Questions to Ask Before Quitting Your Day Job to Follow Your Dreams

- Do I have enough savings to support myself during this transitional period?
- How do I utilize my transferable skills?
- Which of my friends are sufficiently glamorous to be in my entourage but bland enough not to draw attention away from myself?
- Do I need to hire a social media strategist or can I stick with the ten-year old from next door?
- How much body glitter is too much body glitter?
- Can I trust Aunt Susan to feed my sea monkeys while I’m on the European leg of my tour?
- Would Martin Scorsese be available to film the behind the scenes documentary of my European tour?
- How much are my vintage, still-in-the-box X-Files action figures worth, and will it be enough to purchase a glass tank capable of bearing my weight?
- How long would it take to undergo hypnotherapy treatments to overcome my fear of heights?
- Would it be more cost effective to obtain T-shirt cannons from Bangladesh or Indonesia?
- Would it be in poor taste to make my former co-workers pay to see my Vegas-style spectacular that the New York Times calls “a cross between Houdini, Peter Sellers, and a more flamboyant Lady Gaga?”
- Would it be worth it to lure away Katy Perry’s backup dancers even though we’ve recently ended our bitter feud?
- Will my parents finally be proud of me when I sell out Madison Square Garden and am named one of People Magazine’s Most Intriguing People?
- Would it be considered self-indulgent to open a sanctuary for giraffes with cleft palettes even though it is my spirit animal?
- Would it be too soon to bequeath my office cubicle to the Smithsonian?
- Would I need FDA approval to sell my “negative calorie” lifestyle drink, or do I just hire a good lawyer and hope for the best?
- Do I risk overexposure if I star in a remake of Twelve Angry Men and play all the roles?
- How do I keep an eye on that obsequious ingenue who I suspect is trying to sabotage my career and take my place?
- If the worst case scenario occurs, and I am left without adoring masses, loving partner, and my pride, how will I pick myself off the floor and carry on?
- How do I sign up for COBRA?