In 2022, I joined the great resignation and left my full-time job to pursue working for myself as both a writer and a carpenter. While I had been freelancing in some capacity for nearly a decade, I never fully stepped out of the traditional job world — primarily out of fear that I’d be too stressed having to handle everything myself. (It turns out, I’m much less stressed now!)
I wasn’t the only one out to make the jump. As the self-employed workforce grows, there’s a demand for more tools and resources to help us thrive.
Keeper, a tax app, is one such tool, and it has made it possible for me to have a stress-free tax season. It’s also helped educate me on what write-offs I’m entitled to, whether I’m doing a one-time side gig or signing a year-long contract.
Here’s why I’ve decided that Keeper is the best independent contractor app out there.
Why you should use Keeper
Whether you’re a first-time freelancer or an experienced contractor looking to streamline your day-to-day responsibilities, Keeper is an invaluable tool.
With comprehensive expense tracking, regular updates, and expert tax assistance, it’s allowed me to spend less time on my finances. In turn, that’s given me the mental space to focus on refining my skills and the confidence to work on bigger, more involved projects.
Here’s what I’ve gotten out of Keeper.
1. Thousands in tax savings
The average Keeper user saves $1,249 on their taxes. Halfway through the year, I’ve already accumulated almost $2,000 in expected savings thanks to Keeper's meticulous tracking and helpful reminders.
Since I‘ve been using Keeper for over a year now, I have a sense of what I can save — which has helped me feel more comfortable investing in my freelance business.
2. A personalized tax experience
You link the credit card and bank accounts you use for work to the Keeper app, which uses them to help you find deductible business expenses.
In my review of how Keeper tracks receipts for taxes, I mentioned how the app flags each purchase I make and asks whether it was for work. This makes it easy to separate my business expenses from my personal spending. The app even learns my habits over time — more on that later!
That was when I first started getting long-term freelancer projects. At the time, I used my personal checking account for everything. As a result, my job-related expenses were getting lost in a sea of iced coffees and personal bills. In time, I opened a separate business account for work-related payments and linked that to my Keeper profile. From there, I knew exactly what I could and couldn’t write off.
Linking my accounts to Keeper meant I was no longer scanning my billing statements each week to stay on top of my expenses. That freed up a lot of mental space for finding new clients.
And for those worried about sharing sensitive information, Keeper uses SSL 256-bit encryption to protect your banking details and does not store your data.
3. Easy expense tracking
Keeper makes it simple to mark whether something you bought was a business expense, which is useful at tax time.
While I touched on this above, it’s worth giving the expense tracking feature extra attention because it’s truly a game changer. In particular, I love the regular reminders about my write-offs.
These quickly gave me a sense of how I was spending my money. Some of the positives that came out of really understanding my cash flow were:
- Knowing how much spent on projects so I could create more detailed estimates — which provided more transparency for clients and ensured I was profiting
- Having insight into unexpected job expenses (such as extra hardware), allowing me to budget accordingly. One of the biggest challenges I faced before Keeper was getting hit with a change order or realizing that a job would take longer than expected and would lose me money at the end of the day
- Better understanding what I could afford to offer as an independent contractor
For example, if a client asked me to build a kitchen island, I would calculate the expenses and ensure I had enough in reserve for the materials —- or ask for a down payment for that specific job. Additionally, I’d be able to budget for extra tools and equipment. (While my Honda Fit does have a surprising amount of room, it definitely can’t fit a kitchen island!)
As a freelancer with two distinct professions, carpentry and writing, I quickly got a sense of my general overhead for each. After six months, I was wondering how I survived (not to be dramatic!) without Keeper to track my expenses.
4. Tax help at your fingertips
Keeper gives you access to live tax assistance that’s basically as easy as texting. It's one of the app's more unique features.
When I started using Keeper, I didn’t pay much attention to the “Tax Help” feature. It’s not that I didn’t think I needed help — I definitely did! But so many apps have automated assistance that I’ve never found particularly useful. I thought this would be more of the same.
It turns out, it’s not just an automated feature —- a real-live person answers questions when you need them to.
In the “Tax Help” section of the app, you’ll encounter a combination of AI and human-centric design. You’ll get some automated messages about purchases, deadlines, and so on, but you can also send your questions here. They’ll answer any question about taxes you can think of.
My Keeper tax assistant will typically responds to my messages same day.
Being able to chat with someone is especially beneficial when it comes time to file your taxes (which I’ll cover later). Freelancers always have to be aware of changes made by the IRS, such as the tax forms you’ll be receiving. With so many moving parts, staying on top of your tax obligations can be challenging. So I rely on my tax assistant to track exactly what I need to do for my taxes.
In addition to providing important information about tax law, your tax assistant is also there to help you navigate the app and customize it to your specific needs. For example, I asked mine to help me make it so that a certain recurring transaction was always treated as a write-off.
5. Automated write-off detection
Your tax assistant will automatically reach out once a week to ask you to confirm certain write-offs. They’ll also email you a summary of your weekly write-offs so you can see how much you’ve saved. But the app itself can also find a lot of your write-offs without you having to do anything.
The app can help you find write-offs by:
- Learning from your spending habits and what expenses you always mark as a write-off
- Helping you create “rules” that will automatically flag certain transactions as tax-deductible (such as your cell phone bill, car-related expenses if you drive for work, and so on)
- Marking purchases that are less common to ask you whether they’re work-related
99% of the time, these features help me stay on track. But if I ever lose track of an expense, I can use the app to check what’s happening on my banking account instead of going straight to my banking app, which also includes personal purchases and can get confusing.
6. Categories for your business expenses
If you’re a jack of all trades like me (variety is the spice of life!), then being able to categorize your expenses is essential. Keeper makes it super easy for me to review transactions directly on the app and categorize which ones were for writing projects versus carpentry-related jobs.
For example, in the summer of 2023, I took on a six-week carpentry job while regularly writing copy for a long-term client. Each week, I’d check my gas expenses, which I knew were related to my carpentry job, and adjust my weekly invoices accordingly.
Because Keeper allowed me to see how much I was spending, I was able to make enough profit to buy materials for upcoming smaller projects for the first time since I transitioned to full-time freelancing.
7. Integrated tax filing
Keeper collects write-offs that you’ve logged through the app, giving you the option to export them for your accountant or use them to file taxes right in the app.
If you’re a subscriber, tax filing is included in your membership. Once you're done filing, your return is saved directly in the app and can be referenced at any time.
Navigating tax filing
The tax filing interface is super easy to navigate. You’ll fill out basic information, like your household details and personal information. The categories are clearly marked, including:
- Credits and deductions
- States taxes
Under “Income” Keeper, provides a comprehensive list of potential revenue sources, including W-2 if you are a freelancer who also works a day job.
AI filing assistance
The tax filing experience also comes with an AI assistant for quick tax questions. I found this useful as someone who has one more cut-and-dry profession when it comes to tax write-offs — copywriting — and one that walks the line of being considered art. (When I make furniture and it sells, that’s considered selling artwork!) So I used the AI assistant to confirm exactly what write-offs I’m entitled to as an artist.
Finding tax breaks
For credits and deductions, the app includes the business write-offs it’s already tracked for you, as well as health insurance (which is awesome, because that one really adds up when you’re paying on your own!). That’s in addition to basic categories like loans and tuition.
One thing I really appreciate about Keeper's tax filing experience (and there are many!): you can do it on the mobile app, but you aren’t forced to. If you're more comfortable filing on your computer, just go to Keeper’s website and log in with your phone number. From there you can continue where you left off on the app!
8. Export your write-offs directly from the app
After marking and categorizing your business expenses throughout the year, you can export them into a spreadsheet for tax time — useful if you need to give it to an accountant.
Since Keeper offers a delightful mix of autonomy and automated help, I was able to track my expenses as I built up a solid client roster. When it came time to file taxes, I exported everything I’d categorized as a write-off. Not only does the spreadsheet include total amounts, it also provides line items for each expense.
9. Transparent, affordable pricing
Keeper comes with a free trial. After that, it’s $192 for the annual subscription, which gets you an expense tracker and a tax software, plus access to tax experts. If you’re not ready to commit for a year, the monthly price is just $20.
Of course, you can absolutely write off Keeper! Anything that makes it easier to do your job is an investment and, in this case, also a tax deduction.
5 reasons I love Keeper
Now that we’ve gone over the central features of the Keeper app, let’s go through some of my more subjective impressions of the app. It’s all part of deciding whether Keeper is right for you.
Here are the top 5 features I love about Keeper — plus some thoughts from a fellow freelancer who uses it.
Reason #1: An eye for detail
Okay, I know, Keeper’s an app, not a person. But because it so meticulously tracks finances, you feel it’s watching out for potential savings like an accountant would.
I’ve learned a lot about what I can write off, such as dinners and travel, that I previously wouldn’t have considered work-related. As I’ve read through the “Tax University” segment of the app, I’ve become much more confident about making sure I’m deducting anything that’s an investment in my business — even if I’m doing something that’s objectively fun as well as productive, like a business meeting at a nice restaurant.
Similarly, Maria Uranga, an independent driver who uses Keeper, has been able to deduct more expenses, since the “write-offs are so detailed and the app tracks everything.”
Reason #2: Speed of learning
Because Keeper uses AI to streamline the user experience, the app quickly picks up your patterns, such as repeat purchases.
Early on in my experience using Keeper, the app worked alongside me as I identified what I paid for to succeed as a freelancer. It highlighted my potential write-offs while I got a sense of my everyday spending habits.
Reason #3: Frequent (non-annoying) reminders
We all know how disruptive it is to receive emails every second of the day after making a purchase. I was initially worried that Keeper’s updates would be too much. Instead, I came to welcome them because they’re actually informative.
Most of the time, I quickly review these emails just out of interest. Occasionally, though, I catch a write-off I may have missed. From there, I can easily adjust and save even more!
Reason #4: A one-stop freelance shop
I used to be wary of apps that claimed they could do everything from soup to nuts. But since Keeper uses AI to organize write-offs while also acting as a conduit to professional tax services, I feel comfortable knowing that I can always get tax help, whether I’m actually filing taxes or just deciding whether or not something is a write-off.
Reason #5: Control over your finances
Getting weekly updates on potential write-offs gives you a sense of where your money is going and whether you need to tighten your budget (or raise your rates!).
For example, I found that I needed to charge more for carpentry gigs, because my rates stayed the same even as the price of materials skyrocketed. I didn’t catch that until Keeper made it possible to visualize my weekly spending.
How does the competition hold up?
Keeper stands out because it’s an app designed specifically for freelancers of all kinds, from W-2 workers with a side hustle to full-fledged small business owners. Additionally, it works as an educational tool, providing both live tax assistance and a wealth of knowledge through its “Tax University” series.
Compared to your other options, it’s the best app for combining tax filing and expense tracking for independent contractors.
TurboTax was one of the first digital tax filing apps online. It’s adjusted its platform to include filing for self-employed workers, though they’ll have to track expenses elsewhere.
TurboTax could be a good choice for small business owners, but the platform isn’t the most supportive of gig workers and side hustlers, who are forced to pay for pricey upgrades even if most of their income comes from traditional employment.
Pricing comes in at $119 for federal and an additional $49 for state filing. But independent contractors must upgrade to the Premium product if they want any tax assistance.
How does Keeper compare?
In comparison, Keeper has expense tracking and tax help built into its transparent pricing, plus no additional cost to file in multiple states.
Another known name, QuickBooks Self-Employed has been in the accounting game for a while now. It has a self-employed product for small business owners and independent contractors to track expenses.
The lowest tier is $10 a month, which is reasonable, and it includes a mileage tracker — something that comes in pretty handy, especially if you drive a lot for work. It also promises to maximize Schedule C deductions. Yet, when it comes to filing, users have to upgrade to the second or third tier, which is $15 or $20 a month, only to file through TurboTax.
How does Keeper compare?
Keeper’s advantage is being able to file directly through the app without paying extra. Plus, you get can access tax professionals.
Expensify is designed mainly for small business owners and provides financial planning, bookkeeping, and budgeting tools.
While you can use Expensify as an independent contractor, its strong point is financial management. It doesn’t cater to the specific needs of freelancers, who often have simpler businesses without employees and something that’s more financially lightweight. (And let’s be honest, we need an app for us!).
In addition, when it comes to pricing, Expensify plans are complex, and there’s an incentive to use an Expensify card to get a discount on the price. The free plan, which is geared toward self-employed people, is more limited and focuses primarily on expense tracking.
How does Keeper compare?
In contrast, Keeper comes with tax filing bundled in. With access to a tax assistant, it also adapts to your needs when tracking expenses — not the other way around.
As my busy season winds down and my projects come to an end, I’ll rely on Keeper to stay on top of my expenses while I continue building my portfolio. It’s been a joy using the app this last year. I feel confident knowing that, even in the ebb, it’ll serve me well as my freelance career continues to grow.
Over 1M freelancers trust Keeper with their taxes
Over 1M freelancers trust Keeper with their taxes
Over 1M freelancers trust Keeper with their taxes
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At Keeper, we’re on a mission to help people overcome the complexity of taxes. We’ve provided this information for educational purposes, and it does not constitute tax, legal, or accounting advice. If you would like a tax expert to clarify it for you, feel free to sign up for Keeper. You may also email firstname.lastname@example.org with your questions.