4 Common Mistakes Made By The Self-Employed

I’ve been fully self-employed for almost a year now (side hustled for 3 years) and I have learned a lot over this time period. No, I’m definitely not an expert but I do know a little bit about owning businesses and running them since that’s all I did when I had my day job as a business…

Michelle Schroeder-Gardner

Last Updated: October 31, 2021

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4 Common Mistakes Made By The Self-EmployedI’ve been fully self-employed for almost a year now (side hustled for 3 years) and I have learned a lot over this time period.

No, I’m definitely not an expert but I do know a little bit about owning businesses and running them since that’s all I did when I had my day job as a business analyst.

As a quick summary, in my old day job some of my responsibilities included conducting interviews to learn more about a company and how they operated, analyzing any legal and business agreements, reviewing and/or compiling financial documents (including tax returns, financial reports, etc), and so on.

When I had this position, I saw some really amazing companies. I saw many companies where the owners completely started from scratch and built multi-million dollar companies which were extremely successful.

However, I also saw many, MANY companies that made some horrible mistakes. These companies operated at losses each and every year, and I just don’t know how they did it.

Even though I run a fairly simple business (all I need is a laptop and internet to work), I’m starting to understand more and more about what these business owners went through in order to get to where they currently are.

I’ve also made my own fair share of mistakes, and I know no one is perfect. Hopefully, you can avoid some mistakes though!

Below are four common mistakes made by the self-employed:

 

1. Not being organized.

This is a very common mistake made by the self-employed. I’m guilty of this one too.

I make this mistake all the time, but I am trying to improve. When you have your own business, you really need to work on being as organized as you possibly can.

You need to make sure to keep your personal and business finances separate, receipts organized, papers organized, and pretty much everything you use for when you do your taxes the following year need to be prepped and organized.

Keeping everything organized will help everything go much more smoothly when you eventually need the item. It’s easy to let each little thing slide and all of a sudden your disorganization will take over your life.

It might become impossible to find anything, and you might even lose important documents.

 

2. Thinking being self-employed will be easy.

Now, this one isn’t necessarily too common, but I do think it’s a common way that people who are NOT self-employed think.

I recently read an article about someone who quit their job and entered the self-employment world because they wanted to do something easier in life. Sadly, they found out the truth was the exact opposite.

Being self-employed isn’t a never-ending vacation. This is something too many people think. Just because you work for yourself and/or at home, it doesn’t mean that life is automatically easier.

You will need a plan for your business, research about how you will actually make an income, organize your finances, handle the legal side of owning a business, manage to not let your business takeover your life, provide services, sell products, find health insurance, save for retirement, and so on. Oh yeah, and don’t forget about taxes!

 

3. Not having an emergency fund.

I have seen too many people enter the self-employment life, only to have a few bad months and completely give up. I understand that running a business can be hard (see above), but I do think having an emergency fund can be a lifesaver in many situations.

Different people like to have a different amount in their emergency fund. I have a full year of expenses just in case everything completely tanks, or if something major happens to either of us or our home. Keep in mind that we do have a $12,000 deductible before we can actually use our health insurance, so we keep our emergency fund extra inflated with a year’s worth of expenses because of that as well.

An emergency fund can really help if you have a bad month, if something goes wrong with your business plan, or if you have some major expenses coming up.

Instead of completely giving up on your dream, your emergency fund can help you power through any bad months so that you don’t have to quit (unless you truly want to, of course).

 

4. Spending a crazy amount of money.

Luckily, my business is very cheap to run. I don’t need much in order to make an income. All I really need is my laptop and internet. Everything else I pay for are really just little luxuries to make everything a little bit easier.

When I first started my hustles, I ran it much more cheaply than I run it now. I wanted to save as much money as I possibly could.

This is not how everyone runs their business though. I have seen some business owners start their business by spending TOO much money on items that they probably do not need. Yes, some items are a need, but others can probably wait a little bit until you know you have a viable business plan.

Also, some spend a lot of money on their business just so they can write the expenses off on their tax return. Let me say this, just because you get to write it off it does not make the item free! You still have to pay for the item.

 

What mistakes have you seen or made?

 


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Michelle Schroeder-Gardner

Author: Michelle Schroeder-Gardner

Hey! I’m Michelle Schroeder-Gardner and I am the founder of Making Sense of Cents. I’m passionate about all things personal finance, side hustles, making extra money, and online businesses. I have been featured in major publications such as Forbes, CNBC, Time, and Business Insider. Learn more here.

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  1. Sahil Arora

    No doubt Michelle all the mistakes mentioned by you are true. Though I am not self-employed fully yet as part time blogger I agree with your points.

    1. Michelle S.

      Thanks!

  2. Bre @ The Weight of Debt

    Awesome post! As I am working to start my own business I am walking with a lot of caution in regards to all of these things! I am slashing back spending left in right just in order to get started with no debt. When we opened the business bank account last week the banker started talking about once the business has some credit opening a business credit card and I was like whoa whoa whoa…nope that isn’t going to happen. I would much rather go without or take longer to start my business than go into debt to get it started.

    Starting a business is most definitely NOT easy. I’m tired and I’m only about month into getting ready and I haven’t even started production. Staying organized from the beginning will definitely be key in my long term sanity even though it takes more time now.

    1. Michelle S.

      Yes, staying organized from the very beginning is very important. That was a big mistake of mine!

  3. Marilyn Blau

    Many companies fail for not seeing the forest for the trees Keep looking at the big picture

    1. Michelle S.

      Thanks Marilyn!

  4. Heather

    My biggest mistake was thinking it would be easy! And I found that I’m not that great of a sales person. Go figure!

    1. Michelle S.

      Aww well sales is something you can always get better at 🙂 It takes time!

  5. Joe @ Budget Breakaway

    I think a big mistake for me would be not separating the work environment and life environment. When you’re passionate about your work it’s soooo hard to switch off and relax!

    1. Michelle S.

      Yes, it’s definitely very hard to switch off. That is something I’m still trying to do!

  6. SavvyFinancialLatina

    Those are great tips Michelle!

    1. Michelle S.

      Thanks! 🙂

  7. Shannyn Allan

    I made the mistake of trying to do everything myself…including the tax accounting and website coding, which I’ve now hired someone for. I nickled and dimed my own time and didn’t focus on the things that could have made more money or provided a good return on my time.. I would never be good at taxes, nor would I ever be able to code a website. My cost per hour was outlandishly stupid to do those tasks, I should have just hired it out- but of course, I thought I was “saving” money by doing it myself. Had I known how much it was really costing me, in frustration and tasks that could have provided a better return, I would have changed my ways!

    1. Michelle S.

      Yes! There are many times when I try to do something myself to save myself money, when in reality I am just wasting my time and money. UGH!

  8. Natalie

    I think not having a sizable E fund is the worst mistake that freelancers make. This line of work is very volatile and you never know when you will get a huge payday or be barren for weeks.

    1. Michelle S.

      Yes, I agree!

  9. M.Clark

    I am not self-employed, but I think these are very good tips, I’m sure a lot of people make these mistakes. Thank you for sharing this post.

    1. Michelle S.

      Thank you!

  10. Paula Ball

    I was self employed for 25+ years & didn’t pay in like I should. Now I’m battling a serious illness & living on $800 a month. Not easy to do. Pay your taxes & social security!!

    1. Michelle S.

      I’m so sorry Paula. I hope things get better.

  11. Michelle S.

    Yes, a simple spreadsheet can save so much time. I make sure to track everything in a spreadsheet and it’s wonderful.

  12. Melissa

    If I ever get to be self employed, I will definitely need to work on the organization thing. I’d like to tackle that before I leave regular employment (if I end up doing that).

    Also, friendly aside – your signature/about you (at the bottom of your posts) is half third person, half first person. Just thought I’d let you know 🙂

    1. Michelle S.

      Haha thank you for catching that! I wrote the signature on different days and didn’t notice 🙂

      1. Melissa

        You’re welcome! I figured, and I know I would like someone to point that out to me, so I thought you’d appreciate it as well. Love your posts, Michelle!

        1. Michelle S.

          I definitely appreciate it. I’m guilty of rushing through things and not noticing my mistakes.

  13. jefferson

    Good post, Michelle.

    I hope to get there some day as well.. Although I have my doubts that it will happen with SDR alone.. I need a new project to take off (and I do have faith that it will).

    The important thing to realize when stepping out on your own is that your business will only go as far as you are willing to take it.

    1. Michelle S.

      Good luck with your new project!

  14. Michelle S.

    That’s a great way to do it!

  15. Will, First Quarter Finance

    Thanks for writing these articles!!! Do you use an app like Paydirt to bill your clients? It’s keeping me far more organized than going it alone!

    1. Michelle S.

      No, I don’t use any apps. I simply use Excel and PayPal to track everything. Haha!