jonathan-law-yogaOver the years, a number of people have suggested that I run workshops for lawyers who want to be (or think they want to be) entrepreneurs.

On paper, they’d say, I’m the perfect person for the job. I made the jump, founded, built and sold a number of ventures online and offline. I teach, write and speak.

And for just as long I’ve said no. Here’s why…

While thousands of lawyers make the leap every year, it’s been my observation that very few succeed.

Not because they’re not smart, hard-working, insanely capable problem-solvers and good people with great intentions. But because the way you are taught to think, see the world and operate as a lawyer shuts down nearly every entrepreneurial instinct.

As a lawyer, a big part of your job is to forecast every conceivable thing that can go wrong for your client, then protect against it. To remove ambiguity and uncertainty. With whatever time you’ve got left, you focus on putting the legal structure in place to maximize the upside.

But that’s nearly always second to protecting against the downside. In part, because it’s often more easily quantified. In part, because that’s what clients hire you to do. And, also because if you miss a major risk and things go south, you’re going to share in the blame for the hit.

This “fire-walling failure” mindset is a key to your job as a lawyer. But it’s total disaster for the role of entrepreneur.

Entrepreneurs need to understand risk. They need to understand need, desire and possibility. But they also need to be, as Jerry Colonna put it, pathologically optimistic. They need to believe the impossible can be done on an almost irrational level. To them, uncomfortable as it often is, uncertainty, ambiguity, the unknown serve as rides in a necessary playground of possibility.

Entrepreneurs need to focus on building something from nothing, not protecting against losing everything.

They hire lawyers to do that.

So, when lawyers bring a prevent-offense mentality into the world of entrepreneurship, disaster often ensues. Because everything they’ve been taught and everything they’ve practiced has indoctrinated an approach to risk, action, uncertainty and possibility that wars violently with the mindset needed to succeed in the world of necessary blank canvases and undefinable outcomes.

Question is…

If you’re a lawyer with a desire to enter the world of entrepreneurship, what do you do about it?

No easy answer here, but there are some important things to think about, beyond all the standard “should you really be working for yourself” checklists:

1. Admit you have a problem.

It’s not a personal judgment. It’s simply the way you’ve been trained plus, for some, an innate bias toward negativity and away from risk and ambiguity tolerance. You’ve spent thousands of billable hours finding fail points, imaging ones that don’t and likely never will exist and protecting against them. That’s your job, but in order to succeed as an entrepreneur, you’ve got to shift from being a failure cop to professor of possibility.

2. Examine your tolerance for risk and ambiguity.

Ask yourself if you’re really capable of living in a place of mass ambiguity, unprotectable exposure to risk of loss, judgment and uncertainty for extended periods of time, potentially years. If you are, great (though I can pretty much guarantee your first internal “hell yes” will have been more bravado than brains, so give yourself time to consider the question).

If you aren’t…

3. Train in the alchemy of fear.

Learn and cultivate the daily practices and shifts in outlook needed to help you lean into that place with far greater equanimity.

Some will tell you, by the way, this is not possible, you are who you are. I don’t believe that. A certain amount of mindset likely defaults to a genetically determined setpoint. But, a huge chunk is also trainable. While a thin slice of entrepreneurs are natural born fear alchemists and entrepreneurs, most are not. Instead, they’re people possessed with the drive to create who train in the ability to lean into the abyss, even though they may not realize that’s what they’re doing.

In the end, here’s what I’ve come to believe. The few lawyers who make the leap and hit the ground running were really entrepreneurs in lawyers’ clothing. A far smaller selection realize they’ve got a problem and do the work needed to shift their approach and, indeed, the very way they see the world.

The vast majority, though, never do the work. In part because they don’t know there’s a problem. And, then, because they don’t know how to fix it. So, they end up crashing and burning or grinding out the illusion of success through sheer force of will, but it ain’t fun. It’s brutally hard, and most end up wishing they’d never left the law.

I’m sure that, in writing this, I’ve rustled some feathers…

That’s not my intent. I’ve had this conversation privately hundreds of times, both with lawyers and those who’ve worked with and under them in ventures when they take on business roles.

My goal here is twofold:

  • To bring this conversation out into the open and have a real dialogue about a phenomenon that nobody seems to be talking about.
  • To identify key questions and and points of inflection for those lawyers who feel pulled toward entrepreneurship beyond the desire to build their own law practice.

I’d also love to see the deeper, real-world psychology and mindset side of entrepreneurship taught in law school (and B-school, for that matter). Right now, it’s a gaping void in the curriculum of both.

This would better inform the many lawyers who feel pulled to leave the practice to enter the world of entrepreneurship. It would also help lawyers better understand the psychology of their entrepreneurial clients, serve them on a more connected level and create better aligned relationships and solutions.

Now, before anyone starts listing out the lawyers who’ve become great entrepreneurs, I get it. It’s not impossible. I’ve said as much above. In fact, I know a number myself. My point is, those are the outliers. The people who’ve been able to make the shift not just operationally, but psychologically.

So, what do you think?

Are you a lawyer who yearns to launch or who has left the practice to build your own non-legal venture? If so, how have you dealt with this? Are you even aware of it?

Have you worked with lawyer-turned-entrepreneurs? How’s it been?

Are you in law school, thinking about doing your own thing?

Share your thoughts in the comments below…

With gratitude,


P.S. – If you’re the dean of a law school…call me. You’re missing a class.

P.P.S. – I think I might’ve just talked myself into creating a training for lawyers! lol.

Jonathan Fields is a serial-entrepreneur, business strategist, speaker and author. His latest book is Uncertainty: Turning Fear and Doubt Into Fuel For Brilliance. Fields writes about performance-mindset, innovation, leading and entrepreneurship at

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