Don't get SaaD. Get Rippling.
Disconnected tools don’t speed you up – they slow you down. That’s SaaD (Software as a Disservice).
Rippling unifies HR, IT, and Finance so you can save time, cut costs, and grow faster.
Find out if you and your team are at risk of SaaD today.
📃 Does your invoicing “system” suck?
If you’re still opening a Word or Google Doc, changing the date, and updating the line items every time you send an invoice… please know you are too talented for this.
That’s not an invoicing system. That’s a tax season nightmare.
An invoicing system isn’t about being fancy. It’s about visibility.
You should always be able to answer:
What invoices have I sent?
Which ones have been paid?
How much money is currently floating in the void?
When you use an accounting tool instead of a Word doc, those answers are always a click away. Because these platforms don’t just create invoices, they also track them.
They connect directly to your bank account so when a client pays, the software automatically recognizes and matches the transaction. Or it gives you the ability to match things directly in one place.
That’s the difference between “I think they paid?” and “Payment cleared yesterday at 3:42 PM.”
Option 1: The Freebie — Wave Accounting
If you’re a freelancer or solopreneur just getting started, Wave is your new best friend.
Free invoicing + accounting (no catch)
Accept online payments directly from your invoice for a small fee
Tracks who’s paid and who hasn’t
Connects to your bank so you can reconcile payments quickly
Wave will flag overdue invoices, remind clients for you, and keep a running list of everything outstanding.
Option 2: The Middle Ground — FreshBooks
If you’ve outgrown “free but functional,” FreshBooks is an excellent low-cost options (~$19/month).
This gives you more automation and polish:
Automatically match payments from your connected bank or Stripe account
Handle partial payments and recurring invoices
Generate reports on overdue or aging invoices
Track time and expenses in the same place
Option 3: The Big Kids System: QuickBooks Online
Once you have multiple clients, contractors, or recurring income streams, it might be time for something like QuickBooks Online.
Connects to your bank and credit cards for full reconciliation
Tracks sales tax, income categories, and expenses automatically
Matches payments to invoices in real time
Generates financial reports easily
Generally loved by accountants at tax time
It’s around $30/month, but you get an actual accounting system that shows you, at a glance, what’s been invoiced, what’s been paid, and what still needs chasing.
Quick Setup Checklist
Pick your platform (Wave, Freshbooks, Xero, etc.)
Connect the bank account(s) you want to track - these should include wherever client payments live
Set up your invoice branding and default line items like the services you offer or items you regularly sell
Add your current clients (or just add them as you need to send invoices)
Optional: Connect payment accounts like Paypal or Stripe so they can pay directly on the invoice.
Now when you need to send an invoice the template is ready to go and it’ll be automatically tracked in one place.
Pro tip: Schedule a weekly or monthly finance check-in with yourself to review overdue invoices
🤓 SINCERELY
This is one of those moves that pays off every single time.
An invoicing system is about about protecting your time, your energy, and your cash flow. You can’t plan your next project, pay yourself consistently, or even decide if you can take a break if you don’t actually know who’s paid you and what payments are due.
Manual invoicing might feel scrappy, but it’s secretly draining. It keeps your finances in a constant state of “I’ll check later,” and that mental tab stays open way too long.
Automating and centralizing this part of your work means you can send an invoice and move on with your life, confident that the system will keep score for you.
You deserve a business that treats your time like it’s valuable.
Coming Soon: Creative Support Systems
Earlier this summer I led 130+ people through 12 weeks of getting un-stuck creatively. The feedback was overwhelmingly positive and changed my life, personally.
I’m turning that exercise into an 8-week self-paced course and community to build your creative practice, silence self-doubt, and finally do the work that matters consistently.
You’ll be the first to know when enrollment opens.
Want this in your inbox? Subscribe to TODAY TODAY for weekly emails.