November 2018

Transitioning to Litigation as a Transactional Attorney: It’s Not (That) Bad

By Lauren Hanley-Brady

Global Legal Law Firm, LLP

As the title would suggest, this article is about my experiences in switching from transactional law to litigation. First, a little background: I’m an introvert, I majored in film production specifically because I didn’t want to be in front of the camera, and in law school I did everything in my power to avoid litigation-related courses and events. All my law electives encompassed contract drafting, licensing, and the necessities for brand management. I never wanted to do litigation.

Fast forward to two years into my work as an attorney doing all of the above, wherein I realized I wanted more direct mentoring than what I had access to. While I enjoyed the work my clients brought me, as well as working remotely on projects for more experienced attorneys, I missed having the structure of an office with other professionals with whom to talk and bounce ideas around. I was also encountering in my practice questions dealing with potentially sticky employment situations, and I wanted to learn more about employment law so I could apply it to my work.

Enter: the employment litigation job at a small firm.

I wasn’t looking for a job in litigation — I really wasn’t. However, the position offered me the opportunity for me to be given a lot of case responsibility and autonomy right off the bat, as well as second chairing within a year (for anyone unfamiliar with trials, that’s the other seat, next to the main attorney, that you see on t.v.). I started at the end of a January, and second chaired my first trial in August of that year, with my second trial — a two-week jury trial—that October. Trial by fire, as it were.

But what was it like? The things I feared the most about litigation were (1) court appearances, and (2) drafting motions. I’d drafted a single motion in law school, and I’m glad I don’t have a copy of it now because I’d probably die of embarrassment. I just didn’t “get” them. Contracts were my passion: they made sense, they had a structure, and it was all about finding the best clauses out there to cobble together a patchwork-quilt-contract perfectly tailored for my clients’ needs. I loved making order out of chaos.

Well, litigation is chaos, so at least I’m never bored.

When I started my first litigation position, my supervising attorney knew I had no experience in this area, but he also knew I could write well and assumed I’d figure things out. With perhaps a little too much trust, he threw me a petition for writ of mandate as my first major assignment. I said, “Sure, boss,” and immediately Googled what the hell it was. Eventually, I realized that working in litigation is a lot like transactional work because you’re often looking for samples so as to avoid reinventing the wheel, but also assessing whether what you’re reading is a good example or a wrong one. You don’t always nail it, but that’s why they teach us to “think like lawyers.”

After that first project, I was immediately thrown several motions and oppositions to draft, as well as discovery responses — none of which I’d ever done before. Thankfully, I had other attorneys at the firm whom I could bug, and they were generous with their time as I muddled through the weeds to find my feet.

Fast forward to my fourth year as an attorney: I’m working at a great firm with six other attorneys, support staff, and I’m in charge of an entire department of litigation for clients in the e-payment industry. I also assist with complex cases in all sorts of areas such as employment law, franchise law, and others, and I’m finally getting to use my Washington license. Oof, if you think it’s challenging to learn how to litigate in a state where you attended law school, imagine the fun we’re having figuring out how to do it in another state entirely! By the way, the legal profession isn’t downplaying it a single bit to say that ‘every state’s laws are different.’

The Good:

Litigation is very intellectually stimulating. Note that ‘intellectually stimulating’ and working in your ‘passion’ area(s) of law are not always the same. For instance, I am not at all passionate about bankruptcy law or whether non-payment of a final paycheck constitutes conversion (common law) or is preempted by the Labor Code (statutory). But, that doesn’t mean I don’t find it interesting to learn about bankruptcy procedure from a practical, on-the-front-lines point of view or delving into research on court disagreements at a granular level so as to draft a compelling appeal to the State Supreme Court.

The work is challenging, and the sense of accomplishment when you’re done is rewarding, even if you don’t always win every argument. Plus, litigation truly hones your ability to think quickly, negotiate well, and handle a large load of work and responsibility without letting any of the balls drop (ideally).

The Bad:

Long hours seems like kind of a cop-out for this heading. Obviously, the hours are a downside to litigation, although they’re not always so long. That said, in trial prep, I had several instances of 70-80-hour weeks, and I didn’t work nearly as long as my supervising attorney. I’ll admit that there were days when I questioned my choices, my sanity, and had somewhat morbid thoughts, in those late hours, like if I died right then, my last day would’ve been spent without experiencing a single moment of genuine happiness, let alone doing a task for myself that furthered my interests as an individual.

Since ‘long hours’ is a given in litigation, the second runner up for ‘the bad’ is … … DISCOVERY. It’s like running barefoot on a treadmill covered in Legos. Not only do you feel like you’re not getting anywhere, despite putting in a lot of effort, it also hurts the whole time you’re doing it. No one likes discovery. If they say they do, they’re either lying or they’re crazy and you should hire them immediately, so you never have to do it.

Finally, for those who think appearing in court is terrifying, it’s kind of like drinking wine: no one enjoys it the first few times you try it, but if you drink it often enough, you get a taste for it and may even come to enjoy it. Then again, you might always hate it, but you grin and gulp it down because #adulting. I’m not quite at the ‘enjoying it’ stage, but I no longer get sweaty palms every time I do a Court Call or ex parte.

The Ugly:

There is most certainly a darker side to litigation that is a sad fact for litigators: when you sue people, they often (and understandably) are very angry at you. Shocker, I know. Sometimes people retaliate by attacking your reputation or keying your car. I’d wager this happens more often in family law than general litigation, but there are those individuals out there who take it upon themselves to punish you because they don’t like what your firm is doing to them. It is what it is. You can’t control them or what they do, but you can control what you do and how you react. If you do good work, people will see that and respect it.


There is a lot of crossover between transactional law and litigation — my law professors told me that, but because I couldn’t comprehend the mystery that was litigation, I didn’t dwell on it and I just tried to draft the best contracts I could while trying to anticipate all the potential loopholes.

Well, in litigation, you not only see where those loopholes weren’t closed, you sometimes also find yourself in a position where you know there are loopholes, but you can’t close for various reasons, so you have to think creatively and work in Band-Aid provisions that will at least help you to litigate the agreement later on, if it comes to that.

I believe I’m a much better drafter of contracts now that I’ve seen so many ways in which they can be breached or are poorly (and vaguely) drafted. I know that the skills I’ve learned in litigation will bolster my skills in transactional law, should I return (eventually). If you’ve ever wondered what it’s like, and whether you’d be cut out for it — remember: you can do anything for an hour. There were days where that mentality was all that got me through the tough deadlines, and eventually the ‘hour’ turned into a day, then a week, month, etc.

Litigation might seem scary, and it is definitely stressful at times, but it might just be the intellectual challenge you never knew you needed.