Simple Accounting & Invoicing Tools for Retirees

business resources May 07, 2025

You Don’t Need to Be an Accountant to Run a Profitable Business

Let’s be honest—most people don’t start a second-act business because they love bookkeeping. But if you want to keep more of what you earn (and avoid tax-season headaches), a simple system for tracking income and sending invoices is essential.

Here’s the good news: you don’t need a finance degree or a complicated spreadsheet. You need the right tool that works for you, not vice versa.

This beginner-friendly guide is designed for retiree entrepreneurs and solopreneurs who want to:

Send invoices confidently and look professional
Track income and expenses without stress
Prepare for taxes without scrambling
Use tools that are simple, affordable, and built for one-person businesses

💬 “You’ve run teams, raised families, and managed life. You can manage a business budget—with tools that make it easy.” — Curt Roese, Retirepreneur

Let’s simplify your financial toolkit—so you can focus more on what you love and less on paperwork.

👉 Tools for Small Business Retirees

What Retiree Entrepreneurs Really Need from Their Financial Tools

You don’t need a whole accounting department. You need clarity, simplicity, and peace of mind—especially if you’re running a solo business or part-time service.

The right tools should help you feel in control of your money without eating up hours of your time.

🧾 Core Features That Actually Matter

When choosing accounting or invoicing software, look for these essentials:

Simple invoice creation - Create and send branded invoices in minutes—no formatting headaches
Payment integration - Let clients pay via credit card, PayPal, or ACH with just a click
Expense tracking - Easily log what you spend on supplies, subscriptions, or marketing
Tax prep reports - Export your income and expenses for your CPA—or DIY tax software
Dashboard or overview - A clear visual of how much you're earning, spending, and saving

✅ Tip: Avoid “enterprise” or corporate-level software. You don’t need complexity—you need visibility.

📉 What You Don’t Need

Skip features designed for larger teams, like:

Payroll for multiple employees
Inventory management (unless you run a product-heavy business)
Complex integrations or financial modeling tools

You’re likely not running a multi-department operation, and that’s a good thing. The best tools are designed for solopreneurs and microbusinesses.

Top 4 Easy-to-Use Accounting and Invoicing Tools for Retirees

These tools are perfect for retiree entrepreneurs who want to get paid, stay organized, and keep it simple. There are no complex dashboards or finance jargon—just what you need to manage your business money confidently.

1. Wave – Best All-Around Free Option

What It Does: Invoicing, payment tracking, expense logging, basic reports
Why It’s Great: 100% free with no monthly fee
Best For: Freelancers, coaches, and consultants who want to keep costs down
Standout Features:
- Branded invoices with your logo
- Accept credit cards and bank transfers
- Easy tax-time summaries

✅ If you’re starting and want a complete, no-cost solution, Wave is a top choice.

2. Square Invoices – Best for Service Providers Who Need Fast Payments

What It Does: Quick invoicing, online payments, recurring billing
Why It’s Great: Known for simplicity and trust with clients
Best For: Local services, consultants, health/wellness providers
Standout Features:
- Mobile app for on-the-go invoicing
- Pay via card, Apple Pay, or Google Pay
- Built-in tipping and reminders

💡 Great if you use Square for payments or want to look polished from day one.

3. FreshBooks – Best for Client-Focused Freelancers or Coaches

What It Does: Time tracking, invoicing, expenses, proposals, project-based reports
Why It’s Great: Built for solo professionals who serve multiple clients
Best For: Coaches, designers, service-based businesses
Standout Features:
- Send professional estimates or proposals
- See which invoices are viewed or overdue
- Integrates with Stripe, PayPal, and Gusto (if needed)

🟡 Plans start around $17/month, but the ease-of-use may be worth the cost if you’re earning regularly.

4. PayPal Invoicing – Best for Simplicity and Familiarity

What It Does: Create and send invoices quickly, track payment status
Why It’s Great: Most clients already have PayPal and trust the brand
Best For: Low-volume service providers or one-off projects
Standout Features:
- No monthly cost—only transaction fees
- Works well internationally
- Add taxes or discounts easily

💬 “If you already use PayPal for personal use, this is the easiest next step.”

How to Choose the Right Tool for Your Business Type

Not all retiree businesses are alike; your accounting tool should reflect that. The key is to match the tool’s features to your workflow and income style, not the other way around.

Here’s a breakdown to help you choose based on your setup:

If You’re a Coach, Consultant, or Freelancer

Best Choices: FreshBooks or Wave
Why: You’re likely sending recurring invoices, tracking time, and working with a few key clients
What to Prioritize:
- Easy invoicing with client profiles
- Payment reminders
- Clean income reports

✅ FreshBooks is ideal if you want more insights and client management features. Wave is great if you’re just getting started or prefer free.

If You Run a Local Service or Trade Business

Best Choices: Square Invoices or PayPal
Why: You need quick, mobile-friendly ways to send invoices and collect payments on the go
What to Prioritize:
- On-site invoicing via smartphone
- Ability to accept credit card payments easily
- Simple interface and fast setup

💡 Square works well for dog walkers, handypersons, tutors, and consultants who invoice after appointments.

If You Sell Products (Digital or Physical)

Best Choices: Wave or PayPal
Why: Simple invoicing, basic inventory support, and integrated payments
What to Prioritize:
- Ability to accept multiple payment types
- Track income from various product types
- Simple receipts for buyers

💬 You might also look into platforms like Etsy or Shopify if you sell online—those have built-in payment systems.

If You Need the Basics (and Want to Keep It Free)

Best Choice: Wave
Why: It covers the essentials—invoice, track expenses, download reports—without a subscription
What to Prioritize:
- Clean design and dashboard
- Support for taxes and deductions
- No pressure to upgrade if you don’t need extras

🟢 Start simple. You can move to a more robust platform later if your needs grow.

Quick Start Guide: How to Send Your First Invoice and Track Payments

Getting started doesn’t have to be complicated. With the right tool, you can send your first professional-looking invoice and track your income in less than 15 minutes.

Here’s how to do it—step by step.

🧾 Step 1: Choose Your Invoicing Tool

Pick one of the tools mentioned earlier (Wave, Square, FreshBooks, or PayPal).

💡 Tip: Start with Wave or PayPal if you're testing the waters—they're free and easy to learn.

✍️ Step 2: Create a Branded Invoice Template

Most platforms will walk you through setting up your first invoice. Here’s what to include:

Your business name (or your name if solo)
Your logo (optional, but looks polished)
Client name and email
Invoice number (start with #001 or use today’s date)
Due date (net seven or net 14 is common)
Service description (e.g., “1-hour coaching session”)
Amount owed
Payment methods accepted

✅ Add a short thank-you note: “Thanks for the opportunity to work together. Please reach out with any questions.”

💳 Step 3: Send It and Enable Payment Tracking

Hit Send directly from the platform—it’ll email your client the invoice with a payment link
If using PayPal or Square, your client can pay with a credit card, debit card, or their account
Set up automatic reminders for unpaid invoices (most tools offer this for free)

📈 Step 4: Track Your Payments

Once the invoice is paid:

The system will automatically update your income dashboard
You can view all outstanding invoices, income history, and export reports for taxes
Some tools let you send receipts automatically

💬 “Tracking your payments weekly helps avoid tax-time surprises and keeps your business financially healthy.”

Final Thoughts: Keep It Simple, Consistent, and Stress-Free

You don’t need to be a bookkeeper or spreadsheet wizard to run a financially sound business. With the right tools—and a simple routine—you can stay organized, look professional, and enjoy getting paid for your work.

Let’s recap your path to confidence:

Choose a tool that matches your business and comfort level
Send your first invoice with clarity and ease
Track income and expenses weekly—just 15 minutes can make a big difference
Stay ready for tax time with clean records and simple reports

This isn’t about perfection. It’s about control and peace of mind.

💬 “The sooner you simplify your finances, the sooner you’ll free up energy to grow your business—and enjoy your retirement even more.” — Curt Roese, Retirepreneur

You’ve got the experience. Now you have the tools.

✅ Frequently Asked Questions

What’s the easiest accounting software for retirees running a small business?

Wave, QuickBooks Self-Employed, and FreshBooks are all beginner-friendly. They offer simple dashboards, invoicing, and expense tracking tailored for freelancers and solopreneurs.

Do I need accounting software if I’m only making part-time income?

Even part-time income should be tracked for tax purposes. Software helps you stay organized, track deductions, and prepare for quarterly or annual filings.

Can I create invoices without hiring an accountant?

Yes. Most accounting tools include invoice templates you can customize with your logo, pricing, and terms. Some also automate reminders and payment tracking.

How much do accounting tools typically cost for solopreneurs?

Many tools have free tiers (like Wave) or low-cost plans under $25/month. These usually include invoicing, expense tracking, and basic reports suitable for small-scale businesses.