How to Know When to Quit Your Day Job

For many years, I worked two jobs trying to get my side-hustle off the ground. I remember telling my husband that I knew I could make my career in chairs fly if only I could focus on it without having to work my other day job. But looking back, I can see the issues and why it took me 6 1/2 years to quit my day job—but it doesn’t have to take you that long!


Here’s the 4 key questions I believe you have to consider when deciding to quit your day job.

  1. Who depends on me and how much money do I really need to make?
  2. How miserable am I?
  3. How determined am I to make this happen?
  4. Am I charging enough? Do I have the guts to raise my prices

First of all, quitting a secure job is a very personal decision. You have to consider who depends on you. Do you have kids or a partner who needs your income? How much do you need to bring in to provide for those people?  Or is it just you? I had two kids and a husband who depended on me bringing in my share of the income. I couldn’t leave them in the lurch to go off and do my passion job if I couldn’t bring in the money we needed. On the other hand, my friend Sara from Simply Southern Cottage was all alone. She needed to provide for herself and no one was going to help her pay the bills. Sara had to consider how much money she really needed to survive. I think we can all probably live on a little less if we wanted to make the sacrifice, but we have to also be realistic, too.

I have said this before, your misery has to outweigh the fear of the unknown. And there is a lot of fear when it comes to quitting a day job and relying on your income as a maker or a creative. By the time I quit my day job, my misery had grown substantially. But I still woke up in the middle of the night thinking, “What in the world did I just do?”  However, I couldn’t go on in my day job any longer…I was more miserable than I was scared.  And I would rather be scared than miserable. At least my fear would motivate me to take action.

I was determined to make this new career move work, no matter what it cost me. I worked weekends, nights, and did everything I knew. Then, when my own resources were depleted, I joined a business coaching group. I needed ideas, direction, and inspiration to get my creative business making more money. It was $2800 to join and I didn’t have the money in the bank, but I knew I needed to join this group to get to the next level. I had tried everything on my own, and I was stuck. I paid for it on my credit card and put some skin in the game. This investment motivated me to show up and do whatever was suggested. Because I did, I paid that debt off within two months. The benefits from that first coach changed my business and my life.

I was faced with the reality that I had to raise my prices in order to make money. Pricing is the biggest problem that creatives have. We don’t believe anyone will pay the amount we need to make for products. As a creative, you have to value your work and your time—if you don’t value these things, no one else will. (It helps to get a little mad about it, too.) It takes guts to raise your prices, and it’s a necessity if you want to make any money. Otherwise, face the fact that you are working for free and you’ll never be able to quit that day job. You HAVE to raise your prices. I often say that when a product doesn’t sell, raise the price and see what happens. It’s about perceived value…higher prices make your products more valuable to buyers.

The bottom line is if I would have had the courage to raise my prices earlier, I could have quit my day job earlier. I didn’t need to take 6 1/2 years. So let me be the example for you…raise those prices. Get determined and put in the work to get your business off the ground. Get some skin in the game and invest in a mentor, business coach, or a business retreat. It will change your business and your life. Take some action!

This past year Sara and I hosted two retreats for women who own creative businesses (or want to own them!). For each one, the 3-day retreat was life-changing for those who attended. Sara and I hold nothing back…we are accessible and open with all our financials, strategies, and ideas. If you are interested in taking your business to the next level, PINK Creatives is enrolling for our next retreat April 12-14, 2023 in Round Top, Texas. You won’t believe how much you can accomplish in just three short days. Click here if you want to find out more.



I'm Wendy Conklin, The Chair Stylist.

What brings me joy is helping others live more creatively. I design antique-inspired, boutique chairs, and I teach others how to do what I do. Check out my shop, services, and courses to bring more whimsy into your home and life!

Check out my online courses to spark your creativity and upgrade your joy, starting today!


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