Should I Get Married?

Step 1: The "Business Partner" Test

For a moment, take the romance out of it. If you were choosing a business partner with whom you would be legally and financially entangled for the rest of your life, would you choose this person? A marriage is, in many ways, a business partnership. You will share assets, debts, and make thousands of financial and logistical decisions together.

• Are they reliable and responsible? Do they do what they say they will do?

• Are they a good communicator? Can you have difficult conversations productively?

• Do you have a shared vision? Do you want the same things out of life, financially and personally?

• Do you trust their judgment? Do you respect the way they think and make decisions?

• Love is essential, but it is not enough. You must also be able to function as a team.

Step 2: The "Big 5" Compatibility Check

Most long-term conflicts in a marriage don't come from leaving the toilet seat up; they come from a fundamental misalignment on one of the "Big 5" areas of life. You must be on the same page with these before you get married.

• Children: Do you both want kids? If so, how many? What is your timeline? How do you envision raising them (religion, education, discipline)? What if you struggle with fertility?

• Money: How do you view the role of money? Are you a saver and they are a spender? How will you combine finances (or will you)? How will you make major financial decisions?

• Careers: How will you prioritize your two careers? If a major opportunity arises for one person that requires the other to sacrifice, how will you decide?

• Family: What role will your extended families play in your life? How will you split holidays? What boundaries will you set with in-laws?

• Location: Where do you want to live long-term? Do you share a vision for your home, city, and community?

Step 3: The Conflict Test

Every relationship is great when things are good. The true test of a partnership is how you handle conflict. A healthy conflict is a sign of a secure relationship where both partners feel safe enough to disagree. An unhealthy conflict is a sign of deep-seated issues.

Think about your last major disagreement. Did you use the Four Horsemen (Criticism, Contempt, Defensiveness, Stonewalling)? Or were you able to:

• Listen to each other's perspective without interrupting?

• Acknowledge your partner's feelings, even if you disagreed with their point?

• Take responsibility for your part in the conflict?

• Work towards a compromise or solution, rather than trying to "win" the argument?

• If you cannot fight constructively, you are not ready for marriage.

Step 4: The "Good Enough" Partner (Inversion)

The search for a "perfect" partner is a recipe for misery. A better mental model is to look for a "good enough" partner. Using Inversion, instead of listing all the things you want in a spouse, list the absolute deal-breakers you cannot tolerate.

What are your non-negotiables? Is it a lack of ambition? A history of infidelity? A fundamental difference in values? Write them down. Does your partner exhibit any of these deal-breakers? If not, they may be "good enough." A successful marriage is not about finding a perfect person, but about building a life with an imperfect person whose flaws you can tolerate.

Step 5: The Pre-Mortem - Why Would This Marriage Fail?

Before you commit, imagine the worst-case scenario. Use the Pre-Mortem mental model: It’s five years after your wedding, and you are getting a divorce. What happened? What were the most likely causes of the failure?

Was it a slow drift apart? A recurring conflict that was never solved? A betrayal of trust? Financial stress? By identifying the most likely failure points before they happen, you can either address them now or accept them as risks you are willing to take. This exercise moves you from romantic fantasy to a clear-eyed assessment of the real risks involved.