John D. Spooner is an investment adviser, author and novelist. His most recent book is No One Ever Told Us That: Money and Life Lessons for Young Adults. Here, he responds to queries from advice seekers of all ages. Send your conundrums to

I was recently promoted to a new position and have been tasked with hiring a new staffer—something I’ve never done before. I’ve seen things go awry in other departments with hires who looked good on paper but turned out to be really difficult to work with or who didn’t pull their weight. Any advice for what to ask a candidate during an interview to get at the important but less quantifiable stuff that’s not on the resume? In this arena, I like to ask unusual questions that can get beneath the surface of the real person you’re interviewing. Too often, the discussion about previous job experience and supposed qualifications produces vanilla answers that sound forced and rehearsed. You want spontaneous reactions, from questions that explore their real personalities.

I’m in the money management business. But it’s really the people business. I like to hire folks who can work both sides of the brain, the practical and the creative. I ask potential hires about their hobbies and interests. I ask them what they majored in at college. I ask them if they have a big dream for themselves. I ask them, “What’s your all-time favorite book and your all-time favorite movie?” The answers to that question can tell me a lot about their character. And if they don’t read, or don’t have an answer, they probably will never work for me. I try to probe candidates for three main qualities: curiosity, people skills and a sense of humor. We can teach the basics and the mechanics. They have to come to work having my three requirements for working in a people business. So many people pad their resumes with boilerplate stuff. In my experience, the candidate’s hobbies and passions are the true measures of their character and their value to your organization.

Do you think it’s ever OK to quit a job without having a new one lined up? Asking for a friend. The best case would always be to find the new job before you quit the old. But life is never perfect, except for those brief shining moments that never last.

Quitting a job these days, unless you have an unusual skill, is tricky. Millennials, good for them, are very portable, bouncing from job to job. But money does matter, particularly in this hyper-narcissistic society. I talk weekly to so many young people, and a young man in the ad business recently said to me, “We throw ourselves into adventures. But we really live paycheck to paycheck.”

If you hate your job and it hurts your belly and your soul when you show up every day, then quit. If it’s tolerable, then suck it up while you look actively elsewhere. You want that cash flow.

But before you hit 30, realize that you cannot play the gypsy game forever. At some point you have to make a stand and say to yourself, “I can see a really good future here.”

I know that your generation so often says, “Eventually, I want to work for myself.” That’s fine. But my sense is it’s a knee-jerk answer, not thought out. At 25 and beyond, start working on a real plan, not a fantasy. And realize that you may have to work your tail off to achieve it.

I recently snagged the cutest apartment in the city. Love it. Great location, great amenities. My question is, is it worth it to me to keep my car? I can take the subway to work, but I fear losing the freedom of having a car of my own. Like on weekends, I would like to travel to see friends, family, or take trips to the Cape or something. Is it worth it to keep my insurance up even if I only drive on weekends? This great apartment does not include parking, unfortunately. This is an easy one. Americans, since the first black Ford Model T rolled off the assembly line in 1908, have been in total love with our automobiles. The biggest reason for the guys was that the cars represented freedom: where you could take girls. Now the revolutions caused by the digital age include dumping our cars and using Uber and Lyft. If you live in the city, dump your car; it’s a no-brainer. The money you’ll save on insurance, parking and aggravation will set you free in many ways. We’re a walking city. For your forays out of town, it’s easy to rent a car, much more efficient and, in many ways, liberating.

The exception: If you just inherited a pile of dough, buy a Tesla or anything you want. Then try to buy a parking space at the Brimmer Street Garage. It will make you understand supply and demand. Parking spots are at a premium on Beacon Hill, and you are currently looking at the possibility of a $500,000 price for a space to park your car. There is an old saying, supposed wisdom: “Anything that flies, floats or f_ _ _ s, you should always rent, not buy.”

Enjoy the apartment. Rent your rides.


Related Articles

Comments are closed.