David Herz, Coach

Is marriage a bad idea if your boyfriend is struggling to generate a consistent source of income as an entrepreneur and you're also in a long-distance relationship?

They are not connected. Do you love each other? Are you both willing to be great with each other? Are you both willing to support each other as you are building your dreams?

It might be a harder road than picking the guy with the good job and steady income next door (that might not last either), but wouldn’t it be a better adventure to share, and wouldn't you be happier knowing you picked a partner with whom you could take on anything and keep going until you win?

Of course, it would also take that kind of commitment. Ask him if he's willing to play that game. Ask yourself if you are willing to play that game.

If the answer is yes to those, you've got a good chance with him.

Asked on Quora:

Should I support my musician boyfriend pursue his dreams while he depends on me financially completely? He has been trying for about 6 years.

No. You should tell him to get a damned job and pursue his music on the side.

It's time to stop trying and start doing. And when he takes on his job, he should take on doing it with excellence.

And then, especially if he hates his job, tell him to double down on his music. Work full time at his job, and work full-time at his music, with the same damned intensity.

Then he'll know if he really wants his music, or just likes calling himself a musician.

And don't let him get away with just practicing. A musician performs. Make sure he's booking at least one gig a week, and giving it his all.

But don't you dare suffer for his art. If he wants to suffer for his art, that's great. You can drive him to his gigs, be his sound engineer if you want, and be his biggest fan, but he's got to take on being the damned artist.

Recently Asked on Quora

How do you become your own best friend?

This is a bad idea. While you should have self-respect and a healthy view of your potential/ability, as your own best friend you are talking into an echo chamber that will only confirm and grow your biases.

You want a critical outside party to give you a good smack upside the head when you need it, a hug when you need it, a shoulder to cry on, and even a pity party from time to time, followed with a smack upside the head. You can try to be this for yourself, but it's too easy to uncritically fall into bad patterns.

What's more, you live in the world. You must learn to navigate that world. Instead of looking inside, you might want to engage in a much more fun question: “What can I do today to be the World's Best Friend?” or “What can I do to be X's Best Friend today?” where X is any person you want to connect with today.

There are two things I want to add here. The first is the best way to have friends is to be a friend. A friend does without any expectation of return or profit. He does because he has a commitment and it makes him feel good.

Second, it's not for you to judge if you are a good enough friend. If a person says you are, you are. That doesn't oblige you to anything, other than the baseline honesty and straightness that should be there anyway.

Take it on. If you want you can make it your theme for 2018. And if you are so inclined, come on back here and let me know how it went.

Dear Friend:

I write to ask your forgiveness. And I thank G-d that you are so much more grown up than I.

You said on Wednesday that you get angry. I could only think that you got that from me, and that's really not the legacy I want to leave you. It's not a happy - or productive - way to go through life.

I interviewed a friend of mine a few weeks ago. And then got to speaking with him about parenting afterward. He shared the major lesson he left his kid: “Just keep going.”

I missed that one somewhere. Every time I thought I made a mistake, every time things didn't go as planned, every opportunity I've missed, I let it mess me up. With all the Landmark I've done, you'd think I'd be past it (instead, I use it as more evidence that I am screwed up).

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Jakob Owens

My fiance says I stress him out and he needs space but does not want to break up. He booked an Airbnb for 3 weeks and has blocked my number. What should I do?

First, you should complete what was. You don't need to get married just because you invested all this time in a relationship.

Let's start with, knowing everything you do about him, would you still choose him if you only met him today?

If no, stop reading and end it. If yes, keep going.

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