Extracted from Law360
Ever since I was a little kid, fishing has been a part of my life. My father taught me how to fish at a young age, and it sparked a lifelong obsession. I grew up on Long Island, and the opportunity to fish from land or by boat was ever-present.
One of the things fishing has taught me is how to be a better transactional attorney. Believe it or not, fishing has taught me a boatload of lessons about the work I do — pun shamelessly intended.
Closing a deal is like catching a trophy striped bass. The skills required are similar. Catching a trophy striper requires efficient problem-solving, preparation, adaptability and patience.
Let's take a look at how these attributes translate into the skills needed to close large deals as a transactional attorney.
Problem-Solving
At their cores, both fishing and closing a large transaction are problem-solving activities. And to be a successful problem-solver, a certain set of skills is needed.
Fishing boils down to one basic problem: how to get a fish to bite and swallow the hook. To solve that problem, anglers must come up with creative solutions to make the bait look as natural as possible. Of course, there are a number of other problems anglers must solve on any given outing: Unfavorable sea conditions, trouble finding the fish and dealing with nontargeted species can all arise.
Transactional practice is also a problem-solving activity. The goal of a transactional attorney is to close the deal without overlawyering, while also getting the best possible outcome for your client.
Additionally, just like fishing, a number of other problems may present themselves during the course of a deal. For example, details may be uncovered that present a potential roadblock, interest rates may change quickly and deal structures may not dovetail well with the intended goal of the transaction.
As a transactional attorney, it's imperative that you have a problem-solving mindset. A good transactional attorney is always thinking about efficiently achieving the client's goal while minimizing time spent on the deal. As is the case with fishing, sometimes transactional practice requires deal attorneys to be a bit creative. Whether I'm acting as a borrower's or lender's counsel in the world of structured finance, fishing has helped me become the attorney that I am today.
The Importance of Preparation
Anglers need to be ready at the drop of a hat when the news of a blitz makes its way over the VHF radio. Translated to deal terms, when the deal is on, it's on.
As a transactional attorney, the same tenets apply: When you're in the midst of a complex negotiation or deal structuring, you need to be prepared for whatever facts and circumstances are thrown your way that can upend the structure. Preparation ensures that when an emergency materializes, you're ready to jump in without having to play catch-up.
I look at the term sheet phase of the deal as though I am preparing for the fishing season. Are my rods spooled correctly? Do I have the right lures ready to go? Are my knots secure and tight? In the term sheet phase, I'm asking similar questions as a way to get a better understanding of how the deal will be structured and what potential issues might arise as we begin drafting documents.
Just like how each striped bass outing is different, so too is each deal I work on. The blueprint may share similarities, but there are always tweaks that need to be made, especially midway through the negotiation process. Preparing in advance makes life easier once you encounter the inevitable snag.
Additionally, preparation reduces the chance that you will suffer from decision fatigue. Striper fishing is typically done in the cold, rough ocean waters in the fall. Conditions on the water are often suboptimal, and decision fatigue can be real during an outing. Being prepared reduces the risk that you will throw in the towel early because you made the wrong choice of lure or fishing spot.
This is also true of contract negotiation. Tensions can be high. Preparation does a bit to belay this concern and allows you to focus on the work needed to get to closing.
Second-guessing your choices during the course of a deal will render your work ineffective. It's easy to get lost in the details and question decisions; however, as lawyers, we need to also take the big picture into consideration. Planning ahead reduces the risk of making this mistake.
Adaptability
Another aspect of striper fishing that translates well into working on deals is the ability to change course during a trip.
In fishing, adaptability is the key to keeping your rods bent. Stripers are notoriously picky eaters. In fact, they are so picky that they can limit their feeding to specific times based on when the tide changes. The ability to understand the bait profile and whether you're applying it correctly is key to success.
Just as in structuring a deal, attorneys need to be able to change course if a transaction starts to take on a different form or new facts come to light that were not present at the term sheet phase. This means attorneys must be ever-mindful of the changing nature of a specific deal. Much of this is driven by your clients' wishes. Lawyering in this type of atmosphere requires a bit of creativity and outside-the-box thinking.
Patience and Discipline
It probably goes without saying, but any type of fishing requires some sort of patience and discipline. Patience is not passive — it's strategic.
Experienced anglers know that patience is active. Many times, an angler just needs to wait patiently before hooking up. There have been numerous outings where I decided to make one more drift even though I was ready to throw in the towel and limp back to the dock. That drift or cast would prove to be the winner.
In high-stakes transactional work, patience is also a must. Not every issue needs to be litigated in real time. Sometimes, the best move is to wait, gather information and let leverage develop organically. Restraint, whether on the water or in a negotiation, is a skill learned through discipline.
Dealing With Loss
Every angler loses fish. It's just part of the process. Hooks pull. Lines snap. Rocks win. As an angler, you analyze what went wrong, retie and get back out there.
The same resilience is essential in transactional practice. Deals fall apart. Terms you fought for don't make the final draft. The lesson fishing teaches is to avoid emotional spirals. You learn to diagnose, adjust and move forward without ego. That mindset makes you steadier, clearer and ultimately more effective for clients.
Fishing teaches you that loss is just part of the process. Not every deal is going to be smooth sailing. Getting skunked — slang for not catching fish — is hard, but learning why you got skunked is essential to becoming a better angler. In transactional work, the more reps you get, the better the lawyer you become.
At work, there are days when the negotiation doesn't go as planned. In those instances, I remember the many times I've been skunked out on the water. Even though I don't have a story to tell after those trips, I still keep coming back for more. Persistence is key in both activities.
Don't Horse It
A common line you'll hear from your fellow anglers when you've hooked a fish is "don't horse it." It means not to put too much pressure on a fish during the fight. When a striper is on, an angler needs to resist the urge to reel incessantly or put undue tension on the line.
Stripers need to be finessed to the top water. That means adjusting the drag on the reel and letting the fish swim away. Sure, you lose ground, but that eventually tires the fish out. It also prevents the line from snapping or the hook from pulling.
Transactional law rewards the same approach. Forcing a position rarely produces an optimal outcome. Rather than being rigid in your representation of the client, you need to find a solution that makes both sides happy. That requires finesse. Guiding a deal to shore, rather than dragging it, preserves value and relationships.
Conclusion
Over the years, fishing for striped bass has taught me a lot about what it means to be a great transactional attorney. In the end, striped bass fishing keeps me grounded. It reminds me that success comes from observation, patience, adaptability and respect for forces larger than myself. When I return to my desk — cold, tired and salt-stained — I'm a better transactional lawyer for it.
As we say in the fishing community, "tight lines!"