One day you'll be dancing in your chair while making invoices 💃🏽

Tell the baby freelancers in your life.

The last time Belgium, the country in which I live, held elections several friends and acquaintances opted to run for office at the local level.

I remember how much it amazed me that we (because they were age peers) had apparently reached the age (i.e. early 30s) where that was a normal thing to do.

Well, readers, it seems like mid-30s is the age-appropriate time to start freelancing.

In the last few months, two very good friends of mine have made the leap to freelancing, as has a relative. This is admittedly a very small sample pool, but I still think my theory holds. Because when I think of the people around me who’ve recently taken up freelancing, a lot of them have been in their late 20s to mid-30s.

Based on my social circle, it seems that you either begin freelancing after graduating in your early 20s, as I did; or you venture into freelancing when you’ve found some stability in your salaried job, grown frustrated with it or otherwise find it limiting in your mid-30s.

I cannot tell you how excited it makes me that these three people in my life are giving freelancing a go. It’s also been an interesting experience to learn about their apprehensions and fears.

I’ve said before that the freelance industrial complex that exists today wasn’t around when I started out. But listening to these newbie freelancers, I’ve started to wonder whether that was possibly an advantage. The more information there is on how to set up, and what formalities to fulfill, the more you perhaps feel like you’re barely scratching the surface in terms of what you need to know.

Setting up as a freelancer is of course incredibly overwhelming, but like so many things, it gets easier over time. As I’ve told all three of them, making mistakes is a normal part of freelancing (never mind, you know, the human experience) and no-one is going to seize their flat because they billed a client with the wrong VAT percentages (that’s sales tax for our non-EU readers).

Exhibit A: It took me hours and hours to create my first invoice (in Word no less). I think it looks okay-ish now, but it has a weird €4 discount. Don’t ask me why. I also sent it … by … snail mail?

Today, in my 12th year of freelancing, creating invoices is one of my favourite things to do. Because: 1) the promise of sweet, sweet money, and 2) I can zone out a little and put on my Spotify “Jams” playlist while making invoices.

Exhibit B: The first time my accountant alerted me to a mistake I had made on an invoice, I 100% had a little meltdown.

These days, I’m usually the one to alert my accountant to a mistake I’ve made (there could possibly be a correlation with the aforementioned zoning-out), and telling him I’m leaving it as is because it’s not worth the hassle of issuing a credit note and a new invoice to correct a teenie mistake.

I now know that there’s a difference between wilfully dodging taxes and making a small mistake on one invoice out of dozens, and that if I ever get audited, this would not be the kind of error that would land me in tax jail. And white-collar criminals rarely go to jail anyway, ha!

Exhibit C: I stuffed all the receipts for my expenses in a box in my first year of freelancing, making tax filing time a nightmare.

There’s no upshot here. I’m a terrible human being and still do this.

Exhibit D: Remember that first invoice I told you about? I sent it two weeks after completing the assignment because I didn’t want to seem too eager for the payment.

Today I will send invoices the same day or a day after filing an assignment if I’m able to and could not care less about the optics of that. So many of the factors that determine when I get paid are outside of my control, and promptly sending out an invoice is one of the few things I can do to speed up the payment process. (I’m currently awaiting payment for work I completed in November of last year, deep sigh.)

In addition to keeping track of and filing my stupid expenses, there are a lot of other things that remain a struggle – being assertive but not “difficult” ; finding the right balance between well-paid but unfulfilling work and interesting but low-paid work; breaking out of the isolation that’s built into solo employment, etc. But the paperwork side of things I have mostly gotten down after more than a decade of freelancing.

That’s also consistently the message I’ve been giving these three people. Everything will get easier once you’ve done it a few times. Also, don’t be afraid to ask for help. It is a blessing to have people around you who have taken the freelance route before you did.

As always, I’d love to hear from you. How do you look back on your first year as a freelancer? What kinds of mistakes did you make and what would be your top tip for newbie freelancers? I’ll share your best tips in a subsequent newsletter, and with the three new baby freelancers in my life.

Speak soon,

Linda