Turn Your Expertise into Goldmine – Government Contracting Secrets with Dr. Jeannie Headley

With proposed federal budget cuts ranging from $1 to $2 trillion, many federal agencies have scaled back their operations – terminating existing contracts and slowing the issuance of new ones. The administration’s proposal to reduce the federal workforce by 20% further limits these agencies’ capacity to manage and award contracts effectively.

While the industry has become more competitive, many people mistakenly believe that winning government contracts is nearly impossible today. The truth is, if you have a skill set or expertise that the government needs, you can still secure contracts—even in the midst of political shifts and uncertainty.

Dr. Jeannie Headley is a prime example of what’s possible—she leveraged her expertise in grant writing to secure $60,000 in government contracts, despite political changes that made the landscape more competitive. Let’s take a closer look at how she made it happen.

From a Professor and Grant Writing Consultant to a Government Contractor

Dr. Jeannie Headley had been working in grant writing for about five years, knowing it was her strength and passion. But for a long time, she saw herself more like an employee doing contract work rather than a true business owner.

“I’ve been doing grant writing for the last five years, but as far as me taking it seriously and actually being a business owner—and not just an employee or feeling like an employee when I’m working with the folks that I’m contracted with—that really started this past year,” she recalled.

That change in mindset led her to decide to fully commit to her role as a business owner, focusing on growing her grant writing business with a professional and strategic approach.

This is the driving force behind the launch of Core Vision Solutions. Dr. Jeannie Headley founded the company to help nonprofits and universities secure sustainable funding—without the overwhelm. As of now, the company has helped clients obtain over $22 million in grants.

Dr. Headley handles a wide range of grants, including foundation, corporate, and federal funding. For clients such as cultural and historical preservation organizations, she emphasizes foundation and corporate grants and also reaches out to philanthropists to broaden funding sources. Federal grants, however, are more complex and demand strict attention to detail and compliance with regulations.

While her main focus is on grant writing, she also provides guidance and consultation to individuals and businesses who are new to bidding on government contracts. She helps them understand the often complex and intimidating process by breaking down the requirements step-by-step, explaining how to follow the criteria, and offering practical advice to increase their chances of success.

In addition to serving other clients, Dr. Jeannie Headley has successfully ventured into government contracting, leveraging her unique niche to secure contracts totaling around $60,000.

The Power of Niching Down

Before branching out into government work, Dr. Jeannie Headley used Upwork to find freelance opportunities and build her client base.

At first, she used platforms like Upwork hoping to earn extra money, trying to offer a wide range of skills just to see what would stick. But that generalist approach didn’t attract many clients.

Realizing this, she decided to narrow her focus and present herself specifically as a grant writing expert, which is her true area of expertise.

“Because of that, I customized my profile to really showcase what I can do, what I can bring to the table, and be specific about the areas I actually work with. A lot of folks are just all over the place, and being really specific helped,” she explained.

Once Dr. Jeannie Headley revamped her Upwork profile to really show off her strengths in grant writing—highlighting her past work and being crystal clear about the kind of clients she wanted to work with—everything started to shift. Instead of chasing down gigs, clients started coming to her.

She expressed, “That allowed me to actually get folks reaching out. I’m not going to lie—I was very shocked, like, wow, they’re reaching out to me!”

Give Yourself the Freedom to Be Selective

Taking on every opportunity can lead to burnout. Being selective ensures you’re investing your limited time and energy into work that truly matters to you and aligns with your goals.

That’s what Dr. Headley believes. Her full-time job as a professor gives her the financial breathing room to be picky—in the best way possible—when it came to freelance work on Upwork.

Instead of accepting any job just to make money, she chose projects that felt aligned with her values, interests, and expertise—specifically grant writing.

“I feel like I had the privilege to be selective because I have a full-time job as a professor, so I’m not like super eager to make ends meet or anything like that,” she stated.

That selectiveness allowed her to focus on high-quality work, which led to strong client reviews. Over time, this built up her reputation on the platform, and clients began reaching out to her instead of her chasing jobs.

“I was able to select projects that align with me and then build up my profile with great reviews. Because of that, folks reach out to me, which is incredible to have someone reach out to work with me,” she said.

As of now, she has pulled in $20,000 in just one quarter through Upwork.

Confidence Helps!

Dr. Jeannie Headley’s journey wasn’t just about mastering grant writing or landing contracts—it was a journey of changing how she saw herself.

She admits there were moments filled with imposter syndrome, that feeling that maybe didn’t really belong or wasn’t quite good enough. But instead of letting those doubts hold her back, she started looking at her accomplishments and reminding herself of all the hard work she had done.

“And, you know, a lot of impostor syndrome happens—I know for me at times, and for a lot of people. But at the end of the day, you have a record of all your accomplishments, and when you look back at that, I think it’s so incredible,” she said.

She realized that believing in herself was just as important as any skill or strategy. What made this even more powerful was learning to embrace all the roles she juggled such as being a professor, a business owner, a mom—and feeling confident in handling them all at once.

“You can have it all; it’s just the balancing that I think is so important,” she emphasized.

Leverage Your Expertise and Background to Thrive in Government Contracting

As a Grant Writing Consultant and Fundraising Strategist, Dr. Jeannie Headley brings deep expertise in strategy, storytelling, and relationship-building. Beyond her consulting work, she’s also a professor of English Literature at Montclair State University, specializing in Linguistics, Literacy, and Cultural Preservation.

When she entered the world of government contracting, she combined her unique strengths—grant writing and a strong foundation in English—to give herself a powerful edge. This blend of skills became her “silver bullet” for both winning bids and delivering high-quality work.

According to the professor, many people struggle to clearly connect what their organization needs with what funders are actually looking to support. However, this isn’t a roadblock for her. With a strong background in English, writing, and literature, she knows how to bridge that gap.

“I feel like my background in English, writing, and literature helps with that. I can lean on that to really convey what my clients want but also what the funders want as well. Then taking it a step further, being strategic and thinking about what projects they have that align with what they want to get funding for,” she articulated.

With her extensive experience, Dr. Headley knows how to turn big ideas into clear, compelling messages that resonate with funders. She helps clients clarify their goals, align them with funding opportunities, and communicate their impact in a way that stands out.

She stated, “These are great opportunities to make a difference in communities. Just making sure that’s super clear has helped a lot—having conversations and helping them see a clearer vision of what they want. That’s been super helpful, me leaning on my background with that.”

Besides, Dr. Headley firmly believes her background gives her credibility—and she’s right. In her case, that credibility has helped clients feel confident handing over big responsibilities. They trust her expertise, which allows her to take the lead on projects and deliver strong results.

“I think my background adds credibility—I don’t think I know it does. Even just being a professor, that aspect in particular, or you don’t have to be a professor, perhaps you’re an educator in general—it just adds credibility,” she explained.

It’s a reminder that your past experience, when aligned with your work, can become one of your greatest assets.

“Whatever your background is, if you can tie it into whatever you’re doing, it just adds credibility.” She added.

Give Them What They Want!

As shared by Core Vision Solutions’ Owner, in government contracting, it’s crucial to carefully follow all the requirements without adding unnecessary information.

For example, writing extensive company histories that don’t directly relate to the contract can make your proposal longer than needed without adding value. Instead, focus on relevant experience that clearly shows your ability to handle the specific project.

Reviewers have to sift through many proposals, so the best approach is to give them exactly what they ask for—clear, concise, and on point.

“Don’t add the fluff and try to impress them too much. Of course, your work can speak to it, but you definitely want to give them what they want. They’re reviewing a lot of proposals, not just yours, so you have to just give them what they want,” Dr. Headley believes.

She also shares that missing even one required item can disqualify your bid, so having a detailed checklist to track every requirement is essential.

“I like to create a checklist to make sure I’m checking off everything, hitting all the requirements. You don’t want to be disqualified for missing one thing, especially when it could be something so simple,” she said.

You Need a Community!

When you are an entrepreneur, you need a community!

While friends and family may care deeply, they often can’t fully relate to the mindset and challenges of building a business. In contrast, being around other entrepreneurs fosters growth by exposing individuals to new ideas, encouraging bigger thinking, and offering real-life examples of success in unexpected areas.

One of the most powerful things about being in a community of entrepreneurs is that it’s a space where you don’t have to pretend you have it all figured out. You can ask for help—openly and honestly—because the people around you get it.

That’s what Dr. Headley has found in her journey as an entrepreneur.

Also, if you’re a young entrepreneur, there are young entrepreneur groups and things of that nature. For me, I’m part of a couple of entrepreneur groups, and it’s really great because I get to talk about the whole journey. I can talk to my husband about it, but he’s not an entrepreneur, so it’s really great to lean on folks who get it,” she stated.

“Sometimes you just need an uplift moment—you need some motivation—and I think that’s super helpful. So community is really, really important. I wouldn’t be here without my community,” she added.

Dr. Headley often connects with others online but values in-person meetings as powerful opportunities to reset, reflect, and focus—especially helpful for parents juggling work and family. She also uses co-working spaces, both virtual and physical, to stay productive, noting that a calm, structured environment helps her accomplish more for her clients and herself.

Write Down Your Fears and Seek Answers!

Many people, when they are new, have many fears about getting started—especially in grant writing or government contracting. Dr. Headley suggests writing those fears down to see clearly what’s holding you back. Whether it’s doubt about your ability, time commitment, or confusion around the process, putting it on paper helps you face it.

“Well, write down your fears—I think that’s important. What is stopping you? What are you afraid of? See it on paper. Face it. That is one way of dealing with fear: just writing it down. What scares you? What is creating the doubt? And then, seek answers to that,” she explained.

“You know, it could be something as simple as wondering, ‘How many hours do I need to put into writing a proposal?’ Maybe you don’t need to put in a lot of hours. I mean, we hear about people doing proposals every night, right? Just getting it done. How is that possible? Well, maybe it’s because they’ve created a template to help with that—something to lean on. Automating that process could be really helpful too,” she added.

Focus on Something that You’re Truly Passionate About!

While there are countless opportunities out there, she believes that passion is what sustains long-term commitment. If you’re not excited about the work, it can quickly become frustrating, tedious, or overwhelming. But when you care deeply about a cause or industry, you’re more likely to stay motivated and follow through—even when challenges arise. Passion makes the process more enjoyable and the success more rewarding.

“Finding out what you want to do, what area you want to go into, and sticking with that—I think that’s so important as well. Of course, you could go after so many opportunities, but if you think about something you’re truly passionate about, you’re going to stick with it because you’re passionate about it. If you’re not passionate about something, you’re just not going to stick with it. It’s going to be really hard, it’s going to be not fun, boring, frustrating. You want to be passionate about something,” the professor said.

Just Do It and Don’t Give Up!

Dr. Headley often hears stories from people who are just getting started in government contracting—and they’re already landing contracts. At first, it seems wild, almost too good to be true. But as she listens more closely, a pattern starts to emerge. These aren’t people with years of experience or massive teams behind them. What they all have in common is persistence.

They show up. They respond to what’s required. They make mistakes, learn from them, and keep going. They don’t wait until everything is perfect—they just start. Again and again, Dr. Headley sees that it’s not about having all the answers from the start. It’s about putting yourself out there, doing the work, and refusing to give up. That’s the thread tying all these success stories together. It’s not magic. It’s consistency. And it’s absolutely possible.

She stated, “It’s not about having everything figured out from the start—it’s about not giving up and just doing it. That’s the key. They keep showing up, putting themselves out there, responding to what’s required, and staying consistent. They don’t let doubt stop them. They just keep going. And that’s what makes the difference. It’s possible—it really is,”