6 Tips For Becoming Self-Employed—With Financial, Emotional, And Personal Success

February 15, 2023

In 2015, I left my full-time permanent position to go traveling. I decided this was a great time to give freelancing a go. Over the last six or so years, alongside traveling and living in various different countries, I have been within the world of self-employment and freelancing, mostly as a side hustle. Now, I’m actually self-employed full-time. Here are all the things I’ve learned along the way that have been pivotal to get me to where I am today.

Tips to becoming successfully self-employed

1. Believe in yourself

As cheesy as this sounds, it’s true and it’s so important. A few years ago, I never thought I’d be able to be full-time self-employed for a whole host of reasons such as trying to source clients, having to maintain a steady cash flow, dealing with the stress of taxes and bookkeeping, and the list goes on. This all changed last year when I moved to Canada right before the pandemic. I used the opportunity of everything going online to push myself and my skills in order to secure some contracts. I went into this with little confidence but as soon as I started to believe in myself and tell myself I’m cable, I started to have more success. Confidence really is key.

Self-employed on laptop

2. Be organized

There’s nothing worse than getting to the end of the tax year and realizing you’re missing receipts or you’ve misplaced invoices. When it comes to being self-employed, it’s a great idea to go into it with a plan to remain organized. If you’re more of a paper-based person, get boxes or shelves to store paperwork separately and in date order. If you’re more of an online/paperless person, download a spreadsheet template and research what you’re going to need in preparation for your tax return. I’m often telling myself off for not having saved an important file or for forgetting to update a spreadsheet. Now I set reminders so I can ensure I’m staying as organized as possible.

3.  Don’t be afraid to ask for help

Being self-employed often means you’re not just working as a graphic designer or a consultant or whatever it is you do, it also means you’re taking on roles such as administration, bookkeeping, and sales. I find many of these tasks quite difficult as they are out of my comfort zone. When I first started out (or when I moved to a new country), I often felt overwhelmed and confused about what I needed to apply for and do such as get business licenses or set aside X amount of tax. I’ve now created a little social network around me who have experience in the field and I can go and ask for help whenever I need it. Hopefully one day, I can help others and return the favor.

Help button on keyboard

4. Stay true to yourself

In the first few years of being a self-employed freelancer, I took anything and everything offered to me so I could earn money. I started to not enjoy what I was doing and lost passion. I also felt like I was stuck in the same place and wasn’t progressing in my career. I knew I loved working with nonprofits and working within comms, but I kept accepting jobs for marketing, retail, and e-commerce. Once I started to streamline my goals and started turning down jobs I didn’t actually want to do, I was able to create space and time to look for and apply myself to work I felt truly passionate about. This was so much more fulfilling and enjoyable, and now I love what I do and where I’m at.

5. Trust your gut

I have been given a lot of advice over the years and I have also ignored my gut instincts many times over. If I could go back in time and tell myself some advice, it would be to listen to myself more (and sometimes others less) and trust myself more. At the end of the day, you know yourself and your goals better than anyone. People will hand out advice even when it’s not solicited and sometimes it can take you off the path and away from your goals. Other times it can be that you’ve not trusted your instincts and ended up in a negative situation. As much as I have felt like I have no idea what I am doing sometimes, listening to gut instincts over what others think I should do that has led me to the most happiness (and then the success soon follows).

Self-employed on laptop working

6. Stick it out

Back in 2015, I definitely had it in my mind that things would just happen if I put in the effort and had the right intentions, and that’s not certainly not been the case. Sure, hard work and good intentions have been a huge factor in getting me to where I am today but the biggest one has been just sticking it out. From moving countries to global pandemics to wanting to give up and just get a job, I’ve clung on to the hope of being able to one day work for myself, work from home and have a great work-life balance. Six years later and here I am.

I’m now in a place in my life where I’m pretty content. I earn enough money to get me by, I love the work I do, I love who I work with and I work pretty basic hours, giving me plenty of time to be with friends, family, and outdoors. This doesn’t mean it’s all sunshine and rainbows. There are always things to stress over like losing work, having too much work, or not getting paid on time. Working for yourself full-time is hard work, but it’ll be worth it if you ask for help when needed, stay true to yourself and stick it out, through good times and bad.

Also by Anna: Master Of None—How I’ve Accepted My Multi-Talented Creative Life

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Photos: Canva

Anna Ashbarry
Anna is a Communications and Outreach Manager at Dyslexia Canada and works in a freelance capacity as an activist, photographer and writer. Anna uses various media forms to raise awareness of issues whilst seeking social justice. With a passion for human rights and international development, Anna has worked as a Youth Reporter in Nepal and continues to explore her interest in communications in order to help provide platforms for voices to be heard. Follow Anna on Instagram @annaashbarry


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