When to Quit Your Day Job


Lately it seems like everyone has been sending me articles on the risk of quitting your day job to follow your dream. My book of choice recently, Big Magic by Elizabeth Gilbert, mentions that you shouldn’t give up your steady income to pursue a writing career until it is definitely bringing in the cash. Ms. Gilbert waited until Eat Pray Love was a huge hit before she left her publishing job. Her reasoning was: struggling to put food on the table or a roof over your head can put more pressure on you and limit creativity. Hm, that is food for thought for sure. If it is your side hustle, then how do you ever really make it big if you are not working on it full time? If you put everything on the line, and are all in, aren’t you more likely to be aggressive, driven and stop at nothing because there is no plan b? Well, maybe each profession is different. As a writer you can work late nights, early mornings and weekends on your book, while having a full time job.  Other start up businesses may need round the clock attention with 15 to 16 hour days. Unless of course you’ve figured out the 4 hour work week, which bravo, I am all about and do believe it can exist.


Personally, I am about to sell my third health club after being in the industry for over 30 years, yikes. My club, Weston Fitness in Philadelphia, was open for 17 years and there wasn’t a day that went by when I didn’t feel truly blessed. We touched so many lives and our members touched mine. Although the timing is perfect and other doors are opening wide, it still is a very difficult transition.  

As far as what I will be doing, well, I have two other businesses. One of them is managing fitness centers, with my business partner of many years and the other, SJW Productions (my side hustle), which I am extremely passionate about.

So, what to do, what to do…I could continue on the easier, more financially stable road or I could take the riskier road. Well here is what I decided: I am going to make the big leap and sell the managing company to my partner and go all in with SJW Productions. Now maybe you understand why everyone is sending me those articles.

Well here my thoughts on the subject and hopefully some guidelines that will help you make your decision on your individual, unique journey. It is also worthy to note that I have been an entrepreneur for a very long time - I know what I am getting myself into, sort of. I have been through many ups and downs, turn arounds, bumps, lumps, and setbacks, but I have also loved every minute of it and feel like the luckiest person in the world. Here is my disclaimer though: I am a true optimist and will always see the sun peaking out of the clouds.  I believe in people even when they don’t believe in me and when self-doubt sets in, I just smack myself and tell myself to get it together.

So here we go, my guidelines on when to quit your day job:

  1. Know yourself and your personality. You know your comfort zone and what works best for you. Push yourself slightly out of that comfort zone.

  2. Surround yourself with a posse that believes in you and will push you forward on the days you just can’t get motivated - friends, family, coaches, business teams, doesn’t matter, aim for five solid ones. These are not just “yes” people, but people that want the best for you.

  3. Have a well thought out plan with real goals. You don’t want to quit your job without having a clear picture of what you want to do and how, just because it is cool to be in business for yourself and everyone else is doing it.

  4. Find a mentor, at least one. Someone who already is where you want to go. Age doesn’t matter.

  5. Seek knowledge. Look, learn, absorb, take it all in. Always listen, doesn’t mean you have to do it, but keep an open mind.

These are all things that you probably already know, but now and then we need reminders.  

Oh! I almost forgot the golden rule: treat people how you would want to be treated. Don’t separate who you are and your values and say (the most dreaded words to me) “business is business”. Honesty, trust, acceptance, kindness and gratitude should be found everywhere and in everything you do.

Sandy Weston