5 rules for handling common freelancer challenges

No job is without its difficulties. That was something I began reflecting on when I received an email yesterday featuring the words “freelancing” and “happily ever after.” While I’m all for the power of positivity, I also believe it’s naive (and somewhat patronising) to ignore freelancer challenges in their entirety.

Do I sound a little negative? Trust me, I’m not. There’s a fine line between negativity and remaining realistic. If you want a truly positive outlook on your self-employed lifestyle, that’s an easy lesson to learn in advance and a difficult one to absorb retrospectively.

Rather than listing what the commonest challenges are, I’m going to try and provide you with management mechanisms. Are you ready? Let’s go…

Find time for other stuff

Freelancer challenges
CC: Matheus Mendes at Unsplash

Some of the most dominant articles out there on striking the right balance as a freelancer suggest that this lifestyle will eventually give birth to a massive degree of freedom. Although that’s true to an extent, I’m a strong believer in establishing balance from the beginning. Why? Because the quickest route to feeling disenchanted and becoming less productive is to live for your work and hope that the slack will ease.

When you pay close attention to everything else in your life that brings you joy, your modus operandi for becoming a freelancer in the first place isn’t too far from your consciousness. For me, this means being more present for my child, having free time to see friends when I need to, and being able to tend to my hobbies and aspirations. Freelancing gives me greater control over my earning power, which means I’m more likely to complete my PPL.

Anticipate freelancer challenges from external sources

Freelancer challenges
CC: Sam Manns at Unsplash

I may have mentioned this in a previous post (or two) and I will probably continue to mention it. Unless you have friends and family who are understanding, they’ll present challenges to your life as a freelancer in their own way.

For example, your partner/spouse/other half may not feel delighted when you choose to switch your day job for self-employment. Your family might mistakenly believe that working from home adds seven extra hours to the day, giving them the chance to land all and every menial task in your lap. Once or twice, I’ve had friends ask me when I am returning to work.

Erm, I am working?

Meeting the freelancer challenges that come from external sources requires self-confidence and a sound belief in what you’re doing. It’s also worth accepting that, no, not everyone will understand what you’re doing with your life. Oh, and you’ll need to assert yourself a little too. I’ll visit that below.

Start your day in the right way

Freelancer challenges
CC: Brooke Lark at Unsplash

Every so often I toy with the idea of writing a book about famous people’s morning routines. Instead, I’m writing one about history’s most controversial women. I can shelve the first idea, for now.

Starting your day in the right way is a lot like setting the tone for everything that lies ahead. I love the phrase setting the tone, as it was one that we used regularly when I worked for British Airways. Our managers would encourage us to “Set the tone with a warm welcome,” so that customers would enjoy a pleasant flight. Realistically, we were trying to hurl hundreds of people through the boarding doors in a short space of time to make sure we didn’t miss our flying slot. That warm welcome was rare.

Anyway, you can set the tone for your own day by discovering what it is that will make you feel good about your morning. Four days a week, my partner gets up at 4.30am to go swimming. Initially, I made more than a handful of passive aggressive digs about how tired I was as a result. Then, I accepted that he was starting his day in a way that worked well for him and that it wouldn’t kill me to try and do the same.

Eventually we decided he would buy a fitness watch with a silent alarm to avoid waking me up too early. Most of the time I am awake by 5am and I seize the opportunity to do three things that transform my morning routine:

  • Enjoy a coffee in silence
  • Meditate
  • Yoga (NB: I am currently following a YouTube yoga channel called ChriskaYoga, which is all kinds of excellent if you need a gentle Hatha routine first thing in the morning)

On some days, I will also do this: blogging. Then I will move onto the aforementioned book about history’s most controversial women. I feel like easing myself into the day with the things I love spurs my motivation and reminds me why I love freelancing so much.

Oh, and like many people, I write a decent list.

Redirect anger wherever possible

Freelancer Challenges
CC: Simon Rae at Unsplash

Another element of my morning routine is listening to podcasts while I make breakfast. At the moment, I am sort of binge listening to the 10% Happier podcast. I wouldn’t say I am quite the same type of ‘fidgety skeptic’ as the host, Dan Harris, but I do like the doses of science that come with a lot of episodes.

I’m around 30 episodes in at the moment. One theme that comes up regularly is the idea that meditation can help you redirect your anger. It’s like a prophylactic measure if you use it at the start of your day, hence my dedication to meditating in the morning.

Studies certainly back up the use of meditation for reducing anger. One found that those who meditate for just 20 minutes experience a reduced heart rate, lower blood pressure, and a reduced respiratory rate when they encounter stressful situations.

Stepping away from anger as a freelancer is absolutely crucial. Trust me when I say that some clients can and will push your buttons. I’d say it’s a small minority, but when they go hell for leather on the antagonism front they’re just like the keyboard warriors you’ll find in any section of a tabloid article.

When such scenarios happen, you have two choices. You can either sit with your anger, observe it, and release it. Or, you can let it take control of your day and turn you into a snarling unproductive mess.

If you can redirect anger, do it. It’s going to make your life a lot pleasanter.

Learn how to assert yourself, when necessary

Freelancer Challenges
CC: Thomas Kelley at Unsplash

With that said, there are times when you’ll need to assert yourself. Just like in physical workplaces, people will take advantage of your nice nature if they suspect (correctly or incorrectly) that you’re a pushover.

As a freelance copywriter, I’ve found that the following scenarios call for gentle assertion:

  • Clients asking for extra information that will take me outside of the word limit. I respond by saying “Of course, but which section should I delete to accommodate it?” Never work for free. Ever.
  • Revision requests asking for a different approach that isn’t outlined in the brief. If clients aren’t specific in their brief or they fail to provide extra details when I ask them if there’s anything else I should know, additional and lengthy requests are unreasonable.
  • Feedback that resorts to personal insults. These are the times when I decide it’s time to break up with a client.

If you suspect that you are a bit of a pushover, consider using assertiveness training. One study has found that it reduced stress levels amongst high school students. If you remember high school in the same way that I do, you’ll know it’s a mind-screwingly stressful time.

Do you have any common freelancer challenges? Whatever they are, feel free to pitch in with suggestions for managing them.

Honesty disclaimer: Like many of my posts, this one may include the occasional affiliate link. I add them in an attempt to make residual income, and I only ever link to products and/or services that I genuinely find useful myself.



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