How to prepare to leave your day job for your dream job in 5 steps

I did it! I quit my job as a senior designer at a top global digital agency to chase my dream to become a freelance illustrator. Here are the 5 steps I took before leaving my job to make sure I had the best chance at success.


This article is based on the podcast interview with Women Of Illustration where Dina Rodriguez and I went over all the best ways to prepare to leave your day job to go freelance. You can listen to the full podcast on Spotify or Apple Podcasts.


1. Develop a passion or a hobby into a side hustle


If you don't like what you are currently doing at your job, find a passion or hobby that you can develop further. Before you jump the gun and try to make money, make sure you refine your skills.


When I started working, I realised I didn't have the time to paint 6ft tall paintings like I did in college. So I picked up an iPad and started drawing just to make sure I had a creative outlet. I didn't put pressure on myself to become an expert; I just recorded my process (for myself) on Instagram.


I was really drawn to illustration and the impact it had on my mental health. What started off as a creative outlet turned into a healthy habit. I did two 100-day projects, offered to do free work for friends and constantly refined my illustrations. I researched the industry and was mind-blown that people were getting paid to draw! But before I could make any money, my priority was to develop my craft to a professional level.


2. Evaluate what you like and don't like about your current job


It's important to be clear about why you want to leave your job. Leaving the comfort of your day job to freelance is extremely risky; especially if you need to financially support others.


I was unhappy at my job but didn't plan on leaving because it paid "well" and it looked great on my resume. But once I started getting serious requests for commissions, I knew I had an opportunity.


So I made a list of things I love and things I can't stand about my current job. This kind of list can help you identify your dream job. Here's how mine looked:


Things I love: being creative, having different clients, social media marketing

Things I can't stand: lack of mental health resources, design being undervalued, designing for purposes that I didn't care about, ridiculous work hours


I then evaluated why I'm drawn to illustration and freelancing. I liked the fact that I could do what I love about issues that matter to me and positively impact people around me. I can pick and choose who I work with and which projects I wanted to work on.


So I started to critique my artworks against other successful illustrators in the industry to understand what level my art needed to be at to make money.


3. Focus on marketing and growth


To be able to reach a wider audience, you need to figure out:

  • what topics are you interested in

  • what message you want to convey through your art (make sure it's unique)

  • who your target audience is

  • what your target audience is interested in

Once you answer these questions, you can make sure your art contributes to the conversation in a new way.


I'll be getting into this step a lot more in upcoming blog posts but they key is to constantly analyse your data. Ask your followers why they're following you and what they want to see more of. Research which artworks have more engagement and why. Keep tweaking.


4. Figure out your finances


Personally, I wanted to experiment with going freelance without having the financial burden of having to make a certain amount of money every month. This way I can really focus on creating art that I want and take care of my mental health.


So I looked at my finances and calculated my monthly expenditure. I then decided that I was comfortable investing half of my total savings into this freelance experiment (I say experiment because I plan to apply for another job if this doesn't work out). With my monthly expenditure calculated, I figured I could last twelve months on my savings, even if I made no money.


Just be mindful that everyone's responsibilities and financial burdens are different. My method might not be suitable for you.


5. Make lifestyle adjustments to prepare mentally.


This is the last and most important step. Quitting your job to freelance can be terrifying if you don't mentally prepare for all the changes.


You won't have a regular income. You will have to be your own boss and set strict routines and deadlines. You will have to be disciplined. You also have to make sure you set time apart for self care and also to spend time with the people that matter.


I started by letting my family and close friends know that I will be needing their emotional support. I also asked for financial support in case of medical emergencies (since I won't have the comfort of a corporate medical insurance). I let my friends know I can't be going out for fancy dinners and hanging out all the time because my priorities have changed and I need them to support me.


I created a make-shift studio in my parent's extra guest bedroom. The tip here is to use what you've got and make it work instead of investing a ridiculous amount of money at the start. The biggest investment I made was in an upgraded, powerful MacBook Pro because my entire business will now rely on it.



Then I made sure I completed all my business registration and banking paperwork.




If you complete the 5 steps above, you're probably ready to give in your resignation! Make sure you ask if you can continue on a part-time / freelance basis so you can still have an income source. Either way, be kind to everyone at your company! Contacts are important especially for freelancers.


Hope that helps!


I can't wait to share my freelance journey with you. Feel free to reach out to me if you have any questions.


93 views
Sign up to get weekly newsletters with  exclusive freebies, news about new artwork and blog posts and more!