Confessions of a Recovering Tax Lawyer – 12 Things I Hate About Big Law

I am proud to welcome my first guest blogger to Lolabees.  I asked Amber to write a post I have been dying to have here for the past year.  Her courage and insight to leave a high-powered career and follow her dreams caught my attention.  And not only did she leave a career she had invested so much in, but she and her husband dropped everything to go on their 2nd Around The World Trip. That is something I wish I had the courage to do!  And they’ve got big future plans that don’t involve anymore time in the law office.  I asked Amber to share the 10 things she hated about law, but she couldn’t stop at 10!

Make sure you check out her inspirational blogs about her career change and her travels.


Confessions of a Recovering Tax Lawyer – Twelve Things I Hate About Big Law

 I was once trapped inside the body of a tax lawyer.  For 10 years.  That’s right, after three grueling years of law school and the bar exam, I found myself practicing as a tax attorney at the largest law firm in the world.  I got to fight the IRS for a living during 8 of those years.  That sounds great, right?  Who doesn’t hate the IRS (besides IRS agents, of course)?   Perhaps that should be the next ABC legal drama, “The Tax Practice.”  Believe it or not, it’s not as glamorous as it might seem.  Shocking, I know.  In fact, there are a lot of sucky things about being a lawyer at any big law firm.  They involve the day-to-day activities that somehow have not made it onto Law & Order, Boston Legal, or Ally McBeal.

1.    Billable Hours: Billable hours were the bane of my existence.  You think your boss micromanages you?  Imagine having to keep track of every 6 minutes of your time.  That’s what billable hours are about.  I had to write down what I was doing for every 6 minutes and then determine whether I could bill it to a client.  It was tedious and put such pressure on my time, even when not working.  I had to reach a minimum of 2000 billable hours and received a bonus for up to 2400 hours.  I generally “worked” over 3000 hours a year.  Break that down.  Not a lot of time for Saturday marathons of the Real Housewives or Keeping up with the Kardashians.  No matter how efficient I was at my job, there was always more work to do and more hours to bill.  Just see below how to tally the bill.  I know clients think I bill them when I sneeze, but I’ll show you below, that I’ve actually spared them from a lot of billable hours they didn’t realize.  Not only will you see the other 11 things I hate about big law, but you’ll see that clients were getting their money’s worth out of me.

2.    Lawyer Jokes: How many lawyers does it take to . . . .  Yep, I have not only struggled to deal with being the butt of many a lawyer joke, but when you specialize in tax, that just opens you up to tax and IRS jokes as well.  I faced it from multiple angles.  I won’t even bill for those… unless, of course, the client is making the joke.

Lawyer jokes
Not cool. Watch out. This might be billable. (Photo credit: mikemac29)

3.    Paper Pushing: Think of the most glamorous TV or movie lawyer you know.  Patty Hewes from Damages, Tom Cruise in The Firm, or a Few Good Men.  They are playing down and dirty, in and out of court, arguing with judges, bending the rule of law to aid their clients.  I did none of these things.  I was in an actual courtroom for about 30 minutes in my ten-year career.  The rest of time I shuffled papers.  I was a highly paid paper shuffler.  It was not even as glamorous as My Cousin VinnyBillable? You bet, even when not in court.

4.    Golden Handcuffs: So, you’re probably wondering what I am complaining about if I was highly paid? The salary and bonuses were great and got bigger each year, but the trade-off is being shackled in the golden handcuffs.  You adjust your lifestyle to match your income, recognizing the salary will only increase.  What good is all this money if I did not have time to spend it?  Plus, with six figures of student loans, how could I quit this glamorous lifestyle?  Billable?  At least some of those billable hours trickled down to me.

5.   Skits, dammit!: During our professional development and training meetings, of which there were several each year, I often had the opportunity to do role-playing and skits.  Imagine a bunch of highly professional tax lawyers sitting around a room on a weekend doing skits.  Don’t see that on TV.  Billable? Unfortunately NOT billable.  But think about how that enhanced the services I was able to provide.  See, clients got that part for free, although I know many clients might pay to see some of their high-priced lawyers do some of this stuff.

6.  The “I’m Really Important” complex: People, we’re not curing cancer here. It often struck me how stressed my colleagues were – everything was a deadline, a time crunch, super important, do this “ASAP”, clients were in need.  Everyone was getting all riled up all the time.  Many of them meant well and had the honest feeling that what they were doing was incredibly important, as a member of the bar, upholding the rules and regulations of the government – the law of the land.  But it was difficult to get them to put things into perspective; to stop and eat lunch; to see their wife or kids.  Our job was to aid our corporate clients in paying lower taxes.  Like I said… we were not curing cancer.  I did not become a lawyer with hopes of changing the world – good thing, because I did not even come close to changing the world, other than keeping tax dollars from the fisc.  What these lawyers needed, was a little perspective.  Billable? Those hours would be more justified if we DID cure cancer.

7.    Environmental Catastrophe: I often wondered how many trees I killed as a lawyer.  I may, along with my peers, have been single-handedly responsible for killing a rain forest.  When I started in the legal industry, everything was on paper.  Everything we turned over to an opponent, the government, or a court, was on paper.  I learned that the boxes we used held 4000 sheets of paper exactly.  We would produce maybe 25 boxes a week during a 5-month project.  Add that up.  Even now that everything is “digital” the printer outside my office was constantly turning and burning.  If you want to become a lawyer to “change the world” think about the environment you are killing.  Billable?  Sadly, the bill includes printing costs…charging to kill the environment.

Paper Weaving
(Photo credit: FeatheredTar)

8.    Document Review: You can’t just turn over all those pages to the government without looking at them first, right?  Although document review is now generally electronic, it is still tedious, repetitive, and boring.  There is no way to sugar coat it.  For me, the apex of my document review career came in 2007, when I had to needlessly re-review 11,000 pages of documents in about 24 hours based on the whim of a partner.  All that mouse clicking caused tendonitis in my right wrist, which still flares up today.  Still thinking about going to law school? Billable? Time spent reviewing documents, most definitely.  Time spent at the doctor, icing down my wrist and going to acupuncture – fit into my non-billable “free” time.  The client wins one here.

9.    Complaining Clients: Big firm lawyers are expensive, I understand that.  I would try to find ways to watch the bill – have a cheaper lawyer complete a task instead of me, ask my assistant to do some internet research because she is free, etc.  I felt an ethical obligation to not try to maximize the bill to squeeze every last dollar out of my client, ignoring that my clients were Fortune 500, many with deep pockets.  So, having to hear complaints from clients about how expensive we were, or being the butt of jokes and jibs about how we must be overcharging, gets old.  If the clients could do the work themselves, then just do it and stop complaining.  By the way, my practice group was worth it.  We generally won.   Billable?  Hell yeah and we were worth every penny.  What would you pay to win?

10. April 15: I defended clients against the IRS, years after their tax returns were filed.  Yet, any time I told someone I was a tax lawyer, they would make some reference to April 15 being a busy time of year because of the IRS’s tax filing deadline.  I don’t file tax returns.  That is an accountant.  I was busy all year round.  Billable?  I billed all year round, not just in April.

11. Pointless Court Demands: When I did file documents with a court, I was always amazed at how specific the requirements were for documents – a certain kind of font, specific margins, a green or yellow cover page, use paper clips instead of staples.  Where does it end?  None of it changes the quality of the writing or the substance of the issues.  If we turned a document in with a white cover page by mistake, we could be bounced out of the court with grave consequences.  There are way bigger things to worry about!  Billable?  Clients complaining about the bill, take a look at these ridiculous requirements that made us bill for researching which color paper to use.

12. Blackberry: I remember when I first learned what a Blackberry was – it seemed so high-tech and gadgety.  When the firm first issued one to me, I was ecstatic. I felt free.  Little did I know that it would tether me to my job, virtually 24/7.  It was all abuzz during a Cubs game, during my haircut, while in the shower.  It took time to instill some discipline to not have it near me all day, but it was addictive nonetheless.  I often wanted to throw it off a tall building, or into a river.  I may have an iPhone now, but I will NEVER own another Blackberry as long as I live.  RIP RIM.  Billable?  Checking email on my Blackberry, billable.  Throwing it into a river, non-billable.

CrackBerry (Photo credit: kwolski)

Think about each of these things if you, or someone you love, ever considers going to law school.  I had a coveted, high paying job, which was hard to get.  If only I knew then, what I know now . . .

About Amber:
After 10 years as an attorney, Amber left her job at the largest law firm in the world and decided to start living her life.  She is now a recovering tax lawyer, traveling the world with her husband in tow.  This is her second RTW trip.  Her first RTW ended with a return to the tax world.  This trip hopes to explore Europe, Latin America, and ultimately end in a happy existence somewhere in Asia, where her passion really lies, outside the law.  Follow along at and


33 thoughts on “Confessions of a Recovering Tax Lawyer – 12 Things I Hate About Big Law

  1. It is refreshing to know that there are other professionals who feel this way. I wish changing careers could be easy for everyone though. After putting an immense amount of time, effort and money into becoming a dentist it is not easy to walk away and travel the world when I have a family who depends on my income. I am not happy and if I never drilled another tooth again I would not care in the least bit. I would like to know how Amber was able to drop everything and travel the world and what she is going to do with the rest of her life. Believe me, I would love to do that too but I don’t have a viable way out. It is sad that those of us who sacrificed so much to become professionals can end up being unfulfilled. Some people that change careers can do so easily but when you are trained to be a lawyer or doctor, have student loan debt and then become dependent on your “golden handcuffs” it is difficult to walk away without some big sacrifice. Also, there are not many people (other than other professionals like us) who really feel sorry for us either. They envy the amount of money we make and think that should make us happy. There is more than money to being happy in a career. I have not found my way out but at least reading this blog makes me feel better to know there are others out there who feel like I do.

    1. Thanks for your comments blueheron. A lot to digest there. First, we don’t have kids, so that makes things easier, but not impossible. I know a lot of people who travel full time with children and make it work. It also does not mean you have to change careers to travel, you can do something else, once you find out what makes you happy. Once I realized I was not meant to be a lawyer I started to save save save. We watched everything we purchased and stopped spending money on material stuff, in order to spend it on experiences. That made a huge difference to making me financial more stable so that I could be a lawyer so long as I wanted to be, not because I had to be. Check out this post ( And, this was not at all easy, it took years to plan, save, decide, and execute. I did not walk into work one day and decide to quit my career. It is a risk. I still have student loan debt (I am lucky in that I have a crazy low interest rate, low payment and it is paid years ahead). I agree that money does not buy happiness, so, we figured eventually we will settle down in a country that is a lot cheaper to live in and figure out how to make enough money to cover our expenses and my student loan payment, now that we have a nest egg. I plan to try to write, teach yoga, bartend, open a business overseas, I am just not sure. But, I am not sitting behind my desk miserable an wishing I had a different life! I wish you luck to find your path!

      1. I read the article from the link you sent me as well as some of your other blogs. Thankfully I am not in so deep that I can’t get out. Yes, we have a large home and one really nice car but we don’t live beyond our means. We have always been very careful about that. However, the biggest reason that I don’t walk away from my career is for my kids. I want them to have the best possible life they can and therefore, it is not easy for me to walk away-especially when I have a sure thing right now in terms of providing for them. I have changed the way I practice and reduced my hours so my schedule is very manageable at this point. I still don’t enjoy practicing dentistry but changing things did relieve some of my stress. I am probably going to have to put things off and really plan ahead if I want to get out. I may end up “retiring” early instead. At this point I continue to try to discover what I really enjoy and try to pursue hobbies that could spark an interest in something else. I am keeping my mind open but my children do come first. I am happy for you Amber and wish you the best. I enjoy reading about your adventures and I will continue to follow your blog. It will serve as a source of inspiration to me.

        1. I think you are already on the path to making something happen! I was stuck for so many years because I didn’t know what I wanted to do (and I’m still not sure what I want to do) 😉 I was able to eventually get out because I did what you are doing: “continue to try to discover what I really enjoy and try to pursue hobbies that could spark my interest in something else.” At least you’ll have something else you enjoy in the meantime and you won’t be totally defined by being a dentist. That helped me a lot.

        1. Thanks Robert – always great to hear another attorney find something useful in what I have to say! Stay true to yourself.

  2. SO PROUD OF MY FRIEND AMBER!! My second friend to follow their dreams. The first was a fancy agent at CAA (largest talent agency in the world…hmm, trend there with “largest”) who left his job in his early 30s to just…live. Be. Explore. We can all do it if we plan. We don’t need a lot of stuff to be happy. Being able to acquire experiences, as you put it Amber, is vastly more valuable than acquiring junk on an endcap at Grand Union. [had to throw in the bygone Jersey reference]

    Look forward to seeing you both should your travels bring you this way. We look forward to showing Max the world and will make a stop in Asia to drop in on you whenever you are settled.

    Luckily, the in-house world is a better fit for me than the firm life was. I could never go back to that world. Of course, it takes a little longer to save up “escape” funds when you are a lowly in-house counsel. 😉

    Happy trails, my friend………

  3. On one hand, I totally agree and relate (even though I am new to the legal profession – admitted to TX bar in 2011). However, I have yet to “practice” law so I would just like the chance.

    1. Thanks for the comment Travis. Yep, once you go to law school, its a godo idea to try it out for awhile. And, there are other places to practice law that are not big law, so hopefully you won’t suffer my fate!

  4. Oh goodness, I found this because I am working on justifying my decision to chuck it all and do something completely different. I didn’t work at a big firm – ever – but have slogged away as a small firm, small business tax/real estate/business lawyer since 2001. It’s never paid well, and the hours are long. Since I left the crazy world of small firm associate (low pay, long hours and insane partners), and went on my own, it hasn’t really improved. Yes, I can fire clients which is nice, but the money is not good and the stress is still off the chain. I am going back to school to be a petroleum geologist, I may not succeed but I suppose if I have to I can go back to law. I am not losing much, and the potential gain of being able to go outside is just incredibly appealing. Also, way more money. Don’t go to law school unless you have family/business connections or go to H/Y/S.

    1. Kansas, Just Do It! I know, easy for me to say, but I have never looked back. So long as your new education does not set you back too much coin in student loans, it seems like a good idea. Good luck and keep Laura and I posted!

  5. I’m a tax lawyer (mainly litigation) and love it. Maybe because this is my second career and I knew law is what I wanted to do. And I really enjoy tax practice. Could be much worse, I could still be a software developer. GAG.

    1. Ah, this seems a perfect case of the Grass is Always Greener anon. As a tax lawyer, while working on transfer pricing controversies, I met with dozens of software engineers and techies in Silicon Valley and elsewhere. Not only did they have a passion for their products that I envied, I learned about how many of them made a killing on stock options, IPOs, etc. I know this is not always the case, but seeing some of the numbers simply astonished me. I am glad to hear you have found your calling!

  6. This is perfectly describes my life as a tax lawyer! I am leaving this godforsaken profession at the 10 year mark and NEVER looking back.

  7. I have worked as a tax lawyer for 15 years and really enjoy it. The first 10 I was a litigator at the tax agency but now I have my own small tax firm and I haven´t had a bad day at work since I started my practice. Compared to working at a big firm I do not have to keep track of every last minute and just 1000-1500 billable hours gets me a better salary then most my friends working at big firms and time to watch my son grow up.

  8. I’ve practiced tax law for over 24 years at a high level and still generally enjoy the work – mostly sophisticated biz and financial transactions. Since I’m big law, I have to say that the best and the worst of it all relates to the other lawyers w whom I must interact. A few are both outstanding lawyers and people. I try to work with them as much as possible. Most of the rest are okay lawyers by big law standards, but without much of any attractive personality, to one degree or the other. So many, but not too many in tax though, really are driven by greed, or greed and power mongering, tho not really at an effective enough level to begrudgingly admire. Is more of a continual annoyance.

    Clients are okay once it’s clear you know more than they do in your area despite their periodic bombastic proclamations to the contrary, and thus, know how to confidently deal with the high and mighty (just make sure you’re damn right!). These client issues just take time and experience and maturity.

    A slight annoyance is having to train, over and over again, new generations of young clients as to how to use their lawyers (most don’t have a clue how to use this tool at their disposal) and also training new generations of young lawyers to think and act like lawyers must ultimately think and act like in order to be effective. Many young lawyer are caught up in the hype that surrounds media popular lawyers, not realizing that if you look closely at these media darlings you’ll quite often find a lawyer who possesses absolutely terrific fundamentals, but who also just happens to be a great marketer.

    In the and, unfortunately, the old adage of the law being a jealous mistress remains steadfastly true – there is no way around it if you are to engage in legit law practice for an extended period. It will absorb large blocks of this, your one and only life. You have to decide what you want and how best and most efficiently to get it. There’re no shortcuts and freeebies in this industry, whether you’re big law like me, a solo practitioner, a judge, work for the state or are in house, they all require you to bring your game each and a every day.

    1. Scott, Thank you for your comments. I think this career can work for some, but not for me. And, you are right, you come into contact with all kinds of lawyers and all kinds of clients, both good and bad. Now, that I have been gone for over 18 months, I can safely say I have never regretted my decision, not one day! It sounds like you have not regretted your decision to stay in the law. So, both good choices!

  9. Amber, sounds like you are still delusional about being delusional. Congrats on following your dreams, the problems is your dreams are corrupt. Just like all the people you work with, lipstick on a pig, is still a pig. Of course you guy’s justify what you do and how you do it, it’s what helps you justify it.

  10. The biggest problem here is that you are traveling the world to be happy as an alternative to practicing law. The mother of 6 or mother of none working in McDonalds for minimum wage probably in my opinion can’t afford going to Asia to get away. Complaining about a profession that has allowed you to travel the world seems a bit arbitrary in my opinion. Having experienced myself the nuances of poverty and the wealth of education. Suffering is in the eye of the beholder I guess.

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