#painless1099

[painless1099]

What Does Misclassification Mean (For Me)?

Self-employment is great, sure, but am I actually self-employed?

Unfortunately, the answer for a lot of people doing contract work is – no. Truth is, there is a fine line between being an employee of a company (being classified as a W2 worker) and doing work as a contractor for a company (being classified as a 1099 worker). Sadly, employers will often take advantage of what-should-be employees by classifying them as contractors.  This allows them to avoid providing these individuals with the benefits they would be entitled to as an employee while depriving them of the luxuries they could expect as a contractor (1099er).

How do I know if I’m being correctly classified?

According to the IRS, there are 3 rules to consider when trying to determine if you are an employee or a contractor. These three rules are:

Behavioral: Basically, this asks who is in control of your work. Does the company tell you what to do and when/where to do it or you do have the freedom to choose?

Financial: This rule asks who is in control of the resources that are necessary to the one doing the work. Are they providing tools or supplies that are necessary for you to get your work done? Is the employer reimbursing you on expenses that are necessary for you to complete the job (i.e. a gas expense)?

Nature of Relationship: How does your employer handle your relationship? Will the relationship between you and the employer continue after you’ve completed the agreed upon tasks? Are the tasks that you are performing key functions of the business? Lastly, is the employer providing benefits such as; a pension plan, vacation pay, or insurance, or not?

It’s important to consider these three rules when determining if you are classified correctly. If it seems as if your employer has full control over how you do your work, but isn’t providing you with the benefits of being an employee, there is a chance you are misclassified. If your employer continues to pass you projects beyond the scope of the initial work you agreed to do, again, there’s a chance that you’re misclassified.

Why does it even matter?

By being misclassified, you’re essentially being sold short to your employer’s gain. Employers deprive you from the autonomy that comes with being self-employed, while not providing the benefits that come with being an employee. It’s best to understand classification to ensure that you aren’t getting the short-end of the stick and can truly enjoy the lifestyle of being self-employed. Keep in mind though, while self-employment comes with a newfound sense of freedom, it also comes with a lot of new responsibilities.

Responsibilities..? Like what?

Well, for instance, when you are an employee you don’t have to think too much about benefits and likely take them for granted because your employer handles them on your behalf (for the most part). Benefits such as; tax withholding, healthcare, retirement, and unemployment are typically all facilitated through a benefits package from your employer. This means, when it’s time to pay taxes, your employer has already withheld tax money from your income to cover your taxes. Or when you’re feeling under the weather, you can confidently see a doctor without worrying about paying completely out-of-pocket. However, when you’re self-employed, it’s 100% your responsibility to ensure that you have these pieces covered. It’s definitely in your best interest to put the appropriate pieces in place to prepare for both the expected (taxes) and the unexpected (health crisis.)

Are there tools that can help?

Sure! There are products being created to make benefits for self-employed folks a little more manageable. Tools such as Stride Health for healthcare and Betterment for retirement planning are super helpful in making sure that you’ve got your benefits covered.

If you’re like the 70% of Americans who struggle with saving money, manually setting cash aside from each paycheck is a real pain. However, so is not having money to cover the costs of the benefits mentioned before, trust us. Painless1099 will automatically set cash aside from each paycheck, ensuring that you’re saving as you earn so that you don’t end up in a pickle.

I think I’m misclassified, what do I do?

If you’re feeling unsure about your classification, it’s always good practice to investigate and receive clarification from your employer. Do some homework, consider the situation and have a conversation with HR (if the company has a HR department) or go directly to the individual who contracted you to do the work.

Once you’re confident that you’re being correctly classified, be sure to equip yourself with proper tools, like Painless1099, to make self-employment feel like a traditional job, at least when it comes to your benefits.

[cesarhcastrojr]

Paying Uncle Sam after tax day in April sounds crazy, right? Well, that’s the ugly truth for freelancers, Airbnb hosts, rideshare drivers, or anyone else who gets a 1099 at the end of the year. If you’re self-employed, you have four tax days a year. These are otherwise known as quarterly estimated tax payments. Confused? You’re not alone.

Over two-thirds of freelancers don’t understand their self-employment tax obligation. With your next payment just around the corner—in fact it’s this Thursday, June 15, to be exact—we put together a quick rundown to answer any questions you may have about paying your quarterlies.

Who has to pay?

Well, pretty much everybody. Here in the United States we use what’s called a “pay-as-you-go” system for collecting income tax. This means you’re expected to pay taxes on the income you earn throughout the year. This is something often overlooked when working a W-2 job because employers are required to automatically withhold money for taxes and pay the IRS on your behalf.

When you’re self-employed, there is no one there to withhold money for you or pay the IRS. It’s ALL on you to make sure Uncle Sam is getting his money. There are a few exceptions, but if you’re expecting to owe over $1,000 in self-employment taxes this year, you need to pay taxes quarterly.

Do I HAVE to pay them?

Neglecting to pay quarterly estimated taxes can get expensive. If you do miss a payment, you’ll be charged a penalty and have to pay interest on the unpaid balance of the missed payment. While missing one payment may not break the bank, missing multiple quarterly estimates can add up quickly. The last thing you want is to get to tax day only to be blindsided by a big bill from the IRS.

How much should I expect to pay? How do I get payments to the IRS?

There are a few ways to calculate how much you should pay and how to send the payments. The method you should use depends on a few things about your work.

If you earned 1099 income and paid self-employment taxes last year, you can base your quarterly payments off of the amount you paid last year. The IRS Form 1040-ES is the go-to resource for calculating what you need to set aside for this year’s payments. If your work is fairly steady, you can always refer to what you paid last year. Planning to pay 100 to 110 percent of what you did last year is good rule of thumb to avoid underpayment.

If this is the first year you’ve earned 1099 income, or if your work is seasonal, you can use what the IRS calls the annualized payment method. This simply means that you pay Uncle Sam a percentage of that particular quarter’s earnings instead of a flat rate for each quarter of the year. To use the annualized payment method, you’ll want to use IRS Form 2210. For more information on how to get your payments to the right place, check out these guides on paying federal and state quarterly taxes.

What if I overestimate or underestimate my payments?

No worries. The IRS will let you know. If you’re lucky enough to have made more money than what you estimated from the year prior, you’ll get a note from the IRS letting you know the amount you underpaid for the year. If you have an off year and overestimate your quarterly payments, you will receive a refund at the end of the year or you can just apply that amount to the next year’s tax obligation.

When are quarterly tax payments due?

Remember to mark these dates on your calendar to avoid having to pay those pesky IRS penalties:

1st payment..............April 18, 2017 2nd payment............June 15, 2017 3rd payment.............September 15, 2017 4th payment.............January 16, 2018*

*You do not have to make the payment due January 16, 2018 if you file your 2017 tax return by January 31, 2018, and pay the entire balance due with your return. How can I make handling quarterlies easier?

Having to pay the government four times a year sucks—there’s no way around it. However, there are a few really simple ways you can take the night sweats out of quarterly taxes. The key to getting your payments in on time is to make sure you’re keeping up with how much you owe each time you earn 1099 income. This probably sounds a little tedious so that’s why we created Painless1099.

Painless1099’s smart bank accounts automatically calculate and withhold the money you need to save for taxes every time you get paid and then send what’s safe for you to spend directly to your personal checking account. That way, you’ll always know your tax obligation is squared away and can focus on doing the work that got you into self-employment in the first place.

Nick Green is the Director of Business Development at Painless1099. Painless1099 automatically separates money for taxes every time you get paid by a client.

This is a post from Painless1099 – current sponsor of our SPARK program! Freelancers Union members get save 15% when you open an account with Painless1099. Learn more here.

[nofomoartworld]

Art F City: Set up For Your Best Year Aver: A Tax Day How-To

Here we are at Tax Day. Your taxes are filed. (They aren’t? Here’s an IRS extension form – postmark it today. You’ll need one for your state, too.)

Last year you vowed to get your stuff in order. Then suddenly the tax deadline was upon you, and you scrambled through the process, and weren’t as careful as you intended to be. You suspected you should have been paying estimated quarterly taxes all year, but didn’t, and now your tax bill is surprisingly high.

You meant to set some money aside in a retirement account, but that shocking tax bill meant you didn’t have any cash to do it.

You suspect that there were deductions you missed.

If you’re being honest, your books were a mess (if you’re thinking “I need to keep books?” go back and read this.)

Now that the time pressure is off, let’s take a look at how you can make this year better. Plus some discounts on apps that can help you.

Let’s tackle the worst one first: Estimated quarterly taxes. People with self employment income (Freelancers and artists!) are often shocked at how high their taxes are. The short answer here is self-employment tax. When your income comes in the form of a 1099 or from selling bespoke lingerie or topiary design services from your own business, that money is not just taxed at your income rate – it is further subject to 15.3% self-employment tax. This isn’t an injustice – employees who get a W2 also pay into the system, but they only have to pay 7.65%, and their employer, out of the employer’s pocket, pays a mirror-image 7.65%. When you’re self-employed, you are both employee and employer, so you pay both halves. And if you want to look deeper into the taxes on this, you even get the same discounts on the employer half that big employers do. It’s just that when you’re on your own, and presumably don’t have an HR or accounting department guiding you gently through this process, it hurts more to pay it.

Estimated quarterly taxes exist to approximate the tax withholding that happens with a regular paycheck. But of course, it’s on you to make it happen. The rules are this: if your total tax bill this April was over $1000 (don’t confuse this with the amount of your refund or the amount you owed – that’s just the part where you make change with the government from what you’ve been paying all year), then you are required to pay quarterly estimates this year. You may owe them for your state, too (those rules vary, and the amounts are smaller). The deadlines are:

First payment due: tax day (today). April 18, 2017

Second payment due: June 15, 2017

Third payment due: September 15, 2017

Fourth payment due: January 16, 2018.

If you don’t pay them over the course of the year, you will incur non-payment penalties and interest. Much scarier, you may face an outrageous tax bill come April, that you are unable to pay. Please avoid this, for your own health. Pay here. You can actually pay money in at any time – if you overpay, you can apply the excess to future quarterly payments or get it refunded. When you earn less money than you did in the prior year, you’ll owe less in quarterly payments. When you make more money, you’ll owe more. As with W2 withholding, it is proportional to the amount of income you earn. You’re not expected to predict your future income accurately down to the last dollar (that wouldn’t be fair). But as long as you pay 100% of what you owed in tax last year, you will not be penalized with fees or interest. However, you still may owe more tax – you settle up the total when you file your 2017 taxes in winter 2018.

There’s a start-up that I like, trying to ease this pain for freelancers, aptly called Painless1099. If you sign up with this link, AFC users will get a 15% discount. Basically, Painless1099 allows you to set up a bank account where you deposit your freelance income, and they set aside the correct amount of estimated tax, based on your actual numbers. They charge a modest per-transaction fee, with a yearly maximum fee of $125. If paying this small amount saves you from a financial disaster next tax day, it’s well worth it. This way, you don’t get blindsided by a huge tax bill in April.

Bookkeeping

I’ve addressed the need for bookkeeping before, but to recap, if you have self-employment income or run your own business, then you are required by law to keep accurate books recording your income and expenses. I don’t know one person on earth who doesn’t have a little room for improvement in this area. So if your system isn’t great, take some time now to retool it. A spreadsheet is fine if your business is simple. If not, consider bookkeeping software such as Quickbooks self-employed or Xero. Quickbooks has been making improvements, and their self-employed app is pretty good. But be forewarned that it is designed to feed you into other Intuit-owned products (like TurboTax), and so does not play well with other programs you might use. Xero is cloud-based and easy for an accountant or employee to log in to from another location. They are a more tech-forward company, and I like that they are quicker to make updates and their software is more intuitive. I am personally biased towards cloud-based bookkeeping software, as it eliminates problems of older software that won’t translate to your new computer, or vicious dilemnas caused by multiple bookkeepers working on separate files. I don’t recommend any version of the old Quickbooks desktop software.

Missing deductions

If you’ve been reading my column, you know that you need to keep receipts to back up any expenses you list on your Schedule C. This year, I worked with the artist professional development guides at Kind Aesthetic to create this lovely visual chart of what is deductible for an artist on the Schedule C (and where to put it).

Often, freelancers miss deductions they are entitled to because they aren’t aware that they are deductible. So to help you track some of the often-missed deductions, here are a couple apps (plus discounts).

Xero Taxtouch. This mobile-friendly app made for freelancers lets you hook up to your bank feed, and swipe left or right to categorize deductions as business expenses (deductible) or personal ones (not). It makes it easy to create a report at the end of the year to give to your accountant, and since it connects directly to your bank feed, it captures everything you spend.

Mileage is a deduction people often miss because they don’t track it. The IRS rules require you to keep a mileage log if you’re going to deduct your business mileage, and this rule scares a lot of people off. But the deduction is huge: 53.5 cents/mile for 2017. This means if you drive 100 miles to meet a client, you get a little over $50 of deduction. If you drive for your business at all, the money you save is worth the effort.

MileIQ is one of several mileage apps that use the location detection on your phone to automatically record your mileage. Similarly to Xero Taxtouch, you swipe left or right to categorize drives as business or personal. You can also track the things people often don’t – volunteer miles driven (deductible at 14 cents/mile, if you itemize) and medical miles driven (ditto, but 17 cents/mile, with a high threshold before it’s useful). The free version doesn’t capture everything, so it’s useful to get the full version. ArtFCity readers can get a 20% discount by using this code: HCOL124A

And in the service of having a better tax year next year, I built an online tax course with the help of Kind Aesthetic, specifically for artists. We worked hard to make it clear, accessible and empowering, and I think it’s a great tool to help artists realize their rights as small business taxpayers, and how to armor themselves with best practices. It’s one hour.  (And it’s 20% off for AFC readers, using code: 2017MARCHAPRIL) Here’s the link.

And lastly, if you’re reading this in a sweat because you still haven’t filed your 2016 taxes, fear not. You can still file for an extension, as long as you make a payment for what you think you owe, and postmark it today. The extension deadline is only an extension of time to file, not an extension of time to pay. I hear you asking how you’re supposed to know what you owe before you file. Make a guesstimate based on last year’s tax due. If you underpay or don’t pay at all, and you expect to owe money, you’ll be charged interest and penalties until the day you file and pay. If you overpay, you’ll get a refund. Don’t forget to apply for an extension for your state, too.

And for everyone, today is your deadline to put money into a retirement account to credit towards tax year 2016. If you put money into a traditional IRA, it saves money on your taxes this year (so be sure it’s listed on your 2016 taxes!). If you put money into a Roth IRA, you don’t need to do anything on your tax forms, because there is no tax savings when you put it in – but when you take it out one day, it will be sweet and tax-free.

Let’s make 2017 your best tax year yet. Good luck everyone.

DISCLAIMER: True tax advice is a two-way conversation, and your accountant needs to hear your full situation to apply the rules correctly in your case. This post is meant for general information only. Please don’t act on this alone.

Bio: Hannah Cole is an artist and Enrolled Agent. She is the founder of Sunlight Tax.

from Art F City http://ift.tt/2o0qw14 via IFTTT

[coffitivityofficial]

1099 taxes don't have to be hard.

To our freelancers and 1099er friends - now there's a better way to save for tax season!

First off, congrats. You made it through tax season 2015! Hopefully you came out unscathed, but if you're anything like us, taxes were a nightmare. Trust us, we get it. Which is why over the past few months we've been building Painless1099 to solve the headache of 1099 taxes for people like you and us!

Painless1099 is the first automated tax withholding for 1099 hustlers. Think: freelance creatives, 1099 contractors, on-demand drivers, you name it - anyone who collects a 1099 and has to pay Uncle Sam throughout the year. We're talking about people like you and people like the team here at Coffitivity! Painless1099 is the simplest way to save for your quarterly taxes so you can worry less about your tax bill from 1099 income and focus more on doing the work you know and love. With a Painless1099 bank account, you can direct all of your client billing to your new, smart withholding account and count on us to do the rest! We separate what you should set aside for taxes and we'll send your remaining cash directly to your personal checking account. No hassle, no headache; you'll be squared away with enough cash saved to pay taxes on time every time. The best part - Painless1099 is completely free to use!

We're opening up the first few Painless1099 accounts today just for our Coffitivity family and we'd love for you to check out the platform, get signed up, and start saving for Tax Day 2016 today! Pop over to Painless1099.com to get started and if you have any questions, don't hesitate to drop a line to hello@painless1099.com! And of course, if you think of someone you know who needs a Painless1099 account, don't forget to share this with them. We're stoked to having you using Painless1099 and can't wait to make your taxes a little easier this year! As always, stay creative, -the Coffitivity crew

[sirawkwardj]

I don't office good.

[painless1099]

Have You Made Your Quarterly Estimated Tax Payment?

It’s once again that time of year! That’s right, the last quarterly estimated tax payment for last year is due next Tuesday, the 17th. No fret, paying your estimated taxes can be easy, especially if you’ve been using Painless1099 to stay on top of your savings. If you’re not sure what quarterly estimates are, check out this quick overview on everything you need to know about quarterlies.

Once you know how much you need to pay, you’ll need to hop over to IRS Direct Pay website to actually make your quarterly estimated payment. Follow these 6 easy steps to finally put your 2016 tax burden to rest:

Head over to the IRS Direct-Pay

Click on “Make a Payment” in the Direct Pay portal

Select “Estimated Tax” under Reason for Payment

Select “2016” under Tax Period for Payment

Fill out the remainder of the fields with your information

 ** You’ll need to enter your personal information exactly how it appears on a 1040 tax return from within the last 6 years so it may be helpful to have one on hand.

Use your Painless1099 account and routing number as your banking information

Make sure that you get your quarterly payments taken care of before January 17th to avoid costly penalties from the IRS.

Happy Taxing!

--

Dear Reader,

This is meant as a guide, not professional financial or tax advice. If you have any questions about your taxes or your deductions, hire an accountant or ask a tax professional.

Love,

Painless1099’s Lawyers

[painless1099]

Why Automation is Essential to Any Freelance Career

Being a freelancer comes with a laundry list of business administrative duties. While you may have gotten into freelancing to focus on delivering your best work to clients, doing daily upkeep on your business can add a ton of extra pressure!

In order to build a successful career as a freelancer, you’ll need to create systems to be able to manage all of these tasks as efficiently as possible. This means focusing on the work that you do best and outsourcing tedious tasks that require valuable time and attention. Luckily, new technology makes it super easy to automate a lot of the time consuming tasks that come with being a solopreneur. 

Managing the financial obligations that come with self-employment is an area where we as freelancers tend to get bogged down the most. Most of these responsibilities are things that the HR department would handle at a typical W-2 job – like tax withholding, setting up health insurance, and getting into some kind of retirement plan. It can be tricky to handle some of this stuff on your own. Luckily, companies like Honest Dollar and Freelancers Union have made it super easy for freelancers to find coverage and retirement plans that best fit their particular needs.

However, this is only half the battle. Making regular contributions to a retirement plan, covering monthly insurance premiums, and then remembering to set money aside for self-employment taxes can feel like a full time job all in itself. Throw in fluctuating income throughout the year and keeping up with your budget, juggling it all is, well, damn near impossible.

This leads to huge segments of the self-employed working without the benefits necessary to build a stable career. With 20% of freelancers completely uninsured and even more folks working without saving any money for retirement, it’s important to make sure you create a system that allows you to work with the coverage you need.

At Painless1099, we’ve found that automating the process of saving for and remitting payments for these financial obligations the best way to ensure that you stick to your budget. And we’re not alone! A recent white paper report released by Etsy shows that individuals are much more likely to save and fund their benefits when there is a system in place to allow them to “set it and forget it”.

Not only is this our motto at Painless1099, but we truly believe that this is the best way to manage your financial obligations and focus on the work that matters most. That’s why we’ve built a tool that automatically withholds a portion of your income for financial obligations.

In looking at which of these financial obligations is the most time consuming throughout the year, we realized saving for taxes is an on-going struggle for freelancers. With large portions of 1099 earners reporting spending upwards of 35 hours on taxes throughout the year, we decided to create a smart savings account that automatically withholds the percentage of your income that you need to save for taxes and transfers the rest – what’s safe to spend – directly to your personal checking account. It’s essentially the W-2 withholding but designed for your self-employment income.

Obviously taxes are only one piece of the puzzle. Being able to automate the process of saving for all of your financial obligations is where the true value is at. That’s why we recently launched PainlessBENEFITS. Now you can easily create your own self-employment portable benefits package and automate payments for all of your financial obligations. Once you have everything set up, you can go back to work without the stress of keeping up with a handful of due dates each month.

There’s nothing easy about being a freelancer, but the reward is well worth it. That’s why it’s so important to make sure you’re always working as efficiently and have the benefits in place to maintain a stable career.

[painless1099]

The Digital Water Cooler

During my conversation with a user of Painless1099, I was introduced to a new concept - the idea of digital water coolers for remote workers. It wasn’t totally clear at first but when she explained it further, it made perfect sense. A digital water cooler is a place on the internet where folks who are working remote can commingle with other remote workers, just to chat. If you think about it, the water cooler or coffee pot in most offices serves as much more than just a place to grab a quick drink. This is where you actually create bonds with co-workers, get others perspectives on something you've been struggling with, or even just take a second to be a human and talk about your weekend plans. When you’re working remotely, you don’t have a water cooler to gather around when you need a refreshment or some conversation.

That’s why these groups are super important for remote workers to build a sense of community, a topic we wrote about recently. These communities provide opportunities to ask for advice, complain about a client, or make friends with folks who are very like-minded and on the same grind that you are.

So what do they look like exactly? These ‘water coolers’ can be found all across the web, from Facebook groups to Reddit threads. Below you’ll find some of our favorites, why we like them, and what you can expect to get from them.

/r/reddit:

/r/freelance: is a reddit thread of 41,000 freelancers asking for help and providing spectacular feedback to each other, both good and bad. The topics on this thread are a little more serious but it’s a great resource for all of your questions and concerns about being self-employed. If you’re going through something, chances are someone has posted about it and others have chimed in to help.

Facebook Groups:

Screw the Nine to Five Facebook Group: Well first off, the name alone deserves some attention. Next, the sheer size of this group is super valuable. It’s an online community of 44,000 similar folks, so you’re bound to find someone you like. The ‘scroupies,’ as they’re called, are constantly posting inspirational quotes, funny stories, and different resources they use to crush it. The moderators are also super engaged and hold some pretty solid seminars on being self-employed.

BAMF: As the name implies, this channel is predicated on fun but also sharing solid ideas and work. Badass Marketers and Founders is group of exactly what the name implies, folks in the marketing and startup world who are mostly self-employed and good at what they do. We’ve seen posts of all kinds here, meaning they are a lot less strict about what the members are connecting over. Last we checked there were 14,700 people in it, and it’s growing quickly.

#SlackGroups:

#WorkFrom: is a slack channel brought to you by the wonderful folks at WorkFrom. This Slack group is a huge community of freelancers, remote workers, students, and travelers who are looking to work better from wherever they are. Super relevant. Joining this group comes with perks for both the paid and the free memberships. For the free membership, you’ll get recommendations for remote worker-friendly work spaces, wifi speeds, and real-time seating capacity. If you’re really feeling it, you can pay $5 a month and get access to the chat room, discounts on a ton of dope products, and more *exclusive* features.

#LemonAid: this one is for the ladies, particularly when the going gets tough. LemonAid is a place to seek help when your life or work, or both, hit that inevitable rough patch. As put on the website, “We believe in openly speaking about mental health, trauma, human rights, and professional challenges.”-- Things that we believe we all need to have conversations about from time-to-time.

In-Person (because face time is important, too):

Freelancers Union Hives: These groups consists of local freelancers meeting to talk about a particular thing. These topics range from Health and Lifestyle to Freelancing 101. Along with joining a Hive, we recommend considering joining the freelancer’s union. Essentially, it’s a community of over 300,000 freelancers all trying to do the same thing: do their own thing.

Meetup.com: Meetup is an awesome place to connect with people near you that are interested in the same things you are. There is everything from people meeting up to talk work to people meeting up to exercise together. Their website makes it really easy to find groups in your area and learn when they are meeting next. If you don’t see what you’re looking for, you can step up and create your own Meetup, pretty flippin’ cool.

There are several more support groups for freelancers, these are just a few that we picked out and thought were worth sharing. We can’t stress enough how helpful these digital water coolers can be for the health of your freelance business. So next time you need some advice, a fresh perspective, or just someone to shoot the shit with, don’t forget about these digital water coolers.

If you think we missed any groups that you find super helpful, reach out to me at aaron@painless1099.com and I’ll be sure to update the list!

[painless1099]

Have You Made Your Quarterly Estimated Tax Payment?

This year’s third quarterly estimated tax payment is almost due - September 15th to be exact. If you haven’t already, now’s the time to make sure you get your payment into the IRS to avoid any underpayment penalties. If you’re not sure how much you owe, or want more information on quarterly estimated taxes - this overview can help get you up to speed.

Once you know how much you’re on the hook for, you’ll need to get that payment to the IRS. If you’ve been saving with Painless, you can now have your quarterly estimated payments automatically submitted from your Painless1099 account. For anyone not automating quarterly payments with Painless, we suggest taking advantage of Direct Pay. This option allows you to submit your payment right from the IRS website and can be completed in a matter of minutes. Once you’re done, you won’t have to worry about if the IRS receives your payment on time - you automatically get credit for your payment upon completing the process.

To submit your payment, head over the IRS Direct Pay page and follow these 5 steps:

Step 1: Payment Type

Select Estimated Tax under reason for payment. The remaining fields will automatically populate with the appropriate information.

Step 2: Verify Identity

You’ll need to provide the information from a 1040 tax return you filed during one of the previous six years to verify your identity.

Step 3: Payment Information

This is where you’ll enter the payment amount and the date you would like to submit your payment. Direct Pay allows you to schedule your payment up to 30 days in advance.

Step 4: Bank Account Information

You’ll need to provide the account and routing number of the checking or savings account you would like to submit your payment from.

Step 5: Review and Sign

Double check all of the information entered to make sure everything is accurate and then simply provide an electronic signature to complete your payment.

If you don’t have access to a previously filed 1040, or if you would like to pay using cash or check, check out the IRS payments page for more information on how to submit your payment.

If you’re tired of marking your calendar and keeping up with pesky quarterly payments, automate the entire process by creating your Pianless1099 account today.

Happy Taxing!

— 

Dear Reader,

This is meant as a guide, not professional financial or tax advice. If you have any questions about your taxes or your deductions, hire an accountant or ask a tax professional.

Love,

Painless1099’s Lawyers

[painless1099]

Creating Your Self-Employment Benefits Package with Painless1099

Jumping into the world of working for yourself can be tough, especially when it comes to the ever changing financial landscape of self-employment. Gone are the days when you had access to employer sponsored benefit packages and protections like workers comp and unemployment that are put in place for US workers. It’s incumbent on you to make sure you have decent health insurance, some kind of retirement savings, money set aside for taxes, and some cash in the coffers for any unexpected emergencies.

If reaching financial stability feels like it’s damn near impossible - you’re not alone. With 20% of freelancers completely uninsured, only 8% of folks making contributions to a retirement plan, and 40% of freelancers not putting any cash into savings, it’s easy to see that the current structure of benefits and protections is failing the fastest growing segment of our workforce. Luckily, this problem isn’t going unnoticed. Etsy recently released a white paper that outlines the need for an overhaul to our current system of financing and managing benefits for folks who are self-employed and Senator Mark Warner just introduced legislation to fund testing for building a portable benefits package for the independent workforce. While we’re stoked to see this conversation being held on the national level, legislative solutions and policy conversations aren’t likely to effect real change until 2018 or beyond – which doesn’t help the folks who need a better way of managing their benefits today.

We see tax withholding as the first frontier when it comes to managing your benefits and built Painless to the be the core hub for all of your financial obligations. Interestingly enough, Etsy’s white paper suggests that the best time to fund and manage benefits when you're self-employed is at the point of tax withholding. This means having a system that automatically sets money aside for taxes as well as retirement, and insurance payments and then makes sure that money is sent to the appropriate place on the appropriate date. Such a system would allow self-employed workers to use the “set it and forget it” approach to benefits that’s used when working as a W2 employee of a company.

Our mission here at Painless is to continue building a platform that gives you the ability to easily manage all of your benefits while creating the financial stability you need to build a stable career doing the work you love. As we see more and more Painless users linking things like their Betterment Safety Nets and WiseBanyan SEP-IRAs to their Painless accounts to automate the process of managing their benefits, we’re focused on building offerings and integrations to make this process as seamless as possible.

To make sure we’re focusing on the things that matter most to you, we need your help! We’ve put together a short survey to get a better understanding of what benefits related platforms you’re already using and which ones would be most valuable for you be able to manage within your Painless account. If being able to put managing all of your benefits on autopilot is interesting to you, please take a second to give us your feedback!

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5 Essentials to Command a Flexible Work Life

“I am so sorry to do this, Colleen,” the text began. “But I am flying to California tonight to move in with my sister. I can no longer be your nanny.”

It was 9 pm on a Sunday night. My husband and I had been deliberating on the state of our careers. He had recently started a new job that would involve 50-60% travel. I had been working as a manager at a digital marketing agency, but shoehorning a full-time workload into four days a week. We had a three-year old, a two-year old, and one more baby on the way. And our nanny, who wasn’t the right fit for us anyway, dropped us flat on a Sunday night. Our discussion ended, and we had decided together that I would go in tomorrow morning and quit my job.

I had grappled for years with how to keep my career progressing and meet the needs of my young children. I negotiated reduced hours or remote work into my employment arrangements to be at home for a few more naptimes and a few more mealtimes. I was always a strong producer, so my employers complied. As a former manager, I relate to their position. They were trying to be understanding, retain my value to their company, and avoid looking heartless. Perhaps it wasn’t the best scenario for them, but they wanted to reward my service to their company.

The problem was that even though I took major hits to salary, most teams booked my workload at full-time capacity and resented the fact that I spent less time in the office. My employers weren’t doing this to be unfair. They sought balance, too. They were trying to meet their goals to remain competitive. The result was I ended up working around the clock, even on my off days, and so my home life suffered. It was never enough. I was desperate for a new paradigm.

With equal parts fear and fervor, I took a leap of faith into the on demand economy. The sudden loss of any child care gave me the push I needed to go into business for myself as a consultant, leveraging the tools of the digital economy to work remotely on a schedule that made sense for the needs of our growing family. I was fortunate that my husband was in a place to provide stability for us while I ramped up my operation.

For my first gig, I was heartened to communicate openly about the hourly work commitment. I was empowered when I wrote back with a weekly schedule that was based both on weekly status calls and preschool pick-ups. My employer was clear that this could be a short or long-term commitment, because ultimately they might need someone full time. I took a breath of relief. All cards were on the table.

My new role in our gig economy hasn’t been without its challenges. I’m an independent contractor, but I still need help. Here are my five essentials for success:

Redefine Your Network. You will no longer have the training resources of a company at your disposal, the most important of which is fellow team members. Join online communities of freelancers and consultants for solidarity and support. Your on demand colleagues are your biggest source of feedback, support, and opportunities for new business.

Keep Learning. You are only as marketable as your skills. In today’s global and increasingly automated economy, skills are rapidly changing. Leverage online training and education services, such as Skill Share, Coursera, and General Assembly, to keep your skill set competitive.

Brand Yourself Online. Tools like KickResume help you create your resume, cover letters, and a personal career website. There’s no need to reinvent the wheel. Leverage the work that’s already been done to launch your own personal brand.

Leave the house. Even though you are “working from home,” you still need to leave the house. My children are all preschoolers and younger. If they see me, they need me to be in mom mode. There’s always a trusty local coffee house with free wifi, or even better, shared work spaces from vendors like Liquid Space.

Plan for Taxes. Leverage tax support for independent contractors from outfits such as Painless1099, an automated tax savings service for independent contractors. Be sure to incorporate. Adding “inc” or “llc” to your business protects your personal assets and creates tax advantages. Check out services such as the aptly named, Inc., to file your paperwork.

This post was written by Colleen Keilers, Digital Marketing Manager @ The Mom Project,  Mom to three boys Gerald, age 4 Noah, age 3 & Maddock, age 9 months

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Spotlight: Mom First!

Evin Cooper is a freelance virtual assistant living outside Austin, Texas, who absolutely crushes it. She walked me through how she balances being a mom-of-three and still manages to get deliver solid work for her clients. Her philosophy was so sound, that I couldn’t wait to share some of her insights with y’all.

As a freelance virtual assistant, Evin works for other freelancers who are too busy to do some of the backend business tasks that are essential to keeping their businesses afloat. When I asked her about the impact her work has on her clients she responded with “my work allows my clients to focus on their work, rather than worrying about the backend crap.” (Sound familiar?) Evin has quickly built her business to the point where she’s starting to feel like she may need her own assistant to stay on track and keep crushing it. When I caught up with Evin, it was tax day and she let me know that she hadn’t made her 2017 quarter one estimated payment yet. However, she wasn’t stressing it because she had saved more than she needed in her Painless1099 account.

After spending 10-years as a stay-at-home mom, her youngest was headed to kindergarten and she had to figure out what she was going to do next. Evin and her family live “out in the country” so she knew finding a job wasn’t going to be easy. She did the math and with all the resources it would take to get to a regular job and her (lack of) credentials, she concluded “I would basically be paying to work for somewhere.” Naturally, this didn’t seem like a good option. Then one day, a friend asked Evin for help handling the administrative aspect of her business. She accepted and quickly realized, “it was fantastic. I could work in my pajamas and then go get my kids from school in the afternoon. All while making money to buy groceries and pay bills.” One referral led to another and before she knew it, she had enough clients to start a business of her own.

Evin’s favorite part of freelancing is making good money on her own schedule and still being able to be a mom first, the flexibility of freelancing allows her to not miss any important events with her kids. She also really enjoys the autonomy that comes with being self-employed, as she reserves the right to fire a client if it’s not a good match. “If you have a shitty boss, you’re just stuck with it. You could quit and find a new job, but who does that? You just suck it up.” Although there’s freedom, she admits it took a while for her to learn the discipline it takes to survive as a freelancer. In the beginning she remembers telling herself “Okay, I’m going to eat breakfast and then get to work. Then I’d look up and I’d be on my 8th episode of the office.” Since then, she’s figured out the discipline piece and has built a routine around getting work done. “At first it was ‘oh, I’ll just get it done whenever.’ Now I consistently drop the kids off at 7:30am and pick them up at 3:30pm. So from 8-3 I’m working and have set that expectation with my clients.”

I asked Evin for advice advice for other moms and dads who are trying to balance freelancing and parenthood and her answer was very on-point. “The most important thing is that you sit down with your family and tell them to treat your freelancing jobs as a real job. You have to train your family to know that your work is work. One thing that really helped is making them understand that the hours that I don’t work, I don’t get paid. So if you want me to buy groceries and toys, then you have to have to let me get my work done. Once you set that expectation, you are able to focus more on your work, rather than people wanting stuff from you all of the time.” She also mentioned the importance of finding communities of other freelancers to build a camaraderie with. “I’m a part of a few Facebook groups that kind of serve as the ‘water cooler’ of remote work. It’s good to connect with people who know what I’m going through.”

If you need a kick-ass assistant for your business, hit up Evin here. I’m confident to say that she’s got you covered for all your backend business needs!

Aaron Ware is Head of User Engagement at Painless1099, a smart banking solution that automatically withholds taxes for freelancers. Aaron works to make every experience with Painless1099 excellent. If he's not working, he's probably riding his bike or snowboard.

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Community for Sanity’s Sake

I was maybe a year out of school when I found myself broke, running a startup that wasn’t making money, and wondering how I was going to pay my rent that month. Not even a week later, I found myself face to face with my first client. Granted, I didn’t know he was my first client at the time. He was just a buddy starting a new gig who needed a website and for some reason decided coming to me for said website made sense. In his defense, I’d cofounded a web company by then, so I probably seemed like the right person to ask. I honestly can’t say I was qualified by any means to make the internet for anyone, but he asked, and for some reason I committed to the work. I made a decision, accidentally ended up doing client work, and haven’t really looked back since.

Freelancing is a fickle beast. To outsiders, what we do seems like such a sexy way of life. We don’t have a boss, we go on vacation when we want, we can hang out at coffee shops all day or work in our pajamas from home. Yeah, right. Some of us dive into doing client work on purpose while others of us stumble into work, but regardless of how we get started, we all know this: freelancing is hard. Full stop. Between managing clients, expectations, and our workload, it’s a fulltime job and leaves very little time to clear our heads or take a mental break. For the longest time, I embraced the idea of being a lone wolf and eating what I killed, but more recently I’ve found that hunting with a pack is great for the belly and healthy for the mind.

For that first project, I had no idea where to start, so I did what any self-respecting entrepreneur does. I called someone smarter than me. Fortunately for me, that smarter person was a talented designer, knew enough to hack together a Wordpress site, and was looking for new clients. This was my first experience with how giving the freelance community can be. Sure, I reached out to a friend, but more importantly, I built a relationship with a peer and it was possible the best thing I did for my career in doing client work.

Over the years I’ve continued to do strategy, brand, or copy work for clients or as a speaker talking about innovation and entrepreneurship. I can attribute most of my work to referrals from other freelancers or previous clients and it’s debunked this idea that freelancing is a zero sum game and that there’s only room for one player in any given game. What I’ve really learned is that most of us in the freelance community are not only trying to grow our network of potential referrers for work, but we’re also looking for that group of peers to trade war stories from the trenches. We’re looking for a community to belong to and for those of us with the shared experience of working for ourselves, this is one of the strongest bonds that exists in the professional world. That bond is something I took for granted when I started, but a piece that I’ll never let go of now.

Beyond freelancing, I’ve also spent a fair portion of my time building products and tools for people like us. Coffitivity, for instance, plays the sounds of the coffee shop so we can feel that boost of productivity even when we’re not in our favorite cafe. My most recent project, Painless1099, handles taxes for freelancers so we can focus more on work and stress less about taxes. The commonality in both of these projects is that their growth can almost solely be traced back to that sense of community I mentioned. Coffitivity went from 120 visitors the first day we launched in 2013, to 49,000 visitors the second day. The growth was organic and largely based on word of mouth. The tight-knit crew of creatives and technologists we ran with shared the site with their friends, and their friends shared it with their friends, and so on and so forth. In my experience, we (freelancers) are the fastest group to share tips, tricks, and information with each other and it’s inspiring to be a part of. Interestingly enough, Painless1099 stemmed from the millions of global users we have at Coffitivity. Again, the highly engaged community was quick to plug in and share the bits and pieces of their day that could be improved. From the conversation we had with the “Coffitivity Crew”, we were able to identify taxes as a major pain point for most of us, and we started building a product that tackled the problem. Yet again, friends told friends who told other friends and we had our first cadre of beta testers and volunteer guinea pigs. The feedback and enthusiasm has been phenomenal and makes me proud to continue to be a part of the freelance world.

If you take nothing else away from my ramblings, I want you to take this one piece of advice: Find your people and grow with them. Seek out the people who support you and your work. Rely on them, ask them questions, turn to them for advice, lean on their shoulders after a hellacious day. That’s the only way to survive in our world and it’s the best way to hone your craft. Freelancing is only as hard as we make it and if you’re diligent about finding peers who not only support you, but also push you, you’ll be so much better for it. I was fortunate to learn this early and it’s possibly the largest contributing factor to me being able to continue in the world of self-employment without losing my mind. It’s awesome to be a part of and I’m glad to be here. I think I’ll stay for a while.

Ace Callwood is the co-founder and CEO of Painless1099, a smart banking solution that automatically withholds taxes for freelancers. Prior to Painless1099, Ace co-founded Coffitivity, an ambient sound website and app that was named one of TIME Magazine’s Top 50 Sites of 2013. Ace is a graduate of Virginia Commonwealth University and lives in New York, NY.

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Destressing Tax Day - Freelance Edition

Being self-employed is a blast, but it ain’t easy. Finding clients, managing expectations, keeping track of time and appointments, and then actually getting work done is a handful to say the least. And, of course, when tax season rolls around you have another full plate to deal with getting your 1099 taxes figured out. Sorting through receipts and praying you don’t get blindsided by a bigger bill than you expected is fun, right? Yeah, no. Tax season should be just as easy for someone who’s self employed as it is for folks with a W-2 job, which is why we put together this short list of things you should be thinking about to help avoid a tax nightmare. Happy Taxing!

1) Tax Day is Today (April 18th)

This is not an April Fools’ joke. Uncle Sam has moved the ball a bit in recent years, which means the 18th (yeah, it’s today) is now your last day to pay taxes owed and avoid penalty and interest charges. Hopefully the flexibility of freelancing gives you a bit of time to dig into your books if you haven’t already. Go ahead, fire up TurboTax to get your 2016 taxes filed or at least file an extension. It’s game time.

2) You can always file an extension if you’re behind

If you’re feeling behind the 8 Ball, make sure to file an extension for your personal taxes (super easy to do through most tax software). You can also head to the IRS Free File page for a run down of options to file your extension for free. Remember, as of last year, the IRS has the power to revoke or deny your passport in certain cases of unpaid taxes, so use the afternoon to take a look while you still have time!

3) Keep track of your expenses

If you’re self-employed, you have ample opportunities to take tax deductions. Anything from your home office, to mileage driving to meetings, to coffees with clients, to the water bottles you keep stocked in your Uber can be written off if you’re prudent about keeping records of these expenditures. Fortunately there are some great options out there for tracking expenses. Check out QuickBooks Self-Employed or Xero Tax Touch for a great way to categorize expenditures for clients, MileIQ for logging mileage, or 99Deductions for understanding what you can expense. While you’re at it, take a look at Hurdlr, which is the mobile app built by the team behind 99Deductions. With so much awesome technology at our fingertips, there’s no reason to get behind on expenses over the year!

4) Find a great accountant

Of course, this close to tax time, it may be a little late to dig through a ton of records for this tax season. If this is the case, don’t despair, you can hand off your load to a pro this year and get advice to make sure you’re not in the same boat next year. For instance, Sunlight Tax is a phenomenal resource for anybody who is self-employed (not just for freelancers as the name might suggest).

5) Make sure to save 30% for taxes.

Saving is hard — no surprise here. Even if you’re meticulous about your expenses, you’re still expected to pay quarterly estimated taxes on roughly 30% of your self-employment income, which means you need to be keeping an eye on not only how much you earn, but how much you set aside for Uncle Sam. The good news is, there are apps that automate aspects of your tax burden and run in the background so you don’t have to pay attention to them. Painless1099, for instance, is a smart bank account that automates tax withholding from each payment of 1099 income you receive. With a Painless1099 account, all you have to do is connect your direct deposit or invoicing tool to your new smart savings account and input a few tidbits of information about your tax status. Once you’re setup, Painless will watch for 1099 income, separate taxes based on your tax status, and pass your spendable cash along to your personal checking account. Ultimately, this frees up time to focus on your work rather than thinking about manually managing your taxes every time you get paid.

All in all, tax season doesn’t have to be stressful. The beauty of staying on top of your 1099 taxes is that you can treat April as if it’s just another month. If you’re ever looking for more tips on being self-employed, you can check in via the chat portal on our home page. If you want to sign up, you can do that on site as well. We’d love to have you!

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What If I Can’t Cover My Tax Bill?

Tax day takes on a whole new meaning when you’re self-employed. When you’re the employee of a company, you simply file your returns and cross your fingers that you get more back than last year. When you’re self-employed, it means pulling together all of your receipts from the entire year, making sure you’ve made all of your quarterly payments, and crossing your fingers in hopes that you’ve saved enough to cover your bill. Any miscalculations along the way could lead to getting blindsided by larger bill than expected on tax day. Due to a major lack of resources available to help folks who are self-employed manage their tax obligation, this year end surprise is actually more common than you may think.

If you find yourself coming up short on tax day, don’t panic! Take a deep breath, and follow these steps to keep the tax man off your front porch:

File your return

The absolute worst thing you can do if you don’t have enough cash to cover you bill is to not file your return at all. For each month your return is late, you’ll automatically be charged a failure-to-file fee of 5% percent of what you owe. This penalty won’t exceed more than 25% of that total amount, but I think it goes without saying, having to pay a dollar over what you owe sucks. The best thing you can do is file your return on time and pay as much of the obligation as you possibly can. You’ll still have to pay a failure-to-pay penalty of 0.5% of the amount owed each month but with at least paying some of that obligation, this penalty will be a lot more palatable.

Apply for the IRS installment agreement

If you know you’re going to need a little bit of time to pull together some cash, the IRS allows for you to make monthly payments through their installment agreement. As long as you’ve already filed your return and owe less than $50,000 you probably qualify, however, there are still some fees and penalties associated with this method. Depending on the how you choose to actually remit cash to the IRS, you’ll be charged a setup fee ranging between $31 (direct debit - online payment agreement) and $225 (regular installment agreement). You’re also still on the hook for late payment penalties, but with the acceptance of your installment agreement this will be cut back to 0.25% of the amount owed.

Apply for an offer in compromise

If you experienced a financial emergency or simply don’t have the means to cover your tax obligation, you can potentially settle your debt for less than the full amount owed. To do so, you’ll  need to submit an application for an offer in compromise. This is the IRS’s way of giving a fresh start to taxpayers who’re unable to pay or have run into special circumstance that hinder their ability to pay off their debt. The IRS is fairly strict on the applications they accept so you’ll want to make sure that you’re qualified before submitting your offer and paying the $186 application fee.

Know your obligation

At Painless1099, we know all too well how complicated calculating your obligation can be. Not to mention, any miscalculation can land you right back in the same position of not having enough saved to cover your bill. Current forecasting worksheets and tax estimators out there generally only focus on either the federal or state portion of your obligation, leaving you to with a half-painted picture of what’s to come. Not to mention just working through those resources alone can be so complicated that you’ll feel like you’re filing your actual tax return. That’s why we took it upon ourselves to build a one-stop-shop self-employment income tax calculator. Calculating your obligation only takes a minute or two and you’ll have everything you need to make an informed decision on how to best pay for you obligation.

Avoid ending up in the same position

The best way to make sure you don’t come up short on tax day is to separate some cash into a dedicated tax savings account each time you earn 1099 income. Having a dedicated account keeps your tax savings out of arm’s reach so you know you’ll have enough saved to cover your obligation at the end of the year. The good news is that we’ve made this super easy to do! Painless1099 is a smart savings account that automates this entire process. When you sign up, we’ll set you up with new savings account with our banking partner. As your clients deposit your income into your new account, we’ll automatically calculate and withhold the amount you need to set aside for taxes right in your Painless account. The rest, what’s safe for you to spend, is transferred directly to your personal checking account. It’s essentially the W2 withholding you’d have as an employee of a company, but it’s designed specifically for your 1099 income. Avoid that “Oh, Sh*t!” moment on tax day - automate your tax withholding with Painless1099.

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Spotlight: From the Inside

Typically, we use our Spotlight series to tell the stories of how our users have established themselves in the world of self-employment. This naturally led to us sharing a few of our own stories around the shop. After realizing we had some pretty unique stories of our own, it only seemed right to share them with you! To kick things off, I caught up with our CEO Ace to get the full story on his journey through self-employment and how that lead to helping freelancers with their taxes. From reffing soccer, to doing contract work with the US Army, to helping clients with brand-strategy and copy, to being a full-time entrepreneur; Ace has been around the (self-employed) block, to say the least.

Ace was self-employed well before he even realized it. The son of two entrepreneurs, working for himself kind of came naturally. At the age of 12, he was already collecting freelance cash through reffing soccer on the weekends. From the jump, he really like the dynamic of the work. “I never thought of it as being self-employed, it was just like ‘this is cool and I can do what I want, when I want to and make money.’”

It really hit him that he was self-employed when he turned 16 and started driving. “I was no longer relying on my mom to get to gigs so it really started to feel like I was doing my own thing.” Around the same time his friends started working more traditional jobs, is when it really started to set in that what he was doing was definitely different and surely suited for him. “While my buddies had set schedules at work, I was taking (and declining) jobs when I wanted to.” Which, he noted was his favorite part of being self-employed: autonomy. “The beauty of what we do is that you get to make the decision to work. If sticking to a 9-to-5 cadence [when self-employed] allows you to make money and connect with your folks, that’s awesome. If being flexible is your thing, picking and choosing when you work and when you play is awesome, too. If you decide to take a day off in the middle of the week because you picked your one night to go out, that’s also doable. Again, the beauty is being able to choose, which I really like.”

Early in college, Ace got the chance to work with the US Army on a contractual basis. In his words, he basically got to spend 2 weeks at a time in the woods “blowing shit up”. He fulfilled these contracts with some of his best friends, which built a sense of comradery. “Something I’ve learned to appreciate accross all of my contract work, is having folks around who you can commiserate and build rapport with.” He went on to mention that these relationships are most important when you hit “The Suck”. This refers to the reality that self-employment is hard, and going through some rough patches is pretty much inevitable. “Having other people who get it and can offer advice on how to make it through those tough times is super valuable.”

Towards the end of college, Ace began to utilize the skills he learned through the entrepreneurship program at VCU to help a few friends-turned-clients with some brand strategy work. The nature of these relationships allowed him to have overlap with some of his closest friends who were also getting into contract work, reiterating the importance of comradery in the world of self-employment. “Collaborating on this work was important because we were doing work for people who were both friends and clients. This leads to a pressure to deliver both professionally and personally. Working with people I trusted helped me to manage this pressure and provide solid deliverables.”

Another concept he picked up during this time was the idea of scheduling your day around the times when you get your best work done. “While working on my first business in school, I pulled a bunch of all-nighters and remember having a specific realization that I was getting really good work done during these hours. Over the years, I’ve been able to hone in on this concept and now make an effort to really schedule my day around it.” As a natural people person, Ace strategically schedules as many of his meetings and calls for the first half of the day. “Since working with people comes natural to me, I try to knock out all of my meetings and calls in the morning so I can focus on the most strenuous tasks - when I really have to devote brain power - when I’m most productive.” This frees up his afternoons so he can spend time catching up with emails and getting started on the days work. “Come 5pm, I’m really diving in and getting my best work done until about 1 or 2am.” A traditional 9-to-5 job would never allow Ace to take advantage of his most productive periods -  another reason he loves self-employment.

As previously mentioned , Ace has been all over the self-employment spectrum. “Look, the way we think about work has shifted pretty drastically. More people are plugging in and doing things that move the needle because they’re passionate or they have a certain lifestyle they want to lead.” One thing that has remained true throughout each phase of his self-employed journey is the need to continuously get good work done. Choosing self-employment to have the freedom to pursue the life you’d life you’d like to lead comes with the responsibility of consistently delivering quality work that your clients are willing to pay for. The need to constantly optimize workflow and deliver quality work lead him and fellow co-founder Justin, to build Coffitivity, a tool that plays ambient coffeeshop sounds to help boost creativity. “We had to do really good work and Coffitivity was a tool that helped us do that.”

Like good entrepreneurs do, Ace and Justin made an effort to meet the folks that were using Coffitivity and found that many of them were also self-employed and feeling the similar pain points. “We asked Coffitivity users ‘If you could focus on the stuff that you love and do it full-time, what would someone need to be managing to enable you to do that?’” The answer they heard over and over was the financial aspect of being self-employed could be made more simple, particularly the tax portion. Around the same time, they experienced the pain of not having saved enough for self-employment taxes. Once again seeing an opportunity to optimize workflow in the world self-employment they built Painless1099, a tool that automates tax withholding for the self-employed.

As you can probably tell by now, Ace is no stranger to self-employment and is always game to chat about all things 1099. Hit him up on on twitter at @acecallwood.