Embrace the Uncomfortable: How Pushing Your Limits Can Lead to Success

Growing up, I freaking LOVED everything dark and gritty.

I was a kid, and thankfully life was easy. (or, in financial terms, I was someone else's bill!)

So stuff like Preacher (the comic, not the show), Ender's Game (the book, not the movie, 28 Days Later (the movie, not the...not movie?)

I ate that shit up.

And then, if I'm being honest, as life got more challenging, I shied away from that stuff.  

Law school was a huge time suck, opening my own firm was a struggle, and becoming a dad REALLY changed my world in ways I had no idea about.

I'm not a massive fan of the Chris Nolan Batman movies, I didn't enjoy a bunch of Quentin Tarantino movies, but the first 10 minutes of UP gets me EVERY. TIME.

(Game of Thrones is probably the one exception that proves this rule)

For a long while, dark and gritty just wasn't the escape I wanted, so I changed my habits.

Hell, I even read some of the YA novels in my mid-20s. (For the record, Divergent is a MUCH better story idea, but Hunger Games is much better written...and I never tried anything Twilight).

To this day, I cannot watch Handmaid's Tale because it's TOO accurate to modern life...

But, I can happily share that my life has returned to being in such a better place over the last 3-5 years and that I am finally on the dark and gritty train again.

I REALLY enjoyed Zack Synder's 4-Hour Justice League, and the John Wick movies are awesome, etc.

And last week, I watched The Bear. And I have to be honest, I don't recall the last show I enjoyed as much that made me so damn uncomfortable.

Without spoiling anything serious from the show, it gets into the grit of Chicago, and the darkness of running a restaurant, with a bunch of scenes crammed into a small (and I assume super hot) kitchen, and it doesn't let up.

It made me SO uncomfortable but in such a fun way.

And it made me realize that's where I found a lot of this semi-recent success.

Because I got out of my fucking comfort zone.

  • It was EASY to stay referral driven and have a $500,000 or so a year firm.  
  • It was EASY to keep changing shitty marketing companies that weren't a good fit for me.  
  • It was EASY to not stay on top of my systems and processes and get anal about trying (emphasis TRYING) to be the best at what I do every day.

But you can only coast downhill.
So if you want to stay on top, you must keep getting uncomfortable.
Learn a new skill.
Try a new hobby.
Say yes to the next opportunity - maybe you'll fall in love with Zooey Deschanel!
I freaking love the Anthony Bordain quote (or, to be fair, maybe he didn't say it... but it's still a great quote):
"Eat at a local restaurant tonight. Get the cream sauce. Have a cold pint at 4 o’clock in a mostly empty bar. Go somewhere you’ve never been. Listen to someone you think may have nothing in common with you. Order the steak rare. Eat an oyster. Have a negroni. Have two. Be open to a world where you may not understand or agree with the person next to you, but have a drink with them anyways. Eat slowly. Tip your server. Check in on your friends. Check in on yourself. Enjoy the ride."

Shake it up a bit.

For your law firm:

Try a new marketing tactic.

Post that video you've been hesitant to share.

Finally pull the trigger on that hire that you have been wish-washing on.

I'll be honest - maybe you’ll fail… but if you do, so what?  Figure out why it failed and you’ll learn for the next time. (coming soon in a future newsletter after I finish this amazing book.)

Maybe that uncomfortable moment now will help you later.

I have a friend who was a Jehovah’s Witness - and she can cold call like a mother fucker - because she: 

  • Had the door slammed in her face, 
  • Got cursed out 
  • Got the sprinklers turned on her
  • Etc.

So now, what the fuck are you going to through the phone that upsets her?  (and to be fair, we CANNOT and should not cold call...but I hope you get the point here).

Sometimes you need those hard moments to become the person you were meant to be.

Or shit - maybe you'll succeed!!!

So if you're looking for permission, here it is:

If you're stuck on some other limiting belief, I am here for you - just reply to this email and we can chat.

Otherwise, until next week my friends!  May you not get sassed by a 10 year old Princess you're supposed to save from kidnappers.

Until Next Friday,

Jordan Ostroff

Upgrade Your Life.

Okay, so this all sounds good, but you’re wondering how to start making these changes. The first important step was visiting this web page, so congrats! You’re already on the right track. The next crucial step is booking a consulting appointment with me so we can come up with a plan and replicate the results of so many others before you.

You can book an appointment here. See you soon!

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