As a former entertainment exec who’s worked on a lot of creative projects, I love offering advice to creative people because I know the business side of things. Alessandra is one of the first creative people that came to me for advice and this is what went down…
Alessandra: I want to be a standup comedienne. Is that crazy? My mom thinks it is. My dad won’t tell me what he thinks. (Probably because I don’t know him). What do you think?
THIS IS WHAT I WANT TO BE WHEN I GROW UP

Lindy: Do you JUST want to be a standup? Because to be a standup, you do shows or open mics EVERY night, you go on the road, you probably spend some nights lonely in a motel room…(kidding)
VERY LONELY IF YOU'RE CHECKING IN SOLO:

Alessandra: Um….well if you put it that way, I just want to be everything—an actress, writer, standup, artist…doctor, astronaut, princess, video game character, a hero...(that seems easier, right?)
CAN'T I JUST BE THIS FOR MY CAREER?

Lindy: It’s really difficult if you’re "multi-talented" because when you’re first starting out, you need to be FOCUSED. You can start as a standup, and if you are good, it can lead to you becoming an actress, maybe an Emmy winner, then a multi-millionaire. But, you have to limit yourself first to get to where you want to be in the future.
A GOOD TIP:

So, for example, if you’re able to secure a position as a writer on a cable show, then grab it. Maybe down the line, as you achieve more success as a writer, you’ll be able to crossover into acting. At that point you’ll have a stronger base and may be able to branch out into other areas. That’s what Conan did. But in the very beginning, I’d recommend grabbing any really great opportunity that is closely related to your talents.
Alessandra: So do I look for a job in the business or find a day job that gives me more time to develop my talents? Because right now, I don’t think I have one specific solid talent and my job options are: preschool teacher or entertainment assistant.
I DON'T WANT TO HAVE TO ANSWER QUESTIONS LIKE THIS:

Lindy: It’s a good thing you know that you haven’t developed one specific talent yet. So, you might want to go with a more relaxed day job during the day to work on your comedic skills at night. At the same time, if you find a day job SPECIFICALLY connected to writing in the business, go with that. I always say, stay IN the business, on the creative side. There are pros and cons to both.
If you venture into assistant territory, you’re talking about a 24/7 position. There are a lot of demands on you and your time, and little time for you to spend writing a spec script or auditioning. However, if it’s the right assistant position, it might offer you more networking opportunities than working at a preschool. On the other hand, the preschool position offers more flexibility and time to hone your skills as a writer, and get material in the pipeline. At the end of the day its about the job, how happy you’ll be, how much money you need to live on, and of course the priorities in your life.
Alessandra: I’m thinking I’ll stick to assisting little kids, NOT adults.
GIVES ME TIME TO WRITE ON THE SIDE:

Lindy: That sounds like a plan.
Alessandra: So, in the end, I learned that having a day job in entertainment CAN take away from my time to work on my own creative material. BUT, there are awesome networking opportunities to having an entertainment day job, which can lead to a more focused career path. The only way an entertainment day job would be fruitful, however, is if I have material to show my employers. So, I better start cracking the creative whip!

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