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How This Former Lawyer Reinvented His Career in His San Francisco Apartment

“I think you should start your own law firm.”

Drew Amoroso’s boss called him into his office one day to tell him this. 

“Did I do something wrong?” Drew asked. They had worked side by side for over 5 years at Reed Smith LLP in San Francisco. 

He said, “No, I just think you have what it takes.” 

Drew dismissed it initially, but looking back later, he realized there might be something to what he said. 

Drew had grown up in small town Pennsylvania. After attending a liberal arts school in the state, he decided to go to law school at UC Davis so he could get out of dodge. 

His goal was to find a way to make money, and then figure out how to be happy later. 

Becoming a lawyer seemed like a good way to do that. 

After 6 years of working at Reed Smith, he eventually took his boss’s advice and left to start his own firm. Six months in, he started waking up with pain in his stomach, sometimes so intense he couldn’t get out of bed. 

“Maybe this being a lawyer thing isn’t for me,” he decided.

So he wound things up at his firm, and then proceeded to hide under the covers for 6 weeks. 

(As many of us who leave the law do at the realization of, “What have I just done?!) 

Then, for the first time in his life, Drew asked himself, “What is it I really enjoy doing? What actually makes me happy?” 

After looking back on his career, he realized the most rewarding times were when he was doing something similar to coaching. 

He decided to open a one-person coaching shop. 

He had all the typical thoughts people have who start their own business: 

Is this going to work? 

How am I going to do it?

How am I going to make a living? 

What will people think? 


On top of that, he had to make what felt like a huge identity shift. 

For 10 years, when people asked him what he did, he had talked about being a lawyer. When things shifted in his career, people would ask the same question, and he’d think, “I’m not sure.” It was really scary at first.

I asked Drew what it looked like for him on a practical level to figure out who he was and what he wanted to do. 

He started by clearing off an entire wall in his San Francisco apartment and put a big sheet of construction paper up. 


He wrote out these headings: 

What are the things that I enjoy about my work? 

Who do I want to help? 

What kind of lifestyle do I want to have? 

How much money do I need to make to fit that lifestyle? 


It was helpful for him to connect income to a goal because he’s not the type of person who just wants money. 

So he started by asking himself these questions, looking at the answers, and whittling things down. 

As he began reading more about startups, he learned that they’re companies that have a thesis about a gap in the market. The goal for them is to move quickly in order to fill that gap. 

So he thought, “What’s missing in the legal industry that I would enjoy pursuing or trying to create?”

Drew felt that lawyers needed a systematic way to be intentional and purposeful about their professional path. 

More than just coaching, he wanted to create a professional development ecosystem that would allow lawyers to be happier but also have a set of tools to help them navigate the challenges of being an attorney. 

So he started to form that in his mind. 

He made plenty of mistakes, but there were three things Drew did that really helped. 

  1. Finding a coach - In fact, Drew maxed out all his credit cards on 3 different coaches, one specifically for startup founders. 
  2. Networking - While the people around him were supportive, he could feel their nervous energy about the risks he was taking. So he had to reinvent his network and find other startup founders who could help him through the process. 
  3. Emotional Freedom Technique (EFT) Therapy - He found an EFT practitioner and started doing 75 minutes of EFT every week. This was absolutely instrumental in him working through his emotional hooks and baggage so he could grow. 


It wasn’t an overnight process, but it was getting up every day and putting together one little piece after another. 

Today, Drew runs the only coaching platform in the legal industry. He and his team of 5 employees are working on “future of work” things like moving towards a four-day workweek, and other really cool, innovative projects.

Instead of hiding under the covers, Drew wakes up each day excited about the work he gets to do. 


Where to Find Drew: 

LinkedIn: Drew Amoroso


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