“Courage is the mastery of fear, not the absence of fear..”

-Mark Twain


When To Leave The Day Job

Suppose you’ve been in the service industry, or mid-career in a job you can’t stand, or you’re simply putting in time ensuring you have the capital to fund your real passion. How do you know when to make the full transition? The most important thing is to have a plan: if you were planning for a vacation, you’d have a budget, a timeline, an idea of your basic costs and overhead and necessary savings/potential earnings. Well, now you’re planning for the vacation of a lifetime — so follow the same basic format. Map it out and follow it.

A good rule to follow is: once you are earning as much as your full-time job, (or you are well on track to doing so, once you have the full-time opportunity to dedicate to it), and especially if you are running out of evening or weekend hours, that is the time to stop rowing two boats.

While you’re building your business and waiting to achieve a full-time transition, find out what your options are with your current employer. Can you take gradual leave, work part-time, or take temporary time off just to be sure? The transition is going to largely depend on what kind of job you’re leaving behind. If it’s a fantastic government job with plenty of benefits, holidays and a huge salary, you may want to look into those benefits and see if you can take some kind of year-long sabbatical to explore your business options. This means you still have a safety net, and a guaranteed way to return if things don’t quite pan out the way you’d planned. On the other hand, if you’re in the kind of job that just requires sufficient notice for your boss to replace you with another warm body, make that phone call or write that formal resignation letter after you’ve carefully outlined your transition plans. It’s not like you can’t find another job (or return to the same one) if you really need to.

Try to leave on good terms, of course. You will want to keep as much goodwill as you can because you own a business now and word of mouth and reputation are important! Your old employers or co-workers may become your most eager customers or promoters.


Knowing when to leave my fulltime employment was one of the most difficult decisions I had to make. You need to make a plan for it — just like one would make a plan to take a trip to Hawaii. You need to start planning a date to leave your day job and how you will do it!