The Shackles of Success

I was able to walk away from a mid to high six-figure salary, but it was difficult.  I had to psychologically condition myself to be able to leave.  I realized that the longer I waited, the more difficult it would have been to leave.  My departure surprised a few people, but ultimately did not materially impact any of my firm’s strategic goals.  Had I waited until I was a full equity partner and had a substantial book of business (who knows if that would have been in my future), it would have been way more difficult to leave. Not only would the firm want me to stay to retain my business, but so would the attorneys working on my matters, and the clients themselves.  I would feel really guilty about walking away from all of that, especially if I was being paid well for my efforts.

Side note: on the flip side, if I had waited and was unable to continue to succeed (e.g., didn’t make full equity or couldn’t build a large enough book), then I would have felt that leaving at that time would have been like admitting defeat.  Now I will never know if I could have achieved all of that, but it feels better not really knowing.  All I know is that I had a good trajectory at the time I decided to leave of my own volition.  So in a way, it was like leaving at the top while I was able to leave.

In Crossroads of Should and Must, Elle Luna defines “career” as “a system of advancements and promotions over time where rewards are used to optimize behavior.”  (The blog post that led to the book is a must read.)  I think this is a good definition.  At the early stages of a career, advancements and promotions are critical to success.  These incentives open doors as employees have more options to climb the ladder in their organization or lateral somewhere else.  You can also develop new skills as you are given more responsibility.  But at the higher levels, a promotion has less meaning.  Incentives for senior folks tend to take the form of more money and more responsibility.  But these incentives tend to close doors rather than open them and act as shackles.

Take an extreme example: imagine if Bill Gates decided to walk away from Microsoft once he crossed the one billion dollar mark.  He would have profoundly impacted the lives of not just his employees, but also his investors, and potentially rocked equity markets around the world.  That’s a lot of pressure for one person to bear.

I’m not suggesting I am anywhere close to Bill Gates.  Looking at my circle at work, the partner I worked with was a superstar.  He brought in anywhere from $20 to $40 million of business a year and was paid a handsome $5 million a year.  He fed billables to 20 to 30  attorneys around the firm.  He is the ultimate type-A attorney and is addicted to the money and status.  But even if he weren’t and he felt like he wanted to make a life change, he’s so locked into his current situation, he would literally have to turn his life upside down and affect dozens of people (potentially thousands, if you count everyone in the firm as well as clients) to do so.

He’s built this empire that has consumed him and his entire life.  While he is paid exceptionally well, he is captive to that empire.  Clients snap their fingers and he gets on planes and puts people to work.  He is incentivized to bring in more work so he gets paid more.  It’s a relentless treadmill that gets faster and steeper over time.  In striving for success (which he has more than certainly achieved), he has also built a prison for himself. But it’s still not enough. He once told me he didn’t think $100 million was that much money for an individual…but he conceded a billion dollars would be a lot of money.  I should have pressed him for a more specific threshold…maybe $358 million?  Anyways, I think he is genuinely satisfied with what he has accomplished.  But to me, it looks like the darker side of success.

10 thoughts on “The Shackles of Success

  1. wow. i’ve never known a lawyer that “successful”, although many sucessful by normal standards. that guy is trapped in a nightmare, and has to some degree lost his mind. how can a man be so inefficient that needs 100 million? it’s almost like he is retarded in some way to need that much.

    On Sat, Apr 30, 2016 at 10:11 AM, Thoughts of an Anonymous Lawyer wrote:

    > anonlawyer posted: “I was able to walk away from a mid to high six-figure > salary, but it was difficult. I had to psychologically condition myself to > be able to leave. I realized that the longer I waited, the more difficult > it would have been to leave. My departure surpris” >

    • You’re right, David. And he casts a long shadow over those who work with him. You get sucked into his world, as he is very open about what he makes, what he buys, the country clubs he belongs to, etc. as well as what others at his level do. It’s interesting to have insight into this world and sometimes it’s scary when you acclimate and it doesn’t seem as strange as it used to. But you’re right it’s totally messed up!

  2. One that, that lawyer is not going to be there anymore. Whether by choice or by circumstances. It will turn out that his place will be quickly filled with someone else, or perhaps by multiple people. And if not at his firm, some other firm will get the work. The work will be done, he will be missed for a while, but then the show will go on. That’s life.

    While I also have a small role at a specific company, I have no doubt that when I leave, others will fill the gap. I’m perhaps even glad that I’ll be able to give someone else (who may really need the money) that possibility; while I go off and enjoy the rest of my life 🙂

  3. The Golden Handcuffs. I think almost everyone in a large company is replaceable at the end of the day. But there are a few superstars who would be hard to replace as you pointed out. I think it’ll definitely be easier, as you mentioned, to call it quits before becoming a full equity partner. Because then your decision would of actually affected others, whereas right now if I left my job, I believe that would hardly be the case.

  4. my attorney father-in-law is founding partner in now 20yr old litigation/advisory business that now has 20-30 attorneys. he probably had enough money to retire before he started the firm. he is the rain maker and now over 70y/o. he claims the money for him is less a consideration than those people that he puts to work and their well being, livelihood etc.. the juniors and yeoman aren’t proficient or proficient enough (in his opinion) in bringing in the business and sustaining the firm after he leaves. it is truly fascinating to watch and think about this factor as well as the ‘fall from grace’ or ego factor that is also operating beneath the surface with these types.

  5. Love this update. $5M salary is mind numbing. I am a CPA in Canada and I don’t think one of big 4 audit partners in Toronto make that much. Probably in the range of $400K-$1.5M at the most. Interesting!


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