To Freelance or Not to Freelance?


You’ve heard about all the perks of working freelance: flexible schedules, no boss breathing down your neck, afternoon naps, working at hip coffee shops, work + travel, and of course, the $$$ that comes along with it.

But the freelance world is not as pretty as it all seems to be. Like any desk job (or any job for that matter), going freelance has its less-than-glamorous moments: days that turn into nights spent in front of the computer (I used to forget what day it was), demanding clients who pay you less than they should (not to mention delayed payments. Helloooo, can you hear me?), working on the weekends, lonely days of not getting to see or speak to anyone else in person, losing a client (this happens quite often), and no government contributions whatsoever.

It can get really ugly real fast, make sure you know what you’re getting into and that you don’t regret ditching the 9-5.

Here are things you need to know and do before considering making a jump into the world of freelancing:

1) Do your homework

Always, always do your homework before jumping into anything. What are your strengths and what field/area would you most likely succeed/excel in? Are you a writer? A graphic designer? A programmer, perhaps? Think about what you can contribute to the world when browsing online job boards. This will help you filter jobs and will make it easier for you to choose which projects to take on, plus it will help you be specific with what services you offer.

2) Check your financial status

Transitioning into having a stable income to something that’s a bit shaky at first can be very difficult, so make sure you’re prepared. Somebody’s gotta eat (and that somebody is you); don’t go and make the leap when you’re not ready financially.

It’s going to be really slow and quiet at first, and some clients will just disappear without a trace. Trust me, it hurts so much, logging in and waiting for nothing. Sometimes they do notify you that they won’t be continuing (either because you didn’t do your job or perhaps their business didn’t take off). It will hurt more if you don’t save the rainy days and have a safety net. You’re your own boss now; and bosses always have a backup plan.

Also, make sure your government contributions, health insurance, and the like are up-to-date. Become an individual paying member. Again, it pays to have backup.

3) Prepare yourself psychologically and emotionally

Going to an office every day where there are other people is something I realized I took for granted when I was working from home (see this infographic I created). I badly missed human interaction. I am a very chatty person, and I need to be able to talk to others so it was pretty hard for me when I didn’t have any other people to talk to. It gets lonely, so be ready for that. List activities that you can do in between work to keep you sane.

4) Commit to a schedule

Contrary to what many believe, working from home requires you to set a set schedule for yourself. Calendars and to-do lists come in handy when you work for yourself. Going freelance doesn’t mean you don’t have to put on the effort of doing work. Come to think of it, it’s a lot more work on your hands now. Be on time for meetings, even when they are only on Skype. Those are as real as meetings could get.

It’s pretty easy to get lost in distractions when working from home – you need superduperovermegatothemax focus to get your shizz done. I’ve written about some tips on how to be productive even while working from home here, my favorite productivity apps here, and how to keep your focus here.

You’re an independent contractor now, so you’re in charge of your time and what you do with it. With great power comes great responsibility, ya know.

5) Learn the art of pricing

Yup. You can’t just show up on the interwebz and not know what your skills are worth.

How do you know when the price is right? Test the waters. Check competition. Of course, when you start off, don’t go asking for an unreasonably high price. Come to think of it, when you have no experience at all, start with free work. However, be mindful of the free jobs you take on. When you’re running a business, learn how to say no to things that are not in alignment with what you’re trying to achieve. Get those distracting, time-consuming “favors” out of the way.

Make sure you get great feedback to back up your pricing when the time comes. Once you get your skills honed and when you have a specialty, start increasing your rates. Soon enough, you’ll be at a place where you won’t need to look for jobs – the jobs/clients will come looking for you!

Learn more about how to price your services (hourly versus fixed rate) here.

6) Be professional at all times

As mentioned, payments get delayed sometimes. What you should keep in mind is that clients are busy (that’s why they hired you!) so make sure you always send an invoice. If they fail to pay on time, even after you’ve reminded them that their payment is due, then request to be paid again in a professional manner. Remind them subtly that you’re running a business, not doing charity work.

Also, be professional in handling clients. Do not promise to do things and end up not doing them. It hurts your client’s business, and it will greatly hurt your reputation. Have integrity and be honest – it’s for your own good.

7) Educate yourself continuously

Be a voracious reader. Read anything and everything relevant to your line of work. Always stay updated. In this overly dynamic world of the Internet, it’s easy to get lost. Every day is a new day and a new opportunity to improve your skills and widen your knowledge. Do not get left behind. Study hard, work hard. Read, read, read. If you need more reasons why you should make reading a habit, check out this blog post I wrote a couple of months back.

Join workshops and trainings and seminars. They’re good for you. Invest in knowledge-building and networking and skills enhancement. Your future self will thank you greatly.

8) Set specific, clear boundaries

When you make the decision to go freelance, you are also (unknowingly) selling your soul exposing yourself and subjecting yourself to constant emails and inquiries and what-not. Learn how to manage your time effectively.

Set clear expectations for your clients and for yourself:

  • What days are you working?
  • What times are you available?
  • Should they contact you via email, Skype, text, telepathy?
  • Will you be available to work during the weekends?

Be consistent with the answers you present your clients. This allows for transparency: your clients will know what to expect of you and when; and you, too, will be able to schedule other life activities such as ~actually living~ and spend time with the ones that are important to you – your family, friends, lovers, pets, DOTA, your Star Wars action figures.

9) Tame your emotions

They say, do not bring your problems from home to the office. But what if your home is your office? What do you do when you and your spouse/significant other/parent/sibling/imaginary friend don’t get along? And you know what, these emotional struggles often happen on a big day (your first day with a new client, a new project launch, a busy day, etc.) The solution is pretty straightforward: put aside your emotions. Your problems can wait. Your emotional turmoil can wait. Set those aside and focus.

Also.. put some Taylor Swift on to lift that dark cloud hovering over you. Works every single time. Trust me.

10)  Take care of yourself

Above all else, please do take care of yourself. Health truly is wealth, I could not emphasize this more.


So… are you planning on ditching the nine-to-five and going solo? Freelancing is such a fulfilling career, regardless of how people see it. I’ve been asked before, “Why don’t you get a real job?” And I always respond with just a smile. Not everyone understands this world, but it works for me. It won’t work for everyone, that’s for sure; but just give it a try. Who knows how many doors you can unlock by simply taking action on what you’re passionate about!

If you’re keen on becoming a virtual assistant and working from home, I have a FREE cheat sheet for you. Click here to download.

Till next! :)

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