Mentorship & Education

Opportunities to partner with me to learn more about improving your photography skills, refining your approach to video, evolving as a content creator, and navigating the ins and outs of entrepreneurship.

About my mentorship & education offerings

Whether you are looking to dust off your camera to get more comfortable behind the lens in preparation for your next adventure, or you are curious about how to grow your content creation business, I'm thrilled to partner with you! A mentorship session is the perfect way to learn from a peer who not only has experience in content creation, but who is invested in helping you create to your fullest potential. I have personally and professionally benefited greatly from creating alongside someone else and have found it to be so encouraging and motivating.

I offer a handful of different focus areas and offerings, some of which can be customized to fit your unique goals as a creator. Take a look at the offerings below and don’t hesitate to reach out with any questions!

Who these opportunities are best suited for:

  • Real estate professionals looking to establish a presence as a lifestyle brand

  • Design professionals seeking easier strategies for creating content

  • Travel bloggers who are eager to hone their photography skills

  • Creatives feeling the pressure to produce reels

  • Families looking to better document their travels and experiences

Topics that we can focus on:

Developing your eye as a photographer

  • Establishing and curating vision

  • Scouting the proper location

  • Understanding camera settings

  • Posing and working with others

  • Navigating lighting

  • Editing and post processing

  • Managing posting and social media

Leveraging video as a content creator

  • Reels 101 – and how to define your perspective

  • Filming tips and techniques

  • Managing and organizing content

  • Understanding lighting

  • Editing and post processing

  • Optimizing hashtags and creating a posting strategy

  • Leveraging content cross platform

Building a creative business

  • Developing your eye and perspective

  • Identifying your goals and focusing your efforts

  • Defining your voice and target audience

  • Developing a client experience

  • Refining your branding and social media presence

  • Honing an internal workflow

  • Establishing systems and articulating boundaries

Types of offerings:

Coaching / Consultation calls
(offered virtually)
These discussions are typically an hour long where any question is on the table! I’m happy to help answer any questions you have about photography, content creation, and creative entrepreneurship, and to encourage you as you explore and investigate your creative perspective. Investment begins at $475 per hour.

Customized, half day mentorships
(offered virtually and in-person)
These four-hour mentorship sessions go deep on one topic area, allowing us to focus on developing photography skills, documenting your perspective through short form video / reels, or refining and building a creative business that aligns with your values. Each session is customized to best suit your particular goals and objectives. Investment begins at $1,825.

Customized, full day mentorship & strategy workshops
(in-person only)
The eight-hour mentorship and strategy workshops are best for those looking to touch on multiple tracks, including photography, content creation, and creative entrepreneurship. The sessions are customized and designed to leave you with all of the tools and techniques you need to build a business that aligns with your creative perspective, as well as a sustainable strategy for implementing and maintaining a rhythm. Investment begins at $3,625.

What people are saying:

“Thanks so much for this info. I definitely need to get out more to DC and Old Town. It was such a lovely afternoon and I felt so happy and in my element doing something I love in a different setting. Thanks for sharing these locations with me. Just wanted to say how much I appreciate your honesty and willingness to share your perspective and thoughts with me. This is super helpful, thanks for being open and sharing your personal outlook.”

1:1 mentorship attendee

“Chesley is such a great mentor! She thoughtfully answered all our questions regarding reels and is such a great resource to have!”

Reel workshop attendee

“The workshop with Chesley was such an informative experience and I'd highly recommend it to anyone considering learning more. Chesley's hands-on approach allowed us to practice the skills we were taught, and her kindness and willingness to share expert information made me feel so supported and motivated to go create more content!”

Reel workshop attendee

Coaching / Consultation calls

In these sessions, we will connect over a virtual coffee and all questions are fair game! I’m here to be a resource to you, to encourage you, and to be an open book with absolutely everything I know. Whether you want to talk about editing, styling, posing, social media, or the steps needed to turn your hobby into a thriving side hustle or all-time business, I want to make sure the content of the call is useful to you and your goals. You’ll receive some notes after our call with some tips and tricks for future reference, and you’ll also be added to an exclusive newsletter where I share monthly updates, ideas, and resources from the world of content creation.

Best for: Creatives who are curious about content creation and looking for a high-level view of best practices

Investment: 1-hour session for $475

Half day mentorships

If you are looking to explore a neighborhood and learn more about photography, understand how to film and post reels, or develop a tone of voice as a lifestyle brand, the half day mentorship option gives us the perfect opportunity to define your perspective and put it into practice.

While each mentorship is tailored to meet your particular goals, there are a few specific areas that we will focus our efforts around. I’ll coordinate with you on an exact itinerary and schedule for the day, whether we are meeting in a neighborhood, at a client project, or at one of your listings. In these sessions, I’m an open book on my exact process, from choosing a location and setting an itinerary, photography and filming techniques, editing and posting considerations, and more. You’ll receive some notes after our mentorship with some tips and tricks for future reference, and you’ll also be added to an exclusive newsletter where I share monthly updates, ideas, and resources from the world of content creation.

Best for: Creatives who are looking to take their skills to the next level and establish new, sustainable rhythms

Available focus areas

  • Photography

  • Content creation (iPhone-only reels and photo)

  • Creative entrepreneurship and building a lifestyle brand

Investment: $1,825 per attendee

Full day mentorship & strategy workshops

All day workshops are an opportunity to dig deep, define a strategy, and outline exact steps for execution. I recommend the full-day workshop for clients who are curious about photography, content creation, building a perspective in the lifestyle space, and who will need to touch on a multitude of topics in order to reach their goals. We will find a place to set up shop, and I’ll walk you through every step of my process when it comes to photography, creating reels, and building a brand online. Attendees will receive a follow up with notes and resources from the workshop, and you’ll also be added to an exclusive email list where I share monthly tips, tricks, thoughts, and updates from the world of creativity and content creation.

Best for: Real estate and design professionals looking to fully revamp their approach to showing up online

Some topics we will cover:

  • Skillbuilding for filming reels, photographing spaces, and capturing your environment

  • Defining your target audience

  • Aligning your tone of voice to your visual direction

  • Focusing your creative efforts most effectively

  • Converting comments into clients

  • Driving traffic and getting an ROI on your content

  • Understanding social media best practices

  • Hands on editing session for reels and photography

  • Establishing and maintaining content creation habits

Investment: $3,625 per attendee

What to Expect

Confirmation and calendar invite
I’ll follow up with a contract, a calendar invite, as well as an initial invoice; consultation calls are billed upfront, and half-day and full-day workshops can be paid in installments. If we are meeting virtually, you’ll receive a virtual call in link!

Brainstorm (for half day and full day mentorship participants)
Keep an eye out for a questionnaire that I will use to better understand your vision and your goals for our time together.

Set the vision and itinerary (for half day and full day mentorship participants)
Based on your answers on the questionnaire, I will curate an itinerary and schedule for our time together. I’ll send this your way for a review to make sure we are covering topics that best align with your goals!

Meet up (for half day and full day mentorship participants)
When the magic happens! With our schedule as a guide, we will connect first for some introductions and a presentation before heading out into the field, whether a listing or a part of town to explore. We will wrap up the session back at your office or at a coffee shop, where I’ll show you my editing process or how I compose reels, depending on the track you chose.

That’s a wrap!
After the session, I will follow up with some notes and top tips to keep in mind as you continue your pursuits. You’ll also be added an exclusive newsletter, where I’ll share monthly thoughts and findings specifically on what I am hearing, seeing, and learning in the ever evolving space of content creation. At the end of our session, know that I am available as a resource to you moving forward for any questions. I’m always ready to lend some encouragement!

Frequently asked questions

  • The half day mentorship sessions and full day mentorship and strategy workshops will be tailored to suit your equipment setup and goals. If you prefer to work just with your phone, I’ll show you how to optimize your settings for both photo and video to get the most of of the tool. If you’d like to develop a comfort with a professional camera, I’m happy to include that in how we structure our time together!

  • There is always the opportunity to meet virtually, however for the half day mentorships and full day mentorship and strategy workshops, I recommend meeting in person! Where we meet is dependent on your goals for the session; some clients are looking to develop their eye as a travel photographer, and so we meet in Georgetown to explore the shops, cafes, and restaurants while practicing food and lifestyle photography. For clients working in real estate and design, it might make more sense to connect at the client’s office and then visit a project or listing together.

  • All participants will receive some notes from me after our time together that outline our discussion and recap the recommendations that I shared. I’ll be sure to include any best practices and top tips that we discussed, and you’ll also be added to a newsletter list where I share notes on a monthly basis that you might find constructive to your creative goals. Presentation materials shared during our time together will not be available afterwards, but I’m happy to note any helpful references and to answer follow up questions.

Have a question about mentorships? Get in touch!