Sometimes, I like to go on LinkedIn and see what people are up to. I like LinkedIn – I think it’s more interesting than Facebook or Instagram. Looking at what someone shows you of their life is one thing. But seeing someone’s career progression over the years is more insightful. After all, we spend most of our waking hours working. LinkedIn gives you a window into what someone does for most of their day.
As I was browsing LinkedIn the other day, I noticed that a bunch of people that I went to law school with made partner at their law firms. I still feel really young – and I’ve always thought of partners as old (or at least not someone in my generation). But the math checks out. It’s hard for me to believe it, but it’s been 8 years since I graduated from law school. People that I went to school with really are becoming leaders in the profession that I was once a part of.
I only lasted three years in big law before I flamed out. And it’s now been two years since I last had a normal 9-5 job. I’m making a living doing what I do – writing, blogging, doing side gigs – but I’m not rich by any means. It’s just enough for what I need at this stage in my life. And I’m happy that I control so much more of my time and life, especially now that I have a kid.
But at the same time, I always deal with feelings of regret and what-ifs. What if I had tried to stick it out? I’d definitely be making more money right now. I wasn’t a great lawyer, but I could have gotten better at it if I had changed my mindset and wasn’t so focused on getting out.
Even now, after two years of doing my own thing, I still cling to my law degree. The front page of this blog still calls me a lawyer. I still haven’t given up my law license either. And I still pay my annual dues because I’m afraid of completely severing myself from my prior career.
That Feeling Of What-If
I’ve always had this problem of dealing with what-ifs, worrying about the grass being greener on the other side. When I was practicing law, I changed jobs three times in 5 years, all in search of a dream job that I thought I could build my life around. None of these jobs panned out though – I wasn’t happy in any of them. What if I had tried to stick it out in one of those jobs? Maybe I’d have a successful legal career and be making a lot of money right now.
Or what if I had done things differently in college? Instead of goofing off and playing video games as much as I did, I could have worked just slightly harder and had much better grades. In my first year of law school, I worked harder than I ever had in my life – so I know I had the ability to work really hard at school. That hard work I put into law school resulted in me ending my first year ranked 13th in my class. I likely could have transferred to an elite school like Columbia or NYU. But I didn’t do that. How different could my life and career have been if I had done that?
I have a lot of things in my life that could have gone in a different direction. I’m sure many of you have the same things in your life that you wonder about – events and circumstances that could have gone in another direction and resulted in a completely different life.
But we all have to make decisions based on the information that we have at the moment. It’s the same truth that applies to all of us – none of us really knows what the future holds. We do the best we can with what we have at the time. And we can’t change the decisions that we make. All we can do is learn from them and maybe make better decisions later.
I’ve had a problem with chasing prestige for most of my life. There’s nothing inherently wrong with wanting prestige – it usually means higher salaries, more respect, and all the things we associate with a good, upper-middle-class life.
But for me, prestige felt like a trap. It put me into a job and career path that wasn’t a good fit for me. It made me work long hours doing something that didn’t satisfy me. I often try to tell myself that I don’t care about prestige. And maybe I don’t care about it as much as I used to. But I do still care. It’s ingrained in all of us to want respect and admiration. No matter what anyone says, most people do care about what people think about them.
Seeing my old colleagues advance in their careers while I’m still sort of figuring things out still doesn’t feel great. If I had stuck it out, maybe I’d be moving into those higher levels too. It’s always a battle for me between wanting prestige and wanting a life built for me.
Make Decisions For You
Whenever I’m feeling regret about something – like when I look back at my legal career and how badly I failed in it – I realize that a lot of how I feel isn’t really about me. It’s about what people think of me. These days, I try to think about my decisions, not in terms of what other people think, but in terms of whether the decision is right for me.
I’m still figuring things out. Even now, in my early-to-mid-30s, I’m not exactly sure about who I am and what I’m all about. I do know that the two things I care about most when it comes to work are controlling my time and my life. I’ll always trade less money if it means more control of my life.
I’m not a partner at a big law firm. I’m not even really a lawyer anymore. Maybe I could have gotten there if I had stuck things out and kept grinding at it. But I decided that this was something I couldn’t do – or at least it wasn’t worth it for where I was in my life.
Today, I write for a living. I don’t make the most money I could make. But I’ve got enough to do what I need to do. That said, I can’t say that I don’t wonder about the what-ifs that could have been. I’d be really rich if I had kept struggling through for those big six-figure salaries.
But we have to make the decisions for ourselves, based on what we know. Some of my classmates stuck it out. The decision was right for them based on what they knew. I didn’t stick it out. It wasn’t the right move for me – at least based on what I knew at the time.
None of us can know the future. We can only know the past. All we can do is work with what we have, figure things out, and move forward with more knowledge later.
FI for the People says
Apologies in advance for this long comment, but this post resonated deeply with me as a nonpracticing lawyer (who’s got more than a decade in age on you). First, I totally empathize with you (I mean, I, too, have kept my law license up, even though I don’t intend to practice). But I’ll offer a few thoughts. “I only lasted three years in big law before I flamed out.” I would suggest that you practiced law in BigLaw for three years before you decided that that wasn’t for you. Flaming out, I think, implies some personal failure. Rather, you made experience-based decisions. That’s what rational people do. And there’s honor and, for lack of a better word, courage in acting on that decision. The sunk cost of money and time (not to mention the golden handcuffs) is hard to walk away from. That’s why so few people do it. And as for the idea that if you’d have stayed in BigLaw you’d have continued making bank, yes, that’s true of course. But, as you recognize, at what cost? Brutal hours and lost weekends. Stress-inducing demands from (equity) partners to which a “no” is not an option. And (if this applies to you) doing work for clients for which you may share little or no sympathy. And as for the “prestige” that comes from making partner, as they say, making partner in a law firm is like winning a pie-eating contest where the prize is more pie. I know a ton of lawyers. Few are truly happy. Some are and have always been unhappy practicing law. Most are just resigned to their situation. That seems a miserable way to spend (likely) four decades of one’s life. I think it’s always good to question where you are in life. But the measure should be whether you’re safe and cared about by others, can care about and provide for yourself (and dependents), and are healthy and happy. If those boxes are checked, you’re in amazing shape, even if you could improve on any or all of those measures.
Financial Panther says
Really appreciate this insight. It’s interesting – my use of flaming out of biglaw suggests a personal failure on my part, as if I wasn’t good enough. I guess this something that I and many driven people deal with. There’s this idea that quitting is a personal failure, but often, it’s a decision that we make.
Financial Samurai says
It’s funny you say this, because a friend of mine for the past 20 years is now going to be the co-head over $200 billion private mutual fund. Which means he’s probably going to start making tens of millions of dollars a year. And another friend just bought a $25 million house!
I’m really happy for the success. Is there a success does not impede upon my success. The good thing about lasting a while is that your friends all become wealthier and more powerful. If they are really your friends, they can help you and your family get out as well. Therefore, never forget your friends.
Personally, My goal is to maintain Financial Samurai has a top personal finance website that is independently owned and independently written. That’s good enough for me!
Financial Panther says
Good enough is a good goal!
I feel this so much. I decided towards the end of college that I wanted to pursue an academic career in science. Nevermind that my science courses felt like a slog and my literature courses made me happy. Science seemed like a secure path and it made my dad happy, so I convinced myself that it was what I wanted. (I realize now that academia is anything but a secure path; however, back in 2008 toiling away as a low paid research assistant at a top medical school felt like winning the lottery when so many of my peers were getting laid off or struggling to find jobs.) After 3 years of working and post-bac classes and GREs, I made it to a fully funded top-10 PhD program in my field. And then it took me 1.5 years to completely flame out and quit my program. It turns out that it’s really miserable to work on a degree for 6+ years when you don’t love what you’re studying.
Sometimes I look at some of my former classmates on LinkedIn and feel like a gigantic loser because I’m not a doctor of anything. But the unflashy 9-5 jobs I’ve worked for the past 8 years afford me financial stability, plenty of free time to spend on hobbies like reading, and– most importantly–my mental and physical health.
The chair of my grad school department was a really kind man who started his studies in a completely different field before pivoting to science. He was very supportive when I decided to withdraw on the grounds that this was my life and that it would be a complete shame if I wholly dedicated myself to something I found unfulfilling.
Financial Panther says
Thanks for sharing your story.
One mistake I think a lot of us make is thinking that life moves forward in a straight line. But we know that life isn’t like that. We all follow our own path – it backtracks, it goes forward, it gets windy. No way to know what life will hold for us. Glad you made the decision that was right for you. FI For The People mentioned this in his comment, but you didn’t flame out. You made a decision that was right for you based on the information you had. And only you can make the decision, no one else can.
You did the right thing Kevin by not going after the almighty dollar. What you gave up in the short term $$$ you will make up in retirement years with a guaranteed pension and health benefits for you and your family.
You have found multiple outlets that you are free to explore that you wouldn’t have time for in a legal firm. It would benefit you health wise, NOT to check up on your past connections. That is in your past- you moved on. Stay focused on your family, your hobbies, and your investments.
You made a commitment to do it your way , just keep doing that -Your way, that gives you peace and recognition. Build on that-don’t try to tear it down. It will only eat at you.
Financial Panther says
Good insight Joe. Thanks!
So eerie how close this post resonates with me. It’s almost as if I’m reading about myself. Love this blog.
Financial Panther says
Thanks Bao! Glad it resonated with you!
Kevin Morison says
You’re making all the right decisions, Kevin. Doing what makes you happy and fulfilled is so much more important than prestige or money or really anything else. As I approach retirement — yes, old-timers read and learn from your blog too — I occasionally think about some what-ifs myself. What if I had found and stuck with one job (especially if it had a defined benefit pension plan)? Or gone to law or business school myself and earned a lot more money than I ever did? But as I reflect on my career (which has included seven jobs in the private, public and non-profit sectors), I wouldn’t change a thing. I’ve worked on a ton of interesting and meaningful projects and met and worked with some incredible people. And along the way even earned some “prestige” (more like friendship and respect) from people who really matter to me. So keep on keeping’ on and do what brings you joy.
Financial Panther says
Average Joe says
this post reminded me when at 28 i was thinking of dropping out from my engineering job. i am now 38 and still in engineering plowing ahead. The reason i did not drop out is because i did not know what i would do otherwise. so i just stayed. financially, im ok, i got 600k saved and probably will work til i hit 1 mil. im the most boring person ever, for past 16 years, i wake up every morning and go to work. i am not the best at my job either lol, still low in food chain. but as i get older, i realize, this is exactly how i want to live, boring. There is no right or wrong choice, whatever choice you make, you cant change it later on. at this point for me it is all about hitting my fire # at 1 mil. just perspective from someone who stuck it out. it is not any greener on this side of the fence.
Financial Panther says
Thanks for the different perspective. My guess is there’s green and brown on every side of the fence.
Great post FP – and how well it resonates with so many of us. I was one of the smarter ones as well – the guy I sat next to in high school is a professor in Princeton. I met him a few years back – he looked at me and bluntly told me I was nowhere where he thought I’d be. It didn’t bother me, he was right. I was happy he thought highly of me.
Since then, I got married to a wonderful wife, now have a daughter, and well on my way to FI. Those 3 alone makes me feel like I’ve accomplished a lot, in a different way, even though I don’t have the job title to suggest it.
I’ve followed you over the years, and you’re not very different from me, I think (except you hustle a lot more, have more energy). It’s easy to say be happy where you are – but there’s something about stealth wealth, living simply and away from the the spotlight that appeals to me, and is more sustainable on the long run.
This resonates with me so much. I think it’s a factor of online social networks and staying virtually connected with friendships that have run their natural course where as prior to social media we would otherwise know nothing about these people and what they are up to. I sometimes think about my grandmother who would only know news of her past classmates if a friend of a friend told her. And those direct stories would have likely been closer to the truth of the reality rather than just a highlight update to linkedin with a title change. Maybe behind that promotion is a divorce? Maybe not. Sometimes we will never know if it’s someone we are not close with. I admit I am constant comparison mode. Social media will often have us feeling bad about a good life and it’s hard to not ask the what ifs. You make a smart point about distinguishing what we want for ourselves and what we want others to think of us. This line often gets fuzzy. Who are we without the context of others? It’s almost inevitable to fall into this trap. Thanks for sharing this post. I think your blog is inspiring and super informative!
Your posts are really an inspiration. Remember that there are also plenty of people who look up to you for inspiration. Also, there are probably a significant number of colleagues who may envy your path.
Keep up the good work!
David @ Filled With Money says
Kevin, thank you for sharing this. I’ve been contemplating this point for the longest time. As much as I would love to retire early, there’s a part of me that feels like retiring early means that I’m giving up. When I read that Jeff Bezos was retiring, I felt that he was essentially giving Elon Musk a free ticket to be king and #1 afterwards. A part of me felt empty hearing that Jeff was retiring.
I know that their successes aren’t my failures but it just doesn’t shake the feeling that it feels like I gave up and lost.
It is quite impressive that your friends became law partners after only eight years, wow that’s quite an accomplishments. Have you gotten to talk to them if they are happier? Truly happier and not just them showing what’s on the surface. I’m sure they have to make immense sacrifices to get to where they are and that they’ll have to continue making sacrifices.
I totally feel the same way. I had started out my career very brightly. I was one of 10 people recruited by a major company to be in a Leadership Training program straight out of Grad School (all 10 of us had MBAs from prestigious universities). It was a very selective process (only 10 got picked from hundreds of applicants) and it was to train the future leaders of this Fortune 50 Company. A few years after I joined, I got married and started having kids. I put my career in the back burner and focused on raising our kids while my cohort pursued even higher positions in the company. Most of the 10 people are now either in Senior VP roles or are Managing Directors. I am still just a Senior Manager (just 2 levels higher that when we all started). There was that fork in the road 25 years ago and I feel that I picked the wrong road. I will always have regrets in the way I pursued my career choices.
I enjoyed reading this one. I think the truth is that no matter how put together someone looks on the outside, we are all still just trying to figure ourselves out on the inside. The feelings you express are normal and widely felt, regardless if people admit it or not.
I’m kind of doing the opposite of you. I’m trudging through the corporate life in order to bow out a little later in life. I’m also doing this more for my wife, so that she can be a stay at home mom. I have the higher income and it’s easier for me to “take one for the team” so to speak.
Playing the comparison game will only lead to frustration. You made a good choice for you and are now having an adventure. Keep it up and I’m looking forward to seeing what your future brings.
One of the nice things about following a FIRE path is, it is what you make of it. There is only you directing your path. I am not completely withdrawn from my pharmacy career quite yet and find myself really interested in what some of my fellow classmates are up to. I know they have worked hard and spend a lot of time away from home making those goals happen. I know because I too accomplished a lot in my 10 years. I am happy where I left and every day, I am thankful what was my job is not my job today. I see the demand and the stress it puts on my colleagues and helps nudge me out the door even more.
On the other hand, I will never give up my license. I would say that I am a pharmacist as part of who I am. One of the reasons I chose this career because it is so versatile. I can do so much with it and it will always be there for a side hustle if needed.
We are all still figuring it out and that’s quite alright. Do what is right for you and make the choices that fit you and your families life best. After all, isn’t spending more time to do what we want with whom we want the ultimate FIRE goal.
charlie @ doginvestor.com says
Work part time as a lawyer? Is it always all or nothing?
I resonate with the post too! I worked in private equity for 8 years before switching. Prior to that I worked in another industry. Right now doing the FIRE thing for a bit. Although my industry was more known for people retiring at a younger age and then moving onto new things – at least those that did financially well.
Not doing law now, doesn’t mean you can’t ever do law, that your life is static, or that moving between things is a bad thing. You might think of it as floating, I like to think of it as having options afforded to you by your own financial independence. It’s a success to move beyond a desk job, not a failure to stick it out.
That being said, it would be nice to continue to earn a huge income doing something we love with less hours than required by the institution, haha.
NZ Muse says
Gosh do I feel this! I see peers becoming managers, Head Ofs, etc … one person has even started her own successful agency and is leading the way in the industry, having huge success and sharing their latest awesome projects, and I then see on FB her lovely new lifestyle property… I’m working on refreaming this as EVIDENCE of what’s possible rather than sinking into envy.
“…. if I had changed my mindset and wasn’t so focused on getting out.”
I have thought this also about the FIRE movement in general, that this could be a very real downside of the whole thing.
I appreciated this post, Kevin. It resonated with me as another lawyer whose early career has not unfolded exactly as planned. I have also spent years caught between “wanting prestige and wanting a life built for me.” In the process, I learned that “a life built for me” is not life as a big law associate. That’s not to say my tenure in big law was a waste; to the contrary, I learned a lot. In particular, I learned one very important lesson about prestige.
High prestige, in my mind, correlates directly to the number of hours you spend each day doing what you want, when you want, with whom you want. I didn’t think about prestige in this way before big law. But after many long nights attending to stressful and sometimes mind-numbing matters, I sure do now. So in that sense, Kevin, you are far more prestigious than any newly minted law firm partners (especially the ones who hate practice but solider on because they need the money or can’t think of anything better to do with their lives). You seem adept at controlling your time and have the money to live the life you want. That, to me, is very prestigious.
Moreover, you are building something. Personally, I left big law with one ironclad belief about the business world: the only truly prestigious business accomplishment is building something new; entrepreneurship, that is. Everything else—from flipping burgers at McDonald’s to rising through the ranks and becoming the CEO of an investment bank—is just a job. A bit of an extreme position, I suppose, but that’s how wide I feel the gulf between entrepreneurship and “everything else” is.
Reflecting on my time in big law recently, I thought about the various on-site due diligence assignments I handled as a corporate associate. I recalled visiting the companies’ sprawling campuses or massive skyscrapers, their abundant cafeterias, their on-site gyms, and noticing the countless employees scurrying around to accomplish discrete tasks on any given day. Pondering these trips, it blew me away that once upon a time these companies were all just figments of someone’s imagination. Then, piece by piece and sale by sale, they grew from nothing. *That* is prestigious. Climbing the greasy pole of success within an organization is not nearly as impressive or prestigious as envisioning and building the pole in the first place.
I am not surprised this piece struck a chord with so many readers. The nagging drive to feel “prestigious” after investing substantial time and money in a college degree (and perhaps graduate school) has diverted countless people from their true—if perhaps more uncertain and initially less lucrative—callings. Sometimes, this tension seems like our entire over-educated generation’s curse…myself included.
Dave @ Minimalism and Your Money says
I think you said it all when you mentioned that the two most important things are control of your time and control of your life. Of course, it’s tempting to look back on what could have been, especially when it comes to more money. (Hell, I’m a teacher. Talk about financial regret!!) but you mentioned so many important, valid reasons that you left your career as a lawyer. Those reasons win out over money every single time!