Dates to Keep You Straight

Every year, Freelancers have an important list of dates to remember and act on, primarily those related to tax filings, retirement account management and health insurance plan enrollment. To help you stay organized, I’ve compiled this date planner that brings together all deadlines into one document that you can bookmark, copy into your calendar or even print out and post on your refrigerator.


January 31, 2019: 1099-MISC due to contractors
Those who hired Freelancers (independent contractors) to whom they paid $600 or more in the previous year must send 1099-MISC forms by January 31, 2019.  If a client paid you less than $600, then you probably will not be mailed a 1099-MISC, although the IRS nevertheless requires you to report all income.

Do keep scrupulous records of who owes you a 1099-MISC so that you can accurately report your income on your tax return.  Your clients will also send 1099-MISC data re: you to the IRS and any differences between your numbers and the clients’ could trigger an audit.  If you haven’t received a 1099-MISC from a client by January 31, contact your client ASAP and request a re-send.

If you used any subcontractors to whom you paid at least $600 last year, you must likewise send them a 1099-MISC by January 31.

April 15, 2019: Individual income tax filing deadline
You have until April 15, 2019 to file your Form 1040 individual income tax return for 2018. Be aware that April 15 isn’t the deadline to pay your taxes — tax payments for Freelancers are due on a quarterly schedule (see 2019 quarterly estimated tax deadlines, below). If you wait until the tax filing deadline to pay your taxes, the IRS may charge you penalties and interest on top of the tax you owe.

If you’re still waiting for information, or you’re too busy to file a return by April 15, you may apply for a six-month extension that gives you until October 15, 2019 to file. The extension application needs to be filed by April 15, 2019. Remember again that the extension is for filing, not paying your taxes.  Payments are still due on the quarterly schedule no matter when you file and penalties and interest can accumulate if you wait to pay.


The IRS requires business owners to pay income taxes on a quarterly schedule. This may seem like a hassle, but it’s easier to pay in four installments than to try and come up with a whole year’s worth of income taxes all at once.

Here are the 2019 deadlines for quarterly estimated tax payments. Note that the four quarters are not of equal lengths: the 2nd Quarter covers only April and May, while the 4th Quarter covers the last four months of the year.

DEADLINE                                                         PERIOD COVERED

April 15, 2019                                                     January 1 – March 31, 2019

June 17, 2019                                                      April 1 – May 31, 2019

September 16, 2019                                           June 1 – August 31, 2019

January 15, 2020                                                September 1 – December 31, 2019



April 15, 2019: Deadline to set up and contribute to an IRA for 2018
Even if you made no contributions to your retirement savings account in 2018, you can still make a 2018 contribution to an IRA up until April 15, 2019. This includes traditional, Roth and SEP IRAs. You can also make 2019 contributions to these plans from now up until next year’s tax filing deadline of April 15, 2020.

December 31, 2019: Deadline to set up an individual 401(K) 
An individual 401(K) is another type of plan that Freelancers can use to save for retirement. One important detail is that an individual 401(K) must be established by December 31st of the first plan year (as opposed to an IRA, which can be opened up until April 15 of the following year). That means it’s too late to set up an individual 401(K) for 2018, but you may set one up for 2019.

Contribution limits 2019 update:

Solo 401(K)                                                                                                                            Employer: 20% of net self-employment income                                                            Employee: 100 % of earned income up to $19,000 (for age 50 years +, up to $25,000)   Total combined contribution: $56,000

Traditional or Roth 401(K)                                                                                                     $6000 annually $7000 if age 50 years +

SEP IRA                                                                                                                                               The lesser of 20% of net self-employment income, or $56,000 annually



The open enrollment dates to purchase health insurance for 2020 on the Affordable Care Act exchange will be November 1 – December 15, 2019.  Open enrollment for 2020 through the national health insurance exchange will also be run from November 1 – December 15, 2019.


Thanks for reading,




Exit Strategy: The Retirement Plan

According to the Bureau of Labor Statistics, 15 million Americans were self-employed in 2015. That’s 15 million talented, ambitious, disciplined and self-confident citizens of our nation who’ve taken charge of their professional and financial future and they (we!) are to be congratulated.  According to the Bureau, self-employed business owners and Freelancers represent 10.1% of the population and they are surely the Talented Tenth.

Now for the bad news—self-employed professionals are not eligible for employer-sponsored benefits of any kind, unless they employ full-time workers and are therefore compelled to provide certain benefits that they would also receive.   Otherwise, the 15 million self-employed do not receive paid sick time, holiday time, vacation time, or employer cosponsored health insurance or retirement benefits.  In addition to the self-employed, there are many more millions who work in traditional employment on a part-time basis only, making them unable to receive employer-sponsored worker’s benefits.  Income inequality, anyone?

Let us consider the retirement fund matter, one of the two benefits issues that workers are able to self-fund (health insurance is the other).  If your finances allow you to set aside money that will be used to support you when you’re too old to work,  you will be wise to do so ASAP.

Examine your spending patterns.  How much are you spending on items that you want, but don’t need?  I don’t recommend that you deny yourself all gratification—we all deserve little luxuries every now and again—but some activities and purchases might perhaps be scaled back, allowing those funds to be redirected to prudent investments.

Budgeting a limited income is stress-producing.  Even those who work full-time may be forced to under-fund their retirement accounts, despite the employer matching contributions.  Wages have stagnated for 30 years and living expenses have done nothing but increase.  As a result, many of us are unable to save enough money.  Many elect to utilize money they’ve managed to save for a down payment on a house, rather than saving for retirement.  Financing one’s life 20 or more years from now must take a back seat.

According to the Government Accountability Office,  in 2015, approximately 50% of Americans had no retirement account whatsoever and 29% of those age 55 and older had neither retirement savings nor a pension.  Social Security is not a good fall-back option. The average monthly pay-out to retirees is only about $1294.  For the overwhelming majority, that’s not enough to carry one through more than half a month.

I consider the retirement picture in the U.S. as both a looming national emergency and a national embarrassment.  Corporate governance laws enacted during the administrations of Ronald Reagan, Bill Clinton and George Bush (son) that brought us globalization and the transfer of good paying jobs to other countries, in the process destroying for all time the ability of so many American citizens to earn a comfortable living employed in benefits paying full-time jobs, is the primary reason for this crisis.

The computer age has done the world no favors, either.  So now you can play with Snapchat on your Android while on break at your $12/hour job.  Yes, there have been magnificent technological advances that have helped in many fields, medicine comes to mind.  But are those benefits worth the livelihood of millions?  That’s a good question for the ethicists.

If at all possible, please start a retirement account.  Here are two options for Freelancers and those who work part-time at one or more locations:

myRA is a starter retirement account created by the Department of the Treasury. There are no fees associated with opening a myRA account and you can decide how much you’d like to contribute each month, according to your budget. Automatic withdrawal contributions can be set up through your bank account or paycheck.

If you change jobs, the myRA account is not affected. If you must take money from the account, there is no financial penalty to pay and no additional taxes are taken out. Like a Roth IRA account, myRA is funded with after-tax income. The maximum annual myRA contribution is $5500 and $6500 for those age 50 or older. The maximum amount that can be held in a myRA is $15,000.  Once the $15,000 limit has been reached (or before, for that matter),  the balance can be rolled over into a traditional retirement account.

Self-employed 401(k) profit sharing-plan (Solo 401 [k]) is funded with pre-tax dollars.  You can make contributions as both an employer (because you employ yourself) and as an employee (because you are employed by your sole proprietorship or single person LLC entity). Wearing your employer hat,  one contribution can be up to 25% of annual net profit, or $33,000 ($39,000 if 50 years or older) per year .  A second contribution of maximum $18,000 annually ($24,000 annually for those 50 years and older) can be made while wearing your employee hat.

Better still,  it’s possible to hire your spouse as an employee under this plan and s/he can contribute in the same way as you do,  meaning that your spouse can also contribute up to $53,000 ($59,000 if age 50 years or older) per year .  Open your Solo 401(k) account before December 31 if you’d like to make a tax-deductible contribution this year.

Thanks for reading,





Year-End Tax Planning: Freelancer Options

It’s never too early to start a retirement plan and Freelance consultants are encouraged to set aside money whenever possible.  Be advised that contributions to a self-funded retirement plan are guided by your net earnings from self-employment.  If you net $80,000 this year,  then you may contribute 20%  of that amount,  or $16,000,  to a SEP IRA or Solo 401K plan.  If you are age 50 +,  a  “catch-up”  contribution of maximum $5,500  (in 2014)  can raise your total allowed retirement fund contribution  (and tax deduction)  to $21, 500.  The maximum amount that one can contribute in tax year 2014 is $52,000 and $57,500 for those age 50 +.  However,  if you are a high earner and you consult with a savvy tax specialist,  it may be possible to divert lots more tax-deductible dollars to a Solo 401K than is allowed with a SEP IRA.



The Savings Incentive Match Plan for Employees Individual Retirement Account is a type of traditional IRA that is tailored for small business owners and self-employed Freelance consultants.  As with a traditional IRA,  contributions are tax-deductible and savings held in the account are tax-deferred until retirement withdrawals are made  (age 59 1/2 the youngest and age 70 1/2 the oldest).  If you have employees,  they may contribute to the SIMPLE IRA themselves and you the employer are required to make annual contributions as well,  whether or not the employee chooses to contribute.  You may make a 100%  match of the employee’s contribution,  but the maximum is 3% of your  net earnings,  or you may limit your employer contribution to 2%  of your  net earnings.

Any business entity that employs 100 or fewer workers may establish a SIMPLE IRA for employees and the owners,  too.  If you anticipate growth in your business that will likely cause you to hire even one full-time employee,  then consider a SIMPLE IRA,  because adding employees to the plan is relatively easy,  unlike other retirement plans.  The big downsides to SIMPLE IRA are 1).  the $12,000 annual contribution limit is considerably lower than that of SEP IRA and Solo 401K and 2). the  $2,5000  “catch-up contribution”  for Freelancers and business owners who are age 50 + is paltry by comparison as well.

However,  as a business owner or self-employed Freelance consultant,  you are your own employer and you may contribute to your SIMPLE IRA as both employer and employee.  You may add in up to 3% of net earnings,  in this example up to $2,400,  to contribute $14,4000 in 2014 and $2,500 extra if you are age 50 +.  Finally,  if you don’t make much money but you still want to set aside a little something for retirement,  if your net earnings from self-employment are $12,000 or less,  you may contribute 100% of the amount of your net earnings to your SIMPLE IRA.


A designated Roth Retirement Account is an individual retirement account that exists under the umbrella of your 401K,  solo or traditional  (if the 401K is set up to allow it).  Unlike SEP and Solo 401K,  Roth 401K contributions are made with after-tax income and when you are ready to access the account,  you will draw down tax-free money.   The 2014 maximum Roth 401K contribution is $5,500  ($6,500 for those age 50 +).

Your selection of a Roth designation within your 401K will depend upon your financial circumstances and you should meet with a reliable financial adviser in advance.  An individual or couple might choose a Roth when there are insufficient deductions to itemize at tax time,  thus negating the tax deduction benefit of the other retirement accounts .  The Roth,  paid with after-tax dollars,  gives account holders the benefit of tax-free income during retirement.   Wealthy Freelance consultants who are concerned about minimizing taxes during retirement may also benefit from the Roth.

You may have both a  (pre-tax)  Solo 401K and an  (after tax)  Roth 401K and it is permissible to use the salary-deferred portion of your Solo 401K to make a Roth 401K contribution.  Profit sharing Solo 401K contributions are not eligible to be made as a Roth 401K contribution,  since they are made pre-tax and are tax deductible and you cannot commingle the two.

While Roth 401K income-deferred contributions are NOT tax-deductible,  withdrawals made after age 59 1/2 are tax-free IF five years have passed since your first contribution to the Roth  (known as the 5 year rule).  One is NOT required to take distributions at least by age 70 1/2 and that feature may be useful for retirement cash flow planning.

Thanks for reading,


Year-End Tax Planning: Funding Your Retirement

Happy November.  The year will soon end and it is time to put together a tax planning strategy while there is still time to plan and execute.  There may be business equipment to purchase,  upgrades to make to your website or a seminar to attend,  but we self-employed workers must also fund our retirement.  Traditionally employed workers must also fund their retirement,  but they get help from their employers.  Freelancers are our own employers and we must step up and do all that we can to stash a few tax-deductible dollars in the cookie jar,  so that we can eat when we’re 75.

Whether you’ll squeeze a few thousand dollars out of modest billable hours or you’re looking for a place to roll the overflow from a lucrative year,  saving for retirement is a superb tax planning strategy.  It is also a superb life planning strategy.  Under no circumstances do we want to be old and broke in America.  If one is single,  that is a real possibility.  This is not Europe and the government will not give us any financial assistance in a time of need,  even though we have been tax paying citizens our entire lives.

The good news is that there are good retirement plan options available to Freelancers with a few thousand dollars to spare and the discipline to save.  Also,  the retirement money can be invested in stocks,  bonds,  mutual funds or even real estate.  You might get lucky and see your investment really grow.  Taxes will not be paid until it’s time to draw down on the account  (age 59 1/2 the youngest and age 70 1/2 the oldest).


The Simplified Employee Pension Individual Retirement Account is modeled after the IRAs that every employer offers.  They are evidently the easiest type of retirement account to set up and there are minimal IRS reporting requirements involved.  Your job will be to find a brokerage firm that will set up the plan,  process your deposits,  maybe give you some investment advice and not kill you with administration fees.

Contributions are limited to 20% of your net earnings  (before the self-employment tax).  Contributions are capped at $52,000/year for tax year 2014 and the limit will increase every year or two,  to adjust for inflation.  A married couple who run a business together,  or are each Freelancers,  may open a joint account and save an annual maximum of $98,000 tax-deductible retirement dollars in 2014.  One cannot borrow against a SEP IRA.


The Individual 401K is modeled after a traditional 401K and once again,  the IRS filing requirements are uncomplicated and your job is to find a brokerage firm that will set up the plan,  process your deposits and not kill you with administration fees.  One may contribute money a little differently to a Solo 401K,  in that you may give yourself a  “salary deferral”  in a good year and stash up to 20% of your net earnings into the Solo 401K,  but the annual maximum contribution remains $52,000 in 2014  (the limit will rise modestly to adjust for inflation).  However,  Freelancers aged 50 +  can take advantage of the  $5,500 (max)  “catch-up contribution”  feature,  which allows those who are able to set aside more retirement dollars to do so and contribute up to $57,500/year in tax-deductible dollars.  Another big advantage of the Solo 401 K is that one may borrow against maximum one-half of the assets  (you must repay the loan with interest, to yourself).  Additionally,  a married couple who run a business together can start a Solo 401K retirement plan for the two and contribute up to $98,000 annually as of 2014 and $10,000 more with the catch-up contribution if both are age 50 +.

Next week,   we’ll look at the SIMPLE IRA and more retirement plan options.

Thanks for reading,