Small investments to make as a 1099

by Dale Davidson March 18, 2026

As a 1099, you have to supply your own company equipment and services.

If you have a frugal mentality, you may want to save small amounts of money on subscriptions and tools and such. For example, instead of spending money on an Adobe Acrobat Pro subscription, you may spend hours trying to find some free online PDF editor, most of which are terrible!

Being frugal can be good, but there is no sense being penny wise and pound foolish.

Here are some items that have saved me time and sanity:

A fast laptop - Working on a slow one is excruciating. If your laptop is more than five years old, consider getting a new one. I just got a 15" MacBook Air. It's great.
Adobe Acrobat Pro - You're going to have sign and edit a lot of PDFs. Just pay the monthly fee to get the subscription.
Microsoft 365 - Forget Google Docs. The government runs on Office Software. Just pony up. It's cheap.
ChatGPT - Get a subscription. It can help you do tedious tasks like draft up language for your sub-contract proposals, do some basic data analysis, re-format your resume, etc.
Freshbooks - I used a spreadsheet and Microsoft Word to track time, expenses, and generate invoices. If that works for you, great, but if I were starting as a 1099 now, I'd just use Freshbooks. It does all that stuff much better than you can and keeps better records. Note, I haven't used this myself but my wife does and it's very simple and easy.

Now, don't worry about getting any of these until AFTER you get your first 1099 gig, but once you get one, spend a little money ($500 - $1000/year on subscriptions and $2500 on a laptop) to make your 1099 life easier.

Want the full playbook? Check out Going 1099.