7 Truths To Know About Freelancing Today

You know what I’ve realised over the last two months since I left my job to jump back into the world of freelancing?

It’s a LOT tougher than what I remember!

Three years ago, blogging and social media was a whole different ball game – that’s when I was a full-time freelance writer; before I went back to office life.

And as I sit here in a crowded coffee shop at 08h30 in the morning, typing away on my little notebook, I’m astounded at the number of people sitting here, like me, with their laptops, sipping on their cappuccinos.

It feels like everyone’s hopping on this freelance, blogging, solopreneur, creative, side hustle train.

It’s like this double-edged sword: cool because you’re surrounded by so many like-minded people. Yay!
Not so fun, because, well – have you tried waving your hand in the virtual world lately to get a little authentic attention without looking desperate? Yup. That. Getting your “voice” heard among a sea of “me, me, mes” isn’t all it’s cracked up to be.

Some days it’s downright disheartening to see what kind of things get the spotlight.

But you know what? I can’t complain… Not really.

Because complaining about having the luxury to sit in a coffee shop and do what I love every day is a HUGE privilege.
(Write every day, yes – coffee shop every day, definitely not… cappuccinos with soy milk aren’t exactly cheap!)

So, I thought I’d dig a little deep today and share a few freelance truths.

Truth: Freelancing has its perks: no micromanaging bosses, no catty coworkers, no dreadful traffic.


BUT it’s not all sunshine and roses, and if you’re thinking about jumping on this remote work train, there are a few things you need to know first…


There seems to be this huge misconception (and I know, because I’ve got it from friends before) that doing your own thing is super easy and fun – ALL the time. That you can just lie in bed till whatever time you feel like surfacing and pretend to work in your PJs all day.

Oh, I wish!

(By the way, kudos to you if you can rock those jammies and be super productive!)

Seriously though, I feel like it’s time to cut the crap, quit the filtering and fakeness, and just…


So here’s my two cents – and what I’ve learned from freelancing or working for myself over the years…

1) You’ll be tested to show up and be yourself – every single day

Whether that’s on social media or with friends who just don’t get what you’re doing, or even in your writing. It’s going to be hard; you’re going to want to edit and tweak and fake your way, because it’s just easier.

Even if it’s scary or embarrasing or for some weird reason, upsets other people.

The world has enough wannabes and copy cats.

People crave REAL and raw and honest. You were born with all your gifts and your amazing personality for a reason; don’t rob the world of who you really are.

2) Sometimes, you’re going to feel guilty for doing what you love

Guilty for sitting in a coffee shop and writing, guilty for trying to follow your dreams, guilty for not being stuck in traffic on a rainy day on your way to work, guilty for not following the crowd. Because in a perfect world – we’d ALL be doing what we want and getting paid for it.

The truth is: everyone has choices in life.

Even if those choices start small, on the side, after hours – and only materialise in a year or two.
Everyone starts somewhere and freelancing is flipping BRAVE.

So when that guilty feeling comes (and it will), allow it in. Embrace it. And then remember how hard you’re actually working, and count how many people you know who would have the guts to freelance full-time or work for themselves.

Exactly. Probably not too many.

Don’t feel guilty for rewarding yourself every now and then, because it’s those mini moments between the doubt and fear and overwhelm that makes it all worth it.

3) You really don’t need to “grow a thicker skin”

Way back when, I was told that I could never have my own business because I was too “soft”, “timid” or “shy”. Guess what? I did – I started and ran my own gifting business for 18 months.

I was also a freelance writer for three years. This whole hustle, slay, be fierce, conquer motivation is cool and everything – but not all of us are born extroverts.

For years, I let people tell me that being quiet was a bad thing.

I let people make me feel like sh@t. Now, I know that having a softer side, gentle heart and wanting to be kind is a super power. Sure it helps to have “thicker skin” in certain situations, but this notion that you’ve got to be tough and loud in business in order to succeed is old and boring.

Let’s move into the 21st century, please.

4) Your comfort zones WILL be broken

Don’t think you’re going to get all comfy behind your computer screen, send your amazing creativeness into the internet universe, and call it a good days’ work. Okay, maybe now and then. But the reality is…

I’m a planner addict, and I can’t tell you how many days I’ve sat here almost in tears because my rigid writing schedule just wasn’t working.

When I first started freelancing years ago, I thought it was a match made in introvert heaven; then I quickly realised I’d actually have to get OUT, meet people, talk on the phone (something I really don’t enjoy), and put myself out there. Every day, my comfort zone boundaries are pushed a little more – and as scary as it is, I know it’s the only way I’m going to grow both personally and in my creative career.

So embrace flexibility and know that you’ll be breaking some serious comfort zones along the way.

5) You’re going to have some really bad days

They’re coming, so prepare yourself. You’re going to have days when you question everything you’re doing…

  • Frustrating days when you get massive writer’s block and feel like your brain has turned to mush.
  • Overwhelming days when you just want to delete all your social media accounts and move to some secluded cabin in the woods and write your little heart out.
  • Sad days when you feel so lonely you could cry your eyes out.
  • Negative feel days when you just want to give up.

I’m warning you, they’re coming and... they never stop coming for us creatives.

I guess it’s the price we need to pay for doing more of what we love, hey? The good news though? They’re usually few and far between the good days… and there are some SERIOUSLY amazing days so embrace them.

When the crappy days come, I’ve learned to embrace them, too – not fight them, and just do something that’s not writing related. Like go for a run, watch a movie, paint, or binge-watch Undercover Boss. Just allow yourself to BE and do something that you ENJOY.

(And don’t feel guilty about it! Our creative brains need down time too because we’re constantly switched on).

6) It’s never going to go exactly as planned

I hate to break it to you, but if you’re a bit of a control freak or like things to go a certain way, you’re going to be in for a bit of a shock when it comes to the world of freelancing.

And, if you’re a perfectionist or a people-pleaser, know that this is going to be one of the hardest things you’ve ever done in your life.

You won’t always have perfect clients, or a perfect job, or a perfect day. And people are going to want to rip you off and take advantage of you so you’re going to need to learn how to say no, piss some people off, and take a bolder stand – even if it terrifies you.

7) You might lose some friends – but you’ll gain a few unexpected ones

Not everyone is going to fall in love with what you do – I know, harsh to hear, but true.

Because people react to you and what you do based on their own insecurities and fears.

The haters, the negative nancies, the once super supportive friend who’s suddenly acting weird – don’t take it personally; you’re reminding them of something they maybe want to do, but don’t have the courage to do it… yet.

Keep doing YOU and surround yourself with more people who support you.

As for the new friends?

You’ll be amazed at the kindred spirits you unexpectedly come across… it’s awesome!

Back in 2012 when I first started blogging, I “met” one of my closest friends, a free-spirited creative from North Carolina. Since then, we’ve shared countless emails, talked about everything from writing a book to the meaning of life. I consider her to be one of my closest friends, even though we’ve never physically met.

You’ll find awesome online buddies in the most unexpected places.


Keep an open mind.

Be flexible.

Embrace change.

Be prepared to break comfort zones on a regular basis. Own your strengths – gifts and personalities and be yourself. Be kind to yourself. Learn. Collaborate. Connect. And above all… find the positive and just ENJOY the journey. Because that’s what it is – one big journey and it’s exciting!

And if you don’t know where to start, just start small.

  • Start a blog or a side gig or a passion project
  • Save if you can
  • Jump onto freelance sites
  • Connect with other creatives

We live in the most exciting digital time – it’s really the BEST time to put yourself out there and do your own thing.

You’ve got this.

I love hearing about other creative journey – share your thoughts in the comments below! 

Feel More Inspired To Dream Big + Simplify Life Each Week

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8 Replies to “7 Truths To Know About Freelancing Today”

  1. After reading this, I don’t think I’d have the discipline for freelancing. I thought it was all coffee shops and getting up late. Great post! xx

  2. Being an entrepreneur isn’t for the faint of heart. The comfort zone thing is right on. Hehe. But I love it. I love the challenge of what it makes me do. And I have to know myself well enough to know that I still need interaction with other humans. The thicker skin part. Yes! That’s good. My skin isn’t all that thick…though I do cringe at the future one-star Amazon reviews, lol. That’s when I’ll come back here and say, MEL! HELP ME! lolol. Love ya, girl. You always make me smile! Fabulous post.

  3. I’ve been doing this for seven years now and I still love it. The day I stop loving it is the day I will do something else, but I don’t see that day coming. We are the storytellers of our generation, the voices of our generation, and our words will be read hundreds of years into the future . . . and I find that too cool for words. The fact that I get paid for doing this is just amazing to me.

  4. LOL! Aaaah, I hope I didn’t scare you off for good, Asha! Just so tired of all these “fluffy” posts about freelance life; figured it was time to get real.
    It is pretty awesome though, and I guess if you really wanted to – you could wake up later and work later, and visit all the coffee shops you liked! All depends on you and where you’re at in your life. 🙂

  5. It’s true though, hey? The breaking of comfort zones REALLY challenges us to do things we never thought we’d do! LOL. Anyone who leaves you a one-star review on Amazon needs their head checked I think; your work is AMAZING. Can’t wait to see your journal published soon! 😀 xx

  6. Bill, YOU are too cool for words. To do what you’re doing and keep doing and inspiring others to spread their writing wings… that’s cool.
    “We are the storytellers of our generation…” -> I love this! 🙂

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