Awkward 1099 situations


When I was converting my job into a 1099 gig, there were multiple situations that came up where I felt awkward or a little embarrassed.

Announcing my desire to become a 1099

Since I was converting my job, I had to tell my boss I wanted to go 1099. I e-mailed him to set up a meeting and then said something like "my career goals have shifted and I'd like to explore the option of going 1099." Not terrible, but when he said the inevitable "let's revisit this in a month" I said "okay" and then had to awkwardly pester him for the follow up every few weeks. Their stalling made me feel weird.

Negotiating

I pitched maybe $95/hour initially and they came back with $75. We settled on $85 but I awkwardly blurted out I'd like to take Fridays off. It was a weird thing to say because it still made me look like an employee. I could have been more tactful or smooth about it. I still got Fridays off, but it was a little cringe.

Admin ignorance

There were several times when I had to ask the sub-contract administrator at the company what basic administrative things were. I didn't know what the various types of business insurance were or how to format an invoice or understand their role in maintaining my security clearance. As someone who hates looking dumb, it was uncomfortable. This was all in my head though. They didn't care and I got my admin ducks in a row.

---

You're going to feel awkward or uncomfortable many times in your pursuit of a 1099 gig. The fear of being awkward though is worse than the actual experience. Don't let it prevent you going 1099 and improving your life.


If you're interested in learning how to get your first solo 1099 federal sub-contract, check out my book:

Going 1099: How to become a solo federal sub-contractor and gain control of your working life, earn more money and unlock more free time

I'm Dale, the author of Going 1099

Going 1099 is a book that teaches you how to become a solo federal sub-contractor and gain control of your working life, earn more money and unlock more free time. I wrote it because quite a few people have asked me how they can become a 1099. I figured it was best to write a single book that I can send them and that I can share with others who are interested. This newsletter goes out Monday - Friday and covers topics that will help you succeed in starting and maintaining successful 1099 career.

Read more from I'm Dale, the author of Going 1099

You have more time for this as a 1099Source I've worked for myself as a 1099 both before I had kids and after I had kids, so I feel qualified to describe some of the tradeoffs of having kids as a 1099. Advantages: You have more autonomy and control of your schedule. This comes in really handy when you need to come home because your kid is sick or when random stuff pops up. You generally earn more so you can spend some of that money outsourcing things that take time away from your kids...

Move faster than this to impress your clientSource The government is slow. Like real slow. Its employees are slow, and so are a lot of contractors. If you can just be a little faster, you'll look impressive. For example, I just started onboarding onto a new project and the account set up process has many steps requiring annoying phone calls to the help desk and submitting various forms. A normal pace for a contractor is to stretch this out over a week. I did most of this in a day. The client...

I maybe wouldn't gift a sweater at your next meetingSource One of the unintended benefits of writing my book is that it gives me a fun talking point when I'm networking for my business. For example, I met with a couple yesterday who run a small contracting business and I gave them a copy of my book as a small gift, which led to an interesting discussion about why and how they started their own business. I'm opposed to spending too much time on formal marketing activities when you're trying to...