How to Achieve Your Freelancing Dream – Without Quitting Your Job

How to Achieve Your Freelancing Dream - Without Quitting Your Job

Right now, you have one idea with the potential to change the world.

You know the one I’m talking about – it’s the one you’ve been putting off.  The one you don’t have time for. The one that’s too hard. The one they’re all going to laugh at you for trying.

While you’re sleep, this idea lingers at the foot of your bed like a creepy 5-year-old, watching you shift, prodding you to get up and research. You succumb to the pressure – but we both know you’re not going to do anything about it, are you?

That idea is the box that holds your potential, and opening it scares the shit out of you.

When I asked Linkedin, “What holds you back from your one great idea?” the first answer was…

“It’s not the right time to quit my full time-job.”

If someone said this to me a few years ago, I would’ve recommend they quit their full-time job and redirect their energy to pursuing their idea.

This is stupid advice.

What you should do is set a “Quit Date”, a goal number for a financial survival fund, and scale back on needless expenses immediately (like cable, takeout, sodas, etc…) so you can put that money in the bank.

Then establish systems to find extra work.

The fastest way to find extra work is to use Google’s advanced search operators to find job postings.

Step 1 – Use a keyword that job posters would use to describe your position, and add “” (without quotations) to this keyword search. Scroll down the left-hand side of the page to “Show Search Tools”. Click that, then click “Past 24 hours”.

The results you’ll get back show you where your keyword was used on Craigslist in the last 24 hours. (Most will be jobs.)

In the example below, I used the keyword ‘copywriter’ to show you how this works. You could use any keyword – graphic designer, website developer, spray-can artist… you name it. Look what happens:

Step 2 – Prepare a freelance portfolio with a simple and tweakable cover letter. Then take 10 to 15 minutes every day to sift through job postings and send emails offering your services.

Step 3 – Repeat daily until you’ve reached your target financial survival fund goal.

The idea is to build up your savings without abandoning your full-time job. This helps you decide if you enjoy the work and whether quitting your full-time job to become a freelancer is right for you.

And making this daily search for work a ritual teaches you good freelancer habits. (Bad habits are the leading case of freelancing death.)

People often fantasize about sticking it to The Man, but the reality is that not everyone is cut out to be their own boss. Self-management can be extremely difficult, and this method provides a low-risk way to earn extra income and test if self-employment is right for you.

“I don’t have time,” or self-sabotage explained

Please accept this as truth: If you’re not actively doing anything to bring your great idea to fruition, you’re self-sabotaging.

“But I don’t have [insert thing/time here]!” That’s one of the many ways we excuse ourselves from being great. People with far less have done much more with nothing but willpower and a strong mission.

“I have way too many things going on right now!” This is what I like to call productive self-sabotage. Let’s be honest – it’s easier to keep busy (and get paid) by investing your time in someone else’s idea than it is to work on your own.

If you really want to bring your idea to life, it’s important that you recognize and are honest with yourself about self-sabotage. Not building a financial cushion, not setting a “Quit Date”, staying disorganized and juggling too many projects… all these “reasons” are rooted in fear.

We don’t intentionally prevent ourselves from pursuing our ideas. I think the ego tries to protect itself from getting hurt, and so it stalls us from doing anything that might be even a little bit risky.

But game-changing ideas require a little risk and some action. They leave very little room for your ego.

How to destroy your ego – and your excuses.

It’s okay to be afraid of failure. But don’t let it crush your potential. Embrace it. Channel it.

Imagine what it would be like if you failed miserably.

Everywhere you went, they’d point and say things like, “There’s that guy who failed!” “Remember when he tried that thing and it just sucked?” “Oh my god, yeah. Why does he even bother getting out of bed?”

Just think of all the terrible things they’d say.

There’d be news reports and paparazzi following you around. All the websites and magazines and billboards would have “FAILURE” in industrial red letters slapped across your picture, circled just to highlight how miserable you are.

They’ll scrutinize your every move. They’ll criticize you for ordering the small because you can’t afford the large. They’ll call you names and dig up your past and drag your family into it.

They’ll ask your friends and neighbors for dirt. “Yeah, he’s been acting really depressed lately… not like himself at all.”

Take this in. Experience this ego-apocalypse for a good moment. Most people don’t, and they should. Training yourself to handle failure is like a prize fighter training to take a punch.

The gritty reality is that if you just go for it, you’re going to make rookie mistakes. Prepare and train yourself to take that hit, and you’ll be just fine.

Of course, you may not be cut out for it.

This may sound a little cynical, but you may not be cut out for self-employment after all. And realizing you’re not cut out for something is okay.

I wanted to be a parkour runner. Then I jumped (and fell) over a 4-foot railing, spraining my ankle and wrist in the process.

I wanted to be a parkour runner… but not enough to risk breaking my bones over. I wasn’t cut out for it. And now that I know, I’m perfectly content watching videos and pretending.

There’s difference between not doing something because you’re afraid and not doing something because you’re informed. Yeah, you may limp a little, but at least you’re not going to spend the rest of your life deluding yourself thinking this is something you really want to do.

You owe it to yourself to know. Yes, you’re going to get dings and bruises to get informed, but it beats sleepwalking the rest of your life.

And if you’re not cut out to take charge of your great idea, let it be your decision, not some state of living your fears and insecurities assigned you.

If you fail, let it be because you tried.

Don’t pass up your chance.

Post by Tommy Walker

Tommy Walker is on a mission to liberate the world of online marketing from the hucksters and charlatans. His show, "Inside The Mind" uses internet generation humor and professional editing to make complicated concepts easy to understand and fun to learn. Currently, he is guest posting on every major website known to man to kickstart Season 2 via this experiment in crowdsourcing.

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  1. Wow. This is a great post. It’s better to fail because you tried. For me this is very true, not-knowing if I’m capable of something is a terrible, haunting thing.

    One thing, though, in my experience craig’s list postings are the worst, too many writers scrambling for the same project makes it a race to the bottom as far as price. I think people looking for freelance work (especially in copywriting) should contact local and regional businesses in their niche…..lots of companies need freelance help.

    Another search I do is “write for us” in google and I’ve found some pretty good companies to work for that way as well.

    • Well good 🙂 I hope this helps you move past that fear just a little bit more. Check out the 106 excuses that prevent you from ever becoming great

      As far as craigslist goes, you’re right, there can sometimes be a race to the bottom on price, and the method is far from perfect. However you can use the same technique using other websites too,, mashable job board are the first two that jump out. Really it’s about creating a filter and a job funding dashboard.

      And switching up your keywords is a great addition!

  2. I love posts that show how to take specific steps to do something.

    Craigslist isn’t the end-all. It’s a the beginning. It’s not the only thing you should try but it can definitely be the first.

    Just dreaming about quitting your job isn’t enough. You have to grab the bull by its horns and DO something!

    Good stuff, Tommy!

    • Thanks Samar 😀 and you’re right! Craigslist is only the beginning. The most important thing is getting in the habit of using a system. Too many freelancers and wannabe freelancers just take this “it’ll come to me” approach.

      But remember, there’s a fine line between self-employed and unemployed. Systems like this help make sure you’re not totally on your own.

  3. Zinger, Tommy. I work hard, but I don’t always work smart. This is a great call to focused action. Thank you.

  4. I actually support Tommy’s recommendation of using Craigslist – because it’s not a recommendation on “how to make more money” or follow a “charge what you’re worth” mindset (which is bogus anyways), it’s a recommendation on “how to test whether you’re cut out to be self-employed and handle applying and landing gigs”.

    It’s a way for anyone to get in fast with barely nothing in place and test whether they can handle the self-discipline required to make it in the first place (and test other things like their ability to promote themselves, meet deadlines, manage client invoicing and negotiations, etc etc).

    Think of it like freelancing bootcamp. If you can hustle the quagmire of Craiglist and survive, then you can pretty much handle ANYTHING freelancing throws your way.

    But if you can’t even manage Craigslist job after 3 months of trying to make it work, then you may well be in trouble, and freelancing may not be the best option for you.

    • You nailed it James, I’ve seen it plenty of times where someone says “I want to be a freelancer” then just decides to quit their full time job.

      But when the next round of bills comes due and they haven’t actually made any money, they go crawling back to their employer or find another job that’s similar to the one they just had.

      It’s hard working for yourself. At least this way the trial run is there and even if the side projects don’t turn into a full time gig, you can still earn a decent side income!

  5. You stated the fact when you said that freelancing isn’t for everyone. That’s why your suggestion to start freelancing while still on a job is great (especially if you have dependents). If you can’t hit a target income through freelancing while holding down your regular job then it is a good indicator that you either are NOT cut out for it or need to develop your freelancing skills further.

  6. Renee Shatanoff says:

    I’ve been “freelancing” for over twenty years and I’ve never been without work. I worked in an environment where I was on the bottom of a seniority list because of the date I was hired, not for my ability. I was laid off more than once and decided to go the freelance route. I’m without a pension or retirement but I have an amazing amount of freedom that’s worth more than money. I like to say, “Time is the new wealth.” Meet your basic needs of shelter, food, and clothing. The rest is discretionary spending. You’d be amazed at the “things” you don’t need!

    • This is so true, and I think that Freelancing is something everyone should try at least for a year, just to see how they do.

      If anything at the very least, when you live solely off your own ability for a while, you’ll know that no matter what situation you’re in, you’ll always be able to take care of yourself and don’t have to live in fear that “The Man” is going to let you go at any point in time.

  7. Arjun Nair says:

    Thanks for such a great post !!!

    I resigned my job few days back without knowing about what i will do next,and then started assisting my juniors to do their final year projects(for cash in return!!).
    Now the momentum has slowed down.

    This was really a inspiring post. . .will surely pursue my dreams. . Thanks a lot again.


  1. […] Searching through job boards or help-wanted ads can turn up new clients quickly. Set a timer for 15 minutes each day and browse through ads, applying to ones that interest you. My personal favourites are FreelanceSwitch and Problogger. If you’re in a pinch, you can also try Craigslist. […]

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