Episode 371: Should I Quit My 9-to-5?

 
 
 

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Should you quit your 9-to-5 and start a business or build your idea while you’re still employed? 

For aspiring entrepreneurs, that question can feel HUGE. You’re craving more freedom, creativity, or control, but leaving a stable paycheck can feel like jumping off a financial cliff. 

But what if you don’t have to choose between playing it safe and burning it all down? 

In this episode of Workday Playdate, Erin shares a five-step approach for quitting your 9-to-5, starting a business, and making the leap into entrepreneurship with more clarity. Drawing from her own experience building improve it! while working a full-time recruiting job, Erin breaks down how to test your idea, understand your finances, involve your support system, and create a gradual path toward self-employment. 

Instead of asking, “Should I quit my job?” Erin invites you to ask a better question: What can I build before I leave? 

The “Stay or Go” Gut Check 

Before you hand in your resignation letter, it’s worth figuring out what you’re actually ready for. Erin shares a simple gut check to help you notice whether you truly want to leave your job, or whether you’re simply ready for something about your current work situation to change. 

Build Before You Bail 

You don’t have to quit your 9-to-5 before you start building your business. Erin shares how she built improve it! while working full time and why creating the offer, testing the idea, and taking those first steps before leaving can make entrepreneurship feel a whole lot less risky. 

Know Your Numbers 

A dream is exciting. Rent is real. Before making a career transition, Erin encourages you to get clear on your monthly expenses, income needs, and financial runway. Understanding your numbers can turn a vague “I hope this works” into a more informed decision about when you’re ready to make the leap. 

Bring Your People In 

Big career decisions don’t have to happen in secret. Erin explores the value of being transparent with your boss, partner, friends, and trusted supporters and how involving the right people early can make a major transition feel less scary, more strategic, and a lot less lonely. 

Make the Leap Less Leap-y 

Quitting your job doesn’t have to be an all-or-nothing decision. Erin explores how part-time work, freelancing, side hustles, and small business pilots can help you test entrepreneurship, build momentum, and reduce uncertainty before going all in. 

Start Small, Learn Fast 

You don’t need a perfect business plan to get started. Erin shares why building the smallest viable version of your idea, getting real-world feedback, and learning from what happens can be more useful than spending months trying to plan the perfect business. 

Your Freebie 

Take the quiz: What’s Your Leadership Style and Your Next Business Move? 

Find out how your leadership style drives motivation, and walk away with 3 specific ideas you can start building into your business right away. 

Workshop mentioned in the episode: Taking Initiative & Creative Risks


Connect with Erin Diehl x improve it! 

 
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Episode 370: When High-Achieving Women Carry Too Much Alone with Meghan French Dunbar