Do Your Own Taxes Or Hire An Accountant?

Despite what many have advised, I’ve been doing my own taxes for the past 8 years.  Along the way, I’ve cocked things up, such as one time when I forgot to report the cost basis to over $1 million dollars worth of stock proceeds!  For some reason, I just passed over the stock section of the software.  You can imagine my surprise when I got a tax bill from the IRS for over $300,000!  By not putting the cost basis down, the IRS thought I had another $1 million worth of income that I hadn’t paid taxes on.  Instead, I only had about $10,000 worth of extra income since my cost basis was around ~$990,000 (trading is tough and not worth it!).

After scrambling to gather all my stock purchase prices, I submitted everything to the IRS and prayed it was all just a silly mistake.  I gave the IRS folks a ring in Utah to explain what I had sent in, and they were so nice.  The man on the other end said, “Not to worry, we see these types of mistakes all the time.”  Two months later, I got a letter from the IRS saying I owed them minimal interest, and taxes on only my profits of ~$10,000, or about $3,000.  Phew!  Thank goodness.

Lesson learned.  Always report your cost basis and save all records of transactions.  You know I’ll never mess up that section again.  I just told you a story as to why you might not want to do your taxes yourself.  That said, I cherish every learning experience and would do it over again.


My stock transaction incident happened years ago when I first started doing my taxes myself.  Since then, tax software from the likes of H&R Block have improved tremendously and makes messing things up more difficult.  Overall, it takes me about 2-3 hours a year to do my taxes using HR Block’s tax software and I just love it.  My taxes are complicated too, with rental properties, private equity investments, stock transactions, normal income, side income and so forth.  Here are several reasons why you should do your own taxes:

* You learn how the system works. Once you start doing your taxes, you begin to realize how complicated the US government taxation system is.  You’ll learn how all the nice credits the government tells you about really doesn’t apply to you because you make more than a threshold they never publicize.  You learn what a W2, 1099, 1099-MISC, 5498, 1098, K1, 1040, 8582, Schedule-E all mean.  With knowledge comes the ability to optimize your own taxes.

* You learn about your own finances. Given you now have a better understanding of how the tax system works, you start thinking about your own finances in a different way.  You adjust your own finances in accordance with what the government encourages all Americans to do i.e. buy a home and start a business.  You don’t have to actually go and buy a home or start a business, but you can put in pro forma numbers into the program and see what happens to your taxes if you do.  Doing your taxes allows you to play around with different scenarios and understanding the outcomes.  This is the best reasons as to why one should do their own.

* The IRS people are good people. Contrary to what you read in the movies about big, bad IRS agents crushing people’s lives, IRS folks are actually really supportive.  I’ve called them numerous times to ask for help, and each time they have been so friendly and courteous.  Why is this?  The reason is because they know the tax system is so damn complicated that everybody makes mistakes.  In fact, I’d venture to guess that the majority of taxes done by individuals and professionals have at least one mistake, or one sub-optimal entry.  The IRS are not out there to punish normal folks like you and me.  They are there to help you.  A bad IRS reputation is definitely one of the key reasons why most people are afraid to do their own taxes.

* Your tax professional won’t listen to you. Another simple reason as to why you would do your own taxes.  Some people are very aggressive on their returns.  I was speaking to my CPA friend the other day, and he said a couple who makes only $80,000 a year working in hotel services wanted to deduct $40,000 in expenses!  No way was my friend going to submit that through given his firm’s reputation and his name is on the line.  Most people don’t go to jail for blatant errors on their tax forms.  Instead, what the IRS does is wait 3 years to send you a notice, which contains a 5% penalty a year so they can try and make more money from you.

* You control your own schedule. Although it takes me 2-3 hours to do my own online taxes, once done, I like to let it sit for a while so I can revisit my returns on a later date.  The reason why I wait is because there are tax forms that sometimes come late, such as a K-1 statement for a private company I own.  Another reason is because you want to think things through on what you’ve inputted to make sure everything will fly.  I seldom ever go to the movies anymore because it’s a PITA to go find parking, buy a ticket, sit in a crowded theater, and have people yap on their phones next to you.  Instead, I like to watch at home on my own sweet setup where I can pause to go to the bathroom, or rewind to re-watch the cool scene.


* You are bad with numbers. If numbers make you sick, don’t do your own taxes.  It’s easy to mess up your taxes if you are not careful.  Errors can cost (or gain) you much more than what a mistake free tax return will cost you.  That said, I firmly believe the majority of tax returns have sub-optimal entries.

* You have the best accountant and you don’t care about money. If you have a rock-star accountant who is on the same page with you in terms of tax philosophy, you might as well have him or her do your taxes for you.  Furthermore, if you don’t care about spending $500-$1,500 for an outstanding CPA, go for it.  The CPA might be able to get you much more than an extra $500-$1,500, maybe.  I say maybe, because there’s only so much you can do before you go into the grey area.

* You have an incredibly diverse amount of investments and income streams. If you have 5 rental properties, 3 vacation homes, 5 different private investments, annuities, dividends, a side business and make multi-millions, you probably want to have a season pro do your taxes.  If you only have a W2 and a home mortgage, there’s no reason why you can’t do your taxes yourself.

* You don’t enjoy reviewing your work. If you were the type in school who took your final exam and handed it in without reviewing your answers thoroughly, you want to hire an accountant.  I personally love reviewing spreadsheets, budgets, tax documents, essays, over and over until I get sick of it.

Since you’ve gotten this far, you’re in for a treat.


For the past 8 years, I’ve been using H&R Block to do my own taxes.  This year was the first time I did them online, and I’m pleased to report back that it’s pretty much the same as doing things with their CD software.  I have to admit that my fears of doing my taxes online were two-fold: 1) Security and 2) What if all the work I’ve done doesn’t save.  But, as with anything done electronically, there is a security risk.  I’m glad to see H&R Block online have a nice “Save” button, which does work after I logged in with another browser to check.

My  one and only roadblock was when I came to form 8582 (Passive Activity Loss Limitations) for rental property. When I clicked the box saying I have passive losses for my rental when I first bought it 9 years ago, the program suggested I call an H&R Block Tax Professional because supposedly this is a complicated thing.  Well, it’s not complicated to me, and I wasn’t about to now call an H&R Block Tax professional to do my taxes after I spent 2 hours doing my own.  I clicked “skip” and then the program warned me that the passive loss form won’t be included in my form, and that I might have some issues.  Well that’s not very comforting, given I do have some passive losses!

It turns out after doing some digging, that passive losses for an active landlord is not allowed anyway if you make over $150,000 a year. After $150,000, you cannot carry over any passive losses to help reduce your tax bill once you rental starts making positive income.  What I’m hoping is that the passive losses can be tacked on to my cost basis for the property if I ever sell it, so that my tax bill is less since my profits are less.  I’ve been assured by an accountant this is the case, but we will cross that bridge when we come to it.  For now, I’ve learned a lot, and I’m keeping all records.

Overall, I’m very pleased with H&R Block’s Online system, and I would recommend the product to anyone.  They’ve been refining their DIY software for the past 10 years.  It’s always intimidating to take on new things, but after some practice, all you’ll want to do is do your own taxes.  Once you understand the basic concepts, the rest of it is data gathering and data entry.  It’s a very rewarding feeling learning about your own finances.   Combine straightforward tax software with all the answers you can find on the internet and you’ve got plenty of ammunition to do your own taxes.

Manage Your Finances In One Place: The best way to become financially independent and protect yourself is to get a handle on your finances by signing up with Personal Capital. They are a free online platform which aggregates all your financial accounts in one place so you can see where you can optimize. Before Personal Capital, I had to log into eight different systems to track 25+ difference accounts (brokerage, multiple banks, 401K, etc) to manage my finances. Now, I can just log into Personal Capital to see how my stock accounts are doing and how my net worth is progressing. I can also see how much I’m spending every month.

The best tool is their Portfolio Fee Analyzer which runs your investment portfolio through its software to see what you are paying. I found out I was paying $1,700 a year in portfolio fees I had no idea I was paying! There is no better financial tool online that has helped me more to achieve financial freedom. It only takes a minute to sign up.

Updated 12/7/2014



Sam started Financial Samurai in 2009 during the depths of the financial crisis as a way to make sense of chaos. After 13 years working on Wall Street, Sam decided to retire in 2012 to utilize everything he learned in business school to focus on online entrepreneurship. Sam focuses on helping readers build more income in real estate, investing, entrepreneurship, and alternative investments in order to achieve financial independence sooner, rather than later.

You can sign up to receive his articles via email or by RSS. Sam also sends out a private quarterly newsletter with information on where he's investing his money and more sensitive information.

Subscribe To Private Newsletter


  1. Investor Junkie says

    I have an accountant.

    Based upon what you’ve stated in the past with your portfolio and the amount of taxes you do pay, it sounds like you should have an accountant. You save money not by the deductions in your personal taxes, you save money by setting up properly a legal structure to help reduce taxes. Flexo for example save over 20k in taxes by changing his company from an LLC to an S corp based upon the advice of his accountant. Tax software won’t catch this.

    Also my accountant helps assist me in thing like what I recently got in the mail. I got an unemployment benefit claim from New York for an employee I don’t have and never worked for me! I have to show proof they never worked for me.

    • says

      Saving 20K by going to an S Corp from an LLC is good, but that is where the grey area occurs for me, since this is just a hobby. It would be one thing if he was making over $500,000 or more, but I think he’s making under $250,000 a year. A close to 10% savings in taxes after the switch is not something I’m comfortable with. The IRS is making SCorp and LLC more the same b/c of this.

      Going to an S corp basically allows you to save on employment tax i.e. you pay yourself $50,000 a year, and the other $200,000 profits is left in the corp and exempt from 10%+ employment tax vs. all $250,000 exposed to the 10%+ employment tax in the LLC. If all I did was make money online, I’d do something similar if blogging was my main source of income, but this is just once piece of the puzzle.

      • Investor Junkie says


        I wasn’t suggesting you should do this personally. I’m suggesting an accountant can give you qualified recommendations to change your tax structure to minimize your taxes. Also what Flexo did isn’t considered a ‘grey’ area in taxes. From my understanding this has been tested in the court of law.

        Keep in mind a good account has their own rep on the line if they do something that gets their clients in constant hot water, do you think they will get additional business? Or even better don’t you think the IRS would go after them.

        Bottom line, and no different than say a Google paying 4% in taxes, you have every legal right to minimize your taxes. Paying the full amount in taxes is just silly. I can think of more effective means to use the difference (ie charities).

        I personally don’t have the time (and I suspect you don’t either) to keep current in all of the new tax laws and regulations. That’s what an account is for and I am leveraging their expertise. I’m not suggesting either be a dolt. Understand the tax laws, but don’t be an expert in them and hire someone to do them for you.

        I suspect you don’t change your Land Rover’s oil do you? Why not? I certainly can do it myself, but it’s best to have someone else do it and do it better, more accurate and quicker.

        • says

          I would love to pay less taxes, trust me. Believe me when I say I know taxes well and I consider it a fun passtime :) I’ll explain it more in a future post.

          PS, I do change my oil, filter, and spark plug from time to time. It’s fun!

  2. Sloan says

    I’m 27 and have been completing my own tax returns since graduating from college and becoming independent. I had minimal financial assets which pushed me to self-prep for two reasons: simplicity and frugality. As my investment vehicles and obligations have multiplied, my initially straight-forward tax returns have become more complicated (no more 1040EZ or 1040A) and just yesterday was discussing with coworkers how they do it. Most use online tax-prep from H&R Block or TurboTax. Haven’t decided if I will make the leap yet, but winning this would definitely make it an easy choice.

    Kudos for the timely topic. I subscribe to your RSS, so 2 points?

  3. says

    I have always done our taxes, but our tax situation is not very complex. Turbo Tax has worked out great for us. Although I guess that is just an assumption because I don’t have anything to compare it to.

    I know some people that spend a ton of money to have a professional do their taxes, and they do not have any unusual circumstances. Maybe some people just like the thought of someone else being responsible for the integrity of their tax return.

  4. says

    My tax situation isn’t that complicated, so I just do it myself. I might use an accountant in the future if it’s not worth my time to do my own taxes, but that’ll be a few years down the road for sure (if ever).

  5. Robert Muir says

    I’ve always done my own taxes using TurboTax. Starting last year, it’s been online.

    Sam, it would be great if you had time to enter the numbers in the online TurboTax to see if it comes up with the same results. It’s free unless you want them to print the return and file so it only costs the time for you to enter the information.

    • says

      I hear ya. I’ve already done it with H&R Block Online to see how the numbers are. I’m just worried about the passive loss carryover issue, which I don’t want to lose. Need to talk to an accountant! :)

  6. says

    Doing your own taxes or using a CPA is a personal choice. I stopped doing my own taxes when I started accumulating income property and businesses. The marginal difference in cost was made up in service. Although my situation has changed, I continue to use him because the cost is low and for advice. As I said , it is a personal choice.

    • says

      I think you got that right, when you say it’s a personal choice. If the software has limitations, I’m going to use an accountant. But, the software nowadays is fine, so I haven’t had a need to yet. We shall see. $300-600 is not that bad.

  7. says

    I think that most people can do their own taxes. I help my brother do his every year, but I pay someone else to do mine because they are a little bit more complicated (The Wife is self employed).

    The moment I cleaned myself up after getting a notice like that is the probably about the time I would hire a CPA if for nothing else to have them review the tax return.

  8. says

    I have an accountant do my taxes. It is not because I am lazy, it is because the accountant does a better job.

    Last year, I did my taxes myself (TurboTax online) and had my accountant do my taxes. He found dedications and credits above what I found that covered his fee and then some. Also, if I am ever audited, he is there for me at no additional charge.

    Worth it to me.

  9. says

    I do my own tax and have used both tax cut and turbo tax in the past. This year, I’m trying H&R block on line and it is a bit different. The rental property depreciation looks different to me and it didn’t export everything from last year. I like the offline version better. My book keeping is a bit sloppy in 2010, but I am planning to clean it up going forward.

    I’m planning to keep doing my own tax for now. Your point about learning to do tax and playing with the number is true. I tried putting different numbers in every year – an extra deduction due to baby for example. I’ll get that next year! :)

  10. says

    i agree with this article, doing it yourself has many benefits such as those listed above.

    curious however, what is/was the nature of the passive loss? you mentioned you are an active landlord, so that said what passive loss did you incur and as a result cannot deduct from your business activity of rental properties? i am assuming you do a schedule C for the business.

    • says

      It is rare to be net profit positive after acquiring rental prop immediately in SF. It takes about 2 years to then break even and make money here, hence why most live in the property for a while and let rent inflation catch up to cover costs.

      You make a great point about active vs passive landlording. All I’ve been told by an accountant is that after you make a certain amount of income, you can’t use carry over losses to reduce your tax bill when you make a profit. I’ll check again though!

      • says

        it is true that you can only deduct carried over losses if your business shows a loss, however why didn’t you take those losses in the year they incurred? it sounds like you are actively managing your properties, therefore you should have been able to claim them as cost of doing business, no?

        back to carry over losses, if your business continues to make money, you will never get to use them. i believe they expire in 20 years. they are however retroactively applicable (2 or 3 years if i remember correct). companies will amend previous years’ tax returns to take advantage of the retro application.

  11. says

    I guess I am just lazy… but I prefer having an accountant, sort it. He is a family member who files it up for me, explains it to me and works at making the best for me at an incredibly low price! Yippee!

  12. says

    Of late I’ve been doing taxes myself and I secretly seem to enjoy it! Sure there’s tons of things to understand and learn, but I think it is worth my while!

  13. says

    I always did mine up until the blog with an LLC and all. K-1 forms for limited partnerships, etc. The hassle just wasn’t worth it. I’m glad I did mine for years though so I have a good understanding of the tax system, credits, deductions, etc instead of just taking some guy’s word for it.

  14. Charlie says

    My taxes are pretty simple so I’ve been doing them on my own for the last several years. The software programs are pretty good now too, esp for people like me who have a simple return. I definitely have learned a lot about the various forms by doing it on my own too. I had no idea what was going on my forms when I used to have an accountant do mine.

  15. Mike Hunt says

    When I first started working overseas my company appointed a firm (one of the big 4) to do my US taxes. I had moved overseas in July and was told that by filing an extension and waiting until the following July I could be eligible for the Federal Exemption on the first $85K of taxes (the amount is up to $91.5K for 2010). I thought all was well but then there was a test to check how much income that calendar year was earned in the USA vs abroad, in short I didn’t get the deduction I thought I would so I owed taxes. Because of the extension, there was a penalty and interest charges for this. Of course the firm never advised to pay estimated taxes (though I asked if this was needed and they said no).

    Digging into the forms I found out they made a decision to file form 2555 (exemption on the first 90k of income) or 1116 (credit for foreign taxes paid) when in reality you can file both forms together. Catching this mistake saved me more than $10K in taxes / penalties. I had them do my taxes one more year (correctly, and this seemed to work out better) and after that I began using Turbotax myself, using the previous year as a template.

    Turbotax is very helpful but you have to know what you are doing. There is the actual tax forms as well as the navigator- if you use the navigator alone you don’t get all the right forms filled in so you have to manually go into the forms and fill out the right info. This is now the 3rd year that I am continuing to use the program- so far no audits or queries from the IRS…. hopefully all is well.

    Once you have an idea of the tricks of the trade (meaning which forms to use to optimize your own situation) I think it is ok to do your own taxes. But if you get into running a side business, maybe it is a good idea to engage with a good accountant the first year you file taxes.


  16. says

    I’ve been doing my own tax returns since I turned 18 for the same benefits you listed. I subscribe to the whole philosophy of, “Knowledge is power.” If you don’t know where your money is going how do you ever discuss or plan a budget and/or investment strategies?

    Another benefit that I like that you listed is that you become familiar with the tax code. This way you can actually understand what politicians are speaking about and take tax cuts into consideration when you cast your vote. Too often we hear “cutting taxes” yet it has nothing to do with our specific situations.

    Anyone else here get weird looks from their less financially independent friends when they say that they do their own taxes? The general look suggests an inner voice of, “Don’t you have anything better to do?” Guess not…

  17. says

    I did my taxes online through Turbotax, which I have done for the past 5 years or so. This was the first year I itemized, but it was just as simple as previous years. I admit it took awhile to type in all the necessary to detail to write off capital losses on stock I had sold this past year, but other than that it was definitely worth it. Also, I realized that just using the online version is easier than using a CD….I found 35% off online, by going through the Bank of America portal, it was cheap and easy.

  18. Mike Hunt says

    Forgot to mention I like doing Turbotax with the installed program, so I can play with a few scenarios (like filing married jointly vs separately), I definitely feel better having my info on my computer rather than on a cloud somewhere…

  19. Justin says

    @Mike… why not just make backup, save a printed copy, or save a copy of your return to the hard drive in PDF? Cloud computing is the way to go…I dont see why you would feel unsafe doing this….especially if u are e-filing your taxes anyways. Computers break and can be stolen, hacked,etc. The cloud is everywhere for a reason… in fact I think I may have an idea for my next article on my blog!

  20. Oldfangled says

    We used to do our own taxes (read: hubby used to do them) but the business taxes got too confusing and complicated. We decided to hire someone to do them, and he discovered we’d been paying business taxes we didn’t have to pay! He filed three years’ worth of revisions and we got a load of money back. Plus, it saves a stressed-out hubby and a worried me. I’m okay with paying someone to do them for us.

    • says

      Oh nice! That’s great he filed revisions and you guys got money back! So maybe one should employ a hybrid method of doing one’s own taxes, having a pro do the 4th year and check the past returns?

      I just think it’s important we all are educated on the tax system and our finances!

  21. says

    I’ve been doing my own taxes forever, Sam. I only started using TurboTax about four years ago. I have found the software to be extremely thorough and it lessens the risk of me making a stupid math mistake — which the IRS has found with my returns a couple of times over the years (once in my favor, once in theirs).

    I just finished my taxes using TurboTax Home and Business and it took me about 6 hours. It was kind of complicated with a side business, and stock options to deal with, but in the end it was well worth it.

    All the best,

    Len Penzo dot Com

  22. says

    Interesting to see so many people use TurboTax. I’m looking for 4 winners now, as I’m not sure there are 4 interested parties who need the codes. If so, hit me up on e-mail or Twitter!

  23. Terry Pratt says

    In more than 30 years of doing my own taxes, it has NEVER taken me more than 15 minutes TOTAL to do both my federal and state tax returns.

    Folks, this is not rocket science!

  24. Stephen says

    I enjoyed reading this article since tax season has arrived. I have personally not done my own taxes but I have always wanted to. After reading this I am going to take a crack at it. I subscribed to your newsletter and I look forward to gaining some more knowledge!

  25. jessiejoe1234 says

    This was very helpful. You are also a good writer because I read the entire thing! Lol. But thank you for the cofl fidencw boost and the advice throughout. And I am going to try to do my own taxes this yr. Did them on line last yr but not by myself lol so it will be a little scarier. But I hope all goes good. Have a great day. Keep up the good stuff

Leave a Reply

Your email address will not be published. Required fields are marked *