Transitioning to Freelancing


This conversation actually started on another thread and I thought it would be a good idea for it to have its own special place.

I’m at a point now where I’m starting to plan my transition to freelancing. I think the transition will be a slow one and I will continue to work full time until I am able to make the switch. Honestly, I’m in no rush – I want to take the time to ensure that I do this properly (and legally) I’m excited to have the opportunity to build something that is all mine and exactly the way I want it.

Why do I want this?
To be perfectly honest, while I’ve met some lovely people and worked on some fun projects the corporate world really isn’t for me for a number of reasons.

Why now?
Opportunities for freelance work have been coming in and it’s time I started building upon those for my future.

I would love to hear from people who have successfully made the jump and anyone else who feels like chiming in is welcome too!

How did you approach it?

What would you have done differently?

What was the biggest thing you learned while going through that process?

How has it evolved over time since you started freelancing?

How’s your work/life balance?

Thanks guys,



Good on you Ash, I fully support your move. As mentioned in the other thread, I made the transition from employee to freelancer last year and it’s been a very successful move for me.

There are a few caveats though:
1 - I’m not a UX practitioner, I’m a freelance enterprise community manager (different job, but the principles are still the same)
2 - The nature of my job means that I have several long term contracts (3 at the moment) rather than doing things on a short term job basis. That makes things much more secure and less stressful.
3 - I already had my business set up (I created my company back in 2006 with a view to doing something with it when I had kids)

[B]How did you approach it?[/B]
Accidentally. I was working a 20 hour week for one client so that I could work from home and be a full time mum to my twins. That job suddenly came under threat so I started looking elsewhere. As a result I got this one. The first job then changed their mind and begged me to come back. My kids had just started school so I decided to up my hours to 30 per week, which meant I could do both jobs at once. I then found a third client that was keen to have me, and I realised that the diversity of the roles would set me up with career flexibility in the future, so I figured out a way to juggle them. I have never looked back.

[B]What would you have done differently?[/B]
Honestly, nothing. It helped having the business already in place. When I was much younger I freelanced (that time as an architect) and it was difficult and scary. The worst bit was doing the accounts. This time around I employed an accountant to do the initial stuff, which I highly recommend. I now employ my boyfriend, who has taken over from the accountant. Means I can concentrate on the work without getting stressed about the admin.

[B]What was the biggest thing you learned while going through that process?[/B]
Not to over commit (I’m still learning that). I start very early and often finish quite late. I actually blogged about it for one of my clients here. You also have to be flexible with your time (which doesn’t come naturally to me) and have the ability to self manage. You need to be driven, self motivated and communicative. If financial security is important, I’d definitely recommend going through the first part of the transition while remaining in full time employment. Get a feel for the market, get your company sorted, get your promotional strategy figured out etc while you’re still bringing in a pay check. A lot of freelancers fail because they jump straight in, and then panic. It’s also important to make sure that you don’t get yourself into a position where there is a conflict of interest. In my experience, it pays to be fully transparent about who else you’re working for.

[B]How’s your work/life balance?[/B]
Fantastic. I balance a 30 hour week with the kids, the gym and a social life. If I want to meet a friend at the pub for lunch, I do. If one of the kids is home sick, that’s not a problem. It does mean that there are times when I work on a weekend, or into the night, but I’m ok with that. It’s a small price for full autonomy and being your own boss.


Thanks Hawk! :slight_smile:

I’ve done some research this week and determined that I definitely need help from an accountant! :slight_smile:

I’m similar to you in that my plan is to do more with my business when I have kids, I’m glad to hear it’s worked well for you. I like the idea of building it while I work full time - as it is I already spend up to 4 hours a day on professional development and learning stuff so it’s not too much of a stretch for me to work around a full time job.

The conflict of interest thing is so true! I’ve always been in the habit of declaring everything and being open and transparent.


I’m just about to make the leap myself, and I am nervously excited about what awaits! How are you doing Ashlea?


Hey Dean,
That’s awesome!
I’m getting there, slowly but surely. I prefer more of a slow, gradual transition than a big bang.
I’m about to launch a regular column with Optimal Workshop which I am very excited about and I’m currently looking for consulting jobs so I can learn more about that side of things.


[SIZE=14px]Nice approach! I was going to use my holiday time this year to take some freelance projects on, but the more I thought about it, the more I felt it was better just to take a(n educated) leap of faith. I am not moving forward at my current workplace, so if I made myself available for projects then I’d be able to give them my undivided attention.[/SIZE]


[QUOTE=Dean;5568] I am not moving forward at my current workplace[/QUOTE]

Same here- that’s probably my biggest motivation to crawl my way out! :slight_smile:


Hi Ash,

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 :slight_smile:

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:

[B]How did you approach it?[/B]

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.

[B]What would you have done differently?[/B]

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.

[B]What was the biggest thing you learned while going through that process?[/B]

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: [I]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. [/I]

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.

[B]How has it evolved over time since you started freelancing?[/B]

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.

[B]How’s your work/life balance?[/B]

To be honest, I’m bad at this :smiley: I am working on making it better.


I also recommend looking at Brennan Dunn’s site - . He has a lot of priceless advice.