Ep. 033 Finding Freedom in Your Virtual Assistant Business with Jenna Daykin of In the Details, Darling


Hey, hey! Did you miss me? I don’t know if you noticed that I took a 3 week break from the podcast. I’ve been busy planning content for the fall and winter and let me tell you, we’ve got some great stuff coming up.

To jump back into the podcast, I’m thrilled to introduce you to Jenna Daykin, our guest today and the featured guest expert in The Support Squad Membership Community for October. Jenna 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.

I’m so excited for you to meet her! Let’s get started...

Jenna’s Entrepreneurial Journey


Jenna’s background is pretty diverse. While she dabbled in many different things before starting her business In the Details, Darling, they all had a common thread.

Jenna went to an all-business college with a focus on marketing and also played college basketball. When she graduated, she was unsure of what path she would take, but knew that she loved baking. So the surprising next step was culinary school! She had the opportunity to work as a sous chef for a master pastry chef and found that she was drawn to the details - the menu design, the organizing of the ingredients, and all the organizational pieces. 

Then came the next plot twist! Jenna decided that baking wasn’t what she wanted to continue to work towards, so she became an assistant college basketball coach. She once again found that she was drawn to the backend and, importantly, motivating the players.

Her next step was a move to a new city and a job as a social media coordinator and eventually she became the operations manager for a tour operator, which lead to what she is doing today!

Jenna found a real need for background support for travel, and In the Details, Darling was born! She was booked out before her business even started, just by reaching out to her clients and filling a void in the industry.

How Jenna is Preparing for Her European Vacation


Travel is important to Jenna, and by prepping in advance, she is able to make sure her clients are taken care of and that she has that important time for herself.

Her prep usually starts up to 6 weeks in advance, when she communicates to her clients that she will be out of office. PRO TIP: Jenna sends a monthly newsletter to her clients to update them on important things happening in her business, including her vacations. 

Jenna always works ahead, but it becomes even more crucial when she’s preparing for travel. Even after she sends that initial reminder, she updates clients weekly to let them know her plans so that they can work ahead and prepare. Then a week before she leaves, she gives a final warning to her clients that her current task list is all she will be able to complete before she is out of office.

Jenna also completes a week’s worth of work for after she returns from her vacation, so that she can enjoy a peaceful, easy transition back into her business.     

There are also things that Jenna focuses on in her home before leaving for a trip...including flipping her mattresses! Other tips include ordering meal delivery for the day that she returns and doing her laundry while on vacation to eliminate any stress upon her return.

Achieving Balance in Our Businesses and Lives                                              


Jenna had a wake-up call from her husband one day when he came to her and said “You don’t look up from your computer, you’re not taking care of yourself, and you’ve gotten too busy serving others.” She knew right then and there that something needed to change. 

Jenna has found that setting boundaries is key to achieving balance in her life and business. One important thing she’s noticed is that while her clients are incredible and understanding, if she starts slipping in the boundaries she’s built, it can be easy for her clients to start to slip, too. This is why it’s important to hold yourself accountable to the boundaries you’ve set!

Clear communication is also necessary for achieving balance, starting with setting clear expectations from the very beginning. This includes setting up systems of task management and correspondence.

The Trend of Being “Busy”

Jenna believes that the trend of appearing “busy” is just not cool! How often do we ask someone how they are doing and their instant reply is “I’m so busy”? We can have a full schedule without talking about our schedule all of the time.

Being intentional through the process is so important! And if you have a bad day, just make sure you’re checking in with yourself and getting back on track.

Stay in Touch with Jenna 

Jenna genuinely wants to connect with people and loves to make herself available to new virtual assistants. You can connect with Jenna at her website or on Instagram


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    Sharon Nissen