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Becoming a freelancer (Part 1): The myths of being an independent freelancer

I get a lot of these emails from people asking me how they can become a freelancer after graduating college, or how they can freelance in an industry or a job they’re currently in.

This post will hopefully be the mother of all freelancing posts to dispel any myths and clear up any nagging questions you may have had about becoming a freelancer, but before I begin I suppose I should tell you how I became a freelancer.



I was working in a job that I loved, with a company (like every other company out there) that I hated. It wouldn’t have really changed much if I had switched from one company to another to find a better “work-life balance” because consultants do not have any “work-life balance” when they are billing 40 hours a week at a client, on top of traveling 10-15 hours a week, and trying to juggle a life at home.

Some consultants I knew, would start on the east coast on Monday, fly to another client by Tuesday night, work a day at another client in the middle of the country, and then “pop” by a third project that was happening on the west coast, then fly back home exhausted on the red-eye on Friday to a house where they had to run errands and deal with a stressed out spouse dealing with kids on his or her own all week, looking to dump that responsibility onto them while they got back some “Me” time.

That was the nature of my work and consulting is kind of an industry for the young and single or relatively unattached.

Still, I really liked my job. REALLY LIKED my actual job.

I just hated working for a company and being told that billing 40 hours a week was not enough, I needed to not only try and convince the client to let me bill more, but to also do internal company stuff like train others, and do internal projects on my off days (Fridays, usually).

Oh, and come in on weekends when a project was in a crunch.

I was so sick of it after 2 years that I quit and became a freelancer.

This is the part that people are most interested in:

How did I jump from quitting to becoming a freelancer?

You’re not going to like the answer, but it was mostly luck and good timing.


I am in a niche industry, and it was at that particular time that companies and clients were just DYING for my skillset, so without any real plan in mind, and only $2000 saved and about $15,000 left in student debt to repay, I quit my very high-paying but stressful job because I was on a project where they treated me like crap.

In hindsight, it was a pretty bold, reckless, some might even call stupid-ass move.

Who would quit with only $2000 in their bank account and $15,000 of loans to pay? WHO?

My bills alone in a month were $1500, and I would last maybe a month, two maximum without working.

It was NOT a good, sound, financial plan, but I am someone who is impulsive by nature and I can only take so much crap before I lash out and dish it back. I knew the day was coming when I would lose it (in front of the client no less), because of internal politics and power struggles, so I thought the best thing to do was to quit before I gained a reputation of sorts (I gained one anyway).

So I quit, and then I decided to freelance. If I couldn’t find a job, I reasoned, I would just join a company again and wait for my next opportunity to escape.

Luckily, as I mentioned, the industry was dying for my skillset at that particular time, so I found a contract easily, and as the fairytale goes, I cleared the rest of my $15,000 debt in a month (final tally: $60,000 of debt cleared in 18 months with the help of my budgeting tool) and banked $50,000 net after working for 3 months.

It was the best, most single encouraging moment of my life.

Then I found another contract, then another.. then another, and banked the money when I made it.

In my best year of working, I saved $130,000 net (after taxes and living expenses) from 9 months of work.

… but it is not something you can replicate, nor can I teach you how to replicate, so I am going to give you the reality of what it is like to go from working to becoming a freelancer.


This is near impossible.

I say “near” because I don’t like to rule out any possibilities of people becoming freelancers after they graduate, but frankly, no one is going to hire you without any experience.

Like it or not, you might be the smartest, brightest person in your class and can outclass anyone in your current field of work who has been there for 10+ years, but NO ONE WILL HIRE YOU.


You’re GREEN.

Would you hire an accountant fresh from their certification, bright-eyed and bushy-tailed to take care of your books at a Fortune 500 company?

No? Why not?

…. and there’s your answer.

You cannot start after graduation (unless you’re in a field perhaps like graphic design or website design where you can actually show your work), and no one will take you seriously.

This is the reality of  business, not just in freelancing but in ANY business.

Clients want to know that you’ve been proven on other clients (not them), and you won’t go ahead and screw things up, no matter how well-intentioned or bright you are.


NOTHING, I repeat, NOTHING replaces experience, but it’s that catch-22.

Here’s where you wail: But how are you going to get experience as a freelancer if no one will hire you because you don’t have any experience?


This is why you need to join a COMPANY.

A company already has senior people there and loads of “experience”. They will basically let you tag along on the backs of their senior folk, and from there you can start building a real resume.

They’re all about building up junior people into senior people, and then seniors either stay and become very senior, or they leave for another company to make more money, and/or freelance depending on if your industry lets you do so.

Also, if you join a good company from the start, their name can carry you through as a freelancer, to give you credibility.

“Oh you worked for ____ and _____? That’s great!”

There you have it: You’ve been proven to know what you’re doing because that company hired you and kept you.


Just because I make a lot of money doesn’t mean you will.


I am going to repeat this just to be sure because I do not want people suddenly quitting without cause:

Just because I make a lot of money doesn’t mean you will.

(I hate to be so blunt but I feel like I should just say what I mean so that no one takes my words to be anything but what I am trying to tell you.)

I make a lot of money because as I said, I am in a niche industry.

No, I am not going to tell you what that is, but it does pay good money and I do have skills that I acquired first at a company and then over time at clients as a freelancer that make my brain very valuable.

Many freelancers on the other hand, would be thrilled as heck to earn $30/hour, which is not a bad rate (it’s $60,000 a year), some go higher, and some go higher still, but the trick is to look at it from a holistic perspective, that is, how many hours are they billing at that rate?

If someone is working 3 hours a week at $100/hour, that’s $300 a week, or $1200 a month.

In contrast, someone working 40 hours a week at $50/hour, would make $2000 a week or $8000 a month.

See where I am going here?

The actual RATE that you receive matters, but what matters just as much is how much TIME YOU CAN WORK.

You can’t force contracts to happen and you can’t force clients to hire you for more than what they want to pay for.

If you’re in an industry that already has established freelancer rates, then you’re lucky. You know what you can charge, give or take $10 – $20 depending on the project, client and market.

If you are in an industry that has NO rates or you don’t really know anyone who can help give you such rates, you’re a bit screwed, but you can calculate it like this:


In a typical year, assume you will work about 50% of the time, which is about 1000 hours.

How much do you need to charge per hour (@1000 hours), to live?

Better yet, if you were to go to a company, what would your salary be?

Double that salary, and divide by 2000 hours to get your estimated hourly rate.

E.g. You can get a job at $50,000 a year.

Doubled, it is $100,000 a year.

Divide $100,000 by 2000 hours to get your rate = $50/hour

If you take projects by a flat rate, and you think you can get it done in 10 hours, add a 50% contingency of 15 hours, then multiply it by your rate to give the client a quote.

Take a maximum of 10% off your price, no more than that.

You will most definitely go over time, and what you DON’T want, is to under quote the client and have to charge them more later. It’s more painful as a client to have to pay additional money later on, than to just pay the real amount up front.

For any kind of scope creep, such as them asking you to just do this “one little extra thing”, tell them it’ll be X amount of hours in addition to your current work load.


This one makes me laugh.

(See above for the calculation.)

As a freelancer, I have worked less than 50% of my life.

Yes, life is really goddamn unfair because I also made a lot of money while having lots of free time to gallivant and travel all over the world, but that’s the reality for most freelancers.

Many freelancers can hope on average over a career of 10-20 years to work 50% of their career.

It may be one year where you don’t work at all and you’re dying for something.

Or one year where all you  do is turn down projects and cry yourself to sleep at night at the wasted opportunity because there is just SO much work but you can’t take the project because you’re already stretched to the limit.


I hate to point out the obvious but you can’t.

If your industry is not already set up and established for freelancing, you will be the lone wolf on your own trying to create an industry that doesn’t exist, and furthermore, trying to convince clients that such an industry DOES exist.

Take for instance social media marketing. If back in the day, around the 1990s you told people: I’m a social media marketer, I put you online with a web presence and help you get more customers from your marketed image online., do you think anyone would have hired you?



Facebook only really took off in recent years which then spurred the creation of OTHER social media networking websites like LinkedIn, Twitter, Pinterest, Instagram, etc.

Without something like Facebook as the catalyst, this job of being a “social media marketer” did not exist.

How are you going to create a job and freelance in it if it doesn’t exist?


So not only do you need the industry to freelance in, you also need the skills that people will pay for.

Can I put it any more bluntly?

YOU NEED THE SKILLS PEOPLE IN COMPANIES WILL PAY FOR.. which of course, come from experience working for a company, and being in an industry that promotes and even likes freelancers.

If you don’t have any skills to sell to become a freelancer, no one will pay for your services.

It is as simple as that. A company (or anyone for that matter) will not waste their hard-earned cash on someone who doesn’t have anything to sell.

So you can’t go from being a secretary or an administrative assistant at some small doctor’s office to becoming a freelancer in marketing the next day.

Conventionally, you need to go back to school to train in marketing, and then switch to a company that deals IN marketing, gain experience, and THEN decide to become a freelancer in marketing one day.

On top of all that, you can’t be vague about what you want to be.


Almost every freelancer I talk to has a story, and their story goes like this:

I was fired / let go / downsized from my company, and couldn’t find a job at another company because they weren’t hiring, so I took a contract in the meantime, and that’s how I became a freelancer.


I was so angry / peeved at my company that I left, had no chance but to take any contract that came my way even if it wasn’t what I liked to do, and that’s how I became a freelancer, so that I wouldn’t put “unemployed” on my resume.

Notice a pattern?

Luck. Unfortunate circumstance. Most freelancers I know did not CHOOSE to become freelancers, they got fired and were forced into that position which they ended up loving (or hating, some go back to working for companies).

This makes total sense:

Why would anyone bank your whole life and stake their family’s well-being on HOPING that contracts will come their way, consistently, and pay enough to sustain them?

On top of all that, it is not regular income, so you need to budget and not blow all your income for that year and end up losing your house and starving the next.


One year or two, then you’re good to go to make money right?


I quit after 2 years because as I said, I am in an niche industry and it just happened to be the right time for me to quit and jump.

When I tell other freelancers how I became one, my story shocks them. It is just unheard of, and I was at the right place at the right time.

I am NOT NORMAL. I did not have a NORMAL career start for ANY freelancer.

NO ONE believes that it is what I did. I am TOO YOUNG to be a freelancer in my industry out of sheer luck, which kind of bites me in the ass once in a while because clients don’t take me seriously at first and I have to work harder than others to prove myself.

Again, these are circumstances you CANNOT REPLICATE, heck I can’t even replicate it myself if you paid me a million dollars to do so.

I was just REALLY lucky to be able to quit after 2 years and find a contract immediately. Most people, do not become freelancers until they have had 10 – 20 years in the business.

10 – 20 years in the business.

In some other industries, maybe 5 years is enough (graphic design, websites, anything where you can literally show a portfolio of your finished product / work to get clients).

In most industries, the average is 10 years working for a company before you even have an inkling of credibility.


I don’t know how else to put this, but if you fail as a freelancer, you should give it up and get a job at a company.

If within 2 years you cannot find a contract, even though your industry is open to freelancing, this is not the time for you to think: I can succeed where others have failed!

No, you have all collectively failed, and you should all go back and get a job with a company.

Perhaps in 5-10 years you can try again, or when you think that you hear a whiff of a contract or a way for you to become a freelancer.

Or maybe it’ll never happen because the industry dried up for freelancing.

Either way, you cannot force it to happen. Freelancing is a lot more volatile and trickier than just finding a job at a company where they tell you what they want.

Freelancers are not really told what clients are looking for, so when their resume gets rejected over and over again, you better seek advice as to why (if you happen to be in a good industry but can’t seem to get a foothold), or give up.


All consultants (or people who work on projects) travel. Not all freelancers travel.

Consultants are by nature, stand-in business people, or employees. They pop into projects, do their job, and get out.

These projects are not necessarily always in their home city, which is why they travel.

Freelancers don’t always travel. You can work from home (digitally), or travel very lightly to a client site once a month or less.


Freelancing consultants, travel if they choose to take projects. There were projects I could have taken but turned down because of the 10-hour a week flight from coast to coast, but that’s my perogative as a freelancing consultant to do so.

If I worked in a company as a consultant, I’d have no choice but to go there and work at the whim of my company.

So those are the main myths of being a freelancer, in Part Two, I will introduce to you the REALITIES of being a freelancer.


  • Michi Wynn

    Great post!

    This may be premature, but I’d be curious how other professional freelancers/consultants are finding their health insurance premiums for 2014 since many do not qualify for a subsidy.

    • save. spend. splurge.

      I don’t have this to deal with because I live in Canada and have universal health insurance.

      That said, I found American freelancing health insurance to be sheer insanity. To put things into perspective, I’d be paying $2000 net out of my pocket each month for the same coverage I can get here in Canada for “free”, which is about $500/year in costs.

      If I wanted to buy private health insurance, it would be about $150 a month.

  • Tania

    This was interesting and I always did wonder how you came to take the path that you did. As an old lady who has worked for large corporations, cpa firms and small consulting firms, I fully agree that you need to have experience before you become a freelancer. I meant it’s a no brainer right? However,I’ve also managed HR in some of my jobs and it amazed me how many freshly graduated expected jobs in management without the experience to back it up. I actually interviewed someone for sales luxury retail who was currently a cashier at Banana Republic (cashier is typically lowest on the retail sale totem pole). Sales at a luxury boutique is also considered a step up from a National moderate chain like BR. He was sounding real good and I liked him until he told me he wouldn’t accept anything lower than store manager! This is just one of many similar incidents I have experience. I found it so interesting because it seemed to be a generational shift as well (I came from the generation that paid their dues, don’t feel entitled, blah blah). So I think it’s good you wrote this post. By the way, you’ve got some balls girl to quit like that but I’m not surprised you stood up for your principles.

  • tryinghard

    I am regular follower of your blog, and previously followed you Fab-Broke too! From reading all your posts, I know you are consultant in a niche industry. I keep wondering what this niche industry could be,I stopped myself from asking this question many times.

    The only reason I would like to know is – I am young, and cruising through a ‘just ok’ job right now. I would give anything to develop my skill set and become a part of well paying industry if possible. I know it sounds naive to just go learn something that pays well. But I think the financial freedom of well paying job is the stepping stone to pursuing other hobbies and passions.

    So my question is, will there ever be a point in future that you would share what industry you are working in with us readers here?

  • dojo

    Excellent ideas and story. I’m also a living example that freelancing does bring in good money, but it’s not easy to do it. The fact I can support my entire family working from home, doesn’t mean it’s easy or it will work for anyone else.

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