Financing Your Post-Law Transition

moneyscrabbleOne of the hardest issues many unhappy lawyers face is how to finance their transitions.   As one reader pointed out, while it has been done, it is harder to contemplate leaving the law if you don’t have resources like a financially supportive spouse and/or significant savings to cushion the gap between jobs.

Paying back student loans can complicate the process further.  If loans are an issue, my first suggestions are (1) talk to a qualified credit counselor and (2) find out what kind of restructuring may be available if you lose or leave your job.  Some federal loans have income-based repayment plans, for example.

In addition, the following suggestions are based on my research (now in its sixth year!):

1)  Identify what you need to live on, at a minimum.  Unless you’re sure you can leap from one six figure salary to another (which has been done), think about ways to reduce your expenses before you need to.   Leaving some law jobs can correlate to reduced expenses (in wardrobe, in commuting, in recreational shopping designed to offset the dreariness and boredom of an unfulfilling career), and that can help as well.  Some expenses, like child care and health care, may be non-negotiable.  You’ll need to know what your financial minimum is before you negotiate your next salary.

2) Get your family on board.  I can’t tell you how often I speak with people whose significant others are nervous about career transitions because of a fear that they won’t be provided for as well.  Sometimes that’s shorthand for a general fear of change and/or a fear of failure; sometimes it’s recognition of the burdens of mortgages, private school tuition, etc.   Family anxiety can also cause the kind of personal stress that makes any career move hard to bear – after all, there’s only so much instability one person can take on at a time.  On the other hand, if your S.O. understands not only why but how you’re making the transition, and can appreciate how much better a partner you will be when you’re happier, the process will be much more bearable.  If you can describe a sensible and articulable strategy, like the one I recommend in Life After Law, your S.O. may be more supportive.

3) Take unemployment compensation if you can.  You’ve probably been paying into it for a while, and there is no shame in receiving it.  While there is usually an upper limit on the payouts, and restrictions certainly apply, unemployment payments can make an enormous difference in your ability to withstand time between jobs.   If you haven’t left your firm yet and are on the brink, it may be worthwhile to explore options for leaving.   Some firms will reach an understanding with unhappy lawyers, allowing them to collect unemployment insurance as part of a mutually beneficial parting of ways.

Beyond these suggestions, let’s face it: money is emotional.  The psychology of money plays out in leaving law in too many ways to discuss here fully, but I’ll just toss one more out.  When I left my law firm job, I was no longer the family breadwinner.  It took me well over a year to accept the idea of letting my husband pay for family groceries.  It was the first time in my adult life that I had been dependent on anyone and I hated it.  That period of dependence, however, helped me get through the financially-suffering period that ended when I accepted my current full time job.  I really like paying for groceries now.

Readers, would you please share your thoughts on how to finance a career transition below?

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3 Ways to Leverage College for a Career You Love

Dell Women's Entrepreneur Network event - NYC

Next week, I’ll teach my first classes of the semester, and some of my first-year students will start worrying about their job prospects.  Although I want to help all my students find work they love, I have better advice for the women.  There are many things that college women can do to prepare for a genuinely rewarding career aside from getting stellar grades.  But if I had to choose three areas of significant focus, I would zero in on these, because I think they can make a tremendous and fairly immediate difference after you graduate.

The importance of making professional (not just social) connections.

Success comes from doing things well and developing good business relationships. Neither alone is sufficient. Many people make the mistake of focusing too much on doing their work without building the kind of professional networks that will help them get jobs, move up at work, and change jobs when they need to. 

Women are so good at building social networks that they can be hesitant about creating professional networks as well. I think a truly successful life requires having good friends in addition to good mentors and colleagues. As a natural introvert, I made the mistake of keeping my head down and focusing on work to the exclusion of building the kind of mentoring relationships — with both male and female mentors — that would have helped me succeed faster.

No workplace is a pure meritocracy, and doing well in school doesn’t translate directly into doing well at work; you need to branch out and meet more people. Reach out to people whose work interests you and ask them about it. People like talking about themselves, if you make it easy for them to do so. 

In college, you can start by connecting with professors during office hours. They may be able to teach you more about the practice of their field than you can learn in class, and interacting with them is great preparation for the workplace.

The importance of focusing on the skills you love using  not the perfect job.

If you want more enduring career satisfaction (and who doesn’t?), find what you love being good at, and focus on learning all the different ways that people use those skills. 

Are you good at consensus building? Creative problem-solving? Writing? Look at what you’ve done in college, in class projects and extracurriculars, to help get a clue about that. And it’s never too soon to start looking at your volunteer and work experience in order to identify what you really enjoyed doing, and when you felt like you were adding the most value.

Focusing on the skills you already have and enjoy using, and then honing those skills and racking up associated accomplishments instead of job titles, will help you surf the job market and navigate career shifts in a more satisfying, sustainable and, ultimately, more successful way.

For example, if you like advising people, you could be a financial adviser, a lawyer, a guidance counselor, or a psychotherapist. Seeing yourself as any one of those things exclusively will artificially and unnecessarily narrow your career options.

The importance of mustering confidence, even when you don’t feel confident

There is an anecdote about a Hewlett-Packard executive who proclaimed that women working at HP applied for a promotion only when they believed they met 100 percent of the qualifications listed for the job while men, on the hand, applied when they thought they met 60 percent of the job requirements.  My take-away from this anecdote is that men are more likely to fake confidence than women, leading them to apply for jobs they are less qualified for. If women faked more confidence, they would apply for, and get, better jobs, thereby achieving more parity.  

So, at some point, you have to start faking it until you make it. 

I didn’t actually make it — in terms of genuinely feeling confident — until 10 years into my career, so I spent a lot of time acting as if I could do the job I was hoping to get. That worked fairly well.

It may help to think of faking confidence as extrapolating from evidence you already have, rather than lying outright. Pretend you’re advocating for someone else, if that helps. Every person who might hire you, or manage you, wants to know one thing: how can you, in particular, make their lives easier? Come up with a well-reasoned answer to that question, and you’ll be on your way to success. You actually succeed by delivering on that promise and by making sure the right people know about it.

Each of my three suggestions — making professional connections, zeroing in on skills you love using, and mustering confidence — may seem small in the grand scheme of things. But with more than 20 years of work experience under my belt, I know that they matter greatly. And focusing on them will absolutely help you prepare for a wide variety of rich and rewarding careers.


A version of this article originally appeared on Bentley University’s IMPACT blog at  

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Hiring Help: What Happens When You Work With a Life Coach?

If you’ve ever wondered whether you should hire someone to help you with your career transition, you may also have wondered what kind of help to get.  In this post, Deb Elbaum, a Boston-area life coach, explains how coaching differs from career counseling and therapy, and how one style of coaching – Co-Active Coaching – works in detail.

What’s your dream?  Whether you are a lawyer or other professional, there might come a time when you are ready to explore “What’s next?” You might crave an entirely new job or career that fills your days with more meaning and fun, for example, or you might desire more balance in your life. To help find the right path, many people work with a professional such as a career counselor, therapist, or coach. All of these professionals can provide support during a transition—and one or another can be useful at different times in the journey—yet their focus and approach usually differ. In general, career counselors help people define their strengths and interests to find a career path that’s a good fit. Therapists are especially skilled at helping people understand and resolve past and current issues that keep them stuck or dissatisfied. In contrast, life coaches—Co-Active Coaches, in particular—begin with where people are and focus on what they want to create going forward.

If you choose to work with a Co-Active Cdebelbaumoach to help you through your transition, you’ll likely encounter these questions—known as “Powerful Questions”—among those your coach will ask:

1. What do you truly want? – This is the time to dream big and imagine where you want to be in one year, or even five years. Imagine the impact that you want to have on others, your family, the environment, or the world.

2. What matters most to you? – This question helps you clarify what matters most to you — which values you are currently honoring in your life, and which values need to be honored more. When people are clear on what deeply matters most to them, taking a next step flows much easier.

3. What’s another way you could relate to this topic (for example, a job search)? – Looking at a topic through different lenses changes how you feel about that topic. Imagine, for instance, what it would be like to approach a job search as a chore such as cleaning a bathroom. Then imagine what it would be like to approach a job search as a treasure hunt with a certain promise of gold. How are they different?

4. What obstacles do you put in your way? – We all encounter obstacles that keep us from exploring or trying something new. We might come up with stories about why we can’t do something, for instance. Coaching will help you identify the obstacles holding you back and maneuver over or around them.

5. What will you do, when will you do it, and how will your coach know? – In coaching, you will keep your learning moving forward from one session to the next by pondering a question or taking action between sessions. You and your coach will agree on what you will do, your timeline for completing it, and how you will be held accountable.

Whomever you choose to work with—coach, therapist, career counselor, or other professional—be sure to bring your openness, curiosity, and motivation to the process. And keep an eye out for your treasure.

Readers, have you ever worked with a coach? What did you learn from the process?

Deb Elbaum, M.D. received her training as a Co-Active Coach from the Coaches Training Institute. She is also a Founding Fellow at the Institute of Coaching, a non-profit organization supporting research on coaching. She loves coaching individuals who are exploring “What’s next?” You can connect with her at or

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Reinvention: Do More of What You Love, Discover More of Who You Are

Paul E  Kandarian (2)Yesterday, a Boston Globe writer named Paul Kandarian profiled me in connection with the She Did It/Boston Conference, coming up on March 24 (get your tickets here!), where I’m moderating a panel on career reinvention for women over 50.  When I thanked him, Paul responded with a wonderful note about his own reinvigoration, underscoring the transformative power of doing more of what you love without knowing in advance where it will lead.  With his permission, I’m reprinting his note here:

After talking to you I realized how much I fall into the realm of which you speak. I’m 60, and have been a writer for 33 years, doing 15 years at a daily paper and since then, solely working as a freelance writer/photographer, embracing the uncertainty and magic of it in equal, energizing doses. But in the last 10 or so years, I’ve really found myself, as it were: I got into acting seven years ago and find it the most freeing experience of my life, giving me a level of self-fulfillment that continues to surprise and delight. And I’ve also gotten more into travel writing, a lot, and find myself winging around the world to write about exotic places.

These just happened by seeming accident, but when I really think about it, it was more about unwittingly designing my own life, as I think we all do, we’re all in charge of our own destiny, our own life’s design. I’d long wanted to act, just never had the courage to do it, but when I did, it opened a door for me that was incredible and incredibly unexpected in how it satisfies, and continues to feed a long-held yearning. And I’ve always loved to travel (I was a flight attendant in my 20s, believe it or not), so combining my writing ability with the hungering ache to travel was a perfect fit, and one that again, seemingly just happened but was most likely the result of my subconscious design.

I guess that’s the long version of confirming what you advise others, to find what it is inside you that you may not even know is there, and capturing its ability to fulfill, to satisfy, using the skills you already have. I do many things I find satisfying in my life, but the recent acting bug completes that in an way I’d never imagined. I shouldn’t say complete; life is not complete until you draw your last breath, it’s ongoing, changing, morphing into forms that bring much of why we’re here into crystal perspective.

Anyway, thanks for thanking me, but thanks mostly for realizing what we all have in us and guiding others into recognizing how to best bring that out. There is so much untapped human potential in all of us, I’m happy you’re showing folks the way!

Readers, do you know anyone who is trying to reinvent themselves later in their careers – say, 50 and up?  What challenges are they (you?) dealing with?  What helps?

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From Lawyer to Academic, Author, Distiller or Tour Guide

LAL3DI love profiling former lawyers who have carved out fantastic alternative careers for themselves.  Here are four very different paths taken by ex-lawyers, all of which, frankly, sound fascinating.  I’m especially drawn to the tour guide story, since one of my first and favorite jobs was leading tours as a high school student around the Massachusetts State House.  That early experience telling stories on my feet to a captive audience, and the thrill I got from doing so, no doubt played into my decisions to become a litigator and, eventually, a business professor.  Each of these former lawyers also tapped into something they love to do in order to find their next, and better, career (well, OK, except for the prize-winning novelist who is still a public defender).

1.  Robin Kelsey, who used to practice law in California, is the Director of Graduate Studies in the History of Art and Architecture Department at Harvard and has tenure.  According to Harvard’s website, Professor Kelsey is “a specialist in the histories of photography and American art, Professor Kelsey has published on the role of chance in photographic production, geographical survey photography, landscape theory, and the nexus of art and law.”  Art and law!  Kelsey has also written and edited books about photography, including “Archive Style,” on photographs and illustrations for U.S. surveys in the late 19th century.  Writing about old photographs sounds like a fantastic job to me, but the cherry on top is that he works with my favorite historian, Jill Lepore.

2.  Sergio de la Pava, who is actually still working as a public defender in New York, won the PEN award for his self-published(!) debut(!) novel about a public defender in New York.  Heads up for lawyers who love to write – including those of us who have always loved to write but who went to law school in part to make money – de la Pava won the most lucrative prize given by PEN, worth $25,000.   His story is also one of remarkable persistence, since he began writing his 678-page novel at work in 1998 and did not self-publish it until 2008.  The PEN prize came five years later.  His second novel, Personae, is also getting a lot of love from literary critics.

3.  Michael Lowe, who practiced law in DC for years before starting DC’s first distillery in over a century with his son in law.  Their small-batch gin, Green Hat, is getting national coverage from gourmets and praise from local upscale restaurants.  More about what makes their seasonal gin superior here.

4.  Jack Friedman, a former telecommunications and finance lawyer whose job was eliminated in 2008, when he was in his late 50s.  After working with career coaches, Friedman decided to create an entirely different second career: he now leads student tours, primarily in Washington DC, New York, Philadelphia and Boston.   He says that his new job allows him to combine his love of travel with his interest in working with young people.  It also allows him to use some of his legal skills, like speaking in front of a group and doing advance research, but he gets to set his schedule and only works four to five months out of the year.

For thirty more stories of former lawyers who love their new careers, read Life After Law: Finding Work You Love with the JD You Have.  It makes a great Valentine’s Day gift for the unhappy lawyer in your life (is that you?).

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Unhappy in Law: When Is It Time to Leave?  

LifeAfterLawYou’re practicing law, but you have doubts.  When should you start acting on them?  While there’s no universal answer, there are a few good guidelines.

First, it’s never too soon to start keeping the kind of notes that will help you figure out when and how to leave.  Don’t sit with a vague feeling of discontent indefinitely.  Instead of simmering, fuming or venting your general frustration, start a list of notable specific experiences (not on your work computer, please). List incidents, projects, and interactions that you enjoyed and those that frustrated you.

Focusing on your subjective responses to what happened, so that eventually you can get a grip on the particular drivers of your unhappiness.  Writing this down – and I don’t think there is a good substitute for writing – will help you form a detailed picture of what you do and don’t like about law.  Are the work conditions getting you down?  Does how much, when and/or where you work chafe at you?  Is it the skills you’re asked to use, or praised for? The subject matter? All of the above?

The point of this process is to figure out what, if anything, you like about what you do – otherwise known as your “preferred skills.”  That, in turn, will help you figure out what skills you want to draw on in your next career, and what value you have to sell to other employers.  Knowing your preferred skills drives your elevator pitch; it also drives your networking process by helping you figure out whom to target.  That process, in turn, will help you get clarity about where you want to use those preferred skills.

Should you leave before you have your next gig lined up?  I did this myself, and while I don’t recommend it as a general practice, some people need the time and space away from work that only a career break can provide in order to think critically about their own future.   Vacations, even the rare two-week kind, don’t usually cut it.  It is especially challenging to answer the “so what do you do?” question at parties when you are between careers, but you’d be surprised at the number of people who have tremendous respect for – and often envy of – people with the courage to make that kind of change.

Now, sixth and seventh year associates are in a unique position.  As partnership decisions loom, these associates tend to face  more suspicion in leaving law than more junior or senior lawyers.  Their advantage, on the other hand, is that they have more work experiences and perhaps more volunteer experiences to draw on in proving their preferred skills.  The upside of shifts in the legal profession is that more and more people outside of law  – more prospective non-legal employers, more friends, and more parents – who understand that partnership is no longer guaranteed even for wonderful happy lawyers.   The stigma of leaving law is diminishing all the time.

Above all, don’t wait too long to leave.  While I’ve never met any ex lawyers who regretted leaving the law, I’ve met far too many who wish they had done so earlier.

Readers, what told you it was time to leave?  How did you take those first steps?

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More Support for Your Brilliant Post-Law Career

crossing_the_chasmIn this season of Thanksgiving, I’m grateful for everyone who helps unhappy lawyers find and excel in non-legal careers.  In addition to the practical advice and inspiring stories in Life After Law, there are a number of great resources out there for lawyers considering a big change:

Marc Luber’s JDCareersOutThere offers terrific advice for lawyers exploring and changing careers.  His “JD Refugee” videos, for “people who are applying their legal skills without practicing law,” should be one of the first stops for JDs considering alternative fields.

Chelsea Callanan’s Happy Go Legal is a coaching service that focuses on new lawyers, but applies a holistic approach to help all lawyers find the best-fitting career.  Callanan’s blog and podcasts expand the resources she offers for becoming happier and more successful in whatever you choose to do.

Pace School of Law’s New Directions for Attorneys is a six month career re-entry program for lawyers who have taken time off and want to move either into a legal or an alternative non-legal career.  Graduates absolutely rave about this NY-based program, and the staff is phenomenal.  The next session starts in January 2014, and there is an info session on November 18 in White Plains.

And speaking of career reentry, I can’t recommend iRelaunch highly enough.  Carol Fishman Cohen and Vivian Steir Rabin have helped thousands of people (including loads of lawyers) relaunch their careers in a wide variety of fields.  They offer ongoing training, run conferences around the world, and their newsletters are unusualy useful.

If you’re looking for holiday gifts for yourself or your favorite unhappy lawyer, may I offer some suggestions in addition to Life After Law?  One is Allison Rimm’s The Joy of Strategy, which helps readers prioritize and manage their lives in a way that maximizes joy.  Rimm is a former VP at Massachusetts General Hospital, a gifted coach and a great writer.  Whitney Johnson’s Dare Dream Do is another great choice for people who are trying to envision something better for themselves, but need help getting unstuck.   Johnson is an influential Harvard Business Review writer and blogger whose practical wisdom and inspirational messages combine beautifully in this book.  And although it’s a classic, I’ll say again that doing the flower diagram in What Color Is Your Parachute? changed my life.  What a thrill to see Life After Law “frequently bought together” with WCIYP on Amazon!

Readers, what other resources helped you with your transition?  Whose help are you grateful for?



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