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When do I know it’s time to leave my day job?

When do I make my side hustle a full-time business?

These are some of the most commonly asked questions in my business coaching.

I wish I could that I could say that there was some magical formula you could dump into a program to give you a little reading and a date for quitting your day job, but it’s not quite as easy as that.

But I do have a six-point checklist that I think could really help you in making decisions in whether or not you should quit your day job to pursue that creative dream that you have.

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Six Questions to ask yourself FIRST

1. If you are someone who is married, and you’re considering leaving your day job, are you and your spouse in unity about this decision? The Bible says where there is unity there is a commanded blessing. Make sure your spouse is on board!

2. Is your day job actually preventing you from really being successful in what you want to call your part-time gig or side gig or side hustle? Is being tied up doing something else for eight hours per day really preventing that thing from going full speed? Then that’s a really great indicator that you may need to leave that day job soon.

3. Are you feeling completely double minded? I felt completely torn because there’s so much opportunity I just felt so conflicted because I would be thinking about both jobs and trying to figure out how to kind of juggle these things both in terms of hours and in terms of my energy. The Bible talks about the double-minded man; he’s unstable in all of his ways because we’re notmeant to be torn in two directions.

4.  Why are you staying at the day job? Are you staying for the wrong reasons? Are you staying out of fear? Guilt? For perks? Because if so, that’s not a good reason to stay.

5. Are you living in dread? Dread is a ridiculous emotion. I know any time I dread something my anxiety level just goes through the roof. It completely steals my peace and myguess is that it does for you as well. I love how Joyce Meyer says that dread is the kissing cousin to fear. They’re all very much related.

6. Are you stealing from your day job? I was guilty of this. I had started my side business on the nights and evenings, and I would literally sit and use company time to design my business cards, to Google things like beautiful textured walls and how do I make columns look like marble? I was using my employer’s time to build my side business. Remember the Golden rule, to treat others as you want to be treated.


In addition to the good indicators that you need to MOVE ON, I have couple other things that you need to make sure you have in place BEFORE you make the leap from full-time day job to full-time entrepreneur.

Before you quit, do THESE THINGS

1. I want you to be making some money already at your part-time gig or side hustle. I want all indicators to be pointing towards the fact that you have the potential to make up the income that you’re about to walk away from. You need to have a business name going and a Facebook page set up (I’ve got Facebook page tips here). You should also be working toward getting your first 1,000 followers on your Facebook business page. (I’ve got those secrets here.)

2. You need to have, what my friend Nicole Walters calls an “exit strategy.” You need to be thoughtful in this and your plan needs to include something like when it gets to X date then that’s going to be when I leave my day job or when I begin making X amount of dollars that’s b when I’m going to go ahead and leave a day job.

3. You’re going to need 20 seconds of just insane bravery. You’re going to make that decision to leave that day job and then you’re going to feel like a crazy person. But when you feel like you’re getting a message from the Lord to make the leap and all signs are pointing in your favor that this is going to be something that you can be successful at, you’re going to have to get so laser focused on tuning out the opinions of others and just paying attention to the lane
that God is asking you to stay in.

I know that every single day of the week I would rather bet on me and put all of my eggs in my own basket then to bet on somebody else who is employing me who could at any time cut my pay, cut my hours or cut my position, whenever they deemed necessary. And so listen I’;m rooting for you.

I have a new online course for creative business owners to help you get on track to growing your business online. Check it out here. There are many lanes out there to choose from … and this is the best roadmap to get there.

Blessings, Jen

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