11 Reality Checks for Lawyers Seeking a New Career Path

is guest post was written by Clay Westbrook. You can read Clay’s bio at the end of the post.

11When you spend enough time around lawyers, you learn that lawyers love to complain. Maybe that’s why a lawsuit is called a Complaint.

What complaint do we hear most often among unhappy lawyers who want a career change? Compensation is almost never the biggest issue. Or even working long hours.

Nope, most of these attorneys’ biggest problem with their career situation is:

I have no chance to reach my full potential here.”

There’s a reason you’re not reaching your full potential there.

To solve this problem, you’ll have to make big changes.  You have to:


The firm isn’t going to change.

[Note: Realizing the lack of potential is actually a HUGE step in the right direction. You're in a small group of people who are ahead of the game.]

Knowing that change isn’t coming from outside, what should you do?

Start by learning these 11 rules (okay, actually 10 rules and one unnecessary lie) “they” never taught you.

You’ll get an amazing jump start on finding the best place for you, in or out of law.

A few will give you an unfair advantage, some will take some effort, and many will make no sense whatsoever to you (but deny them at your peril). So let’s go.

1. The best way to start your career makeover is to do a better job where you are now.

Do a better job at a place I intend to leave?

Yes. For two reasons: 

First, your goal should not be to find another job or career. Your goal should be to not need your current job or career.

[See the difference? The former is passive and largely out of your control. The latter is active with you in total control.]

Second, you’ll find the more you don’t need your current job, the more valuable you are to your employer.

You can apply the points in this article to your current situation TODAY and begin working toward what you really need: autonomy.

2. Finding the “Perfect Career for You” isn’t really necessary.

Don’t spend your time figuring out your unique strengths, or your Dream Career, what you are best at, or what you enjoy that people will pay you to do. 

The usual game plan is to figure out what you really want to do, then start planning. Waiting until you find a “perfect” career is  a fantastic excuse for you to procrastinate.

We have two problems with the usual career counseling approach:

First, with career counseling you get to do the fun part first (introspection and personality tests and daydreaming/brainstorming about the perfect career) and the hard part last (the grinding, discouraging job hunt).

Second, the process is entirely too passive. Reading, researching, sending out letters, fine tuning a resume’, etc. are important. And you need to spend as little time as possible doing it.

If you know your ideal career, great. If not, don’t spend time looking right now. You have more important things to do.

That doesn’t mean you don’t search. But searching a simpler way will save huge amounts of time and energy. Search by keeping your eyes and ears open (more on this later).

3. Anyone can run their own business when they realize they already do.

You’ve been self-employed since the day you walked off the podium at law school graduation. Everyone (especially in the current economy) realizes this eventually.

Right now you have one client, your law firm, who keeps you on a yearly retainer (your salary and benefits).

Treat your career as if you are the CEO of [Your Name Here], Inc. Start by learning the differences between running a business and practicing law.

4. The more money you have, the more options you have.

“Everybody knows that, man. I thought this was stuff I never learned?!”


Wasting money is worse than not earning it in the first place (because you still have to pay the taxes). Every business owner (that’s you now, remember) at some point learns How to Never Spend Any Money on Anything. Ever.

You don’t need to go to that extreme, but do this:

  • Download your bank statements & credit card bills
  • Categorize your expenses
  • Figure out how much money you spend on stuff you don’t need (hint: probably 30-40%)
  • Figure out your absolute minimum level of expenses per month
  • Stick at least 6 times that number in the bank

How would your attitude about your career change if you could go 6 months without a paycheck?

5. Attorney productivity is the exact opposite of productivity in the real world.

In the real world, the goal is always to accomplish as much as possible in the least amount of time.
This is, ahem, not necessarily the case in the legal profession.

And in the Real World you don’t need everything to be just exactly perfect. Learn this before it kills you.

Even if you aren’t contemplating a career transition but want to start your own law firm, you must work as efficiently as you work effectively.

Apps, websites, books, etc. are everywhere, and you can’t really go wrong so long as you pick a method and stick to it. Pick the tools that are right for you.

The Mac App Store, Google Chrome, or Download.com are great places to start. Take the reviews seriously; some people are quite fanatical about apps and how useful they are.

6. The key to success is not what you know or who you know. It’s knowing who you know.

A great contact is worthless if you forget about them, or don’t remember the name or how to get in touch. Who you know and why drives everything. This affects where you are going to have to start in order to achieve your goals.

Your contacts file sucks. Organize it and understand it. Prioritize and classify (categorize) your contacts. Get on LinkedIn and connect with anyone and everyone you know. Import your LinkedIn connections’ contact info into your contacts file and vice-versa. Organize in the way that works best for you.

Categories in Outlook and Groups in iCloud are easy to learn and use as a starting point.

7. You have to unlearn everything you think you know about marketing and business development. Especially that you aren’t good at it.

If you have doubts, silence them: everyone can be good at marketing and business development. You can “eat what you kill.”  Don’t take advice from law firm marketing ‘experts.’ Market to customers with whom you feel comfortable and confident, and adopt the selling style that is most comfortable for you. If you are reserved, realize that there are millions of shy, quiet people out there who need lawyers or will buy stuff you are selling.

You may have noticed that clients tend to reflect the personality of their attorneys, and vice versa. If the lawyer is an arrogant jerk, his clients are likely arrogant jerks, too. This is not a coincidence.

How do you get started marketing yourself? Talk about skills and value instead of experience and knowledge. [this article explains how]  Describe yourself in terms of how you (a) made people money, (b) saved people money, (c) prevented problems, and/or (d) solved problems.

This is how you add value. Think in these terms, not knowledge and experience.

8. The best way to find your perfect job or ideal career is to do things you don’t ordinarily do.

We mean this literally. Go someplace new, take some lessons, ask for directions, read fiction, overcome a fear, strike up a conversation. Nothing’s going to change if your routine never changes. New things stimulate creativity and opportunity.

Does this describe how you live your life?

We also mean this from a practical standpoint. For lawyers, doing what you don’t ordinarily do means:

  • quantifying and building your network
  • understanding how non-lawyers make decisions
  • identifying and understanding your weaknesses
  • mastering personal & business finance
  • communicating less like a lawyer
  • maximizing your productivity, not your time, at work
  • understanding effective marketing and sales

9. Lawyers don’t understand the business world, but the good news is that most people in the business world don’t either.

The truth is that most businesses are terribly run. Talented people are good at doing what they’re good at doing. But nobody is good at everything. Everyone’s day involves mostly doing other things in which they do not have expertise. Most mistakes are due to lack of knowledge, and without knowledge, someone might not even realize they’ve made a mistake. [here’s a good video on this topic]

This is your opportunity. One of the best ways to make yourself valuable is to know more about something than anyone else. But take it a step further and develop some strong opinions about your chosen field of expertise (in or out of the legal profession)—this is where you separate yourself from the pack and become a leader.

So work on being valuable and autonomous, and bring some variety into your life. Because if you’re unhappy and want real change…

10. Going to another law firm is just kicking the can down the road.

Let’s face it: all law firms are pretty much the same. With a few marginal differences they have the same basic structure, management, compensation formulas, operations, sociopaths, etc.

If you’re frustrated with your compensation, or need more support staff, or see the firm as dysfunctional, or wish the firm would do more to help your practice, or don’t see room for you at the top, or don’t find some colleagues particularly trustworthy (and/or competent), a new firm will be a temporary fix unless you’re extremely lucky.

There’s nothing wrong with holding down a steady job and doing good work and getting paid well. But if you want to challenge yourself to reach your full potential, control your own destiny, you’ll need more.

We’ll see about that.

11. When writing articles that are in the form of a list, always list 11 items.


Yes. Always.


You can achieve autonomy that very few people (and even fewer lawyers) will ever attain if you learn and live by these lessons. Then you can decide on a new career and go get it.

Along the way, if you continue learning and improving (and doing things you don’t ordinarily do), the confidence you gain in yourself will show you the way to the place you need to be. The outcome may even be staying where you are now or finding a new law firm or going in-house.

When you get to a position where you know you can start your law firm, or quit practicing law to start a business, or take the time to find a better place for you, you’ll have the leverage to go in any direction your heart wants to take you.

Westbrook9226_LinkedIN Clay Westbrook spent 15 years practicing law – commercial real estate transactions, corporate M&A transactions and corporate law – in addition to working in-house with one of the nation’s largest title insurance companies. When not advising fellow attorneys on career transitions, Clay works in corporate finance and financial restructuring and was actively involved in settling over $500 Million in problem loans for clients across the country. Clay is at his best when managing the clients’ expectations and emotions in crisis situations and keeping them on track though an uncertain, extremely stressful process. This skillset and interest in helping others led him to found Juris Direction as a specialized alternative to typical career counseling. He graduated with honors from the University of Georgia School of Law and lives in Atlanta with his wife and sons.

Connect with Clay on his website, LinkedIn, Facebook, and Twitter.

All opinions, advice, and experiences of guest bloggers/columnists are those of the author and do not necessarily reflect the opinions, practices or experiences of Solo Practice University®.

This entry was posted in Guest Bloggers, Subjective Opinions, Work/Life and tagged Clay Westbrook. Bookmark the permalink.

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