Within the past couple of weeks, I handed in my notice, after spending over fifteen years working in-house as a designer of websites and magazines for a publishing company. This wasn't a quick or easy decision; but the time feels right to strike out and apply everything I've learnt both through the job — and in spite of it — to working for myself as a freelancer.

In the months, even years, that I spent thinking about this change, a lot of thoughts went through my mind about what makes a good freelancer, and what makes a not so good one. If you're thinking about making a similar change, these are a few questions that I felt I needed to ask of myself. It's best to reflect on this stuff before you take the plunge.

1. Is freelancing really for you?

This sounds like an obvious question, but do you want to be a freelancer? Spend a little time thinking about whether you really, really want to do it. Not liking your day job, wanting more control over your destiny, or feeling your creativity is being stifled may be good reasons for a change, but moving to a new job with a new company might be better than diving into the unknown.

Give it a try. Keep up with the day job for a while, and pick up some freelance work on the side. If you can't find any such work, or you can't fit it in to your already-busy lifestyle, or it just seems like too much to do, then maybe it's not for you. If you're thinking of whipping away the safety net of regular paychecks and somebody else calling the shots, you'll need to take on some more responsibilities, and you'll need to get more organised. If you find that you can seek out freelance work that goes beyond doing cheap jobs for friends, and you're disciplined enough to carry it out without completely ruining your social life/free time/TV time/cream cake-eating time/etc, that's a good sign.

2. Do you run screaming from change?

Big news: freelancing is very different to working in-house. That's a given. However, it may not only be a big change on the first day after you've made the switch; it will change, mutate, morph and munge itself into a different animal very regularly, as priorities switch, work ebbs and flows, and new skills and opportunities both present themselves and demand your attention.

Working within a company, you will be used to being in groups. Even if you don't regularly work in teams, you will still be used to entering an environment with other people every day, and having conversations and interactions with a wide range of human beings. It's likely that you will be used to dealing with a monthly paycheck so that you instinctively know the health of your cashflow, and unless you're either the Big Boss or part of some super-hip collective, somebody else will basically be telling you what to do, and when to do it.

All of this will change as a freelancer: you may well be on your own for the majority of your time, with only daytime TV, pets and tasty beverages to keep you company. You will have to decide what you do, how, and when, in a way that satisfies your creative urges whilst making sure that the bills get paid. On that note, you may get paid hugely different amounts month to month, depending on how work is going and when you're expecting payment on projects. Now, that may all be super great, and make you very happy: if, though, it instils terror, focus on the fear, and establish if you've got it in you to deal with it every day, and potentially for a very long time.

3. Are you good with money?

You may not be all about the Benjamins, but as a freelancer you'll need to keep an eye on where the money's coming from, where it's going, and hopefully how to make more of it. This ugly financial stuff can often sit uncomfortably with the concept of a cool freelance lifestyle, but you'll need at least a decent grip on things.

Wherever you are, it's almost definite that you need to pay tax. Find out what form this takes, when you need to pay it, and make sure that it gets paid. Tax isn't optional — maverick non-conformism doesn't tend to work well with the IRS, the HMRC or whatever acronym controls this stuff in your country.

As an in-house guy or gal, you'll be used to a regular paycheck. Plan to pay yourself in a similar way, and work out how much you'll need to make a month to cover that vital tax stuff as well as your costs (equipment, food, transport, offices, etc) whilst also providing enough money to go out and have fun at least a few times in between projects. Aim to pay yourself as much as you were used to receiving from the day job, if possible. If you can maintain financial equilibrium as you switch from one work lifestyle to another, it'll keep a lot of things simple, as you won't have to assess every single little financial decision to make sure that it fits with your new situation. If you can, save up at least three months' worth of paycheck money.

Other things to think about? Pensions. Savings. Costs of working from home, if that's what you will be doing. All of these outgoings may have been more straightforward whilst working in-house; as a freelancer, it's all on you. The upside of all of this? It's all on you. You're in control.

4. Are you Mr/Mrs/Ms/Sir/Rev Organized?

If you're in-house, you're part of a greater organizational structure. Whether or not you think it's being done right, or you agree with how it's carried out, any company that's more than a couple of people in size will have systems, hierarchies and channels of communication. All of that stuff is the oil that eases the cogs of the company machine, but when you're working for yourself there are still fundamentally valid reasons for being organized.

Time management is a big deal. You'll need to or be able to estimate pretty closely — how long it takes you to do things, when you need stuff to be done, how many things you can do at once, and how the time you're using relates (or not) to the price you're charging for your time. Don't underestimate the time you'll need for boring stuff like admin, writing emails, deploying code from one repo to another and so on. Remember that you want enough time to do projects well, and to give thinking time to challenges in order to come up with a creative solution — that's one of the reasons you wanted to go freelance in the first place, right? Make sure, too, that you leave some time in your schedule for a bit of what makes life worth living — fun, relaxation, hobbies, significant others, or whatever. It's within your hands to choose your preferred work/life balance.

Project management is time management's sexier sibling. Get on top of your workload, arrange it into piles on a desk, stick Post-it notes on things, pay for software to send you reminders; do whatever it takes. At a simple level, at any point during any day you'll need to be able to answer this question: "What's going on with [Insert name of project here]?" Depending on the kind of work you take on, you may either be organizing yourself alone — in which case you should have a feel for how much you need to trick yourself into getting stuff done — or, more likely, you'll be juggling several projects' worth of work, communication and reporting. There are a billion ways of doing this stuff — make sure you have one.

Get a routine. Your freelancing life will consist of doing work, finding work, telling people about the work you're doing, looking after the health of your business, and doing that not-insignificant stuff like eating, sleeping, disco dancing and watching YouTube videos of red pandas getting frightened. Plan out your month, and make sure that it includes daily/weekly/monthly tasks like paying bills, checking and answering emails, sending project updates, and so on. You'll want to get a lot of stuff done so that the actual fun creative part of a freelance lifestyle isn't confused and distracted by 'all of the other stuff'.

"Take this job and shove it!"

You may not need to quit your day job with quite such a confrontational phrase, but if you've found that you can answer the four questions above positively, freelancing may well be for you. It could be the best thing you ever do. And if it isn't? Refer to question two above — embrace the future and all it may throw at you, and good luck.

Have you taken the plunge into freelance work? What tips would you share? Let us know in the comments.

Featured image/thumbnail, taking the plunge image via Shutterstock.