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Don’t Keep Your Day Job: Tips For Taking Your Side Hustle To The Next Level

I met Cathy a while ago when she interviewed me for her podcast Don’t Keep Your Day Job where we talked all about executing your vision, defining your formula & cultivating a community.

Cathy is a real hustler & not only a podcast host, but a career coach for entrepreneurs. She actually started out in the music industry which is super interesting. Oh, did I mention she’s also the author of a book all about turning your passion into your career? Like I said, a real hustler.

Cathy is someone who I thought would be great to speak to The Skinny Confidential community. In this post she spills all her tips, tricks & advice for taking your side hustle to the next level. You’ll learn how to leave your day job effectively ( in a smart way ), traits that successful entrepreneurs have, & things you can do RIGHT NOW to get on the path to quitting your day job. Plus, she’s a big fan of launching what you have & adjusting to consumer feedback, which Micheal & I are big advocates of- but Cathy gets into it.

I think this post will really resonate with a lot of you being in quarantine with a lot of you wanted to start or expand your side hustles.

With that, let’s welcome Cathy Heller to the blog.

Tips For Taking Your Side Hustle To The Next Level

Introduce yourself & tell us your background.

Cathy Heller: Hey, my name is Cathy Heller. I’m the creator & host of the top ranked podcast Don’t Keep Your Day Job. I love coaching artists & entrepreneurs who want to add their color to the world through their creative gifts.

I started my career as a singer/songwriter & got dropped twice from a record label. Eventually I found my way into licensing my music to ads, TV & films & made a six figure income from it. Other indie musicians asked me to help them so I created a licensing agency, which then led to teaching online courses & then the podcast.

Then two weeks into the podcast a lit agent from Macmillan contacted me – & now Don’t Keep Your Day Job is a book! The podcast is on track to hit 15 million downloads this year & I basically get paid to talk to people like Jenna Fischer from The Office, blogger Seth Godin, Barbara Corcoran from Shark Tank, Howard Schultz from Starbucks, your very own amazing Lauryn Evarts & Michael Bosstick, & so many more amazing successful people. It’s nuts to look back on all of this. I feel so blessed to have the community & meet people every day who say I’ve inspired them to go make a living doing what they love.

 Why shouldn’t someone keep their day job?

CH: A friend once told me, “The opposite of depression is not happiness. The opposite of depression is purpose.” Too many people live quiet lives of desperation. I fully believe it’s because they’re not waking up every day doing what they are meant to do to help other people feel seen. That’s all we really want –  to feel seen & make another soul feel like there’s someone out there who gets them. If your day job doesn’t fulfill this need, if your day job doesn’t let you live life on your terms or allow you to do what you are made to do, then it’s time to make a change.

I tried so many day jobs after getting dropped from a label. I tried working at a nonprofit, in a casting agency, in a doctor’s office, real estate, interior design…I felt like Barbie, wearing different outfits – but none of them lit that fire inside. It was soul sucking.

One day I was feeling so hopeless & desperate, I had to pull my car to the side of the road because I was crying so hard. That day, I told myself “Enough is enough. I can’t do this anymore. This has got to change.” Thank god I did. When I talked to the TEDTalk speaker & author Daniel Pink, he said “If you have something that you think benefits the world, I think you have a moral obligation to try to bring it to people.”

It’s our duty to make our contribution. Too many people live quiet lives of desperation. The stakes are too high to waste your life away & not do what you are here to do. Every person on this planet really just wants to feel seen. You have that ability.

 How does one get out of their day job effectively?

CH: I would encourage people to grow a side hustle that they’ve tested & validated before they quit their day job. You need to know that this has legs & people will pay you for what you have to offer. I like to use the metaphor of building a runway instead of jumping off a cliff.

First you have to figure out who you’re trying to serve & be super specific. If you try to serve everyone, you end up serving no one. Then you have to find out what they desire most, what their biggest pain points are, & once you have that data you can start making a messy, imperfect prototype of the product or service that would help them solve the problem they have.

Then you take your messy version to them & say, “What do you think about this thing? What do you like about it? What could be improved? How much would you pay for something like this?” As you get the feedback, you implement it & keep tweaking until it’s an iteration that they will pay for. In the meantime, you should also give away free content to your audience, whether it’s a blog, a podcast, cheat sheets, or posts on social media. You need to show up for them & be generous. It takes a few deposits before you can make a withdrawal. Once you know that your offer can generate sales, maybe you can ask your boss to go part time so you have more time to build the side hustle. 

What are 3 tips you would recommend to anyone at a 9-5 right now who wishes they were doing their own hustle?

CH: Be messy. Don’t wait until you think you’re “ready.” You don’t have to be perfect in order to start & make a difference. ( Trust me, this is coming from a C student who almost didn’t graduate high school. )

Clarity comes from action. Lots of people have multiple things that they’re curious or passionate about, & they get overwhelmed by all the options. But you can only figure out what works & what truly lights you up by doing

The best thing you can do for another person is make them feel seen. As Seth Godin says, it takes a radical amount of empathy to be a success. Whatever you put out there, it should reflect what your audience is feeling & make them say, “Wow. That person totally gets me.”

What would you say to a single mom who has to work but is really passionate about her side hustle?

CH: I give so much credit to any single parent who will give themselves the permission to go for what they want, even when they have a million things to juggle on a day to day basis. I would say carve out any time you can to work on your side hustle. Make it a must on your to-do list. It can be even 15 minutes a day. You’ll be amazed how much you can get done when you’re doing something that you love.


What’s the biggest mistake you see people make when they quit their day job?

CH: They haven’t validated their idea yet, so they don’t even know if they can make money doing this thing. Then they’re extra stressed because they have no money coming in & they feel like a failure when in reality, they just didn’t do enough testing.

When it comes to successful people what have you seen across the board that they do differently than unsuccessful people?

CH: They have the courage to do it scared. Everyone walks in this world with fear. The ones who rise above the rest are the ones who dance with that fear & take those scary steps anyway.

What are some tangible things someone can apply to their life right now if they’re reading this at their job but dreaming about their side hustle?

CH: Set a benchmark & a deadline for yourself. Maybe you want to sell 20 things on Etsy by the end of this month, or launch your blog in two weeks. Turn your side hustle on things you are passionate about. Whatever it is, give yourself that end destination & then work backwards to figure out what you have to do between now & then in order to hit that goal.

Talk to us about time management.

CH: People tell me constantly, “I would love to turn my passion for baking or photography or music into a career, but I have a day job & a family & a dog – & I just don’t have time!” But guess what – it’s not about time. It’s about your energy. We all know how much battery life is left on our phones but we don’t do that for ourselves. So figure out those things that charge your personal batteries. It can be a podcast, a playlist of your favorite songs, a morning walk or meditation. Set yourself up so that when it’s time to dig into the work, you’ll be like a well-oiled machine & you won’t need hours & hours to get it done.

What are some tools you use to keep your business organized?

CH: I’ll be honest – organization is not my strong suit, but my team & I use Voxer to chat about everything that’s going on in the business. 

Tell us about your book.

It’s a collection of the best pieces of wisdom, anecdotes, & practical advice from what I’ve learned on my own journey & from successful creative entrepreneurs & experts I’ve had on the show. There are chapters on things like building your audience, growing your side hustle, giving yourself permission to explore, finding clarity, owning your worth, & a lot more.

Where can people find you?

CH: Come say hi on Instagram @cathy.heller! I read all my DMs & respond to as many as I can. You can also listen to my podcast Don’t Keep Your Day Job wherever you listen to podcasts. Also the book is on the major booksellers like Amazon, Barnes & Noble, Audible, iBooks, etc.


Hope you guys loved this post & picked up some tips & inspo if you’re thinking about taking your side hustle to the next level. Be sure to check out Cathy’s podcast & book for more amazing tips.

x, lauryn

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