Tag: personal finance for lawyers

Backdoor Roth IRA: What Lawyers Need to Know

If you’re a lawyer reading a personal finance blog, I’m going to assume that you are already maxing out your 401(k).

That’s a good start.

But, if you’re interested in financial independence, you need to be doing more.

For high earners who read personal finance blogs, maxing out a 401(k) plan is just the beginning.

On top of maxing out a 401(k) plan, I recommend lawyers also max out an HSA.

Maxing out a 401(k) and HSA is a powerful combination.

But, you can still do more.

The reality is there are only so many tax-advantaged investment account types that you can contribute to. It’s important to take advantage of these accounts whenever possible.

So, once you’ve maxed out both your 401(k) and HSA, the next step is to consider maxing out a Roth IRA.

When you can fully fund each of these three accounts, you’re well on your way to financial independence.

Now before you tune out because you don’t make enough money to contribute to all three accounts, hear me out.

If you follow a traditional career trajectory for a lawyer, you will earn more money in the future.

When you do, you want to know what to do with that additional cash so it doesn’t go to waste, like contributing to a Roth IRA.

The thing is, there’s a catch that all lawyers need to know about when it comes to earning a good income and benefiting from Roth IRAs.

That’s what we’re going to explore today.

There’s a catch when it comes to high earners funding a Roth IRA.

When it comes to contributing to a Roth IRA, there’s a catch that high earners need to be aware of.

Because of the amazing tax advantages, there are income limits associated with who may contribute to a Roth IRA. More on these limits below.

My assumption is that if you earn enough money to max out a 401(k) and HSA, and still have funds available for a Roth IRA, you likely exceed these income limits.

Today, we’ll talk about the common strategy that high earners use to get around these income limits. The strategy is known as a “Backdoor Roth IRA conversion.”

With many lawyers earning raises and bonuses towards year-end, this is the perfect time to consider a Backdoor Roth conversion.

The last thing you want to happen is for that extra, hard-earned money to go to waste.

Plus, if you prioritized other financial goals earlier in the year, it’s not too late to circle back to your retirement planning goals, like maxing out a Roth IRA.

Before we talk about the Backdoor Roth IRA, let’s take a look at why you should consider investing in a Roth IRA in the first place.

A Roth IRA provides double tax benefits.

A Roth IRA is a type of retirement account that provides double tax benefits.

The first major tax benefit is that you don’t have to pay any taxes when you withdraw from a Roth IRA (after age 59 1/2). This is the most notable advantage of investing in a Roth IRA.

The second major tax benefit of investing in a Roth IRA is that, just like a 401(k), your earnings grow tax-free. That means more investment growth through the magic of compound interest.

The combination of tax-free withdrawals and tax-free growth means double tax benefits. This is why so many savvy investors, who can afford to do so, choose to max out their Roth IRA.

Photo by Adrian Handschu on Unsplash

The key difference from a 401(k) or traditional IRA is that you make after-tax contributions to a Roth IRA.

With a Roth IRA, you make after-tax contributions. That means you don’t get any immediate tax breaks, unlike when you contribute to a 401(k).

Even so, the two major tax benefits we just discussed make it extremely valuable to contribute to a Roth IRA.

What does it mean to make after-tax contributions to a Roth IRA?

Typically, a lawyer paid as a W-2 employee will fund a Roth IRA with money that gets deposited into his checking account from his paycheck.

That means he already paid taxes on that income through withholdings on his paycheck. So, the money that gets deposited into his checking account is considered “after-tax” money.

Once that money hits his checking account, he gets to decide what to do with it.

The basic decision is pretty simple: he can spend the money or he can save it.

If he chooses to save the money, investing in a Roth IRA is one of the best ways to do it.

Why lawyers should open a Roth IRA besides the double tax benefits.

For a number of reasons, it’s a good idea for every lawyer to consider funding a Roth IRA in addition to his 401(k).

For starters, there are contribution limits to funding employer-sponsored retirement accounts, like a 401(k).

Essentially, you may need more money in retirement than just what your 401(k) plan will provide. Investing in a Roth IRA at the same time is a way to boost your retirement income.

For another reason, 401(k) plans and Roth IRAs are treated differently from a tax perspective, as we just discussed.

Many retirees like having a Roth IRA in addition to their 401(k) so they have access to some tax-free money in retirement.

Include me in this camp. I agree that it is beneficial to have some tax-free income in retirement from a Roth IRA to go along with your taxable income from a 401(k).

Finally, Roth IRAs also provide better flexibility for when you have to withdraw your money and how you can pass your funds onto your heirs.

For example, you can withdraw your Roth IRA contributions tax-free and penalty-free at any time. This flexibility is a huge advantage of a Roth IRA.

Note: There are penalties if you make withdrawals from your earnings before the age of 59 1/2.

For another example, unlike traditional IRAs, Roth IRAs don’t have required minimum distributions (RMDs).

Add all these benefits together and you’ll see why so many lawyers choose to fund a Roth IRA.

Roth IRA contribution and income limits.

As with other tax-advantaged retirement accounts, like a 401(k), there are annual contribution limits for Roth IRAs.

Recently, the IRS raised the 2026 annual contribution limits for Roth IRAs to $7,500, up from $7,000 in 2025. The IRA “catch-up” contribution limit also increased to $1,100 in 2026.

Pertinent for today’s conversation, there are also income limits for contributing to a Roth IRA.

As explained by the IRS:

The income phase-out range for taxpayers making contributions to a Roth IRA is increased to between $153,000 and $168,000 for singles and heads of household, up from between $150,000 and $165,000 for 2025.

For married couples filing jointly, the income phase-out range is increased to between $242,000 and $252,000, up from between $236,000 and $246,000 for 2025. The phase-out range for a married individual filing a separate return who makes contributions to a Roth IRA is not subject to an annual cost-of-living adjustment and remains between $0 and $10,000.

As a lawyer, there’s a good chance you exceed these income limits. If you’re not there already, you soon will if you follow a typical career trajectory.

That’s where the Backdoor Roth IRA strategy comes into play.

Photo by Kaitlan Balsam on Unsplash

What is a Backdoor Roth IRA?

“Backdoor Roth IRA” describes a strategy used by lawyers and other high-income earners who can’t contribute to a Roth IRA because their income is too high.

Because high-income earners are not permitted to contribute directly to a Roth IRA, this strategy involves contributing to a traditional IRA and then converting it to a Roth.

Even though the name implies you’re doing something sneaky, Backdoor Roth IRA conversions are completely permissible.

In fact, every major financial institution, like Vanguard, Fidelity, and Charles Schwab, has a step-by-step guide on how to perform a Backdoor Roth conversion on its website.

The Back Door IRA process involves two steps.

Step 1: Make a nondeductible contribution to a traditional IRA. That means you don’t get an upfront tax break.

Step 2: Convert that contribution to a Roth IRA.

That’s all there is to it. You can perform the conversion yourself through your investment platform. I personally use Vanguard.

Notably, there are no income limits for converting a traditional IRA to a Roth IRA.

And, since the initial contribution is made with after-tax dollars, when executed properly, you shouldn’t owe additional taxes on the conversion.

This process is easier than it sounds. Just be sure to precisely follow the step-by-step guides offered by the financial institution that you invest with.

Finally, as always, be sure to check with your tax advisor or financial advisor before performing a Backdoor Roth conversion.

Do you take advantage of a Backdoor Roth IRA?

Maxing out your 401(k) is a good start.

Maxing out your 401(k) and HSA is even better.

If you also max out your Roth IRA, whether directly or through a Backdoor Roth conversion, that’s next level.

As a lawyer earning a high income, there’s really no excuse for not maxing out each of these three accounts.

If you make good money and are falling short, you should revisit your budget. You also should spend some time thinking about what financial independence might mean for you and your family.

The end of the year and the holiday season are great times to think and make adjustments to move you closer to financial freedom.

What do you think of the Backdoor Roth?

Have you contributed through the backdoor in the past?

Planning to contribute again this year?

Let us know in the comments below.

November 24, 2025
Why It’s So Important to Learn Personal Finance
When I graduated law school in 2009, I never thought about money.

Within a year, I had racked up $20,000 in credit card debt ($30,000 in today’s dollars).

And, that was on top of my student loan debt.

My salary at the time was $62,000. This was a problem.

After all these years, I still ask myself, “How did I let that happen?”

The answer, I now realize, is actually pretty simple.

I never learned about personal finance.

I wasn’t thinking about money. And, I certainly wasn’t talking about money.

It wasn’t until later that I learned that I had made every common money mistake in the book.
- Rented a fancy apartment with a garage parking spot that I didn’t need?
- Paid for Cubs season tickets I couldn’t afford?
- Traveled coast-to-coast? Traveled overseas? Put it all on credit cards?
Check… check.. and check.

It’s not that I intentionally decided to get into debt. Frankly, there was nothing unusual about me at all.

I generally wanted to make good choices. I am a relatively smart human. You are, too. You’re reading a personal finance blog with the entire internet at your fingertips.

Maybe you’re like me, and it hadn’t occurred to you that money was a thing you needed to learn about.

I didn’t know the first thing about money when I began my career.

When I graduate law school, I blindly assumed that I would earn a high enough income that I didn’t have to worry about money.

As I fell deeper and deeper into debt, I realized what a huge mistake that was.

Maybe that’s why I still remember the day so clearly when I realized I was financially heading in the wrong direction.

It was an ordinary Monday. I had grabbed my mail on the way out the door as I headed to my job at the courthouse. When I got to my desk, I opened my credit card statement and was stunned by what I saw.

$20,000 owed ($30,000 in today’s dollars) one year into my career.

I was ashamed. I was supposed to be smart. Responsible. Trustworthy.

How could I be so foolish?

Looking back, I shouldn’t have been so hard on myself. I had never learned about personal finances.

It would be like getting upset today that I’m bad at playing the piano when I never learned how to play in the first place.

I’m certain that if I taken a personal finance course, or read a personal finance blog, I wouldn’t have made the same mistakes.

I would have saved myself a lot of worry, frustration, and time if I had a basic personal finance education.

I also would have learned that so many others were struggling with consumer debt like I was. There was no reason to make it harder on myself by keeping my debt a secret and struggling alone.

I unnecessarily did it the hard way, but I figured out personal finance.

At that moment when the full weight of my debt hit me, I made it a priority to turn things around.

At the time, I didn’t know the solution.

But, I had been trained to do research in law school so I could find answers to hard questions. So, that’s what I did.

Along the way, I realized that the fundamental and basic personal finance principles are, well, basic.

George S. Clason wrote “The Richest Man in Babylon” nearly a century ago. His collection of parables set in ancient Babylon is legendary.

Everyone should read it. His advice is simple and excellent: spend less than you earn. Save. Invest.

The same fundamentals are as true today as they were then.

Easy, right?

Not exactly.

Photo by Unseen Studio on Unsplash

Personal finance education should be a constant in your life.

Money is about continuous mindset and choices.

The basic concepts are easy enough to understand. Consistently making good choices is hard.

Even as I was racking up credit card debt, I could have aced a quiz that asked, “Is it a good idea to spend more money than you earn every month and plummet deeper and deeper into debt?”

I knew that I was supposed to spend less than I earned. That didn’t stop me from overspending.

Knowing the right answer is not the same as actually doing the right thing.

The law students and lawyers I teach are smart people. Like me back in 2010, they generally know the right answers. They don’t need me to tell them to spend less than they earn.

I help them get to the next level by building a strong money mindset. Then, we work on the habits and skills that will allow them to consistently use money as a tool to control their circumstances.

It’s not enough to learn the basics of personal finance and then stop. As your life changes, you need to regularly evaluate your personal finances so your money stays in line with your values.

That’s why it’s important to make personal finance education a constant in your life, whether it’s through a blog, a course or coaching.

Too many of us choose to struggle with money alone.

For some reason, though, most of us choose to deal with money on our own. Alone, we struggle with anxiety about credit card debt and guilt about splurging on things we love.

This has never made sense to me.

Making good choices with our money is essential to a healthy and meaningful life.

Why don’t we talk more about these things with our friends and family?

That’s what I’m trying to change.

I’m done with this stigma that we shouldn’t talk about money.

I want us to get comfortable with the idea of going to our friends and loved ones to talk about money, just as we would talk about anything else.

There should be no embarrassment or shame in it. We’re all dealing with the same challenges.

By talking about money, we can help each other turn those challenges into opportunities.

If we can alleviate our money stress, perhaps we can reverse the trend of lower happiness levels among young people today.

Talking about money is not about numbers.

We’ll have plenty more to say about how to talk money. For now, let’s agree that talking about money is not about prying into how many dollars we each have in the bank.

We can benefit by talking about our money mindset, habits, and strategies, while still keeping certain information private.

Let’s also agree that talking money is a “no judgment” endeavor.

We have all had different experiences that have shaped our relationship with money.

It’s important not to pass judgment, especially when talking to our significant others. Your conversation won’t last very long if you ignore this advice.

Each session I’m with my students, I learn from their experiences and money mindset, same as they learn from mine. I encourage them to continue the conversation outside the classroom with their loves ones.

When my students report back, they tell me how empowered they felt after starting these conversations. The more we can talk money, the less we’ll feel alone. We’ll all make better choices because of it.

Photo by Lesly Juarez on Unsplash

Talk about money mindset with your significant other, family, and friends.

If you want to know where to begin the conversation with your loved ones, start with money mindset.

Money mindset touches every aspect of personal finance, so it’s the natural place to start.

I didn’t realize the power of money mindset until I wrote down my Tiara Goals for financial independence on a beach in 2017.

People tend to skip this step. They want to jump straight to investing and real estate before learning about money mindset.

But, why focus on investing if you and your significant other are not aligned on what those investments are for?

The same logic applies to budgeting. While very few people enjoy the budgeting process, it’s a crucial step to generate fuel for our savings and investments, which ultimately fund our major life goals.

The progression matters. Only after we’ve learned about budgeting, saving, and how to responsibly use debt and credit cards should we focus on investing and real estate investing.

Talking about money is not taboo.

There’s no reason to embark on your journey to financial freedom alone.

Read a personal finance blog. Take a personal finance course.

Talk about money.

Share your accomplishments and struggles with your friends and loved ones. You’ll only be better off for it.

If I can be of any help on your journey, please don’t hesitate to reach out.

Don’t forget to subscribe to my email list for all the latest money topics I’m thinking about.
October 31, 2025
Stop Feeling Guilty and Annoyed About Spending Money
No matter how far along you are on your personal finance journey, you will always need to make choices on how to spend your money.

I recently wrote about how I felt annoyed when I wanted to buy a new bike and new golf clubs.

You have to make decisions like this whether you make a lot of money or very little money.

The more money you make, the harder these choices can be. When I was in my 20s, traveling and a social life were my biggest spending challenges.

Now that I’m in my 40s, it’s making good spending choices for not only me, but my wife and three kids.

The other day, I confessed that I was annoyed because my goal to pay off debt was keeping me from buying a new bike or new golf clubs.

What I’ve realized since then is that I also felt guilty about spending money on myself when I could better spend that money on my kids.

I felt guilty because my five-year-old wants to learn how to ride a bike. I should buy her a bike and teach her to ride before I splurge on a new bike for myself, right?

With powerful feelings like annoyance and guilt, how can we make good spending decisions even as we make more money?

Don’t ignore key personal finance fundamentals even as you start to make more money.

What I’ve learned as my career and family obligations evolve is that it’s easy to forget the little things I used to focus on when money was tight.

This recent experience reminded me that I need to step back and focus on personal finance basics.

I’m not alone in needing a reminder from time to time about personal finance fundamentals, like budgeting. I talk to plenty of people who tell me that they kept a budget in their 20s but not so much in their 30s and 40s.

They share with me that even though they’re making more money, it seems like they have less and less money to spend.

I totally get it because I was the same way. I tracked every penny I made in my 20s until I learned how to stay on budget with two simple numbers. Recently, I haven’t been as diligent.

My recent dilemma with the new bike and golf clubs reminded me to go back to the fundamentals.

The benefit is that by remembering the basics, I can help myself by taking the anxiety and guilt out of these types of spending choices.

So, what are the fundamentals I’m referring to?

After I wrote that post about the new bike and golf clubs, I reviewed my top 10 budgeting tips for lawyers and professionals.

My Top 10 Budgeting Tips for Lawyers and Professionals
1. See the ball go through the hoop.
2. Don’t cancel your social life.
3. Talk to your friends about your life money.
4. Keep on traveling.
5. Spark and cut.
6. It’s OK if you occasionally exceed your spending.
7. Make a game out of it, like the $500 challenge.
8. Buy it if you want it, but not right away.
9. You don’t have to go big or go home.
10. Plan ahead for budget busters.
Photo by Heidi Fin on Unsplash

These budgeting strategies helped me realize that I can choose to spend money on what I want and shouldn’t feel guilty or annoyed.

The key is understanding how a certain purchase fits into the rest of my overall spending.

On this occasion, 3 of my top 10 budgeting tips stood out and helped me with what to do about the new bike and golf clubs.

Let’s take a look.

6. It’s OK if you occasionally exceed your spending.

What should you do if you overspend one month? Don’t get discouraged and give up. Before all your hard work goes to waste, take the next month to course correct.

If you overspent by $300 in August, make it a priority to underspend by $300 in September.

Is this easier said than done?

Well, sure. It’s always easier to say you’re going to do something. The hard part is following through. It will take discipline to get back on track. What will drive that discipline?

Once again, it’s your ultimate life motivations that we’ve talked so much about (and will always continue to talk about). Without that clear vision of your ideal life in front of you, no budget will ever last.

Don’t panic. Course correct. Stay on track.

Even though I didn’t buy the new bike or golf clubs, if I chose to do so, I could course correct the next month.

Going over budget for just one month is fixable. The key is to not blow my budget multiple months in a row.

If I did that, I would end up digging a hole so deep that it would be a major challenge to get back to good spending levels.

8. Buy it if you want it, but not right away.

Just because I didn’t buy the bike or golf clubs yet doesn’t mean I can’t buy them in the future when the time is right.

I always think of my mom when I see something that I want to buy but know I shouldn’t buy it right away.

About 10 years ago, my mom bought me a jacket for a birthday present. It was the exact jacket I wanted. How did she know, I asked her. “You mentioned it when we were downtown four months ago.” Four months ago!

I shouldn’t have been surprised. My mom has one of those steel trap memories.

If you only met her for five minutes and then saw her again two years later, don’t be surprised when she asks about your consulting gig, your trip to New Orleans, and that blue dress that she really liked.

I learned from my mom’s gift strategy and modified it to help myself resist the temptation to make impromptu purchases. I don’t have her memory, but I do have a phone with a notes function.

When I see something that I might want to buy, I do my best to resist the temptation of buying it immediately and make a note in my phone. After a couple weeks, if I still want that thing, I buy it.

More times than not, I no longer want whatever it was that tempted me in the moment.

If I still want the bike or golf clubs a few weeks from now, I can still buy them. By waiting, I also might benefit from end-of-the-season sales and can shop around for the best offers.

10. Plan ahead for budget busters.

Budget busters are any inconsistent expenditures, good or bad, that can derail your planning.

Good budget busters might include trips, weddings, and holiday/birthday gift shopping.

We can also add a new bike and golf clubs to the good budget busters category. These certainly count as irregular expenses but can wreck our budgets if we don’t properly plan for them.

Bad budget busters include unexpected car repairs, home repairs, or medical expenses.

Note, budget busters are inconsistent; they are not unexpected. These expenditures are 100% predictable every year, we just don’t always know when they will surface.

Photo by Alexander Grey on Unsplash

Planning ahead for budget busters is crucial to staying on track.

To do so, open up a savings account, preferably at a different bank than your checking account. This helps isolate those funds so those dollars don’t disappear.

As part of our really lost boy’s Budget After Thinking, you’ll recall that we had a separate line item for budget busters in both our Now Money (bad budget busters) and Life Money (good budget busters).

I encourage you to do the same. Each month that you don’t spend your budget buster money, transfer it to your savings account so it’s there when you need it.

One more bonus tip for dealing with budget busters.

We talked above about how to course correct when you exceed your budget in one month. On the flip side, what should you do when you’ve had a great month and underspent?

I recommend you transfer the amount you underspent to your budget busters savings account. Don’t let that hard-earned money sit in your checking account.

Those dollars will disappear. By transferring them to savings, those dollars will be at your disposal when needed.

Instead of buying the bike or golf clubs now, I can transfer some funds in my savings account and wait to go shopping until I have enough saved up.

Don’t ignore your budget even if you’re far along on your personal finance journey.

My experience with the new bike and golf clubs served as a great reminder to revisit personal finance fundamentals, like budgeting.

If you haven’t thought about your spending choices in a while, now is a good time to do it.

The 10 budgeting strategies mentioned above have worked for me in the past and continue to work for me today.

If you review those top 10 strategies, I hope you see that making good spending choices does not have to make us feel annoyed or guilty.

It just takes a little mental energy, exerted ahead of time.

When making good spending choices becomes part of your everyday life, you can eliminate the guilt and anxiety that comes with tough choices, like buying a new bike or golf clubs.

Have you been in a similar situation where you wanted to buy something but were worried about how it fit into your overall budget?

What did you decide to do?

Let us know in the comments below.
August 12, 2025
Student Loans and Financial Freedom
Debt from student loans and financial freedom go hand-in-hand for most professionals. Maybe a better way to put it is that student loans can be a major obstacle on your path to financial freedom.

Student loans and financial freedom go hand-in-hand.

Whether you have student loan debt from college or graduate school, it’s important to have a plan to pay that debt off.

All debt acts as a roadblock to financial freedom. Student loans are no different.

Of course, the more education you’ve received, the more student loans you likely have.

When considering student loans and financial freedom, look no further than these recent stats provided by the Education Data Initiative:
- The average person with a graduate degree owes up to $102,790 in federal student loan debt.
- 54.0% of all graduate school students have federal student loan debt.
- 55.2% of people with master’s degrees have federal student loan debt.
- 74.8% of people with professional doctorates have federal student loan debt.
- 76.2% of doctors have student loan debt.
This is why it’s especially important for professionals to realize the connection between student loans and financial freedom.

Hold on before you tune out because you don’t have any student loan debt.

The journey towards financial freedom is often a shared journey for many of us.

This data shows that even if you don’t personally have any student loan debt, the odds are you are going to marry someone who does. Or, you’re the parent, or will someday be the parent, of someone who has student loans.

That’s why we all need to learn about student loans and financial freedom. You may soon find yourself in a relationship where you’ll want these student loan strategies.

If nothing else, your prior experiences with student loans can help someone else if you’re just willing to talk about them.

I’ll never forget the day I made my last student loan payment.

My family was heading out to Colorado around Christmas time for some snowboarding and skiing. Don’t worry, I didn’t break a wrist that trip.

My goal that year had been to finish paying off my student loans entirely. However, I can’t take credit for wanting to pay off my loans that year.

That credit goes to my wife. She was the first person who helped me appreciate the interconnection between student loans and financial freedom.

Here’s what happened.

About 11-12 months before that trip to Colorado, my (future) wife and I talked about how we wanted to start our marriage debt-free. We were thinking about buying a home and starting a family. Student loan debt did not fit into this picture.

She was the one who initiated the conversation.

She knew long before I did that talking about money is not taboo.

All these years later, I’m still so grateful that she didn’t shy away from having that important conversation.

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Why I wanted to pay off my student loans before I got married.

M wife and I met in the days where I was just starting to tackle my credit card debt after law school. She knew how heavy that debt felt for me.

She saw how focused I was in creating a Budget After Thinking and how important it was for me to stick with it.

My wife also experienced firsthand how much better I felt once I had a plan to pay off my debt. She wasn’t just an observer, either. She was an active participant.

Whether it was budgeting games like the $500 challenge or sharing a hotel room with my friends for a wedding, she was part of my journey.

So, when I had finally paid off all of my credit card debt, it was time to focus all that financial energy on my student loan debt.

This may sound odd, but I was excited to move on to a new challenge. Not that paying off debt is ever easy. But, with my student loans, I knew it was going to be easier than paying off my credit card debt.

That’s because I had already learned and experienced the hardest part of paying off debt with my credit card experience. I had already shifted my money mindset.

By this point, I wanted to be good with money. Not only for myself, but for my future family.

Money mindset is so important to student loans and financial freedom.

Once your money mindset is in the right place, you can make informed and intentional choices about debt. It doesn’t matter if you’re paying off credit cards, student loans, or even HELOC debt.

When you’re honest and dedicated to fostering a healthy money mindset, you’re better able to establish habits like budgeting and saving. That’s how you create fuel for your Later Money goals, like eliminating debt.

Personally, my money mindset was in a much different place by the time I prioritized paying off student loan debt compared to paying off credit card debt.

With my credit card debt, it took waking up one day and feeling ashamed for how irresponsible I was with my spending before I committed to paying it off. I felt down and discouraged.

On the bright side, those negative feelings are what set me on the path to learn and eventually teach personal finance.

With my student loans, I wasn’t starting from a feeling of failure. It was quite the opposite, actually. I had a much better attitude because I had proven to myself that I could pay off debt. I had experienced how good that felt.

So, when my wife and I talked about eliminating my student loan debt before we got married, that was just one final incentive.

My wife would say that I’m a quietly competitive person. When she initiated that talk about paying off my student loans before we got married, it was game on for me.

I didn’t need any extra motivation, but I sure felt extra motivated after that talk.

I prioritized paying off my student loans the rest of that year.

For the next 11-12 months, I made it my priority to eliminate my student loan debt. I had been making the required payments each month for years, but eliminating my student loans always took a back seat to my other goals. Now, it was time to prioritize eliminating my student loans.

Using the Debt Snowball method, I used whatever excess money I had each month to pay off the remaining balance on one loan at a time.

This was before we owned any real estate, but I had begun my side hustle as a law school professor. Whenever I got a paycheck from the law school, I immediately put it towards my student loans.

When I earned a raise that year, I put the whole raise towards my student loans. I did the same thing with irregular earnings, like from commissions, bonuses and even my tax refund.

“Snow Mountain” by Jeff Hollett/ CC0 1.0

As our Colorado trip was approaching, I knew that the finish line was in sight. I waited to tell my future wife just how close I was until after I had made the final payment. I’ve always liked surprising her.

I remember telling her I just made the last payment on the day before we left for the trip. She was thrilled, and surprised, at how quickly I accomplished the goal.

I thanked her for motivating me.

The next day in Colorado, I shared the news with my parents that I had pay off my student loans. They were even happier than my wife and I were. All my siblings were there with us. We had a toast and celebrated. It was a night I’ll never forget.

It’s natural to worry about paying back student loan debt.

When I teach personal finance for lawyers, student loan debt is always one of the most important topics. It’s natural to worry about paying back such a large sum of money as you are beginning your career.

Even if I didn’t realize before, I now fully appreciate the relationship between student loans and financial freedom.

My hope is that by thinking and talking even a little bit about your student loans, you won’t have to worry. You’ll have a plan to pay back your loans in the most efficient way possible on your way to financial freedom.

In our initial series on student loans, we’ll learn how to:
- Find your loan balance, set up payments, and other important basics when you’re just getting started.
- Choose a repayment plan that works best for your personal situation.
- Strategize to pay off student loan debt within the context of your overall life goals.
- Navigate the ever-changing landscape of student loans.
Then, you’ll have your own reason to celebrate with your loved ones just like I did in Colorado.

Have you thought about student loans and financial freedom?

Where are you currently with your student loans? Just starting out, nearing completion, or somewhere in the middle?

Are you the partner or parent of someone with student loans? Have you discussed a plan for paying those loans off?

Let us know so we can learn from each other’s experiences in the comments below.
March 31, 2025
Why Personal Finance for Lawyers is so Important
I founded Think and Talk Money after years of teaching personal finance for lawyers and law students.

My purpose is to share these principles of personal finance for lawyers with all professionals striving for financial freedom.

I like to think and talk about money. To help us achieve financial freedom, we can’t be embarrassed or afraid to talk about money with our friends and family.

That’s why I’m on a mission to convince people that talking money is not taboo.

I like thinking and talking about life and money.

“If you want to get Matt talking, bring up life and money.”

My wife knows me better than anyone.

I like thinking and talking about life and money. That’s why I started teaching financial wellness to law students in 2021 and started this blog in 2024.

But, I wasn’t always like that.

When I graduated law school in 2009, I never thought about money. Within a year, I had racked up $20,000 in credit card debt ($30,000 in today’s dollars), on top of my student loan debt.

My salary at the time was $62,000. This was a problem.

How did that happen?

Well, I wasn’t thinking about money. I certainly wasn’t talking about money.

Of course, I later learned that I had made every money mistake in the book.

Rented a fancy apartment I didn’t need?

Paid for Cubs season tickets I couldn’t afford?

Traveled coast-to-coast? Traveled overseas? Put it all on credit cards?

Check… check.. and check.

It’s not that I intentionally decided to get into debt. I generally wanted to make good choices. I am a relatively smart human. You are, too. You’re reading a blog about financial wellness with the entire internet at your fingertips.

Maybe you’re like me, and it hadn’t occurred to you that money was a thing you needed to think about. And to talk about. Preferably with people impacted by your money choices.

I dedicated myself to learning about money.

Since 2010, I’ve dedicated myself to learning about money and its role in crafting a healthy life.

First, I read all the personal finance books and listened to podcasts.

Along the way, I kept a money journal. Plus, I talked to people I trusted.

In the end, I started to make choices with my money that matched my values.

Years into my own money journey, and now teaching personal finance for lawyers and professionals, here are a few things to know about me:

I work for clients with mesothelioma, a cancer caused by asbestos.

Since 2011, I’ve represented hundreds of people suffering from mesothelioma, a rare cancer caused by asbestos.

Most of my clients are in their seventies and eighties. A significant part of my job since I’ve been in my twenties has been meeting with individuals in their homes after they had just found out they have incurable cancer.

Before we ever get around to talking about the case, we inevitably end up talking about life.

I do most of the listening. You can imagine what I’ve learned about life in these moments. Many of my core money beliefs have been shaped by these powerful experiences.

I am a real estate investor and own rental properties in Chicago and Colorado.

In 2018, my wife and I bought our first rental property in Chicago, a 4-flat in an up-and-coming neighborhood. We lived in one unit and rented out the other three.

I’ll never forget riding my bike with my wife and a buddy, heading from the fancy part of the city where I had been living to my new home. I could tell my buddy was skeptical about my new neighborhood.

Finally, he saw something he recognized and said, “Hey, nice! A spin studio!” He saw a sign that read “Cycle Spin.”

It was a laundromat.

He wasn’t the only one who was probably thinking, “what is Matt doing?”

Well, that 4-flat allowed my wife and I (and eventually two kids) to live for free for six years.

See, the rent we collected covered our mortgage, insurance, taxes, maintenance, and then some.

With the money we saved, we bought our second rental property in 2019, a nearby 3-flat.

In 2022, we purchased another Chicago 3-flat, where my family lived for about two years before moving to our permanent home.

My tenants are doctors, lawyers, engineers, TV personalities, pilots, and other young professionals.

In 2021, we bought a rental condo in Colorado ski country. This had been a dream of mine hatched at The 1800 Club in Evanston during college.

Back then, I amused my friends on many a ski trip by cartwheeling down the mountain as I learned to snowboard.

To pay for flights and lift tickets, I took a couple part-time jobs in local offices. I told myself one day I would “Get that Mountain.”

While my wife and I were contemplating life during the height of the pandemic, we determined that a ski condo fit perfectly with our desire to be with family, to be active, and to be outdoors as much as possible.

So, we delayed buying our “forever home” for another investment property, this time one in Colorado that we could rent out and use a little bit ourselves.

I started a money journal in 2010.

I started a money journal in 2010. It has been a lot of fun to look at as I launched my financial wellness course and as I’m writing this blog.

I’ll refer back to these entries as I share my lessons about personal finance for lawyers and professionals.

Some entries are just scribbles while I worked through that month’s money question.

Some entries go deep.

My favorite: I wrote in 2011 that someday I was going to marry the girl I had been dating at that time for the past few months.

That girl became my wife in 2017.

I encourage everyone to keep some sort of money journal. It doesn’t have to be a daily log or a detailed memoir. Use to help you think. It will also reinforce the idea that we all need to think about money continuously.

Some of the same challenges I had in my 20’s, are resurfacing today, like paying off debt. Then, it was student loans. Now, it’s mortgages.

I am more confident today because I can look back at how I handled those obstacles back then.

I have taught personal finance for lawyers since 2021.

Since 2011, I’ve taught law students how to research, write, and communicate in the courtroom. We work on finding answers to difficult questions.

Oftentimes, there are many possible answers, and we have to think and analyze which is the best for our situation.

I regularly have coffee with students who want to talk about what comes next after finishing school. I learned that, just like me in 2009, my students didn’t typically think or talk about money and life. They never really thought about learning personal finance for lawyers.

I wanted to help them avoid the money struggles that I had experienced at the beginning of my career.

That’s why in 2021, I designed and launched a course focused on personal finance for lawyers.

My goal with that course, and this website, is to help us all think about using money as a tool to build a life that conforms to our personal values.

The point is not to get rich. Though, you will if that’s your goal and you follow along. The point is to live your life on purpose where you actively think and choose what happens next.

Think about why money matters.

The first step is to think about a simple and powerful question:

Why does money matter?

For me and many others, money is about financial independence, which translates to the power to choose. When we have the power to choose, we have the power to live a life that conforms to our personal values.

That means we can live on purpose, not on auto-pilot.

We can choose to spend our working hours doing what is meaningful to us.

We can choose to spend more time with the people that are meaningful to us.

And it all starts with using money as a tool to do what we want with our lives.

My favorite part during my personal finance for lawyers class is when my students share their motivations with each other. We all learn so much from these honest conversations.

It’s why I believe talking about money is so important. We all benefit from knowing that we’re not alone in our money worries. It is inspiring to hear what our friends want from their money and their lives.

If nothing else, I want you to think and talk about money.

As a lawyer, I’ve been trained to build upon the work of those who have come before us.

Think and Talk Money is my contribution to this essential field of personal finance, building upon what I was so grateful to learn. Not just from authors, but from all the people in my life who talk with me about life and money.

In teaching personal finance for lawyers, I’ve learned that most of us are facing the same challenges. Maybe my voice and my experiences will resonate with you. Maybe not. And that’s ok.

I will be honest about the mistakes I’ve made and the lessons I’ve learned. We’ll talk about motivation, habits, and fundamentals. We’ll talk about careers and goals. Of course, we’ll talk about investing in real estate and managing rental properties.

I’ll share my thoughts on key news and developments. I don’t expect you to agree with everything I say. Not every post will be immediately helpful for you. That’s not my goal or even realistic.

Think just a little bit about money every week.

My goal is to help you think even a little bit about your money choices every week.

That way, your money life remains in balance with the rest of your life, and you can continually evolve and adapt your choices as your life changes.

I want to encourage you to think, and to talk, and to choose. If all I do is help you and your loved ones think more purposefully about your money, this website will be a success.

Maybe your goal is also financial independence, or the power to choose. The power to live on purpose.

Maybe it’s something else entirely. Whatever it is, discovering your motivation is the crucial first step.

It’s so important that I’ll encourage you to think about that motivation every day.

I’ve learned that money is something that we all need to think about as a regular part of our lives. Not that we should only think about money. Or that we need to obsess over money. Simply that we can’t ignore money.

How sad is it when we realize our hard earned money has just vanished?

That at the end of each month, we have less money than at the beginning?

You’re not alone. There are a lot of smart people who need somewhere to turn learn about money. Or, maybe just a reminder to actively think about their money.

Most of us could use someone to talk to or something to read to help us learn about personal finance for lawyers and professionals.

I hope Think and Talk Money can be that place for you.

I can’t, and won’t, tell you what to do with your money. It’s your life, after all. But, I will strive to help you think and talk with purpose about your money.

Here we go.
12 responses to “Why Personal Finance for Lawyers is so Important”
1. Bill Molander
  
  December 31, 2024
  
  Well written, Matt! Best wishes to you in future endeavors.
  
  Reply
  
  Matthew Adair
  
  January 1, 2025
  
  Thank you, Bill!
  
  Reply
2. Clarke Nobiletti
  
  December 31, 2024
  
  Excited for the valuable advice!
  
  Reply
  
  Matthew Adair
  
  January 1, 2025
  
  Thank you, Clarke!
  
  Reply
3. Laurie
  
  December 31, 2024
  
  Hey, I think your ideas are very interesting. Thanks for your thoughts. Maybe keeping money journal is a good idea for me too. A fresh outlook and clean slate for starting out the new year makes sense too.
  
  Reply
  
  Matthew Adair
  
  January 1, 2025
  
  Great attitude, Laurie! Keep me posted on your money journal!
  
  Reply
4. Jeffrey Tallis
  
  January 1, 2025
  
  Smart young man! He listens to people! He takes what he hears and learns from it! Great stuff here! Your law students are lucky to have you as a money mentor!
  
  Reply
  
  Matthew Adair
  
  January 1, 2025
  
  Thank you, Jeff! Glad you enjoyed the first post!
  
  Reply
5. Diana
  
  January 1, 2025
  
  This was a great read — thanks for sharing!
  
  Reply
  
  Matthew Adair
  
  January 1, 2025
  
  Thank you, Diana!
  
  Reply
6. Nicholas Faklis
  
  January 1, 2025
  
  Matt What are your thoughts on index funds vs individual stocks ?
  
  Reply
  
  Matthew Adair
  
  January 1, 2025
  
  Great question! I invest in index funds and think that’s the best choice for many of us. We’ll have to revisit this topic in a future post. Stay tuned!
  
  Reply
December 31, 2024