Paint jobs, paperwork and boxed-up problems

Dear Rachel,

Our summer project is repainting the house. Or, having it repainted – we’re not that youthful anymore. My husband is insistent that anyone we hire be licensed, bonded and insured. I just want it applied without drips. Do you think I’m being too laissez faire? Or is he being too by-the-book?

– Spruced Up

Dear Fresh Coat,

I semi-glossed over the details of home maintenance class in high school. Oh wait, we didn’t get that class in high school. We should have; it would have helped me argue with landlords way better than my French class in which I didn’t actually learn any French. I think it doesn’t ultimately matter who you hire to slap some Sherwin Williams on your walls. You’re just painting over your problems. Skimp on the painter and invest in a different kind of professional to get to the undercoat of what really matters.

– Pantone perfect, Rachel

Dear Rachel,

No one ever told me that all the paperwork for starting a new business was so expensive, from filing LLCs to business licenses to trademarks to all kinds of junk. I expected to spend money on stuff to sell but not to go so far in the hole on other people bleeding me dry. What the crap? How does anyone start a business without already being wealthy?

– In the Red

Dear In the Hole,

You wanna know how they do it? Under the table, my dude. You pretend you didn’t know about all those pesky rules and regulations, and you take cash, and you wait for a city enforcement officer to come knock on your door, at which point you run out the back with your bag of cash and start over again in a new city, like Bayfield. At least that’s how my uncle did it. We haven’t heard from him in 20 years, though, so think carefully. Entrepreneurship is not right for everyone.

– On the Lam, Rachel

Dear Rachel,

I thought new shelving would change my life. Like my home and soul would transform from mismatched stacks of cardboard boxes to well-stored rows of mismatched cardboard boxes. It turns out I can’t fit all my problems on a shelf, and I’m still the same jumbled wreck inside. What should I try next?

– Top Shelf Problems

Dear High-Grade Storage,

If I could afford to hire someone to clean my house, I’d presumably be less internally cluttered, and wouldn’t have to read deep emotional struggles into everyone else’s superficial complaints. Until we’re rich, though, I think we have to keep boxing up our problems. And then maybe paint over the boxes. Because why not?

– Taped shut, Rachel