Tools For The Self-Employed (Independent Contractor, Small Business Owner, Freelancer, Gig Worker)

Being self-employed is rough, but extremely rewarding for those who keep pushing forward. It’s especially rough for gig workers that can’t seem to get out of the employee mindset and into the business mindset, but that’s another topic. In this post were going to look at some tools that can help make your life easier. This post may be updated with additional tools and information overtime.


A popular app used, especially among gig workers, is Stride Tax. Even I started out with it. It’s a great app for beginners, particularly those who’ve never needed to track mileage or other deductions. Stride Tax is a great way to get started into bookkeeping and accounting. But if you’re full-time self-employed, I’d choose a more robust service then Stride Tax. Another popular one is QuickBooks Self-Employed, which I’ve also tested myself (mainly because I got a year free to try it). But there is still a better option.

I‘ve recently started using Hurdlr. It’s a great app and highly recommended. The free version is much more robust then Stride Tax and is very similar to QuickBooks Self-Employed; except unlike QuickBooks, it’s free. They also have two paid versions, Premium ($5/mo billed annually or $8/mo billed monthly) and Pro ($10/mo billed annually). The free version is sufficient for most gig workers. But other independent contractors and small businesses would do great with the Premium version (the version I use). Premium is lower cost then QuickBooks Self-Employed and offers more features. The Pro version has a few extra features some may enjoy, but I don’t feel most need those extra features unless they really want them. All three versions also provide more reports then you’ll probably need to utilize for taxes, but can utilize them to get a complete picture of your businesses finances.

With the Premium, you can automate tracking of:

  • Mileage (personal, business; and to which business/client)
  • Earnings (and to which client earnings are from)
  • Expenses (and to which business/client expenses are for)
  • Time

The Free version offers the same breakdown, but only semi-automatic. Some are preloaded into app, but you can add your own under “Businesses” in the main menu by pressing the plus symbol.

Here’s what my business/client list looks like:

My gigs and business are listed. Income and expenses from each are automatically linked to each, making filing taxes much easier then the limitations of the Stride Tax app.

Earnings and expenses are tracked by connecting your bank account(s) to the app. I absolutely love this because rather than only having a tracked total income from all sources (Stride Tax) and then having to manually do the breakdown for taxes, Hurdlr does this automatically. It also lets you view your earnings to expenses, earnings before and after estimated taxes, on an annual, quarterly, monthly, and all time breakdown. You always know what you earned and through which business and/or client, and you always know what your estimated taxes will be.

Hurdlr also has a giant list of categories for expenses and deductions, with many breaking down further into sub-categories. Hurdlr also has you put in your tax info, similar to filling out a W-4 for a job, so you know the exact amount of estimated owed taxes. This is much more helpful then the limit of options available in Stride Tax, and their “one size fits all” 30% self-employment tax calculation.

Whereas Hurdlr is a complete bookkeeping service, which may be a bit to learn for someone new to being self-employed, I truly think it’s worth it. Utilize the free version to learn your way around, keep it free if you’re self-employment is part-time and upgrade to premium if you go full-time. For those who have been self-employed a while and are looking for better services, give Hurdlr a shot. It’s well worth it, no matter the industry you’re in. And don’t forget, the paid plans are a tax deduction!

Click Here to give Hurdlr a chance.

In addition to Hurdlr, I also use WorkSolo for my gigs. If you’re a gig driver, they track mileage and earnings for each linked gig account. Once your area has enough users of the Solo app, they even offer a pay guarantee. To check it out, click here.

Email & Website

When you have your own business, it’s wise to have your own email on your own domain. It simply looks more professional and gives you more credibility. Despite this, I still see too many using free email such as or Stop doing that. Your own email on your own domain, aside from giving you more credibility and the appearance of professionalism, is a minimal expense and a tax deduction.

I own domains registered through GoDaddy and (yes, you can point WordPress registered domains anywhere; just like any other registrar). My email packages for two of my domains, one from each registrar, I used their partnered program. In GoDaddys case, my email is through Outlook; in WordPress.coms case, my email is through Google WorkSpace. There may be more features available had I gone direct, rather than through a reseller, but it’s easier (for me) to keep everything together. I purchased my recent domains through because they were offered there cheaper (upon renewal) than GoDaddy and NameCheap.

My GoDaddy email serves its purpose. That particular domain email will only ever have my email. I won’t need any extra features or options. But it wasn’t until I got my Google WorkSpace email setup, for the same cost I’m paying GoDaddy for Outlook, that I realized just how many features I’m missing. With Google WorkSpace you can:

  • Create aliases to receive and send emails
  • Create group mailing lists to receive and send emails
  • Limit what staff can access
  • Limit what staff can use their company email to sign up for
  • Block logins from compromised or “rooted”/”jailbroken” devices
  • Block or limit what data can be saved or backed up to other devices, including USB ports
  • Remote wipe data from staff no longer in your company
  • And so much more

Having all this functionality is absolutely amazing. It may feel overboard if your a solopreneur, but will come in handy as you expand if you decide to do so. Even small businesses with small teams, allowing your staff to have a company email and help with support issues via emails (group emailing lists) could help free up more of your time, all the while helping your team feel more a part of an actual team or “family”; and in turn, not be so quick to look elsewhere for another job. They even prove to be a valuable asset helping you grow by providing them this little bit of extra responsibility.

I highly recommend looking into Google WorkSpace for your email needs. By default, it also connects to other Google services, such as Drive and Docs, to make information sharing across your team that much easier. And you can login through the native GMail app on your phone. All this for the same price as my extremely limited email through Outlook ($6/mo).

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If you don’t already have a website, now that you have a domain for professional emails, consider using it to build a website. No matter how small your business is, websites are crucial real estate today. It allows customers to find you online, not just your competitors. There are tons of website hosting options from shared hosting and self-hosted. Shared hosting platforms will come with various plans that offer different features. At the very least, you want the lowest plan that affords your custom domain (not a address). Like your email, you want your site to look professional and like you mean business. Shared hosting wise, I recommend You’ll have an option of four different paid plans to choose from, each plan up gives you more features. The Business and eCommerce plan will allow you to remove all branding from your site as well. Though for most small businesses, the Premium plan is sufficient.

Many may suggest self-hosted is the way to go. When your business is large enough, it may be. But getting started, I see no issue with shared hosting. Especially with SSL certificates, privacy protection, etc are all included and handled by them. This not only helps save money, but gives you peace of mind. They’re going to keep security up-to-date because they’re protecting their platform, which would include your site, against hacks and other attacks. Which I find to be a major advantage over self-hosted, where you need to monitor and update yourself, getting started. You can always migrate to self-hosted when your business is large enough and you can afford to hire staff to take care of your website for you.

If you decide to use to build your website and/or register domains, use my link to get $25 credit towards your purchase. paid plans remove ads, will use your custom domain (the won’t show in the address bar) and are affordable. I’m using the Premium plan on one of my websites (my primary business) and will be upgrading to the Business plan. The Business and eCommerce plans offer the most customization and flexibility with your site, and saves you the cost of having your own server; and may be more affordable then other shared hosting platforms for sites. If you have a site, your theme and plugins are able to migrate/transfer to, but you will need a Business or eCommerce plan to keep your customizations and plugins. Consider giving a shot for great, affordable web hosting and domain registration by clicking here.


Being self-employed also means we need to pay our own insurances and other coverages. Many don’t know where to look or realize it’s even available. Those who were never self-employed don’t seem to realize we can get benefits for ourselves, and sometimes even cheaper then utilizing employer coverage (yes employees, you are paying for your employers coverage before you even see your paycheck). Here are a few places you can find benefits as a self-employed independent contractor, gig worker, freelancer, or small business owner. Some plans are even flexible enough to grow with the solopreneur as you decide to expand and hire others.

For tax withholding, retirement, and health insurance, check out Catch Benefits. They are designed specifically for independent contractors. 

As well as providing tracking of tax deductions and mileage (albeit limited, as stated above), Stride also offers insurance plans (medical, dental, vision).

As a self-employed independent contractor, you are responsible for your own workers compensation insurance, should you feel the need for it or if it’s required of your industry or area. Either way, required in your area / industry or not, having a workers compensation policy on yourself in the event you should become injured during a job is a good idea. There are services who provide workers compensation policies for independent contractors. Two services you could obtain a policy through are:

Gas Savings

Some industries require a lot of driving. Whereas the mileage deduction is a help, it’s always nice to save extra money on gas, right? Here’s how you can save on gas; savings are cashback on verified offers at qualifying gas stations.

Save 15¢ ($0.15) OFF Gas with the GetUpside app. Use code RED6738 when creating your account.

You should also sign up for GasBuddy (yes, you can double dip). I’m giving you $5 in free gas on your first fill-up! Just sign up for the FREE GasBuddy card to start saving on every gallon. Use code WGV9MYF.

To double dip, order the GasBuddy card. When it arrives, activate it and add it to your GetUpside account (in the ‘My Wallet’ section). Then claim offer/deal in both apps and use your GasBuddy card to pay for the gas. Important to note that the GasBuddy card will only work at the pump, not inside at the register.

Between both of these services, you should be able to save a good bit on gas. Before you fill up, remember to open the apps and claim the offer for the gas station you’re at. After fill up, upload the receipt to the apps. You’ll get your savings as cash back after the offer is processed.

Phone Service(s)

For phone service I recommend T-Mobile. They offer great unlimited plans using 4G and 5G networks. I find I have better coverage then with AT&T or Verizon. Whether you go personal plan with business use deductions or go straight for a business plan to keep it separate from your personal life, it’s a top notch service to have. I live in a rural area and experience no dead spots. I get signal even out on the water and in the national forest. T-Mobile service is truly unbeatable. They’re the first to create a plan with Premium Data! What this means is that on unlimited plans, you won’t get throttled after so much usage. No matter how much data you use, it remains high speed. The Premium Data Unlimited Plan prioritizes you over other users. You can also setup a T-Mobile Money account, which is an online bank account. Use it as a primary bank, or move funds into it just to cover the phone bill each month with auto-pay (what I do). Click this link to check out all that T-Mobile has to offer.

More To Come

Over time more tools and additional information may be added to this post. Being self-employed should be fun, and can be. There’s no reason why it should cost more than it needs to. We have enough to worry about with our businesses and/or gigs and our bad days. No need to keep stressing losing money. Consider the tools and services suggested in this post, and check back now and again for additional tools and services that may be added.

Know of a tool or service that should be listed here? Leave a comment below or email

Disclaimer: Some links in this post are affiliate or referral links. Clicks on said links are tracked and I may receive compensation upon your account creation and paid upgrade.

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