Dear Jenna: How did you hire a Virtual Assistant?

Jenna Kutcher 

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August 22, 2016


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Dear Jenna, 

My business has grown quickly over the last few years. So far, I’ve been able to do everything myself but I’m getting to the point where I can’t take on any more work unless I get help. I’m feeling overwhelmed by the daily to-dos, the overflowing inbox, the images waiting to be blogged, heck, I haven’t submitted anything in a year or two (I just don’t have time.) I think it’s time I bite the bullet and hire a virtual assistant but I don’t even know where to begin. I know you hired one this year, can you tell me how you went about it? 

Sincerely, Send Help I’m Stressed 

I still have emails from her from 2015. I cringe when I think that I didn’t take her up on her offer back then, if only I had just taken a step back from my business to really see that I needed her. It took some big life changes and a reality check to really see how much help I needed. In April of this year, I made one of the best business (and life) moves I’ve ever made and it’s made all of the difference: I hired a virtual assistant to help me with my business.

So how the heck did I go about this? Well, I wish I could tell you that I went out and found the perfect person, but I am lucky enough to say that the perfect person found me (and didn’t give up on me when I was reluctant for a solid six months!) Caitlyn had reached out a few times offering her services to me, but it wasn’t until I was really ready to give up control in parts of my business that I hired her… and if we’re really being honest, letting go of control is the hardest part.

Who is Caitlyn and what does she do for my business? 

Well, she’s a stay at home working girlboss. She’s an assistant to a handful of photographers (sadly her client list is full, but she is accepting short term VA work on a project by project basis) and she handles everything from emails to blogging, galleries to album design, SEO to Pinterest and more…

The best part is, we only live 30 minutes apart so it’s possible to meet face to face for drinks or co-working or pedicures to talk shop. The first time I met her, we talked about how she could help my business. I immediately trusted her but letting go of control of something I had held onto for the last five years was downright scary. I remember her telling me all of the ways she could support my business and telling her, “I’ll let you handle my email inbox, we will go from there” Well, we did just that – except one week in, I wanted all of Caitlyn. I wanted her hand in every single aspect of my business and I was sending her every login to my life so that she could manage different tasks for me.

Thinking about outsourcing? Grab our FREE guide to see if you’re ready! 

Currently Caitlyn does these tasks for my business:

  • Email Support: My inbox was one of my greatest stressors in my life. I stunk at getting back to people, emails got lost in a sea of unread messages. Caitlyn goes through my inbox every morning, responds to what she can, files emails for me, and notifies me which emails need a reply directly from me.
  • Blog Support: Caitlyn will prep every wedding post with linked vendors, she creates slideshows for my wedding clients, and helps with SEO and Pinterest directly from my blog! She also set up Google Analytics (yes, I didn’t have it!) and tracks all of those figures.
  • Launch Support: She spends extra time in the inbox helping during launch weeks and has even taken my courses so she can answer questions thoughtfully and with experience! She also helps with some course creation, which is amazing.
  • Client Care: Caitlyn will schedule out messages to my clients so that they always get information before they can ask for it! She delivers galleries, does album design, submits weddings to be featured, and makes sure I see and respond to all of my client questions in a timely manner.
  • Content Creation: She proofs course content, helps with areas that she excels at, reviews my courses, takes them, answers questions on them, and helps me fill in any gaps! She is so close to my content that I love having a second set of eyes and ears on it before we go live!

How has my life changed since hiring a VA? 

I can’t exactly put into words how different my life is (seriously.) This summer I’ve been gone for over a month traveling all over the world and I’ve never had to stress about my inbox or worry that my clients don’t feel taken care of. Caitlyn screens things for me, makes sure everyone is responded to in a branded way, and helps me stay on top of my to do list. She is my right hand girl and I trust her whole heartedly. I no longer feel like I’m trying to stay afloat or catch my breath, I have worked the least amount and yet my business has continued to grow.

So many things held me back from taking the leap: the expense, the time of training someone, trusting someone to love my business as much as I do… the list continues but when I finally loosened my grip of control, I finally freed my hands to grasp ahold of the things that I truly love (like my husband, time with my family, evenings hanging on the couch watching The Bachelor.) Everyone close to me has seen this giant shift in my life, my business mindset, even just the clarity I have in balance. If this post intrigues you, if you’re wondering if a VA might be a good move for you, download our freebie below and see if you’re ready to bring on someone to your team!

Not sure if you want to outsource? Thinking about it? We’ve got you covered! 

Click here to download our free outsource guide, Five Questions To Ask Yourself Before Outsourcing!

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  1. Sarah Heyl says:

    This is such great insight, Jenna! Unlike most readers I think I resonated more with someone wanting to be a Caitlyn! I’d love to learn more about her and how she manages multiple clients as a VA as I think it’s something I’m really interested in becoming. OCD organizer and planner with a knack for blogging, design and web. Maybe it’s right up my alley?

  2. Hi Jenna!

    I am on the other end of that spectrum as I am a private image editor for photographers, and it’s such a hard thing to show them how much outsourcing is going to help. What did she say and show you that finally made you take the leap? I have photographers who start the ball rolling and then disappear with the business of things. Thanks for any advice you can offer!

  3. Sarah says:

    Loved this post Jenna! This is exactly what I need but I don’t have any Caitlyns of my own reaching out to me and your Caitlyn is busy it sounds like! I’d love some input on where to look for a VA (my Google search was disappointing and unyielding 🙁 ).

  4. Erin Brannan says:

    Is that really Caitlyn’s site in the links? It’s like a European clothing company 😉

    • Hey Erin, Caitlyn here! No, I don’t have a website anymore as I’ve joined Jenna’s team full time and sold my business! The first year we had the site forward to Kate Quin (who took over my VA clients), but we no longer support that domain. You can check her out at if interested!


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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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