Jenna Rainey


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hey friend!

I’m Jenna Rainey. 

I'm an artist, self-taught designer, and multi-faceted creative entrepreneur who is hell-bent on teaching everyone how to find their inner creative voice.



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A highly creative nerd with a unique breed of humor and the proud earner of a self-bestowed award for being the world’s most curious and driven human.

Hey I'm Jenna!

(with me)


It’s like Netflix-binging Bob Ross videos, but with a dose of dry + quirky humor and fewer happy little tree references. 

Wanna Learn Watercolor?

i wrote some books



What It’s Really Like Working for Jenna Rainey with Kelly Martín

Business Resources


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Just over a year ago, I decided it was time to hire an assistant. I wanted to grow my business and also do less of the things that weren't my specialities. That's when Kelly Martin came into my life and now, she's my right-hand lady/operations manager/integrator.

I'm super excited to introduce you to her and let you all in on what it's really like behind-the-scenes working at Jenna Rainey HQ.

Kelly is just the organization to my Type B-ness. She is the poking holes to my big crazy ideas. She is the detailed-oriented Asana task champion. She just has absolutely changed my life.

In this episode, Kelly gives some really good, honest answers about:

  • My strengths and weaknesses
  • How we met and the interview process
  • Why Kelly and I make a strong team together
  • What she does, what her roles and responsibilities are within my business
  • Some of her favorite organization hacks

Even if you don't have anybody working for you right now, knowing about the dynamic with somebody who does take on an operations manager role can be insightful and helpful for the future!!

Related Post: How to Make the Right Hire


Stellar insights

  • [03:14] Kelly shares her how she started in the online business world 7 years ago.
  • [06:15] Kelly's ONE-sentence introduction to me on LinkedIn had me at hello and I knew she was the one.
  • [09:09] A run down of Kelly's roles and responsibilities
  • [14:56] 3 considerations when looking for the RIGHT person to hire for your business
  • [19:14] Kelly shares her favorite things about working with me.
  • [23:58] She also gives her view of general qualities she appreciates in a good manager.
  • [28:42] Kelly tells all—challenges she's faced working with me.
  • [33:57] Insights for setting up efficient and productive systems in your business
  • [38:21] Kelly shares tips and tricks she's picked up over the last 7 years. Organization hack #1: Browser bookmark folders
  • [41:17] Organization hack #2: One tab chrome extension
  • [42:17] Organization hack #3: URL indexes
  • [44:04] Organization hack #4: Naming conventions for digital files


Rapid Fire Questions

What is the best advice you've ever been given? 

It was an interview with Elizabeth Gilbert, the author, and she said, “Follow your curiosity.” We put a lot of pressure into saying, follow your passion. Well, what's your passion? Sometimes we have a lot of passions, right? And so how do we just pick and go with it and commit? And that's kind of a scary thing to just pick one of many interests. That's something that has stuck with me throughout my whole career — follow your curiosity. Because that's what I did. I studied psychology and Spanish education and here I am. What led me here was I was interested in all these different things and just followed that. So I say that thinking of a lot of artists and a lot of people that write in and say, ‘I'm not quite sure do I do acrylic? Do I do oil? Do I calligraphy? What do I do?' Follow your curiosity and yeah, you can pivot and you can change. And that may open up another door. And if it doesn't work out, you've learned a skill or you've had an experience that will only make the next one better.

What book have you recommend the most to others?

The first one shouldn't surprise you—The Life-Changing Magic of Tidying Up by Marie Kondo. I mean, that's been life changing for more than just me and I recommend that to everybody. The second one is The Four Agreements by Don Miguel Ruiz. Just good reminders about life. Easy read. Very good.  

What is something you've learned about yourself this last week? 

So in our Monday meeting, Jenna said to me, ‘You're going to be on my podcast.' I was like, really? What am I going to say? What do people care about? Like, is there anything actual of value that I can share? You know, the whole imposter syndrome, which keeps coming up with a lot of people in this community. I was feeling that pretty strongly saying, ‘I don't know what to say.' I took a couple days to really think about it. And I realized that I do have something that I think could be valuable to someone out there. That was what I learned—to try to overcome that imposter syndrome and keep sharing.


Subscribe & Review

If you had an ah-ha! moment or learned just ONE new valuable bit of information, I'd be so grateful if you would leave a 5-star review and tell me what you love most about this podcast. It's a HUGE motivator for me to keep creating this for you. In addition, it helps our raking in iTunes so that more people discover this show.

And to make sure you never miss an episode (including any pop-up bonus episodes), click here to subscribe on Apple iTunes!


Links mentioned

*This is an affiliate link which means that I may receive a small commission at no extra cost to you. This helps me be able to produce free, valuable content for you. Thanks for your support!


Related Episodes

Episode 28: How to Make the Right Hire
Episode 5: What No One Tells You About Being Your Own Boss
Episode 16: 5 Steps to Create Your Annual Promo Calendar
Episode 20: Social Media Boundaries to Adopt to Protect Your Mental Health
Episode 40: The Importance of Curiosity and Creativity with Brit Morin


by Jenna Rainey 

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