Recently, I had a conversation with a friend who runs an animal shelter, and let me tell you — her bookkeeping struggles sounded all too familiar. Like many solopreneurs, she’s juggling everything with a tight budget. Her shelter relies entirely on in-kind donations, so hiring a full-time bookkeeper or splurging on a fancy accounting software isn’t an option. 

That means she is responsible for keeping track of every single donation, sending tax exemption receipts, and now, with their new FCRA registration, managing foreign contributions as well.

Talk about pressure, right?

She did get some part-time help from a bookkeeping advisor last month, but even with that, her plate is still full. I remember her telling me how, one day, she was buried under a mountain of receipts, trying to keep up with everything, and it just became too much — she literally fell asleep from the exhaustion. 🥺

Now, she’s been digging into DIY bookkeeping tips to ease the load.

And I’m sure you’ve been there too, or maybe you’re dealing with it right now — swamped with invoices, receipts, and financial reports, wondering how to keep your sanity intact. This isn’t just an NGO problem; it’s a challenge every solopreneur faces. Even our CEO, Arjun Mahadevan, hears about these struggles from entrepreneurs all the time.

So, based on these insights and from our conversations with teams who deal with these exact bookkeeping issues, I’ve put together this guide to help you manage your bookkeeping like a pro — without losing your mind in the process.

The Real Bookkeeping Struggles of Solopreneurs

When you’re running a one-person show, the to-do list never ends. Let’s dig into a few bookkeeping challenges you might be facing and how to overcome them.

1. The Time Problem

Raise your hand if you’ve said, “I’ll get to the bookkeeping later.” Yeah, later can quickly turn into next month or even next quarter. Solopreneurs are juggling so many things that spending a few hours tracking expenses just feels like something you can back-burner (you can’t, but we’ll get to that).

For example, let’s say you’re a freelance graphic designer. You’ve got deadlines, client meetings, and brainstorming sessions that take up most of your day. That little folder of receipts just sits there, growing bigger.

By the time you actually sit down to reconcile it, you’ve forgotten half of what those expenses even were.

2. Inconsistent Income

One of the hardest parts of managing finances as a solopreneur is dealing with inconsistent cash flow. There are feast-and-famine months where you can go from big client payments rolling in one month to crickets the next. This makes managing your books and planning for expenses feel like a big jigsaw puzzle. 

Keeping track of your fluctuating income and trying to create any sense of financial predictability can be a big challenge.

Without proper tracking, you won’t know when to pull back on spending or when it’s safe to splurge a little on that new accounting software. 

3. Overwhelm and Chaos Around Taxes

Here’s a common confession we hear from entrepreneurs and solopreneurs: They panic a little when they hear the word “taxes.” Even when you’re doing everything right, it’s hard not to worry about messing up something and inviting the fury of the IRS.

Plus, when you’re managing invoices, expenses, and receipts on your own, tax season feels like this huge, merciless wave that’s coming for you. 

Without a good plan, you might end up scrambling at the last minute, trying to dig through those meal receipts from client meetings or home office deductions. You know what we mean?

4. The “Who Do I Ask for Help?” Problem

Let’s admit it — this is where things start to feel lonely. You’re doing all the things, and when you hit a roadblock in bookkeeping, there’s no one to lean on. No finance team, no accounting department — it’s just you and that blinking cursor on Google. 

And the worst part? 

The more you try to figure it out on your own, the more confusing it gets. You think about hiring help, but then you remember you’re a solopreneur, and bookkeeping services are not cheap.

It’s frustrating, and sometimes it feels like asking for help isn’t even an option. 

But hang in there, because in the next section, we’ve got some tips to help you navigate this situation without draining your budget.

 Ready? Let’s jump right in.

6 Super Simple (But Effective) Solopreneur Bookkeeping Tips

So how do you handle all this without completely losing your mind? Trust us, you don’t need to be a financial genius to keep your books in order — just follow these bookkeeping steps in doola’s way.

1. Separate Your Business and Personal Finances (Yes, Right Now)

One of the most common and easy mistakes solopreneurs make is mixing their personal and business finances. It’s understandable — you’re out running errands, pick up some office supplies, and use your personal debit card because, well, it’s just convenient. 

But here’s the problem: when tax season rolls around, that convenience becomes a headache. 

Sorting through a tangled mess of personal and business transactions is not only time-consuming but also risky. It’s harder to prove what was a business expense versus a personal one when it’s all in the same account.

Plus, you could miss out on deductions that would save you money or even flag issues with the IRS.

What should you do then?

Well, open a dedicated business bank account, even if you’re just starting out. Many online banks offer no-fee options with easy setups, so there’s really no reason not to. Make sure to use this account for all business-related purchases, even the small ones. It’ll save you time, stress, and potential tax issues down the line.

2. Get Into the Habit of Weekly Check-ins

You don’t need to spend hours every week working on your books, but a consistent 30-minute session is your magic mantra to solve your bookkeeping mess. Switch off your phone, close all the tabs on your laptop and sit somewhere where there’s absolutely no distraction.

This small habit prevents your expenses from piling up and avoids that sinking feeling of “where did all my money go?”

This is what doola recommends: 

Block out time for a “money date.” Treat it like an appointment with yourself. Pick a day (Friday afternoons? Monday mornings?) You call. And put it on your calendar. When it’s time, turn off your phone — no notifications allowed — and close all those browser tabs on your laptop.

The goal is to be fully present and focused. Use this quiet time to review transactions, pay invoices, and organize receipts. That bit of consistency will save you hours of stress later.

3. Use a Dedicated Bookkeeping Service like doola

A dedicated bookkeeping service is one of the best ways to get your bookkeeping done without stressing about it. doola’s dedicated bookkeeping service is the perfect way to say goodbye to the complications of managing your finances, and let the experts take over instead!

4. Track Every Little Expense

It’s tempting to skip over the small stuff — like that $10 you spent on coffee during a client meeting. But all those small expenses add up, and they’re tax-deductible, too. You might not notice now, but come tax time, you’ll be glad you captured those seemingly minor costs.

For example, let’s say you’re running a social media consulting business. You’re meeting clients at cafés, paying for Instagram ads, and buying that fancy new design software to keep your services top-notch. It’s easy for those expenses to creep up on you.

If you’re not tracking everything, you might not realize how much you’re actually spending to keep things running smoothly. And worse, you could miss out on valuable deductions that could save you big during tax filing months.

Try using an app like Expensify. Snap, log, and you’re done—no more lost receipts at the bottom of your bag or panicked scrambling at the end of the month. Plus, Expensify automatically categorizes your expenses, so you can see exactly where your money is going. 

5. Prepare for Taxes Throughout the Year

The worst thing you can do is wait until April to start thinking about taxes. As a solopreneur, taxes are your responsibility, so you need to plan ahead. A good rule of thumb is to set aside 25-30% of your income for taxes. This way, you won’t be caught off guard by a big bill.

Let’s say you’re a freelance photographer who gets paid sporadically — sometimes you book a big wedding, and other months are slow. By automatically funneling a percentage of each payment into a tax savings account, you’ll have enough saved when tax season comes.

And if your income is irregular, consider making quarterly estimated tax payments to avoid a huge hit at the end of the year.

6. Leverage Cash Flow Management Tools

Solopreneurs often struggle with cash flow, especially when income fluctuates. To avoid running into trouble, use a tool like Float to forecast your cash flow. It helps you predict when you’ll need to pull back on expenses or when you can invest more in your business.

Pro Move: Set up alerts in your cash flow tool to notify you when cash is running low. This helps you stay on top of things before you’re in panic mode.

Related Reading: How to Start a Freelancing Business in 7 Steps

When to Get Help (and How to Do It on a Budget)

Okay, so you’ve nailed the basics. You’re tracking every expense, sticking to those weekly check-ins, and keeping your business and personal finances separate — nice work! 

But here’s the thing with bookkeeping: even when you’ve got it all together, there’s bound to be a moment when things get a little tricky.

Maybe a tax situation pops up that makes you pause, or you hit a financial roadblock that feels way out of your depth.

So, what do you do when that happens? How do you get help without losing your mind (or your budget)?

Here’s a straightforward guide to finding the support you need, even when funds are tight.

1. Look for Freelancers

Freelance bookkeepers can be a cost-effective solution when you need a little extra help. They’re often more affordable than hiring a full-time accountant, and you can pay them by the hour or per project.

Where to Start? Well, Websites like Upwork and Fiverr are full of freelance bookkeepers who specialize in helping solopreneurs. Look for someone with experience in your industry, read reviews, and reach out for a free consultation before you commit.

2. Bookkeeping Advisors Can Teach You the Ropes

Instead of hiring a full-time bookkeeper, you might just need someone to show you how to manage your books properly. A bookkeeping advisor will help you create a system that works for your business. They’ll set up tools like invoicing templates, organize your expense tracking, and give you a roadmap for what to track.

Once you’re set up, you’re more equipped to handle the books yourself, saving you from paying for ongoing services.

doola’s bookkeeping advisors can also help you get the most out of your tax deductions. They’ll point out what you can write off, like home office expenses or business travel, which can save you a significant amount at tax time.

3. Hire Help Only for What You Really Need

You don’t have to hand over all your finances to a bookkeeper or accountant. If you’re trying to keep costs down, focus on the areas where you need help the most. Maybe you feel confident with day-to-day expense tracking but need someone to handle taxes or give you advice on quarterly payments.

For example, let’s say you’re a solopreneur running an online clothing store. You’re pretty good at tracking sales and expenses but need help calculating sales tax or figuring out how to categorize certain expenses.

Instead of hiring a full-service bookkeeper, find someone who specializes in tax laws or sales tax compliance. You can hire them for that specific need without paying for more than you require.

4. Tap Into Free Online Resources

The internet is loaded with webinars, blogs, and YouTube channels that can guide you through the tricky bookkeeping parts. You’ll find everything from invoicing tips to smart ways to track expenses.

We also have a podcast where other solopreneurs share their experiences and insights. You can learn directly from people who’ve been in your shoes. All of this  info can help you feel more confident in managing your books.

A must-read: The Lifestyle of a Successful Entrepreneur: 17 Winning Habits

Mastering Your Finances Without the Stress With doola

Being a solopreneur already comes with enough challenges, and stressing over every single number in your books shouldn’t be one of them. But, you don’t have to be a financial wizard to simplify bookkeeping. 

Just start small. Separate your personal and business finances. Do those quick weekly check-ins (it doesn’t have to take hours), and take advantage of the free tools available to make bookkeeping way less painful.

And when you hit a roadblock  there’s no need to panic. Whether you’re running on a shoestring budget or not, there are affordable ways to get the help you need — without draining your bank account.

Remember,  you’re not the only one juggling receipts and wondering if you missed something. Every solopreneur goes through this. The difference is you’re taking action, and that’s important.

With a little consistency and doola’s help you can take control of your finances and keep moving toward your big goals.

So, go ahead — take that first step. And if your next money date includes a little treat, like chocolate or your favorite coffee? That’s just you rewarding yourself for staying on top of things.

Need a little more support to make bookkeeping even easier? Book a free consultation with doola, and let’s make sure your finances are as smooth as your next win.