How I Freelance: Naomi Hattaway

How I Freelance: Naomi Hattaway

People move on from positions all the time. And when they do, it can give way to a host of complexities, complications and confusion for an organization, especially when leaders leave.

Naomi Hattaway thinks there’s a better way to facilitate the process. As a consultant, she works with individuals, companies, nonprofits and political campaigns with her “Leaving Well” program, designed to help them navigate personnel transitions.

Read on to learn more about Naomi and how her experience in working with affordable housing programs led to her current work.

When did you start freelancing?

I worked in the nonprofit space with a focus on affordable housing impacts, and I’ve also been a licensed Realtor since 2014.

I first started freelancing during Covid. I was called on to support the emergency rental assistance funding from the federal government, as well as launch and implement a noncongregate shelter by leasing several hotels for folks over the age of 55 who were experiencing homelessness. I learned so much!

Following that, I stayed in the nonprofit space as an employee and helped to launch a new organization in Omaha, Nebraska, in September 2021. After a relocation to Florida changed my employment status, I went full-time freelance in February 2023. I’m not looking back!

What is your specialty?

I call it Leaving Well. It’s navigating the leaving of jobs, places, roles, titles and projects – and leaving with intention and joy.

I offer consulting to individuals and organizations who are ready to acknowledge that people leave, and they wish to prioritize embedding practices and tools to make it better for all involved.

How did you get into that line of work?

It chose me! I’ve mostly been freelancing in the space of homelessness prevention and affordable housing, which is what I’ve focused on since 2014.

The Leaving Well work, which is now my priority, landed in my lap as I started talking publicly about my own journey and experiences with workplace transitions in 2021. After I ran for public office in 2022, I realized the necessary work of normalizing the reality that people leave (jobs, places, projects, contracts) impacts so much more than just the traditional workplace.

Folks started reaching out to ask for advice in their own situations, including political campaigns, volunteering, board of directors, jobs, etc. I decided to formalize it (i.e., start charging money for my services!) in late 2022.

Why did you decide to pursue that line of work as an independent consultant?

I wanted to be fully in control of my work cadence. (Although that’s kind of a silly thing; I know I’ll never truly be in control.) Mainly, I deeply desired flexibility and the option to design my mornings and, ultimately, my relationship to work and productivity.

I also know that I’m really creative when it comes to innovation and bring a new product to market. This game-changing work of Leaving Well needed to be introduced to the world, and the best way to do it was in the capacity of a freelancer.

Who are your clients?

I work with both individuals who are leaving and organizations who are either in triage mode (a leader has just departed) or wish to proactively implement the Leaving Well framework.

Primarily, nonprofits (community serving or justice and equity focused) and social impact organizations find their way to me. But I have my 2024-25 sights set on hospital systems, entrepreneurs, large online community leaders and state and federal political campaigns!

What types of projects do you work on?

Inside of the Leaving Well work, we focus on transition planning, which includes a rigorous inventory and knowledge transfer (the way to make sure really important information doesn’t leave with the person who is departing). We also provide a beautiful documentation process for team members to embed.

We also prioritize PR and communications work. Communication about the workplace transition is SO important, both internally and externally. This includes email scripts, blog posts and media strategy where applicable.

The work done with each client is a bit customized, depending on their existing structures. It can include a really in-depth process to develop and create values-based offboarding practices, as well as support for employee retention strategies.

I also do a bit of coaching with the individuals impacted to help them with their relationship to change and transition.

Where do you freelance from?

I freelance mainly from my home office in Pompano Beach, Florida. I travel to meet clients on-site from time-to-time. My clients are all over the United States, and I appreciate being able to take my work on the road for personal trips. In the summer of 2024, I’ll experiment with maintaining client work during a trip to Asia for about a month.

What’s surprised me most about freelancing is my ability to “batch” my time and work on really meaningful and impactful projects, in a way that supports my energy, abilities and life.

Tell us about two tools you rely on to run your business.

HoneyBook is a recent addition to my business toolkit. I was previously using Motion App for booking, scheduling and task management, paired with Toggl for time tracking. But I had yet to find a solution for client management with contracts, invoicing, etc.

So far, I love HoneyBook, although I’m a novice and still learning how to best let it work for me. It offers an all-in-one solution and helps me save money from using multiple other tools as my workaround.

Name one thing that’s surprised you about freelancing.

The absolute freedom it’s provided me. I don’t take work-related calls or meetings before 10 a.m. local. (I’m on the East Coast, so that rule doesn’t impact typical scheduling conventions.)

I also don’t take client meetings on Mondays and Fridays. What’s surprised me the most about freelancing is my ability to “batch” my time and work on really meaningful and impactful projects, in a way that supports my energy, abilities and life.

I’ve discovered so much more focus and intentional work!

Made any big mistakes during your freelance journey?

The biggest mistake I’ve made is being too broad with what services I could offer. I was so excited about bringing clients in that I took too many projects outside of my true skillset and scope.

I read the book Genius Jam by Felecia Hatcher and realized that while I was good at all of those “scope creep” activities, they were much better suited for other folks to navigate.

The solution to that was building a list of recommended people to refer those activities out.

What are you proudest of with your business?

Being able to bring on a small team of folks to support the business, and being able to pay them as well as contractors with my business!

There’s lots of advice out there for freelancers. What advice do you agree with?

That it’s time to raise your rates if you’re closing every project you pitch or sales call.

What common advice do you disagree with?

Not to work for free. It’s often recommended that freelancers don’t work for free; however, I disagree with it as a blanket rule.

There are often opportunities that may help build a specific piece of your resume or portfolio, for an organization or project that doesn’t have the budget to pay your rates.

Can they offer something else you need? Do they have access to help with an item on your to-do list? Maybe they can help you with photos or your website. Give you a great testimonial. Or introduce you to a decision-maker for another great opportunity. Think expansively about what “free” could lead to.

What areas of opportunities do you see for current or future freelancers?

I see so many future opportunities in the space of collaboration, cohort-based freelancing and fractional freelancing! So many freelancers don’t have the capacity to take on larger projects or pitch themselves for complex or nuanced projects that require an ecosystem of experts. I would love to see more folks working together to accomplish freelance work in this way to support the bigger opportunities. This would mean there would need to be folks who can navigate subcontracts, but I think it’s possible!

Interested in learning more about Naomi and her “Leaving Well” framework? Connect on LinkedIn, follow her on Instagram or visit her website at You can also tune into the Leaving Well Podcast for conversations about leadership, confidence, career development, grief and more.