I have two options - slightly disorganized, fast paced company where I’ll be busier and more nights and weekends, but probably doing more substantive work OR really organized, hierarchical company where I’ll have more time with my young kid but sending more to outside counsel and having less accountability for my work product (aka potentially losing competence). Comp is close to the same. Culture is more “intense” at first place and more “nice” and employee centric at the second place. Help me!!

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To me, the very obvious choice is #2

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Ditto.

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Easy choice is number 2 unless there are additional factors for number 1

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I have been in both environments and i think i may be like you - being in these bureaucratic slow paced orgs is stultifying like you predicted. A scrappy less rigid startup where people care more about doing a good job is a healthier more rewarding environment. But high chaos / low structure tend to correlate with management that doesn’t want to be told no and may treat people as more disposable. If you don’t want to be in job #2’s industry #1 may be worth it just be aware of the pitfalls and lack of stability.

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2. You always have the opportunity with 2 to proactively ask for more or ask to help on something that interests/challenges you.

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There’s also the ability to do pro-bono to keep your skills up!

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Option 1 is chaos. Do you need the chaos for some reason? Ability to move up, break into a new practice group, more $, still a young lawyer grinding out skills, etc?

Take option 2 and instead of leaving work at 3pm on a Friday do some CLE’s.

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I know some who were in-house their entire careers and are quite formidable attorneys. Most of the attorneys I know who went in-house early (as generalists) stagnated regardless of workload, often being glorified contract specialists.

The disorganized aspect is worrisome (but could be mitigated). Seems they don’t have enough help, which could be caused by business not appreciating the work Legal does, and correspondingly being tight-fisted.

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2

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#2!! what does comp look like and how many yoe?

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2

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I have young kids and have done both and #2 is the very very very obvious winner

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I'm sure each opportunity may vary, but I work at a stable company after a long firm life and I've never felt my skills stagnate. Admittedly, I am reluctant to send work outside and have the luxury to choose (budget-wise). Every opportunity is what you make of it. Nothing wrong with chaos, but if all things are equal (as you said), you can control the chaos and flex your law muscles far more with No. 2. With No. 1, you're going to be reacting more than making a strategy. If you want more challenges with No. 2, run towards the fire and create your own opportunities to grow your knowledge base.

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About to leave a company that is in chaos - I can assure you that I’ve been working on some work that even paralegals won’t touch - like renaming folders. The naming convention follows a spreadsheet that contains confidential information and my manager won’t let me delegate to my paralegal :/

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What??? Unless it’s a court filing marked AEO or a confidential “need to know only” trade secret type special sauce, my paralegal has access to it

You might want to ask this question in another bowl. This bowl is skewed in favor of those of us who will always choose better WLB.

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That’s a good point. Lol

Chaos is a ladder. Many who try to climb it fail and never get to try again. - Ancient Proverb

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“… the fall breaks them. And some are given the chance to climb but they refuse. They cling to the realm, or the gods, or love… illusions. Only the ladder is real, the climb is all there is.”

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There is a lot to learn by observing how others (lawyers & non-lawyers) do their jobs. Company No 2 may prefer to keep work in house to save $. You could impress them (& make yourself valuable) by learning the substantive work from outside counsel & then doing it yourself. I handle 90% of the legal work and only rely on outside counsel for certain work I don’t want to do. Your posting makes assumptions about the status quo at No. 2 and it’s use of outside counsel. I would explore that because you could have options for growth you don’t realize.

2 hands down. Life is too stressful.

You are describing my exact options at the moment!

2 seems like the obvious choice. You will never get this time back with your children. I know there is some aspect of "live to work" for us ambitious, professional ladies, but in retrospect, I would take more time with my children in a heartbeat.

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