I have a good marriage.

I got lucky in love and have been enjoying it for 22 years.

Part of the reason it works is that I married later in life (33). We both finished school and started our careers before we met.  Already, we were growing into the people we are today.

We are also solid because we had tough conversations before taking the plunge. Some of them were best sober, some better with a bottle.

How do you ask hard questions to the person you are about to spend the rest of your life?

Simply, directly, and then wait patiently for an honest answer.

Here is a list of career conversation starters. Some of them could be more pleasant. Some will challenge your significant other in the most personal way. It will make them think about the way they were raised. It makes them wonder if their parents are right or wrong. Will force them to look at their core and to stare into yours.

Either way, these conversations need to be had.

What influence do each of our parents, siblings, and friends have on our career decisions?
Their advice is undoubtedly welcome and may be valuable. However, that is where it should end. The decision is ours.

What happens if I am more successful than you?
Will you see this as our success, or will you feel ashamed that your time has not come yet?

What happens if the job of a lifetime surfaces for one of us outside of where we are living now?
Consider where you grew up, went to school, where your family and friends are based, and the big one – if you have children. Can both of us pick up and go if something amazing surfaces? Perhaps one of you has spent your whole life in a city (including college), and now you want them to move across the country.

What happens if one of us has a sensational job but the travel or commute is heavy?
Is the other independent enough to manage and willing to shoulder the load while the other is away?

Would either of us be willing to stay home and raise our child if that is the home/lifestyle we want?
Thankfully, it has become more prevalent that men are taking time off to start a family. However, the stigma continues in some families.

What if your wife/partner makes double what you make?
Could you look your friends/family in the eye and tell them you will be a stay-at-home dad/mom?

Are we okay with each of us returning to work after childbirth?
This changes after your baby is born. Something biological happens to both of your emotions, and this decision is not as direct as initially thought.

What if one of us has a sensational career in an industry that upends the other?
Would we be comfortable making a great living in that dynamic?

What about risk? Are you okay with me taking chances, going to a startup, returning to get a Master’s degree, leaving a role I hate without another job, etc?

What happens if we take a risk and it does not work out?
Will you hold that against our next decision? Will your trust in me diminish?

What if I had the job I had gone to school for, and after ten years, I did not want to do it anymore?
This happens to dozens of professions.

Several more questions warrant further discussion. Think of ones that are more pertinent to your situation. Whatever they are, bring them up. Talk about it. Find a good time when both of you are in a place where you can receive information like this with an open mind.  Ask your significant other if they are open to a candid and important conversation.

Be a good listener. Hear them out, no matter how much you may disagree, if they have changed their mind on something or have been withholding their feelings from you. 

It is worth it.  It is not supposed to be easy.  Nothing important is…