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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.

Featured Post

Parenting your clients

What parenting your client looks like sometimesSource I'm reading a parenting book by the popular Dr. Becky called "Good Inside: A Guide to Becoming the Parent You Want." The core idea is that there are no bad kids, and that trying to manage kids' behavior without addressing the reason why they're behaving in a certain way leads to all sorts of problems. In the book, she emphasizes that it is critical to validate your child's feelings and be in it with them without judgement. "One thing we...

Hardball negotiations....Source On of our projects, the government client wanted to bring on one of our current employees. No problem, we submitted a high but fair billable rate to the prime PM. This rate is just a bit below what my partner bills and is in the same LCAT. The prime sent back a low-ball call counter that was 30% lower. What my partner did at this point was to text the government client and update him on the situation. The client said that in these situations the prime usually...

If you are friends with Maverick, maybe he'll tell you about his MIG encounterSource One of the primes I work with has a director that is good friends with the client. The client feeds information about problems or issues back to the prime before it gets escalated, allowing them to prepare for or address it before hand. Is this shady? No. These are the informal channels of communication you can open up if you have good relationships. I only know about this because I met with the prime program...

Okay maybe Google's cafeteria is a nice perk of W2 life....Source One of the reasons you can earn more money as a 1099 than as a W2 employee is because your personal cost structure are likely way lower than a company's cost structure. As a 1099, you don't need a fancy office, an HR person or middle management, a company Christmas party, boring annual trainings, or free coffee. Okay free coffee is nice, scratch that. But this infrastructure costs money, and while a larger company may need it,...

Me enjoying the workplace dramaSource I just met with a friend who is a deputy PM for a contract. He mentioned some drama with a few of his employees on the contract (HR complaint, desire for recognition, etc.). These employees give him headaches, even though the work is acceptable. He said if they would just do their work and keep their head down everything would be fine. You, as an aspiring 1099, could have an advantage if you're known for simply being a quiet professional. If you just do...

Mr. Miyagi is a 1099 SMESource In my book, I make a point that if you're already pretty senior (management level) at a company, it will be a little tricky to go 1099 (at least, using my methods) as there are less spots for senior people and most companies won't want to bring on a management level person as a 1099. I think if you're at this level, you have a few options. The first option is to fall back to an individual contributor type role. This might mean going back to doing work you did a...

1099 investment strategy resultsSource In personal finance, there is a difference between active investing and passive investing. Active investing involves looking for the next great investment to trade or buy. You research companies, analyze the data, and then buy or sell based on your findings. You are trying to beat what you can get from the broader stock market. Passive investing means putting your money into things like index funds. You basically just buy and hold and try to get normal...

A prime right before they cave and give you a 1099 gigSource The threshold to annoy someone in a professional context is pretty high. You're not going to offend anyone or lose a deal because you send polite follow up e-mails every week. You're not going to be fired if you push back on a bureaucrat saying no. You're not going to be considered an idiot if you ask "dumb" questions. Being slightly pushy or persistent or curious will actually help you get those 1099 gigs. So be slightly pushy. If...

I don't build dashboards, I save livesSource My wife and I are watching a few of the luxury real estate reality shows on Netflix (Owning Manhattan, L'Agence, etc.). When they are showing a home, they try to figure out what is important to the buyer. If they have kids, they emphasize the big yard. If the buyer works from home, they show how a room can be transformed into an office. But if they have a different type of buyer walk into the same house, they will emphasize different things. No...

Sometimes you need an Obama pep-talkSource The hardest thing about going 1099 is not paperwork or negotiation or client work, it's dealing with ambiguity. You're never sure if/when a gig will come through, whether you have the right schools or temperament to become a 1099, or if you can handle going back to W2 work if it came to that. You want to move things forward and aren't sure what the obstacles are. Is an admin person on vacation? Did the PM change their mind? The ambiguity is the...