Josh Garber is a University of Pennsylvania Law School grad and a full-time UpCounsel freelance lawyer.

He started his law career the traditional way: Josh graduated from a top law school, began working at a big law firm and then went in house at a tech company. But in 2015, he made a radical change and became a freelance attorney.

Why did a graduate of a top law school decide to nix the traditional career path? Josh told me why he became a freelance lawyer and what being his own boss has meant for him. Hint: In the last year alone, Josh has practiced law from Tulum, Cabo, Scottsdale, Los Angeles, Turkey, Greece, Puerto Vallarta, Medellín, Bogotá, Cartagena, Chile, Denver, London, Turks & Caicos, Lisbon, New York, Hong Kong and the Philippines.

What factors led you to become a freelance attorney?

My decision to become a full-time freelancer was kind of thrust upon me. I graduated law school in 2009, at the height of the economic recession, and had a lot of job instability. In November 2014, I was hired as a contract attorney at a law firm. In January 2015, that same firm basically fired and rehired me on the same day.

That day, I decided to open up my own freelance business on the side, so I could bring in extra income and have some stability in case I was let go again.

When did you decide to make freelance work your sole focus?

My second freelance client ended up hiring me full-time, but ultimately it didn’t work out, and I didn’t have another job lined up. So, since March 2016, I’ve been freelancing full-time, and it’s been the best experience I’ve had so far in the workforce.

What do you like about freelancing?

One of the reasons I love it is the flexibility of work hours. I am able to wake up and get right to work, rather than having to shower, get dressed, get coffee and have small talk. It’s much more efficient for me.

Additionally, I am a night owl and don’t function best in the mornings, so freelancing gives me an opportunity to work when I am most productive.

By only working when I am most productive, I’ve found the the amount of time per day that I actually work has gone down drastically. I usually work approximately 5-6 hours a per day, but the result is almost exactly the same as when I worked longer under less ideal conditions. This affirms my belief that the 9-to-5 (or worse) system of working is broken.

My schedule as a freelancer has also allowed me to focus more on my physical and mental health, and I’m the happiest I’ve been in a long time because of it. By making my own schedule, I now make sure to schedule time to go to the gym (almost) every morning and am in the best shape of my life. It’s really done wonders for me!

Freelancing also allows you to work from home. How has that benefited you?

The ability to work remotely is a huge reason why I continue to freelance. I have an anxiety disorder, which can make working in an office tough for me sometimes. Being able to work from home definitely helps with this.

I also love that I don’t have to get dressed up for work. I know this sounds weird, but I have a strict “no pants” policy with my work – I don’t take on work that would require me to wear pants. I want to be judged for the work I’m doing, not what I’m wearing or what I look like. My thought has always been that if I have a job or client because of how I’m dressed or look, I’m not doing a good enough job.

Lastly, working from “home” gives me the ability to change my home and travel a lot. In the last year alone, I’ve worked from Tulum, Cabo, Scottsdale, Los Angeles, Turkey, Greece, Puerto Vallarta, Medellín, Bogotá, Cartagena, Chile, Denver, London, Turks & Caicos, Lisbon, New York, Hong Kong, and the Philippines. I’ve even started my own travel blog, Josh Trips, which is dedicated to helping remote workers find awesome and affordable locations to work from. It’s not always so glamorous, though – often when I’m traveling, I’m working so hard that I’m only able to leave my apartment or hotel for short stints each day. Even so, the freedom to work from wherever I want allows me to focus on work while indulging my passion for travel, and is one of my favorite things about freelancing.

About Josh Garber

Josh, a graduate of the University of Pennsylvania Law School,  has worked on nearly 200 projects through the UpCounsel marketplace and all 100 of his clients who have reviewed his work gave him 5 Stars. He regularly represents businesses in employment matters, business transactions and formations, contract drafting and management, and IP and corporate governance matters. Though he is dedicated to helping his clients avoid litigation, Josh has extensive trial experience and has obtained favorable outcomes in state and federal courts, mediations, arbitrations and DLSE hearings. Josh’s clients include Stripe, HotelTonight and Tesla.

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About the author

Ariel Shultz

Ariel Shultz

Ariel manages the attorney community at UpCounsel, where she focuses on helping attorneys find success and grow their practices. A former practicing lawyer herself, she understands the challenges facing attorneys and prioritizes making the UpCounsel attorney experience exceptional.

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