In a heartfelt letter to her 23-year-old self shared on Instagram, Corcoran wrote: “I know it feels like you’ve had more bad bosses than anyone in the world with those 22 jobs, but trust me, it’s not the end of the road.”

At that age, Corcoran would have been just one year shy of founding real estate company the Corcoran Group, which she built into a $6 billion business from just $1,000.

Reflecting on her journey to success, she detailed how waiting tables changed her life, her “best title yet,” and never taking no for an answer.

“Whatever you do, don’t take the first offer,” she concluded.

Your big break can come from anywhere—or anyone

You never know where your next windfall will come from—and that was especially true for Corcoran.

“That diner waitress job you’re busing tables for? It’s gonna change your life,” she wrote. “Trust me on this.”

It was there that she met a “handsome man” named Ramone Simone, who after dating for a year fronted the $1,000 the pair needed to launch a real estate brokerage company together. They split seven years later, but the Corcoran Group continued—and the rest is history.

“Keep getting back up even when your back’s against the wall,” she advised her younger self, as in the end she sold the company for a staggering $66 million in 2001.

Don’t forget to have some fun

Corcoran goes on to recall the ups and downs that come with founding a business and living life generally, including getting your heart broken and feeling like you’ve “hit rock bottom.”

“Along the way, you’re gonna meet incredible people, some not-so-incredible people, make connections, and learn the ins and outs of running a business,” she wrote. “It’s gonna be tough, but it’s gonna be worth it.”

Looking back, she wishes she had listened more to her old man.

“That guy knows how to have fun in life,” she explains, while adding that her dad insisted she have a “damn good time” while building the business. “He was right. Life’s too short,” she added.

Although the property mogul wishes she made more time for joy while growing the Corcoran Group, she eventually found that feeling while venturing on a new journey—motherhood. 

In fact, she tells her younger self that “Mom” will be her best title yet. 

“You’ll have the family you’ve always dreamed of. It’ll take more effort than expected, but those seven rounds of IVF will all be worth it,” the mother of two candidly shared. “Your heart will overflow with love!”

Never settle

When most people would start to wind down their career and think about retiring, 74-year-old Corcoran said she was cranking the dials of her working life up.

“Just when you think you’re slowing down in your sixties, this show Shark Tank will call you and change your life again,” she told her younger self, having previously revealed that she fought for her place on the show. “When they try to take the offer away from you, write that email and compete for your seat.”

Now, as Corcoran says, she’s a “fairy godmother to thousands of entrepreneurs.”

Ultimately, her reflective post serves as an important lesson to never settle.

“I won’t tell you how much we sold our business for. I’ll let you be surprised…but whatever you do, don’t take the first offer,” she ended the post. 

If you think more money would make you happier, Shark Tank star Barbara Corcoran has some bad news for you. Here’s why she is no happier now as a multimillionaire than when she was “dirt poor.”