By Georgina Laidlaw

Starting Strategies for Would-be Freelancers

By Georgina Laidlaw

Few freelancers get there by waking up one morning and deciding to start a business that day. On the other hand, to the part-time freelancer longing to sever the ties of paid employment, the decisions involved in moving to full time freelancing can seem intractable.

There are a few common transition strategies you can use to make the change. While everyone’s experiences are different, because each of us is an individual with our own competing priorities and challenges, hopefully you’ll be able to take some elements of these ideas to formulate your own approach.

Save a buffer

Yep, that old chestnut. If you can swing it, great! But for many of us, there’s simply not enough spare cash in the budget to save enough of a buffer to support ourselves for three months without work, or whatever it is the pundits advise.

Land a whopper

Landing a whopper of a freelance job — one that’s big enough to justify you resigning from work, as a sort of freelance stepping stone — is a nice idea, and again, if you can manage it, good on you.

For me, this wasn’t an option. My work tends to entail smaller projects, and I’m happy with that as a freelancing model: it means variety. Also, for many freelancers who may have done a few jobs as independent operators, the chances of landing a job that’s big enough (or pays well enough) to justify leaving secure employment completely are slim.


Take a short contract

A short-term contract that uses the skills on which you’ll base your freelance income can be a good alternative strategy — it’s the one I used to transition to full-time freelancing.

By taking a contract, you can build up your folio in certain areas, make new contacts in the industry, and establish your reputation in — and potentially beyond — an organization that needs your skills. If they ever have extra work, they’ll know where to come!

The other benefits of this approach are that it can get you out of entrenched-employment mode, provide mental space for network-building and strategy-making, and give you the time to take on additional, smaller jobs that can help build your business before you make the leap.

Supplement your income

Plenty of freelancers I know subsidised their freelancing during the initial phases by taking part-time work in unlikely places. Some taught their profession in night school, others worked casually in cafes, others built small online businesses that were comparatively self-sustaining and generated a reliable, if small, income that they could use to cover some expenses.

Sites like 99designs, Learnable, and the SitePoint Market might be worth looking at if you want to take this approach — but there are plenty of options out there.

Many business owners argue that this approach distracts you from your business — that if you’re going into business for yourself, you need to plunge in and spend all your time making it work. Fair enough. But for those who are interested in pursuing an untethered lifestyle, and don’t want to build a growing business so much as a freelance income, this can be an option. It does require discipline, though — otherwise, you may wake up one morning and find that your freelancing dream has seen you quit a good job to bus tables three days a week, get lonely, and live on cup noodles.

Something you should know…

An assumption that’s implied in many conversations about freelancing is that if you get the transition strategy “right”, you’ll be set up — you’ll be off and running, and you’ll never have to worry about money again. As if your transition strategy should springboard you to freelancing security.

Those words — “freelancing security” — are something of a contradiction in terms. Ultimately, security is a state of mind, not of circumstance.

But whatever strategy you choose, you may find x months down the track that you’re struggling to find work, you’re not generating the income you need, and you’re down to the cheapest brand of cup noodles. That may not happen, but it may. That’s something to be aware of — not to worry about.

None of these strategies is a silver bullet. You have to be your own silver bullet. When times get tough and work dries up, you’ll need to rely on your own skills and integrity to get things going again. It sounds like a small thing, but for those who have never been self-employed, it can be extremely intimidating.

Do you have what it takes? Yes. The more you freelance, and the more earning approaches you try, the more clearly you’ll be able to see that you can rely on yourself to earn an income. Just don’t make the first leap bigger than you can manage.

Do you have a strategy to transition to full time freelancing? Have you already done it? Tell us how in the comments.

Image courtesy stock.xchng user lusi.

  • Jcalebm

    Freelancing isn’t easy, from my experience it makes it worse when you sell your time for a low price because of desperation.

    Also as a freelancer you have to wear many hats, do many jobs at the same time, and that includes being a web developer/designer and salesman, each of these could be challenging.

    Miami is one of the worst places for freelancing.

    • Sumit Gope

      I think this is not true,Freelancer are getting peanuts for their project because they are accepting the project at a very low price and spoiling the freelancer’s market.This should not be done.

  • Andrei

    At the begining, it was really hard, the first 4-5-6 months. As Jcalebm said, you have to work on several projects at the same time. Also, at the begining, to attract clients, i did work for a low price.
    But important is not to focus on one place to find work (freelancing websites for example). I found freelance work in newspapers, even job search engines (where normally they are looking for full-time employess).
    One of the advantages of ferelancing, besides the variety of work, are the experience itself, of being self-employed, and the opportunities. One of your clients might have a business idea, and you might be invited to join, on afull-time job.
    Best of luck to you all. And congrats sitepoint, keep it up

  • Muhammad Omar


    Thanks for highlighting these very important points.

    It’s now been 8 years since I’ve been doing jobs as Software Engineer (mainly Web Applications Development) and now I guess is the time when I should start working as a Freelancer.

    I believe to start working as a freelancer one must at least have some small to mid term contract that should generate good enough income to bare at least the minimum on your budget and you can then capitalize on that in due course of time…

    Finding good business is not easy and finding good developers is also not easy …

    Muhammad Omar

  • Cory

    My advice? Just freakin’ do it already. I would say most people OVER THINK themselves right out of freelancing. Why? Is is risky? Yes. It is scary? Yep. How about unpredictable? Very.

    However, is it going to kill you? Are you going to lose all of the skills that got you to where you are right now. No on both. So trust me, take the leap, and at least test it out. You’d rather go on with life knowing you tried, right? You at least owe yourself that satisfaction.

    Take it from me. I stumbled around with this question for years, plugging away at a good job, but not a job that I saw myself doing forever. I jumped ship, with nothing in hand but a handful of skills and a friendly voice that actually communicated with clients (key point here), and have made it nearly two years now. It’s been lean, really lean. I’ve got a house full of kids to feed and a mortgage and everything… and they don’t dig ‘cup noodles’ every night, unfortunately. No big vacations, no new cars – but I have seized back some precious time with my family, got REALLY used to working without a boss, and had some clients turn into great friends that really make me dig what I do.

    The light at the end of the tunnel?… I just finally scored my first ‘whopper’ that starts this summer. Finally, some real money, and a FANTASTIC opportunity to get some upper-end contacts and some big names in my portfolio. Did I see this coming a couple of years ago? Only in my dreams. And trust me, I have tried to give up a number of times, only to realize that I still have a handful of good clients that I don’t want to give up on, and just stuck to it.

    Sometimes things are easier if we just close our eyes and go for it without thinking about the potential disaster ahead. Just go into it know that there is always some way out. And have fun while you’re at it!

  • Pete

    What i think has been overlooked is the value of having good contacts in your industry. Ive been freelancing for a few years now, starting only to provide myself some pocket money whilst at university, and in all of that time ive managed to earn a decent living through just a handful of clients.

    The fact of the matter is that small companies in my industry (Web Development) have a harder time finding the right employees than they do finding work, and a trustworthy, reliable freelancer can easily fill the gaps without the company needing to commit to paying someone a fulltime wage (and all the other associated costs).

  • Freelancer work is the only way here, I am not earning much about 900 dolars a month…. to much less to take care of my familly. I will “kill” for stable paid employment and spare cash :(

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