Talk with those who know me and they will attest: My personality is quintessential Type-A. Both the positive traits (e.g., highly-organized, achievement-oriented, disciplined, competitive) and the not-so-positive ones (e.g., impatient, stubborn, hate to lose). 

One of the ways in which this combo shows up in the admin & operations side of my business is in my weekly and monthly financial tracking system. My process comes in handy when I start preparing for the upcoming tax season, which for me begins in December because my tax deadline is March 15th. Over the years, I’ve learned that I need this runway of time so that I can upload my tax package by February 15th…my CPA’s deadline.  

If you’re wondering why not have a bookkeeper do the data entry, tracking, and review and reconciliation, it’s because I actually enjoy this process. Well, I do when things go smoothly. 

And things were moving along at a nice pace. I was even getting amped about the prospect of actually submitting my package a week ahead of Allen’s deadline!

My Tech Woes

But, something was amiss. 

When I expanded the totals. I realized that five-months of data – that showed up as individual line items in my accounting software – wasn’t being counted in the total for a particular category. Ugh! There goes the gold star for submitting my package early!  

Again, after a frustrating amount of time trying to figure it out, I finally called customer support for help. Before I tell you about that call, let me tell you about the day before. 

I use ClickUp as my project management and CRM tool, and I love that one of its capabilities is creating a whiteboard. I was creating one in preparation for an upcoming call with a client who has a complex business – with at least five different client categories and about the same number of offerings. 

Sure, the whiteboard will reflect the same data as the spreadsheet in terms of which business categories and offers are contributing the most to the company’s bottom line, but it will do so differently. Seeing your data in a mindmap can often provide a perspective a spreadsheet cannot. 

If you are familiar with a mind map, you know that you can add branches from the concept in the middle. Unfortunately, this was not happening properly; it was only allowing me to add three branches and I needed five. 

After a frustrating amount of time, I reached out to customer support. Turns out the problem I was having was not of my own doing. The problem I was having revealed a bug that needed to be escalated to the development team.

When I encounter technology hiccups, I become quickly frustrated. I feel myself devolving into “damsel in distress mode,” something I hate. 

When I’m unable to fix something myself, I feel vulnerable. And I don’t feel in control. All of this sparks questions like, “Why isn’t this working?” Followed by, “What did I do wrong?”

Can You Relate?

Do you ever feel similar sentiments when it comes to money? 

Do you ever encounter financial challenges that spark feelings of vulnerability – that make you feel like you don’t have control? 

When you have financial hiccups, do you ever question how adept you are when it comes to the decisions and choices you make? 

Where do you turn for help when you can’t figure out how to address your financial challenges?

What do you do when things with you and your money seem to be running smoothly, and then…bam! You feel like you’ve hit a brick wall?


As I write, the ClickUp bug is still being worked on. But, they did help me with a workaround in the meantime. 

As for the problem I had with my accounting software, well, that was human error: mine! 🙂 

Imagine my surprise when the customer representative, with whom I shared my screen, quickly found the problem that I had spent about an hour trying to fix? Turns out, for five months I had been assigning the incorrect sub-category. Duh? 

Let’s just say I had mud on my face and apologized profusely because, while I wasn’t rude, I was a tad bit impatient with the rep’s questions. Even though I knew she needed to ask them in order to help me. 

I was also deeply grateful! For her patience with me and the quick solution. 

Your Turn

Maybe your Achilles heel has nothing to do with either technology (like me) or with money (as it is for some). 

But the truth is we all have something that takes us over the edge into territory that doesn’t put a spotlight on our areas of competence and excellence.

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