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Business success is dependent on a solid financial foundation & success looks different to everyone & there is a lack of equity of access to resources and information for small business owners and independent contractors & there is a societal narrative making us believe “balance” is our ultimate goal & … There are so many “&”s that impact being your own boss. Let’s have some frank discussions on the basics of business with a holistic focus on everything that helps business owners define and find success.
Molly Beyer: [00:00:08] Welcome to The Ambiguous &: Business Basics and Beyond, the podcast where we have frank discussions on the basics of business with a holistic focus on everything that helps business owners define and find success. Each episode is a reminder that success isn't one thing, it's a whole lot of ambiguous ands. Like, subscribe, or follow, and let's explore these ambiguous ands.
[00:00:35] Hello and welcome to The Ambiguous &: Business Basics and Beyond! I'm your host, Molly Beyer, and I'm here to lead you through frank and holistic conversations on the basics of business. We're on to the second in our 'Systems that Save Sanity' series, where we're diving into a topic that every business owner has a relationship with, and many have a complicated relationship with, and that's invoicing and payment collection. I know it's not the sexiest part of running a business, but it's one of the biggest sources of stress for many of my clients. Most business owners I encounter have invoicing systems that are, let's call them, aspirational. They really want to stay on top of it. They mean to send invoices on time, but they're often wearing all the hats and juggling all the clients and trying to present themselves as someone who has it all organized. Here's the part that most of them don't talk about: they feel guilty about invoicing. It's like asking for money is an inconvenient disruption to the relationship instead of a healthy part of doing business.
Molly Beyer: [00:01:42] One of my clients was so far behind that when they finally sent out their invoices, one of their clients emailed back saying, "Thank you. I was wondering if I was supposed to remind you.", and I know that one hurt. It's not that the client meant anything unkind because my client knew they weren't running a business in a way that matched the values and the expertise that they were providing, and so it really hurt. This also isn't a unique story, and these moments are really a turning point when business owners decide to reach out for help. I meet a lot of clients when they're in this moment, because invoicing isn't just a task, it's really an energetic exchange. It's how we honor our work, and honor the client relationship, and honor the stability of the business that we're building. So a healthy invoicing system, really, it gives you that cash flow stability because that's the heartbeat of your business. You need money to be coming in. It also is a space for clarity and professionalism because your clients know what to expect. You can build confidence because you know you're leading instead of reacting, and it can give you a lot of calm because you're not then chasing and guessing or resending anything when it comes to getting paid. When your invoicing becomes predictable and consistent, it's going to free up more of that mental and emotional space, which is the real currency for a business owner.
[00:03:11] Let's get to this fun part. In the episode description again, you're going to find a workbook that's going to go along with this series to help guide you through the start of your systems. In your workbook for the invoicing and payment systems, you don't need to use the workbook anyways. You can go through this just through the podcast, but there's a full checklist in there. And we're going to walk through these major pieces in a way that really feels approachable and doable. So you want to think of this system as having four pillars. The first is how you're going to generate your invoices. Are you going to create them manually using a software? Are you going to set them up as recurring? How are you going to deliver them? Are you emailing them? Is there a client portal or some sort of automation? How are your clients going to pay you? Can they pay you through ACH or credit card or an online payment link, or are there payment plan options? Is it all still super traditional cash or check mailed to your business, and how do you follow up? Do you have automatic reminders? Do you have any personalized nudges? Are there any late payment procedures that you have? When these four pieces are working together, your invoicing stops being an emotional roller coaster and becomes a good rhythm for you.
Molly Beyer: [00:04:27] Just like with your onboarding, you can build out this invoicing system in one of three ways. So we're going to break down the manual, the software approach, and then as well as the AI assisted. So for our manual approach this is really a great space if you're early in business or if you're really just keeping it simple. So this could just be something like a Google doc, a word template, it's creating an invoice spreadsheet. Then you can manually turn into a PDF and email. You could have tracking your payments just in a simple checklist or spreadsheet or something like that. And this really works as long as you're consistent with it. The biggest thing is just recognizing when that moment of consistency starts to slip. That's when it's time to upgrade. Again, we're always talking about reflect, review and revise. Going through this process, things are going to change as you move through the stages of your business.
[00:05:28] Then we want to look at this software approach. Most established businesses are here. This is where they shift to, is this software space. We've got tools like accounting software like QuickBooks, FreshBooks, Wave, Zero. You can use those for invoicing and bookkeeping. There's also tools like Square or Stripe that take the automatic payments. You can create automated reminders and recurring billing through these systems. The beauty of the software is that it really reduces a lot of human error, and it takes out a lot of human emotion. It creates reliability, but taking out that human emotion is a big piece too, because even if you're creating things manually, we get caught in that same trap where you start to sometimes feel bad about asking for money or reminding about money. If you've got it in a software system that's automated and going out, the software doesn't feel any emotions, it doesn't care. It just knows that you're telling it what you need to get paid, and it's telling the person, this is what we need to get paid and by when. And if you don't, I'm going to remind you. It's a great space to move into.
[00:06:39] Let's then move into this AI assisted approach, because there's a lot of things that AI can do for you. It can draft reminder emails that sound like you. It can create invoice descriptions to help your clients to understand what it is they're paying for. It can build follow up templates for you. You can also use it to analyze your payment patterns and things like that from the data that you're receiving back. You can also ask AI to suggest improvements to your processes. So the key with this is it's really it's your voice. It's your values. It's your boundaries. AI tools just really help you to execute them faster. So here's a moment to take a quick pause. Because yes, mechanics are important, but mindset shapes really this entire system. A lot of overwhelmed business owners struggle with invoicing not because they lack a process, but again, because these emotions are getting in. They feel guilty. They feel behind, embarrassed, unsure how to set boundaries, afraid of coming across as pushy. So I want to say this clearly to anybody who needs to hear it. You deserve to be paid. You deserve to be paid on time, and you deserve a system that really supports that reality. The moment you allow invoicing to become a natural, neutral, predictable part of the relationship, everything changes. I'm going to say it again. You deserve to be paid, and you deserve to do it without getting all of your emotions tied up in the process. Like all of our systems, we want to have some very specific review touch points to really help keep this system healthy. Because remember, we want to reflect, review and revise as often as we need to to make sure these systems continue to stay relevant for our business.
Molly Beyer: [00:08:38] Our weekly touch points we want to send any new invoices, review payments received, and then follow up on anything that's overdue. Our monthly check points reconcile payments, yes, this matters. Reconcile your systems please. You want to review any unpaid invoices and start looking for any patterns that you're starting to see. Are there clients who are consistently not paying on time? Are there certain types of clients that aren't paying on time? Where in the system are you seeing patterns that can possibly have room for improvement? And then quarterly, you want to evaluate your payment policies. You want to review terms, fees, any software costs, and update any templates or reminders based on what you've learned through these reviews. So remember, this regular review is really where wisdom meets data, and it's where clarity gets easier. So our growth stretch is I want you to choose one of these things. Either turn on some automatic reminders in your invoicing software, create yourself a template for late payment follow up, draft a kinder but firmer invoice email tone using AI, or add one additional payment option for your clients. So you only need one stretch to change your entire relationship with this aspect of your money movement.
[00:10:01] So some highlights in the workbook for the worksheets for this time for this episode, you're going to find an invoicing workflow that's going to again include those manual software and AI versions, some best practices for payment collection, the review touchpoints that we talked about, some money mindset reflection, and then our growth stretch and a space for our notes and patterns. So walk through this slowly because this is really where transformation starts to begin for you. Invoicing really isn't about asking for money. It's about honoring the value that you provide and keeping your business stable so you can keep serving from a place of peace, calm, and intention so your system doesn't have to look like everyone else's. It just really has to support you.
[00:10:46] The next episode, we're going to shift into scheduling and meetings, and this is another area where chaos loves to creep in. But a good system really restores that sanity. Thanks so much for hanging out with us again today. We'd love to hear your feedback on today's episode as well as any requests for future content. Drop a comment or suggestion and join us next time for more frank and holistic conversations on the basics of business. Please also like, subscribe, or follow so that you never miss an episode. And until next time, I am Molly Beyer. And this has been The Ambiguous &: Business Basics and Beyond. Have a wonderful day!