It’s OK to fail

You’re a professional, and professionals have to be good at their job, right? Professionals don’t make mistakes, they are always thinking 5 steps ahead, and they deliver. So why are you, a person who is claiming to be a professional, falling so far behind, and getting overwhelmed? Why is your project going off the rails, and your client getting frustrated?

Because you’re failing.

But that’s OK.

Failing is normal – natural, even expected. You can’t be an expert on everything all the time, and even when you are an expert, mistakes happen all the time. It’s an unfortunate side effect of being human – sometimes we make mistakes. Even more unfortunate is that our clients are also human, so sometimes the mistake doesn’t come from us at all. Sometimes there isn’t even a mistake anywhere at all, and things can still fail.

Your job as a freelancer is to be an expert-for-hire. Obviously clients who are paying for an expert expect a level of quality that they couldn’t achieve themselves. This can lead freelancers to present themselves as an expert on all aspects of a project, even parts that they’re not particularly comfortable with. As a result, it’s common for a freelancer to promise delivery of a service that they’re almost wholly unqualified to provide. Once they realise their mistake, they’ll double down on work (obviously at no extra cost to the client), and end up delivering a sub-par product, or just not delivering at all.

Where does failure begin?

The first step towards failure is ignoring the signs that it’s coming. Even when it’s entirely unavoidable, recognising it early can turn “nothing got delivered, and now I’m dodging client calls,” into “95% is up and running, and we’ll re-asses the remaining 5% later.”

Worse than the fear of failure is the fear of admitting failure, because that leads into the world of impostor syndrome, and the fear that you’re not really a professional at all. This fear of appearing unprofessional leads to the worst decision making you’ll ever perform, and only serves to set you up for bigger failures in the future. I have personally handed out days of work, entirely free, because I was afraid to admit to a client that I made a mistake while quoting. This either led to me under delivering on the final product, or over delivering, and setting unrealistic expectations for future work.

Avoiding a difficult conversation isn’t making you more professional, it’s preventing your client from strategising, and ensuring that things will be much worse later. Even if you’re able to “hide” it from your client, you’re doing so at the cost of your own mental health (and often your financial wellbeing).

Accepting failure.

In reality, not all failures are equal. Sometimes they can actually be beneficial, or even intentional. In the start-up world, there’s a mantra of “fail early, fail often” – essentially “find out if something won’t work before you invest too much time and energy into it.”

While this isn’t an ideal philosophy for life, it can inform your decision making process, and help you to actually be more professional. The absolute worst time to surprise your client with a failure is the day that the project is due – the second worst time is the day before. Keeping your clients informed allows them to make decisions early, and mitigate any damage caused. Surprising them with bad news when it’s too late to respond to it will only sour the relationship.

Seasoned professionals fail frequently, but have processes in place to communicate, adapt, and mitigate failures. It often looks like they’re super-stars who can do no wrong, because instead of falling, they fail with style. They accept that some things are outside of their control, but put into place strategies to mitigate the potential fallout. They find when something won’t work early, and look for something else that will. They don’t avoid failure, they accept that it’s just a part of the process, and use it to learn and grow.

So the next time that you’re feeling overworked and underpaid, think about how you got there – what steps you could take in the future to avoid it again. Think about how even the largest companies fail frequently, but in small ways. Remember that just because you can’t see someone struggle doesn’t mean that they aren’t. Most of all, remember that you’re just human, and no matter how much knowledge or experience you have, some things are simply outside of your control.

Communicate your failures early. Communicate them often. Don’t just communicate them with your client, but talk about them with your community and your peers. Maybe if we all talk a little bit more about how we’re not perfect we can start to break down some of the stigma that causes impostor syndrome, and causes a real drain on our mental health. Then maybe we can learn how to fail better instead of less.

For more tips, tricks, and thoughts on freelancing, please look through our other posts.

Working towards routine

One often overlooked aspect of full-time, salaried, in-office jobs is routine. Your tasks may change from day to day, but there’s a built in “start”, “end” and general structure to your work day. When you start freelancing, then suddenly you’re free to leave in the middle of the day, or start late, or just take a whole day off whenever you feel. There’s no set routine, and no expectations except those that you set for yourself. Great, right?

The importance of structure

It is great, except for when it swings back the other way. You took Monday of, but you still have work to complete, so on Wednesday you pull an all-nighter to catch up. Thursday is meant to be spent on a new project, but you’ve had no sleep, so you start after lunch. Productivity is poor so Thursday bleeds into Friday, and before you know it you’re cancelling plans with friends because the whole weekend is spent playing catch-up.

Structure in your working arrangements can feel constricting, but it also helps you to plan, set realistic expectations, and maintain a realistic work/life balance. A massive trap in freelancing is abandoning the 9-5 structure, and getting yourself stuck in a burnout spiral.

Setting expectations

The other aspect of working without a routine is that clients don’t know/understand when you’re available. When you’re starting out, you’ll probably try to impress clients by being constantly available, no matter what. This gives your clients the expectation that you’re always available, always willing to help, and that you don’t have a life outside of responding to their requests.

This will quickly turn toxic. It’ll start with a small but urgent request at 4:59PM, and end with complete projects being handed to you on a Friday so that they can “have it ready for Monday”. Eventually you realise that you don’t get any time off, there’s no “cutting out early”, you’ve had a nasty cough for 5 weeks, and just one more all-nighter might actually kill you. Obviously this isn’t sustainable long-term, and it shows clients simply not respecting you – you become a magical “work” machine.

Creating a routine

Start easy – set business hours for yourself. For convenience, there’s some business hours that a lot of the rest of the world already agrees to. They might get fuzzy if you have a client outside of your regular timezone, but in general you can set your business hours, and go from there.

Once you have business hours, communicate them to your clients – work is not guaranteed (or even likely) to be performed outside of those hours. Any work that has to be performed overnight or on a weekend comes at a premium – that’s your time, and they have to buy not just your skills but your leisure time, too. Note that if you choose to work outside your business hours that’s on you, but if the client requests it, they should pay the premium.

Next, start planning your projects out – try to dedicate solid blocks of time to a single project. If you have a number of small tasks for multiple projects, block them in together as a single task for yourself, or attach them to larger tasks for the project. Try to minimise context switching, because it kills productivity.

When you have blocks of work planned out, you can start filling in your schedule – to begin with, try to only fill half your day with “must do” tasks, and have a few floating “can do” tasks that you can pick up. The reason for this is because humans are terrible at scheduling, and you’ll probably find yourself taking up to twice as long to do your tasks than you expect to. As you start getting used to how much work you can actually achieve in a day, you can start scheduling more (and larger) blocks in. Any days where you have 2 hours or less left in your schedule, and you’ve completed everything you wanted to, congratulations! Now you can take off early, and enjoy that sweet freelancer life.

Eventually you’ll get your routine down, and you can start shifting hours – maybe do a half-day on Wednesday, or make every weekend a long weekend. You set your business hours, and you set your routine. With planning comes consistency, and with consistency, you can plan to make use of your free time. Remember that there’s always going to be “admin” tasks for your business (reconciling accounts, looking for more clients, following up with existing clients, learning new skills). These can work into your routine, and help to keep yourself healthy, and your business on track.

For more tips, tricks, and thoughts on freelancing, please look through our other posts.

Be prepared for downtime


It’s a scary word in all professions, but it gets even scarier when your income relies directly on you being able to perform. Deadlines start to slide, you find amazing new ways to procrastinate, bills are coming in but you’re not sending them out. It can quickly spiral out of control, and I should know – I’ve been there many times.


Just as scary. There’s no clients, no work, and your bank account is running low. There’s a drought in your pipeline, and you’re really not sure if you’ll ever get a job again. You start considering those clients that have more red flags than the Soviet Union. Maybe your prices are too high, maybe you’re too picky, and maybe this strange guy asking for your bank account details really will deposit $80 million from a deceased Nigerian prince.

But as terrifying as the “Boom or Bust”, or “Feast and Famine” of freelancing can be, these both have a common solution.

Planning for downtime

The first step is accepting that you are not, in fact, an automaton. You have to eat, sleep, go to the toilet, and occasionally even have some fun. Without that, you won’t survive. Accepting that you can’t work 24/7 can lead to the realisation that you can’t work 16/7 for very long either, and maybe even 10/5 is pushing it a bit far. There’s only so many years in a row where “time off” means “total immune system failure” before you burn out for good.

Once you have accepted that you need to work sustainable hours most of the time, you can start planning the hours that you do work better. Start scheduling clients so that you’re only working on one or two major projects at once. Consider charging “day rates” or even “week rates” instead of hourly, so that you can dedicate an entire day to a single project without distraction.

Next start planning your salary. Sure, you get paid into your paypal or your bank account, and then you spend it straight from there, but maybe that’s the problem. Try opening an account for your business at a different bank – one that takes a day or so to transfer money to your regular account. This makes it difficult to pull money out on a whim. After that, start paying yourself a salary every week, or fortnight, or month – whatever works best for you. The salary should be consistent, not just “whatever money I have available”. Pick a number that’s easy to cover. Start putting aside money for tax from every time you pay your “salary”, and leave the rest of your business income right there – in the business bank account.

After a while you’ll notice that it’s grown to the point where you could pay your next salary twice. Here comes the magic trick:

Stop working

Take a week off. Maybe two. What can your salary cover? Use the money saved to pay yourself leave without having to worry about where your next pay cheque is coming from – you’ve already saved it.

After you’ve done this once, start building up your “time off” kitty again. Use it when you’re feeling overwhelmed, and to keep yourself afloat when clients run thin. Use that time off to get your mind on track without stressing, or to learn a new skill, or just to go through your shoe-box of business expenses so that your accountant doesn’t fire you.

After a little while, you’ll get used to the stability of a consistent income. You’ll be less inclined to take on too much work, or take on bad jobs when it’s slow. You don’t have to stop working on your business, but you can start spending your time on improving your business instead of procrastinating.

Making time for downtime is vital to surviving long-term as a freelancer – take it from someone who learned this lesson many, many times over. In the past few years, I’ve gone from working 52 weeks/year (and being miserable) to working 42-46 weeks in a year, and earning more. While I still get stressed, I know that I can always afford to take a week at the end of a big project to rest, recoup, and recover for the next one.

For more tips, tricks, and thoughts on freelancing, please look through our other posts.