Jenna Rainey


Course Login ➞

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.



                                              Take the quiz to get your flow back! 
Feeling creatively stuck?  
Let's be friends!

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



Building Good Money Habits for Your Business with Justine Lackey

Business Resources


written by




Building good money habits? How do I even do that? I know this is something evvveryone, including myself has wondered.

Any creative entrepreneur starting a business knows that you seem to acquire a dozen new job titles overnight—everything from copywriter to accountant. And if you haven't had any training in money management, the learning curve can feel daunting.

I get it. It's so much more exciting to be creating beautiful things than to manage your books. But developing and building good money habits is key to both the short-term and long-term sustainability and financial success of your business. Which, in current times with what's going on in our world, is so important!

Related Post: The Importance of Future Thinking in Business

Maybe you're thinking, I'll just outsource it. Even so, it's important to have a foundational understanding of what's coming in and what's going out. It helps you know who to hire, what questions to ask, and how to feel empowered (not overwhelmed) by the numbers.

Since I'm definitely not the expert on the topic, I invited Justine Lackey to the podcast. She is a 100% virtual bookkeeping company based in the NYC area. With 20+ years of experience, Justine's been featured on,, and in Women's Day magazine.

Justine is passionate about helping small business owners, entrepreneurs, and especially creatives position themselves for long-term success by taking control of their finances and implementing systems to maintain organization in their business.

Listen to this episode and I bet you'll walk away with greater confidence and actionable ideas for improving your and building good money habits.


Stellar insights

  • [06:50] If you're not ready to delegate bookkeeping services, schedule regular times in your calendar to focus on it. And automate repeated processes!
  • [09:46] There are tips for saving the right amount of money to avoid dangerous tax debt, which is one of the hardest lessons learned for freelancers and artists.
  • [18:47] QuickBooks online is a popular bookkeeping software with many helpful features like banking feeds and invoicing.
  • [21:24] Saving between 2-4% each month in a rainy day fund can give you a safety net and do wonders for your mindset.
  • [22:48] Don't forget about saving for outlier business expenses (i.e. business insurance) and keeping tabs on when those expenses are due.
  • [25:09] It's a good habit to educate your client/customer on your payment policies at multiple points in the sale process.
  • [32:34] Justine outlines her recommended checklist items for monthly and quarterly tasks and reminds us of the vital importance of collecting W9s for contractors.
  • [40:40] Justine decodes the commonly-used tax forms—EIN, DBA, W9, 1099, 1099K, W4, W2.


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 5: What No Ones Tells You About Being Your Own Boss
Episode 8: 5 of My Biggest Mistakes as an Entrepreneur
Episode 10: Legal Steps to Take When Starting a Business
Episode 21: The Legal Crash Course Every Business Owner Needs to Hear
Episode 28: How to Make the Right Hire



by Jenna Rainey 

add a comment

  1. Jessica F says:

    Super awesome and helpful information. I’m feverishly taking notes, playing back, repeat. When you are just starting a business, at what point do you hire an accountant? Or do you just start with software like Quickbooks?

    • Jenna Rainey says:

      It all depends on your situation, skills, background, etc. But I’d personally do it early on just because I don’t like doing bookkeeping and making errors on taxes can actually cost you money!

Leave a Reply

Your email address will not be published. Required fields are marked *

The Complete Beginner's Guide to Watercolor

Get a rundown of all my recommended supplies, learn fundamental techniques and tips including color theory and composition, and walk away feeling super confident with your new love of watercolor!

Free e-book

The Complete Beginner's Guide to Watercolor

Freebie Alert!

*Signing up will subscribe you to our email list, You may unsubscribe at any time, though doing so means we cannot contact you with more free, valuable education and tips on this topic. You also agree to our Terms and Conditions and Privacy Policy.