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Told my SO when we had a reason to talk about it. He told me his salary when he got a new job. I told him mine when we started budgeting for a house. These events were 6 months and 10 months into the relationship. I otherwise didn’t want to flex my earnings earlier in the relationship.
I have only dated salaried employees and would have been very wary if we hadn't discussed salary by the one year mark (typically it comes up for me in the context of moving in together or going on trips).
However I understand why someone with passive income may feel more touchy about it since it fluctuates so much and he doesn't want to feel micromanaged.
Has he ever given you an idea of income range? I would want to get an idea of finances before moving in together or getting married.
My partner is also in a variable income career - commercial real estate. He is very open about what he makes both in good times and bad. He made >$400k the first two years we were together and made $65k last year. He was so ashamed about it and it was hard for him to talk about. Between savings and my income it’s not that big a deal and I try and reinforce that to him. He also sat around a lot more last year than I’ve ever seen him do in the past. There just wasn’t any work. I still have full faith that when the market comes back he will be back out there hustling. We live together and are engaged. We want to buy a house and have a family so we have to talk about money. I guess the only thing to do is try and create a safe space for you and your partner to talk about money. Make it less about how he is doing right now and more about preparing for future goals.
I think that is very caring that you were looking out for his well-being. I wouldn’t over think him feeling more guarded, as it could very much be an ego thing. If you have a reason to discuss, discuss, but that doesn’t seem to have a need so just continue to be caring and assume positive intent.
We’re both in Consulting (different firms) so we knew the range of what the other person made. Given that, we talked about it pretty early.
3 years is probably too long not to be talking about these things unless you’re very young.
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My SO and I talked about it around 8 months in & were both salaried. Now 2 years in, we know about each other’s net worth and investments. I would think that as you all start taking long term, eg life style, life goals, buying a house etc— it should be part of the conversation