A file folder box filled with empty file folders

I’ve spent the last week or so cleaning, purging, and reorganizing my office. I had encapsulated myself in a micro-hoarder situation in the shed which made it difficult to get focused. Clutter, as I’m learning, is adversarial to my distractible brain. One task that’s been looming over my head was this box of file folders.

This box of file folders was a collection of all expenses and tax documents from the years 2012-2016. And I mean everything. Every gas, electric, internet, and credit card bill that came to my house. Every business expense. Every health expense. Every mortgage payment. The reason I hoarded all these documents? Self-employment. All those numbers factor into my tax bill every year, so I kept every physical document that was relevant. America glamorizes starting your own business as “entrepreneurship” or “making your own hours” but it’s a lot like paying a lot of extra self-employment taxes for the privilege of meticulously holding on to and organizing your literal garbage.

But, because my accountant said I need to keep five years worth of documents I now get the privilege of shredding each of them in my little shredder (that I still have the receipt for, natch 😉).

Shredding this box of documents was an emotional journey.

  • 2012 was the year Paravel did the Microsoft homepage. Business was going good for Paravel, but this was like strapping ourselves to a rocketship. It wasn’t buy a yacht money by any means, but life-changing in different and intangible ways.
  • 2013 we found out my wife was pregnant after years of trying. Prenatal hospital bills filled this year’s folder as well as the receipt for the cash payment of $5,300 for the birth of my son because my insurance was so bad that was the cheapest option.
  • 2014 also filled with hospital bills for the new baby’s checkups. Business receipts for conferences in other countries began to show up. I built my first shed at my old house. This was also the year my accountant ghosted me and I learned they basically guessed a number on my 2013 taxes. Yikes.
  • 2015 oops, pregnant again. More hospital bills. More cash payments for births. This was also the year of #davegoeswindows, so lots of receipts as I navigated that experience.
  • 2016 less hospital bills, more computer parts, but our life was beginning to stabilize as we adjusted to our new life with our two kids.

From entering a new era of business, to having our two kids, to colossal tax liabilities, to changing my entire workspace and workstation; this box was a major arc in my (and my family’s) life. There were a lot of memories living inside that box of mundane files. There was also a lot of garbage. Two whole entire compost bins full of shredded document garbage, to be exact. I’m thankful for the memories and the opportunity to reflect, but glad I eradicated those little paper horcruxes.