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Why freelancers fail and what to do about it

Over the years, I have been approached a number of times by people who want to become freelancers.

Mostly men, in my field, but one or two women have asked (as employees) how to become a freelancer. Each time, I give the same advice, and out of the 20+ people who have asked, only one has presumably done anything or followed my advice in the slightest.


No one is really ready to become someone who is basically unemployed, with no set paycheque coming in, worrying about if/when they’ll find work.


When I first started freelancing, it was because I was pushed into it. I was extremely unhappy at my job and the opportunity arose (along with my temper), and I quit on a very auspicious Friday afternoon.

The minute I quit, I had dread – what was I doing? I had only $2000 in the bank to last me until I found something. Would I ever find something?

Self-doubt crept into my head, and I was truly NOT MENTALLY PREPARED to go.


I leapt off the cliff. I was angry enough to take the risk to quit and try my hand at it, and worse come to worst, I would just find another job.

In hindsight, I took zero risk, my skills were in high demand at the time, and there was no better time to quit and freelance, but when you’re in the middle of a fog of self-doubt, rationality doesn’t come into play especially if you had NEVER considered you’d ever work for yourself again, while trying to clear $60,000 of student debt.

My advice?

If you really want to freelance, you need to mentally prepare to not have a job. No income, and to feel your empty days loom over you as you sit and fret. It is real, it is going to happen, you need to prep for it and stay busy some how.


I was definitely, 100% not financially prepared. I quit on a whim and things worked out for me, luckily enough.

I DO NOT recommend this to other newbies though. DO NOT quit without a financial plan.

You also have to take stock of the job market — Is it ripe? Are headhunters calling you all the time? Do you think you could find something, anything? Are companies hiring in general?

If yes, and you gut is telling you to give it a shot, GO FOR IT.

What is the worst that could happen? You find another job? (Well, make sure you CAN find another job first, and how likely that is before you quit).

Having savings, helps you see that you can give this a try for a while and see how it goes. If you don’t have that money, like me, your stress and anxiety levels are likely to skyrocket.

My advice?

I would suggest at a minimum, having 6 months of money saved.


If you want to freelance, you gotta ask freelancers how they did it. You’ll hear a billion stories:

I was let go.

I was transitioning to another career and it just came up.

I was angry and quit without a plan.

Whatever it is, there was a trigger, something strong enough to shove them off the cliff to use their wings for the first time with no safety net.

You don’t necessarily need a dramatic trigger to quit and freelance, but you do need to know what it is like in the first few months of freelancing.

My advice?

Pick freelancer brains – ask them what it was like, how to budget for the money, how you get paid, how OFTEN you get paid (I get paid monthly which means it was a huge switch from a bi-weekly cheque and I had to wait a MONTH before I got any cash).

Ask if there is stuff they wish they knew, that worked for them, that didn’t work for them.


Lots of wannabe freelancers do what is the easiest to accomplish on a list, when they think they MAY want to become a freelancer.

They do things like create their company logo, get business cards, buy printers, upgrade their cellphone and/or plans, or stock up on office supplies.


You know what matters?

Your resume. Your resume, and GETTING A JOB that will get you PAID, and networking online, changing your LinkedIn profile to show that your are available, and jamming it full of keywords for the jobs and contracts you want.

Start talking to other freelancers, ask them for their contact info, go to coffee with them, stay in the forefront of their minds so they’ll think – Oh right! She is a ______ looking for a contract as a _________.

My advice?

Do not buy, or spend a single red cent on anything that is not going to generate you money.

Find other ways to make it work.

If you don’t have a phone, obviously, you will need to buy a phone or a cellphone, but you can buy a CHEAP prepaid phone with minutes on it. All you need is a number. You don’t need a 10GB data plan with unlimited calls and texting, that can come later once you start bringing in money.

If you need a printer, ask yourself if you really do. Everything is done electronically these days.

Can you use a friend’s printer? A library printer? Pay for it per page at Staples?

Don’t waste your precious savings while you are in freelancing mode, nor your TIME on generating logos and letterheads. That will ALL COME LATER once you establish yourself.

Focus. On. Getting. The. Money.

Even accounting and bookkeeping — don’t bother with software or anything. List it all in Excel or buy a cheap tracking sheet like The Budgeting Tool, and use it to run your business (I actually do use it to run my business, I have a personal sheet and a business one).


I cannot tell you how many times someone has said: Oh there is a contract I could take, but I am going on vacation for 2 weeks…

Or stuff like it isn’t a good time right now because of _______________.. (I tune out at this point).

Know what I hear?


You can always ask them to wait 2 weeks until you’re back, as you already booked vacation. Most clients, will say “Yes”. GET THAT CONTRACT SIGNED. Get your name on there, negotiate a rate, and come back to a new life.

The other thing new freelancers make as a mistake is also not taking any contract just to get started. They want work with conditions.

They say stuff like: Oh it isn’t in the right neighbourhood where I live in. I ONLY want contracts near me.


IT IS A JOB. TAKE IT, make the money, save it, and once you have $200K in the bank saved as a cash cushion like I do, you can start calling the shots and refusing work.

You’re also no longer an employee. If you wanted a job close to you, and to never travel outside of your neighbourhood (let alone city), do not ever become a freelancer, you will not last a year.

I personally do not love contracts far up north or south, but if they are good, I will take them. I will suck it up and commute, and look for a closer contract to cut down on the driving time.

You will NEVER find the perfect contract or client, but you need to find something that fits 50% of what you need.

You can’t be picky, unless you’re rich and don’t need to work at all. You have to focus on getting PAID, even if it means the contract means getting stuck in traffic for 45 minutes a day.


This mistake kills me. At least half of the freelancers I meet are missing the basic essentials to be eligible for contracts.

Know what the 2 worst offences are?

Not knowing how to speak, read, and write in the given language(s).

Here in Quebec, it is French and English.

If you only know French, you’ll be hired, but unlikely to freelance as you will have to work in English often, with the rest of Canada or the United States.

If you only know English, it is a bit better than knowing only French, but people aren’t going to take you unless they’re up against a wall and stuck with no other choice. I know this, because I didn’t speak French for the longest time and couldn’t find work easily.

I know learning a language is hard, but it isn’t impossible. If you want to make bank, you need to push yourself out of your comfort zone and make it happen. Rent language DVDs at the library, play on Duolingo, find friends who speak the other language. DO WHAT IT TAKES.

Not being incorporated

Freelancers here, need to all be incorporated unless you are doing stuff like blogging, or design work, etc.

In my field, every company asks if you are incorporated. You’re not? You’re more of a liability/risk, and they’ll pass you over for someone who is.

What does it take to incorporate and do the taxes each year? Not as much time as you think, especially if you’ll make bank off it.

You need to register the company ( under $500 ), choose a name for it, register for sales taxes once your income hits $30,000, and that’s it.

It amazes me that people can spend a year calling themselves freelancers, burning through their savings, and not do BASIC #$*#% like this.

(Also, they never asked people who are in the industry, so of course no one told them they needed to incorporate)


I have had mostly the women, tell me that they would “need my help” to get them set up.

I side-eyed them, and smiled. I didn’t promise anything, and never will.

I am not here to be a FREE resource. You want my time to help you fill in the papers and all that #$@?  .. Then PAY ME.

I had to learn all of this the hard way, everything in French, how to register, how to file for taxes, how to incorporate, and you think I am going to give it to you for free?

The most I can do, as a colleague, is to tell you a short list of what to do.

I told one guy this who wanted to help his wife incorporate as a freelancer, and said he had to:

  • Register the business
  • Register for sales taxes
  • Get a contract from the company that made sense

You know what he did? All of that, alone by himself.

He just went through my checklist and figured it out, with the links I gave him.

He is the only one out of all of the people who have asked, who has successfully done something instead of just flapping their mouths.

I can give you the basic tools to start – links, short checklist of what to do – but then you’re on your own, unless you want to pay me for my services.

I am not here to read papers in French for you, to help you fill in information, to tell you how to set up your accounting, bookkeeping and organization, and how to find contracts, without there being something in it for me.

You need to PUT IN THE WORK to do it yourself so you know how it is done.

If you were a dear friend or family member, yes, this would all be free, I will spend time helping you no problem, but I would not be filling in papers for you – you would be doing the bulk of the work, and I’d be guiding you in detail.

If you aren’t, and we are just colleagues, I have zero interest in doing so (what’s my incentive?), and that’ll be the truth for anyone you ask.

So, still want to freelance?


  • GYM

    I admire people who can freelance and work for themselves, it takes guts to make the leap of faith but the rewards can be so much greater than working a salary job.

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