About the book



What this book is about

What's in the book

Why does this book cost $100?

All the reasons you shouldn't buy this book

Purchasing details

Reader feedback

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What this book is about

This book will help current employees of federal contractors become independent 1099 federal sub-contractors who earn more money and have more autonomy and 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.

I also didn’t find many good resources about becoming a solo 1099 federal sub-contractor online. I found generic business books/articles and lots of administrative resources about getting federal contracts but almost nothing tactical or specific that would help my target audience: (disgruntled) federal contractor employees who want to work for themselves.

You can check out the table of contents and the high-level chapter summaries below for a more detailed description of what is in the book.

What’s in the book

The book is a little over 60,000 words and around 120, Letter-sized (8.5” x 11”) pages.

Chapter 1 - How I became a 1099 federal sub-contractor
I share my own experience as a 1099 federal sub-contractor and include details like how I made the decision, how I convinced my company to keep me as a 1099, and how much more money I made and how I took Friday’s off for a while.

Sub-sections:

  • My background
  • Assessing my value to the client
  • Figuring out if I was replaceable
  • Assessing the financial return
  • Pitching the plan to my boss
  • The primary focus of this book
  • Doing the (boring) paperwork
  • Maintaining your security clearance
  • Operating your 1099 business
  • Increasing your income
  • Figuring out if 1099 is right for you

    Chapter 2 - Understanding 1099 federal sub-contracting and why it exists
    If you are going to be a federal sub-contractor, it’s important to understand what it is and the basic economic/business incentives around it. I’ve heard from a few folks that companies only want W2 employees and while there is some truth to that, there are reasons why they take on 1099s and sub-contractors. If you know what these reasons are, you can use them to your advantage.

    Sub-sections:

    • What the heck is a 1099 anyway?
    • 1099 is shorthand for independent contractor
    • What is sub-contracting?
    • Federal sub-contracting
    • Economics of federal contracting
    • Why do companies hire 1099s or sub-contractors?
    • Why does any of this matter?

      Chapter 3 - The rewards and risks of 1099 life
      This is the chapter that describes some of the rewards and perks of going 1099, but most importantly, the risks. Everyone likes to talk about the fun parts about working for yourself but you need to have a realistic understanding of what can go wrong. I was out of work for a year due to security clearance issues and COVID, which costed me about $200k in revenue.

      Sub-sections:

      • The rewards of 1099 federal sub-contracting
      • The unique elements of 1099 federal sub-contracting compared to other businesses
      • The risks of 1099 federal sub-contracting
      • Reasons you shouldn’t become a 1099
      • Making the decision

        Chapter 4 - Is your non-compete enforceable?
        I haven’t personally signed a non-compete but the issue pops up on occasion. This chapter gives you some basic information on how to assess whether your non-compete is enforceable if you do go 1099.

        Sub-sections:

        • What are non-compete agreements?
        • Are they enforceable?
        • What this means for you 1099 ambitions
        • Non-solicitation agreements
        • Bottom line

          Chapter 5 - How to model and compare your potential 1099 income to your W2 compensation
          This chapter will help you figure out how much you will need to earn as a 1099 to make it financially worth it to you. It will help you avoid a scenario in which you charge too little and you end up taking home less money than you would as a W2 for the same amount of work.

          • Apples to apples: make sure you compare the right numbers
          • Baseline your W2 income (W2-APPLE)
          • Model your 1099 income (1099-APPLE)
          • How to determine realistic 1099 numbers
          • Determine which scenarios are worth it

            Chapter 6 - Method 1: How to convert your job into a 1099 gig
            This is my most recommended approach to going 1099. The chapter will guide you through the steps to converting your current job and position as a W2 employee into a 1099 role. This is how I got my first 1099 project.

            Sub-sections:

            • Convert your job into a 1099 role
            • Who this method won’t work for
            • Step 1: Assess your value
            • Step 2: Gather contract information
            • Step 3: Model your projected financials
            • Step 4: Make sure you have at least two months of living expenses saved
            • Step 5: Initiate the conversation(s)
            • Final thoughts about the 1099 job conversion method

              Chapter 7 - Method 2: How to network your way to a 1099 gig
              This method details how you systematically reach out to people to get to a program manager that can bring you on as a 1099. Don’t worry, there are no business cards or networking events involved. Instead, e-mail, phone calls, coffee meetings, and warm introductions are the key elements to this approach.

              Sub-sections:

              • Network your way to a 1099 gig
              • Identify your target opportunities
              • Don’t cynically use people
              • Avoid networking groups and events
              • Networking goal
              • Start with your current network
              • Cold networking
              • What happens when you meet with a PM?
              • Final thoughts about the 1099 networking method

                Chapter 8 - Method 3: How to “apply online” for 1099 jobs
                This method is about using the traditional online job application to get a 1099 gig. It basically involves using the exiting W2 recruiting process to land a conversation with a program manager who has the authority to bring you on as a 1099.

                Sub-sections:

                • 1099 job hunting technique
                • Make sure your resume has a narrative
                • How to find job opportunities ONLINE
                • Maximize application efficiency
                • Get past the recruiter
                • Maximize the hiring manager or program manager interview
                • Negotiate

                  Chapter 9 - How to set up your business like a minimalist
                  This chapter describes the administrative steps you need to take to set up your 1099 business. Most importantly, it describes what you DON’T need to do so you don’t waste your time on non-essential admin stuff.

                  Sub-sections:

                  • Rules for setting up your business
                  • Incorporating your company: necessary or not
                  • Why register an LLC vs a S-Corp or C-Corp?
                  • How to register an LLC
                  • Register for an employer identification number (EIN)
                  • Register for a DUNS number
                  • Register in SAM.gov
                  • Business bank accounts and credit cards
                  • Business website, e-mail, and phone
                  • Keep it simple

                  Chapter 10 - How to complete the paperwork for your first 1099 sub-contract
                  This chapter describes how to complete the paperwork for your first 1099 sub-contract. It can be intimidating and confusing at first glance. My first contract was easy but my second one looked way scarier. It’s actually not scary at all and it is basically the same for most companies. This chapter guides you through the different parts of the paperwork.

                  Sub-sections:

                  • The sub-contract
                  • General guidelines for filling out the sub-contract
                  • A few tips and recommended purchases
                  • Proposal cover letter
                  • Vendor profile
                  • W-9 tax form
                  • Non-disclosure agreement (NDA)
                  • Rate sheet/price proposal
                  • Representations and certifications (again)
                  • Insurance
                  • Statement of work (SOW)
                  • Invoice and payment terms
                  • Other paperwork
                  • Small price to pay for big benefits 81

                    Chapter 11 - How to operate your business like a minimalist
                    This chapter teaches you the basics of time-keeping, sending invoices, paying taxes, and the essential “operations” type of work you are on the hook for as a 1099. The focus is on simplicity and doing only what is necessary.

                    Sub-sections:

                    • Time-keeping
                    • Invoicing
                    • Expense tracking
                    • Taxes
                    • Don’t stress

                      Chapter 12 - How to manage your security clearance as a 1099
                      If you have a security clearance, your value as a 1099 goes way up. It is prudent to make sure you do what you can as a 1099 to maintain your clearance. I share the lessons I learned the hard way about keeping your clearance active.

                      Sub-sections:

                      • Security clearances for 1099s
                      • Security clearance basics
                      • 1099 security clearance scenarios
                      • 1099 security clearance lessons

                        Chapter 13 - How to increase your income as a 1099
                        Like most people, you’ll want to earn more money as your progress in your 1099 “career.” This chapter covers a few different ways you can do that in subsequent contracts.

                        Sub-sections:

                        • How to increase your income as a 1099
                        • Increase your rate
                        • Firm-fixed price arbitrage
                        • Take on multiple projects

                          Chapter 14 - How to be a consultant and not an employee
                          As an employee, you might have gotten used to having a boss that told you what to do and when to do it. As a 1099, you’ll add more value if you act more like a “consultant.” This means you should be very client/customer focused and figure out what their needs are. I’m not the best consultant but this chapter includes a few tips and techniques that I have used that you can use too.

                          Sub-sections:

                          • Ditch the employee behavior; become a “consultant”
                          • Dale’s random collection of consultant tips
                            Chapter 15 - 1099 wrap up thoughts
                            This chapter includes a few thoughts I have about the 1099 life.

                                Why does this book cost $100?

                                This book is expensive when compared to a "normal" book, but here are the ways it provides value that makes it worth it:

                                • It will save you a ton of time researching stuff online. Your time savings are certainly worth more than $100
                                  • Example: You could spend hours and hours trying to sort out how you will handle health insurance as a 1099 or read my chapter about factoring in you costs
                                  • Example: You could decipher various articles about your security clearance on government websites OR just read my chapter about security clearance
                                • The book provides knowledge based on experience, not just textbook knowledge
                                  • Example: I lost over $200,000 in potential revenue by not planning my projects correctly. You can learn from my mistakes.
                                  • Example: I tell you what you need to prioritize when going 1099. If you just research online, you'll think you should focus on paperwork and administrative issues.
                                • The book will help a BUSY person who wants to go 1099. If you're in a grad program or work full time or have kids, you can use this book as a reference to look over as you have time. You don't have to do it all at once
                                  • Example: If you only have 30 minutes a day, you can read a chapter or even a few sections in those 30 minutes and get a ton of value. Each section has a purpose.
                                • The book is like having a 1099 friend (no, not a contractor you hired to be your friend) who is interested in helping you succeed
                                  • Example: I write in plain language in a conversational tone. It's as if I were in the room telling you how to write your e-mail to your boss saying you want to go 1099.
                                • The book will help you earn AT LEAST $20,000 more per year AND/OR get you a better lifestyle
                                  • Example: On my first 1099 project, I converted my job and earned about $25k more per year while taking Friday's off.
                                  • Example: I no longer have a boss and have to do performance reviews or other employee nonsense.
                                  • Example: In 2022, I earned around $375,000 working less than full time. Best case as a W2 for my skill set I would earn about $200,000 working at a non-government tech company (I received a job offer to test the market).

                                If you are serious about working for yourself as a 1099, this book should be a no-brainer. You probably spent more than $100 on a single Uber Eats order (stupid delivery fees!). This book will help you go 1099 and give you the financial  means to order even more delivery! Or even better, get you to that dream vacation in the Maldives without worrying about how much vacation time you have.

                                If you have questions about how the book will help you in particular, please e-mail me at dale@1099fedhub.com.

                                All the reasons you shouldn’t buy this book

                                I will not be offering refunds for this book because it is a pain in the butt logistically so I want to be totally upfront and list all the reasons why you shouldn’t buy this book. That way you can make an informed decisions for yourself BEFORE you buy it.

                                • You think this book will make you rich.
                                  • It will not make you rich. It will help you increase your income by 25% to 100% as a 1099. That is a lot of money but not “overnight millionaire” rich.
                                • You are not currently an employee of a federal contractor
                                  • This book is targeted towards people already working in the industry. In theory, you could use parts of the book to help you break into the government contracting world as a 1099 but I’m not sure why you would want to.
                                • You are too junior or too senior in your current role as a W2 employee
                                  • There is a certain sweet spot in terms of experience.
                                  • If you are a new college graduate it is unlikely you have the experience/skills to pull off 1099 work right away.
                                  • If you are too senior and manage people it’s much harder to find gigs like that as a 1099. Most 1099 roles are individual contributor roles.
                                • You are very risk averse
                                  • Going 1099 adds some risk to your working life. If that makes you very uncomfortable, don’t buy the book.
                                  • Quick test: How do you feel about going 3 months without income? Is that worth it for the chance to earn 25% - 100% more than you do now? If no, don’t buy this book.
                                • You are very socially awkward
                                  • If you break out into sweat any time you have to meet someone new or have a slightly uncomfortable conversation, it is going to be tough to become a 1099 because you will have to talk to more people than you normally would (program managers, clients, recruiters, etc.).
                                  • I’ll caveat that if you have an ultra-rare and valuable skill, you can probably get away with being a weirdo.
                                • You want to build a government contracting business with employees
                                  • This book will not help you build a business with employees and government contracts.
                                  • I have a few employees and becoming a solo 1099 is a good jumping off point to building a company, but I don’t have enough expertise or success growing a company to help you.
                                • You think this book will dramatically change your life
                                  • This book will help you earn more money and gain more autonomy in your working life. However, your day-to-day working life will look pretty similar to your life as an employee (though with less company BS).
                                  • This is not one of those broad business/self-help books that is 99% inspiration and 1% practical details. This book is basically 100% useful information about becoming a solo 1099 federal sub-contractors.
                                • Things like typos ruin books for you
                                  • I guarantee you there are typos and other errors in the book. Sorry, I didn’t catch them all and my attention to detail with things like that is pretty bad.
                                  • If you’re pretty OCD about it and are one of those people who think typos mean the person is not credible, then definitely don’t buy the book. You’ll go crazy and be trying to negotiate your 1099 contract and won’t be able to remember the steps because I spelled negotiation "negoshiashon."
                                • You’re not willing to wait 3-4 weeks for the book
                                  • I’m using a print-on-demand service so I don’t have to stockpile 1,000 books in my basement. When you place an order, it will take 3-4 weeks to print and ship it to you directly.
                                  • Update: If you'd like, send me an e-mail (dale@1099fedhub.com) after you place your order and I can send you a PDF version of the book. I just ask that you don't post it on the internet.

                                Purchasing Details

                                • Shipping
                                  • Shipping is included in the price and the book should take about 3-4 weeks to reach you. Each book is printed on demand which is why it takes so long.
                                • Digital copies
                                  • If you'd like, send me an e-mail (dale@1099fedhub.com) after you place your order and I can send you a PDF version of the book. I just ask that you don't post it on the internet.
                                • Refunds
                                  • I am not offering any refunds unless something totally weird happens like the book never arrives or something. Too much hassle.  That being said, if something weird does happen, let me know at dale@1099fedhub.com.

                                Reader feedback

                                From JB

                                1) What was the obstacle or hesitation that would have prevented you from buying Going 1099?
                                Time frame for receiving the book, cost, or close colleague who is working as 1099.  However, the digital copy has alleviated the time crunch; and in some ways, has allowed for easier navigation for the sections of interest.  I'm finding the cost is miniscule relative to the rest of my business costs (registration fees, email costs, accountant, insurance, etc) and has saved me hours trying to find the same material on my own.

                                2) What did you find as a result of buying the book?
                                Only a few materials out there for this niche and this has been the most synthesized I've found.  Loved the concrete examples and tactical information to help with 1099 related conversations like rate negotiation, talking with prospective PMs, etc.  The book has also changed my perspective.  I view my role as a consultant instead of an employee. The cost has definitely been worth it and I have already used some described techniques to find a good rate range.

                                3) What specific sections/information did you like most in Going 1099?
                                So far the most useful sections have been how to determine the consulting rate range, the methods to get 1099 gigs, the content related to setting up the business with the government/contractors (DUNS, SAM.gov, etc).

                                4) What would be three other benefits to buying the book?
                                1. Everything you need to get started.
                                2. Answered questions you didn't know you should be asking.
                                3. Demystified some of the pieces that I had no clue about like sub-contracting paperwork, government registration, managing security clearances, etc.

                                5) Would you recommend Going 1099? If so, why?
                                Yes, I wasted hours searching for answers when I could have just read the book. You'll save time (money) and have better keywords, lexicon, etc, when performing research as well.

                                6) Is there anything you’d like to add?

                                Dale is helpful and responsive to communication

                                From Trish

                                Note: Trish is NOT a government contract but had useful feedback as someone who is starting her own solo business. She is also a friend of mine so I gifted her a copy.

                                1) What was the obstacle or hesitation that would have prevented you from buying Going 1099?
                                Perhaps it's just the subtitle. I found the info in the book useful even if I wasn't joining the federal workforce. I think if it was marketed towards individuals who were interested in becoming freelance professionals/contractors in any field I would have considered it.
                                 
                                2) What did you find as a result of buying the book?
                                Firstly, thanks for the copy! It was useful to have around the house. It was like having a buddy who knew more than I did about the 1099 space. If I thought I had forgotten something I could refer to it instead of going down the search engine rabbit hole.

                                3) What specific sections/information did you like most in Going 1099?
                                Everything except Chapters 2, 4, and 12 were useful to me as someone who was new to contracting but not intending to work as a federal contractor. I especially liked sections that went through necessary paperwork, and the later chapter about switching from an employee to a contractor mindset is something I still think about.

                                4) What would be three other benefits to buying the book?
                                I like that it's plain language - it's a benefit you don't know you want until someone hits you with jargon and pedantry. It's also sleek and easy to navigate so it's a good reference guide to keep (I'm still in the moving mindset so overly bulky things are beginning to upset me). I also think most of the information is evergreen, although I do foresee updates in the networking sections.

                                5) Would you recommend Going 1099? If so, why?
                                I would! I have, haha. To anyone intending to add contracting to their life, either as a full-time job or as a supplementary gig. It's especially useful to people who have only ever worked as salaried/hourly employees and have no context for this other economy, like myself. And honestly, as someone who's fervently anti-MLM, I really think this book would empower so many people who want the flexibility and income promised to them in an MLM. They'd see there's another way that's legit and actually uses skills they already have.

                                6) Is there anything you’d like to add?
                                I'm very much a text person and don't need pictures or diagrams to learn. I imagine you're similar? This puts us in the minority though, and my time as a teacher has taught me that most people like pictures whenever there's a "how-to" or "good/bad examples" section. I understand this might be costly/difficult. Additionally, marketing it outside federal contracting, whether splitting the book or just changing the title, might snag you a bigger audience. Lastly, some people like anecdotes from other individuals because the author's ethos, while powerful, is always a little suspicious. :)

                                 

                                From Jordan

                                1) What was the obstacle or hesitation that would have prevented you from buying Going 1099?

                                I wouldn't have bought it if I was uncomfortable with the stigma surrounding 1099 work.

                                2) What did you find as a result of buying the book?
                                Actionable steps for building the RELATIONSHIPS and the perception of being an expert in order to gain leverage.

                                3) What specific sections/information did you like most in Going 1099?
                                I particularly enjoy the sections that help to find the price you should bill per hour.

                                4) What would be three other benefits to buying the book?
                                • Forming relationships with individuals of import
                                • Placing a more accurate value on one's professional time
                                • How to use psychology and leverage to get what you deserve
                                5) Would you recommend Going 1099? If so, why?
                                I would recommend it for a specific personality type. Someone who doesn't suffer from Stockholm Syndrome.

                                6) Is there anything you’d like to add?
                                This is an incredibly specialized book but also contains lots of gold that is applicable in the general workplace throughout ones career. Maybe a title mentioning WHY someone should go 1099 as well as HOW to do it could attract some fence sitters who are deathly afraid of freedom.

                                From Chris L.

                                1) What was the obstacle or hesitation that would have prevented you from buying Going 1099?

                                Just the pure fact of googling and seeing the book show up in a random fashion. However, I'm always willing to shell out a few bucks for something that might be the edge I need to help me jump start my idea or path. So it's really a matter of how tight the person is with their wallet I would guess. The original article that you wrote took my fears away and that's what made me agree to purchase the book. I was like, well that article made sense and knowing already what I know about contracting, nothing smelled funny, so it all checked out in my mind as a valid article on the topic. So, I then I felt, what do I really have to lose by buying it, nothing. If anything, I end up knowing more and more about the direction I'm interested in. 

                                2) What did you find as a result of buying the book?
                                A fascinating story of your experience that covered the pitfalls/trials in realistic fashion. I think that's what I learned the most, because starting a business is one thing and fairly easy, but the important items like your clearance, relationship building and communication/negotiations and information gathering to be truly successful are so important to track and maintain above all else.

                                3) What specific sections/information did you like most in Going 1099?
                                The laid out business documents, like expense sheet columns or the list of what id numbers to obtain like DUNS, etc. I liked the order of events for starting the business to help with my own checklist of items to organize and follow through with. Since I've started going through this book, I've taken breaks here and there to do my own research and comparisons. I did an analysis of w-2 vs 1099, with my current company CACI and what I would need to make it worth my while when I do make the switch. Also, verifying who owns your clearance. Chapter 12 that I'm currently finishing up (page 98 currently), has been an awesome eye opener to say the least.

                                4) What would be three other benefits to buying the book?
                                A. It's a strong reference to help organize and manage your 1099 path both logically and mentally.
                                B. It helps the user to understand potential issues and problems that could occur during the 1099 journey and provides ways to assist in mitigating them upfront
                                C. It's built around real life experiences and success stories that are invaluable to anyone going down this path.

                                5) Would you recommend Going 1099? If so, why?
                                I would recommend Going 1099 to those who have the desire to have more control over their career and life and don't mind the extra minor work involved to maintain the business and grow it. Secondly, I am interested in it because I want to cut down on the corporate employee notion of climbing the ladder. I would rather drive my career forward and have the best opportunities instead of waiting in line for a promotion and some title. Honestly, I'm tired of corporate politics getting in the way and slowing down my career options.

                                6) Is there anything you’d like to add?
                                Not really, the book lays out a lot of items that causes anyone who is interested to go do their own research as they build their own path toward this endeavour. If I were to add something to readers, I would say something like the following:
                                "Contracting can be a "tight-knit" community if you stay long enough in a department, agency or even field such as cybersecurity. Eventually, you will hear of someone you know and they will know you, so your best asset is a good reputation. Building good relationships will outlast any contract. It's how you make others feel, like you care about them and how they are doing instead of what they missed at the last meeting or didn't get a chance to do for you let's say. Like this book says, small talk is so important to beginning a conversation/relationship that will yield benefits long term to help you be successful. At the end of the day, you want people to answer the phone when you call because they know you are worth talking too and you aren't just another person calling.