If there isn’t one problem that’s clearly the most dangerous, or is causing the most pain or difficulty, I suggest you look to see if there’s one fundamental or keystone problem all the others rest on. For example, if all your financial problems stem from your spending too much money on luxury items, begin by stopping your discretionary spending. Even if that is the most difficult problem in the cluster, it makes sense to tackle it first, because solving it may result in the other problems vanishing or shrinking dramatically.

Finally, if there’s no clear trigger problem, no problem that’s clearly the most threatening, and no keystone problem all the others rest on, I suggest you start by working on the easiest problem. Since you already perceive it to be the easiest, you’ll be less likely to procrastinate. And if it really is the easiest, you’ll solve it quickly and, as a result, boost your confidence for tackling the next one.

Once I had a chance to go over the cluster of problems facing Ken and Mary Schoenfeld, we decided to tackle their spending problems first. I believed their overspending held the most potential danger. It was also, actually, the easiest to solve, since it was totally in their control. Ken and Mary didn’t see it that way, however.

We began by having Ken and Mary keep a month-long record of every penny they spent. I then asked them to swear off using their credit cards and to instead pay cash or write a check for all their expenses. That added an element of awareness and perhaps even pain to each purchase. I gave them some consumer-oriented books so they could learn some shopping skills. Whenever they balked I told them to take a look at their two daughters and ask themselves if they’d rather spend the $14 on them or a gourmet sandwich. While Ken and Mary were never going to become ascetics they stopped being wastrels.

Text we examined their child care situation because we agreed that it was now their most pressing problem. Since there was no acceptable and affordable day care in their area, and since Mary couldn’t work and care for both girls, the choice came down to hiring a full-time nanny or Mary giving up her career temporarily. After some preliminary investigations it was clear that Mary made far more than was needed to pay for an acceptable nanny. Besides, Mary didn’t want to give up her career, even temporarily. She and Ken believed, and I came to agree with them, that if she was out of the business for even as short as three years she would have to start over from scratch.

With a nanny on the way, Ken and Mary had to examine their real estate situation. They needed more space, but a larger loft in the same or a similar Manhattan neighborhood was more than they could afford. After looking at homes in the suburbs, and investigating buying a smaller apartment while also renting studio space for Mary, they decided to make some compromises. They chose to move out of Manhattan and into an up-and-coming, formerly industrial part of Queens. There they could buy for less money a larger loft space than they had now. They wouldn’t be in as chic a neighborhood, and Ken could no longer walk to his office, but Mary could still work at home and be close to the kids . . . and the nanny. They were even able to take some of the money they made from the sale of their Manhattan loft and use it to pay down their credit card bills.

With those three short-term problems solved we could turn to longer-term issues: career and business plans, and savings and investment plans. Mary was quite happy being in business for herself. She knew, however, that professional photography could be a capricious business. Ken laughed when he heard that, saying advertising made photography seem secure. Ken said he’d love having the kind of control over his work that Mary had. After a few minutes of banter they’d come up with the germ of a business: they’d eventually form their own small agency, specializing at first in the computer industry. It seemed the perfect meshing of Mary’s skills and Ken’s contacts. They began putting their ideas down on paper.

Finally, Ken, Mary, and I turned toward at least contemplating a savings and investment plan. With their spending under control and their real estate costs lowered, they could see a light at the end of the financial tunnel. Once Penelope, their youngest, was in school, Ken and Mary agreed they’d be able to devote the money now spent on their nanny to their future. And now that they had the dream of starting their own business, they had yet another reason to follow through on the savings and investment plan