Check Your Three Boxes: The Strategy for Every Big Decision

Looking for a new job or a new city? Stop guessing. Use the Three Boxes method to rank what actually matters and make decisions with total confidence

By Your Bro · · Self Improvement

Check Your Three Boxes: The Strategy for Every Big Decision

Making a life-changing decision while you’re emotional is a great way to wake up six months from now wondering why your life feels like a dumpster fire.

Key Takeaways

  • All major life decisions can be distilled into a checklist of desirable outcomes.
  • The "Perfect Opportunity" is a myth; aim for your top three non-negotiables.
  • Ranking your boxes objectively removes the emotional fog that leads to bad choices.
  • If a deal doesn't check the Big Three, walk away before you hit the point of no return.

The Psychology of the Big Decision

Looking for a new job? Thinking about asking the girl you're seeing to be exclusive? Considering a move to a new city? No matter what the "big decision" is, it's always important to weigh the pros and cons so you know what you're getting yourself into and feel comfortable with your decision. Most men fail here because they lead with their gut, and their gut is often just hungry or lonely.

This is why I tell many young men they need to ensure the decision "checks their three boxes." But wait, what boxes? Think of your desires for any situation as a checklist. Without a written list, your brain will prioritize whatever felt most urgent this morning. If you just got a parking ticket, your "box" might suddenly become a higher salary, even if that job has a boss who treats humans like disposable batteries. I've seen guys tackle problems head on only to realize they were running in the wrong direction because they didn't define the goal line first.

Identify Your Ten Potential Boxes

If you were looking for a job, what would you want out of it? You need to brain-dump every possible factor before you can find the ones that matter. In a typical career move, your list might look like this:

Every once in awhile, the job you find will check every box, but the odds of that happening are small. According to Pew Research Center, only about half of U.S. workers say they are extremely or very satisfied with their job overall. If you’re holding out for ten out of ten, you’re going to be unemployed for a long time. You have to be realistic. Most situations are not perfect, so while seven of your boxes may be checked, three might go completely unchecked. That's okay, as long as your "big three" boxes are checked.

Ranking the Values

A really valuable exercise to run through while considering an important decision is actually ranking the value of these ten boxes. Evaluate which are absolutely necessary versus which are "nice to have," and put them in that specific order. This is where you find out who you actually are. Are you the guy who needs the money, or the guy who needs the lifestyle?

For example, if you're a very competitive person that is highly motivated by making money, you may rank these boxes in the following way:

  1. Specific salary
  2. Competitive bonus / equity structure
  3. Ability to advance
  4. Boss you can learn from
  5. Chance to expand network
  6. Strong benefits
  7. Opportunity to travel
  8. The actual work is interesting
  9. Great culture
  10. Short commute

Once you have this list, the noise disappears. It doesn't matter if the office has a Ping-Pong table or free snacks if the salary (Box 1) and the bonus (Box 2) aren't there. You stop being distracted by the shiny objects. This applies to your social life too. When you keep your circle small, you do it because those people check the boxes of loyalty and growth, not just because they’re fun at a bar.

Analyzing the Matchup

You could be considering two job offers, so running through this exercise will help you drill down to the most important factors and make the best decision possible. After you've ranked your top three categories, compare the two opportunities to ensure both do check those boxes. It might be an easy, clear-cut decision if one does and the other falls short. However, if both fulfill your top three needs, you have two ways of analyzing this further: Weigh your top three boxes for each opportunity to see which offer is stronger, or consider boxes four and five to determine which is a more well-rounded opportunity.

Let's look at a head-to-head comparison between two fictional companies, Marvel and DC:

Option 1) Weigh the boxes:

Option 2) Most well rounded:

The Danger of Haste

I once had a friend who was offered a "dream job" in a city he hated. He didn't check his boxes. He saw the title and the pay raise and signed the contract in forty-eight hours. Within three months, he was miserable because he realized his number one box was actually being near his family. He spent a year's salary on a therapist trying to figure out why he was depressed in a corner office.

Remember, all big decisions should be thoroughly analyzed before the choice is made. You should never do this in haste, and anyone that pressures you to decide too quickly doesn't have your best interests in mind. Research from the American Psychological Association notes that stress-induced decision making often leads to focusing on short-term gains while ignoring long-term consequences. Take your time and fully understand what you're getting yourself into before making the big move. If they won't give you forty-eight hours to think, they're probably hiding something. You aren't a hostage; you're a man making a trade. You should also make sure you have the skills to back up the demands of whichever box you choose to pursue.

What To Do This Week

  1. Write down the top ten things you want from your current "big decision" (job, move, relationship).
  2. Force yourself to rank them from 1 to 10. No ties allowed.
  3. Identify your "Big Three"—these are your non-negotiables.
  4. Review your current options against those top three. If an option doesn't hit at least two, throw it out.

Good luck out there.

—Your Bro