I have had lot of conflicts and difficulties with my former bosses in the past 7 years.

I have had lot of conflicts and difficulties with my former bosses in the past 7 years. I am 35 years old and for me it feels like I am never going to be able to work for somebody and be happy again.

That's why I am considering starting a small business myself. I am still employed and I am wondering if I should endure any longer (and have the security) or risk everything for the dream of becoming self-employed.

Why women love us:

  • Daily articles on career topics
  • Jobs at companies dedicated to hiring more women
  • Advice and support from an authentic community
  • Events that help you level up in your career
  • Free membership, always

Share your insight

Join an authentic community that helps women support each other at work. Share your professional experience or ask for advice — you can even post anonymously.

35 Comments

Join the conversation
  1. Anonymous

    I would look at the common denominators in those experiences and reflect on those and see where you see yourself with growth. If you've had a dream of being your own boss the go for it! You won't know unless you put yourself out and commit to it. In saying this, if you hire keep in mind what and how you were made to feel with your employees and strive to pass a long a better experience than you've had. Good luck.

  2. Marissa Coyne

    YES! This! If you are constantly having issues with supervisors, take some time to think about what the common denominators were for these interactions and take steps to make sure this doesn't happen (when you are the supervisor) with people you hire for your new business.

  3. Anonymous

    I am 48 now, and when I was 35 I quit a very successful career to become self-employed. It was the best decision I ever made, but it came with great challenges. It took 5+ years for my business to become profitable enough to provide the financial security I walked away from. What got me through it was that I had a hefty amount of savings to live on in those initial years when my business generated very little profit. My advice is to make sure you have a good amount of money saved before you quit and branch out on your own. Perhaps you can segue into self-employment by starting your small business on the side while you're still working. (Knowing what I know now, that's what I would have done). Keep in mind that self-employment often means you'll work harder and work longer hours than you did working for someone else - so just because you'll be your own boss doesn't mean it will be any easier. And you won't get certain benefits, such as paid health insurance, paid vacation days, etc.

  4. Anonymous

    Thanks for sharing your own experience regarding self-employment. It seems that I am somewhere in between being very optimistic (like if I go all in now everything is fall into place and my business is going to be successful immediately) and completely pessimistic (it's too risky and the procentage of those who succeed is very little). My savings are not so big and I would invest them into my business, so thanks, I am going to plan to start my small business on the side. I am sure that working for yourself is hard as well but I think that the flexibility and the freedom are worth it.

  5. Anonymous

    The flexibility and freedom of doing your own thing ARE worth it, but the risk is real. Instead of feeling pessimistic, try to find the balance between optimistic and realistic. That's the sweet spot. Best of luck to you in whatever you choose to do.

  6. Anonymous

    Some people are meant to start their own business. Such people get fired from their jobs or leave them. Maybe you are in that category.

  7. Anonymous

    It would be best to do both for a while.

    I did this for a little over 2 years before cutting the cord. I was able to set up my business with no debt, without going into my savings and earn extra income to help pay for the accounting and legal setup of my company as I built up clients. I had a nice cushion for the start of my self employment and it also made working as a W2 employee so much easier because I had a plan to leave so I was basically working for my dream.......

    There are a bunch of extras that made this approach work in support of me as well. I wrote off my renovation of my home office, bought a new computer and other office equipment (shredder, printer, cell phone, office supplies etc) and purchased my medical benfits. All of these things set me up to succeed and I've actually been in a situation to turn down work because I now only want to work 25 hours max per week. If you spend the time to set things up correctly, your life if so much easier.

  8. Anonymous

    In my first job, I had a boss (who was also the owner's son) who was verbally abusive. I stayed too long at it still affects me today.

  9. Stephanie Branch Lekowski

    Go for your dream ?!

  10. Anonymous

    If you've saved plenty of money and can afford to get your business off the ground and pay for your life and benefits while it comes together I say yes!!!!!

  11. Terrie McWhorter

    I am going to be completely honest and speak from a position of...yeah I went through this myself... Step back and take a look at YOU. The saying it takes two to tango is true. I asked a staff psychologist who I worked with if she would talk to me like a psychologist and NOT like my friend. It was the best thing I ever did because I was able to learn that I had these certain triggers that made my she bear tiger claws come out. She then taught me how to NOT be triggered. ((or at least keep my triggers hidden by those who like to push buttons) Anyway, very long story short as this was way early in my career...look at yourself and why you are unhappy working with others FIRST. Because of that, I learned that I truly like assisting others with their journey's in life and how to navigate them!! Best of luck

  12. Anonymous

    As someone who’s done this twice in my 20+ year career and am currently running 3 small (digital) businesses, I advise to start your business now, while you are still employed.
    Fail fast. Test your business idea asap don’t spend a ton of time and money getting it all set up and bringing it to market. This is where most 1st time entrepreneurs go wrong- Sinking time, energy and money into something before they know if it’s a viable, sustainable business for them. Ideally you launch a small business whenever you aren’t working your day job. Vet it while you’re employed and save 6 months minimum of living expenses before you take the leap.

    Self employment isn’t the glamorous lifestyle most represent it to be. It takes a lot of self-discipline to create your own schedule and hold yourself to it. Even if you are introverted, it still gets lonely. You need a mentor in your field, this is where I went wrong in my business- I had nobody *with experience* in my field to bounce ideas off or to utilize as an informational resource.

    All of this aside, if you’re having problems for years with multiple bosses, you should write a list of bosses and the problems you’ve had with each one. There’s prob a pattern that circles back to you. Having self awareness is imperative to being a successful business owner unless you’re flush with cash and resources. You need to be aware of your weaknesses so you aren’t trapped by them in some way within your own business. Do the work on this, it’s worth it.

    Best of luck to you and whatever the future may hold.

  13. Anonymous

    This is probably a good time to seek therapy. Remember the truism, "wherever you go, there you are. "

  14. April Line

    All of this is great advice and it is good to hear both sides, "i hate it so hard" vs "best decision i ever made!"

    I am/was in the same boat as you, and in therapy to sort myself out, and while it ABSOLUTELY DOES take two to tango, I learned in therapy how to have the confidence to trust myself enough to put my communication skills to work, and how to respect myself not to sign up for mistreatment just because one of my quirks is that i actually LOVE to work, and i derive a lot of satisfaction and affirmation from doing a *good* job.

    And i learned to understand that i was, because i had a low opinion of myself, trying to do executive/manager work at the wrong level of the corporate structure. So maybe you need to apply for higher positions vs whatever career level you are currently at?

    I finally found a boss whom i thought was my forever boss because we were an excellent team, we made amazing things happen, he took my input about good moves to grow the business and we increased profits *DURING COVID*, partially because he had never done the math about what he needed to charge to be profitable. We started two additional LLCs, we inspired a 180 in the work culture, it was all so neat.

    Then, dude started down the path of an ongoing midlife crisis that really changed things, and before i knew it I was having the same problems with him i'd had with many previous bosses/managers, where they suddenly think I am after their job/stuff.

    This dude had the audacity to go on like 4 vacations in 6 months, during which time he was also out of reach pretty much daily after 12 noon, and just "let" me handle things, and then resurface and tell me it was MY fault the staff trusted me more and it was my fault that he felt "out of control of his own business."

    At which point i was like, "how would you like to fix this? I would be SO SO happy to not be in charge of all this stuff and be able to take some time off." And he said, "i dunno. I can't talk about it right now." That happened 3 more times before he finally took me on a ride on a small farm vehicle and said all kinds of bananas stuff that made me quit suddenly and without notice. Because a) almost all of it was not true and b) it was extremely clear he no longer valued my contributions c) taking me on a vehicle and removing my agency while he intended to say irrational and ridiculous things was an abuse of power and of me. That was the end of July earlier this year.

    Since then i have been freelancing around, making more-or-less the same $ i made working 80 hours a week in 35ish hours a week. I made a lot of good networking connections and a lot of excellent impressions while i was working there, so I've kind of accidentally become a small biz consultant.

    Which brings me to this: really depends what kinda business you wanna start. If you want to do some kind of consulting and you have a good network, you can probably make money faster than if, say, you wanna start a store/restaurant or a small manufacturing business or monetize your hobbies.

    So, do seek some therapy, and also, if you decide to strike out on your own, avail yourself of all the free (or very inexpensive) help that exists! SBDC, CareerLink, councils of governments, IMC, six sigma, whatever other resources are local to you and relevant to your industry! Make sure you start with a solid business plan and projections, and get some funding!! Or, like others have said, make sure your partner is on board to support you and the fam while you work your face off to get shit started.

    Good luck!

  15. Anonymous

    I know exactly how you feel! I was working for a very toxic company and purposely got myself fired so I could collect unemployment benefits. It’s an idea so you can have some funds saved up to start your next business venture. Even working a part time job remotely works while also planning your next moves for your small business and how you want to run it. There’s always a lot of growing pains, but overall I’m happy consulting and you get to manage your time better. (Take vacation time and breaks when you want to!) I only work about 20 hours a week but still supplement income from other streams which is important if you end up having a few hard months.

    Good luck and much success! :)

  16. Kate Wade

    Some people just like being their own boss. That said, being your own boss also means a lot of self discipline. I don't know what the difficulties and particular conflicts you had with former bosses were, but make sure you seriously reflect on if those issues might also come up if you were independent. For example, if it was things like trouble making deadlines, prioritizing key tasks, staying organized - that might become a larger issue if you are independent. Finding a boss that you have better chemistry with might be a better solution.

    All that being said, if after reflection you decide you want to try to be independent and can risk it even temporarily, now is the time to do it. Since so many are trying it, having a 6 month-1 year "independent freelancer" section on your resume doesn't look like "I just couldn't find work so I put this in" as it used to. If you don't have paying gigs, write blogs, do projects for needed non-profits, etc., between business development work. It is also a great way to contract with a company and test the waters to see if you find the right chemistry with a team/future boss that you might want to got back and with with full time.

  17. Anonymous

    Hi, I understand how you feel. I think you did a right thing but maybe the timing wasn't right. You'd happily settle for the misery of working for assholes who don't value you - but for how long?

    Your life will feel better. Most of people believe that their fate is unique and most miserable. But guess what, there are also other people who are without a job and others who have bigger amounts of debts. Chin up! Being hard on yourself is not gonna help you with find a solution.

  18. hello

    You're so right... Thank you -- needed to hear that!

  19. rgstaffing@bellsouth.net

    If you can't get along with your bosses, you are more than likely going to have the same problem getting along with your clients. Having your own business is more demanding personality wise than working for someone else. I would dig deep and come to terms with why you can't get along with your bosses without blaming them.

  20. Anonymous

    I came to say this, or at least to ask - have you taken an honest look at yourself and your potential role in the conflict also? Is it a boss that everyone has a problem with or just you? I'm not blaming you but owning a business isn't an escape from needing to interact with people and/or perhaps lead others if you grow your business. If you're not satisfied with working for someone I wish you the best to make a change but also be aware you need to walk into any situation eyes wide open and own your strengths and weaknesses.

    I've lead people for years and some people are really blind to their actual performance or the way they are perceived. While it's not my responsibility to manage others emotions, etc. it is still necessary to understand how I am perceived by others.

    Whatever you choose, I hope you are successful and fulfilled. :)

  21. Julie Wozniak

    Go for it!

  22. Jasmine Powers

    Congratulations for knowing that there are options and other ways for earning a wage.

    As the other commenters pointed out, a business is hard (but also very rewarding). The clients and customers are your boss now and so you end up with a lot of bosses.

    I think a lot of us struggle with our bosses and may even have a personality that adds to the challenge.

    My only practical recommendations are, look into Dialectical Behavior Therapy because it’s a form of therapy that teaches distress tolerance and how to help you deal with life as it is.

    Then read Kim Levine’s Mommy Millionaire to see an amazing entrepreneur story chock full of all the challenges she faced. This will help you see that entrepreneurship is viable but also not an escape from what you may be feeling.

    And keep pressing forward. Whether you change jobs or stay, start the business on the side and get a taste of it. Try different businesses too because one business model may be better suited for how you see yourself (for example consulting or e-commerce versus hairstylist).

    Either way, you’ll land on your feet.

  23. Wurdah Iqbal

    Good decision sister. I was also the teacher; due to unhealthy environment,I left my workplace and now I have joined a platform where I start my own business. Feel free to contact me if you need any guidance or advice. My name is warda And I am from Pakistan.

  24. Eboni Marshae

    ...on my team, there are 18 people. We are having this conversation almost daily. If you can get out, by all means!!! RUN!!!

  25. Anonymous

    I'm with you. We share the same sentiments. I have been seriously pondering the same question. I think you should bet on yourself and take that chance. I have decided to move on within the next few months. You got this, sis!!!

  26. Creativa Graphics

    If you have a passion for something, or still don't know what you want to jump into...my advice is to make a plan, have a strategy, and go for it.

    I have worked for myself, then jumped back into the workforce, and am now back on my own. I am stress-free, have the satisfaction of picking and choosing my clients and genuinely have regained a new passion for my craft (I own a graphic & web design company).

    The passion is only amplified by having the satisfaction of building something from nothing and knowing each day you got this! Good luck and enjoy your journey!

  27. Anonymous

    If after 7 years and multiple bosses, you're still having difficulty with reporting hierarchy, maybe unpack why and examine your own behavior. Of course, starting your own company can be rewarding and exciting but it comes with its own struggles, ones that may not be worth it if getting away from bad bosses is the only reason you're leaving

  28. Anonymous

    I was going to say the same thing. If you are having issues with multiple supervisors and you are not happy reporting to anyone, you may have a personal issue with authority or other internal factors that are playing into that.

    If you are considering leaving where you are, I would only do that if you have stable income coming in from your business. That usually takes time because you will need to build your clientele and establish and build your brand. Once you have enough income to pay your expenses, put in a two week notice and leave. This way you will set yourself up for success and not burn any bridges.

    Good luck!

  29. Annalise M

    I hear you and think this is a valid way to feel. I would offer to think carefully about what type of business, because you might be trading one devil for another in terms of managing your own employees.

  30. EMILY KIKUE FRANK

    Look into some business coaching to ensure your business is sustainable and profitable. If you're in the US, look for your local SBDC.

  31. Anonymous

    Depends upon what you want to do. If you have a skill set that requires a professional license, at times there can be conflicts and differences in style that may rise to the level of possible professional liability exposure. In that type of situation you have to make a decision in a effort to protect your licensure, your ability to make a living and your professional reputation. That said, going out on your own is never easy at first, but ultimately it can be extremely rewarding.

  32. Priscilla

    Stay employed for as long as you can right now, try carving out an afternoon on a weekend for example to start your side "hustle" , biz plan, action plan. I spent 9 months working for a company that was awful, although I really enjoyed the people that I proposed contracts to, and built good relationships there, which helped me maintain my composure with the corporate management. Saved 50% of my paychecks, worked on my side hustle every weekend for 4 hours minimum and when I just couldn't take it any more, I left but had my new business foundation together. Don't risk everything just yet, it is really hard to get a new business going and there are many times when I have paid everyone else except me.

    Just saying, be smart about it. Congratulations though on the desire to do so. I know the difference now between working with good people with integrity and ethics versus not. Hope all goes well for you in 2024. All my best.

  33. Anonymous

    I’m older than you and have found myself in the same boat, except I’m out of work. Additionally, I’m disabled on 2 fronts.

    Here are some things I’ve faced:

    1. I worked for a racist partner at my first office job. She told her other secretary she was nicer to the other girl hired alongside me b/c she reminded her of herself at that age. (They were both blue eyed, blonde haired. I’m Asia. The other Spanish secretary told me flat out: This is racism!)
    2. I liked my ERISA compliance job 15 yrs ago. Didn’t like the antisemitic owner. Also didn’t like that the firm was 90% Italian and refused to teach me anything outside my job description. eg: Testing
    3. Moved onto doc reviews with Epiq where I was made fun of every day. Made fun of my hair, my size (I’m a little person), my skin (sensitive, break outs a lot) and for wearing an insulin pump. At Epiq, I was also followed twice! Reported once and was called a liar and mentally deranged.
    4. During COVID had the opportunity to move into finance. Working side-by-side with the 4%. Elitists - they actually thrive on it. Add to the fact that attorneys are now moving into the field b/c law is oversaturated. There was one who would actually lied when asked any question.
    5. The last bank I worked with had a manager that was discreetly accusing me of doing the work wrong when she hadn’t even given me work yet. She would yell things at me, like, “You had better not copy and paste. I’ll know!” When my desktop wasn’t setup properly for my work she started yelling: “You, you, you. Click, click, click. This is all your fault!” (It wasn’t. I’ve been through this before. My desktop wasn’t set up properly b/c she didn’t give the IT team permissions.) Btw - she was acting this way b/c I don’t speak Chinese. The job didn’t need it b/c foreign docs have to be translated into English and documented.

    Btw - for the last bank job I wanted to leave the first week. Stayed a month…to this day still don’t know if I quit or if this vile woman fired me after I told my rep I didn’t want to come back. (Needed the money regardless…it paid rent for a month.)

    Since then, I realized that I’ve become feral. Bad environments stay with you whether you like it or even realize it.

    Everyone is correct in saying that you will need a plan of action. You will need emergency money socked away.

    You will also need some introspection. (While on a wfh review, I realized I became feral. Why? We had room attendants that weren’t actually answering our questions. It pissed me off b/c first and foremost, they’re paid a helluva lot more than reviewers. 2nd, most of them are attorneys. 3rd, just like any law firm, they have sway over reviewers. Reviewers are 1 in a 1,000. We get dropped all the time. 4th, not giving any answer or a proper answer cheapens the integrity of our work. 5th, not answering often means the same question will be asked again and again and again. Did I have the right to get pissed off? No, absolutely not. However, the 4th & 5th bullet point should say it all.)

  34. Anonymous

    Your post was hard to follow. What do you mean by you became "feral?" Were you like a wild animal?

  35. Anonymous

    Exactly! If you’re snapping and friends and family for tiny things. If you get a WFH and get upset b/c your QA doesn’t entirely understand what you’re doing. That is feral…especially at friends and family.

    My apologies if you’re not the person that posted. If you are, take a hard look in the mirror.

    Would I go back to any of those jobs? Yes. The ERISA compliance. I knew my work inside out! It wasn’t difficult. After GUST reinstatement, it may have become part-time. 800 client files were in Compliance b/c of me.

Fairygodboss VIP
Achieve your career goals.
Be part of the largest online career community for women to find jobs, advice, and support — for free.
Fairygodboss members