Stress-Free Tax Season Tips

It’s that time of the year again: tax season. While the fateful day can be cause for fits of anxiety and stress, I've learned that being organized helps to make April 15th less "Week of Total Chaos" and more "Week of Mild Annoyance."

So, how can you, my dear Ambitionista, no longer be at the mercy of a few pages of paper?

I thought you'd never ask.


1. Know Your Tax Status

Life happens. Did you get married this year? (Or, divorced?) Kids enter the picture? Dad move in to live with the family? Did all this happen this year? These might be situations that affect your tax status and make you eligible for more than one. Before you file your return, think about the past life events and any exemptions you may have.

2. Designate a place to keep your documents.

Half the battle of tax season is sifting through all the messy paperwork. So, gather all your receipts, expense forms, sources of income (1098, W-2 or 1099 forms), deductions such as receipts, property tax documents, etc. and records of any investments.

Having one place for all these important documents will save you time and that migraine that seems to hit as April looms closer.

I recommend these apps to help you with organizing:

Expensify: a quick solution to capturing cash expenses, mileage, reimbursements, etc. and importing all card transactions.

Shoeboxed: a ridiculously simple way receipts and create expense reports

IDonatedIt: an app that keeps track of non-cash donations

3. DIY or Hire a Professional?

Are you going to be filing your own taxes this year? If so, it’s especially important to be aware of changing tax laws and to double check information you include -- putting in the wrong social security number can delay the process and even cause you to file your papers late.

If you’ll be hiring a tax professional to do your papers, make sure you contact them at least a month ahead of the deadline. Tax season is huge for them and they get swamped with people who wait until the last minute. So don’t try to call an accountant three days before the 15th -- chances are they’ll tell you to get in line. How to get a good tax accountant? Look for someone who seems like she's got her s**t together < cough cough> and ask for a recommendation. You can go on Yelp (no seriously) or Google and look up 3-4 potential candidates. The best tax accountant is someone who has experience working with people in your profession. So, if you own a restaurant, for example, look for an accountant with a lot of restaurateur clients. Mainly because they can give you all kinds of advice on how to manage your finances based on similar experience.

FYI: While trying to file your own taxes may save you money upfront, a tax professional who does this for a living might save you a lot more money in the long run. If you’re a small business, a contractor or own several properties, you’ll be spending a lot of time sweating the small stuff. A pro, however, gets paid to do these tedious tasks and can help you pay less in taxes or maximize deductions.


4. You Waited Until the Last Minute. Don't Panic.

When filing online, the return won’t be considered on time until the IRS formally accepts it for processing. So, make sure you file at least two days before the deadline. If you’re going the snail mail route, there’s a list of IRS-designated private delivery services to meet the "timely mailing as timely filing/paying" rule for tax returns and payments. These include:

Federal Express (FedEx):
FedEx Priority Overnight, FedEx Standard Overnight, FedEx 2Day, FedEx International Priority, and FedEx International First.

United Parcel Service (UPS):
UPS Next Day Air, UPS Next Day Air Saver, UPS 2nd Day Air, UPS 2nd Day Air A.M., UPS Worldwide Express Plus, and UPS Worldwide Express.

For tax returns to be considered on time, the papers must be postmarked by April 15, 2015. If it comes down to the day-of and there’s no possible way you can get your returns in on time, then file for an extension. The penalty for not filing or getting an extension by the deadline is harsh -- 5 percent to a max 25 percent per month of the amount due on the late return.

We’d love to hear your own tips for making tax season easier. Let us know in the comments!



  • Katie says:

    Oh you’re two months advanced… Well, that’s good, it means you’re setting your priorities right. I’m actually vague about all things tax. I’m just newly married to I have to get this done right away and what better way to learn about it is from my mom and from your blog, thanks!

  • Helga says:

    Oh my… now that you mention it. THIS needs to be the next thing on my To-Do list. thanks for the reminder Heidi!

  • Marielle says:

    Thanks so much for sharing these valuable info Heidi. It’s always a good thing to prepare for that taxing day 🙂

  • Taylor says:

    Glad to stumble on this article. I’m not good in these kinds of planning, taxes and everything, so it’s good that I have something to refer to about taxes. THanks

  • I’m glad FedEx got this delivery covered, thanks so much Heidi for sharing this with us.

  • Darlene says:

    I like organizing things like this, it’s better to go ahead of time than to cram and have a headache in the end. Thanks for sharing those links to the apps that’ll help me organize, it’s really useful and convenient!

  • mistydew says:

    I’ve got a bad experience doing this a year ago, I was kind of distraught because I had to file my taxes at the last minute and when I get to the place, there were a lot of people filing and falling in line, I thought it would never end! So I’m taking chances in hiring professionals to help me with this perennial tax thing. Thanks for the help, Heidi!

  • Jade Collins says:

    I wish I could beat the deadline this year. Thanks for sharing your tips, Heidi, this is very much appreciated. I just got married a year ago and heavily pregnant, so I need all the help I can get regarding the filing of taxes. I wish my husband would do this instead.. (crossing my fingers)

  • Shauna says:

    Thanks for all these helpful tips and guides, Heidi, also the links. What would I do without you and your blog, eh?

  • Susan Armstrong says:

    I love that you are thoughtful to your readers, Heidi. This is also one of the things I look forward to doing and finishing as soon as possible, as I don’t want to beat the deadline and get stuck in filing my taxes. Thanks for the help!

  • Aaliyah Jane says:

    I always wait the last minute when filing taxes. Yes, I know it’s not good. But now that you’re here and you’ve reminded us about this important task, I know I’m going to be an early filer this year. Thanks!

  • Colleen M. says:

    Oh yes, the tax season is here again.. and here I am again cramming up to the last minute. Thanks for this friendly and helpful reminder Heidi!

  • Thanks for sharing those apps for organizing, I really need them this tax season, it’s been a grueling year for me!

  • Olive says:

    Thank you sooo much for this Heidi, you don’t know how much you helped me. I am now fixing and organizing everything for this season and in a few days will be completely done. Thank you!

  • Irene Kira says:

    Is it tax time already? Oh my, how time flies so fast, I thought I’d get to enjoy the last remaining days of February.. I guess I have to make a move now about my taxes. Whew! Thanks!

  • Steffani says:

    Inasmuch as I’d like to do this myself, I can’t because I’m currently out of the country, so I guess I’ll let UPS handle this for me when possible. Thanks for sharing those link suggestions Heidi.

  • Daisy says:

    Thank you very much for this post Heidi, this is exactly what I need right now, especially I’m newly married so me and my husband have a lot to arrange and organize with our tax status. Again, thank you!

  • Princess Lea says:

    I’m glad I got my sister who’s an accountant, she’s promised to help me out with my taxes and finances before the deadline. Good grief! I never thought being newlywed would be this exhausting when it comes to filing and updating.

  • Lalaine Misa says:

    Heidi, dear, you’re a life saver. I’ve been thinking about this the last few weeks and I always forget about it when something comes up. Now I see this, I’ll make sure to make all the necessary preparations and arrangements, pronto. Thank you!

  • Kristine says:

    I’m thinking of using those apps you shared above, I’m big on organizing and I hate it when things like taxes go crazy up to the last minute. Thank you for providing us those steps and tips to work on during the tax season. You’ve been really a great help to us girls and housewives as a whole.

  • Tabitha says:

    I’ve taken up Shoboxed services because I really need help with all my reciepts and taxes and everything. Thanks for sharing their link, as well as the other organizing sites. It’s a Big Help!

  • Vhiel Roman says:

    I can’t believe it’s almost April. I still remember ringing the New year with my then fiance. Now I’m married. And I have to make sure everything else is organized and updated for this tax season. Or does it already count that I’ve just been married for a month? Oh, I need to do this now with professional help. Thanks for all these suggestions honey!

  • Arianne says:

    I’ve received my tax preparation alerts and notice on my mailbox just a few days ago. Oh my goodness, it’s tax season again. Time to re-evaluate all my finances and earnings and such. It’s gonna be a long weekend for me! Thanks Heidi for always being here with your blog which serves as our guide. This is quite overwhelming but really helpful 🙂

  • Zandee says:

    They say there’s always a first time for everything. This is my first time – filing taxes, that is. Last year I finally moved out of my parents’ house and started on my own, opened a small boutique which became my first job, too. So there’s a lot of firsts for me. I never thought filing taxes would be this grueling and hectic too. Thanks for the helpful post!

  • Lorelei says:

    I’ve been firing up my calculator ever since you posted this notice/post a month ago, with a little bum here and there. Oh my, I’m still at my wits’ end with my taxes and refunds. Hopefully within this week, everything’s settled.

  • Claudia says:

    Here’s something that I’d like to share.. if you have concerns with health care and you’re from Cali, I suggest don’t file yet any tax return until you have received the new Form 1095-A from your health care marketplace, such as Covered California. Otherwise, your tax return could be inaccurate and you might face penalties or have to file an amended return. Just sharing..

  • Vivecka says:

    Thanks for all the help, seriously ya’ll have been so very helpful 🙂

  • Natashia says:

    Yes, tax season is here again. Time to gather up those receipts and refunds and stuffs. Oh, it’s gonna be a long month for me!

  • Bev says:

    It’s a month before that dreaded tax deadline and I haven’t even started with my status change yet. Oh it’s gonna be a looong month!

  • Robyn says:

    Thanks for all these links and apps, the’re tremendous help for someone first time tax payer like me.

  • Queenie says:

    I’m glad I ran into this blog and there’s Google too who could help me with this really exhausting month of taxes Thank goodness for friends and bloggers, yipee!

  • Serena Countess says:

    Thanks for sharing this Heidi, it will help us a lot with our taxing system. Very big help!

  • Lian Atwater says:

    Oh thank you for all this tips. April is fast approaching and I’m halfway done with all my taxes and refunds and finances being sort out, plus change in status and everything. Your post just lifted up the stress on my shoulders, thanks so much for this Heidi!

  • Tamiya Rowlands says:

    Eeep, it’s only a matter of weeks before the tax deadline! Gosh, I am so not organized. I need to do this now. Thanks for the app suggestions and the links to where and how to file these taxing papers. You are really a big help. Heidi, Thanks!

  • Zahara says:

    It’s only mere days ahead before the tax deadline. I’m so glad I have already done this and finished everything that needs to be settled this week. And I want to thank you for this reminder/post of yours, it’s so amazing that you always have our back when it comes to things that matter most. Thank you.

  • Susan Armstrong says:

    Hey, it’s me again. Thanks Heidi for this wonderful and helpful post of yours, I was able to fix all there is that needs fixing when it comes to my taxes. THanks a bunch for informing us about this two months before. You’re an angel, dear!

  • Nikki says:

    Hi Heidi,

    Just wanna tell you that this post had helped me a lot a month ago. Now I’m no longer worried with my taxes because I’ve successfully filed and settled everything! Thank you so so much!

  • Aaliyah says:

    It’s me again and I just wanna tell you that this post of your had been of tremendous help with my filing of taxes. I’m now worry free! Thanks

  • Drew says:

    Honey, I’ve been lurking here in your blog and was glad to find this post a month ago. Now I just want to say that you really helped a lot of us for posting this, because we all know that tax day is something we are not prepared to do even though we have a full year to think about this. Again, thanks for all the help!

  • Amanda K. says:

    I filed and paid my taxes at my earliest convenience and I’m glad I did! Thanks for sharing these valuable info, too!

  • loreleichung says:

    I’m so grateful for this post because it helped me a month ago with all my tax issues. Thanks so much!

  • Irene says:

    Just letting you know that you’ve been a big help with this tax-season prep post of yours. Thanks thanks so very much, you helped a lot of young moms like me. Keep it up!

  • Shauna says:

    Hear, hear! I’m so glad everything’s settled right before the tax deadline. Thanks so much for this post, we are all grateful and indebted to you!

  • Francesca says:

    To be honest, I didn’t know anything about filing taxes. Just about five months ago, I got married and neither does my husband have any idea on how to go forth with this tax thing. I happened to be lurking here on your blog and learned that we can hire professionals to do this. Thanks for suggesting that. We got ourselves some help who not only did that taxing work for us, he also guided us through the necessary documents to file so we could do this filing ourselves next time. Thanks for all this wonderful tips, Heidi. Bless you!

  • Lorelei says:

    I survived the tax season! Yes, big big thanks to you Heidi! You have helped me (us) a lot, in more ways that you can imagine. Thanks!

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