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From Lawyer to Entrepreneur
Pursuing Your Passion: From Lawyer to Entrepreneur

Pursuing Your Passion:
From Lawyer to Entrepreneur


I am living the dream of many practicing lawyers. I left Big Law, founded a successful company, and ten years later get to go to work every day with great people and clients, while doing work I really enjoy.

As an associate at a big firm, my colleagues and I fantasized daily about how great it would be to leave the grind behind. To blaze out into the business world, be our own bosses, bear our own risks, and beat the odds as entrepreneurs. Open a bar. Start a fast casual food franchise. Do a tech startup. Get into real estate. The possibilities were endless – bring it on! We even created a code name for our daydreaming: Operation Out-Law.

After six years of dreaming, I got to doing. I left and started a marketing and creative services agency that does brand strategy and website design and development. Out-Law, indeed.

But guess what? It’s no longer a daily habit, but hardly a week goes by that I don’t fantasize about how great it would be to be back at a big law firm. Don’t get me wrong – being an entrepreneur is great, and I’ll never actually go back to practicing law. But entrepreneurism is not what most young lawyers sitting in a conference room at 1 a.m. doing doc review while eating lo mein envision. It’s a grind, too. Just of a different variety.

I’m all for lawyers pursuing their passions and striking out on new paths – it’s one of the best decisions I’ve ever made and in many ways has wildly exceeded my expectations. But in many others it has thrown me for a loop, humbled me, and made me ask myself: What the hell was I thinking?

So is the desire to start your own business tugging at your sleeve? Here are a few things to consider:


What You’ll Give Up:

A Steady Paycheck
Get ready to budget! The days of twice monthly paychecks and annual W2 forms are over. Particularly in the early years, you’ll pay yourself when you can, what you can. You’ll pay closer attention to those Groupons in your inbox and coupons in your mailbox. While financial upside may be higher as an entrepreneur, financial stability is greater as a lawyer. It’s one of the big trade-offs. If you can stomach it, that’s what make entrepreneurism exciting and rewarding.

The Prestige of Being a Lawyer
We all know that the stereotypes that people have of lawyers are largely false. Popular culture glamorizes the profession and the people in it. But regardless of where impressions derive from, and lawyer jokes aside, the fact remains that lawyers are held in high regard relative to many other professions. Even though you may be having a blast in your new field, and achieving tremendous success, you’ll get puzzled looks and lots of questions about why you left the practice of law.

The Comfort of a Large Organization, Support Staff and Infrastructure
You’ve heard it before, and it’s true – you’ll wear many hats as a business owner. Until you get to the point where you have sufficient, steady cash flow to support a team of employees and vendors, you’ll have to make sure all the bookkeeping, supply ordering and check writing is covered. This can be difficult for those transitioning from law firms with large infrastructures in place that allow lawyers, by and large, to simply practice law.


What You’ll Need to Get Over:

Tendency Toward Risk Aversion
Lawyers are often risk averse, while entrepreneurs must embrace risk. Instead of throwing
up red flags when confronted with uncertainty, you’ll need to see uncertainty for what it is: opportunity.

Saying “Yes.”
Large law firms teach lawyers to do “whatever it takes” for clients – late nights, unreasonable demands, herculean efforts. Lawyers – particularly junior ones – often have no choice. “Yes” is the only option, as they are not empowered to say “no.” Business is different. “No” will be one of the most powerful, important words in your arsenal. No to a new client. No to a new project. No to a new commitment. Your time, attention and focus is everything. By saying “yes” too often, you’ll get yourself, and your business, into trouble.


What You’ll Gain:

An Appreciation for Others
Many lawyers assume that they can be successful in business because they are smart, capable, hardworking problem solvers. That’s true – they can be successful. But it doesn’t mean they will be. Success in business involves many factors, and can be a humbling experience. If you make the leap, you’ll better appreciate what it takes to build a company and those that have done it. By objectively assessing and learning from the successes of others, you’ll be in a position to emulate them.

A Desire for Discomfort
In a law firm environment, it’s not that hard to stay in your comfort zone. Don’t want to take that depo? Call a litigator. Not so when running your own business. You’ll be forced to face discomfort head on, all the time. With discomfort comes gains. You’ll learn that your limitations are not what you thought they were, and that you can accomplish more than you ever imagined.

A Zest for Life
Entrepreneurism is hard. And terrifying. And awesome. You’ll get to chart your own course, make your own decisions, and fail or succeed on your own terms. It’s not for everyone, but if you can’t resist that tug, give it a shot. You’ll feel empowered. You’ll feel alive.


James Harrington on EmailJames Harrington on Twitter
James Harrington
James Harrington
Jay Harrington is co-founder of Harrington Communications, where he leads the agency’s Brand Strategy, Content Creation and Client Service teams. He also writes weekly dispatches on the agency’s blog, Simply Stated. Previously, Jay was a commercial litigator and corporate bankruptcy attorney at Skadden, Arps, Slate, Meagher & Flom and Foley & Lardner. He has an undergraduate degree in journalism and earned his law degree from the University of Michigan Law School.


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