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Guest Blogger: Ashley of AfterNineToFive

I asked my blogging friend Ashley, of After Nine To Five, to guest post and share her words of wisdom on being self-employed. I’m sure this is something that a lot of us (myself included) dream of. But while we have our heads in the clouds, Ashley is here to bring us back to reality and remind us that it’s not always fun and games and it takes a LOT of work!

When I first transitioned into being a full-time small business owner, I only saw the positives. The ability to work when I wanted, not answer to anyone, not have someone screaming at me for something I never did, being able to work in my pajamas… the list goes on and on. Three months into quitting my corporate job, I was still very near to the bad side of working for corporate America so everything seemed great. But as time went on, I realized that while their are many pros to being self-employed, there are still many cons.

So today I wanted to share with you the good, the bad, and the ugly parts of owning a small business:

The Hours

  • Good: You can work whenever you want which means morning, afternoon, or night hours can be split however you want them to be.
  • Bad: You will need to work extra hours if you do not have help as there is no one else that can do the work for you.
  • Ugly: You are more than likely going to work more than forty hours per week. Much more. On a regular basis.

Vacation Time

  • Good: You can take vacation whenever you want – whether it’s a day here and there or a whole month. You decide.
  • Bad: You’ll have to make sure you are caught up beforehand and will not be able to pass your work off to anyone else so you may be swamped when you return from you vacation.
  • Ugly: You could easily find yourself working through a “vacation” if you don’t have assistance.

The Money

  • Good: Every day has the opportunity to be a pay day. You can earn even more based off of how much effort and time you wish to put into your business.
  • Bad: Most of the time, if you calculate out your hourly wage, it will not be pretty. Especially in the beginning. Sometimes you will feel like you did a massive amount of work for absolutely no gain.
  • Ugly: There may be some weeks where you may not get paid at all and if you’re not prepared for it, it sucks.


  • Good: You have more freedom now than you have ever had before. Creative, personal, financial – the list goes on.
  • Bad: Freedom to creative and change up your business can sometimes be overwhelming by having too many choices.
  • Ugly: If you’re not disciplined, you’ll accomplish nothing. And you’ll likely have no one to blame but yourself.

These are things I try to balance on a daily basis. The good comes with the bad and makes it bearable, but some days the ugly is just enough to make me question if I made the right decision. All I need to do is remind myself of what I hope to gain in the long-run and the strides I’ve made so far to know that I did in fact make the right choice.

Thanks so much for a behind-the-scenes look at being an independent business owner Ashley!

Join the discussion 4 Comments

  • J.Crabbit says:

    I like this good bad ugly format, and I totally already follow ashleys blog. Great guest post!!

  • Venassa says:

    Being self-employed seems a little terrifying to me, but I really admire you for doing it! Overall you must feel so much more proud of yourself than you would working for someone else.

  • This is so true! I do copywriting for a lot of self-employed clients and work hands-on with the owners of small businesses, and we are often on the phone many times a day at outrageously quacky hours completing a project.

    You gain a lot, but you also make some sacrifices… especially in the beginning!

    Thanks for posting this!

  • Heather says:

    I dream to be self employed one day, so reading this was really helpful! 🙂

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