Pros and Cons of Being a Self-Employed CEO of Me

I have been 100% self-employed and living the CEO of Me® life for a long time now (since 2016). I have a lot of people tell me they don’t know how I do it or that they don’t think they could do it.  I also have a lot of people ask me to share my secrets to success.  That was part of the inspiration for starting this blog over a year ago.  I am excited to finally be starting on a series of articles all about how to be a successful CEO of Me®.

While being self-employed is very rewarding, there are a lot of things you need to consider before starting your own business. Being self-employed is not for everyone. Below are a few pros and cons you need to consider before beginning your journey to be a CEO of Me®.


  • Set your own hours each day / week, no 8-5 time clock
  • Being your own boss and in control of your career and life
  • Put your family first, ability to be there for your kids’ activities and to watch them grow up
  • Opportunity to make unlimited income
  • Minimal monetary investment needed to start your own business
  • Working from home
  • No office or corporate politics to deal with
  • Save money on gas, wear & tear on your vehicle and also save money by not having to purchase expensive work clothes
  • Support, recognition, friendship from others in your business or field
  • Being able to make a living doing something you love and feel passionate about
  • Having a business of your own is something you can take pride in and feel a great sense of accomplishment from
  • Ability to show your children/friends/family that they can also do anything they put their mind to
  • Use your talents and skills to the best of your ability
  • Terrific tax benefits and deductions you can take advantage of as a home-based business owner


  • Must be disciplined enough to actually work your business and put in all the hours necessary to run a business as it may take more than 40 hours a week when you are starting out.
  • You will need determination, drive, passion, energy and commitment to be your own boss
  • Must be able to work with kids in the house or find ways to involve your kids / schedule your work and still work
  • You may have to invest a huge amount of time, energy, sweat and even tears before you begin making a significant or full-time income
  • No long commute, but you still need to get up, get dressed, have an office area and actually work each day
  • Friends and family who may not understand or support your self-employed venture
  • You will need to believe in your dream, your business and yourself more than anyone else does
  • Having to play all roles of a business – CEO, secretary, accountant, customer service, shipping department, conflict management and maybe even the janitor too.
  • Your income will change every month and some months will be better (or worse) than others
  • You will need to provide your own insurance and invest in your own retirement plan
  • May need to purchase a new computer, software or other electronic products
  • If your business includes making a craft, handmade item or selling a product, you may need to purchase inventory or supplies.
  • You may need to purchase a business license in your town or county, may need to consider filing for an LLC or trademark.
  • Space for a home office and / or storage area

I hope the cons don’t scare you away.  The rewards you will gain from being self-employed are worth so much more than any of the negatives.  The bottom line is that if you are willing to sacrifice a little time, energy, sweat & money, you can get back a huge reward, financially, emotionally and mentally in the long run!

What about you, are you or have you ever been self-employed? Are there any other pros or cons you have experienced? Feel free to comment below and share your thoughts and experiences!

  • Thanks for the pros and cons. It takes a lot of work to be self-employed, I definitely need to work harder at my organization and motivation.

    • thanks Katherine! Good luck on your journey! Be sure to check back for future posts in this series. There are a lot of sacrifices/cons but the rewards are always worth it!

  • That’s a great list. I definitely see it in myself! It’s sooo good and sooo frustrating sometimes! People just don’t get how much work it takes. But it’s well worth it at the same time.

    • Yes I still don’t have insurance so that’s been the biggest sacrifice for me… However there are decent insurance plans most people can get. Due to pre-existing conditions insurance for me is just too expensive right now… Once I am debt free I will be getting insurance though!

  • This is a good list. Sometimes I’m amazed by the ppl that think self-employed people don’t have to work! I think they get the same bad wrap as Stay at home moms that ppl think sit around and watch tv all day…not running after kids is hard too.

    • I know and a lot people don’t understand how I can’t just meet them or go whenever, whereever… Yes my hours are flexible but I do work still, lol…

  • Love the series! I don’t have health insurance delivering so luckily? that won’t be a change here, if can ever get to where you are and be 100% self employed.

    • Health insurance is one of the big cons. I still do not have health insurance 6 years later… I could get it but due to pre-existing conditions it is just too expensive for me right now. Once I am debt free and have extra funds I do plan to get it. There are many somewhat affordable options for insurance out there if you don’t have pre-existing conditions…

  • Yea I don’t have pre-existing conditions (at least diagnosed) so would be easier, but just can’t justify spending $100+/month on insurance when, like you, I have debt to pay. So instead roll the dice and hope any injury that happens is when out delivering so at least under workers comp. Eventually though we are all going to be shafted and forced to pay for insurance or fines 🙁

    • I totally agree. I spend very little going to the dr each year, so for me to be shelling out $300+ a month for health insurance does not make sense financially. Honestly I don’t mind paying a “fine” for not having insurance IF it means I can get affordable medical when / if I need it… But I doubt that will be the case…

  • Oh yea, if it meant lower rates I would be happy too, but think that only means while coverage can’t be denied they don’t have to make it an affordable rate. Know they have provision that if can’t afford insurance won’t be fined, but didn’t who decided that. For those of us that make decent $ but also have debt we will probably be forced to get it and in turn to stall or reverse the debt reduction process. Wonder what kind of provisions there will be for people that only have income that is from having their own business and that in turn can have variable income each month.

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