Why Being My Own Boss Isn’t Always the Greatest (and Some Things I Do to Help with That)

Since I started my online business in 2008 I have never once wanted to go back and work for anyone else. But that doesn’t mean that being my own boss is always easy, or even enjoyable, at all times. Here are some reasons why it sucks being my own boss!

Telling People What I Do

It’s been over eight years and I still don’t know how to answer people when they ask me what I do! This is partly because I am a bit socially awkward, but also because most of the world don’t understand this whole “online business” thing (let alone the fact that my business has changed so much since I started). I don’t really have a solution to this, only to say that it’s really OK if you describe it in a way that might make more sense to them but doesn’t quite match what you do in reality.

Click here to sign up to my free library of biz-building worksheets, guides and tools

Making All the Decisions

One of the best things about being your own boss is making all the decisions in your business, but for me it’s also one of the worst things. I have to be honest and say I find it hard to make decisions – I’m sure this is a self-esteem thing, so it might not apply to everyone, but for me it comes down to not trusting in my abilities (and perhaps comparing myself to others, too – see below). The good news is, though, that the more I practice making decisions, the more I realise that running your own business is all about taking risks, and learning from your failures. Playing safe might be more comfortable, but it’s probably not going to make a big difference in the world!


I always enjoyed maths at school but I still find bookkeeping and taxes confusing. As my business has grown I’ve had to deal with more and more in this area, like VAT and registering as a limited company. For years and years I was too scared to talk to an accountant (don’t ask me why!) so I tried to do it all myself. As of 2017, though, I finally have an accountant taking care of it all and can say it really feels wonderful. Plus I try to look at the larger and larger tax payments as a good thing – after all I am contributing to society and helping to pay for public services that I use! (Click here to read my separate post all about how to stop freaking out about money in your business)

Spending Time on Tasks I Hate

There was a certain point in my business when I realised I was spending more time on admin than I was on doing the work I wanted to do. I was getting lots of emails, having to sort out my finances etc. As your business goes through a growth spurt, it often feels like the admin does too. There are a couple of things I did to help with this:

1) I hired people to do some of the work I didn’t enjoy doing, or that took me a long time because I wasn’t that good at it. Hiring people can be scary at first, but I started really small with specific tasks and grew from there.

2) I started implementing systems into my business. Things like noticing when I’d receive a question over and over again, and creating an FAQ page to address it (and canned responses in my help desk). Things like this might sound simple, but they can save a massive amount of time.

I actually wrote a whole blog post about saving time and creating more freedom in your business – click here to read it.


Working from home can take a serious toll on your health. You might not think you move much getting out to go to work, but I can tell you that spending entire days at home on your computer means that you move even less. For years I worked from home and did zero in the way of exercise, except for walking to the shops. This was not good for me physically or mentally, so a few years ago I started running and I’m so glad I did. In 2016 I also trained for the marathon, which worked really well since I could be flexible with my work schedule, and I try to get out for a run now 4 times a week. I still think I need to get out more, but this is a work in progress.

Time Off

Sometimes I find it really hard to take time off my own business, for a couple of reasons. Firstly, I find working really addictive. It’s not like a normal job for me, it’s really exciting seeing my email list grow, people interacting with my content, and money coming into my PayPal account. Even though I don’t love every single task I do in my business, I often find myself itching to get back to it after any time away.

It’s also just plain hard to plan it in sometimes. When you run your own business, you don’t get any paid holiday leave. In your mind, any time not spent working is time you are missing out on earning money. The good news is that building passive income and products mean that you’ll still earn money even when you’re not working. And, if you literally find it hard to find the time because you have too much to do, the good news is that the more you outsource, and the more organised you get, the easier and easier this becomes!

Click here to sign up to my free library of biz-building worksheets, guides and tools


Everyone procrastinates sometimes, whether they run their own business or not. The difference is that, being your own boss, procrastination just makes things worse for yourself in the long run – there’s nobody else to fall back on. There are so many times when I’ve ended up working on evenings or weekends just because I sat around all day not getting anything done. And it really sucks knowing that it was all my own doing!

As your own boss, you also don’t have anyone else above you making you get the work done (whether that means actually telling you off when you don’t do it, or just psychologically giving you a reason to get it done). You really have to learn to motivate yourself if you want to be happy working online.

The biggest thing I’ve found to help me with this is setting boundaries and getting organized. The more I outsourced, the more I had people relying on me to send them work. I slowly started planning further and further in advance, and setting boundaries on my work day, which forces me to get more done. I’m not perfect, but I’m getting better thanks to the systems I have in place to force me into working.


Depending on your personality, it can be really hard to set the boundaries you need to get work done. Friends and family often think that you are free to go out or talk to them during work hours simply because you’re working from home. I like to have a flexible schedule, but I also do need some kind of routine, so I’ve had to say no to people on occasion, emphasising that it is my work time.

You also have to set boundaries with clients, or contractors, which can be a massive learning experience! In the past, I’ve had to be quite firm with people who didn’t pay me on time (which is totally uncomfortable for my personality!), and I’ve also had to have words with team members that were constantly delivering late. The good news is I’ve learned that the clearer you are with your boundaries, and the more you set a good example, the more smoothly everything runs.

People Not Taking It Seriously

It can be hard for friends and family to take your business seriously when they don’t really understand what you do, and they see that you’re working from home. I’ve had people make multiple comments in the past about my husband being the breadwinner, which totally rubbed me up the wrong way. But the truth is you just need to let it go. It helps if you can clearly articulate what you do (see above!)

Cabin Fever

Despite being the biggest introvert, I also have to admit that being your own boss can get lonely and lead to cabin fever from time to time. It’s easy to end up spending hours on end sitting at your computer, sometimes without even getting dressed out of your pyjamas (guilty as charged!), thinking you have no time to as much as shower or get out of the house to run errands.

Sometimes I feel my mood shifting downwards when I don’t get out enough, so I’m trying to make more of an effort to take breaks. A quick walk is a great way to clear the mind, and can actually lead to way more productivity once I’m back. My running also really helps keep the cabin fever at bay, and it gives me some great time to listen to podcasts or think up new ideas for my business!

Click here to sign up to my free library of biz-building worksheets, guides and tools



Leave a Reply

Your email address will not be published. Required fields are marked *