How To Not Hate Tax Season

It is said that the anticipation of death is worse than death itself. This is certainly the truth when it comes to preparing for tax season, and the actual process of filing your taxes. If this sounds like you, don’t worry!

Most people in America dread tax season, from individuals to entrepreneurs to large business owners. It is definitely not the most wonderful time of the year. 

However, we all have that one friend or colleague who seems to look forward to planning for tax season. You know the one: she’s a boss-babe with everything under control, and her taxes are no different. Which leaves you wondering, “what is she doing right that I am not?!” 

We will explain how to not hate tax season by taking certain steps, and you might even begin to gladly await each upcoming tax season. (No pressure though.)


Be Organized Year-Round

Nothing happens overnight. Therefore, it is imperative that you maintain careful and concise financial records throughout the year. Whether you do this manually, or hire a bookkeeper to do it for you, keeping thorough records can make tax season more like a gentle breeze than a full blown hurricane. 

Keeping a watchful eye on your transactions and financial reports during the year is an essential part of planning for tax season. As an entrepreneur, the last thing that you want while filing your taxes is any surprises that could have been caught beforehand. 

One way to be organized is to keep your personal and business accounts separate. Errors are more likely to occur when you blend funds. Being a boss-babe means acknowledging the fact that your much needed spa day should not be paid for with the credit card you got for your business, no matter how much you want to think that it’s deductible.


File As Early As Possible

Procrastination…. like the struggle is real. It is easy to fall into the habit of waiting until the last minute to start filing your taxes, which obviously does not give you much time to prepare. Thus, you will likely miss tax-saving opportunities, which could potentially make or break your tax situation. This is an easy step to follow in the process of how to not hate tax season.

Filing late or right before the deadline could be the difference between money going into your pocket or money that you have to take out of it. 

I know what you’re thinking. Better late than never, right? I hate to tell you this, but that does not pertain to planning for tax season. Quite the contrary. You can’t predict if your tax return will end up more complicated than you had expected, leaving you scrambling to get certain paperwork submitted or worse, having to hire a tax preparer when you normally do it yourself.

Furthermore, if you file early, you can get back your refund early as well, and put your new dollars to good use. Conversely, if you file late and are slapped with a hefty sum owing to the IRS, you may only have a short window to make the payment deadline. That is not how a boss-babe handles her business.


You May Also Like:

Tax Deduction Checklist


Be Honest and Transparent

It should go without saying that when it comes to taxes, honesty is the best policy. It is always better to produce the correct records and owe a small amount to the IRS, instead of deliberately falsifying documents and then become suspected of tax fraud.

If you make a genuine mistake while filing, and you can prove that your actions were reasonable, you can amend your tax return and could avoid a small penalty. However, if you intentionally do not comply with tax law, then you could be charged a significant fee.

If you are the industrious, amazing boss-babe that I know you are, you know which one of the above scenarios you will fall into. 

Being an entrepreneur isn’t easy, but being honest and transparent can take a great deal of anxiety out of the tax season planning.

Reach Out for Help if You Need it

We can provide you with all the tips and tricks for planning and not delaying your tax filing. We can encourage you to be forthright with your documents and maintain accurate records throughout the year. We can teach you how to not hate tax season.

Nonetheless, it is up to you, you fabulous boss-babe and entrepreneur, to approach tax season like you would approach your next customer, vendor, or business venture.

Without fear. 

And if you’re still nervous – hire an expert! 

Don’t be afraid to turn to someone for help who does this for a living. Employ an in-house bookkeeper and have a good relationship with your accountant or CPA. These professionals are trained to take the guesswork out of your work and make life a little easier when tax season arrives.


Your dislike for tax season can change. You can grow to look forward to it as much as your next hair appointment. You’ve got this.

For more information on how to not hate tax season, contact us below.

 

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