Thinking of Freelancing? Don’t Quit Your Day Job.


One of the best things I ever did for my freelance career was keeping my day job. Confused? Let me explain…


Photo credit: michaelthorner via Compfight cc

No, I’m not working part time at an agency or coffee shop, I do this full-time now.

And no, I’m not suggesting you shouldn’t freelance (ever).

But I AM suggesting you don’t just yank the ripcord and plunge blindly into the big, wide world of working for yourself – because chances are, you don’t know how shallow the water is just yet.

One of the most common questions I get from aspiring freelancers is:

“How did you know when to quit your job?”

It’s a great question – and arguably one of the smartest ones you can ask.

See, there’s plenty of advice out there on what to do once you’re ALREADY freelancing – but very little advice on how to make the jump successfully.

And that’s a damn shame.

Because what you do before you start freelancing will shape your career for the years to come – and while you’ve got a day job, you’ve got some stability you can use to start your freelance career out on the best foot possible.

4 CRUCIAL things you should do before you quit your job:

1. Save up at least 3 months of “survival” money. 

Before you decide to make yourself the captain of your own income, you should build yourself a safety net.

Do you know how much your rent, groceries, insurance and lifestyle are costing you? If you didn’t get a single client, how long could you survive with the savings you currently have?

If the answer is less than 3 months, you should be very cautious about venturing out on your own.

Here’s a familiar story…

  • Many freelancers start off optimistic, with a few solid contacts, but then…
  • When those contacts don’t pan out or the work dries up, they’re left without a reliable income source and so…
  • Out of desperation, they start taking on low-paying jobs to make ends meet, working harder for less pay, and…
  • These unimpressive jobs don’t help their portfolio at all. The work you display is the work you attract, so…
  • They get caught in a perpetual cycle of just trying to make ends meet with crappy jobs that keep on coming.

If you give yourself a 3-month cushion, you now have some flexibility to be more aggressive with your pricing and more deliberate about who you work with.

You gain the power to say “No!” to a project and negotiate a rate you’re worth – the most powerful position a freelancer can be in.

Photo Credit: welldunn via Compfight cc

2. Network on your boss’ dime. 

While you’ve got a full-time or part-time job, you’ve got some sustainable income coming in – which gives you the freedom to invest some of your hours in connecting with people and shaking hands instead of hunching over a keyboard trying to get jobs done.

Most of my work has come through the following channels:

  • Word of mouth referrals
  • Twitter
  • Content I’ve published on my own blogs
  • Content I’ve published to other industry hubs & LinkedIn

But every single one of those channels is a connection I’ve had to fuel, foster and follow-up on.

If you’re not busy sweating bullets about paying rent, you can spend more time fleshing out your portfolio and making connections, without feeling like you’re wasting your time.

3. Invest in your own branding.

Let’s be honest: Food, shelter and living costs are ALWAYS going to come before things like building out a website or getting a logo done.

But here’s the catch 22: If you don’t have time or money to market your business, then paying clients are going to be harder to come by.

One of the best things I did for myself early on was invest in getting some slick branding and a professional-looking site done up for Business Casual Copywriting.

Seems superficial, right?

But it’s not. If you can LOOK the part of a 10-year veteran, and if you can deliver like one, then NOBODY needs to know you just started out.

That means you can charge more, straight out of the gate.

But if you’ve got a terrible site on a domain name you don’t own and a hotmail address? Well, let’s just say – businesses can and DO judge on appearances.

You’ll do well to save up some cash and do your own branding right.

4. Find your first clients.

Controversial? Maybe.

When I did this, I made sure my boss was okay with me doing some work on the side and that it didn’t violate my non-compete.

If feasible, you should be floating out the idea that you’re ready to pick up some side work. If you can nab a couple steady clients before you make the leap (especially if they’re willing to grow with your availability), you’ll be much better set up.

But please – be careful with this one. If there’s a chance that picking up freelance clients would leave a sour taste in your employers’ mouth, don’t risk it – especially if you’re already employed in the field you plan to freelance in.


Please – don’t quit your day job (yet).

Use the stability that comes with having some predictable income to set yourself up for long-term success.

It could mean the difference between getting bigger, better projects at a faster rate – or slogging it out in the Upwork salt mines for months to come.

11 thoughts on “Thinking of Freelancing? Don’t Quit Your Day Job.

  1. Awesome post!

    Fortunately, I did a lot of what you mentioned here before going it alone.

    The things that are giving me a good start:

    1) Money saved up so I don’t start off in desperation mode.
    2) Clients in place and paying before I quit.
    3) Built a few key relationships that have a side benefit of also being a source of referrals.
    4) Landed my former place of employment as a client.

    Now, working on…

    1) Branding. Starting to talk to people and am totally willing to put some resources into this. No $20/hour nonsense for this guy.
    2) The boring stuff like accounting/legal. Needs to get done!

    Lookin’ forward to your new site going live! You’ve been a great help – I’m sure you’ve got more in you to give.

  2. Hello Dude!

    Im a Freelancer myself. I started 1 year and a half after quiting my previous job.

    Why did I did it? I was in the same company for 8 years, with no salary improvement (1% to 2% per year).

    I was desesparate…..for having a job that I really hated!

    So I did make a risky move. I have quit the job and invest all my time on freelance for digital marketing.

    I can say a few things in all this experience:

    – Leave only when you have at leats one client that you know that will stay with you for at least 3 months;
    – Save money for 3 months (as you said);
    – Work/study/scout clients 12 hours a day until you have everything under control;

    One year later I m earning 3 times more than I was earning in my previous work lololololololol

    However the downsize is the lonelyness (8 hours working alone for long periods of time can burn your brain lol).

    Well anyways loved your post and completly identify with it 😀

    I wish you all the best m8!

  3. I’ve been slowing working on freelance work as a screenwriter and I’ve been finally getting some work, though the pay is still nowhere near a point where I can quit my day job. The only point of advice missing from this great article is perseverance, if you really want to freelance and work for yourself, you can’t give up.


  4. Great ideas as always Joel. One thing is – I would assume that most people know to just not jump into freelancing blind and that they have some plan or safety net. Or at least it never crossed my mind that if I left my W2 and had $500 in the bank with no clients that it would work out.

    I finally switched down to freelancing when I got referred 3 clients in a row and I was physically not able to keep my full time job and the extra clients – so it was pretty clear at that point.

    Secondly, have you detailed your process of nabbing clients through Twitter and LinkedIn anywhere? Is it essentially about telling your story and teaching what you know and they inquire on their own?

    • Joel

      I haven’t written that up yet – but I will soon, if others are interested!
      i’m launching a new site for freelancers soon that will cover a ton of this 🙂

  5. A great common sense rebuttal to all the ‘just take the leap’ hype articles out there!

    3 month survival money is good; it’s enough to keep the lights on whilst hustling for the first few clients, but little enough to give you enough pressure / motivation to get up in the mornings and get stuff done.

    Looking forward to your next post!

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