DEAR NATALIE: My roommate recently lost their job and it was devastating for them. This was about six weeks ago and they’ve been super depressed. The problem is, they were late on rent last month – which I understand considering the circumstances – but told me again this month they will probably be “short” and wanted to know if I could cover the rent until they get a job. Normally, I would be OK with this, but they aren’t even attempting to look for another job. I don’t want to upset them further, but if they can’t pay rent, they need to move back home or something. Should I give them another month to wallow or do I show some tough love? I care about them. We’ve been friends for a long time and roommates for a few years — and it’s easy to live together. Any thoughts on what to do? – ROOMMATE DRAMA DEAR ROOMMATE DRAMA: It’s time for some real talk with your roommate. It is important they know that while you want to be supportive of the situation, unfortunately, landlords aren’t so understanding. While you were able to float them last month, you may not be able to do so month after month – which is totally reasonable – and they need to pull their weight financially. Ask them if they need help working on their resume or if they need a “push” getting back out there. Can you help them network or look for a new job? Present this as an issue that is now impacting the whole household. While you want to be there for them, you can’t put your own finances on the line. This may be jarring for them, but it may be what they need to hear. It’s always rough to lose a job. No one is discounting that. And if you don’t have any kind of severance, it can be extremely scary. But the only way forward is through. Hopefully, with your support and gentle nudge, they can get back out there. And if they can’t? You may have to find a new roommate – and I hope it doesn’t come to that for everyone’s sake.
DEAR NATALIE: Friends are constantly coming to me with new business ideas. I think it’s a lot of fun to workshop ideas with them, identify problems and consider issues that can be solved with entrepreneurial projects. I have a lot of enthusiasm, but not as many hours in the day. In my head, I’m always thinking about things like these and wondering where to invest my time. I also don’t want to seem like I’m leading people on – if I followed up on every idea I talked about I wouldn’t have any energy left. How can I get realistic with myself about which projects to pursue? How can I use this part of my personality to benefit me financially? I definitely don’t want to charge my friends a rate for talking things out with me, but I don’t know where these boundaries should be. It’s like I’m a therapist giving out free therapy to my friends, but I do enjoy it. What should I do? – SEND HELP
DEAR SEND HELP: Sit down and get organized. What were the two ideas that your friends have proposed to you that made you feel the most energized? Which ideas would utilize your skill set best? Which ideas would stretch you slightly out of your comfort zone? Put each idea on paper and list those categories under each. Whichever checks all three… focus your attention on that one. Once you have a project under your belt that you saw through to fruition, then you could leverage that idea and start to consult with other people on their projects. Slowly build up a few successes and then create a simple website that shares those case studies for others to see. Yes, it is fun to be creative with our friends and brainstorm. There’s nothing wrong with giving friendly advice! But, if you want to make money with your ideas, you have to get serious about narrowing things down, honing in your focus and funneling your time and attention into one thing. It’s exciting to think of the potential of so many ideas – but when you actually create something into being? It’s magic.
Please send your questions to Natalie Bencivenga to
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