5 Reasons to Be a Legal Entrepreneur Instead of an Associate


Here’s a truth for you: I have a vision of the world in which every person is an independent contractor with his or her company/ies…

Where we freely trade our gifts, time and expertise for compensation in a fluid, conscious, enjoyable way instead of being shackled to a desk for 8+ hours a day.

Let me tell you how I came to this…

The year I got out of law school, the legal industry was undergoing a major contraction. There were no jobs to be had in law firms. Even unpaid internships were at an all time low and the students at the top of the class were being told their offers were rescinded.

I knew I didn’t stand a chance in the competition for legal jobs (I was 40 at the time). That was the primary reason I decided to go out on my own right out of the gate.

But it turned out there were, are, many other reasons to be a legal entrepreneur than simply lack of employment opportunities! Here are some of my favorites:

1.  There’s no security in jobs anymore, anyway.

How many times have you met someone fully committed to their law firm for 15, 20, 25, 30 years who has been laid off?

We invest our lives and our souls into our work and often find our employers are not nearly so thoughtful of us. It is a tremendous sorrow when a breadwinner is laid off at 50-60 years old. Where are they going to go? How will they make a living?

Being a legal entrepreneur gives us more control over our own ability to earn a living in the long run. While by no means easy, at least we know who we’re working for and what the plan is.

2.  Lawyers need to be flexible, trainable, and responsive.

Law firms want us to laser focus our attention on whatever task needs completing. Law firms are less interested in expanding our skills than we would be if we allowed market forces to drive the development of those skills.

As entrepreneurs, we commit to keeping our skills fresh and expanding, to learning new things, to accessing more of our personal capacities. We get to bring our gifts more fully to life as entrepreneurs.

3.  There’s no other way to balance your life.

A law firm wants what it wants, period. You get 8 days of six leave, 10 days vacation, and benefits. In exchange, you have to have your butt in the seat provided, for the time they demand.

There is very little room in your life to maneuver in this setting.

I remember watching three of my sisters who were single moms move mountains to get into the office by 8:00 am; making lunches at 11:00 pm, doing laundry until midnight; getting kids to caretakers by 7:00 am, missing recitals and science fairs, and getting up everyday and doing it all over again. For years!

Legal entrepreneurs can schedule their time around their families intentionally and with specificity.

An added bonus, knowing how important this balance is themselves, entrepreneurs can also change the way they hire and operate so employees can have more of this personal sovereignty as well. Everyone wins!

4.  Our children need us.

I admit that even as a legal entrepreneur, I’ve had to work when I’d rather be with my kids. A lot.

But it pales in comparison to the 60-80 hour work weeks I’d have to spend at a law firm job, not counting the inefficiencies of commuting, paying for child care, having to do chores when I was home instead of spending time with family.

My mother used to say, “The days are long, but the years are short.” The time I have with my children is drawing to a close in the next four years. I want the flexibility of being able to choose the timeframe in which I do my work.

My children need me (and your children need you!) Not to hover, but to be in their “field” even if I am not attending to their daily needs anymore. As an entrepreneur, I can spend more time working in the house, where they’re moving about with their friends. I’m still working, but I’m also visible, present, and available.

5.  Our own happiness is critical to our future.

Far too many people are absolutely miserable in their work. Our children see us plod off to work each morning, head hanging. They see us sit in cubicle farms, the fabric walls plastered with pictures of our loved ones. They see our asses spread and our skin get paler and paler. They see the life in our eyes dim with each passing year.

Why would our children ever want to live like this? How depressing it is for a child to see their parent so unhappy. Why would they ever think that what they do matters in the world.


Because if our children do not see the joy, the life, the ecstatic “YES!” that is you, that is their possible future, they may well give up before they ever get started. They may not be able to claim their own happiness. And our culture will continue to spiral into decay, escapism, misalignment, inequality, apathy, and eventually soul death. What you want for your children is precisely how you should build your own life.

We all have things that must get done, deadlines to meet, appointments to keep but… How do you feel about your work right now?

Take a few moments to reflect on these questions to see what room for growth and expansion (aka CHANGE!) might be available or needed in your work life:

  • When I wake up, how do I feel about the work day ahead?
  • How do I feel when I get to my law firm?
  • What is the quality of my relationships at the firm?
  • How do my children see me in relationship to my work?
  • What might they be absorbing about my work life (also, consider asking them if they’re old enough)?
  • Do I enjoy my clients?
  • Can I get to know the people I work with on a deeper level than merely as their lawyer? Is that something I would want?
  • How does my body feel when I get home from work?
  • What is the quality and nature of my transition from work to home?
  • How does my partner perceive me in my work? In my transitions from work to home?
  • What kind of self-care do I need to feel calm, centered, and open in my work?
  • As an employee, am I truly happy with the nature of my relationship with my law firm? (Tell yourself the truth, even if you tell no one else.)
  • If I could have anything I wanted in my work life, what would I like to shift right now?

The decision to become a legal entrepreneur is a huge leap of faith… But so is being an employee, if you really think about it.

Being an employee means putting your faith in the partners of a law firm whose sole obligation is to its shareholders, not to you. Are you willing to continue to do that? Or are you ready to plunge into a life of self-determination where you can foster a wonderful life not just for yourself but for others who end up working for you?

The choice is yours. Even if it takes you some time to get to the point of being ready to take the leap into legal entrepreneurship, ultimately you might find it’s the best decision for you, long term. I definitely feel it’s one of the best decisions I’ve ever made and I’m so glad I had both the faith in myself to overcome the fears that naturally arise, and the support to move forward.

The answers are already within you. Trust yourself, and good luck!

DISCLAIMER: Because of the generality of this update, the information provided herein may not be applicable in all situations and should not be acted upon without specific legal advice based on particular situations.

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