10 Questions To Ask Before Quitting Your Job

I quit my job 14 years ago to become a full-time songwriter.

Just a year after graduating from college, 1 year after landing a good paying state job, and a week before my wedding day, I turned in my resignation and leaped (head first) into the world of full-time creative entrepreneurship.

I want you to imagine, if you will, the countless wide-eyed conversations I had with family members, friends, ex-coworkers, and myself.  Everyone thought I was totally crazy… and to some extent I was. But, I quit. I followed my instincts, listened to my heart, packed up my career in social work, and quit my job.

Quitting a job to pursue full-time entrepreneurship is what people who have a crazy passion for serving, creating, making, cultivating, and building, do. We make things happen.

If I could travel back in time, back 14 years ago, I would give myself a list of 10 questions to ask before turning in that letter of resignation. Since time-travel isn’t a thing, I’ll list my questions here for someone who may be just like me and ready to make things happen.

1. | Why do you want to quit?

 Many businesses started with the phrase, I hate my job, but more is needed to sustain one. Leaving your job should not be based on how you feel right now. Feelings change. A new boss could land in your department next month and change the entire culture of the company. 

Something to consider: Your why should have more to do with what you’re starting and less to do with what you’re quitting.

What is your why? Why do you don’t to quit your job? Why do you want to build your own business?

2. | What problem do you solve + how do you solve it?

 This is an important question to answer no matter what industry you’re in. People buy/invest to find solutions. People listen to music, read articles, buy clothes, hire photographers, design homes, take vacations, and live their lives based on how they feel. Create services and products that is the answer to what keeps them up at night and moves them in a really authentic way.

Additionally, as awesome as you are (and you are so freaking awesome) their are more of you in the world. Many people may offer what you offer, but they aren’t you. How you solve problem should be inspired by you and your story…

3. | What’s your story?

 Did you even know that you have one? Everyone has a story. You have a story. I strongly believe that THAT is your superpower and it’s vital to your business. Because there are products and services everywhere, you have to stand out. Your story will help you do that. It’s what sets you apart. It’s great for marketing, networking, and creating community. 


Sharing your story is also a great way to be of service to others. You become someone that others can look to for inspiration.

4. | Have you checked your ego?

 Mistakes will be made, failures will happen, and some people will not want to buy what you have to sell. Your ego will make those realities harder to deal with if you don’t check it. In business (and often in life) nothing’s personal. Make your business less about you and more about what you have to offer the world.

Ego Check:

  • Create a mission statement that details the problem you solve and how you solve it. Keep that as your main focus.
  • Create an ideal client profile. Describe your ideal client in as much details as possible and refer to it when someone tell you “no.” Often, you will find that that person wasn’t ideal.
  • After every mistake or failure, create a Grow From It list. There is a lesson behind every mistake or failure. Look for the lesson, keep a record of it (you’ll need it later,) and grow from it.

5. | Are you prepared?

 I know you want to quit, but are you ready to quit? Have you done enough research? Do you have support? Do you have enough money to support yourself personally and to fund your business?  If you are not prepared, you have already failed. There is no way to predict the future of your business but there are many ways to prepare for it. A few things I wish I was more prepared for:

  • No’s (I still cringe when I get a “no” but I’m no longer discouraged by it)
  • taxes
  • marketing schedule and budget
  • networking
  • loss of friends (more on this later)
  • off seasons
  • less sleep (at times)
  • growth

6. | Are you willing to let go?

 This is important. You’re not just quitting your job, you’re letting go of something that has sustained your life. To remain focused, you have to walk away, let it go, and take it of your list of options. When times get hard (and they may) you have to be willing to dig in, not turn back.

Having an I can always go back to my old job mentality can knock your hustle. When you quit, let it go.

7. | What are you willing to give up

(and what are you NOT…?)

 Everything costs. There is always an exchange. Quitting your job to become a full-time entrepreneur is going to cost you something. Sacrifices will be made, but there are also some non-negotiables. Decide what they are and be honest about what you are willing to do (or not do.)

As a songwriter, the first thing I gave up was most of my sleep. While growing my business and expanding our family, I exchanged my weekly hair and nail appointments for swim lessons, and organic foods (because children are expensive.)

The one thing that I decided I was unwilling to do, early on, is give up my publishing. It was really important to me that I own my own music

8. | What do you expect to gain?

 Your sacrifice, your commitment, your hustle will payoff. But, everyday will not be easy. Knowing what you will gain if you persist is essential.  It’s a motivator. Get clear on what you expect. How many clients will you service each month? What is your expected monthly income? What kind of press do you want to earn?

Simply put: what will you get from what you do?

My personal method: everyday I write out my action steps in my favorite journal. Next to each action step, I write down the result I expect to gain. I call it my seeds and fruit.

9. | Will you do it alone? 

It would be great to have the full support of your family and friends, but the truth is they may think you’re totally nuts. Some people just won’t get it.

Support is great but it’s not guaranteed. Will you be able to stand on your own? Can you do this alone? This is crucial. You have to be strong enough to do it anyway. Your purpose in life will always rise above the opinions of others.

Here’s a tip for handling negativity: Check the source. More often those unsolicited opinions are based of the limitations of others.

10. | What’s next?

 Now that we’ve worked through the mindset stuff, let’s work that hustle. What are your plans? What is your next move? What do you need to do this week… over the next 2 weeks.. within the next 6 months?

When all of the hype behind quitting has worn off, you need a plan and you need to back that plan up with some action.

Quick tip: write out your next moves and ask the question: who can help me with this? Pulling together a network of people to support your effort will make the transition less daunting.

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