Be the other guy.

That's the way you're going to stumble into the sorts of money you're looking to make with the skill set you have.
posted by straw at 5:05 PM on September 20, 2011 [15 favorites]

I think Inspector.Gadget is right on the money, and while you're saving up your nest egg, figure out what you want to do. The idea that you'll walk into a well paying and fulfilling job at $100K is pretty silly. You need to figure out who you are and who you want to be, and that takes time. Most of your friends at Google and Facebook did some time somewhere before they got those jobs, even if they just got hired out of college. You may be a highly intelligent and adaptable person but going into another industry cold means you have no knowledge of their business and no identifiable skills. I have the kind of job you want, everyone I work with is intelligent and adaptable and they know more about the stuff we work on then any amount of casual interest would allow for, not just motivated but genuinely interested (and highly motivated). Most of the people who are on the team got there by being an expert in some aspect of our process. So spend some time and pick up a skill.
posted by doctor_negative at 5:12 PM on September 20, 2011

I am going to be super charitable about the privilege aspect of your post, because other people are addressing. And I don't mean that to be a jerk--I really do think the process of moving on in your career is going to come into better focus once you understand your position compared to most others in "the job market."

In any case, about being an idea man: I can relate to this. In a big way. I always saw myself as being better with the big picture, not super-organized and tactical, but more strategic and creative. I think I have reached the point in my career (and my general inner life) where I can say I was correct. It felt like a gamble when I was 25 or so, but at 32 I am comfortable with the fact that that's just who I am. Now, I get paid to come up with big, awesome, creative strategic ideas that other people who actually have their shit together then execute (and then we win and drink beer); 2 of my last 3 jobs have had the term "senior strategist" in the title.

The thing is this: there's no entry level idea man/strategist/creative lead/thinker. The only way that I got to a point of being able to even apply for jobs that matched what I knew my real skillset to be was by busting ass and trying harder than everyone else at other positions that were really better suited to more organized, tactical, together people. It really sucked. In my field (politics/advocacy/nonprofit consulting) that meant several years working as a field organizer, managing campaigns, doing account executive work, etc. Then I got my shot.

In something more corporate, you'd make more money while busting your ass doing the detail work that you're not cut out for, but you still have to do it for a while and it still sucks.
posted by Ignatius J. Reilly at 5:18 PM on September 20, 2011 [6 favorites]

@ everythings_interrealated: Ideally, I want to be an idea man. What does that mean exactly? Well, I like problems and I'm good at coming up with solutions. For example, no matter the product, I feel like I could come up with an ad or gimmick that achieved a goal for said product. So on that hand, advertising comes to mind (what I went to college for - Bachelor of Science in Marketing). On the other hand, I like tech in the sense of usability (user interfaces and in general just making things better through simplifying them). I can't code, and realize that that ship has sailed. Besides I'm not a 'behind the scenes guy' in that regard. I like to meet with people, and that is the one thing I can honestly say I like about my current job, meeting people.

Yet you don't have any experience or credentials to back up what you are trying to sell. Also, you do realize that if you want to get into a startup, you will be putting in 60-80 hours a week for little to no pay for at least the first year, and then very low pay pretty much the rest of the time. Investors say 7 out of 10 startups don't make their money back. 1 out of 10 will get you your money back. 1 out of 10 will double it and the last one will make you some good money. I think that's pretty overblown though.
posted by TheBones at 5:21 PM on September 20, 2011

Also, to be an "idea man," you have to have a fundamental knowledge of the things you are coming up with ideas for. As Ignatius J. Reilly said, there are no entry level idea men. If you want to get into a startup, you have to understand how to code, and I don't mean that you have to have a passing knowledge of how PHP works or what a SQL database is, but you have to understand the functionality and limitations of the code because while you are coming up with your idea, you will also have to come up with the platform and the implementation (something that idea men do) so that you can hire the right technical people to implement your ideas.
posted by TheBones at 5:34 PM on September 20, 2011

there's more to changing your life than just changing jobs. Best of luck finding a job that fits all of your requirements. But regardless, start making all the other non-work changes that you envision.
posted by Neekee at 5:42 PM on September 20, 2011

I'm all over the place in this answer. Sorry for that, but my time is limited this evening. I can't believe nobody has suggested therapy or life coach for you. I'm saying it, because you don't seem to have a solid idea what you want to do, outside of "make lots of money." Narrowing it down will help you get better advice. Also, therapy will help you address how, or even if, a job/career change will impact the parts of your life that you are really dissatisfied with. There might be ways to mitigate or remove those concerns without changing careers.

If you want to drastically change your life, use some of your savings to move to a different place, or take some college courses in a field outside of marketing or business, and travel. What? You don't have any savings?

The more you want the big change, then, the faster you will find ways to cut the bloat out of your budget and find some savings.

whining about my own current situation I'm going to ask you to reassess why you need to make 90-100k. Is it because you are saving like a maniac, or because you are endowing a charitable organization, or because you have 6 kids and hefty child support payments? Or is it because you have grown accustomed to a lifestyle that requires 100k/year to maintain. If it's the latter, may I suggest you have another look at the current economy? If, for some reason, the real estate business you are in tanks (and lo, there are many paths to that type of failure) you may be forced to grow up and find a new career in a hurry. And by "in a hurry" I mean, join folks like me who have been looking for full time work for, ahem, years now.

If you want to increase your odds in the medium to long term, volunteer in a techy way for a cause you're passionate about. Get some numbers. Be able to say, 'donor retention increased by x% as a result of change b on website wwww.exampleforyoublahblahblah' or increased traffic to y page. Or some other quantifiable good thing.

Finally, I don't know what you do in real estate, but if you're selling properties, are you perhaps meeting people in all sorts of professions? If you are, some of them might be willing to have an 'informational interview' wherein you ask them questions about their field.

For real finally, how "well rounded" are you? Do you play a sport? Do you speak another language? Have you traveled? Do you meet with a group of people regularly for any activity? Start doing one or more of those things. Volunteering, in my mind, is not optional. With 100k a year, you can buy your way into a seat some important galas in your town. Hospital wings, that type of stuff.
posted by bilabial at 5:47 PM on September 20, 2011

To echo Inspector.Gadget:

Seriously. Dude.

You have a cherry job. One that many people would literally cut off their right arm for. Appreciate that. Also, there is little to no chance that you will ever again find a job that is both as lucrative and flexible as this job. That is just reality.

My suggestion is that you suck it up and become the best you can possibly be at this job. Learn as much as you can so you can take over business from your dad when he retires.

Appreciate the good fortune that you have. Find happiness in other areas of your life.
posted by gnutron at 6:07 PM on September 20, 2011 [4 favorites]

You're going to have a really hard time getting a lateral salary move without doing pretty much the same job, especially when you're looking at 6 figures.

Do you need 6 figures? No. Millions of people in the US demonstrate that. Are you willing to give up what your 6 figures is buying you? That's the real question.

At one point, I made a move that was in theory lateral from an experienced, well-paid position to another in a different career that shared a skill set and for which many aspects of the job I was vastly overqualified. The result? A 50% cut in salary and it would have been more if I hadn't caught them in a typo in their job ad (it should've said "pays up to $x" but said "pays $x").

I eventually returned back to my original field because in the time away, I discovered that I was happier/iest doing this job. I say go ahead and explore some, but be realistic and pragmatic about the choices. And make sure that there is ample joy in your life. I have a hard time detaching from work challenges and I'd rather that the work challenges be a source of joy than a source of frustration. If you detach easily from your work and really don't care what happens in that twenty some odd percent of your life, then your actual job doesn't have to matter.
posted by plinth at 6:12 PM on September 20, 2011

Anon, it's a big deal when you get hit with that realization that you need to move on, but you don't have to do hastily. Take your time, give yourself some room and ask yourself some questions. What do you enjoy? Do you have any hobbies or interests that could be turned into businesses? Should you just save up for a year or two and start your own business?

I use those questions specifically because you are already a few rungs up the ladder of success and I don't see any reason to take any steps down. (Start your own biz on the side.) Give yourself time and do tons of research and be successful at whatever you decide on. You don't sound like a "job" guy though.

FWIW, I physically moved away from my parents when I was 17. At 43 I'm still dealing with the results of their controlling ways. So I guess what I'm saying is use your resources to your best advantage and don't be too hasty. Move on but do it with some planning and consideration because simply skipping away and changing your life won't completely remove those familial burdens anyway.
posted by snsranch at 6:36 PM on September 20, 2011

What do you think you mean by saying you need to grow up?
posted by J. Wilson at 6:36 PM on September 20, 2011 [2 favorites]

I recommend you make a number of basic, grownup-stuff changes. Pay down your bills, establish some savings, update your resume. Why do you need 100K/year? Debt? Coke habit? Lots of dinners out/drinking/living well? Think about what you really want to do, and if you're willing to take some risks and make some lifestyle changes to do it.

Startups need people who can (usually) code well, and/or do the finance, and/or be the lawyer. You are unlikely to make 100K at a startup. You might cash in big, with the right skills, at the right startup. But there are no guarantees. Successful idea people work a lot of hours, in startups and elsewhere. It's quite possible that you could be way better at your job, make a lot more money, and take over the firm. If Dad knew that you were bringing in huge business, you wouldn't feel (or be) dependent. How to do this? Start going to seminars, and trade association meetings, and whatever else people do in your field to get better at it.

Being tech-ish is useful, but you have to have the hard skills, not just the ability to learn. It helps to have a goal that's more focused. Do some research at the library on career-changing. Learn about using networking, and tap into your network to talk to people about what they do, how they got started, what skills and education they had when they started, what they like/don't like about what they do, etc. If you really want to change careers, you may want to take classes or start studying on your own.

It's more common for people to move to affiliated fields. To go from real estate sales to development, or managing property. Look more closely at the field you're in to see if there's a better place for you.
posted by theora55 at 6:47 PM on September 20, 2011

If you can't get the same job you're doing now at a different company (which is really the best option), you should learn to program. It will take you a while, but it sounds like you can keep doing what you're doing for a while. I guess what you'd want to do is teach yourself the basics by learning Ruby on Rails or PHP and building something. Also, spend a lot of time reading code, and reading high-rated answers to high-rated question on StackOverflow and understanding them. Get yourself a good algorithms book, and work through at least the chapters on sorting and a bit of graph theory. Also, buy the Gang of Four book, and maybe Patterns of Enterprise Application Architecture and read them, then go and rewrite the piece of crap site you wrote as the first thing I told you to do (unless it's making you money, then leave it the hell alone for god's sake.) Read a lot of code. Every time you find something cool that you like to use, find something similar that's open source, and read the code for it. Develop a sense of what's garbage code that some asshole threw together, and what's not.

Somewhere in the middle of doing that, get an entry-level-ish job. In NYC, you can probably earn at least $75,000 if you're a competent entry-level programmer. Do that job for about a year and learn every god damn thing you can, and then switch jobs. This should get you to at least $85,00 or so.

I'd say all-told, you could do this in 3-6 years.

. You are unlikely to make 100K at a startup.

Emphatically not true, at least in SF and NYC! Hacker News did a survey a few months ago of programmer salaries, and salaries in the 85-120 range were very common!
posted by !Jim at 7:24 PM on September 20, 2011 [1 favorite]

Emphatically not true, at least in SF and NYC! Hacker News did a survey a few months ago of programmer salaries, and salaries in the 85-120 range were very common!

Yeah, but those guys are rock star programmers with provable skillsets, degrees, hobby open source projects, and have been coding since middle school. Its foolish to think you can go from never have written a line of code to demanding even 40k. Even with a lot of experience and proven skills, unless he's a rock star coder, he's going to take the path eveyrone else takes - college/training, internship, low-level job, etc. You're looking at a lot more time than a year and a lot less money than 85k. Paul Graham wrote that you can learn programming in 12 months. That's just to get to level 1. The guys casually pulling 100k were level 1 when they were 12 or 13.

I'd agree with you if he was some kind of hotshot, but he's been doing real estate not hacking for the past 10 years. I'd also be afraid he'd be a toxic assett if he's been pampered by the family business and might not be able to easily move into corporate culture. He's going to have a very hard sell unless he's especially good. Not everyone is cut out to be a programmer, btw. About 25% of my job is coding and mostly easy shit like php. Its not something I'd want to do 100% of the time. Good coders really are born.

Btw, anon, 2 weeks vacation isn't 14 days. Its 10.
posted by damn dirty ape at 7:50 PM on September 20, 2011 [4 favorites]

I am 30 years old. I am a programmer in the San Francisco Bay area for a large-ish tech company. I make a base salary of approximately $125k/year, and I get 30 paid vacation days every year (more or less, technically there is no set limit).

I have being writing code since I was 15 and professionally since I was 18. I went to college and majored in computer science and worked for the US government while I was there. I took a job at a startup after college and we were lucky enough to be acquired by someone larger.

From my first job where I did programming until my salary crossed that $100,000 threshold took me about 8 years. I have been in this industry now for over a decade and I know lots of people at my current company, or who used to be here and now work at places like Google and Apple, and startup founders I used to work with and a variety of people who feel I have a good reputation that I could talk to if I were interested in switching jobs. These people would probably hire me at $100k+ to start, because they already know I have experience and they've been happy working with me in the past.

Also, I am not just generically "techie". I am a professional C++ programmer with specific knowledge of HTTP servers and clients and peer-to-peer delivery. I have been doing this for years and I have a knowledge of our specific codebase that is shared by only about half a dozen people.

So, can you make $100k+/year in tech. Sure I know how to do it. You need to put in 10 years of practice and hard work. You need to be good at what you do and willing to go the extra mile. You need to establish a circle of colleagues and friends who respect you. You can't just say "Working for my dad sucks, can I have one of those engineering positions you guys have open?"
posted by tylerkaraszewski at 8:23 PM on September 20, 2011 [8 favorites]

I have a similar background to the two people who just responded to my comment, and I stand by my comment.
You can't just say "Working for my dad sucks, can I have one of those engineering positions you guys have open?"
I agree, which is why I didn't say he could do that! I said after 2-6 years of hard work, he could get a junior level position, where he could make $75,000, which is a lot less than you make after 10 years. And the guys making $85-100k are not rockstars, they're competent solid coders. I know this because I am one, and those guys are my peers. I think the guys earning more than about $100k probably do have specialized, highly in-demand skillsets (are rockstars, to use the obnoxious parlance of the tech community.)
Its foolish to think you can go from never have written a line of code to demanding even 40k.
Sure you can, after 2-6 years of hard work.

I'm sorry, but I just don't buy into the mythology of programming that you have to be some kind of god of programming who started when s/he was 12 in order to be a competent programmer. I think it's perfectly possible to start doing it later in life and have a very successful career if you're willing to put in the effort.
posted by !Jim at 8:49 PM on September 20, 2011

The issue is not that you need to be a programming genius to be making solid money. But those making impressive money now were thinking about programming before the web was monetized. They were ahead of a curve.

Those people starting now? They're suffering from the realities of capitalism. High wages lead to a saturated market. The need to learn quickly necessitates a degree, and the desire to stand out among new graduates leads to expensive prestigious education. So while they might still get the salary, they will also lose years of income production along with the cost of education. And while Google will continue to pay well, there won't be the huge payoff. That is for the next new thing that catches us by surprise.

Look at the demographics. You are in the top 7% of your demographic. Without any fancy tech knowledge that is so predominant among the top earners of that demographic.

Right now you have been able to build on your father's experience, which is a rare opportunity that is contributing to your high salary. You have the vision to see that the company could expand. So do that. That is something available uniquely to you, and geared towards your skill set.

But following a path built by others guarantees you won't have a salary that is set aside for those lucky enough to learn a skill set at the beginning of its success.

And take a moment to realize that your salary is absurd. Not that you don't work hard or deserve it. But most people work hard. And many are bright. But markets ebb and flow, and even specialization doesn't guarantee a lifetime of progressive steady income growth. Which is why only a small percentage of people make six figures. So get to digging and make a budget that frees you from your golden cufflinks. It's one thing to enjoy a high salary, and another to be beholden to it.
posted by politikitty at 12:20 AM on September 21, 2011

One possible way for you to transition would be to get an (elite) MBA and then try to get into product marketing for technology companies, particularly those in the real estate space (Zillow, etc.) From there you could transition to the broader technology market.

After the MBA, in a company relating to real estate, you could be making $100k/year by about year 3. Not a bad transition.
posted by 3491again at 1:14 AM on September 21, 2011

Law School?
posted by zaelic at 2:54 AM on September 21, 2011

I am a programmer by qualification. When I started doing real programming (i.e. not as a hobby) I knew I could not take it for long. In fact every morning what I looked forward to was the McDonald's big breakfast before work. That kept me going. Sad huh? Just FYI, it is not the programming, but rather, the attitude of the company I worked at.

One day, I decided that you know what. I could not do this. Very, very, very depressed. I then made a radical decision to quit, and join up full time with a company I used to work part-time for (cg visualizations, web design etc.). My pay was basically cut in half, and time off dropped to 7 days.

Did I enjoy this new job? Parts of it yes, parts of it no. But it was much more fulfilling. I worked on working towards a future goal of getting to where I wanted to be. Working day to day, evenings I'd be working on personal projects - after all, luck = opportunity + preparation. And one day, a chance encounter came, and it was a very difficult choice, do I give up my life, friends and work (I'd a new job that was not bad) and take a chance on going abroad for an internship that may not give me a job, but had a slight glimmer of hope?

I hate regrets. I'd much prefer to try and fail, rather then not tried at all. I took off for the usa. It was tough, back home I was doing not to bad, in the us, I was basically at the bottom rung.

~7,8 years on, following this new path, I have worked in many countries, and am very content with life in general. I enjoy my work, so much that I still do go home and do more of my own for-fun stuff.

Bottom line is, in my experience to get something, I often-times need to give up something. Question is, what are you willing to sacrifice to achieve your future goals?

Side, side fact: This change in my life was inspired by a Dragonlance novel, Dragons of Summer Flame. Palin, a young mage had to sacrifice everything, in order to save the world. What can I say, I'm a dreamer.
posted by TrinsicWS at 4:17 AM on September 21, 2011

From the OP:
Thank you all for the insight. A lot of it has been really interesting, like how I could be considered a toxic asset... never thought about that. It's also a wake up call which sucks to hear, but is helpful regardless.

A few quick things:

- I'm trying to get out of real estate completely. That means getting a job that has to do with real estate is not in the cards.

- I'm NOT trying to become a programer. I don't know how things got so off topic so quickly, but everyone is giving me programming advice. While I'd love to learn, it would be as a hobby not a job. I realize that I'm too far behind to make it work and as I've said, I'm not a behind the scenes guy. I'm the guy that the programer would explain their code to so I could then explain it to investors, etc. Not that I want you to stop commenting, but honestly, I don't need any advice on programing.

- Saving up some money and then making the switch is a good idea. I'm trying to move things along quickly, but doing that can certainly help the transition.

- A lot of you think I've been pampered, which I understand and has some validity, but I am a hard worker. That is one of the reasons why I'm trying to leave, I'm working my ass off and the big guy isn't. Unfortunately this is a business where you can work until you are blue in the face and more often than not see all your work get you nothing. Over the last few years I've lost hundreds of thousands of dollars, sometimes because of a random reason and sometimes because people decided to screw you, close friends included. It's the nature of the business that is getting to me (among other things) which is why I'm trying to remove myself from it completely.

Thank you all again for the insight. It's been good to hear it echoed from several people as well. It's clearly going to be a challenge, but I'm up for it.
posted by jessamyn (staff) at 8:52 AM on September 21, 2011

Over the last few years I've lost hundreds of thousands of dollars,

This is exactly the kind of statement that I think therapy might help you out with. The rest of this paragraph makes it look like these were real estate deals that fell through.

If that's the case....remember that adage about counting your chickens before they're hatched? That's because they're not chickens if they're still in the eggs. Same with money and real estate. It's not yours until it's in your hand.

My previous advice to think more deeply about what you want to be doing still stands. What kinds of things do you find yourself day dreaming about? What hobbies would you take up if you had all the time in the world? What areas of your spending would cause you the most pain to cut?

These questions all could lead to your new career. Or maybe not. But they'll definitely lead you to re-evaluate the nuts and bolts of your life, rather than just the surface.
posted by bilabial at 10:15 AM on September 21, 2011

Also, there is little to no chance that you will ever again find a job that is both as lucrative and flexible as this job. That is just reality.

Not true.

BUT you need to work hard for 5-10 years to get there no matter what career you decide to pursue. Companies don't invest in potential at that salary level - they invest in a proven asset. If programming is your path you have some great suggestions.

I don't know if I would throw away the real estate industry so lightly. There must be other areas that you would enjoy. If you have sales skills you can probably transfer to many different lucrative paths out there.

Right now you need to research and figure out specifically what you want.

I suggest "what color is your parachute" to explore all possible career paths - and a career coach if you need more assistance. Therapy probably couldn't hurt either. You feel stuck in this career because of your parental dynamic, and working on that might help with your career crisis. You may find that you are projecting your need to be independent onto your career, when really it can be managed in another way that will keep your cushy and flexible job for you.
posted by rainydayfilms at 10:57 AM on September 21, 2011

Technology doesn't just mean programming. There's a lot of sales, marketing, business development roles in technology that pay well, but are, as you can imagine, really competitive to get in. Note that technology is one of the few growing sectors in the US. Combine that with the proliferation of industry press (TechCrunch, VentureBeat, NYTimes tech) and social media outlets means that everyone is looking at switching into a startup or larger tech company now.

Having said that, it's really not impossible...just takes a lot of hustle. I would suggest combing through jobs on to see what are the skillsets required. Agree with 3491again that you may be most attractive to companies like Zillow or Trulia, who many need someone with an inside view on the industry. Try to find folks at those companies on LinkedIn and do some informational interviews to learn about what their career paths, how they got there, and their daily highs and lows. Consider taking on an internship or part-time role first. From there, you can potentially jump to other vertical markets once you build up your skills and your network.

You could take another approach and find a sales job in an unrelated startup vertical, but honestly, I would think twice about a company that would hire someone without related domain experience. If you seriously want to jump into tech, I'd think your biggest near term consideration is the learning experience and the credibility of the company that you join.
posted by hampanda at 12:10 PM on September 21, 2011 [1 favorite]

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