When to outsource or pay for software

When I was at my last W2 job, I was a junior employee and was assigned some easy but boring and tedious task that involved some data entry and creating some sort of word document template.

I forget what the actual task was but it involved creating placeholders for images in the word doc and some sections for text.

I really did not want to do this so I found someone on Fiverr.com (a place to hire freelancers) and paid him about $100 to do the task for me.


It was awesome! The freelancer did a great job, my boss was happy, and I got hours of my life back. The company was never the wiser...

I paid out of pocket but it was totally worth it.


In my book I have a chapter titled How to operate your business like a minimalist and I recommend that, at least at the start, you do most of the boring tasks like timetracking, invoicing, paying estimated taxes, etc. yourself instead of paying for software right off the bat.

This is because doing it by hand allows you to understand the quirks of maintaining your business. For example, on my project with Leidos, I had to directly enter time in their time-keeping system and it would automatically generate invoices/payments on their system.

BUT, they had their own invoicing schedule that wouldn't line up on a calendar month basis. I would get payments for February 5th - March 5th instead of February 1st - February 28th for example.

Because I was tracking hours in a spreadsheet I could keep track of that manually.

If I was using timekeeping software I paid for and I came across that discrepency, I'd probably have to do things like edit my invoice hours, call their support line to figure out why something isn't working, etc.

It would be frustrating.

Doing it by hand was more tedious but easier in a way.

Now I use timekeeping and invoicing software that is faster and more convenient.


So when should you start paying for software or paying for someone else to do the tedious boring work?

Generally, you should do it when

  1. You have a consistent process for doing it yourself via basic tools (think Microsoft Office tools like Excel and word)
  2. You know the specific features/outcomes you are looking for (e.g., receipt scanning, online categorization and tracking of expenses, etc.)
  3. You estimate you'll get hours of your life back for a reasonable cost

I'm all for outsourcing tedious tasks. You just need to make sure the cure isn't worse than the disease. Dealing with a spreadsheet error of your own making is far better than having to call the Quickbooks customer service line...

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