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Christopher Guest Post: Big Law Investor

Welcome to the latest Christopher Guest post.

Today’s distinguished guest has been blogging for nearly a year. He has crushed his debt and put out a number of great posts on the topics of investing, debt payoff, taxes, and more despite his busy day job as a lawyer.

A what?!?

How did a #$(* lawyer sneak in here? Does this site have no criteria? No shame?

Well, to be fair, he doesn’t chase ambulances. He wasn’t the guy handing OJ the little gloves. He’s not John Edwards reenacting the birth of a cerebral palsy patient from the fetal perspective. Read on and you will learn that he is a corporate lawyer in New York City dealing with murders and executions mergers and acquisitions. Seems harmless enough.


What’s a Christopher Guest post?


Inspired by Nigel Tufnel, the character portrayed by Christopher Guest in Spinal Tap, I took Mr. 1500’s ten questions, and amped them up to eleven.


If you’re not familiar with the scene, take 50 seconds to watch this video and enjoy the dialog between Nigel and Rob Reiner.


I decided I’d start a Q&A of my own. Not satisfied with just ten questions, “this one goes to eleven”. Just like Nigel’s amplifiers.


Presenting: The BigLaw Investor


What do you do (or did you do) for a living? What do you like best about your job?

I’m a corporate lawyer that specializes in private equity mergers and acquisitions. That’s a fancy way of saying that I help my clients buy and sell companies in the private market.

I love the project management aspect of my job and the technical requirements of getting the drafting right. It takes a lot of work to memorialize the deal terms in writing and ensure that the pieces of paper reflect the precise agreement among the parties.

[PoF: Thank you for not suing me. And for not suing anyone. Your line of work does sound both interesting and productive.]


If you were a physician, what type of a physician do you think you would be? Why?

Given that I get queasy at the sight of blood, I think we can all agree that it’s a good thing I’m not a doctor. My doctor friends tell me that repeated exposure desensitizes you, but becoming a doctor is never something I considered seriously. If I were a physician, I’d likely quit seeing patients and turn to the business aspect of running a practice. I like people but I have no interest in seeing anything inside of them.

[PoF: Even as a hypothetical doctor, you quit your clinical practice right quick! I would say it is a good thing you never considered medicine as a career. 

There is some truth to the desensitization. I’ve heard well-known and highly respected physicians talk about how they nearly passed out at the sight of blood and smell of burnt flesh in their first O.R. experience. Personally, blood and guts don’t bother me a bit, but a finger cracked and bent completely the wrong way still gives me the willies.]


Describe your blog and tell us why your blog would appeal to a physician seeking FIRE in eleven sentences.

My blog is aimed at lawyers who surprisingly come in two distinct flavors: (1) high earners like doctors (although generally not as much money) or (2) public servants that are paid significantly less. [PoF: Like Financial Panther]

A physician seeking FIRE would likely find my blog interesting since I write about topics relevant to high earners. Physicians, like lawyers, probably don’t realize that whether they want to or not, they practically have a second job managing their money. This means you need to become at least proficient in financial lingo even if you plan on working with professionals to help you manage your money.

Some of your physicians on the lower end of the pay scale spectrum might find some of my writing interesting, particularly discussing PSLF and the various student loan repayment plans.

[PoF: I’ve read a lot of your stuff, and I don’t think a physician needs to be on the low end of the pay scale to appreciate your posts. 

I don’t think managing money is a second job — it can be done with as little as a few hours a year once you have done the necessary background learning. But you do need to put in the time to learn the lingo and understand where your money is and how to invest it wisely.]


Turks Caicos Beach
set it, (mostly) forget it, and head to the beach


What inspired you to start a blog of your own? Was there a particular event you remember that made you feel your blog had arrived? Any big plans for your blog in the future?

The White Coat Investor’s mission to deliver personal finance knowledge to doctors resonates with me. I’ve been reading Dr. Dahle’s site for years and always wondered why there was no equivalent site for lawyers. After some time, I figured I might as well create it myself.

Lawyers face different challenges compared to doctors and although it all seems very niche, I think there’s a voice missing that speaks to the specific circumstances of being a lawyer.

[PoF: The good Dr. Dahle has inspired quite a few of us, and I think you discovered his site before I did. Lots of good stuff there. If you can do for lawyers what he has done for physicians and their finances, that will be a huge win.

Although I must admit, there are certain lawyers that I wouldn’t mind seeing skip your site entirely, spend beyond their means, trust their money to a Madoff-type guy, and live unhappily ever after. 

And no, I’ve never been named in a malpractice suit [knocks on wood], but that doesn’t mean I haven’t been burned.]


Give me eleven posts you think Physician on FIRE readers might want to read.

  1. Secrets of a $100,000,000 Roth IRA
  2. Where Are All The Rich Lawyers?
  3. Should I Borrow Money in Law School to Fund a Roth IRA?
  4. Why You Should Be Getting a Big Fat IRS Refund
  5. Financial Independence: Do You Really Want It?
  6. How to Manage Tax Diversification Like A Boss
  7. Student Loan Refinancing Guide
  8. Contribute to a 401(k) or Pay Off Student Loans?
  9. Your Savings Rate is More Important Than Your Rate of Return
  10. 11 Financial Mistakes Lawyers Make and How to Avoid Them
  11. Why I Love The Roth IRA

[PoF: That’s quite a roundup. Regarding your #2, I found the bimodal distribution of lawyers’ salaries highlighted in Lawyer Salaries are Weird post to be fascinating. I think there must be a third spike far off to the right that we’re not seeing, but maybe that’s just a tiny fraction making the really big bucks.]



At what age are you most likely to retire (or at what age did you retire) from full-time work? What are you doing to help realize your retirement target?

Retirement is a loaded word in the FIRE community. Please call the Internet Retirement Police. I might never retire. Right now I’m working on achieving financial independence, which I think is equivalent to the same thing.

At this pace, I should reach financial independence by 40, but I’m not worried or focused on any particular age. I take every thing one day at a time and look forward to the freedom each dollar buys you.

To reach my retirement target, I am maxing out my 401(k), Roth IRA and HSA accounts each year. Last year I decided to pay off the remaining $75,000 of student loan debt. While it was at a low 3.03% variable rate, I’ve become a firm believer that most wealthy people don’t have student loan debt, so I decided it’d be a good idea to shed them and free up the cash flow.

[PoF: FI by 40 will match my feat — I know you’ve got a few years left, and I hope you make the goal. How great does it feel to be rid of those student loans?]


What does an ideal retirement look like for you? What will you do with your time when full-time work is in your rearview mirror?

Stirring Wine
the lawyer stirs wine. retirement gig?

An ideal retirement for me just means not needing to exchange time for money. It means waking up to work on the projects I want to work on and not having my schedule dictated by other people’s priorities.

When you think about, most of humanity has existed without a “job” mentality for quite a long time. It’s only with the recent rise of the corporation that humans have shifted to thinking about receiving wages in exchange for a commitment to a job. I spend a lot of time thinking about the behavior psychology of personal finance and all the scripts we’re programmed with. Having a “job” seems to be one of the big ones.

A good thing for both lawyers and physicians is that their practice allows them to pursue a more entrepreneurial type employment than the general population. I’m always looking for those lawyers.

[That sounds pretty great for a partial retirement. Oh, great… now I’m the retirement police. Your ideal job sounds like a good gig if you can find it in the law or business world. It certainly won’t happen for you in BigLaw.]


I’ll give you eleven sentences to dish out advice to a young physician. Any and all advice is welcome. We talk about personal finance, so money is fair game, but if you have advice on being a better doctor, a better parent / spouse / friend / human, we’re all ears.

  • I’ve been through a lot of bad things in my life, some of which actually happened. – Mark Twain.
  • Taxes are a huge drag, so start maxing out your retirement account as a priority before everything else.
  • Live like a resident for the first five years.
  • Write out an investment policy statement (tax rates, insurance coverage, portfolio, goals, etc.) [PoF: You mean Investor Policy Statement. ;)]
  • Approach stuff with the mentality that you already own everything that the world has to offer, you’re just keeping it in storage and have to pay a small fee to retrieve it. [PoF: That’s pretty revolutionary. Did a minimalist tell you that?]
  • Watch out for convenience.
  • Dripping water hollows a stone. -Ovid
  • The days are long but the years are short.
  • There is always an alternative path.
  • New York is the kind of place where you can earn enough money to solve problems that don’t exist elsewhere.
  • Sometimes the questions are complicated and the answers are simple.

[PoF: If you can make it there, you can make it anywhere, or so I’m told. A funny thing in medicine is that the New Yorkers generally earn less and have much higher cost of living than their counterparts throughout the nation. Geographic arbitrage has worked wonders for me, and I can still visit NYC whenever I want.]


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Use our link to Join and receive a bonus of up to $50 .


You’ve got eleven days to visit anyplace in the world with an $11,000 budget. Where do you go and what do you do?

Easy: I’m chasing summer for a year and following the major tennis tournaments starting with the Australian Open in January. After that, we’ll head to the US for tournaments in California and Miami, circle back through France and the UK during the summer months and then end up in NYC in September.

For $11,000 I might not be able to do it in a fancy way, but it’d be a great way to explore the world and see some good sporting events while I do it.


Djokovic US Open
the lawyers view of Djoker


[PoF: I love the chasing summer concept. Tennis isn’t my jam, but I’m down with that general itinerary.]


Name eleven beverages you enjoy. You can be as general or specific as you like.

  1. Carbonated Water.
  2. CogniTea.
  3. Barolo.
  4. Honest Iced Tea.
  5. Inns & Gun Rum Aged Beer.
  6. Mid-Winter Margaritas.
  7. Rosemary Maple Bourbon Sour.
  8. Beltane Ranch Rose.
  9. Root Beer.
  10. Shiner Bock.
  11. Lemonade.

[PoF: Shouldn’t that be a Brooklyn Lager in place of the Shiner? Looks like a good mix of beverages — mine is evolving. A few weeks ago, I gave up diet soda and effectively all caffeine, then went on to work my busiest month in years. Haven’t really missed it, surprisingly.]


Now, eleven foods.

  1. Lasagna.
  2. Steak au poivre.
  3. Pepperoni Pizza.
  4. Chicken Kiev.
  5. Brussel Sprouts.
  6. Coffee Butter.
  7. Okre.
  8. Short Rib.
  9. Shishito Peppers.
  10. Bratwurst.
  11. Pecan Pie.


[PoF: You just threw in the sprouts and okre to try to look good, didn’t you? It’s alright; I’d probably list broccoli on my list. It’s not among my favorite foods, but as far as vegetables go, I tolerate the florets quite well. The stalks, not so much.]


How did you first learn about PhysicianonFIRE.com? What one piece of advice do you have for me?

I was trying to log on to this dating site … [PoF: Oh, you mean POF. I was honestly oblivious to that until a reader pointed it out.]

ACTUALLY, I learned about PhysicianonFIRE from a post on White Coat Investor. I didn’t realize there were other physician personal finance blogs until I saw your post. It’s been great to see you struggle with “retiring” from such a high paying position. It seems like you want to move on to other endeavors, but I know it must be a challenge when you have a high paying job to leave (not to mention all the sunk costs around the training involved).

My only piece of advice for you would be to remind you that figuring out what is “enough” is perhaps the greatest challenge for financial independence, particularly for high earners. What’s enough for you PoF?

[PoF: I’ve read Bogle’s book appropriately entitled Enough and I’m still trying to figure it out. We’re rapidly closing in on some goals I outlined in a guest post a few months ago and should be able to check all those boxes by the year’s end unless we enter a bear market in the meantime.

As my wife and I start talking timing, the exit strategy has little to do with any dollar amounts. I’ll start my part-time schedule this fall and plan to give that a year or two. We’ll see what happens after that!]



BLI — Thank you so much for taking the time to share more of your story here. Readers, what questions do you have for the BigLaw Investor? Ask away!


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  7. The post completely shows a new side of a lawyer and his thought process in financial planning. Of-course, no one can guess what is the lawyers way of thinking and planning. 🙂

  8. Fellow BigLaw lawyer here (IP lit). I enjoy Biglaw Investor’s blog and he has a perspective that I can relate to. Great interview.

  9. I really like the top posts on Financial Panther. I will need to check them out. It’s so refreshing to get a lawyer’s perspective on early retirement. Thanks for sharing the great interview!

    • I mean seriously, right? It’s not like I’m hiding my identity either. You’d think Harvard would pick up the phone. I’d be happy with any low 7 figure off they see fit to present to me.

  10. Lawyers! Blasphemy. Actually I put our corporate lawyer friend as one of the top bloggers helping bloggers. He always has good advice, both financially and with the blogging stuff. Thanks for featuring him!

    I put Lasagna in my top food items, though rarely have it. I am going to have to rectify this quickly. Lasagna for dinner tonight!

    • Thanks DDD. It’s amazing how one can struggle with a problem for hours that can be solved by someone else in seconds. Just trying to pay it forward!

      I rarely have lasagna as well unless I’m at an Italian restaurant and then I almost always order the lasagna.

  11. Enlightening interview, and one that I will pass on to my lawyer brother!

    I know lawyers in each of those salary peaks. A friend working for the state bureau of professional and occupational affairs; he has a pretty sweet schedule and lots of “bank holidays”, but earns in the lower peak. My brother works for a medical malpractice firm (on the good side, i.e. for the insurance company), and falls somewhere near the higher peak. His schedule is a more typical occasional weekend work and 2 weeks vacation a year.

    Any advice for lawyers who might want to work part-time instead of fully retire early? Any particular areas of law more conducive to that?

    • So funny to hear you say “on the good side, i.e. for the insurance company” as I’d guess that a lawyers would describe it as “on the bad side, i.e. for the insurance company”. As a lawyer who has nothing whatsoever to do with medical malpractice issues, it’s been really interesting getting to know physicians and their take on the legal profession. Not to derail the conversation but I’m starting to understand where you’re coming from. However, if you are a doctor working with me it’s probably because my client is about to give you millions of dollars (so doctors tend to like me, even if I’m negotiating on behalf of my client).

      If you are a future lawyer that wants to work part-time, because a highly skilled specialists in a niche area that works for a biglaw firm supporting the M&A practice. If you think of the corporate team as quarterbacking a transaction, there are all kinds of specialists (i.e. labor/employment, IP, Privacy, Regulatory, etc.) that are called upon depending upon the specific facts of the transaction. Those lawyers often have the ability to work part-time in mid-level to counsel roles since their work is dependent on the total number of deals running through the M&A practice group.

      • Thanks for that info.

        I don’t really think of the lawyers themselves as “good” or “bad” (my brother has helped talked me through this); it’s more the result of a medical malpractice culture that is broken.

        When you say lawyers think working for the insurance company is “bad”, you mean they are not compensated as well? The almighty dollar has so much influence over us all, doctors and lawyers alike.

        • I think that’s what I’ve come to realize speaking with physicians – the medical malpractice culture is broken no matter how reasonable it seems in theory. As I said before, I have no connection to that industry so it’s fascinating to me to see how this influences a lot of doctor’s feelings about lawyers. I’ve tried to carry this forward as I do some work in the healthcare space and occasionally interact with doctors.

          Lawyers working for the insurance industry are compensated reasonably well but in general it has a reputation of being repetitive and not necessarily rewarding work (since you’re always in the position of defending an insurance company that is denying a claim). I’m not speaking from experience though (just anecdotal interactions with young lawyers that start in insurance defense and jump ship after a couple of years) so would be interested to hear your brother’s perspective if he’s enjoying it.

  12. Thanks for this feature, PoF! I wonder how many people that are looking for romance (Plenty of Fish) find your site and end up turning their financial situation around. That’s funny!!

    I just perused BLI’s site and subscribed. Excellent content!!

    • Now, if only I could find a way to get them to pay me for the feature. I do it out of respect.


  13. I love the Mark Twain quote “I’ve been through a lot of bad things in my life, some of which actually happened.”

    I’m with you that I’d love to travel around the world for the endless summer. That would be amazing and I’d love to pick up some new skill sets along the way. Like surfing 🙂

    Can’t wait for FI to come!!!

    • Mark Twain had a knack for getting something right in as few words as possible (I believe he’s also credited for saying in a letter, something to the effect of “My apologies for the length of the letter but I did not have time to write you a shorter one.”

      I definitely plan on having at least one year with an endless summer! I don’t know how PoF survives up in the Great North.

      • I think I might actually enjoy this second Mark Twain quote better! Lawyers are writers (of limited entertainment value), so we can relate to the value of brevity in all writing.

        Highlighted by what I did last Friday: Reducing the word count of an appellate brief from ~19,000 words to the word limit of 14,000. Precisely the word limit.

  14. It’s very cool to get to know BLI a bit better. I’ve subscribed to his blog as well.
    My roommate from college and his wife both attained their law degrees. We still enjoy educating and debating with each other about how lawyers and doctors could interact better and understand each other’s points of view when we cross paths.
    I’ve directed them to your site because they racked up some pretty substantial student loan debt and now he’s a prosecutor and she works for a university on the grant writing side of things.
    I’m with you on the endless tennis summer. I never thought of that one but maybe I can convince the wife to take that trip once we retire. Thanks for the idea. Did you play in school?

    Tom @ HIP

    • Thanks HIP. I’ve enjoyed reading your blog as well. I appreciate the referrals.

      I have played tennis only a few times in my life. Such a shame. If I could scale back my work schedule, it’d probably be the first hobby I would like to pick up. I didn’t really get into tennis until a summer in 2008 I found myself living in England and got swept up in Wimbledon. I like the hand-to-hand combat of seeing two individuals battle it out (and not punching each other in the face). You really have to win every point in a match. There’s no running out the clock.

  15. Thank you PoF for another great interview! I’m a subscriber of BLI investor too and the candid nature of your interview really adds a lot of interesting layers and perspective.

  16. Thanks PoF for featuring BLI, great interview. I am a subscriber to BLI’s blog and enjoy his writing, even though I’m not a lawyer (and have no desire to become one).

    BLI, what’s your take on the boom (and subsequent bust) in law school enrollment over the past 15 years? Would you recommend law to a young college graduate in 2017, especially if they can’t get into a Top 14 law program?

    • WSP, you say that you have no desire to be a lawyer but I think we all know that’s next on your list. It’s only the natural progression from trader to physician to lawyer (part time program? At Georgetown, you can go to law school for free.

      The bust has been great. A lot of people shouldn’t be going to law school as a JD isn’t the “jack of all trades” degree that it’s sold as. Turns out a JD is really good if you want to be a lawyer. I think the whole Top 14 stuff is bunk. Sure, you’ll have it a lot easier if you get into one of the top schools (mainly because the firms will come to your school to interview) but if you’re networking and taking advantage of your law school alumni, you can do just fine a little lower down the ranks. The key is to recognize that if you’re outside of the Top 14 your law school has the most influence in your region. Don’t go to the University of Alabama (which has a fine law school program) and think it’ll turn into a biglaw job in NYC. On the other hand, I know plenty of people that went to New York Law School or Brooklyn Law School that now work for the big firms in NYC.


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