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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

Swedish Fika to build relationships

My coffee breaks weren't quite like this but you get the idea. One of the reasons I wanted to go 1099 was because I'm not really a team player. I like to do my own thing. I always rolled my eyes at company parties at social events. They always seem forced and awkward. So going 1099 was right for me. BUT, there is a risk you can isolate yourself. Going solo means you actually need to be more deliberately social than if you work for a bigger company. This WSJ article wrote about a Swedish...

3 days ago • 1 min read

If you want to make it as an actor, LA is probably your best betI live in the Washington, DC area, the center of government and therefore government contracting. There are thousands of government contracting companies and billions of dollars flowing through contracts here. If you want to be a solo 1099 federal sub-contractor, this is the best place to be. But what if you don’t want to live in the DC area? That’s totally okay, but you need to be aware of the tradeoffs. You might have a smaller...

4 days ago • 1 min read

Here's a great Tweet that resonates with my own experience: Sahil Bloom @SahilBloom If you want to win: 1. Be diligent to spot tiny openings 2. Be relentless in diving through them If you think that the opportunities are just going to be staring you in the face, wide open, you're crazy. Every great story starts with a tiny crack. Spot it. Dive through it. 7:46 AM • Feb 6, 2024 123 Retweets 993 Likes Read 68 replies I exploited a tiny opening to get my first 1099 gig. Here were the...

5 days ago • 1 min read

I'd rather be the guy on the left. When you're in a W2 career, it's easy to know if you're making progress. If you are, you'll make more money, get more promotions, and work for companies with better brands. If you are a 1099, a lot of that goes away, and it can be unsettling. So how do you know if you're doing well as a 1099? I haven't been a solo 1099 for a while, but here's how I know I was making progress at the time: Making more money without working harder Finding it easier to get new...

6 days ago • 1 min read

How people might see you as a "rich" 1099... A reader who recently went 1099 e-mailed me this interesting bit of experience he had when he told people he went 1099: "Major lesson point - Some people may be happy to hear you have your own company and things are going good. Some people also might be pissed/jealous/aggressive when they find out. I am not sure it makes sense to tell the world what you are doing and how. I have never mentioned my rate or what I actually make - but most govies and...

7 days ago • 1 min read

I saw this great Tweet (yes, that sounds pretentious) on X that describes different leader/operator combinations: Mark Brooks @markbrooks Visionary, operator, systems thinker, what the heck do these mean? A quick guide to 4 basic work types: 1) My idea / My implementation 2) My idea / Open on implementation 3) Open on idea / My implementation 4) Open on idea / Open on implementation Thread 🧵: 4:28 PM • Jan 31, 2024 13 Retweets 60 Likes Read 8 replies We all have things we care about at work....

10 days ago • 1 min read

Don't start an ice cream stand business in the winter I've been trying to hire this one guy for a while. I haven't been able to do so because the timing wasn't right: When we met initially, I didn't have a spot for him When I did have a spot for him, he wasn't available because he wanted to finish his Master's Degree so he wouldn't have to pay back his company When he finished his Master's, a spot DID open up but the prime filled it before I could get him an interview Now another spot has...

11 days ago • 1 min read

Would you like to join my Alliance Formation 101 seminar Over the past few months I've been networking quite a bit and set up a happy hour with the program manager (PM) for one of my sub-contracts. I did not have a great relationship with the previous PM that he replaced, so this was an opportunity to start fresh. We had dinner and drinks (I paid) and we talked about work, personal backgrounds, experiences, etc. Just getting to know you type of stuff. Now, he's helping me get more spots on...

12 days ago • 1 min read

Entrepreneurs are impatient by nature A reader recently sent me the following article from an entrepreneur/career coach and the lessons he learned from self-employment. 10 Lessons I’ve Learned From 10 Years Of Self-Employment Listicle articles are usually low quality but I related to quite a few of these. In particular: Discipline Trumps Talent Progress Takes Longer Than You Think Things Can Always Be Better. . . And Worse These lessons apply to your solo 1099 federal sub-contractor work. You...

13 days ago • 1 min read

Get on that 1099 lifeboat! A friend of mine works for herself as a 1099 for her previous company (outside of government contracting). She tried negotiating an increase in her rate for the new contract period but was unsuccessful. Her client says she submitted the budget in June for the following year and this year she was asked to cut it down. This is not a good sign for my friend. It's not that my friend's work is not valuable to her client. She easily outperforms the other team members....

14 days ago • 1 min read
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