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Being a Boss, The Good, The Bad, and The Ugly

There were a couple of posts recently about the benefits of being an employee. For that point of view, check out DC’s post at Young Adult Money or Holly’s post  at Club Thrifty. I have not been an employee for over ten years. I bought my optometry practice in 2002 and have been the boss ever since. I’d like to share my opinion on the ups and downs from my time as the head honcho. Maybe you can gain some prospective in determining if you would like to be in charge or if it makes sense to remain an employee. This is my experience of being a boss; the good, the bad, and the ulgy.

The Good

  1. Making my Own Schedule. While my office is open five days per week, I can determine when I want to be there. I’ve changed my hours several times over the years. If I want time off, I can work  longer on another day. As long as I see enough patients, it doesn’t really matter what day or times.
  2. Vacation. I can take vacation whenever I want. I don’t have to get it approved or see who has seniority before I ask for time off.
  3. Dividend Income. I pay myself a salary, but if the business is doing well, I can take extra income as a dividend. Taxes are lower on dividend income, and it has been great for supplementing my normal salary.
  4. Employees. I usually have 6 full time employees plus a part time book keeper/office manager. Our head optician has been there for 30+ years. While I did not hire him, I have contributed to his quality of life. If you are trained in how to use ophthalmic equipment, it is a skill that can translate to any area of the country. It feels good to provide jobs and teach skills.
  5. I can provide service as I see fit. I love medical optometry, and manage anything that doesn’t require surgery. In some chain opticals, you dont’t have the correct diagnostic equipment for medical problems, and you have to turn out a certain volume to meet your contractual obligations. You’d have to refer anything medical to another doctor. I like to take time to get to know my patients. It also helps me figure out what they require as far as eye care needs. If I had to spit them out every 15 minutes, that doesn’t leave much time for conversation.

The Bad

  1. It’s 24/7. Since I run the business, I have to take work home often. I have a book keeper and accountant, but if you don’t understand and keep up with your financials, you can get in trouble fast. I also have never had a vacation where I didn’t get a call about something.
  2.  The Buck Stops Here. No matter how bad someone screws up, even if I am not in the building, I am responsible. I have a great staff right now, but mistakes happen. I have to put out lots of fires.
  3. Taxes. Small businesses get eaten alive with taxes. Just recently, we had to pay more unemployment taxes because the state had used up it’s reserve. I try to remind myself that if we didn’t make money, we wouldn’t owe taxes, so it’s a good thing. However, that’s a hard argument to win.
  4. I’m always on call.  I don’t mind the patient emergencies, but if a pipe breaks, the alarm goes off, or our sprinklers are going crazy during hours you aren’t supposed to be watering, guess who gets called?
  5. Decisions. As a small business in a small town, we get daily requests to sponsor something. I can’t honor every request. You are always making someone mad if you don’t donate to this fundraiser or sponsor this team. If I was an employee, I could tell them that I’d have to check with the boss.

The Ugly

  1. Mad Customers. I’ve been yelled at over the years by a number of angry customers, ususally over a bill that insurance didn’t cover. While it is not my responsibillity to know what your plan covers, somehow I tend to get blamed, not the insurance company.
  2. Employees. Yes employees can be good, bad or ugly. This is the worst part of being the boss in my opinion. I have had to fire five people in the past 10 years. One was a flake and didn’t care. The others knew it was coming. Employees who know they are getting fired do one of two things in my experience. They either rile up the other employees and make them feel vulnerable, destroying any rapport you have built, or they suck as much as they can out of you while doing very minimal amounts of work.

The last two employees that I had to fire turned out to be real gems. One was angry when I hired a new office manager. I’m not sure why, maybe she thought she should have gotten the job. Anyway, after she slammed my door so hard it broke, we had to let her go. She filed all kinds of complaints with various agencies. Since she was a white female under 30, and I am a heterosexual woman, she was not able to declare race, gender,  age discrimination or sexual harassment. She did, however, say she was bullied due to her religious beliefs, which was funny because she didn’t practice any religion I knew of and didn’t attend church.  She also said we violated patient’s privacy and that she tried to tell me, but I fired her instead of correcting the violations. It was all bogus, but I still had to get an attorney and prove we were not in the wrong.

The last one I had to let go broke my heart. I hired her when she was 19. It was her first real job, and she did great. I paid for her to take a year long course to become a certified ophthalmic technician. She found a lousy, criminal boyfriend, had a kid, and just went on a downward spiral. She actually took my office credit card and went shopping.  She was pregnant again when I had to fire her. I had to get the attorney help make it clear she was getting fired for stealing, not for being pregnant.

Aside from the ugly, I have enjoyed my time as a boss. I am burned out from the all consuming nature of the position, though, and am selling my business at the end of the year. I’ll get to be an employee again, and we’ll see how I do after having my way for so long. If you want to be your own boss, it has many rewards, but it’s not all roses. You have to account for the good, the bad, and the ugly.

Do you want to be your own boss? What would you buy with the boss’s credit card?

About Kim Parr

Kim Parr is a private practice optometrist, freelance writer, and personal financial blogger. You can follow her journey to 20/20 financial vision at Eyes on the Dollar.


  1. You say the good is about free schedule and vacations, but do you actually take that free time? Can you go away for a full week and really be on holidays with six employees?
    Stealing is something I would be afraid of, I am my own boss but work alone, and have heard all kinds of horror stories about people stealing money or goods. My friend owns a bar and the bartender used to bring his own bottles and have people pay cash.
    With my boss’ credit card, I would buy a one way ticket to a tropical paradise on my last day at work and never come back!
    Pauline recently posted..France or Guatemala, three real-estate optionsMy Profile

    • It depends on the staff I have at the time. Sometimes they are very proactive and can deal with problems as they arise. Some call me with every little detail. I didn’t take much time off in the beginning, but I do now. It’s sometimes a pain to come back to, but you have to take the time off. I think the one way ticket is a good idea. Just go somewhere that doesn’t have extradition laws!

  2. Great post! My wife and I run our own business, so I can relate to a point. We love being our own bosses and doing things the way we see fit. But, you’re right on when you say you’re on call 24/7. The big thing we’ve learned is knowing when to call it a day, otherwise we’d always be working. We run ours out of our house, so it’s important to have the separation between work/life. You can’t always have that in running a business, but it’s important to do what you can to make it possible. I also agree on the taxes, they’re just nuts. We pay estimated taxes and it’s painful to write those two checks each quarter.
    John S @ Frugal Rules recently posted..I’ve Joined the Yakezie Challenge!My Profile

  3. Thanks for mentioning my post at the beginning of the article. I really enjoyed reading your opinion on this topic as you have been a small business owner for so long. I referred my friend to your site a couple times as he is in the process of opening his own office.

    There seems to be so many pros and cons for both sides, but I also wonder how hard it would be to go from being an employee to being a small business owner and then back to being an employee? Anyway, great post!
    DC @ Young Adult Money recently posted..What are Health Insurance Exchanges and How Do They Work?My Profile

    • I’ll let you know in about 6 mos. I’ll still be the landlord and advisor, so I bet it will be just fine. Tell your friend he can email me if he ever has questions. If I haven’t seen it or dealt with it, I probably know someone who has.

  4. There’s no perfect scenario. Search as one may… life has its ups and downs.
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  5. I can’t believe those stories about your employees. Stealing would definitely be a huge fear of mine if I ever had employees (which I probably never will). Crazy that even through all those bogus allegations, you still had the pay the lawyers.
    Rebecca recently posted..7 Ways to earn some extra cashMy Profile

    • I’ve learned to just let the legal pros handle stuff like that, even if it does cost a small fortune. There are just too many CYA things I don’t think of.

  6. Kim, your comment on employees who see it coming (about to get fired) reminded me of a famous startup owner’s quote. Although not his exact quotes, but it went something like this “when you spot a rotten apple, throw it away instantly before it spoils the whole batch.” This was one of the comments made looking back at the challenges the company faced in its early days.
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  7. Wow, those are some crazy employee stories ! It’s ridiculous what bitter people can do. I’m not sure if I want to be my own boss, there are definite upsides and downsides to each, so I am just planning on seeing where life takes me. If I end up in a job I love, I won’t leave, but if I feel the need to start something on my own I am definitely open to it.
    Gillian @ Money After Graduation recently posted..I hate making payments against my debt. So I got rid of the debt.My Profile

  8. I’d rather take those downsides than let go of any of the upsides you’ve listed! Many bosses I’ve had are horrible and don’t understand that being in charge doesn’t mean you’re infallable. I’ve had some great leaders over the years who were wonderful and inspirational. My goal every day is to be like them with my employees.
    AverageJoe recently posted..Two Guys and Your Money #13: How Wall Street Became the Capital of CapitalMy Profile

    • I see myself being more of a mentor to the doctor who is taking over my practice. I just won’t have to deal with the day to day headaches. I might miss it at some point, but there are always leadership opportunities if I am motivated to go in that direction.

  9. Oh my…those stories about the employees are terrible. I’m not sure I have the stones to fire somebody; especially if it wasn’t their fault. At my previous job, I was in sales and basically directly responsible for keeping 60+ people employed. However, each winter things would slow down and many of them had to be laid off right before the holidays…it was pretty awesome and I’m glad I wasn’t the one that had to tell them.

    Lets preface that last question with: IF I knew I wasn’t going to get caught, I would buy: a new bed, couch, TV, computer, and a few new suits. LOL. In reality I wouldn’t be foolish enough to do such a thing. That’s nuts! Did you get your money back?
    Jason @ WorkSaveLive recently posted..Blog Income and Site Statistics - September 2012My Profile

    • Luckily, I have never had to lay someone off for purely financial reasons. I never sleep the nights before I have to let someone go.
      Yes, I took the money out of her last paycheck. I could have sort of understood better if she was buying diapers and milk, but it was insane stuff like makeup, gardening gloves, cargo shorts. She hid the credit card statement, so we got it online. There were all these charges,s o we called the store and they were able to generate a receipt based on the transaction #. That’s how we got the itemized list. Crazy for sure.

  10. Although I don’t own the business, I’ve been a boss for a long time now and I can identify with a lot of these. It’s not all its cracked up to be. Especially when you have to fire people. Then it really stinks. However, I do like making my own schedule and having the ability to figure out how to best handle customers.
    My Money Design recently posted..Do You Flaunt It?My Profile

  11. I always try to weigh the pros and cons. Nothing is ideal. I have a lot of autonomy where I work but the direction constantly changes and there is no communication which makes things really hard. I like the people I work with though and the flexibility so I don’t think I am going to make any changes right now.
    Miss T @ Prairie Eco-Thrifter recently posted..6 Ways to Improve Your MarketabilityMy Profile

    • I hope it continues to work for you. That’s hard with no direction. As a boss, I am sometimes guilty of not speaking out much until something goes wrong. I have to constantly remind myself to use positive reinforcements.

  12. I’ll be interested to hear your journey about selling your business, if you’re able to disclose of course.
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  13. Fascinating post into the world of a manager of a small business… Love it. I can imagine how to tough it would be to let someone go, especially in a small town where everyone knows everyone..

    I had no idea that businesses were asked to sponsor charity events so frequently!… Certainly you can’t afford to support them all.. How do you let them down gently?
    jefferson @SeeDebtRun recently posted..America’s Worst Warranty - Why I Will Never Buy Another HyundaiMy Profile

    • It is difficult to see the lady who tried to sue me when I’m picking my daughter up from school. Hopefully, we’ve both moved on.

      It’s usually the small businesses who get asked. Big Box stores have lists of things they donate to charity, but usually not locally unless you give them tons of notice. I try to support people who are patients of mine and if it is a cause I support myself. People tend not to realize that if they buy all their products online to save $10, I may not be able to sponsor their son on his drama trip to Scotland. Within reason, if you can support someone local, they are able to put more back in the local economy. I usually just tell people that my charity budget has already been met for the month, which is usually true!

  14. Thanks for sharing these stories. It really made me think twice about the idea of running a business! A lot of ‘soft’ skills are required huh?! It also makes me so mad how easy it is for people to take legal action your side of the pond. In the UK it just doesn’t happen!
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  15. Doing Job is much easier compared to business but when you run business on which you are passionate makes you strong and help you easily overcome from problems.
    My business has made me strong and helped me find my capabilities.
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  16. Do I want to be the boss? No, not really. I just want to make money. I like being an employee.
    Holly@ClubThrifty recently posted..Why People Aren’t Buying Life InsuranceMy Profile

  17. I’m definitely interested in hearing your experiences when you go about selling your business. Since we attempted to be on the buying side of a small business once, I’m totally curious about it from the other end.

    Also I can’t believe that employees used the company credit card for personal items. That’s insane.
    Mrs. Pop @ Planting Our Pennies recently posted..Rewards Cards And Holiday MoneyMy Profile

    • I have a post in the works on owner finance when buying or selling that will probably come out soon. I thought it might be too boring, but there was just nothing out there to help me when I tried looking online for similar situations. I will probably update on the financial and emotional side of it at some point as well.

      Employees do crazy things. I have learned to never be surprised.

  18. I’m a fairly, shy introverted person and not very good with confrontation, so I don’t think I’d be a very good boss. I’ve never had a management position. I’m not sure people would take me seriously. I like the idea of making your own schedule and being able to take vacation when you want, but dealing with bad employees and other BS would be a pain.
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