Goal Digger Episode 007: How to Hire the Right Virtual Assistant with Caitlyn Jeffery

Jenna Kutcher 

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December 14, 2016



Today Caitlyn Jeffery (my right-hand girl!) will be talking all about the process of joining my team, being a virtual assistant and how she created this role for herself 7 years ago. She’s also talking publicly for the first time ever about why she recently made the decision to sell her business and join me full-time.  I tell her all the time that I don’t know how I survived without her and I’m excited to introduce her to all of you today and share some tips about why accepting help into your business is so important as well as tips for finding the right fit. Don’t miss our guide “Five Questions To Ask Yourself Before Outsourcing” guide below!



Caitlyn owns a business offering virtual support for photographers all over the world. She has a degree in marketing and finance and was working in the corporate world, but “fading away in a cubicle” (1:07).

“The first step was getting out of that corporate world; I knew I wanted to work in a more creative industry.” (1:51)

She decided to turn her hobby of photography into a business. She realized photographers didn’t want to handle the business side of things and would be willing to outsource it. Caitlyn signed up her first client when her first child was born and has grown her business successfully for the last 7 years (2:00).

A lot of business owners might find that they have a hard time to let go or learn what to delegate when they discover that they do need the help. Caitlyn says to start small when handing over the tasks or projects and just go from there (7:00).

“Let them take over that one piece and then grow it to the next thing and the next thing; pretty soon they will be well versed in your business and they will care for it like you do if you find a good person.” (6:43)

Caitlyn knows that she thrives in a team setting and likes to support entrepreneurs because she knows that when being an entrepreneur. often times you can feel alone (9:04).

“I’ve always loved being that support person, and when I became the happiest was when I just realized that my strengths come in the planning and the tactical and behind-the-scenes.” (9:24)

Caitlyn has recently decided to sell her business and commit full-time with me. The many reasons she decided to do this was because she was so bogged down that she felt she wasn’t giving everyone 100% of her, including clients and her family (12:00).

“I was carrying so much weight from it that it was causing me to miss the joy with my family and I was dropping balls, which was the red flag for me” (12:40)

When it comes to seeking out a virtual assistant, she advises that you first identify the pieces that you love doing the most and what you don’t enjoy doing and lastly what isn’t getting done. This is going to help you identify a task list and determine the type of person that you are looking for (17:00).

“If you accept help you’ll be able to get to more done in your business” (18:03)

One of the many things that Caitlyn has learned from me is the power of rest. Within a small business there always seems to be a need for hustle, but entrepreneurs forget to make time for themselves and unplug (22:43).

“Just because we are small businesses and work out of our home and people have our cell phone numbers it doesn’t always mean we have to be working” (23:00)

Caitlyn and I are such a good fit because we are able to respect each other’s boundaries, but we also have very different skills sets and strong points (28:00).

When it comes to being a mompreneur, Caitlyn says it started when she had a very new baby, working at nap times and in the evenings. A lot has changed recently  since she has started practicing the lesson she learned about unplugging and scheduling time for her daughters (30:27).

“I do this business and have this flexible career so I can be present with them when they are home and creating those boundaries and scheduling time for rest and making memories with them” (30:59)


Caitlyn’s VA Business – Kate Quin

002: Creating an Unforgettable Brand with Jen Olmstead 

006: How to Pack a Punch with Words with Ashlyn Carter



What Color Is Your Parachute? 2017: A Practical Manual for Job-Hunters and Career-Changers

The Pumpkin Plan: A Simple Strategy to Grow a Remarkable Business in Any Field

The Best Yes: Making Wise Decisions in the Midst of Endless Demands


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  1. Bri A says:

    Love this! As a VA, I love seeing our industry represented and hearing about how hiring Caitlyn helped you. Another amazing episode as always, Jenna!

  2. Why You Should Fire Yourself { Diary of a Creative Entrepreneur, Volume 7 } - MichelleHickey.Design says:

    […] this episode of The Goal Digger Podcast was instrumental in giving me the confidence I needed to make that list […]

  3. Tera Nicolo-Smith says:

    I loved this episode. I would love to hear from Caitlyn to better understand what a day in her life looks like. I am super interested in becoming a VA, but I feel unsure about the skills required. I would love to learn more about what she does before diving in.


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A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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