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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.

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Featured Post

Making friends at work

Ahh non-diverse workplace friendships.... The Wall Street Journal published an article that made the claim that Gen-Z are negatively impacted by remote work because they don't get to make friends. What Gen Z Will Lose if They Don’t Have Friendships at Work -- "The rise of remote work has upended all that; the less time we are in the office, the less time we have to form and cement the bonds of friendship. That’s true for all remote or hybrid workers. But the impact is being felt most strongly...

1 day ago • 2 min read

From Art of Gig Volume 1: https://www.amazon.com/Art-Gig-1-Foundations/dp/1959228005 You can only prepare so much. You've done all the research. You have savings. You know you can get a back up job offer. You have great client relationships and technical skills. At some point you're going to have make your move. This might mean telling your boss you can only stay if they keep you on as a 1099. It could mean asking a potential client if they'd like to work with you, and if so, ask for an...

3 days ago • 1 min read

Sherlock Holmes was a 1099 I'm always surprised how few of my friends, who are all smart and educated, don't read on a regular basis. I'm not even a heavy reader, but I probably go through a book per month. This helps me with my writing and thinking and also gives me the fun party trick of being able to annoy others with miscellaneous facts that challenge their world view. Similarly, I'm always a bit surprised by how little research government employees and contractors put into solving work...

4 days ago • 1 min read

I love a good cubicle hammock nap... If you've managed to go 1099, congratulations! You're probably making more money and/or have more free time. Here's what I'd do with those assets: If you don't have it, build a year of emergency fund savings and then invest more Take either Friday off or regular half days during the week. This is particularly nice for running errands without crowds. Hang out with the wife and kids Level up on the vacations (add more convenience, luxury, etc.) Work on a...

5 days ago • 1 min read

Change is not for the weak! It's hard to leave a good thing. My wife and I had decided to move to Portland, and then at the last minute (well, last few months), decided to extend our time here in DC by six months. One "rational" reason to stay was to take advantage of our health care network for the birth of our second kiddo in August. But really I think all the fears about losing our career options, friends, and social network bubbled to the surface. These are real concerns. But in...

6 days ago • 2 min read

V1 of Grammarly I'm not a detail oriented guy. You can probably tell by now. Each newsletter I send out has at least three typos. My book probably has hundreds. The thing is, I don't have the patience to review my work line by line for typos. I find it tedious. In school and in my corporate jobs, this was considered a great moral failing and I've always felt a little bad about myself for not doing better. BUT, I've learned feeling bad about it is a waste of time and energy. You have a few...

9 days ago • 2 min read

Don't be the nerd in the lab coat Most government contractor job descriptions list skill and experience requirements. 10 years of work experience 5 years of SQL 3 years of budget or financial management experience Expert level Python developer Familiar with Node.JS If you have the listed skills, a recruiter or PM will be interested in talking to you. But what the client cares about is results. They do not care at all what skills or experience you have. Side Note: If you're not delivering...

10 days ago • 1 min read

Be a 1099 tortoise, not a guy in suit springing on a treadmill I'm in a rush to be successful. I'm not, by nature, a fast paced guy, but when I want something, I want it to happen quickly. In the world of government contracting, things generally don't move quickly, which is frustrating. On occasion, things move quickly, but progress is usually made in spurts. Nothing happens, nothing happens, then a lot happens all of a sudden. What I've been [attempting to] teach myself is to enjoy the ride...

11 days ago • 1 min read

The proverbial lemonade stand can lead to bigger opportunities I recently discovered a cool podcast (well, cool if you're into government contracting) called Game Changers for Government Contractors. There is one episode where the host interviews a GovCon Founder who used "micro-purchases" to get his business off the ground. Game Changers - Creating Your 10k Micro Purchase Offer What is a micro-purchase? Micro-purchase Basically, it's any government government purchase under $10,000. While...

12 days ago • 1 min read

This negotiation went very wrong... A bunch of people ask me what they think they should charge for a billable rate if they go 1099. Their thought process is usually "Well I make $100,000 and it probably costs my company 30% more in benefits so that's $130,000, and they're probably making 20% profit so that means they bill out $162,500/year which comes out to a billable rate of $87/hour if there are 1860 billable hours per year. This means I should charge them $80/hour so they make a small...

13 days ago • 1 min read
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