u/Dear-Librarian-4085

I’ve been making invoices manually and I think I’m finally over it.

I do freelance translation work in Michigan and usually send somewhere between 6 and 12 invoices a month. Nothing complicated. A few repeat clients, the occasional new one, and most invoices only have one or two line items.

All I really need is something that creates a clean invoice, saves my client details and shows me what’s been paid and what’s still outstanding.

Maybe automatic reminders too, but that’s about it.

I keep finding invoicing tools with dashboards full of features I’ll never touch, or a “free” plan that turns into a trial once you start using it.

What’s the best free invoice software you’ve used that works well for something this basic?

I don’t mind paying later if the business grows. Right now, paying a monthly subscription to send 8 invoices feels unnecessary.

I’ve been doing freelance video production on the side for about four years while working a regular office job, and things are starting to pick up.

I’m based in Tennessee. Last year I only took on around 8 projects because I was still working full-time, but I’ve already booked 11 projects for the next few months and I’m seriously considering making this my main source of income.

That’s what has me thinking about the LLC.

I’ve been operating under my own name so far and haven't had any major issues. Most of my projects are in the $1,500–$3,500 range, although I have a couple of larger corporate jobs coming up that will be around $6,000 each.

So when should I open an LLC? Is getting more clients and moving toward full-time work a good point to make the switch, or am I overthinking the timing?

Part of me thinks I should just keep operating as a sole proprietor until the business is making a certain amount each month.

Another part of me would rather get everything structured before I leave my job and start taking on more clients.

I’m also trying to figure out whether there are other things I should have in place before making the jump, like a separate business bank account or insurance.

I know the answer can depend on the business and the state, but I'd like to hear how other freelancers approached the timing.

Did you form your LLC when you first started getting clients, when you went full-time, or after the business had reached a certain level of income?

I’m running a small service business and trying to settle on one payment platform for sending invoices and collecting payments online.

My monthly volume is still fairly low, so I’m trying to avoid paying a bunch of extra fees for features I don’t really need. At the same time, I’d like clients to be able to open an invoice, pay online and be done with it.

The things I care about most are fairly simple: reasonable card and ACH fees, quick payouts, easy invoicing and a payment link I can send to a client without making them jump through hoops.

I’d also like the option to pass a card processing fee on to the customer where that’s allowed, rather than absorbing the whole cost myself.

I’ve looked at Stripe, Square, Wave and a few others, but it’s hard to compare them because the pricing structures and payout times are all a little different.

What are small US-based service businesses using for this?

I’m less interested in which platform has the longest feature list and more interested in what has been reliable and affordable in actual day-to-day use.

We’re a wholesale food distributor in North Carolina with 9 people who regularly deal with suppliers and vendors.

Our customer support side is already handled through Zendesk, so I’m not looking for another customer-service platform.

The problem is our supplier side.

We work with around 80 suppliers, and different people on our team are constantly emailing or calling them about pricing, availability, delivery issues, product changes, invoices, etc.

Right now, a lot of that information is sitting in individual inboxes and spreadsheets. If someone is out of the office, it can be surprisingly difficult to figure out what was discussed with a particular supplier or who last spoke to them.

I’m looking for something that works more like a CRM for our supplier relationships. Multiple employees should be able to see the supplier record, add notes, see previous communication and pick up where someone else left off.

It would also be useful if we could keep things like contacts, contracts, pricing discussions and important documents attached to each supplier.

We’ve been trying to patch this together since early 2024, but it’s getting harder as the supplier list grows.

Do you use vendor relationship management software for something like this? I’m open to a dedicated supplier-management platform or even a regular CRM that happens to work well for supplier relationships.

I'm looking for a CRM for B2C and I'm finding that a lot of the recommendations seem designed around sales teams chasing leads.

Our situation is different. Most of our customers are already buying from us, and the challenge is keeping track of the relationship after the first purchase.

I'd like something where the team can quickly see a customer's history, previous purchases, conversations and follow-ups without having to dig through emails or separate systems.

It would also be useful if customer calls and messages could be connected to the same record.

If you have run a B2C business, what CRM are you using?

I'm less interested in sales pipeline features and more interested in something that helps a team manage a large number of individual customers properly.

I'm getting ready to bill my first freelance client in Canada and I'm starting to think I'm making this much more complicated than it needs to be.

I don't have a company, employees or anything fancy set up. It's just me doing freelance work and now I need to turn that work into an invoice.

The part I'm stuck on is knowing where the line is between "I can send this client an invoice" and "I need to set up a whole business before I can do this properly."

I've seen people recommend everything from making a PDF in Word or Google Docs to using proper invoicing software.

I'm also seeing a lot of information about GST/HST, business numbers and registration, and I'm not sure which of those applies to someone who's just starting out.

So if you were starting from scratch today, how would you do it?

Would you simply create a professional invoice with your name, the client's details, description of the work, amount, payment terms and payment instructions?

Or is there something specific a Canadian freelancer should have sorted out before sending that first invoice?

I'm not looking for the most sophisticated invoicing system. I just want to send a legitimate invoice, get paid, and keep proper records from the beginning.

When you had to send your first freelance invoice in Canada, what did you wish someone had explained to you beforehand?