18 Regrets Lawyers say “Wish I ___ Differently” Comments You Will Never Say

After serving now for over ten years as one of (only two) British Columbia’s Authorized Advisors for Lawyers Financial, I’ve had the distinct pleasure of helping research, architect, implement, and coach thousands of Lawyers on making financial decisions, be it their personal or Law Corporation affairs.

After having hundreds of meetings and working through a vastly diverse set of situations, I’m confident when I tell you; I’ve seen the good the bad and the ugly.

No matter which characters these Lawyer’s financial situation embodied from the Clint Eastwood 1966 Western cult classic, there is one statement the majority of them I’ve helped resite after I’ve built their plan:

“Wow, if only I had done ________ differently in my earlier years.”

Followed by…

“You know, I knew I was supposed to do this, but for whatever reason, I didn’t.”

Sometimes these statements were related to their financial situation, like how they could have better managed their Practice to yield higher profits. And, other times, it was tied to how inefficient they were with their time, and, in the end, how it cost them more than it made them (professionally and personally).

One thing was true of all statements; they were entirely achievable in the time they should have been. So why didn’t these Lawyers do what they needed to in the time it was most critical?

Well, it’s simple – hindsight is 20/20…

There was something they deemed more important that distracted them, or it just never occurred to them.

So how can you avoid wasted time and ineffective management of your financial and personal goals?


Whether you’re an Articling Student, an Associate, a Partner in a Firm, or are an Attorney at Law – I’ve spoken to someone in the metaphorical shoes you are wearing at this very moment before. Take my years of learning and exposure to your predecessors to fast-track both your professional and personal aspirations and avoid having to recite that dreadful comment “I wish I would have done ____.”

Based on the hundreds of wealth plans that I’ve built for Lawyers just like you, I’ve curated the top 18 “wish I ____ ” comments Lawyers older than 55 shared with me, that, had they done, would have driven the most impact to both their professional and personal lives.

Serviss Wealth Management

1. I wish I truly knew what it meant to lower my expectations.

Finding a work-life balance is something that we all know is important. But until you get a little older and realize there will always be a Lawyer somewhere who can bill more, work more, dedicate more, schmooze more, draft faster, delegate better, dress better…the list goes on – you will never realize it’s a no-win, stress-inducing situation to feel like you need to keep up with that hot-shot David that works at the firm down the street who wears sensationally coloured socks and works out five times a week.

You can still feel a sense of accomplishment when you set and work towards your OWN goals.

Your OWN goals take into account your life, your family, and your interests. Everything else is just a distraction that will hold you back.

When you reduce the amount of time you allocate to competing in the rat race and increase the amount of time you allocate to focusing on your own affairs, you will experience a sense of clarity and focus as you’ve never felt before.

Once you realized this, and treat your time with more respect, you will unlock a level of efficiently that blow those obnoxious socks right off David’s feet.

2. I wish I’ had the courage to live a life true to myself and not the life others expected of me.

“After working two decades for a large national firm where the expectations of other people weighed on me day in and day out, one day the stress got to me, and I was hospitalized for a panic attack.

At that moment, I committed to getting myself healthy and in a good state of mind to then start my firm. I lowered all the expectations that other people (previous managing partners) put on me and established my expectations of the firm and the life I wanted to live.

Although I was not making the same money, I felt like I won the lottery and was able to focus on wealth initiatives in my own family’s life.

Like owning a cottage on a small lake!”

3. I wish I experienced more “life.”

“With so much focus and energy spent from a very young age on schooling, discipline, and being a great advocate for my clients, somewhere along the early years, I missed the part where I needed to reflect and intentionally spend my time and money on life.

Not spending enough time setting goals and giving my mind time to decompress, contemplate, and putting my goals on paper would have been allowed to me see my picture more clearly to make more responsible decisions on behalf of my colleagues and my family.” 

4. I wish I spent more time with my kids.

“After watching my Grandchildren grow in their earlier years, I realized how much of my children’s younger years I missed.

My focus in my younger years was financially providing for my family. I used “providing for the family” as an escape, excuse, and fear of the unknown to base my decisions.

Deep down, I always knew we would be OK, and I should have trusted myself more. I should have taken that odd Tuesday afternoon off, or went in late on a random Wednesday because my kids wanted to ride bikes in the driveway.”

5. I wish I found work-life balance, quicker.

“I wish I discovered this work-life thought leadership sooner.

As a Lawyer I was focused on, the longer hours I worked, the more billable time, the more office time, the more client meetings, the more I thought that I was a greater “success.”

Reflecting back on all the people I was trying to impress in the first place, they aren’t even in my life anymore…how backward was my thinking…and all that stress and sacrifice for what?


6. I wish I practiced self-care to protect my mental health.

“The thought of taking the afternoon off and getting an expensive haircut or a non-injury based massage would have been unheard of when I was in my late 30’s or early 40’s.

There was no time…or so I thought there was no time.

I just didn’t make the time. I didn’t block it on my calendar. If one Friday a month, I blocked out a mountain bike ride in my schedule, would that have affected my revenue or level of client service?

I wish I could have seen the fact it would NOT have affected anything, other than making my “self” batteries more recharged.”

7. I wish that I had let myself be happier.

“Although I was very happy with my success in the courtroom and on the files I contributed to, I always felt something was missing in my life.

If I didn’t see a connection to what I was working on, I found social situations lacking substance and found myself isolating from non-lawyer functions.

After getting a little older and beating cancer, I realized there was a whole world out there I had been missing—a world of connection, emotion, caring, purpose, and satisfaction outside the office.

Although I felt moments of happiness outside the office on occasion, I never really let myself just pause and be grateful for feeling happy. I was always over-analyzing if the time I was allocating outside the office was good for my law career.” 

8. I wish I had spent more time on physical health.

“The habits I have today after working in fast-paced law firms my whole life have finally caught up to me. After having a heart complication at the age of 57, I have had to implement regular movement, walking, bike riding, hiking, stand up paddleboarding, and now seeing the benefits I wish I could rewind the clock.

The social aspect of physical activity is a highlight. The discipline of regularly making time to exercise has shown me the value of making faster decisions, which has influenced my interest in trading stocks (or at least a keen interest that could lead to a retirement hobby).”

9. I wish I permitted myself to be more creative (or even more immature).

“When I was a kid, I explored, I failed at things, I got dirty, I didn’t think twice, I made friends with everyone. I was happy. Over the years in the courtroom, I have become hardened.

I am a great Lawyer, but I have lost touch with who I am as a person. Now rediscovering it at my age takes work, takes effort, and is probably not a reality.

I try to be more “like I used to be,” but it feels awkward, so I default to the courtroom Lawyer I believe I know best how to be. It still bugs me every day, though.”

10. I wish I bought life insurance that lasted longer.

When it came time to my insurance plans, I was always looking for the best price, deal, or thinking in short term increments. As I got older, my insurance rates started getting expensive, so I canceled the policies, and although it was great because I didn’t die, all those previous years’ premiums were gone, and I received nothing back when I canceled.

I also thought my debts would be down, and my savings would be higher than actuality, but even in my early 60’s, I still want to protect my wife with some life insurance in case I died, but the rates are creeping up now, and I’m uncertain if it’s even feasible.”


11. I wish I started planning for retirement sooner.

“Being a busy lawyer has its perks.

I have felt valued, serving a higher purpose, and will continue to focus on the craft of Law.

Life goes by in the blink of an eye, and when I started to think about retirement and all the things I needed financially for this…my retirement savings, real estate ownership, debt’s being down, and overall financial organization…it was too late to get on track because I still needed to accumulate assets/investments to live the life I wanted.

I did not have time on my side.

My actual retirement life was much different than what I envisioned when I was in my early 40’s, plus I am still working for the foreseeable future due to my second divorce. “

12. I wish I found a way to trust others to handle my non-billable affairs.

“Being a perfectionist lawyer for decades, I developed a thick shield when it came to trusting others.

This led to a bottleneck in my decisions outside the office. I was always double-checking and confirming. I should have talked to a counselor or therapist to relieve some of that concern potentially. I handled my own investments, which was stressful, and from time to time, distracted me from my Practice of Law.

I wish I could have discovered a level of trust to have someone manage that for me.”

13. I wish I dealt with my debts better.

“I didn’t realize how fast the years were going by, and I thought I would work until well into my 70’s, but I got ill in my mid 50’s and was forced to slow down.

I did not account for this situation as I was not paying my debt down with the strategy or discipline I should have been. It provided for high stress in dealing with my illness, while trying to keep a skeleton staff in my Practice, managing debt and putting one child through university.

I wish I had been better with my discretionary money and putting it towards debt paydown and potentially some insurance.” 

14. I wish someone gave me “clarity” skills in my 30’s that I could use year after year.

“No one challenged my belief’s around money and financial habits I had for decades. I felt as though I tried my hardest, but I was never clear on my financial direction.

Taking the time to get financially organized once and learning how to do that would have been beneficial to use those skills over my life. Getting grounded, clear, and then being able to make decisions from a place of certainty, power, and independence would have been something I wished I had.”

15. I wish I ran my Law Practice more like a business.

If I would have thought more about systems and processes in the early days, I believe it would have freed up more time in my later years to enable me to make the same money, with a fraction of the effort.

In the later years, I started paying attention to my financial statements and my expenses, but for the bulk of my practicing years, I simply tried to make more money and believed that would solve all my problems. That worked until it didn’t.

Having a slight diversity in my revenue streams and smoother operations would have increased my profit margins and allowed for a more graceful retirement, not the abrupt situation I am faced with now.”

16. I wish I bought “the right practice” instead of buying the first one I could buy.

“From the get-go, I did not simplify my office infrastructure, on/offline file management, automated marketing, and I did not look to buy “the right” Practice to fast track my growth.

I bought a practice of unhappy clients, unfinished work, and more unproductive work than I could have ever imagined. Spending extra time and being more patient initially could have let me set me up my foundation practice to execute better the level of customer service I envisioned.

Decades later, I have now put a process in place, so my Practice is worth something, someone can take it over, and the client service will continue.”

17. I wish I started investing a smaller amount sooner than cramming lots of money in when I was nearing retirement.

“With the recent COVID health investment market crash, it makes me realize how risky making one-time lump sum investments are.

The timing of investments plays a material impact on rates of returns in investments. If I had made smaller monthly investments from an earlier age, it would have spread my risk (and stress over many years). Making larger deposits into my retirement investments as I near retirement, I realize has a more significant risk of market fluctuations, but if I am not selling, it’s fine.

Automating my savings would have been less stressful and made it so each time I invest, it isn’t a HUGE decision I have to revisit, research, and stress about the weeks leading up to making it and the weeks after.”

18. I wish I thought about how and when I would exit my Practice sooner.

“At least having conversations about what a potential exit looked like well before I was retiring or slowing down would have given me more options. Striking up conversations with younger Lawyers in my networks or on Linkedin would have given me more of a talent pool to work with in selecting a succession plan for my firm.

At this point, I believe I would have been able to transition the clients more seamlessly with the right Junior, and or I would have been able to sell for more.”

In Conclusion

Everyone has their life circumstances that will ultimately dictate how the decisions you make today will shape your life (and the people in it) of tomorrow.

If you’re interested in learning more about how Serviss Wealth Management is helping lawyers like yourself – BOOK A MEETING HERE