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. 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.

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.

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.

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.

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?"

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.

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.

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.

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.