Who: Cathy Heller

Claim To Fame: Cathy Heller is the creator and host of Don’t Keep Your Day Job, through which she is growing one of the largest, most engaged audiences in podcasting. Don’t Keep Your Day Job averages 180,000 listeners around the world weekly and has over 2,300 5-star reviews on Apple Podcasts and was nominated for a Webby Award for Best Business Podcast. Prior to podcasting, Cathy spent a decade as a songwriter, licensing her music for television ad spots and shows like One Tree Hill. She just released her first book, Don’t Keep Your Day Job: How to Turn Your Passion Into Your Career, drawing on her experiences to show readers how to build a life and career around the things they’ve always wanted to do.

Where To Find Cathy: Her Website, Amazon, Twitter

Praise For Cathy: “Heller’s creative insights both inspire and challenge us to chase our art, earn the right to share it others, and never lose sight of what truly matters.” — Jeff Goins, Author of Real Artists Don’t Starve 

When and where do you like to write? Are you the same-thing-every-day kind of writer or can you write anytime, anywhere?

I tend to write best first thing in the morning. Give myself a treat of going to my favorite coffee shop and ordering my favorite honey vanilla latte. I do my best work when there’s coffee around and I’m away from the kids.

Do you have any pre-writing rituals or habits before you sit down to write?

There is just one main thing that I have to do, which is to tell myself to make the messy version of whatever I’m writing. If I have any sense of pressure around creating something genius then I wind up feeling overwhelmed. As long as I give myself permission to be mediocre, I wind up being much more productive. 

Writers have to be master prioritizers — juggling all sorts of projects and deadlines at the same time. That’s certainly the case for you. Do you have any methods for managing tasks and time to stay productive and not let overwhelm sneak in?

It’s especially true for me because I have a very full work life and three kids under the age of 7. I think I’ve learned for me that productivity is all about energy. If I’m in a good mental state I can get more done in 45 mins then I would with hours of free time if I’m feeling down. Just like we charge our Smart phones, we have to learn to charge our own batteries. Everyone I know has great ideas, but what they’re missing is momentum. When we are feeling bold, energized and excited we can make amazing things happen no matter how much time we have. The key is how we use the small windows of time that are available and we can do get so much further when we are feeling ready to unleash. The feelings of imposter syndrome can make it very hard to get much done even when we have oodles of time allotted. 

How do you judge a productive writing day or an unproductive day? What’s the sign of a good day for you?

If I got it done. Done is so much better than perfect. Everyday that I do it, means I’m becoming the type of person who does it. The more I show up, the more good stuff eventually will come.

You run an amazing podcast. How has your podcast helped your writing? How has your writing helped your podcast? Are there lessons you’ve been able to take from both paths and apply to the other?

It has helped so much. I’ve heard Seth Godin say “people talk about writers block, but no one talks about ‘talkers block’”. He’s so right. We overthink writing so much, but when we speak freely we don’t judge it so harshly and somehow we find the words. Having a podcast has been an incredible writing tool because I will transcribe the episodes which becomes a great jumping off point for so many things I write. I also find that the podcast is so much easier and I encourage anyone making content to consider creating one. It gives you a chance to work on ideas over an extended period of time. There are probably multiple books that will be born from it. What’s great is that unlike a book that is frozen in time, the podcast continues week after week, which takes the pressure off and allows me to keep figuring out what I’m trying to say and finding new ways to express it. As the months roll on I find that I have grown so much through the process.

Don’t Keep Your Day Job is your first book. What were some of the key lessons you learned that you might apply to any future writing projects?

Wow. I learned so much. It was one of the hardest things I’ve ever had to do. One of the hardest things for me was seeing the birds eye view. While writing chapter 4 let’s say, it was hard to remember if I had covered something similar in chapter 2 or if this would accidentally be repeated in chapter 9. I think I would stop and read the book front to back more often. I think I also would have put more of me in the book. I relied more on quoting insights from my podcast guests because I felt the readers would inherently appreciate them more. I think that was a mistake.

A lot of writers freelance but dream of writing full time. Can you share some of your top tips or recommendations from the book or podcast for those writers? 

We’ve had a few very successful writers on my podcast, who can answer that even better. Jennifer Weiner, Jen Sincero, Emily Giffin, Daniel Pink and the list goes on. I think there are a couple important steps. First we need to write a lot in order to find our voice and figure out what we want to say. Secondly, and this applies to any successful endeavor, we need to know who we are speaking to. Radical Empathy is the core of any successful venture. Seth Godin told me that and he’s 100% correct. We are built to serve. The difference between a hobby and a business is someone is paying us to do this thing because they value it. It means in a business that someone else needs or wants what we’re making. It’s critical to know your audience and I would say it’s wise to engage with them long before the book comes out. Know their pain points, build trust with them. Start a blog or a podcast. When we build that kind of relationship not only will our books sell better, but we’ll know what we’re really writing about and to whom. As we get feedback from our audience we’ll continue to serve in a greater way.

What books or writers have most influenced the way you think and the way you write?

Seth Godin, Neil Pasricha, Julia Cameron, David Aaron, Emily Mcdowell and Martha Beck. 

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