Karen Greenoe

How to Start Outsourcing-Jenna Daykin

Jenna’s company, In the Details Darling, was born out of a need for more work life balance for small business owners, more specifically moms, who needed help managing the back end of their business. She’s seen so many business owners fall into the trap of letting your business control your life instead of the other way around. She now works as a brand manager, strategist, mentor to future virtual assistants. 


Karen:  Where did you originally see the need for your business? What inspired you to get started? 

Jenna: Well, to be honest, I was a bit inspired by you, Karen! I loved your ability to get your clients excited about working with you. I always wanted to be an entrepreneur I just wasn’t quite sure what to do yet. I was working in the travel industry and talked to a number of my business colleagues and saw that there was a real need for back end support in small business. I saw that things weren’t necessarily being done in the most efficient way possible. That is where I come in! I now continue to serve the travel industry but also specialized creatives.


Karen:  What are some tips that you could give to an entrepreneur who knows they need help and don’t know where to start or are scared to ask for help? I know when I started outsourcing, I had a very traditional model of employment in my head…salaries, 40 hours a week, etc, and it was a little daunting!



  1. You have to have systems in place. Otherwise, you will be spending money and wasting time and they won’t be able to accomplish anything. I create workflows and canned emails and that helps immensely. Letting go can be so hard! But when you put structure and systems in place, it makes it easier to release the reins. 
  2. Determine what you’d like to outsource. Look at the areas of your business that aren’t getting done and start there!
  3. Ask yourself what your business would look like if you had more free time? Could you take a brain break and move your business forward more?
  4. What are the tasks that you love to do? What are the things that only you can do? What are the things you don’t know how to do? What are the things you don’t want to do? What tasks do you feel like you SHOULDN’T be doing?


Karen: What would you say to someone who is intimidated by the cost of outsourcing? I know that I have a very tight grip on money. Its a product of my upbringing. 

Jenna: The investment you spend to get things off your plate is worth it. Not doing so actually COSTS you money. Don’t think of outsourcing as an expense, think of it as buying back your time.


Karen: Where is the best place to find a VA? 


  1. Word of mouth! Ask business owners you admire if and where they outsource. By consulting with other professionals, you’ll be able to get  social proof on an individual or outsourcing company.
  2. Outsourcing with Love-this is a total shameless plug! One of my clients is a VA who has been booked up for a very long time and is constantly having to refer out work. So she created a VA directory of pre-vetted professionals that you can plug into your business. Each VA in the directory has to have at least two referrals from past clients in the area they are wanting to work. There is no charge for business owners for use the directory so you should definitely check it out!


Karen: What are small business owners doing that is actually making their job harder?

Jenna: Not documenting as you go which makes the transition into outsourcing a lot harder.

Not revisiting your systems, as you grow, your systems need to grow and change too.


Karen: What is your process for asking for feedback from past or current clients? I know sometimes it takes an outsider’s perspective to know when we need to change. 

Jenna: I always ask my clients to state “one thing I wish Jenna would change” and “one thing I wish Jenna would never change.” Its amazing the feedback you get! You have to have a little bit of thick skin sometimes, but it is worth it!


Karen: What is something you’re excited about right now?

Jenna: Well, I’m working through a rebrand which is super exciting! I’m also working on a  curated client experience package that includes gifting, systems, canned email content, etc.

I really believe in surprising and delighting. Its the simple gestures make all the difference! It is my goal to live life as I’m feeling it. I need to express what I’m feeling, especially gratitude, to those around me. Because not everyone receives it! You feel it in your heart but you don’t necessarily share it. And that is what I’m all about!



Jenna Daykin is a systems strategist and brand manager who helps travel professionals and specialized creatives gain back freedom in their businesses through systems implementation and task management. She believes wherever you are, you should be all there – life, business, and everything in between. You can find her working through her to-do list at a cozy coffee shop, getting lost in the streets of a quaint city, or spending a quiet night in with her husband and two sweet pups.


September 4, 2019

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Karen Greenoe