Skip to Content

What I Learned In My First Year Of Self-Employment

When I went full-time with my business in 2017, I had no idea it would become such a huge part of my life. Blogging started as a hobby that gave me a creative outlet to share my thoughts and teachings with the internet. I couldn’t have predicted that starting a blog would have allowed me to start a coaching business, would have helped me win awards, or would allow me to do three things I love: create, write and help people.

Taking the leap was terrifying but I’m so glad I did. Somehow, a year later, I’m still going and I’ve been able to make this self-employment thing work.

What I Learned In My First Year Of Self-Employment

So many people dream of being self-employed and sometimes I forget what a blessing it is to be in this situation. It’s hard work, I won’t lie. It makes you question everything you know about yourself, your abilities and your sanity. But it also gives you so much in return.

I want to share what I’ve learned over the past year in case you’re thinking about taking the leap too. There are so many things I could list here, but these are the top 12 lessons I’ve learned during my first year of self-employment.

1. Every week is a rollercoaster.

Some days you’ll feel so motivated because everything is going so smoothly. Other days, you’ll feel like everything is going wrong and you’ll want to give up altogether.

Know that this is completely normal and all entrepreneurs go through these ups and downs. If you feel like you’re stuck or question whether you should keep going or not, take a break and give yourself space.

2. You need to ask for help.

This was something I learnt the hard way, but it’s one of the most crucial lessons ever. You can’t do everything. You might have a lot of talents, but there will only be a few things you’re really good at. Take a risk. Hire an assistant to do the things you don’t enjoy or hire a coach to help you through your struggles. This way, you can spend more time doing the work you love.

3. Plan quarterly, not yearly

I had no idea how being self-employed would look. Though I had lots of ideas, I didn’t have a concrete plan. I tried to do everything all at once and plan for the whole year. It failed. I realized I couldn’t see or stick to something that far in advance.

What worked for me was planning things quarterly and then monthly. I focused on a handful of projects to complete during that time and my work became more manageable. You’d be surprised what you can get done in 90 days.

4. Self-discipline is vital.

The main reason a lot of people want to be self-employed is that they want the freedom to do things on your own terms. It sounds exciting though, doesn’t it? How good would it be to go and post some mail in the middle of the day on a Tuesday because you create your own schedule?

Yes, you can do that. And the freedom is wonderful. But you’ll start to realize that if you don’t practice self-discipline, you won’t get your work done. There is no one to tell you what to do anymore, which can be good and bad. It means you need to act like the boss and follow through with your plans.

5. Taxes aren’t that scary.

My biggest fear when I first went into self-employment was the fact I’d have to do my own taxes and deal with money. I had no idea if I was doing everything correctly which is why I hired an accountant to guide me through the whole process. They help me stay on top of everything money-related.

6. Some people won’t understand what you do.

I’m so grateful that my family and friends support my choice to be self-employed. I’m also thankful that they understand what I do.

Despite this support, there are still people who have asked me when I’m getting a “real job.” It’s a real kick in the teeth, but usually, it comes down a lack of understanding. You have the choice to help them understand what you do. Brush aside their comments and keep moving forward.

7. Self-employment is lonely.

I’m an introvert which makes self-employment the perfect path for me. But it can get super lonely when you spend 99% of your time by yourself.

Social media and email are great, but they don’t give you the same feeling as being in someone’s presence. One of the first things I did when I first started was create a mastermind group with two other girls and I now meet one of them once a month for a co-working day. Online friends are great, but in-person connections are the greatest of all.

8. There’s no shame in getting a part-time job.

Self-employment means your monthly income will vary quite often. Some months you might make $3k and others you might make $400. If you don’t want anxiety to appear every month, you could find a part-time job to give you a predictable paycheck.

Don’t feel guilty about this. It doesn’t mean your business isn’t sustainable. But in the long run, it’ll give you peace of mind and take some of the pressure off your own work.

9. Staying organized is key.

I’m lucky that I’m an organized person. But running a business requires another level of organization. There are so many things to keep track of and it’s important to have the right tools for the job. Here are some of the tools that help to keep me organized:

  • Asana for planning out projects and breaking down goals into manageable steps
  • Acuity scheduling for scheduling meetings and calls
  • Todoist for staying on top of daily to-dos
  • Google Calendar for staying on top of appointments

10. You need to be strategic.

One of the first things you’ll realize when you go self-employed is that there are so many things you can do now you have the time to pursue them. But this can leave you feeling overwhelmed and it might mean you unintentionally cram your day with a lot of tasks.

My biggest piece of advice here would be to write a list of all the ideas you have and rank them based on two factors:

  • What will make you money
  • What you’ll enjoy doing

If you can find an idea that combines those two components, go with that one first.

11. Self-care fuels your work.

There’s so much to do in your business that it can be easy to forget to stop working. You might even find yourself feeling guilty about not working because there’s always something else to be done.

It’s such an amazing feeling to love your job. But self-care is a vital component to your work. It might feel like your business might crumble if you prioritize it, but more often than note, the opposite will happen. You’ll be approaching your business from a calm state of being.

12. You are not your business.

There are other things in your life to enjoy too. This can be easy to forget when you’re working on your business all day every day. You have to detach yourself in order to make progress. Explore other hobbies. Meet up with friends. Take time away from social media. Give yourself time to completely switch off from your business.

I hope this has given you an insight into self-employment. It’s no easy task, but it’s definitely the best thing I’ve ever done.

About the Author

Holly Sutton

Holly graduated from Lancaster University with a BA (Hons) in Linguistics and from the University of Central Lancashire with an MA in Magazine Journalism. She enjoys keeping fit, running her blog, and spending time with her family. She hopes to grow her digital marketing business A Branch of Holly and continue to serve bloggers and small business owners!


Read previous post:
How I Built My Side Hustle Through Social Media

Is it possible to use social media to make extra money?