8 Questions to Ask Yourself Before Going Freelance 

by Sep 3, 2019

Is going freelance the right move for you?

If you are thinking of going freelance, make sure that you ask yourself these 8 questions first. It might sound idyllic but the reality doesn’t suit everyone.

We’ve all seen the ads pop up on facebook. A never-ending stream of freelancers telling us how their work day involves sipping from a coconut at a beach bar in Thailand, earning a six-figure salary while working only a few hours a day, or making a passive income from affiliate links while they sleep. 

And if they can do it, then can’t we all? Why are the rest of us still slaving away at our nine to fives when there is this whole world of job independence out there?

going freelance


Freelancing isn’t for everyone

Well, the reality is, although freelancing can bring a host of positives including location independence, flexible hours, and choosing your own clients, it really isn’t for everyone. It is hard work. And comes with a lot of downsides too. 

Take it from me. With several years under my belt in the freelance world, and having worked from the odd Thai beach myself, I can confirm that these amazing highs come with some equal lows. 

So if you have always dreamed of freelancing, or wondered about taking your side hustle full time, make sure you are prepared before you take the leap. 


8 questions you should ask yourself before becoming a freelancer


1. Do I know how to get set-up as a freelancer?

First things first, anyone going freelance must make themselves aware of the legalities of working freelance. Freelancers are self-employed, and must register as so. In the UK for example that means registering as a business with HMRC, while the US government can require different licences and permits depending on each state. This will differ in every country, so do your research. 

Along with this you will need to file your own taxes each year. Before becoming a freelancer, make sure you do your research on the tax system. You need to be willing to put time and effort into keeping track of all your earnings, as well as filing a tax return each year. In the UK you don’t pay tax on the first £12,500 you earn for example, while in Spain, you are taxed from the first euro. Make sure to forecast taxes into your earnings, as they won’t be deducted from your pay cheque like in standard employment. You don’t want to end up being hit with a huge tax bill you aren’t prepared for.


2. Do I know my specialty?

Secondly, do you know what kind of freelance work you will actually do? What is your niche? Do you have a selling point that will make you stand out to clients?

If you haven’t gone freelance yet and want some inspiration for areas of freelancing that could suit your skillset, take a look at this list of common freelancing sectors:

  • Content creation
  • Videography
  • Copywriting
  • Web development
  • Graphic design
  • Virtual Assistants
  • Digital Marketing 
  • Online Teaching 
  • Translation 
  • Saas
  • Editing / proofreading

It is good to be clear on what your specialty is before you start. Once you start building a portfolio and becoming an expert in a particular niche, it will be easier to leverage your career. Consider making a website that you can refer clients to.


3. Am I really ok with so much ‘me time’?

Freelancing gives you a lot of independence. But independence can sometimes also mean loneliness. 

If you work from home, or are location independent, you have to accept that you will be alone a lot of the time. Most interactions with others will be via email or Skype. 

This can be harder than you might imagine, and you need to ask yourself if you can thrive in a solo environment. Do you get your energy from being around people? Will you miss daily chats by the coffee machine and interacting with work colleagues? 

Work can provide a social network. If you are considering going freelance then ask yourself, do you have strong social networks outside of work? Or can you combat loneliness by joining a close knit online community such as Female Digital Nomads or Digital Nomads Hub?


4. Am I motivated enough?

Your alarm goes off at 7am. It’s cold and dark and you can’t remember ever feeling as tired as you do now. And wait… there’s literally nobody to answer to if you snooze for another hour. 

Are you motivated enough to get up and start work each day without the rigidity of office hours? Or are you easily distracted and could end up procrastinating throughout the day and then working till midnight?

There are ways to create routine, such as setting yourself working hours and personal deadlines. Joining a co-working space can also bring you structure, although you have to factor in the extra cost.

But ultimately when you have a deadline for a client, it’s on you to complete the work. And as a freelancer, you can’t always just turn off your computer at 5pm and try again tomorrow.


Self-awareness is a crucial skill for career success. Try our Returner Roll-Up Session to Learn How to Identify your Transferable Skills.


5. Can I say no to clients?

Some clients view freelancers as people that should be available at their beck-and-call, and they don’t always offer a fair wage in return.

When you rely on getting gigs to pay the rent, it can feel impossible to say no to a job offer or a client request. You don’t want to miss out on an opportunity.

However, to make it long-term as a freelancer and not burn out, you need to learn to set yourself limits and boundaries. These can be factors such as your minimum rates, when you can work, how long things realistically take, and how much work you are willing to take on.

I spent a long time as a freelancer bending over to client requests, because I felt like I couldn’t say no. However, when I started to fit clients into my schedule instead of the other way around, and learnt how to say no to jobs that weren’t worth my time, I started feeling a lot more in control of my career, and became a lot happier.

I also found clients can be a lot more understanding than you think, and the ones that aren’t might not be worth holding on to.


6. Am I ready to give up my job security and paid holidays?

Becoming a freelancer also often means giving up job security like sick leave and paid holiday. When you invoice by the hour or per project, if you don’t work, you don’t get paid.

It is also hard to rely on the consistency of freelance work, which tends to be project based. I have had jobs that have provided a steady income stream for several months and then have suddenly just dried up. And often freelancers don’t get any notice period, let alone a severance package.

To be a freelancer you have to be ok with a little risk. Is it worth it to be able to work doing what you love? Or do you need job security for peace of mind?


7. Do I know where to find work?

Finding work is a big one. Landing new clients is often a constant of working freelance, as you can’t always rely on one income stream consistently. You may need to have 3 or 4 clients at a time, and replenish them regularly.

Once you are more established you might start getting referrals, recommendations or even have clients coming to you. But at the start, you will most likely be reaching out to clients, applying on job boards, and pitching ideas.

If you have any benefits that could work to your advantage, use them.

Do you have a network of people that can help you find work?

Can you go freelance with your current employer?

If not, there are plenty of job boards out there for remote working that I have personally used to land clients:

AngelList – Start-ups, Web Development, Consulting

Remote.co – Writing, Editing, VA

ProBlogger – Copywriting

LinkedIn – Anything


8. Do I know how to sell myself?

Following on from the last point, now you know where to look, do you know how to actually land a job?

Are you willing to put time and effort into securing new clients? Or would the perpetual ‘interview phase’ put you in a state of constant anxiety?

Making yourself stand out can be hard in a saturated market. But writing stand-out applications is a skill you can hone. You need to master the art of solving the client’s problem in your application. Check out the client website and try and invisage what they are looking for from you.

If the company is  looking for a marketing copywriter, open your application with some copy for an instagram post around one of their products. If they are looking for an editor, pick out a typo on their website. Perhaps if you are a web developer, you could suggest how you could improve the functionality of their website.

If you have a specific niche, find a list of clients you think you could help with your services, create a kick-ass email, and send out cold emails en masse.


So there you have it. Eight questions to ask yourself before going freelance. Time to go do some soul searching and decide if you are ready to quit your day job!


Are you considering a career change? Our coaches have a wealth of experience and can help you at every stage of your career. Find out more HERE.

Hanna Greeman Contributor
Hanna is a languages and logistics specialist. She is currently living in Barcelona working as a Creative Copywriter.
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