New freelancers and creatives are bright-eyed and bushy-tailed. They are full of excitement, they don't know what they don't know… which ultimately leads to their first downfall.

Starting something new always tends to lead to mistakes … which isn't a bad thing necessarily. I'm a huge advocate of learning through mistakes, provided that you actually learn from the mistakes you make and not continue to make them…

As a new freelancer, it can feel like a world full of overwhelm and decision-making, not being fully aware of what you should be doing where and freaking out because you're scared that someone will actually find out what you're up to!

If any of this sounds like you, you're not alone.

When I started out freelancing, I was forever worrying about whether I was doing things right, did the client really like the work I did and what would happen if my current employer found out what I was doing?!

Below are some fatal flaws that I see time and again in new freelancers. Following these, you'll find how you can fix them if any of them resonate with you (ie, you're making these mistakes now!)

Five Fatal Flaws of New Freelancers & Creatives

Mistakes new freelancers & creatives make and how you can avoid making them too. Click through to read more.[bullet_block style=”size-16″ small_icon=”15.png” width=”” alignment=”center”]

  • No support network/peer group
  • Not setting your own deadlines
  • Not telling clients when something went wrong
  • Consuming the wrong kind of content
  • Not taking your freelancing business seriously


When I started, the above five things nearly sent me to an early freelancing-death… I learned the hard way what not to do. If you want to avoid heart palpitations, 3am sweats and a general overall sense of foreboding, read on to learn how you can address and fix these flaws now.

How to Fix the Flaws

One thing you'll need to learn quickly as a freelancer, is that you need to admit to yourself, very quickly I might add, just when things aren't going quite as well as you'd expected they would.

This is the first step in identifying flaws and fixing them. If you can't admit to yourself when you've made a mistake or when something isn't running as smoothly as it should, then you'll continue to make those same mistakes and head to entrepreneurial death.

End of sermon.

Let's start at the beginning…

1. No support network/peer group

You might be in business by yourself, but that doesn't mean that you should be doing things alone. And don't think you can talk about this stuff with your friends and family, they'll (often) be the first to tell you what you're doing is risky and fill your head with more doubts or reinforce those self-doubts already floating around in there.

Stop. As much as your friends and family are awesome, they may not share your unique view on the world. And that's ok. You won't always see eye-to-eye on things and this is just one of those times.

So what can you do to rectify this? Start by finding an online place where you can connect with other's that are doing what you're doing. Whether that's on a blog (like here!) or forum, just find somewhere where you can chat to others about what you do.

Facebook and Twitter are also great places to connect with others and if you're into meeting up with people face-to-face, a local group could be a good option too.

For me, I found an amazing community of people in Location Rebel. I have been apart of this community for over 3 years now and I still chat to the same core people that I met when I joined. They are my posse.

Here's a quick list of resources you can tap into where you can connect with like-minded peeps:

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If you are blessed to have super supportive friends and family, then by all means, chat away with them about what you're doing. But for those of you that don't have that or do but want to chat to others who are actually DOING what you are, then a few of the options above will help.

2. Not setting deadlines

Yes, I know that the client will set deadlines for you, but one of the biggest mistakes you can make is not setting a deadline for yourself that is different to that set by your client.


Because shit happens. It's really that simple. If you're doing your freelancing gig as a ‘side hustle' this is even more important to do.

Life gets in the way, other things come up, and if you don't set your own deadline that is 24-48 hours PRIOR to the client's deadline, you could find yourself not only in hot water with the client but also potentially without pay, a lost client and a bad rep.

None of this is good for a successful freelancing career. Nothing says, “I don't care about your project” more than a missed deadline!

Get yourself sorted asap. You can probably allow this to happen once and that's it, no more chances.

I use a variety of tools to keep on top of client work. I ALWAYS set the deadline for myself 24 hours prior to when the client needs it and if it's a new client, 48 hours before.

You can keep it simple and stick with something like Google Calendar and create multiple, coloured calendars to keep track of your client work, or you can take it up a notch and use something like Trello or Freedcamp (both offer free options).

I use Trello for managing all my writers and Freedcamp for all my client work. You can do the same or stick with Google Calendar.

The point is to ensure that you use something to keep track of your project deadlines and set up deadlines for yourself that are early so that you always have a buffer in case the worst happens… it's far easier to miss your own deadline and make it up than miss a client's deadline and let them down.

3. Not telling clients when something went wrong

This was something that I really battled with in the beginning. I was so scared of my clients! I had given them all this power, when in reality, they were no different to me when it came to communication and problem-solving. After all, they are just people too (well, most of them were…!).

The way to approach issues, particularly when you hit a snag in a project, is to simply send your client an email and let them know.

I've found that by being upfront and honest and letting them know immediately when something's wrong, they are far more receptive.

And if you follow that up with a proposed solution or a way to fix the issue, even better.

Don't make the mistake of burying your head in the sand and avoiding a tricky conversation. Put yourself in their shoes and think how you'd like to be told about it and then take action.

The longer you sit on ‘bad news' the worse it will be for you and your client.

4. Consuming the wrong kind of content

I'm sure you're familiar with the saying “you are what you eat.” The same goes for what you expose your eyes too; “you are what you read/watch/see.”

When you become an entrepreneur (yes, that's right, YOU'RE an entrepreneur!) you begin to look at the world differently. Long nights in front of the TV start to feel ‘wrong' and those funny YouTube video's you like to watch—kind of a time waste now.

I'm not saying you can't still watch your fave TV show or watch silly YouTube video's, but you do have to watch how much of this stuff you're consuming.

It takes a special resolve and skillset to make it as a successful freelancer, so in order to do that, you're gonna have to step outside the norm and read non-fiction books, listen to podcasts and watch training video's that will help you move forward in your freelancing career.

“Ok Lise, what the heck are you on about?!”

Ok, ok, I know I'm sounding a little vague here, so let me clarify. In order to live a life you want, it means you have to change what you're currently doing. And in order to do that, it means you have to consume different things, learn about (and master) aspects of this lifestyle that you're not otherwise exposed to in your normal life.

So instead of watching your fave TV programme every night, record it and batch watch it on the weekend. Instead, watch a training video or two that shows you how to deal with clients, read a book on email marketing or listen to a podcast about creating the lifestyle you want.

Here're some resources to get you started:

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The point I'm trying to make here is that if you want to lead a lifestyle on YOUR terms, watching TV is not going to get you there!

5. Not taking your freelancing business seriously

This is probably THE biggest fatal flaw I see new freelancers making time and again—not taking their business seriously.

I'm not sure why we do this. Maybe it's a lack of confidence in our abilities or lack of knowledge, but it was definitely something I did in the beginning.

I would often put off little things, like setting up my bookkeeping system or getting a proper invoicing system in place. Instead, I would focus on just getting new business and working with clients.

Other things I would treat casually was communication with clients and the importance of keeping track of how many hours I was spending on client work.

I would often refer to my business as a ‘hobby' when talking with friends, which further highlighted (to them) that this was just a passing fad.

Don't do this. Don't sell yourself short.

Approach your business like you do your ‘normal' day job. Put systems in place, get a logo created, set up your invoicing and bookkeeping systems and get everything lined up so that you're good to go when you're ready to transition from your job into full-time freelancing.

Because that's your next step. World domination!

If you're sitting here reading this and thinking to yourself, “oh man, this sounds way too much like me!” then stop berating yourself and do something to fix it! Take action right now.

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I'd love to hear from you about your experiences with any of the above. Leave a comment below and let me know how you dealt with it or if you need help!

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Lise Cartwright
Lise Cartwright

Founder of Hustle & Groove and your creative business strategist. If you want to get notified of new posts just like the ones you see here, then make sure you join the awesome H & G community — Join Now!

    4 replies to "5 Fatal Flaws of New Freelancers & Creatives (and How to Fix Them!)"

    • […] Find out how you can fix the remaining 4 flaws at Outsourced Freelancing Success. […]

    • Aleksandra

      I was really in a group 5 for a long time, not because I was lazy or didn’t want to work, but because I didn’t immediately understand some things about freelancing. You see, the thing about freelancing is that you get involved in all of that really fast and in no time you can get a big client community without even learning how to deal with it in the first place. Therefore you’re not really prepared and don’t really have the idea of what you’re getting yourself into.

      • Lise Cartwright

        Completely agree Aleksandra! Which is why it’s so important to take a step back and set your business up the right way. Then once all of that’s done, you can get back to doing what you do best!

    • […] can happen a lot if you don’t have some checks and balances in […]

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