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Should I Quit My Job? How To Know When It's Time.

Updated: Oct 29, 2023

I have had the absolute joy and frustration of being a self-employed entrepreneur for the last 10 years. If you are new here and don’t know much about my background, I am a working, camera carrying wedding and portrait photographer, national speaker and teacher and have been since 2009. I have gone through, both, the ups and downs and heartaches and joys of running a small business and in all of the years that I have been working in this field, the most asked question I get from those, both working in the field and not, is “how do you know when it’s time to quit your job?”

I wish that I could say that there was a magic timer that went off when “enough was enough” and you were clear for take off to pursue your hobby as a reliable, sustainable source of income, but entrepreneurship doesn’t work that way and so much of it is really subjective. The truth of the matter is: ONLY YOU will know when it’s time to make the leap and ONLY YOU can decide when the time is right. I have known people over the years who are talented creatives who had all of the makings of a talented business person, but who leapt and failed and I have also known those same types of people to not leap and to keep at their business while working another full time gig. I have also known the opposite (and I fall into this category), people who with no plan decided that the only way to live was free and as their own boss, and with no real strategy they jumped and they learned how to fly. At the end of the day, whether you continue working a traditional job or decided to march to your own beat, hard work is the only way to find success. If you are a little less willing to leave it to a “feeling,” here are some things to consider or to look for before jumping full time into the self-employment deep

  1. When your hobby gets in the way of your full time job. If working on your hobby requires more time then you can allot for it outside of your day to day job and you find yourself needing more time to keep up with paying clients and you wonder what life would be like if you could do your hobby or side hustle full time, if it would take off if you just had more time.

  2. When you’re making enough money to support your full time salary/ family’s needs. I highly recommend writing down your expenses, needs and wants and getting a number in mind for what you expect to make from your hobby/side hustle. If you can support your financial goals with the hobby and meet that fiscal goal solely from the work you are doing that is a sign that you are lucrative.

  3. If you are desperately unhappy in your current situation. If you wake up every morning and really struggle finding purpose in the work you are currently doing. If you think about your hobby/side hustle more than anything and feel really unhappy and unfulfilled in the work-place, it might be worth transitioning. I am a firm believer in living your life daily as if it's the last and I don’t believe showing up to a job that makes you miserable is what the Lord intends for us. I believe we are called to operate in our gifts, we don’t always get the opportunity to, but I do believe that’s the goal and the call.

  4. When YOU feel ready. If you feel you are ready to pursue your hobby/side hustle, trust that feeling. You know what you are willing to do and just how far you are willing to go to get to your goal, so if you feel fit to go after it, do not waste anymore time. Just do it and figure out the puzzle as you go.

Now most people probably wouldn’t co-sign number four, especially those who are conservative and a little more cautious in their decision making and I totally get that, but what I have learned is some of the best things in life aren’t always spelled out when we decide to take a chance and it's that little something in us that goes “ I think I can” that is the match that lights the flame to victory. When I quit my job 10 years ago, at 27 years old, it was a decision that I had to quickly make. I was scared. I knew I had potential and that I was on to something with this photography “thing,” but I had never seen entrepreneurship done so I didn’t have a road map for what life could look like. I wanted to cling to stability although everything in me knew I needed more from my life. I remember being at a women’s conference and sitting at a table surrounded by friends when I said, “I am going to quit my job on Monday and give this photography thing a shot and if it doesn’t work out, I can always go back to work.” Well friends, with no plan, no strategy (which I don’t advise) and no savings, I quit that next Monday, and I have never looked back. 10 years, two kids, bringing my husband home, and several other small business ventures under the umbrella of my photography business, including this blog that you are reading, we did it, we are making it and we are still here. So trust your instinct. It is a guiding force.

And let me just add, there is NOTHING wrong with working for someone else. There is such a stigma these days about working for “the man,” but there is such peace knowing that when you clock out, that the work is done.

So the question is, “how do you know when it’s time to quit?” You don’t know. You just trust and take it one step at a time and as long as you keep stepping you’ll be okay.

With strength, courage and wisdom,


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