Great to see that you are making the big leap. You should go for it! I started freelancing 4 years ago. It's the best decision I've ever made. It grew really well over time and I started my own consultancy last year and we're now a team of 5 full-time consultants. I'm still working on getting to a level where I can start getting lazier and let the team handle things
It's good that you aren't rushing it. Not everyone has that option. You should take your time and plan it out. But at the same time, don't do it so much that you don't start at all!
Here are my thoughts on your questions:
How did you approach it?
I was working for a software research and development center for about a year and I actually didn't have any problems with it. I hadn't even thought about freelancing at the moment. But then, I had to leave the company(for good reasons) and I was suddenly unemployed. I did try finding a full-time job somewhere else, but they weren't ideal. So, I decided to try freelancing. I started out by reaching out to my network of friends, family, and former colleagues. I was able to land a few projects this way but they weren't UX work. I had been a front-end developer before I got into UX, so I had to utilize my front-end development skills. Basically, I was taking anything that was coming my way. This went on for almost 3 years, when I finally started getting a few projects where I could utilize my UX and CRO skills. That's when I decided to really specialize and focus on doing UX work. That went really well and now I run a UX/CRO consultancy of my own.
What would you have done differently?
If I had the choice and time to really plan it out and do it properly, I would've specialized on my core skills right from the start. Having a general approach (like "Front-end developer" for e.g) only leads to being commoditized. If you specialize in something, you'll be taken far more seriously and paid well at the same time.
What was the biggest thing you learned while going through that process?
It's all about how you position yourself. Of course, you have to be really good at what you do. But that doesn't automatically guarantee that you are paid well. After all, there are so many people out there doing it for such low rates. I don't blame the clients either. If you look at it from their perspective, here how it goes: Look for experts online > Contact them > Get sent emails full of things that you don't understand > Get quotes that are wildly different > Get frustrated.
That where you can really differentiate yourself. It's not about designs or code for the clients. They're looking for the ROI. If you position yourself well, you can command the highest rate but still land the work. Productizing your service is one way to do it. It also gives you more stability and the clients don't need to be worried about the hours.
How has it evolved over time since you started freelancing?
It has been a really great experience since I started really learning to specialise and position myself. Now we're up to 5 full-time people in the team. It's still not perfect. I'm still learning and finding ways to build a more stable pipeline of work and clients. I'm yet to accomplish that but I'm sure that it'll happen with some effort and proper planning.
How's your work/life balance?
To be honest, I'm bad at this I am working on making it better.