Imagining the Future and My Best Exit Scenario

I’m generally not an all-or-nothing person.  As a lawyer, I like to manage and hedge risk.  The thought of giving notice seems so…final.  I view it as the exchange of a stable and financially rewarding career for a dream of freedom, exploration, and fulfillment.  Need more money later?  Well tough luck.  With the financial markets suffering a bit of turmoil lately, I haven’t been feeling as confident about making the leap.

Compounding the issue was a series of interactions I had while traveling last week.  I don’t come across people who are down on their luck very often.  As I freely acknowledge, I live in a bubble of big firm lawyers and in-house counsel.  I had a series of Uber rides with very talkative Uber drivers, many of whom were driving because they experienced layoffs or were unsuccessful in their primary ventures (e.g., one driver was a struggling movie director).  The thing that these drivers had in common, was that despite their circumstances, they couldn’t help but talk about how talented they were, or how well they did in the past (all of this being completely unsolicited).

imageI don’t know anything about these drivers beyond what they told me, but I couldn’t help but feel they were deluding themselves (e.g., the driver who was trying to convince me he was on the verge of a huge movie deal), or maybe embarrassed (e.g., the driver who kept trying to explain why he was driving an Uber despite being so great at X, Y, Z). Now, I’m not trying to judge these guys, as I could easily see myself falling into that trap in a worst case situation.  I even imagined myself as an Uber driver in the future:

Me: Where am I taking you today?

Passenger: Airport.

Me: Great.  I’ll get you there in 15 minutes…Hey, did you know I used to be a lawyer?

Passenger: Um, no…

Me:  I practiced for over ten years at some of the biggest firms.  But I drive an Uber now.

Passenger: Oh, interesting…[looks down at phone to see how long the ride will take]

Me: Yeah, you know it was totally my choice to leave and all.  Just didn’t like it that much.  It’s not that I couldn’t hack it, you know?  [Stares at passenger in rear view mirror to make sure they know this.]  It’s just being a lawyer at these big prestigious firms requires such a sacrifice.  I could totally have kept doing it though.  The money is really good, but not worth it in the end…

[Fifteen minutes later]

Me: …and at my second firm, the partners would hog the clients and wouldn’t share credit…Oh looks like we’re at the airport and this is your terminal.

On my last Uber ride, it dawned on me that I was going through Scrooge’s experience with the Ghost of Christmas Yet to Come.  The thought of me being like that was hard to bear.  But I could see my future me devolving into someone with a starved ego who needed to justify a disappointing situation.  My ego’s been pretty well fed for the last few years.  I’ve been weaning my ego for the last 5+ years to separate my career from my identity, but I know part of my ego will still yearn for success and prestige.  Not knowing what’s to come is a bit scary.  At the same time, I could see myself as a worn down 65 year old lawyer, interviewing some law student:

Me: You know, I’ve been practicing law for 40 years.

Eager law student: Yes, I hope to do that too — I love the law and want to practice at X, Y, Z firm!

Me: It takes a lot of hard work and dedication.  I’ve suffered through alcoholism and addiction and sacrificed time with my family.  My kids hardly speak to me.  I can’t believe they’re so ungrateful even though I paid for private school and bought them each a new BMW for graduation!  But the law has always been there for me.  I’m so glad I gave up everything for it.  I feel so fulfilled spending so much time in this office.  Did you know this desk is mahogany?  [Knocks on desk]  I took over this corner office from Chris after he suffered his third (and final) heart attack.  Poor bastard!

Uncomfortable law student: Um…OK.

Anyways, this is a long-winded way of me saying that I’m trying to think of more creative solutions than just quitting and hoping for the best.  I know of some attorneys who stayed on the payroll and get paid by the billable hour, instead of receiving a fixed salary with an expectation of hitting some billable hour target.  This seems like a good solution for someone who doesn’t need the fixed salary.  This approach would also minimize any risk of burning bridges.  The firm would be incentivized to agree as there are a few significant matters coming up in the next few months where the firm perceives that my involvement would increase the likelihood that we would get the work.  I could help get it and then not do much while we’re traveling, and when we get back, I could do as much or as little as I wanted.  Anyways, these are just some ideas I am considering given the markets and my own state of mind.

14 thoughts on “Imagining the Future and My Best Exit Scenario

  1. I was in an Uber the other day with a senior man who was explaining to me how he is retired and just drives Uber to keep busy. He also trades currencies at night.

    The only issue with staying on hourly, is that could turn into full-time all over again. Unless you set strict boundaries. Best of luck!

    • Thanks for the comment, FF. I hear you about the risk of turning into full-time all over again. I guess part of me wants to keep that door open in case the economy goes south for an extended period.

  2. I certainly see where you’re coming from and the legitimate anxiety you’re experiencing. I think it’s a huge shift for you, more than just what to do with the achiever and doer inside you. The great news is that thanks to your discipline, you are not trapped, and you can take your time and figure this out. I worry about what you’re going to end up doing post-travel. I know Uber won’t cut it. The billable lawyer idea is reasonable, but most places I know who have hourly worker give them the less enjoyable work. Also, you will have to really exercise the discipline to keep it part-time which I imagine will be very hard given your previous work style and the expectations of large firms in terms of what’s a reasonable expectation of hours. If you happen to practice a form of law that would translate well in the entrepreneurial world, I recommend first volunteering at some startup factories to help people with basic decisions like setting up LLC vs. S Corp vs. C Corp and strategic partnerships and negotiating with tech transfer. Those kinds of things are in demand, and putting yourself out there would be great networking in a new space. Plus entrepreneurs are fun because of their energy and passion. That’s just one idea. I wish you all the best, and know that you’ll execute with diligence and patience.

    • Thanks for the feedback Slug. Yeah I wasn’t suggesting driving an Uber. I was imagining a transition into a state of mind where I constantly felt the need to justify perceived failures to others. I will definitely think more about your suggestions. I’ve also cultivated some new hobbies, which have sparked a renewed curiosity about certain things.

  3. I’ve been transitioning away from legal practice. I’ve picked up training as a mediator and I’m doing mediations part-time and law part-time. I’m trying to get ride of legal practice (llitigation) altoghther. I’m much happier doing part-time mediations.

    Also, I’ve taken up long distance running and cycling. I find that this satisfies the Type A personality in me and the competitive part of me. It’s about finding balance.

  4. I just found your blog and read it from start to finish. First, congrats on finally giving notice. As I read your blog posts starting in 2009 and started seeing you give countless justification for staying at the firm, I worried about whether you’d justify never leaving the firm. It was a depressing reader experience for a bit, but glad to see you finally followed through.

    Second, please don’t justify your way into staying at Big Law. You’re extremely unlikely to find your passion or figure out what might make you happier in life while you’re at the firm. It just sucks up a lot of energy and bandwidth, and it keeps you in the same frame of mind that you’ve been in for over a decade. I wasn’t happy at Big Law, and finally I realized that I just needed to leave so I could have the mental clarity, time, and overall freedom to figure out what I wanted to do next. And it might not come to you in the first year or two. You might waste too much time sleeping in and watching TV. That’s okay. Try to find ways to be helpful – volunteer for a cause or two. And see where life takes you. Take a risk. Leave a job you’ve been writing about hating (or merely existing in) for over a decade.

    You’re killing me with your travel posts. I beg you, CHILL OUT! You’re defeating the purpose of traveling around the world. All you needed was your 1-way ticket to Australia. That’s the beauty of travel without at timeline or a finite budget. Let the rest unfold as it will. You have no idea what amazing places you’ll discover once you’re overseas, what you’ll learn from other travelers. and how that will affect the way you spend your time. You might want to linger for weeks in a place where you planned to spend 2 days. Stop with the planning. Just go. Learn as you go. Do whatever you want whenever you want. Find nice island that you planned to spend 3 days on and stay for a month (this has happened to me many times in life).

    Also, stop your dependency on luxury before you ruin this trip and let it suck away your freedom! I’ve never heard of someone neurotically planning ahead a long-term trip as to maximize upgrades and such. Yuck. Once you take a couple of economy class tickets, you’ll get used to it again just like the rest of us and just like you used to be before you got accustomed to luxury travel. Value your freedom more than you value a fancy seat for a half-day flight. Stop booking things. Stop strategizing around getting the most luxury possible from your frequent flyer programs and clubs. What’s going to make you happy is all of your travel adventures, not whether you got from country A to country B in a slightly fancier fashion.

    In fact, please consider using travel as a way to experiment with throwing luxury out the window. In SE Asia, stay at hotels that cost $10-20 a night. Eat street food (yum!). Travel using local buses and trains. You’ll get some good stories, and you’ll learn that it’s possible to be happy while living on next-to-nothing. Imagine how empowering it’ll be to learn you can be happy spending so little while having nearly 2 million in the bank.

    Please cut out all future justifications for working at the firm. Life really is too short to do that to yourself. Your children do not need college paid for – most don’t get it paid for, and they do just fine (in fact, It think I was better off having to work to contribute to all 3 of my degrees, as I had an awesome resume when I graduated). And depending how cheaply you decide to live and if your kids choose an affordable college, you have enough to pay for that anyway. TRY actually being retired (or at least not working at a law firm or at another job just because it pays well). TRY being CONTENT with what you have. See how it feels before you freak out.

    Finally, having read through all of your posts, I must tell you that “anyways” is not a word. You’re killing me with that. It’s “anyway.”

    • Completely agree with MK when it comes to trip planning and just seeing where it takes you. I would love to know your thoughts to his comments.

      “Anyways”, it’s almost December.. time for an update!

      • Hi DPS. Thanks for the comment. Been neglecting the blog lately due to some work travel and some other stuff. Still working towards D-Day. Will try to write a post about our travel/transition philosophy when I get a chance.

  5. I am always glad I stopped by your blog as your writing has some mysterious power that allows me to add more emotions into it and make me come back for more. I am an accountant that used work with a big 4 firm but I enjoy a lot more now at a small public company. I dream about working as a part-time consultant without fixed salaries but in order for that to happen, I will have to live within means for another decade or so. Haha



  6. I recently experienced something similar after I quit my law firm job to travel for six months. I don’t think I fully grasped how much my identity was tied up in being a lawyer! I am not ready to retire yet, and am working on making a career shift. It has required a lot of introspection and honesty to separate myself from my desire to have an important-sounding job. Best of luck to you! I just found your blog and hope you keep writing, as I can totally relate to your story.

  7. I love your blog. It continues to inspire me.

    I have been thinking a lot about post-FIRE universe for attorneys. I am a fifth-year BigLaw associate so retirement, though still very far, is a realistic possibility.
    The truth is that many attorneys derive significant amount of non-monetary satisfaction from their work and from simply being a lawyer.

    Part of this satisfaction comes from being good at your job. Most of the time, this satisfaction gets crushed beneath the multitude of problems inherent to the BigLaw model. But if you have the power to say “no” and establish clear boundaries then the problems will fall away. Your law practice then becomes your hobby with a bit of income as an added bonus.

    Part of the satisfaction also comes from the social approval one receives for being a lawyer. I know that those of the FI-track are not supposed to care about titles and other status symbols. I am certainly not suggesting that one should trade family dinners, exercise, and social life for a fancy car or being able to call yourself “Partner.” What I am suggesting is that being able to say that I am a practicing lawyer would give me positive utility if the only downside is answering an occasional email from home on a Wednesday afternoon. Perhaps that is just me.

    With these two points in mind I would definitely suggest that you negotiate with your firm — or another BigLaw shop — some sort of “Contract Counsel” arrangement. I have seen one counsel and one associate going “contract” with their firm. For both of them the arrangement worked out beautifully. The hourly pay in both cases was very generous and both individuals felt like that could either accept or reject any particular work request.

    Think about it. The only downside is that you yourself may not be able to resist the siren song of more and more billable hours. As usual, the greatest obstacle is in one’s own head.

    • Boris — thanks for your thoughtful comment. Your idea of going contract has crossed my mind before. I’ve also seen others do it (actually looked up your LinkedIn profile and we may have worked at the same or similar firm but in different offices). I’ve seen it work out well in some cases, but in others, the contracting attorney lost interest in a short amount of time. I will definitely meditate on this as we travel next year. The issue of what to do after we get back continually burns in the back of my mind. I think we all need a purpose in life and sometimes I wonder if I put that purpose too much on a pedestal. Maybe doing what I already do is good enough, but I just need it in a smaller dose. Then I start getting nasty e-mails from opposing counsel or a senior partner and I do a 180 and think that life’s too short to have to put up with this crap. The back and forth has been pretty constant over the last few years, and it’s pretty hard to avoid the negative in my practice area. I think the time away will give me the perspective to disassociate the vanity aspects of the practice of law (pay, prestige, etc.) from what’s important.

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