Return to BigLaw? A Reality Check

I have received several skeptical comments from someone calling himself Mr. Reality, who seems to take pleasure in belittling my search for fulfillment after BigLaw. You can see the comments.

These comments contain numerous mistaken assumptions about my personal situation, some of which I’ve corrected. But his most recent comment on my post on “Schadenfreude Among Friends” gives me a chance to do a reality check on my “journey of self-discovery” after nine months.

The comment asserts that I resent my former BigLaw colleagues as I see them climbing higher in their course. To the contrary, I am happy for them. I have had brief moments of wistfulness as I think about the path I’ve left behind, but these moments have never led me to second guess my decision to leave law (as I noted here).

The comment also implies that the schadenfreude I described was due to resentment at my friend’s success in my former field. That’s not the case. My friend’s promotion was not even law-related. There was resentment, but it was due to her ungratefulness, not her success.

But Mr. Reality, by challenging me to give up the search and go back to law, unwittingly gets one thing right: when embarking on the unknown, it is tempting to go back to what you know.

Leaving behind something I found to be unfulfilling was just the first step. Finding fulfillment takes work, a lot of hard work.

I didn’t fully appreciate how hard it could be when I left BigLaw. I dealt with the more immediate hurdles (or “niggles” as I called them): the loss of income and professional prestige. Overcoming these hurdles was only the start of the journey.

The core of the journey has been self-discovery. I find that the most important ingredient to finding passion is to honestly know myself. I constantly ask myself clarifying questions: What do I enjoy? Why do I enjoy it? Are there any unproductive emotional hooks that could mislead me into pursuing something? Am I any good at it? Will I have the perseverance to improve and master the skills? What expectations do I have in pursuing it as a career? Are these expectations realistic? Will my passion subside over time? Can I make a living doing what I want to do?

Over the past nine months, I have actively explored many options. I dismissed some, put others on the back burner, and am now pursuing one. I am actively looking to own and run a local business in an industry I love, whether through acquisition or by starting something from scratch. I am eager to be a businesswoman in this field and make it my career. The need for confidentiality prevents me from sharing more about the experience now, but I will in the future when I can.

People may not be impressed by what I intend to do, and that is okay. Thanks to what Mr. Reality calls my “self-satisfying navel gazing,” I have been able to identify and work through my insecurities. These “navel gazing” sessions have empowered me to resolutely move ahead. I say more power to my navel!

As I stand at the cusp of forging my new career, I am scared – just like when I took my first step in my high rope course in Montana. The solid ground – the familiar rung of the StairMaster that is BigLaw – can seem safe. But like the whisper – the siren song – I know that returning to BigLaw bears the alluring promise of safety.

Yes, I do have fears.

I fear the unknown. I know I will face challenges that I will not be prepared for. When I face these challenges, will I have a rude awakening that the path I am on is just an illusion, a case of grass-is-greener-on-the-other-side?

I fear failure. I may fail spectacularly, and in a public way before loyal supporters and taunting spectators alike. Above all, I fear returning to the enticingly convenient and seemingly safe rungs of the StairMaster. I would have failed to push beyond my comfort zone. I would have wasted this rare opportunity to take charge of my own happiness.

And if I didn’t make good on this opportunity now, then when?

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31 Responses to Return to BigLaw? A Reality Check

  1. A fan says:

    Good for you not to let the naysayers bring you down with their caricature and insulting assumptions — those comments say more about them than about you. It’s easy to taunt from the sidelines; it’s hard and brave to do what you are doing: refusing to accept the easy path and pushing forward to create a new future against the inertia of the familiar.

  2. daniel says:

    nice post. i commend you for taking the high road and not getting into catty fight with mr. reality.

  3. Helen says:

    I wholly commend your search. As someone who has searched, and continues to search, I so admire the road you are on. I also fully respect how you blog about the potholes along the way, and that you have found direction. Better to have lived a life fulfilled, than to just plod along. Maybe Mr. Reality is actually jealous?

  4. Daniel says:

    Hi Jennifer, different Daniel here from same name above. (I’m the one with whom you’ve been trading some great discourses and thoughts on your past writings.) First, I agree with everyone above.

    It’s amazing the bravery people show when they leave what can be seen as a cushy lifestyle, or job vis-a-vis salary, benefits, etc. You did that. I did it. You are a testament and inspiration to those of us who follow that path of self-discovery, and willingness to jump into the pool, instead of just dipping our toes in it. Moreover, you handled someone who came at you with vitriol and nastiness with class and dignity.

    I believe (not sure) that I mentioned that in your Schadenfreude blog that some people who carry themselves in such a way are unhappy with their own lives. If that’s the case with Mr. Reality, perhaps his writings are very telling, and maybe he was feeling what you felt, but for whatever reason, has not been in a position to act on it. We’ll never know, and I hope he doesn’t construe my comment as being a slight on him. We’re just all wired differently.

    Leaving something that is more lucrative for a path that is less lucrative and uncertain isn’t easy. As I said, I did it. I have no regrets. I’m very passionate about what I do, I live comfortably, and I don’t look back, not even for a second. I get to use my creativity and have an effect on others directly, when I teach in my discipline. Some life experiences, on which I won’t elaborate right now, made my decision easy. That isn’t to say that the uncertainty isn’t scary. Unconstructive criticism from others can feed that uncertainty. But our experiences constitute our journeys, and they help us navigate them. And they don’t just tell us where to go, they tell us where not to go, such as not to live our lives in six-minute increments if that turns us off.

    The option which you’re investigating now, I certainly hope that if it draws you to it, you’ll find success. And that just isn’t limited to money.

    Again, bravo to you for your resolve, and bravery in facing uncertainty. You’re sure not alone.

    Again, comments welcome…


  5. Hattie_PLU says:

    ns we make, it is their way of discharging their dissatisfaction and discomfort with their own lives.

    Like you I am going through a career transition right now and am establishing my own niche in the world from which I hope to create an alternative way of living; I’m designing my business around my life and hope never to be dissatisfied with work life balance ever again.

    Love your posts as always – this blog is one among a small handful that gave me courage to take the leap!


  6. Karen says:

    Forget this hater Jennifer. The coward doesn’t even have the balls to reveal his true self. Anyone can bitch behind a false name. What a loser!!!!!

  7. Careared says:

    Well said! I can relate to the challenges of charting a new course after leaving the law. I’ve really struggled with it since I left my job last summer. I’ve been putting a lot of effort into starting my own business, but I’ve had a few tempting offers from former contacts (non-law firm but still in the field) that have really made me look hard at my goals and think about the best path to the future I want. Saying no to something that won’t really move you forward along that path is hard, especially when the alternatives are so uncertain, but it’s so important to identify what will put you right back on that stairmaster.

  8. Dan says:

    While Mr. Reality is not entirely without his own faults, he does offer you some feedback that is something other than the typical uncritical adulation of your other blog comments. If you can learn from any of his criticisms, his blog comments are likely to be among the most helpful you receive.

    I hope you enjoyed your Boston trip. I’m envious.

  9. Gillian says:

    Great piece. I’m currently wavering on my decision to take a plunge into the unknown and your post gives me the support to follow my heart. Thanks!

  10. Zk says:

    I think mr. reality made a lot of assumptions about you and why you do what you are doing. I find his comments quite a bit condenscending. While it is great to receive constructive critique, it is not going to help if it is hurtful.
    On the other hand, it is one of the negative opinions out there and we better be ready to deal with them.

  11. STB 1st yr says:

    JP beat me to it, but I second the rule about blogging (and the internet generally).

    Sounds like this particular troll did provide a nice opportunity to reflect though. As always, thanks for the writing. Eager to hear about the business venture that you’re planning to pursue.

  12. JP says:

    First rule of blogging?

    Don’t feed the trolls.

  13. Lisa says:

    I really appreciate what you’re thinking about here, especially because my own blogging experience this week has been… quite interesting.

    It’s funny that your naysayer has been calling himself Mr Reality, because I find that a lot of would-be dream-crushers feel that’s what they are: representatives of some harsh “reality” that we all need to bow down to. Dealing with one “Mr Reality” is an education in dealing with them all, and valuable practice in standing strong in ourselves.

    Keep going in spite of your fears. Your journey is yours alone, but there are fellow-travelers all along the way. 🙂

  14. Giving it another go says:

    Although Mr. Reality has made assumptions about you, which are unnecessary and inappropriate, and he takes a more negative slant on life, he has some interesting points worth pondering. As you have mentioned in previous posts (I think), you are very fortunate to be able to quit your job (BigLaw or otherwise) to pursue your dream, your true calling. Most Americans are not in that position, more likely than not because of their financial situation. I do not interpret Mr. Reality’s posts as “dream-crushing” or beliefs which we need to bow down to. I think Mr. Reality has made a very valid point — your life, as it is right now, is not realistic; you are indeed privileged. Especially in this economy where unemployment lines are blocks long, people are barely making ends meet, and children in this very country go to bed hungry, your posts (albeit thoughtful and enjoyable) are not reflective of the real world and can sound, to some, like rants of a spoiled individual (even though that may be far from the actual situation). Life is more than searching for your dream career. Fulfillment is something entirely different for most people. Your journey is scary, but life is scary in so many other ways right now for so many people.

  15. Anon says:

    I’m not sure that I agree with you about what Mr. Reality’s point is here. I read him not as suggesting that Big Law is the only thing that will fulfill you. Instead, I read him as exhorting you, not as politely as he might, (though I think that’s intentional as well) to be productive in something, anything, rather than what he percieves you to be doing, which is, for lack of a better word, nothing.

    As I understand Mr. Reality’s view, it is the contributions we make to society that define us and give our lives meaning and he views your attempt to take time off and assess where you want to go as detracting from the very meaning that you seek. Just one opinion here, and I may not be reading him correctly.

  16. JP says:

    GIAG says:

    “Life is more than searching for your dream career. Fulfillment is something entirely different for most people. Your journey is scary, but life is scary in so many other ways right now for so many people.”

    Life is actually doing what you are supposed to be doing, which may or may not involve your day job.

    Life is scary for so many people right now because so many people have collectively made bad decisions. For example, if massive fraud (and/or massive financial stupididty) hadn’t been committed by about 20% of the U.S. population, we would never have had the financial crisis.

    As a general rule, life becomes scary when people (individually and collectively) make bad decisions. See all the history books ever written for further details.

  17. now a Münchnerin says:

    Nice post. I think of Biglaw as a treadmill too! Good luck with figuring out what is right (it does take time) and don’t listen to the negativists.

  18. I says:

    I envy your courage, it takes big ones!

  19. NTY says:


    I think it requires great courage to give up a good job to embark on a journey of self discovery like you are doing.

    There is no reason or excuse for Mr Reality to disparage you or what you are doing.

    I enjoy reading your blog because you write with such a personal and honest voice. Thank you for sharing your experience with us.

  20. PathFinder says:

    I used to work in IT for Wall St investment banks. I did not like my job. Now I still work in IT but for a government research organization. I like my job much better now. I tried a few things before landing my current job. And I hated one of them even more than my Wall St job. While I am reasonably happy with my current job, I’m not completely content. I’m still looking for new opportunities. For example maybe I can do a PhD so I can get more involved in research.

    So even if you don’t succeed in your next venture, I wouldn’t call it a failure. It will help you in finding something you like. And sometimes it is a never ending journey. So do not fear failure. You’ll never know if you don’t try. Having followed your blog I feel I know a bit about you. I’m certain you will succeed eventually. Good luck.

  21. rain74 says:

    Holy crap, Mr. Reality is such an ahole. Not surprisingly, he’s a lawyer. Yes, go back to BigLaw and deal with those types of Mr. Douchebags. NOT! Clearly he is either a first year or a partner.

  22. Mr Reality says:

    Well, your hagiographers really didn’t like that last comment of mine.

    Honestly, it was a bit snippy. I’m sorry.

    Its just that this blog had such potential. As a practicing attorney (I lead a litigation practice group here in NYC, in an office buidling not too far from your former employer) I was immediately hooked into your topic and “journey.” What fantastical lands would you discover? I imagined you erasing the “here be dragons” domain on a future life map of mine.

    But nine months later and your posts sound like all my new-money friends who sold their businesses too young and now travel too much. They got bored of maragritaville and started volunteering, or collecting cats, or they disappeared into themselves going on strange diets. A few returned to reality, started a new business and got back to themselves.

    I think the isolation of all that freedom gets to them. When we leave our career, what we also do is leave our tribe, part of our identity, our compass.

    In your case, you’ve had nine months of idleness. Your posts have turned increasingly inward, yet you remain defined by others – this post alone is proof of that.

    For me, this journey is over.

    -Mr Reality

  23. XCD says:

    Translation to the above post:

    “Well, your hagiographers really didn’t like that last comment of mine.”
    Translation: I’m jealous you have a groupie and apparently they all think I’m a douche-bag.

    “Honestly, it was a bit snippy. I’m sorry.”
    Translation: I totally agree with the douche-bag bit … even my mother have told me so.

    “Its just that this blog had such potential.”
    Translation: Hopefully my subjectivity will bring me some attention.

    “As a practicing attorney (I lead a litigation practice group here in NYC, in an office buidling not too far from your former employer) I was immediately hooked into your topic and “journey.””
    Translation: I am a creeper … watch out now!!!

    “But nine months later and your posts sound like all my new-money friends who sold their businesses too young and now travel too much. They got bored of maragritaville and started volunteering, or collecting cats, or they disappeared into themselves going on strange diets.”
    Translation: In REALITY, I hang around w/ a bunch of drunken slobs who can’t get a decent job and can’t afford food.

    “A few returned to reality, started a new business and got back to themselves.”
    Translation: Reality finally kicked them out of their parents’ basement and they got a job at the local McDonald’s (Mmmmmm…Big Mac)

    I think the isolation of all that freedom gets to them. When we leave our career, what we also do is leave our tribe, part of our identity, our compass.
    Translation: Deep down I envy those slobs, work sucks and I hate my life.
    – Maybe your compass can help you find the stick that’s rammed far up your @$$.

    For me, this journey is over.
    Translation: I’m going to go creep on somebody else now … maybe an accountant this time. I dig chicks in glasses, reminds me of my mom.


    Mr. Reality, I bet you got picked on a lot as a kid in school. Definitely explains why you are so bitter … and a DOUCHE!!!

  24. Reality Bites says:

    OK, I can’t stay silent any longer.

    I am more or less with Mr Reality on this.

    As a former attorney this blog really captured my attention. The first months of post were full of fascinating insight into things that concerned anyone who is familiar with a biglaw environment. Those posts really spoke to me.

    And then it just drifted. A bit, if I can say so, like your time off. I was hoping for something that would really delve into the comparisons of the world out there versus the biglaw life, but there have been lots of posts about animals, sleep ins, and seemingly erratic journeys to find yourself (eg SXSW or whatever).

    Hey, I’m not criticising here, but as far as the blog goes, it has clearly gone in the direction of a personal blog of self discovery – which is fine – but with very little connection to the initial premise of life before and after Biglaw. Which again – a million times – is all good for you, but is not really distinguised from a million other blogs out there of people trying to find their personal bliss.

    As for your personal journey, look I think you might be surprised in a decade or two about what Mr Reality is saying here. I think he’s both right and wrong. If this break was about you stepping back and finding yourslelf, then I hope it’s worked.

    But I would counsel this, ESPECIALLY TO ANYONE IN BIGLAW READING THIS. I write this from deep and very long personal experience.

    The vast majority of you will get no more than two or three shots to take time like this, if you are very, very, lucky, before your retirement. Make the absolute most of it. By that I mean – do the things that you could only conceivably do in brackets of that time. Go and live in Paris. Go and get your Cordon Bleu credentials. Learn Spanish. Whatever. Just make the God damn most of it.

    As for personal growth – and this is the real climax – you CAN do that in your job. It is the very circumstances of having experienced scarcity, of having experienced real money (to go with your experience of having had none in college), and of reflecting deeply by the force of the circumstances you are put into, what you are good at and less good at, what you like and dislike – all of this is a journey of personal growth.

    If you can stand the work, then I would strongly enourage those to use their time in Biglaw to figure out what it is they want to do, before they make the jump and turn off the spigot of cash. In my experience, you are much better advised to make every effort to get into your new career with a running start, than just throw everything in and ask yourself “now what”.

    You can use your time in Biglaw profitably while you are paying off your loans. So my counsel is simply this: try and discover your bliss – or at least make progress towards what interests you – while you are still in the job.

    To be clear, I am not criticising the personal choices of the author here. We all have our own limits, and our own pathways. All I would like to suggest is, this isn’t the one I would have chosen, or necessarily what I would counsel others.

    Nevertheless, let me end on a bright note. You are clearly a very bright and able person. I personally believe you will eventually find what you want – whether it’s on this watch, or in another 5 or 10 years. You have plenty of time.

    Good luck to you, and everyone else here searching for an alternative to the linear life of career law.

  25. jPM says:

    Good blog.

    Remember, though there are many of us who never got into Biglaw and never banked the money and paid off our loans to enable us to go on a “voyage of self discovery.”

    Even if I hate my job I still have to keep at it as I have $100,000 in student loans and I am single. I work paycheck to paycheck. Just saying!

  26. jPM says:

    Are you married?

    If your spouse is making bank and you can go on their health insurance, how “brave” is it to quit Biglaw? Sure, you might have to tighten the belt ….but the spouse can still provide the roof over your head, food, bills paid, insurance etc…while you find your way.

    Try quitting Biglaw when you are single or have people depedning on you. Now that’s brave…or some might say foolhardy.

    Also I wonder why the blogger did not look into other areas of the law with more humane hours. With her stellar credentials I am sure she could have got another job with a Fed agency for example….ok not making us much money ..but with more balance.

  27. jPM says:

    “I went to a public law school instead of a higher ranked private one so that I wouldn’t rack up a six figure student loan.”

    Well let’s be honest…it’s not like Boalt is some dumpy state u law school…it’s a top law school at a very reasonable price.

  28. JPM says:

    Not really. When your husband is making bank as six minutes has been quite happy to admit.

  29. JPM says:

    I give the blog owner credit for leaving to do what she wants to do.

    However, I have to take issue with posters who keep praising her for her “amazing bravery” etc.

    The blogger was quite honest and upfront about the fact that her salary could be erased and it wouldn’t make much if any difference to their lifestyle. In other words, here salary was not essential for the necessities of life – it was play money.

    “My first step was to thoroughly analyze our family finances. Cold hard numbers help put things in perspective. Without opening the kimono, the bottom line was that we could still live comfortably on the same annual budget with just my husband’s income.”

    I give credit for that because far too often in America we get bombarded with Horatio Alger bs about how making it just involves “hard work.” People never dislcose the inheritiance or monied spouse for example.

    I’m not blaming the blogger. She just has a very easy choice. How many people would quit their jobs tomorrow to follow their passion if they had a spouse whose income would still allow them to lift comfortably? Indeed the blogger even stated that she quit knowing that she wanted to be an entrepreneur without even knowing the business she wanted to be in!!! Again, this is indicative of someone who does not have to worry particularly if things don’t work out, because for most people quitting without a business plan would be pure insanity – it would be career destroying and financial suicide.

    I enjoy playing Devil’s advocate as I have. Interesting blog and I have almost read every post.

    As for the blogger, she is obviously far smarter than me (although maybe I’m better looking). I am a lawyer and would have given my right arm (ok my left arm) for the opportunities for career advancement and income that she has had. I think in this economy many laywers will read this blog and certainly feel envious!

  30. Anonymous says:

    In addition to my earlier note, can I point you in the direction of Marianne Cantwell and Free Range Humans? You may have already come across her and the brilliant work she does there; I am currently enrolled on her Mini MBA and pulling together my own free range business having developed a dislike to battery farmed jobs myself.

    I continue to love your work – the vulnerability you demonstrate in each post takes true courage and for that I applaud you!

  31. Carly says:

    Your blog was a very significant inspiration to me at the beginning of this year when I was contemplating quitting Biglaw. I meant to comment then to thank you for giving me the push I needed to make my ultimate decision. Now, I hope my thanks is more meaningful because I did quit, and now I’m doing something I’ve wanted to do as long as I can remember – taking a year to travel around the world. I, like you, hope that this year will help me figure out what will bring me true fulfillment. All that I know is that law is not it.

    Something you said in this post resonated with me: “when embarking on the unknown, it is tempting to go back to what you know.” I know when I return from my trip, I may be tempted to go back to law because it is what I know. But I hope that I can be as resolute as you and continue to search for true fulfillment until I find it.

    Since you haven’t written a post in a while, I assume your new venture is taking up a lot of your time. Good luck with everything, and thank you again for your inspiration!

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