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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

"Pull the thread" networking

Pulling the thread is better than cold networking When I advise people on how to network and build relationships, I tell them to start with their current network. This means they should reach out to people they already know: friends, co-workers, clients, etc. Maybe not enemies. The reason I do this is because cold networking, while useful, has a much lower success rate. E-mailing 10 people you don't know and only getting one response back (which is normal) can be discouraging. But what...

about 24 hours ago • 1 min read

When art imitates life... You ever feel like your company's performance management plan is nonsense? You set goals and your boss or your peers rate you and then your raise and bonus is based on what they say? Well, your suspicions were correct. It's crap! In this Harvard Business Review article, the author makes the case that everyone rates everyone inaccuraetly. Most HR Data Is Bad Data -- "Over the last fifteen years a significant body of research has demonstrated that each of us is a...

2 days ago • 1 min read

If you expand, you might look like this guy When I first went 1099, I thought there was going to be lots of administrative nonsense to deal with. I was wrong! As a solo 1099, it's actually pretty minimal. There are a few hours required at the beginning of a sub-contract to get things set up, and then maybe a few hours every month to do things like invoicing, setting up a networking coffee meeting, logging expenses, etc. Not a bad pay off for boosting your income 50%! But let's say you get...

3 days ago • 1 min read

Marcus Aurelius imparting 1099 wisdom... Stoicism has had a resurgence in the last decade, and for good reason: it's a powerful tool to manage your mental state and well being. Marcus Aurelius, Roman emperor from 161-180 CE, is a modern "influencer" due to his journal, which contained a log Stoic lessons he applied to his pretty tough day job. Meditations: A New Translation Here are some Stoic gems from his meditations that apply to your 1099 journey: -- "Love the discipline you know, and let...

6 days ago • 2 min read

What happens when you're waiting on your one 1099 lead... Source: https://www.meme-arsenal.com/en/create/meme/4083609 I support a People Analytics team, and one of the metrics the team looks at is the hiring conversion rate. You can calculate this a few different ways, but one way is to count the total number of candidates who accepted your job offer, divided by the total number of applicants. If there were 100 applicants and 10 accepted a job offer, the hiring conversion rate is 10%. [Note:...

6 days ago • 1 min read

We need a mug that says "slow down." I just finished Cal Newport's new book called Slow Productivity: The Lost Art of Accomplishment Without Burnout. Slow Productivity: The Lost Art of Accomplishment Without Burnout Cal argues that hustle culture and the world of "pseudo-productivity" have left us de-energized and demoralized and that instead, we should adopt what he calls "slow productivity," for which he has the following defintion: "A philosophy for organizing knowledge work efforts in a...

7 days ago • 1 min read

You need to learn to sneak away from yourself There's a great chapter in the book, The Art of Gig that describes the phenomenon of "sneakoffproofitis." --- "The problem is, as a free agent, you are your own boss, and you’re likely a bad boss, unable to relax, and driven by fretful anxiety about lining up the next gig. That would be bad enough, except that you’re also an omniscient bad boss. You know all your own tricks and nothing is hidden from you. You can’t sneak away from yourself. You...

8 days ago • 2 min read

I wouldn't be so brazen about taking time off but you get the idea There's a great quote by Amos Tversky, a famous research psychologist who explored human decision-making: “The secret to doing good research is always to be a little underemployed. You waste years by not being able to waste hours.” Americans love the idea of being busy. It's a badge of honor to respond with "oh man I am swamped" when someone asks you how you're doing. But I've never been attracted to the busy state. I like...

9 days ago • 1 min read

You want the clients BEGGING to work with you There is a popular YouTube entrepreneur named Alex Hormozi who ran and sold a successful gym business, gym software business, and now owns a sort-of private equity company. He is a cheesy influencer type (which helps him cultivate deal flow for his company) but his book, $100M Offers has some gems in it. $100M Offers: How to Make Offers So Good People Feel Stupid Saying No The core idea is that in business, instead of starting with what you're...

10 days ago • 1 min read

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...

13 days ago • 2 min read
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