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

Let me start by giving you a brief history.

I’m a 34 year old female living in the US. I am an employee of a small finance company. I don’t hate my job. Just dreaming of more. I have spent many years going above and beyond in my office. I find my job a challenge and have the opportunity to learn new skills.

I would be happy growing the business, expanding, restructuring. Making more money. Period. If the company grows, we all make more money, and help more clients.

My boss only recently became a partner in the business. Maybe within the last 4 years. She hired me in 1999. I have worked with the company for a total of 12 years. I left for a bit in between. She comes to me as a sounding board for ideas about the business, suggestions, advice, and collaboration. The company has paid for me to take extra training outside of my normal duties to become more knowledgeable about marketing, business writing, and microsoft programs.

The problem. She’s a terrible manager. Her employees don’t respect her, roll their eyes when her back is turned, talk sh!t about her when she’s gone. She is passive aggressive, micromanages, doesn’t trust her employees to do their job, doesn’t address poor behavior, permits employees to slack off constantly, and above all seems to have no idea how address these issues.

“Not everyone is like you and me.” She’ll say. “What can I do?” Of course this is to me in private.

I know that I’m the #3 of the business. President (Retired about 2 years ago), Vice President (My “manager’), me, and 5 more employees.

The company was founded in 1934. It’s not going anywhere. But that’s it’s downfall as well. It’s not going anywhere. There’s no future for me. I talked with her about growing the business. Adding an employee or two (in the future). Utilizing new strategies and programs to increase revenue. She has no drive to grow the company.

So I thought, okay, I need to step back. I’m just an employee. I’m not a partner. Heck, I’m not even a ‘manager’. I’m an employee. Period. Thinking there must be more to it. She has a lot on her plate, running a company, “managing” employees, micromanaging everyone, triple checking everything. It’s a lot of work. Now is not the time.

So here’s the kicker. Nine months ago she started an LLC on the side. The only reason I know this is because there was a note on her desk (like two weeks ago) reminding her to order checks for XYZ, LLC. Since it’s literally none of my business(es) I didn’t ask about it. But I did research with the state about XYZ, LLC.  Found out it’s been open for 9 months and run out of her home. Since she’s formed an LLC and is ordering checks, there’s business transactions happening. She’s not the type to spend money on something frivolously.

It’s just made me lose hope that her energy will be spent growing the current profitable business (thus creating a future for me).

So now.. what should I do?

A) Stay with a secure job making roughly $21 hr (with bonuses) and no future?

B) Get a new job? <– scary.

C) Start a business? <— Can’t decide what I want to do. (But this is what I WANT to do.)

D) Go to school PT to get a “formal education”?

Thanks everyone for reading. I look forward to your comments.


  • 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.

    • Thank you for the comment! I agree… no exact vision yet… more like too many visions. I am very ambitious. What is a startup weekend?

      I think you’re right about the “lifestyle business” comment. Pres. and VP are content and happy. Making $ and not too worried about anyone else.

      I’d rather see the entire company grow and succeed.

  • 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!

    • I know there is no way I can sit around and wait for a promotion. There’s not even a position in the company to strive toward.

      Find another job. – Most probably option. The most safe option.

      You’re comment, “You will fail.”

      Where does that come from? What experience have you had to be convinced that’s the outcome? Because I’m “obsessing” about what a “leader” is doing?

      Just wondering.

      Congratulations on finding your passion!!

      Thank you!

      • That not only comes from experience, but knowing that people who work jobs and have a steady income will panic when income fails to come in and they are operating for 3 months in the red. it’s a big risk and it’s something you not only have to prepare for and have new customer checks lined up (not prospects), but actual checks before you really have your business operating to a level you won’t fail. The first 1-2 years is often failing and when you don’t know what it is that you want to do, you already fail because you don’t have passion guiding you through. you will know when you are ready when you picture yourself living on $500 a month for about a year or two and are ok with that. Whose couch are you sleeping on? Where and what are you eating? Do you still have a car? Etc, etc.

  • 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…

    • Politics. Corporate career. – Thank you.

      I agree in her having no guilt in leaving everything everyone in a mess. She’s very selfish. Does she really have any obligation to talk about her LLC? I do fear she would try to “keep me in” when I tell her I’m jumping ship. I appreciate your words about her not believing.

      I need out.

      • A job is not a marriage. Unless her LLC competes with the current company or affects her day to day work, she has no obligations to report anything.

        Some people prefer to pursue hobbies in their free time, some prefer to have a family, some prefer to sleep. Some prefer to go to night school and learn something. Some prefer to start a side business. What she does in her time outside work is her own business.

  • 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.

    • I think I need to get the heck out.

      I don’t want her job. I don’t LOVE the business. It’s super negative. The money is good. But, taking money from people is the primary goal in the entire company. I don’t want to be there anymore.

  • 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.

      • Don’t be fooled by what you want to hear. My advice – have 3 years living without tapping into your 401k to find what you want to do. You can be stepping out to do something good and great, but you lack hustle and it will be hard developing those skills in less than a year. You’re smart, so you will get there. But learn from your boss now as she has a lot more to teach you than you think.

  • 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!

    • Actually, that’s what she should do!!! Work for a startup for 2 years.

      Or, live without her next 6 checks to see how that goes. Pick 6 people in her family and donate her next 6 checks to see if she’s able to live without a check. If she can make it 6 weeks without a paycheck, she can probably make it. But, the key is for her to actually not have the pay checks at all. She’ll have to be willing to part with that money.

    • +1

      Yes – this is exactly my thought – Why not try interviewing for a new job at a financial services startup?

      If you land a startup gig, you’ll get to experience life at an ambitious company with great career advancement potential, and you won’t have to take much risk.

  • 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.

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