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

Laura LeeLun
Jan 11, 2019 · 2 min read
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  1. Do I have enough savings to support myself during this transitional period?
  2. How do I utilize my transferable skills?
  3. Which of my friends are sufficiently glamorous to be in my entourage but bland enough not to draw attention away from myself?
  4. Do I need to hire a social media strategist or can I stick with the ten-year old from next door?
  5. How much body glitter is too much body glitter?
  6. Can I trust Aunt Susan to feed my sea monkeys while I’m on the European leg of my tour?
  7. Would Martin Scorsese be available to film the behind the scenes documentary of my European tour?
  8. 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?
  9. How long would it take to undergo hypnotherapy treatments to overcome my fear of heights?
  10. Would it be more cost effective to obtain T-shirt cannons from Bangladesh or Indonesia?
  11. 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?”
  12. Would it be worth it to lure away Katy Perry’s backup dancers even though we’ve recently ended our bitter feud?
  13. 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?
  14. Would it be considered self-indulgent to open a sanctuary for giraffes with cleft palettes even though it is my spirit animal?
  15. Would it be too soon to bequeath my office cubicle to the Smithsonian?
  16. 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?
  17. Do I risk overexposure if I star in a remake of Twelve Angry Men and play all the roles?
  18. How do I keep an eye on that obsequious ingenue who I suspect is trying to sabotage my career and take my place?
  19. 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?
  20. How do I sign up for COBRA?


Medium humor. Large laughs.

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Laura LeeLun

Written by

Comedy writer, member of Quick Pickle sketch troupe, co-host of Riff Raff Revolution podcast.



Medium humor. Large laughs.

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