An Interview with a 30-Something Retired Lawyer

Claud Mccoid

Biglaw salaries are weird. We talk about it all the time. Many people working in Biglaw are nowhere near meeting their financial goals despite their paychecks. We sat down via Zoom to talk about money and life with Anita Dhake, who paid off her student loans and retired at age 33 after working in Biglaw for five years.

She carefully tracked her expenses before starting her Biglaw job and made it a priority to pay off her loans as quickly as possible. She used her projected spending and her expected investment returns to decide on a number that she wanted her nest egg to reach before she retired. When she hit her number, she left Biglaw and started her retirement.

Now, she reads, travels, spends the day however she wants, and ticks off items on her life bucket list. Here’s what she had to say.

1. Tell us a little about your family and your childhood/background. What messages did you get from your parents about money when you were growing up? How did you view money when you were younger?

My father was a chemical engineer and my mother worked at Target and finances were a common topic of the dinner table. I knew how much my parents made, and they made me understand how much things cost. I understood when a want was out of reach and learned to make do with less. My parents lived on very little and raised three children while buying a house, owning cars, and helping with college costs along the way. I was able to focus on having enough and knowing what is important to me rather than being greedy. I knew what the numbers were for my financial goals even before starting law school.

2. Tell our readers a little about your legal career. What was Biglaw like? When did you know that it wasn’t what you wanted to do long-term?

Biglaw is exactly how you expect it to be. Famine and feast. You’re either drinking out of the fire hydrant or parched in the desert. You are expected to say yes to everything, and work comes before weekends, vacations, family, friends, everything. Reminiscing at this time in my life, my memory tells me it was a blast. I got to wear pretty dresses every day. I had my own secretary to fax stuff. Do people fax anymore?

The money was insane. Skadden had a gym with free personal trainers. Even if it’s a tough life, you’re surrounded by terrific people. The job let me pay off my student loans, accumulate a nice nest egg, and move to Sydney for a couple of years. After my time in Sydney, it became a natural stopping point since I had been plotting my exit for years and theoretically had enough money. I have no regrets and love the idea of my time there.

The reality is that I hated having a job. Really any job. Having to wake up at a certain time each day, long hours, devoting all of my energy to contracts to help corporations do something. It wasn’t for me, and I knew it from day one. I wanted to stay a year to get rid of as much of my student loans as I could. Then I decided to stay for one more day. I kept making the conscious decision to stay one more day. One more paycheck. One more deal.

During the first year when I still had student loans, I was super anxious. Because it was close to the 2008 recession, I was worried I might get fired at any time. Once my student loans were paid off, I no longer felt like a hostage to money and was instead choosing to build the nest egg up. It became easier to go to work every day and I felt more secure as my money accumulated. I could quit if I had to, and life got easier.

3. We’re curious about how you “knew” when you had hit your retirement number. Did any of it change during your career? What was your comfort level with your retirement savings number when you quit your job?

My initial goal was to accumulate $600,000. This would generate about $1500/month in projected passive income. This would theoretically be enough for me to live in Chicago. When I hit that goal, I was living in Sydney, Australia on secondment, so I finished out my contract and decided that was a good stopping point, retiring with more than my initial goal. It was five years to the day when I started working as a lawyer. I had been tracking my expenses for years and knew how much I needed to live on and since I’m a pretty simple person, it wasn’t much.

I was never a materialistic person so I could easily say no to consumerism and avoid lifestyle inflation. It seemed obvious to me to be smart with my money and I kept my eye on the prize from the very beginning. Although I felt prepared in theory with my finances, at the same time I felt a little bit of uncertainty of not knowing what I was getting myself into when I retired.

4. Are you more or less comfortable with your decision now that a few years have passed?

I love my life more than I can say. I am writing every day, reading many books, working out every day. It’s a leisurely life and I feel like I focus on the things that matter to me. Relationships. Experiences. My interests. But, I do experience the occasional bout of dissatisfaction. When I check in on Facebook every once in a while and see all my former classmates and coworkers doing great things, I wonder if I should have been more ambitious. When I see a direct flight from Denver to Managua for an absurd amount of money, I sometimes regret the path not taken. I could have afforded all the things! But then I disable Facebook and take an extra day in Miami on my way to Nicaragua on a more reasonably-priced flight and remember that I don’t actually want all the things. All the things won’t make me happier and, in general, working is not the lifestyle I want to have.

5. You were just starting out in Biglaw when the financial collapse of 2008 was happening. How did that affect you? How has Covid affected your retirement?

I got crazy lucky in that I interned as a summer associate for Skadden in the summer of 2008 before Lehman collapsed. I got my offer as per usual and they honored it. In 2009, after I graduated, Skadden gave me the choice of working for them or taking a year off with reduced pay and student loan help. I took that offer, of course, and took a year off exploring the world, hitchhiking across Ireland, working at a farm in New Zealand, waiting tables in Australia. If anything, the collapse affected me positively.

Covid hasn’t really affected my retirement in any way. The market keeps on chugging. Civilization continues. My expenses were lower in 2020 because I wasn’t going anywhere or doing anything. 2022 is going to be a big year for travel for me, though!

6. You’ve talked in other spaces about feeling like you’re skipping school while your peers are all stuck at work every day. Tell us a little about how being young and retired has affected your relationships—both friendly and romantic.

Honestly, I live in my own little bubble of friends that are early retired or semi-retired, so it’s pretty great. We can have lunch or schedule an indoor sky-diving lesson when it’s cheap or play golf when it’s nice during the day. Right after I retired, I traveled alone for over two years, and it did get lonely. I decided to settle down in Denver and my blog followers started to come out of the woods to meet and hang out. Many of them have become my community of relatable friends.

I’ve been dating my boyfriend now for nearly a year and he’s also semi-retired. He owns some property that he rents out. We spend a lot of time together. It’s great. I have to admit, before that, dating as a retired person was terribly difficult. I think a lot of men didn’t quite “get” what I was doing/trying to do and didn’t quite know what to make of me. They worked the traditional job and had all the gadgets and couldn’t imagine a different life.

While in Biglaw, I talked about finances with anyone that would be interested. My blog was public, and it had all my charts and numbers. I thought maybe if others knew what their options really were, that they would choose differently. I didn’t convince anyone, but I did get a lot of feedback and motivation from others.

7. The environmental impact of consumerism is a major issue. What are some things that you do or have done to reduce your footprint?

I always ask myself a few questions before I buy anything:

  1. Is this an item that I know to be useful or believe to be beautiful?
  2. Will buying this item make my life better or worse in the long run?
  3. What is the opportunity cost of using that money instead of buying more VTSAX (my investment vehicle of choice)?
  4. What are the externalities of that item?
  5. What are the environmental implications for the production and distribution of this product?
  6. What were the conditions for the person making this item?
  7. What will happen to that item once it is no longer useful or beautiful?
  8. Does buying this item help someone else greatly? (Externalities can be positive too)

I’m so glad the financial independence/retire early movement is very much anti-consumerism. Don’t buy stuff you don’t need to impress people you don’t like. By asking myself these questions, especially the part about the environment, I find I don’t need most of the things that tempt me and as a result, I own very little. Of course I could always do better. I take a lot of trips.

8. I loved your post about the contrast between working as a database representative in law school and as a waitress. You seem to have learned a lot from that experience. Are there other kinds of work experiences you’d like to have in the future? What do you want to learn from them?

I’d like to work in a factory one day. I think it’s one of the hardest jobs out there and I’d like to see if I could hack it for a little bit. I’d like to start a non-profit one day. Giving back is important and not something I do enough. Heck, I think working in a dispensary for a bit would be fun. It’s probably just like working retail though.

When the pandemic hit, I got a little antsy and applied to a handful of non-profits. I had some interviews and even a job offer which I eventually turned down. If I were to want to revive my legal career, it wouldn’t be an insurmountable task: a couple thousand dollars and a few hundred hours of CLEs.

9. What advice would you give to a law student headed to Biglaw who wants to become financially independent?

Retail therapy won’t make you feel better in the long run. Remember you are trading your LIFE for this money, so they are getting you at a steal. Make the most out of your time there and don’t shackle yourself with golden handcuffs. You never know how long that job is going to last. Every paycheck is a tremendous opportunity to buy freedom.

10.  Finally, you write on your blog about loving books. How do you choose what to read? Any book suggestions—in addition to yours, obviously—that you’d like to pass along to our readers?

I keep a giant list of book recommendations that I receive from other people. It’s already more than I could ever hope to read in my lifetime. Every week or so, I go through the list and pick out two or three books to check out from the library. I usually give a book at least 99 pages before deciding to finish it or not. It’s just enough to give it a proper shot to capture your attention without giving your life to the book.

I read Your Money or Your Life by Vicki Robin and Joe Dominguez when I was a teenager and it made me put early retirement on my life bucket list. It gives you a concrete way to see when you’re financially independent and you’ll be able to retire using numbers, formulas, and charts.

For investing, I recommend:

  • A Random Walk Down Wall Street by Burton G. Malkiel
  • The Bogleheads Guide to Investing by Taylor Larimore, Mel Lindauer, Michael LeBoeuf and John C. Bogle
  • The Simple Path to Wealth by JL Collins

For life, I recommend:

  • On Writing by Stephen King
  • How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life by Scott Adams
  • The 5 Love Languages Military Edition: The Secret to Love That Lasts by Gary Chapman
  • Year of Yes: How to Dance It Out, Stand In the Sun and Be Your Own Person by Shonda Rhimes
  • The Shallows: What the Internet Is Doing to Our Brains by Nicholas Carr
  • Grit: The Power of Passion and Perseverance by Angela Duckworth
  • The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life by Mark Manson
  • A Guide to the Good Life: The Ancient Art of Stoic Joy by William B. Irvine
  • The Power of Now by Eckhart Tolle
  • The Life Changing Magic of Tidying Up by Marie Kondo
  • Modern Romance by Aziz Ansari and Eric Klinenberg
  • Tiny Beautiful Things: Advice on Love and Life from Dear Sugar by Cheryl Strayed

Connect with Anita at The Power of Thrift.

Originally posted on An Interview with a 30-Something Retired Lawyer

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