Eating a Whale: Best Practices to Tackle Tough Problems

by | Jan 18, 2020 | Business Law, Real Estate Law

Best Practices to Tackle Tough Problems

When clients are confronted with a complex legal problem that has a lot of moving parts, it can be difficult for them to “see the forest through the trees”. I offer clients overwhelmed by a complicated real estate or finance problem the following five items to consider so they can effectively tackle their source of stress.

Get Organized

Staring at a pile of miscellaneous documents can weigh on one’s morale and motivation. Sort important paperwork in manila folders. For example, organize papers by a vendor, antagonist, date, subject or concern, contract, loan(s) or lease(s). You’ll feel better once you’re organized and you’ll help your advisors address the problem more quickly.

Define the “What”, “When” and “How”

Complex matters often have a series of tangled and interrelated problems. Write down all the problems that present themselves in a particular situation. Then, define how you intend to solve each problem. There may be several ways to approach each problem. List them. Ask yourself, “what can I do to create any movement that will make me happy with my progress?” Now, realistically define the time frame that you expect to address and be done with the problem.


Resolving complex problems requires one to prioritize each step or action necessary for a resolution. Prioritize and strategize what has to occur first before you can move ahead to the next task.

Don’t Make Quick Decisions

Never let anyone, particularly the antagonist in your situation, push you into deciding. Consider the “24 Hour Rule”. Take 24 hours to weigh the pros and cons of a decision. Remember, complex problems take time to create. So, take time to think about the consequences of a decision.

Give Yourself a Break

Ruminating about a problem 24/7 does not solve the problem. In fact, it can stress your physical and mental health. Think about all of the good decisions that you have made in the past under stress. Eat well, rest, and exercise for a clear head. A mentor once told me that successful problem-solving is like eating a whale–you have to eat it one bite at a time. Envision setting a table to feast on your problem. Calmly organize your documents, define the problem(s), and prioritize your proposed solutions using realistic time frames that will make you happy with your progress.


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