If You’re Feeling Insecure About Your Career Goals, Here’s Some Inspiration—Issa Rae Tweeted Her Future 10 Years Ago

Issa Rae speaks on stage at the Teen Vogue Summit 2019 on Nov. 2, 2019, in Los Angeles.
Issa Rae speaks on stage at the Teen Vogue Summit 2019 on Nov. 2, 2019, in Los Angeles.
Photo: Rich Fury (Getty Images for Teen Vogue)

Ten years a slave to social media one-upping, another decade is wrapping up, y’all! Like we always do at this time, many people turn to Twitter, Facebook, and Instagram to reflect on the past year they’ve had.


Did I actually follow-through on those New Year’s resolutions? Did I read those 52 books a year? Did my vision board manifest in reality? Is George Zimmerman still alive? These are the questions we ask ourselves every year. Since 2019 wraps up the end of a decade, that means the reflection’s weight is much heavier. That’s 10 whole years to see how much you’ve evolved as a person.

On Friday, omnipresent creator Issa Rae posted a tweet with “beginning of the decade,” referencing an old tweet she wrote, “Still pretty livid that I’m working this weekend. In 2010, I will take the necessary steps to work for MYSELF.”

And the rest, as they say, is history.

Following the debut of her hit TV show Insecure, Rae established herself in Hollywood as an actor, beauty ambassador, producer, radio executive and more. If you’re like me and follow the trades (i.e. Deadline, the Hollywood Reporter, Variety, etc.), not much time goes by without learning about a new Issa Rae project. The woman has her hands in everything! If I had to count the number of times someone on the Root Staff asks, “Does Issa sleep?” I wouldn’t be able to enjoy my weekend. Shit, she even co-owns a coffee shop / workspace for the people!


Ten years later, Rae is on her big boss shit right now, indeed.

Bringing that same energy, other notable folks in the industry reflected on their humble decade beginnings, as well.


In 2010, Matthew A. Cherry tweeted right after he mailed in his application to a director’s fellowship. Look at him now—he’s over here garnering millions of views for his new animated short and directing primetime television (for the very network that hosted the fellowship he applied to), no big deal!


In 2009, Lena Waithe tweeted she’d be “running things.” Whoop, there she is, doing just that. Waithe is now an Emmy-winning writer, a creator of several television shows, and currently promoting her newest feature film, Queen & Slim.


Now, I want to point out something important here: These types of tweets are not meant to discourage you or make you feel bad about your own progress (or lack thereof), especially if you’re aiming to dive into the ridiculousness known as “Hollyweird.” Though talent and (arguably, more so) persistent hard work are legit factors, sometimes this shit boils down to being in the right place at the right time (and by extension, “who you know”). Some folks call it luck, others call it fate. Regardless, there are factors beyond your own ability and talent that certainly contribute to success.

The real point of these tweets is for reflection and the powerful perception of hindsight. Ten years ago, I’m sure Rae had doubts and frustrations about the dead-end job she was working and had big creative dreams and goals. She may not have ever fathomed the boss-ass career she has now, so looking back at how far she has come is natural.


Alas, we’re about to embark on the series finale of the 2010s and need to gear-up to binge-watch (or binge-experience) the 2020s. Y’all ready or nah? If so, drop a prophetic affirmation in the comments so you can reference it at the end of the next decade.

Staff Writer, Entertainment at The Root. Sugar, spice & everything rice. Equipped with the uncanny ability to make a Disney reference and a double entendre in the same sentence.



All the good feels in the world won’t change the fact that there is no real job security or employee protections in America and that luck plays a huge part, not just skills.

But mostly, it seems knowing the right people plays the biggest part in American success.