7 Bookkeeping Habits Successful Entrepreneurs Swear By

Successful bookkeeping practices to keep you organized for 2025 and beyond.

Bad bookkeeping is the kryptonite that weakens even the most passionate entrepreneurs. It’s taken down more business owners than we can count.

And trust us, we’re not just throwing shade here. 

According to the U.S. Small Business Administration, poor bookkeeping is one of the top reasons small businesses bite the dust. All your hard work, your dreams, your passion — derailed by numbers that don’t add up.

It hurts, doesn’t it?

And, if you’re not careful, these little bookkeeping slip-ups can drain your productivity, eat away at your resources, and make your money look like it went through a razor-sharp and brand-new shredder 🥺

You get the point, right?

But don’t you worry — we’ve got you.

doola’s All-In-One-Accounting package is built to help entrepreneurs like you navigate the bookkeeping minefield for years, and after talking to businesses of all shapes and sizes, we’ve found some simple, smart bookkeeping habits that successful entrepreneurs swear by. 

And let us remind you, even these go-getters had their messy moments at the start. They’ve felt the panic of misplaced receipts, the anxiety of looming tax deadlines, the frustration of not knowing where their money is going.

But these bookkeeping habits turned out to be total game changers for them. We’re not promising miracles here, but we do promise fewer bookkeeping mishaps.

Let’s dive in.

7 Bookkeeping Habits for Entrepreneurs

Mastering these 7 entrepreneurial bookkeeping tips could be the difference between staying afloat and thriving as an entrepreneur. 

Let’s jump right in and make sure your finances are working for you, not the other way around.

1. Get Professional Help to Prepare Tax Returns

As an entrepreneur, you’re constantly pulled in a dozen different directions.

Marketing? Yes.

Sales? Absolutely.

Customer support? You’re on it.

Talk about exhaustion levels! 

With so many plates spinning, it’s easy to see why the thought of diving into tax prep on your own might feel like one more thing pulling at your sanity. 

That’s exactly why outsourcing the headache of tax filing to an expert can be a big relief.

Instead of spending countless hours untangling financial statements or nervously second-guessing tax forms, sometimes the smartest move is to hand it over to someone who lives and breathes numbers. 

A professional accountant or CPA can be hired, not only to make sure everything is above board but to actually improve the way you handle your finances. Their trained eyes can often catch things you wouldn’t even think to look for.

Take tax deductions, for example. You may not know about every deduction you qualify for, but a professional does.

For instance, one entrepreneur thought she’d be writing a check to the IRS until her accountant found overlooked deductions that saved her over $1,000 — turning her expected payment into a small refund. 

That’s the kind of difference expert help can make.

So while you focus on growing your business, leave the tax stress to a professional. They won’t just help you get through tax season; they’ll help optimize your finances and potentially save you more than you realize.

2. Hire a Bookkeeper as You Scale — Because Doing It All Yourself Will Only Get You So Far

Let’s face it — there comes a point when doing everything yourself just isn’t going to cut it. As your business starts to grow, one of the smartest moves you can make is hiring a bookkeeper. 

Yes,  you’ve probably been handling the books on your own up until now (maybe with a little help from an accounting app), but as things scale, so does the complexity of your finances. 

That’s where a bookkeeper can step in and provide you financial clarity.

A bookkeeper doesn’t just keep track of your expenses and send out invoices — they help you make sense of your numbers, stay on top of cash flow, and ensure you’re not missing any crucial financial details as you scale. 

Whether it’s managing payroll, tracking expenses, or making sure all your tax paperwork is in order, a bookkeeper can become your financial right-hand person.

You don’t have to do it all alone. Asking for help — whether it’s hiring a bookkeeper or just reaching out for advice — is one of the best habits you can develop as a business owner.

3. Keep Your Hands on the Wheel — Don’t Go Completely Hands-Off With Bookkeeping

Outsourcing your bookkeeping can be a lifesaver, but that doesn’t mean you should disappear from the process entirely.

Even with someone else managing the books, it’s important to stay in the loop. 

You wouldn’t let someone else take over completely while driving on a new road and just sit back without paying attention, right? You still need to know where you’re headed or where your next pitstop is.

The same goes for bookkeeping. What you see and what your bookkeeper sees are two very different perspectives.

You’re the one living and breathing your business every day, and that gives you insight into the intricate details that a bookkeeper might miss.

Your bookkeeper might be trained to spot patterns in numbers, identify potential issues, and streamline processes, which is incredibly valuable. But they won’t always have the same on-the-ground context that you do. 

For example, you know exactly why you chose to give one customer a discount or which clients are consistently late with payments. You understand the reasoning behind sudden spikes in expenses, like buying new equipment to handle a surge in orders.

These are details that might just look like data points on a report to a bookkeeper, but for you, they tell a much deeper story about how your business is functioning.

That’s why it’s crucial to stay involved. 

Here are some key areas where your insights and a bookkeeper’s expertise need to align:

✅ Profit: You know the “why” behind your numbers, while your bookkeeper can show the “how” to improve them.

✅ Expenses: You understand the purpose of specific expenses, but your bookkeeper might see trends that you’ve overlooked.

✅ Receivables: You know which customers are consistently late, but your bookkeeper will track the impact on your cash flow.

✅ Profit per customer: You can spot which clients bring long-term value, while your bookkeeper crunches the numbers to show it.

✅ Customer journey: You know how customers find you, but your bookkeeper can help you analyze how that translates into actual revenue.

When you combine your on-the-ground knowledge with a bookkeeper’s financial expertise, you get a full 360-degree view of your business.

4. Invest in the Right Bookkeeping Software

When it comes to bookkeeping software, this isn’t the place to pinch pennies. The right system can completely transform how you manage your business finances.

You want something that works for you — not just an off-the-shelf solution that’s been around forever, built for accountants who speak a language you don’t even understand.

With so many software options available today, there’s no reason to struggle through an outdated, complicated system that takes more time to figure out than it’s worth. 

You need a software that aligns with how you work — something intuitive that you’ll actually want to use, not something that leaves you staring at a screen wondering if you need a degree in finance to figure it out. 

The right software does two things really well: it simplifies your life and grows with your business.

Maybe you’re starting small now, but you’ll need something that can handle bigger things as you scale up. 

Consider features like automated invoicing, expense tracking, and report generation before investing in a bookkeeping solution. These capabilities can save you hours of manual work and give you instant visibility into how your business is performing.

Take a look at some amazing bookkeeping software out there.

5. Document Your Bookkeeping Processes

When it comes to bookkeeping, documenting your processes is like giving yourself a roadmap for the future.

Here’s why it matters: as your business grows, you won’t be handling every financial detail yourself. Maybe you’ll hire a bookkeeper, or maybe someone on your team will start managing the numbers. 

Without documented processes, everyone could be doing things their own way — making it harder to catch mistakes or stay consistent. One person might log expenses differently, or miss a step when invoicing clients, and that’s where things start to unravel.

Documenting how you handle invoices, receipts, expense tracking, and financial reporting gives you control and helps you avoid costly errors. Plus, it allows you to easily track your financial history — so if you ever need to backtrack, like during tax season or an audit, you have everything laid out.

Think of it this way: if you document your expense tracking process, for example, you know where every receipt should go and how to categorize each transaction.

It might seem like a small or unwanted step, but it prevents headaches when you’re looking for where that mystery charge came from months later. 

So, even if your business is small now, start documenting your bookkeeping processes. It’ll save you time, prevent mistakes, and keep everything running smoothly, no matter who’s in charge of the books.

6. Keep Your Expense Receipts

It’s impossible to know how much you’re really spending if you don’t keep track of every single receipt.

Sure, credit card purchases are easy — you’ve got the statement to back you up.

But cash expenses? That’s where things get tricky.  

Entrepreneurs often tell our CEO, Arjun Mahadevan how those “minor” expenses — like grabbing a quick bite with a client or buying last-minute office supplies — fall through the cracks. They remember the purchase but forget to record it, only to face confusion during tax season when they can’t account for those dollars.

The only way to avoid this costly bookkeeping mistake is to keep all expense receipts safe.

Some people carry a notebook to jot down every cash purchase (more power to them), but honestly — who’s got time for that? 

Instead, take a cue from successful entrepreneurs who use accounting apps to snap pictures of their receipts on the go. No more paper clutter, no more lost receipts. Everything’s right there in your phone when you need it.

This small switch can give you complete peace of mind.

7. Track Your Receivables

So, you sent out an invoice. Great! But did you get paid?

Sending an invoice is only half the battle — following up and actually getting paid is where things can go off track if you’re not careful.

Take John (name changed for privacy reasons), for example. He runs a small design business and was so deep into client projects that he just assumed his invoices were being paid on time. But they weren’t.

The problem? John was so wrapped up in his work that he completely lost track of the money coming in (or not coming in) from his clients. When he finally sat down to take a look, he realized he had a stack of unpaid invoices — some of them months overdue.

He didn’t have a system in place to track who had paid, who hadn’t, or how much he was still owed.

And John’s not alone.

This happens to a lot of entrepreneurs, especially when they’re managing multiple clients and trying to track everything with just one bank account. It’s easy to lose sight of who owes what.

That’s where the right accounting tools come in handy. Tools like doola Bookkeeping, QuickBooks and FreshBooks don’t just track your invoices; they flag the ones that are overdue and even send automatic reminders to your clients. 

Another great option is Xero, which offers similar features. It not only tracks your receivables but also provides an easy-to-read dashboard showing exactly where your money is at any given time.

So, instead of relying on memory or manually tracking each invoice, let these tools handle it. This simple adjustment ensures you stay on top of your receivables and get paid on time.

It’s Time to Simplify Bookkeeping With doola

You know how Mary Kay Ash once said, “Don’t limit yourself. Many people limit themselves to what they think they can do. You can go as far as your mind lets you. What you believe, remember, you can achieve.”

It’s a good reminder, right? Especially when you’re juggling all the hats a business throws at you — bookkeeping, taxes, customer service, and everything else in between.

And while the mantra is to keep going, there’s no shame in asking for help when you need it. In fact, it’s one of the smartest things you can do.

Having said that, doola is right here to make sure you don’t have to tackle these business challenges alone. We’re here to help make your entrepreneurial journey smoother, especially when it comes to the parts that feel overwhelming — like bookkeeping.

We’ve got your back, no matter how complicated things seem right now. So why not take the first step today?

Book a free demo with our bookkeeping experts.

Bring all your questions — big or small — and we’ll guide you through it with real, human support. Let’s make this part of your business easier, together.