Learning Lessons from Tax Season: Planting Seeds for 2020

Written by Chelsea Francis

It’s easy to look at this tax season and feel like a failure. If you’re the kind of person who has everything figured out financially, I am honestly so proud of you I could cry. You deserve a Beyonce world tour sized crown for your achievements honestly. We all think so. But this piece may not be for you. If you’re like the rest of us, your skill level with handling money falls somewhere short of having it all figured out. This often means that tax season can leave you feeling like a complete and total failure. It’s certainly left me feeling that way before. So if you find yourself trying to sort out what to do next, then I thought I might help.


One of the things I am most passionate about in life is teaching people that there is a massive wealth of knowledge waiting for you when you feel like you’ve failed. But because of reasons outside of our control, most of us have a lot of our worth tied up to our successes that make failures feel soul crushing. When your soul is crushed, it’s hard to take a critical approach separate from the negative emotions that the fear of failure often produces.

Here are a few things that will make your next financial year go a little more smoothly.

1. Evaluate.

Look at what you’ve accomplished this year! Sure, maybe you didn’t prepare as much as you could have but right down all the things you did well. On a separate sheet of paper, write out what you need to improve on. Take the top three things and start working on them. Your future self will thank you.

2. Get organized!

I use the Tiny Scanner app to scan in all my receipts and I organize them in a Dropbox folder. I keep the physical copies in a cute box in my office so I know where they are for when it’s time to assess write offs. I use Freshbooks to keep track of the money coming + going. And I use some Google sheets to predict what next quarter will look like. Whatever tools are in your toolkit, use them!

3. Hire an accountant.

Trust me. Life will be better if you have someone to answer your financial questions, and give all of your nice and organized financial tools too. It’s their job to get you the biggest tax break possible, and oftentimes that means they pay for themselves.

4. Be proactive about taking care of yourself physically + mentally.

Now that you’ve hired an accountant we can switch gears out of survival mode. You think and make decisions better when you’re taking time for yourself daily, weekly, monthly and yearly. Don’t fight me on this. Schedule time that’s just for you and it will make everything else go smoother.

5. Schedule a regular money making field day.

One of the greatest gifts I have an entrepreneur is that I can make money. I don’t have a boss who is waiting to write me a paycheck. I write my own. I function much better in my multiple roles if I know this as a fact, and not some far off nicety. So once every month or so I set down and I try to make $1000. I know it sounds insane, but I’ll write $1000 on a piece of paper and figure out ways to make it happen that day. And most of the time, I am successful at it. I track down leads that I haven’t heard from. Sometimes I sell camera equipment. Sometimes I look at my inbox and take a project I may not have otherwise because it’s easy and there’s money attached to it. Sometimes I email friends and tell them I’m trying to meet a goal, and ask if they’ve heard of anyone needing a photographer, a writer, or a speaker at an event. I don’t let myself believe failure is an option because even if I don’t hit the goal, the concentrated effort of attempting to make money yields results. This might look different for you, but I think it’s worth a try if you work for yourself.  

6. Get educated about money management.

My go to site to read about financial management is Bravely. Bravely is an online community that gives self identified women access to resources that help them bridge the gap between where they are and where they want to go financially. I love reading about what famous people think of money on WealthSimple. I really love this piece about Jon Hamm. I also love attending events and talking to people about money. One of the best events I’ve ever attended and eventually got to be a part of is the Freshbooks #IMakeALiving event! And if you’re in Austin, you’re in luck! They’re coming our way April 17th and you won’t want to miss out! Click here to grab your ticket.


This blog is sponsored by Freshbooks, though all the thoughts and opinions expressed in this post are those of the writer and approved by Pass/Fail. Freshbooks is a cloud based small business accounting software. Send invoices, track time, manage receipts, expenses, and accept credit cards. They make managing every aspect of your business easier, whether that’s project workflow, billing, or following up with clients who haven’t paid you yet. Pass/Fail readers can get two months free to give it a try by clicking here.

Chelsea Francis