Why Most Lawyers Make Terrible Entrepreneurs

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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.

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40 responses

40 responses to “Why Most Lawyers Make Terrible Entrepreneurs”

  1. Oh so true… Working with a great high-tech accelerator in Eindhoven (hightechXL), The Netherlands and the challenges are compounded if the company is working with hardware as well as software. It is a continual fight between the Open Innovation guys and the lawyers who want to protect something even when no-one has yet defined it.

  2. Erica Duncan says:

    So this definitely caught my attention as I’m a lawyer who’s about to leave my day job to fully focus on the 2 businesses I’ve started.

    I must admit a few of my feathers were ruffled.

    But in the end, I think you’re right. It took me 4 years to pay attention to the nagging desire to start my own business. I often “shushed” it like a mother does to her child at church. I had a “good thing going”; a steady paycheck, savings, the prestige of being able to call myself a tax lawyer. The fact that I didn’t love what I was doing bothered me, but I kept telling myself that maybe i needed to be practicing law in a different way. So I switched law firms first (from a big NYC law firm to a smaller, more nurturing NYC law firm) and then switched cities to take on a tax structuring job at an accounting firm. I finally took the plunge and started 2 businesses last year. But I held onto my day job because I had a lot to work through. As you mentioned, I had to learn how to live with risk and uncertainty. My parents are both ‘treps so they really helped me. I had to get honest with myself and just work through it.

    I hope you do your workshop!!

  3. Sue Harrison says:

    Love the article. It’s a little frightening when you realize that about 95% of our elected federal legislators are lawyers. Maybe that’s why we always seem to enact such strange and strangling economic policies at the national level.

  4. Jodi Barnes says:

    Although I’m not a JD, I have a PhD in a field that requires a lot of compliance-thinking. You are definitely on the right track here. Many of us have been trained, early, to look for the problems, not the opportunities. I’m facing that within myself right now. I appreciate your post and would only add that you could extend the occupational list to include many in academe. Thanks!

  5. I think you DID indeed make the case for the course JF 🙂
    I am sending every former lawyer client of mine your way.
    And, why is it that one of the biggest “used to be a” field is the legal one?

  6. Ligia Buzan says:

    Training in the alchemy of fear is priceless, is finding the “gold” in the darkness of one’s “shadow” that Carl Jung talks about, is a new way of life. Live it or be forced to live it soon. What a perfect expression, Jonathan. Excellent post!

  7. I had this conversation years ago in a different context: musician friends claiming that art can’t be taught; you’re born with it, or you’re not. Nonsense.

    Carol Dweck smashed the fixed mindset as en excuse a long time ago.

    Risk tolerance can be learned. Art can be learned. All the right-brained stuff the modern world tries to scare and beat out of us can be learned.

    But it goes back to the old joke about how many psychologists it takes to change a light bulb: just one, but the light bulb has to *want* to change.

  8. Sharon says:

    I read your article with great interest and with the horrifying realization that almost all of Congress, both Senate and House, are lawyers….no wonder we are in trouble. Would they ever admit to #1? Probably not. Love your idea of teaching a course in law school! Thanks for great insights and suggestions.

  9. Danya says:

    I completely disagree. I think that the reasons cited for lawyers being bad entrepreneurs are the same reasons why ANYONE would fear opening a business. Most people like their steady paychecks and lack of ambiguity.

    I also disagree with the analysis that lawyers are taught to be risk averse and spend much time “being a failure cop to professor of possibility.” Firstly, you are probably specifically talking about litigators because transactional lawyers do not need to worry about these issues as much. More importantly though, as a litigator myself, it’s true that I find pitfalls, but I also find solutions. If the opposing counsel has an argument, I find an counter-argument. It may not be the best counter-argument given the set of facts before me, but I take that risk and try to win for my client. Attorneys actually can NOT be risk-averse if they want to advocate for their clients the best they can. They just need to anticipate what may come – which entrepreneurs need to as well.

    I think these observations are all largely built on stereotypes about lawyers. The concerns that are cited are similar to most peoples’ aversions to starting their own businesses (eg, risk aversion). Many lawyers I know have successful practices, which obviously requires great business skills.

  10. Great post! As a lawyer who fairly recently started a business, I totally agree and have had to address many of the issues you raised. Excellent piece! I am reading your book “uncertainty” and it is resonating with me in a big way. I appreciate your work and perspective very much and would enjoy connecting at some point.–David

  11. Kevin Rhodes says:

    Right on, Jonathan! In his article “Why Lawyers Are Unhappy,” Martin Seligman said that pessimism is a “well documented… major risk factor for unhappiness,” and that there is “a surprising correlation between pessimism and success in law school.” The attorney and law professor who wrote the book “The Destruction of Young Lawyers” said “Lawyers are pathologically unhappy.” Someone else (sorry, can’t put my finger on the source at the moment) called us “pathologically pessimistic.” Lawyers as a group are fascinating people – bright, articulate, caring, with wide interests and a drive to make an impact in one of society’s essential institutions. The problem comes when we apply all this risk-aversion and pessimism to entrepreneurship. Besides scuttling the endeavor, we’re wasting a lot of human potential to boot.

    Oh, one other thing… The authors of the book “The Happy Lawyer” conclude that the practice of law is “disproportionately filled” with people who tend to be less happy than the general populace, citing research that shows we’re more introverted and less socially connected, more doubt-ridden and inclined to consider worst case scenarios, more logical and less in touch with our feelings, as well as being achievement-oriented, aggressive, and competitive to a fault – all factors that weigh against personal happiness, not to mention entrepreneurial success.

  12. Sherri says:

    I’ve never been a lawyer, but I’ve worked with a few and I see exactly what you’re talking about.

    What struck me the most (being a big worrier) is that this also applies to those of us who become obsessed with worrying about “what’s the worst that could happen” and how we kind of fall within that lawyers group.

    I appreciated your insights and it gave me some big questions to ask myself as I’ve considered opening a business and being my own employer. Leaning into that abyss of fear has always been the big deterrent, but now I understand why…

  13. […] Here’s a great post from Jonathan Fields, a former lawyer turned entrepreneur and coach, on why most lawyers make lousy entrepreneurs.  http://www.jonathanfields.com/blog/why-most-lawyers-make-terrible-entrepreneurs/#comment-45469 […]

  14. I am one of those pathologically optimistic people you describe. I am an artist, work with creative visionaries and in doing so I have realized that I entirely inhabit this space of glass half full- especially as a mirror for my clients. A few years ago I went through one of the most difficult times in my life. I started a wholesale gift business with two friends. This , after several years fell apart with both sides in legal battles. I spent inordinate amount of time with lawyers trying to protect the diminishing asset of what I had worked so hard to create. I found this process of conserving, holding on ever so tightly incredibly exhausting. I think more than anything it had to do with having to occupy a foreign mindset- one of protection – fear and avoidance of what could occur. In the end I just basically had to walk away and lose a tremendous asset I had created. I found solace only once I began to focus on my art.

  15. Much as I hate to admit it, I know you’re right. I’m a lawyer with my own small practice and working to diversify my practice to include teaching online courses which are more scaleable. For me personally, I actually think I have too much tolerance for risk and uncertainty and I should be more cautious. As a result, I have probably focused too much on the entrepreneurial activities which have more long-term return, at the expense of short-term income.

    What I’ve tried to do is to craft the right balance between the cautious approach (i.e. billable hours bringing in income) and entrepreneurial work aimed towards my long-term goals.

    But for the most part, most lawyers I know would not make good entrepreneurs, even if they want to be entrepreneurs, for the reasons you outlined.

  16. Lisa Weikel says:

    This is an excellent article, Jonathan. You articulate well what I experienced personally over a stretch of many years.

    Indeed, even now, while I am exponentially happier being of service as a shamanic practitioner and writer, my under-girding of having been a general practice lawyer for 20 years actively (and 30 years technically, as I still maintain my license)influences most, if not all, of my professional decisions.

    Most of the time, my lawyer-self is the source of whispered worries and a pit-in-the-stomach creating litany of “Well, this, this, and this could happen if I…” I’ve mostly learned to pay attention, write them out, and decide how much weight they need to carry.

    I know we cannot protect against everything. And I know that lawsuits, by and large, are money and soul-sucking endeavors, albeit sometimes unavoidable or otherwise completely necessary.

    The bottom line, though, is that life is a risk. I am far too optimistic to feel comfortable always looking for every possible exposure. Part of being edgy is knowing that nothing’s guaranteed.

    That’s why the attorneys who love being attorneys are the ones I would seek out to be MY advocates or advisors when needed.

    I think you’re spot-on.

  17. Alexis Neely says:

    If you would love to create a training on this for lawyers, I’d love to host it to our community of lawyers who are pushing their edges and stepping into entrepreneurship, not by making the leap out of law, but by building their practices into businesses they can count on.

    I heard a great story from a friend who trains doctors recently and it really helped me to frame things. He said doctors are trained to 100% certainty. Not having it is a matter of life and death. So, it’s very difficult for them to move into entrepreneur think, which can requires you operate with at most 30% certainty at any given time. But once the doctors were made aware of this, they could switch hats.

    So, I’ve been talking about this to our lawyers because it’s really the same. Lawyers have also been trained to operate at 100% certainty. Anything else may not be a matter of life and death, but the consequences could still be severe, malpractice is always a big fear of lawyers, and frankly, what I’ve seen and from my own personal experience, the fear of looking dumb is a driving force for many lawyers. So operating on 30% certainty feels extremely foreign.

    But, when made aware of the need to switch hats and put on their 30% certainty hat and why it will help their businesses, I’ve seen that lawyers can absolutely do it and thrive.

    So, yes, more training of more lawyers is needed on this and I’m totally on board with you offering that up. Would love to support you in that.

  18. Ben says:

    Really helpful perspective.

    This definitely applies well to business schools as well. The Corporate environment emphasizes and rewards risk mitigation. There’s even a powerful department growing in most offices now called “risk management”.

    Growing up in this atmosphere definitely makes it difficult to be successful on the outside where you’re suddenly rewarded for taking risk.

    Great tips on getting started!

  19. Sean Low says:

    As a reformed lawyer myself, I totally appreciate this post and it completely resonates with me. In fact, I had to go through my own crash and burn with a very healthy dose of sheer will exploding in my face to fully grasp what you talk about. I would just love to add that mostly, for me anyway, lawyers cannot see failure as information, risk as valuable, uncertainty as opportunity. As much as it would be great for every lawyer to train their minds to be ready to be entrprenneurs, I think that it would be equally valuable for them to live in the idea that they will probably fail in their initial idea and to really embrace the idea that that failure is no reflection of their character. The rest you have said so well. Thanks so much for the post and gettting the conversation started.

  20. Jonathan Fields says:

    Great conversation, as always, gang!

    A few more thoughts –

    1 – Not arguing that every lawyer needs to become an entrepreneur or train in the mindset practices that would facilitate the ability to live with and at times even invite high levels of uncertainty. But those who do want to make the jump OR serve entrepreneurs as clients should. It’ll help their own journeys and help them understand how to better serve clients.

    2 – Also not arguing that lawyers who are serving entrepreneurs and startups should become more risk tolerant. Indeed, a focus on protecting against the downside is a necessary and valid role to play. Especially when working with the classic delusionally optimistic entrepreneur. It’s the interplay that creates the most effective outcomes.

    3 – While lawyers who start their own firms definitely wade into more indefinite waters than those who’d follow a prescribed path in a larger firm or organization, to me theirs is still fairly well-drawn path. I see very little innovation in the actual business model of legal practice (Alexis, I know you’re doing some very interesting things, but still very much the outlier). So I tend to look at private practice professional entrepreneurs differently than those who start ventures entirely outside of the profession, often with either nonexistent or much more fluidly proscribed paths.

    4 – I practiced as both a federal enforcement attorney (litigator) for the S.E.C. and a securities/private-equity deal lawyer for a mega-firm in NYC. And I’ve stayed close with many friends and colleagues who’ve practiced across a wide array of specialties. So my lens is drawn from both experiences.

    Litigators want to elicit testimony that will in some way benefit their clients, but even more important, they don’t want to get caught with their pants (or their client’s pants) down. Thus the old “never ask a question you don’t already know the answer to.” Deal lawyers structure first to memorialize the deal as conveyed by the business people, then to protect against downside risk, surprises and ambiguity and after that to further optimize. At least that was my experience, totally open to others having different experiences.

    Thanks as always for the wonderful, respectful and robust conversation. Love learning from you guys!

    • I have had two conversations with two attorneys in the past 24 hours where I referred them both to this post. Both attorneys were seeking to do something more entrepreneurial – not quite as entrepreneurial as starting a yoga studio, but still not exactly the traditional firm model.

      I would love to see more attorneys who pursue a 3rd way, where they don’t have to give up the clients they enjoy serving, and yet break the mold from simply practicing for a firm or operating their own firm. I wish more attorneys packaged their expertise into products or trainings that complemented or supplemented their legal services fee-based model. It’s kind of splitting the baby, but it would hopefully give lawyers – particularly small firm lawyers – more steady revenue and allow them to dip their toes into the waters of entrepreneurship without the larger risks of giving up the practice.

  21. Jen Brown says:

    I just celebrated my ‘2 year leaving law’ anniversary. I’m now own a triathlon coaching and personal training business.

    I can certainly see myself in your post. But thankfully I’ve been able to recognise when that (trained) “risk aversion” takes flight. I almost need to talk myself down off the ledge when it happens and realise that it’s my training kicking in, to look at it more objectively, assess the “real” risk (not just every single possible risk, major or minor), work through it and move forward.

  22. I think this really depends on the type of attorney. Litigation attorneys for example are very good at weighing risks and taking aggressive moves with no guarantee of payoff.

  23. This was a very interesting post and I completely agree how a certain training is hindering entrepreneurial success. I can very much relate from own experience trained in psychology and research. My question is and maybe Jonathan you can answer me or someone reading this. How do you train in the alchemy of fear? I do admit the problem and I examined my tolerance for ambiguity over the last years but I am still struggling dealing with fears in terms of leaning into the unknown and fully expressing my creativity.

  24. These mindset observations are valuable. I question though whether they are especially unique to lawyers. I’m guessing most people, lawyers or nonlawyers alike, are risk averse and have a tough time with uncertainty. It’s why most people in general are employees and not entrepreneurs.

    I am a corporate lawyer myself, now owner of my own firm (which I consider a variation of entrepreneurship). Though I stuck with the practice of lawyer, the transition still involved a huge adjustment. The key adjustment, in my view, is not so much moving from lawyer to non-lawyer but moving from W-2 employee (clear defined roles, steady paychecks) to on your own (chaos, messiness, hustling to put food on the table).

    In this regard, it may be the cushy sense of entitlement we tend to pick up in posh law schools and high paying firms that cause the real problems.

  25. Dave Topal says:

    My sister should see this – she is a lawyer but she never really did practice law because she was more of an entrepreneur. I personally agree that in order to really excel in business, you want to have that inner drive that tells you to go on even though you don’t have all your doves lined up.

  26. Great post Jonathan, that’s one of the fascinating things I find between the field of law and the field of mediation (or dispute resolution). Lawyers are trained not to ask questions that they don’t know the answer to and to minimize risk while mediators are trained to ask questions they don’t know the answer to in order to inspire creativity and outside-the-box thinking…though mediators don’t typically take those skills and externalize them towards their marketing/business development. Fascinating stuff!

  27. Geoffrey says:

    I showed this to my wife, and she laughed, because it rings so true. I am a recovering lawyer. Actually, I was a professor of law, and resigned from a tenured position many years ago.

    I represent both positions. On the one hand, I have taken enormous risks (such as resigning from a secure job for life), jumping into another field by accident, etc. And yet I still often focus on what could go wrong more than on what could go right.

    The core, to me, is still the notion of “following your bliss.” Do what calls. And then deal with the other issues from that place. It’s amazing how much security there is in being in the “right” place, for you, notwithstanding all that can/might/could go wrong.

    Great post.


    • Jonathan Fields says:

      Love this – “It’s amazing how much security there is in being in the “right” place, for you, notwithstanding all that can/might/could go wrong.”

  28. I definitely think you should create your syllabus for your course, Jonathan. Point #2 challenges lawyers to become their clients and think like their clients—very risky indeed.

    My husband and I filed a federal trademark infringement suit in Denver against a major corporation and won. The judge would have awarded greater damages if our lawyers had only listened to us. They set up a firewall between their strategy and us. Every time we tried to offer an idea for our case, we were told “not to play lawyer.”

    We have several stories you can use for examples if you need them for your course.

  29. Jonathan, this is the first time I’ve posted on your blog. I follow you and I’m taking your book marketing course to help launch my novel Secrets of the Field.

    I practiced law for over 25 years in a variety of capacities–As a congressional staff member; in-house for a Fortune 100 corporation; as a name partner in a small entrepreneurial boutique litigation firm; and for the bulk of my career, as an attorney-mediator. I did about 3,000 mediations over 17 years, and in each case I had contact with at least two lawyers and often as many as a dozen. We had a training school that trained about a thousand attorneys in the art of mediation, a consulting firm that advised clients about how to reduce their legal bills by proactive dispute resolution.

    In our mediation training school, we met lawyers (mostly litigators) who were simply burnt out on a molecular level after years of stress, chronic negativity, professional personas that involved being a ruthless jerk, and just too much work. Everyone was looking for a way out. Mediation offered the hope of a different career path, and ostensibly one that used the same skills that these folks had developed as litigators.

    Net result: About five (that’s right five) of those thousand actually were able to make the jump to an independent entrepreneurial life as a mediator, although many more did successfully start a mediation sub-business within their existing law practices.

    I have a lot of heart for lawyers, and our mediation school was motivated by a desire to transform the legal profession and improve the quality of life for lawyers and everyone they interacted with.

    Based on my experience and the contact with so many lawyers over the years, I am convinced that teaching entrepreneurship would be a great help to lawyers (like me and like you I think) who are or were essentially mis-matched for the profession and discovered early-on that they had made a mistake. These folks need to find a way– any way– to get the hell out of there and breathe some different air. Entrepreneurial training would be just the ticket.

    I am also convinced that folks that stay in the practice would not be best served by entrepreneurial training. They are poorly qualified for it for the reasons that you articulated, but the more important reason is that they simply don’t want to be business people. They want to be ‘experts’ — people who have gained a mastery over a skill set and a body of knowledge, and have claimed their expertise as their identity. They want to wake up in the same world every day, knowing what they know. This is simply an unacceptable state of affairs for the entrepreneurial mind which lives on novelty and learning.

    My instincts tell me that the lawyers would be best served by a training that teaches them how to start and continue a ‘personal evolution project’. Entrepreneurship is one way to evolve, but lawyers can also evolve by finding ways to become more significant in their communities; by starting a creative project some kind (there are a lot of hidden writers out there); by developing spiritually; and by creating a self-authoring life on terms that they consider acceptable.

    I’m up to my ears launching a book and brand at the moment, but am committed to going back to the lawyers with a personal evolution training. Would love to talk more with you about this when the time is right.

    • Jonathan Fields says:

      Ross – Great addition to the conversation! I’ll be noodling on all of your wonderful insights.

  30. Rosaline says:

    Thank you for writing this article, Jonathan! It feels so good to acknowledge that mindset training is necessary. It may sound weird but I agree that it’s not something people talk about. I had a wonderful undergraduate experience in terms of being inspired by amazing people and shortly thereafter I found steady employment in the areas of law (as a law clerk in Washington, DC) and now compliance for a financial services firm. I am thankful for the “job stability” I’ve experienced but increasingly growing in my awareness of wanting to live a different life. Part of my transition out of cubicle nation will be equanimity training with fear and uncertainty. Thank you again for posting this! I value it and I’ll share it with my network.

  31. Thanks for an interesting post and comments.

    I’m testing your claim right now with my own company, Mootus. I find that lawyers are far more diverse, interesting and adventurous than most people believe. My own take on the issue is that we shouldn’t assume the perspective lawyers are trained (and paid) to employ on behalf of their clients is some kind of innate characteristic or personality defect, no more so than we should assume that all doctors are hypochondriacs.

    Also, I think that lawyers are very well suited for entrepreneurial ventures touching upon the legal industry itself or on other regulated industries, where an understanding and appreciation for risk, complexity and the law is critical to success.

    And lastly, perhaps most obviously, lawyers in fact are entrepreneurs. Some have been wildly successful. In many respects, the huge numbers of lawyers practicing solo and in small firms in this country are no different than any other small business sector. Perhaps less so at big law firms, but even there, the reality is that many partners are building or managing their own small businesses within a larger organizational structure.

  32. Pooja says:

    All the qualities you’ve listed that make lawyers bad entrepreneurs are actually found in many others who have the same mindset, even without having being trained as lawyers. Most people on 9-5 jobs don’t have the propensity to take the risks that setting up a business requires. I loved the phrase “pathologically optimistic” because that somewhat describes me too. To build something up from scratch is a fascinating feeling!

  33. Hey Jonathan,

    GREAT Article! I’m so glad you addressed the issue. After watching your Good Life Video with Marie Forleo and hearing parts of your story I had to check you out and I am I glad! I decided to make the entrepreneurial leap while in law school and have had many conversations/inquiries about me pursuing my degree rather my purpose. Its hard for some of my family, friends, colleagues, and former professors to understand or accept that I made another choice. Further I had to learn how to balance my analytical “lawyer” brain with my creative “entrepreneur” brain to really be successful! Thanks for the info and you should definitely teach the class!

  34. […] That’s no surprise if you consider that lawyers get paid to be that way, as lawyer-turned-entrepreneur Jonathan Fields pointed out in a recent blog post entitled Why Lawyers Make Terrible Entrepreneurs: […]

  35. […] – Why Most Lawyers Make Terrible Entrepreneurs (Jonathan Fields) […]