Should you Choose Self-Employment Instead of a Boss?

Should you Choose Self-Employment Instead of a Boss?

Total Reading Time: 4 minutes

There’s positives and negatives in life and what we try to do is narrow down the negatives before making a decision. I remember my own decision many years ago to work for myself or look for a 9 to 5 job. Before that, I worked in corporate jobs. The last one I had was being eliminated and I did what most would do in my place…look for another job! My search wasn’t going well though. One day, I received a phone call from a dear friend who asked me a poignant question…

“Would you like to freelance full time?”

I was stunned at first because yes I dreamed of working from home, but I just dismissed that thought as being not possible. To make a long story short, she worked for a new company that didn’t have the manpower to handle their administrative projects and they had many branches that needed this support. They were willing to outsource all these clients to me. All I had to do was decide if freelancing was really what I wanted to do.

NOTE: I’m using the term “freelancing” throughout this article, but there’s a difference between freelancer, business owner and entrepreneur. To me, I’m interchanging these terms to mean self-employment but if you want to compare these, follow this link ( to read an excellent article which breaks down all three terms.

If you’ve considered working for yourself but dismissed it, don’t throw the idea out just yet! I have learned almost anything is possible if you really want it. Working for myself meant “freedom”. I could choose my own work hours, I could choose how much I wanted to charge for my skills and experience. And, I could choose my clients. Being transparent, I’m not a 9 to 5 kind of gal! I need flexibility in my schedule. There are days when I will work from sun up to sun down, other days I may work a couple hours in the morning and then work through the night. I like having that type of schedule, you may also want more flexibility in your schedule.

Some positives of freelancing

  • Flexibility. You can control own schedule of how you work the hours you need to. And, because you can plan out your day, it frees you up to pursue other interests, have more time to spend with your family, or if you volunteer. You can even plan your vacation time whenever you want.
  • Freedom. To add to what I mentioned above, freedom is such an awesome privilege and as Americans we understand how precious it is to be able to choose.
  • Sense of Accomplishment. When I create…a flyer, web page, or an ad and it really comes together, I feel such a rush of joy. To be able to add something great to the world brings with it a feeling that you don’t always get on a job. I remember being told, “if the boss doesn’t say anything, you’re doing alright.” I really didn’t like that because I like feedback. I want to know if I’m not doing a job correctly and before receiving an annual review. I believe people want to know they’re valued and it’s nice to hear it. When you work for yourself, you appreciate the work you do and your customers will see that. 

Not-so-positives of freelancing

Considering the “not-so-positives” should also be part of your decision. You don’t want to go into anything head first. So, let’s look at these and see if they can be turned into positives.

  • Insurance, taxes, bookkeeping, legal. These are important because as a freelancer, you are responsible for all four of these tasks.
  • Insurance. As an employee, your company takes of this but what about freelancers? Well, not to worry. There are health plans specifically designed for freelancers. You can ask your healthcare provider about this if you’re considering self-employment.
  • Taxes. This was the one “negative” I dreaded when I started out freelancing. I had to get used to holding all my receipts and deciphering which ones were for business, categorize them and enter amounts into a spreadsheet or software. I’m not good with numbers. So, I hired a tax accountant and that was a HUGE help. I definitely recommend this.
  • Bookkeeping. As I said, numbers aren’t my thing. But thank goodness for Quickbooks. If you are going to be working alone, you will want to invest in some kind of  bookkeeping software and designate a day to just keying in your expenses, income, etc., to keep up with this. Then, it won’t be so overwhelming come tax filing time.
  • Legal. I think this is important to at least get some advice. There are several types of filing status for freelancing and you’ll want to know which one will best for you. I happen to be a sole proprietor and the chamber contracts with me. There are pros and cons with business types too, so you’ll need to know this before you quit your day job. And, what’s great is that many lawyers will sit down with you for free or low cost to give you sound advice.

When I made my decision to go solo, I also sought advice from other business professionals and I read articles from other freelancers. I also think seeking opinions from your support system is key. Working for yourself is a major lifestyle change and you want to be sure the major people around you will be supportive. 

Here’s some other resources to look into that might be of further help:

  • – website dedicated to the freelancer. 
    The site carries news stories about entrepreneurship, small business management, and business. The magazine was first published in 1977. There’s also a section dedicated to women business owners.
  • – site owned by Darren Rowse, a full time blogger. Problogger helps other bloggers learn the skills of blogging, share their own experiences and promote the blogging medium. and Darren even started a podcast. This is a good site to bookmark if you want to use blogging as a promotional platform.
  • Smashing Magazine – I’ve followed this site for many years. If you’re in the design industry both website and graphics, you’ll find this site really helpful.
  • Website Magazine – for the techies in mind, this site has up-to-date articles on all things happenings in the website and technology world. They put out digital and print editions.
  • Forbes – Their site has a section entirely dedicated to entrepreneurs. It contains news, analysis, advice and information on starting and growing a small business.

I am very happy with my decision to be self-employed. It wasn’t easy, much like buying a home, but at the end of the day it is quite satisfying. I wish you much success in your career endeavors.