Thrillable Hours: Joan Wharton, Founder Charlie Dog Boxer Company

Thrillable Hours - Careers for Lawyers Q&AWelcome back to Thrillable Hours,  my interview series about alternative careers for lawyers

I have never met Joan Wharton, but as with many of the lawyers in this Q&A series, she was delivered to me via the interwebs. In this case, she read Legal Nomads and reached out, sending over a thoughtful email about life after law. I enjoyed her story and — of course! — asked her to participate in Thrillable Hours.  At this point the series is self-sustaining, with great candidates forwarded my way by readers or, as with the case of Joan, contacting me themselves.

I hope you enjoy Joan’s Q&A,


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What made you decide to leave the practice of law?  Was there a particular moment that catalyzed the decision for you?

I decided to leave the law not because I didn’t like it anymore but because I’d known for several years that I wanted to try my hand at business at some point to challenge myself in new ways.  I’d practiced commercial litigation at Manhattan firms and in-house at a Connecticut company for about 12 years. But I reached the point that my desire to start a business couldn’t be ignored; I wanted to see what I could do beyond being a lawyer.  So while working by day as in-house counsel, I spent my nights and weekends over the next three years slowly developing Charlie Dog Boxer Company until it was finally ready to launch in November 2011.  At that point, I quit my “day job” to devote all my time and energy to growing my new business.  I haven’t looked back since.

Having spent almost 15 years drafting and reviewing countless legal briefs, I like to say that I’ve switched from briefs to boxers.

What do you find most fulfilling about your current job?  Why did you choose to found Charlie Dog Boxer Company?

By far the most fulfilling aspect of running my own company is the sense of control over my circumstances I have now that I didn’t when practicing law.  With my own business, I sink or swim based purely on my own initiative.  It’s a lot of work for sure, but I love the feeling that I control the company’s success and, by extension, my own destiny.  I’m convinced that if I work hard enough, try to make smart decisions, offer the best product and customer service possible, and stick with it through the difficult times, the company will succeed.  So far, happily, that’s been borne out.

On a more tangible level, equally fulfilling is being able to contribute to a cause I’ve always felt strongly about through the Charlie Dog 5% Pledge.  In developing my company, I knew from the start that I wanted it to be a business with a cause.  I’ve always been particularly moved by the plight of abused and neglected animals, so I designed the Charlie Dog 5% Pledge to donate 5% of the company’s net proceeds to local and national animal welfare organizations to support the important work they do.  Being able to share a part of whatever professional success I achieve with a cause I feel passionately about is definitely one of the most fulfilling parts of what I do.

I started Charlie Dog Boxer Company because I saw a gap in the men’s boxer market that needed to be filled.  While out shopping a few years ago, I wanted to pick up some comfortable boxers for my husband but kept coming across the same scratchy fabrics and uninspired patterns.  Frustrated by my lack of options, I left empty handed.  When I got home, my husband was wearing his favorite garment-washed button down shirt that had a great “broken in” feel to it and I thought the fabric would make perfect boxers.  I’d known for some time that I wanted to start a company and was just looking for the right opportunity, and I knew immediately that I’d stumbled upon it:  well-fitting premium men’s boxers with a comfortable, “lived in” feel that men would love.  I wanted to offer a good alternative for men – and women buying for them – who are looking for a bit of affordable luxury.

Charlie Dog Boxer Company
Charlie Dog Boxers

Do you have any advice for professionals who are interested in branching out from traditional private practice but are concerned about what is out there?

My advice would be to not limit yourself when considering how else you might want to use your talents.  I think professionals often feel trapped by their circumstances.  I can’t tell you how many lawyers I’ve talked to who say they wish they could do something completely different career-wise but the money they’re making affords them a comfortable lifestyle and they’re afraid to lose that security.  So they stay where they are, grinding away in a job they don’t necessarily find as fulfilling as they once did, rather than taking the leap to try something else that would challenge them in new and exciting ways.

To those people who are hesitant to branch out from private practice I’d say think hard about what you’re passionate about in life, what you love to do and are good at, and figure out how you can translate that into a full-time business.  To ease the inevitable financial burden you’ll face, do as much development work on the business as possible while you’re still employed and you have that financial security net available to you.  It’ll take you longer to develop the company because you’re limited to doing so in your spare time, but when the business is ready to launch, you can jettison your day job and devote 100% of your time to the new company knowing that you’ve put yourself in as good a financial situation as possible.  Sure there’s risk involved in branching out on your own, but what’s the alternative – staying in a career you no longer find fulfilling because doing something else will be difficult and uncertain?

One of my favorite quotes is, “Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do.”  That’s what I’d ask professionals who hesitate to branch out from private practice:  Will you look back 20 years from now and think, “I wish I’d taken a chance and tried doing ______?”  If so, do it now.

Charlie Dog Boxer Company
Charlie Dog Boxer Company’s gratuitous gentleman’s behind shot.

Do you still identify as a lawyer or use the skills you developed in your legal training?

I’m always surprised when someone asks me what I do and my first impulse is to answer with, “I’m a lawyer.”  I knew I wanted to be a lawyer from the time I was old enough to know what one was and I practiced for over 15 years before starting my company, so being a lawyer is definitely something I can’t help but strongly identify with.  It’s like muscle memory for me to say, “I’m a lawyer.”  But, luckily, after 18 months spent growing my company, it’s becoming more natural for me to say, “I own a small business.”

I use my legal training every day.  From filing the incorporation papers to negotiating contracts with vendors to researching statutes and regulations that govern my business, I constantly rely on my legal experience in running my company.  But I’ve been surprised by an unexpected benefit of my legal career:  In dealing with others in the fashion industry – retailers, vendors, other business owners – I find that my legal experience adds a bit of credibility to my business, as if people assume that if I could handle the rigors of law school and 15 years of private practice I must be industrious and organized enough to successfully run a company.  Not too many people who decide to start a men’s boxer company practiced law for 15 years beforehand, and that novelty is something others in the fashion industry often find interesting and want to talk about.  It’s a great conversation starter.

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What do you say to those who tell me lawyers can’t have fun?

I’d invite those people to join me on my next photo shoot in Manhattan.  What’s more fun than spending a day with a bunch of male models posing for photos in boxers I designed?  Experiences like that are not something I ever could have imagined having when I was working away in law school or at a large Manhattan firm, but they sure are fun!

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Joan Wharton

Joan Wharton graduated from Georgetown Law in 1997 and practiced commercial litigation for almost 15 years at large New York City law firms and in-house at a Connecticut marketing company before leaving law behind in November 2011 to launch Charlie Dog Boxer Company.  Joan currently lives in Weston, Connecticut, and runs her men’s premium boxer company from there.  You can find Charlie Dog Boxer Company online or follow along on Facebook and Twitter. Joan is also on Twitter @joanwharton.  

6 thoughts on “Thrillable Hours: Joan Wharton, Founder Charlie Dog Boxer Company”

  1. Inspiring story and a great idea. I was lamenting the lack of options in men’s briefs/boxers to my female friends within the last couple of weeks. Figures it’d take a woman to figure this out. Just in time for Christmas too girls:)

  2. I gotta admit, I clicked this post because my last name is Wharton and it caught my eye! But it’s a very insightful interview. I always love learning from people who have quit their jobs to pursue something that makes them more happy, especially if they could be my relative!

    Thanks for this.

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