I really enjoyed this one! Your career path reminds me of some advice I received in therapy when I was struggling to make an important career decision. Basically it was this: What is the worst that can happen if you choose wrong. Your choice is not forever and you can always pivot. That gave me the guts to take a leap and start my own business. A law degree provides so many opportunities and it can take some time to find where you best fit - and where you fit may change over time. Thank you very much for sharing this Jordan.
Love this post, Jordan. I can relate to so much of it personally and now am witnessing my own child try to imagine what their future will look like in terms of work. It’s become even more difficult for this generation I fear as the apparently limitless possibilities engender a kind of paralyzing fear.
“I believe there are no extraneous people and no purposeless lives in this world. I believe that everyone is here for a reason — several reasons actually, probably hundreds over the course of a lifetime.” If only law students could believe this, and feel this. Perhaps it’s spirituality in law that we are lacking.
Jordan, this is an excellent post on several levels, that moves me to thank you for it, and to share it with others. It is relatable and generalizable - one can fill in "lawyer" with almost any job or field of inquiry, if one feels there more by default than design. Many of us have at times over the arc of a career felt like a misfit toy or that extra Lego piece looking for the ideal fit in the project of a fulfilling life. Your authenticity, humility and strong human values that suffuse your articles and books are core to your power and influence.
Hi Jordan, thanks so much for sharing this. I used to manage legal technology in a law firm and was recently laid off (in the past month) due to restructuring. (Incidentally, I came across your blog because one of my bosses frequently shares your articles with the whole firm.) Hearing about the obstacles and uncertainty you faced in your own journey has brought me hope, especially because I'm a Christian who also believes that everything happens for a reason. Thanks especially for the reminder to stop worrying about what people expect you to be at a certain point in your career, and to think about what you're meant to be doing instead.
If I may, could I ask how you developed your ability to understand problems with the legal system and suggest solutions? For example, was it from having the opportunity to speak with many people in your career as a legal reporter/editor? I'm asking also because two jobs ago I worked in a role which involved researching trends affecting lawyers and publishing reports on these. However what I found hard about this was that I was mainly reading and synthesising reports written by others, so after a while it felt like I was just reporting what others were doing without adding value or better understanding the situation myself. (I wonder if the difference is that the role did not involve any firsthand interviews?)
Stella, thank you for your comments! But I'm very sorry to hear of your recent layoff, and I hope things turn around for you very quickly.
That's a really good question, and I'm not entirely sure what the answer might be. Exposure to so much industry data and anecdotal accounts from my publishing days was definitely helpful.
I had to learn as much as I could about the legal sector in order to report to lawyers on industry trends and developments, which was basically my job description. It also helped that to the extent I had any particular lawyerly talent (I don't think I have many), noticing patterns in what I was seeing and hearing -- and drawing reasonable conclusions about what was causing those patterns -- is probably the main one.
Speaking with lawyers directly was definitely helpful, but the problem with using lawyers as a source of insight is that most of them are poor observers and analysts of the legal market. They extrapolate almost entirely from their own experience and tend to downplay other perspectives, and they really don't have much of a knack for or interest in seeing the big picture. In my experience, lawyers are brilliant tacticians but pretty lousy strategists. So the key for me has been to listen to what lawyers say and try to piece together which of their observations are accurate and which are just self-involved noise. (There's a lot of the latter.)
In terms of how I came up with suggested solutions, I readily admit that most of them come by gut reaction. When I see so many unhappy lawyers and unhappy clients, I don't say, "Well, that's just how things are," I say, "Why on earth are things this bad?" If a particular law firm practice or lawyer attitude seems to me outdated or self-serving or callous, I say so. Which I guess means I trust my own instincts about what constitutes sensible and decent behaviours more than I trust the traditions of law practice, regardless of how rich those traditions have made many lawyers. And so I'll say, "Stop doing this thing that's irrational or reckless or unsupported by evidence, and start doing this other thing that seems more constructive and humane and has lots of good facts and reasoning to support it." There's not a lot more behind my analyses than that.
But I suppose the number-one means by which I've developed whatever skills I currently possess in this area was to write about it constantly, publish, and deal with feedback. There are more than 500 posts at my Law21 blog, well over half a million words, and I've gotten feedback on almost all of them, including objections, corrections, and (quite rarely) insults. Throw in another 50 Substack articles and another 75,000+ words in the last 16 months, and I've basically been putting all my theories out there to be tested for more than 15 years (not counting my 10 years as magazine editor). Lawyers are a fantastic audience if you want your ideas to be probed, attacked, and torn down -- and that's what I want. I can't get better or smarter unless other people challenge me to constantly refine my thinking, and lawyers are more than happy to do that.
So yeah, I guess I'd say that I got to where I am now because I was fortunate enough to have the opportunity not just to develop any number of ideas and conjectures about the legal market, but to get them in front of enough people (especially lawyers) to get a sense of where I was right and where I was wrong. I developed my own ideas about the legal sector because I had enough confidence in my own instincts (and my own professional moral compass) to believe those ideas had merit; I had enough humility to change course and rethink when the facts or arguments showed I was wrong; and enough courage (or stupidity :-)) to keep coming back and trying again.
So that's what I'd probably recommend. Blogging changed my career and my life as an outlet for spreading and testing my views on the law, and while blogging's day has passed, newsletters like Substack give everyone the opportunity to do the same today. Read and hear what's going on in the law, borrow what seems correct, form your own views of the situation, and then write them out for people to see. I'm a strong believer that "your people will find you if you put yourself out there to be found," and "people" in this case also includes "opportunity." I hope this has been helpful, and best wishes for your successful path forward!
Hi Jordan, thanks so much for taking the time to respond in such detail! It's both coincidental and encouraging that you credit writing with changing both your career and life. I've been wanting to write more for a long time, so the silver lining in getting laid off is finally having more time to do that. For me writing is a way to help more lawyers to work more efficiently. If I conduct a training at work (for example), I'm helping only my colleagues, but if I turn that same training into an article it helps significantly more people. I previously published a series on Microsoft Word for lawyers (in the Singapore Law Gazette, an online magazine for lawyers) that was well-received, and am preparing another series for the same platform on how to review boilerplate clauses.
Could I also ask what advice you might have on choosing topics to write about? I recall reading in another of your posts that you write only when you have something to say (as you don't agree with conventional advice to publish regularly only to keep people's attention). As someone who is still relatively new to this area, my current approach is to write where I can see there is a widespread and important problem which I have the expertise to address (e.g. lawyers spend hours formatting Word docs, or lawyers skim over reviewing the boilerplate clauses when pressed for time). Was wondering what (if any) advice you might add? And thanks so much for your time!
Well said, Jordan! There are many excellent lawyers whose work advances the interests of their clients. That’s noble… but it would have been too small for you. You have a unique ability to see and describe the big picture. Your analysis and recommendations consider multiple perspectives, an approach sorely lacking in self-regulators whose primary objective is to protect the guild. And you’re fearless in advocating change to smart people who aren’t accustomed to questioning the economic and moral foundation of their chosen profession. That Biglaw partner didn’t just do you a favor. He did us all a favor.
Jordan, I love this. I'll share it with my students. I had a very happy career in BigLaw for 30 years. But then I realized BigLaw was no longer for me, and I took a risk and made a change. That was 17 years ago. I found my purpose in life later in my career. It's never too late to change.
I haven’t run into the partner since then — I expect he’s retired by now — but I bore him no ill will. It’s no fun being the partner who has to break the bad news to the articling student. And I stayed on good terms with the firm — I even provided their associates and staff with some future-of-law presentations several years back! Honestly, they did me a favour — I wouldn’t be where I am today had I stayed on and struggled as an unhappy associate for a few years. Sometimes you have to trust that the river knows where it’s taking you.
I really enjoyed this one! Your career path reminds me of some advice I received in therapy when I was struggling to make an important career decision. Basically it was this: What is the worst that can happen if you choose wrong. Your choice is not forever and you can always pivot. That gave me the guts to take a leap and start my own business. A law degree provides so many opportunities and it can take some time to find where you best fit - and where you fit may change over time. Thank you very much for sharing this Jordan.
Love this post, Jordan. I can relate to so much of it personally and now am witnessing my own child try to imagine what their future will look like in terms of work. It’s become even more difficult for this generation I fear as the apparently limitless possibilities engender a kind of paralyzing fear.
“I believe there are no extraneous people and no purposeless lives in this world. I believe that everyone is here for a reason — several reasons actually, probably hundreds over the course of a lifetime.” If only law students could believe this, and feel this. Perhaps it’s spirituality in law that we are lacking.
I appreciate you and your writing 🙏
Jordan, this is an excellent post on several levels, that moves me to thank you for it, and to share it with others. It is relatable and generalizable - one can fill in "lawyer" with almost any job or field of inquiry, if one feels there more by default than design. Many of us have at times over the arc of a career felt like a misfit toy or that extra Lego piece looking for the ideal fit in the project of a fulfilling life. Your authenticity, humility and strong human values that suffuse your articles and books are core to your power and influence.
Hi Jordan, thanks so much for sharing this. I used to manage legal technology in a law firm and was recently laid off (in the past month) due to restructuring. (Incidentally, I came across your blog because one of my bosses frequently shares your articles with the whole firm.) Hearing about the obstacles and uncertainty you faced in your own journey has brought me hope, especially because I'm a Christian who also believes that everything happens for a reason. Thanks especially for the reminder to stop worrying about what people expect you to be at a certain point in your career, and to think about what you're meant to be doing instead.
If I may, could I ask how you developed your ability to understand problems with the legal system and suggest solutions? For example, was it from having the opportunity to speak with many people in your career as a legal reporter/editor? I'm asking also because two jobs ago I worked in a role which involved researching trends affecting lawyers and publishing reports on these. However what I found hard about this was that I was mainly reading and synthesising reports written by others, so after a while it felt like I was just reporting what others were doing without adding value or better understanding the situation myself. (I wonder if the difference is that the role did not involve any firsthand interviews?)
Stella, thank you for your comments! But I'm very sorry to hear of your recent layoff, and I hope things turn around for you very quickly.
That's a really good question, and I'm not entirely sure what the answer might be. Exposure to so much industry data and anecdotal accounts from my publishing days was definitely helpful.
I had to learn as much as I could about the legal sector in order to report to lawyers on industry trends and developments, which was basically my job description. It also helped that to the extent I had any particular lawyerly talent (I don't think I have many), noticing patterns in what I was seeing and hearing -- and drawing reasonable conclusions about what was causing those patterns -- is probably the main one.
Speaking with lawyers directly was definitely helpful, but the problem with using lawyers as a source of insight is that most of them are poor observers and analysts of the legal market. They extrapolate almost entirely from their own experience and tend to downplay other perspectives, and they really don't have much of a knack for or interest in seeing the big picture. In my experience, lawyers are brilliant tacticians but pretty lousy strategists. So the key for me has been to listen to what lawyers say and try to piece together which of their observations are accurate and which are just self-involved noise. (There's a lot of the latter.)
In terms of how I came up with suggested solutions, I readily admit that most of them come by gut reaction. When I see so many unhappy lawyers and unhappy clients, I don't say, "Well, that's just how things are," I say, "Why on earth are things this bad?" If a particular law firm practice or lawyer attitude seems to me outdated or self-serving or callous, I say so. Which I guess means I trust my own instincts about what constitutes sensible and decent behaviours more than I trust the traditions of law practice, regardless of how rich those traditions have made many lawyers. And so I'll say, "Stop doing this thing that's irrational or reckless or unsupported by evidence, and start doing this other thing that seems more constructive and humane and has lots of good facts and reasoning to support it." There's not a lot more behind my analyses than that.
But I suppose the number-one means by which I've developed whatever skills I currently possess in this area was to write about it constantly, publish, and deal with feedback. There are more than 500 posts at my Law21 blog, well over half a million words, and I've gotten feedback on almost all of them, including objections, corrections, and (quite rarely) insults. Throw in another 50 Substack articles and another 75,000+ words in the last 16 months, and I've basically been putting all my theories out there to be tested for more than 15 years (not counting my 10 years as magazine editor). Lawyers are a fantastic audience if you want your ideas to be probed, attacked, and torn down -- and that's what I want. I can't get better or smarter unless other people challenge me to constantly refine my thinking, and lawyers are more than happy to do that.
So yeah, I guess I'd say that I got to where I am now because I was fortunate enough to have the opportunity not just to develop any number of ideas and conjectures about the legal market, but to get them in front of enough people (especially lawyers) to get a sense of where I was right and where I was wrong. I developed my own ideas about the legal sector because I had enough confidence in my own instincts (and my own professional moral compass) to believe those ideas had merit; I had enough humility to change course and rethink when the facts or arguments showed I was wrong; and enough courage (or stupidity :-)) to keep coming back and trying again.
So that's what I'd probably recommend. Blogging changed my career and my life as an outlet for spreading and testing my views on the law, and while blogging's day has passed, newsletters like Substack give everyone the opportunity to do the same today. Read and hear what's going on in the law, borrow what seems correct, form your own views of the situation, and then write them out for people to see. I'm a strong believer that "your people will find you if you put yourself out there to be found," and "people" in this case also includes "opportunity." I hope this has been helpful, and best wishes for your successful path forward!
Hi Jordan, thanks so much for taking the time to respond in such detail! It's both coincidental and encouraging that you credit writing with changing both your career and life. I've been wanting to write more for a long time, so the silver lining in getting laid off is finally having more time to do that. For me writing is a way to help more lawyers to work more efficiently. If I conduct a training at work (for example), I'm helping only my colleagues, but if I turn that same training into an article it helps significantly more people. I previously published a series on Microsoft Word for lawyers (in the Singapore Law Gazette, an online magazine for lawyers) that was well-received, and am preparing another series for the same platform on how to review boilerplate clauses.
Could I also ask what advice you might have on choosing topics to write about? I recall reading in another of your posts that you write only when you have something to say (as you don't agree with conventional advice to publish regularly only to keep people's attention). As someone who is still relatively new to this area, my current approach is to write where I can see there is a widespread and important problem which I have the expertise to address (e.g. lawyers spend hours formatting Word docs, or lawyers skim over reviewing the boilerplate clauses when pressed for time). Was wondering what (if any) advice you might add? And thanks so much for your time!
Great article, Jordan, and inspiring, thank you for sharing it. - Hugh
Well said, Jordan! There are many excellent lawyers whose work advances the interests of their clients. That’s noble… but it would have been too small for you. You have a unique ability to see and describe the big picture. Your analysis and recommendations consider multiple perspectives, an approach sorely lacking in self-regulators whose primary objective is to protect the guild. And you’re fearless in advocating change to smart people who aren’t accustomed to questioning the economic and moral foundation of their chosen profession. That Biglaw partner didn’t just do you a favor. He did us all a favor.
Tim, that might just be the nicest thing anyone has ever said to me. 🙂 My genuine and sincere thanks — I deeply appreciate it!
Jordan, I love this. I'll share it with my students. I had a very happy career in BigLaw for 30 years. But then I realized BigLaw was no longer for me, and I took a risk and made a change. That was 17 years ago. I found my purpose in life later in my career. It's never too late to change.
As someone who just passed the bar and has no idea where she's going and is now tearing up reading this serendipitous post: thank you.
Amen, amen, and amen.
Love this post Jordan. Thank you for sharing your story in this way.
Great advice, Jordan! In my case, it took me 23 years until I finally discovered - almost by accident! - what I wanted to do.
Did you ever run into that person or people from the BigLaw Firm that didn't keep you on after articling? And if so, did they recognize you?
I appreciate your writing at this time in my life when I am in the biggest battle to seek justice for my abused, coerced, exploited mother.
Hope, Faith, Love Eternal
I haven’t run into the partner since then — I expect he’s retired by now — but I bore him no ill will. It’s no fun being the partner who has to break the bad news to the articling student. And I stayed on good terms with the firm — I even provided their associates and staff with some future-of-law presentations several years back! Honestly, they did me a favour — I wouldn’t be where I am today had I stayed on and struggled as an unhappy associate for a few years. Sometimes you have to trust that the river knows where it’s taking you.