My career as a writer and creator hasn’t gone exactly as I planned. But that doesn’t mean I’m not where I’m supposed to be.

Still, there are nights where I lie awake at 3 a.m. thinking the path I’ve chosen is crazy. Calculating the odds of breaking into Hollywood as a screenwriter. Running the growth numbers for YouTube, TikTok, and newsletter subscribers. Wondering what the big “break” is going to look like… and if it will ever come at all.

I get some comfort knowing this middle-of-the-night terror is common among entrepreneurs. The late Felix Dennis, founder of Maxim magazine, wrote about it at length in his book, “How To Get Rich.” And after four+ years of trying to build something of my own, I can confirm its validity. Fear comes in waves… often in the dead of night.

I think I’m writing about all this now because 1) I just had a week away with my parents and family to let my mind process all of this, and 2) I ran across this quote on X from Dr. Julie Garner that really resonated with me:

“It’s probably good that no one really knows what it takes to build something successful before they really take it on. Very few would start.”

That’s where I’m at. I’m just realizing how difficult it is to build something successful.

I’m not where I imagined I’d be by now and it’s frustrating. But, writing it out helps me work through that frustration. And there are some things I’ve learned that I think you will find useful if you’re taking the leap yourself.

So, here are some thoughts to absorb into your mindset if you’re preparing to live life on your own terms:

Table of Contents

• 1. Constantly try new ways to get what you want.

• 2. Don’t be too prideful to start at the beginning …

• 3. Fearlessly embrace new technology.

1. Constantly try new ways to get what you want.

I quit my job at the beginning of 2021 with a single goal: write a movie and get it made. Tara and I have now written two movies and two TV pilots, with nothing made. We’ve learned a TON that will come in handy in the long run (decades). But the reality is, we’re not where we want to be.

And a big part of that is because — just like the rest of the world — Hollywood has changed. Breaking in as a new writer with a great script is no longer the path. The internet has changed everything.

I see YouTube creators handed millions of dollars to make movies. I see TikTok talent get cast in TV shows. I see Instagram comedy teams land major brand partnerships. There’s a pipeline between internet talent and Hollywood that didn’t exist even five years ago.  

Now, you’re probably thinking, “well yeah. You should have seen this coming.” And as someone who’s been writing about the power of the internet for almost half a decade, you’re right. I should have.

But, as Nassim Nicholas Taleb says, knowledge often doesn’t transfer between domains. Meaning if you’ve learned a lesson in one domain, you’ll probably have to get burned again to learn it in another before it becomes obvious.

Well, consider this lesson learned in Hollywood.

So, Tara and I are once again trying something new: publishing comedy sketches on YouTube, TikTok, and Instagram (@thetarajoshi across all three). Here’s the path as we see it:

Step 1) build an audience (female, millennial skewing under Tara’s name) with short-form comedy content.

Step 2) Use that audience as leverage in Hollywood for money to make our larger scripted projects.

Once again, Tara and I are trying something new to get what we want. We are still writing movies because it scratches a deeper itch than short-form comedy can scratch, but we can no longer ignore the internet. Better late than never.

2. Don’t be too prideful to start at the beginning.

I’m a writer. Not a pretentious one (I write fart jokes regularly) but Tara and I take a ton of pride in our ability to write 100 tight, powerful screenplay pages that move the reader emotionally. Cause it’s fucking hard to do.

And having to start from scratch on the internet — knowing a handful of less talented but fearless creators are well ahead of us — making TikTok and YouTube videos smacks us right in the pride. But we’re doing it anyway.

And that’s what you have to do, too. You can’t be too prideful to be a beginner. If it’s important to learn, or crucial to your endgame, do it. Learn it. Forget about your pride. Kick your fear of embarrassment and failure to the curb and just try.

It’s like spending years climbing a brutally steep, dangerous mountain to the very top, only to realize it’s the wrong mountain. And now, to get what you want, you have to go all the way back down and start again at the bottom of a different mountain. It’s frustrating.

The good news is that you get to take with you all the experience and learnings to that next climb. Tara and I will forever know how to write a screenplay, which is a necessary skill to build the kind of career we want.

Take what you learn and keep hiking, even if you have to start at the bottom.

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3. Fearlessly embrace new technology.

Hollywood is about to undergo a technological revolution as AI touches every facet of the industry. From scriptwriting to post-production to AI video creation, there is no stopping it. There is no denying it.

Yet, some people try. Those who consider themselves “true artists” rally against AI and its place in the industry. Its place in creativity.

I’m not one of those people, if only because I’ve taken a quick glance at history.

Over the last 100 years, technology has always won. If it makes something easier to do, faster or cheaper, entrepreneurs will use it. And an artist IS an entrepreneur, at least in Hollywood. Because movies are made to make money. Yes, there is artistry, but it’s a business, and a big one.

So, don’t be afraid of new technology. Embrace it instead, and quickly. This is an advantage in a constantly changing, high-tech world. If you can stay with the tech curve, or with any luck, get ahead of it, you will be in the best position to get what you want.

My dad was one of the first people to embrace ChatGPT after I did. He’s 75-years-old. He uses it for everything, including learning how to make videos for TikTok and YouTube to promote his podcast, “Seniors in the Building” (send it to your parents or grandparents — it’s a podcast by four seniors who talk, think, and laugh their way through growing old).

If my dad can embrace all this new tech, so can we. It’s a massive competitive advantage in a world changing faster than you can say ChatGPT 4.5.

So keep going. Keep learning. And don’t stop. Thanks for reading.

-Thomas

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