From Filing My First W-2 by Hand to Hiring an Accountant

It was 1999 when I got my first W-2 from my employer. It showed up sometime around the beginning of March. It wasn’t much money, but it was enough that I needed to file taxes.

This was before being a teenager meant you had access to TurboTax on your phone or laptop. I didn’t make enough money to go pay someone at H&R Block, so I turned to my dad. He wasn’t always great with that kind of paperwork, but he was great at math. He taught me how to fill out the long-form tax return by hand. Most of it didn’t really apply to me since I was a kid living at home, but it taught me something I carried with me for years.

For the next 20 years, I did my taxes myself.

Over time, things changed. I started using QuickBooks for my business bookkeeping. Later, I used TurboTax for a few years. Eventually, I took on doing my own bookkeeping as a small business owner. When I launched my LLC, I handled the taxes myself the first year too.

That experience taught me something important: just because you can do something yourself doesn’t always mean it’s the best use of your time.

This year, I’m using an accountant for the first time, and so far, it’s been great. I still handle my bookkeeping, organize my records, and submit the documentation they need. But they take care of the filing. And honestly, there’s a real peace of mind that comes with having someone who knows the tax code far better than I do making sure everything is done right.

I don’t necessarily love taxes, but I do understand their purpose. I also understand the opportunities that come with being a business owner. The trade-offs are real, both positive and negative. When you work for yourself, if you don’t work, you don’t make money. There’s no sick time unless you’ve built your business in a way that can keep generating income without you. If you stop producing, the business often feels it immediately.

That’s why part of being a business owner is engineering your life and your systems in a way that helps your business grow. Sometimes that means doing things yourself. Other times, it means spending money on the right expert so you can focus your energy where it matters most.

For me, hiring an accountant has already felt like one of those worthwhile decisions. Getting my taxes filed correctly and reducing the stress around it is well worth the cost.

Best of luck this tax season. After all, the old saying still holds true: the only certain things in life are death and taxes.