Vice President, Boss, Manager. Start-up founder?

The business you currenntly work in sounds like a lifestyle business- the owners are content as long as they enjoy a nice lifestyle from it. You sound too ambitious to stay with this but starting your own business is VERY different from working for someone. Honestly, you sound more frustrated with where you are than inspired about where you could go with your own idea. You don't have a vision yet so you can't start a business. If you had a serious idea for a business you could work on a side project while enjoying the security of a salary. Doesn't sound like anyone in your business will notice and you can plan your exit thoughtfully if you hit on a viable idea. If you want to explore this more go to a startup weekend, work on someone else's team and learn what it takes to startup a new venture.

If she has started her own business, she's most likely planning to jump ship soon. You can wait it out and hope for the promotion.

Or you can find another job. But for the love of God, do not start your own business! You will fail. No vision, no passion, only frustration, and you're more focused on what your boss does rather than what you obsess over when in your own thoughts.

I've been there... 4 years later, I found my vision by following my passion.

Find yours. Good luck!

As the above commenters, I think you should find another job, and not create a startup. Your post shows you have some skills in politics, which is precious in a corporate career. Nothing shows me you have what it takes to create a startup.

Your boss is not trustable. She knows there is no future in this company, that's why she has a side project. As soon as she has traction, she will leave. She won't have any compunction leaving you in a mess. So you should find another job before she leaves. No need to talk to her about your intentions, she didn't talk to her about her LLC... After all, if she tries to keep you in, you could tell her you felt she was not engaged like before and she didn't act like if she believes in the future...

An alternative: you can keep your job and prepare to become VP when your boss leaves. It is a low probability event, the most insecure. But if you are quite sure she will leave, and if you can build a plan for the company, it's doable. But most probably her LLC will be a failure, she will stay, and the old company which employs you will go bankrupt. Not so good on your resume...

I agree that starting a business with your current doubts isn't the way to go. If finding a new job is scary, starting your own business should be 10x scary. A running business is a machine that already has suppliers, customers, roles and people to fulfill that roles. Then you take a job at it, fulfill one of it's roles and get paid. Opening your own business demands you to build the machine... even if you know a problem that you want to solve, you must find suppliers willing to sell to you, buyers willing to buy from you, fulfill a lot of roles yourself and eventually create the roles and find people to fulfill them. It's really hard, so I recommend you to do it only if you know that's what you want to have as a career (and even then it will be really hard).

I also agree that if your boss' company works out she'll jump the ship. Maybe the question you should ask yourself is: do I want to be promoted and do her job? If the answer is yes, I think you may benefit from waiting for a few months to a year and see what happens (if she quits and if you get promoted).

The job option looks good. Does it do you any harm to look around and see how much you're worth to other firms?

IMO, schooling is great if you're really wanna learn more about the subject, the diploma is valued in your specific market and you don't become a slave of debt. If you like it but the formal ed is not valued, you can study by yourself (on books or sites like Coursera, EdX and others). If you'd become a slave to debt I'd say the same. If you really enjoy the subject and the course is affordable enough, you could take it as a hobby, even if the diploma isn't valued.

Startup founder here.

I think I disagree with a lot of the commenters here. Frustration is fine starting point to a career as entrepreneur. Most startup founders or business founders started just witj that.

Becoming entrepreneur starts with wanting to start a business, not with a vision or product idea.

Here is how it usually goes: You decide you want to start a business. You then find a product idea. Usually your first product fails, but you try again because you really want be successful as an entrepreneur. You keep tweaking your product and your go-to-market strategy. One day you start succeeding. Along the way you develop a vision for your market, your product and your company.

You should know that starting a new business from scratch is extremely difficult, and you may have to accept changes to your current lifestyle, or use your lifetime savings in the process.

There is perhaps an easier way to be your own boss: become a franchisee. Much less risky, less exciting too, but a good way if you have truly the desire to be your own boss but not the capacity to invent a new product category.

B and do it quickly because this kind of life will eventually affect your health too.

Startup co-founder here.

Firstly, I want to congratulate you on your ambition, your work ethic, your ability to work successfully for a difficult boss, and your inclination to look ahead and consider next steps for your own career.

Secondly, I would encourage you to start school part-time no matter what you decide as the lack of a degree -- as well as the lack of information that will be valuable to you -- can close doors and hold an ambitious person back. If time and/or geographic location are a barrier, there are a number of accredited and reputable universities today (like the University of Maryland University College and Penn State's World Campus, among a multitude of others) that offer the opportunity to earn a bachelor's degree online.

As has been pointed out, the need "to get the heck out of there" can translate to either alternative employment or entrepreneurship. And as your current boss has demonstrated with her LLC, employment doesn't necessarily foreclose entrepreneurship in a noncompeting field.

With respect to alternative employment, it seems to me that an individual with your background (12 years working in a small finance company) and inclinations (someone who values stability and job security, who is "happy growing the business" in order to "make more money" and "help more clients," but who is somewhat uncomfortable with the idea that "taking money from people is the primary goal in the entire company") may want to consider employment in the credit union industry, where competent and ambitious individuals can advance without equity ownership.

With respect to entrepreneurship, I love it that what you WANT to do is start your own business! I would strongly encourage you to carefully consider exactly what kind of business you want to start, the market opportunity and likelihood for success, what skills and expertise you'd need in order to make it successful, whether you'd need a co-founder to complement your skills and, if so, who that might be before you cash out your 401(k).

Best of luck to you!

Startup founder here, in the online financial services space. This space is white-hot right now, and frankly we need more very bright people with direct industry expertise, not just tech people. Sounds like you know what you bring to the table... so articulate it, market yourself...and bring it on!

Go to your boss and suggest that you take over the operational part, of course as part of a decent salary.

You go above and beyond for a company usually because it offers a secure salary. Going above and beyond for yourself for 3 yrs straight with no income in sight and a drastic lifestyle downgrade is insanely tough. I get you've been with the same company 12 yrs and are afraid of a new job, but the first month will require some adjusting, and then it's smooth sailing. How do you have the courage to start a venture, when you don't have the courage for a new job ? Think about it . Tough questions you gotta ask yourself !

You can do both, be a founder and an employee if you work in tech as long as you can code. Get an idea, and work on your start up after working hours. If you find that it is making money, do it full time.

Update!

Jumped ship, got a new job. New industry. New career. Been with the new company since 8/2016. Still not feeling fulfilled. Still feeling like I'm in the rat race spinning on a wheel.

Think I need out.