So, how did you do with your New Year’s resolutions? Uh-huh. Me, too. This is the month of Valentine’s Day, our annual celebration of love, but many of us are in the throes of disappointment, self-recrimination, and shame from having failed to move as far toward our best selves as we intended.

It’s often a challenge to accept shortcomings in ourselves and our loved ones, and to feel compassion and acceptance toward clients and colleagues when they “fail” us or themselves in some way. In hopes of making February a true season of love, this column is dedicated to everyone who struggles with feelings of having broken their own resolutions and betrayed the trust of others.

Q: I promised my wife and twin girls that I’d get home earlier from the office to spend more time with them. I meant it sincerely, but in spite of my good intentions, something always crops up to keep me working late. My family is mad at me, and I’m angry with myself. Why can’t I find the will power to keep my promise? And how do I deal with this failure?

A: Many of us are afflicted with a form of workaholic behavior that makes it difficult to carve out “sacred space” for our loved ones. If there was more social pressure against long, grueling workdays, it might help us set better limits on our professional life.

In the meantime, I would suggest that you get clearer on what keeps seducing you away from your good intentions. For the next ten days, jot down exactly what you are working on after normal business hours. When the ten days are up, review your notes. Was the work you did really important enough to justify breaking your promise to your family? If so, could it have been squeezed in earlier in the day, or delegated ahead of time to an associate? What did you tell yourself to justify staying late to get it done?

Your takeaway from this exercise could be what you need to break out of your self-limiting pattern. As Samuel Beckett wrote in Waiting for Godot, “habit is a great deadener.”

You may find procrastination is a major contributor to your long workdays. In Predictably Irrational: The Hidden Forces That Shape Our Decisions (HarperCollins, 2008), author Dan Ariely devotes a chapter to explaining why so many people struggle with this problem. To change your behavior, Ariely, a behavioral economist at MIT, recommends increasing the cost of acting against your best interest via a fine or other sacrifice (not too severe). I’m usually a proponent of positive reinforcement–a reward if you do what’s hard and good for you–but this is interesting food for thought.

Once you know more about why you’ve been lapsing, apologize sincerely to your wife and your daughters and discuss with them how you plan to keep your promise from now on. You may find your original resolution was unrealistic and needs to be modified. For example, instead of committing to leaving the office on time every day, you might promise to depart promptly at least three nights a week, with no more than an hour extra on the other nights.

Some flexibility on all sides is crucial. After thanking his wife, Sumi, and singing her praises in Predictably Irrational, Ariely closes by vowing, “Sumi, tonight I will be home at seven-fifteen at the latest; make it eight o’clock, maybe eight-thirty; I promise.”

So you’re not alone. But don’t use that as an excuse to give up the laudable goal of spending more quality time with your family. They need it, and so do you.

Q: A colleague of mine feels he has to pick up the tab every time he goes to lunch with clients, business associates, or friends. When he asked me for advice on how to rein in this expensive habit, I advised him to let everyone take turns paying. The last time he and I lunched with another planner, I told him it was my turn to buy, but he insisted on grabbing the check anyway. I’m irritated that he asked for my advice and then turned it down. Should I say something to him, or just let it go?

A: First, simmer down and ask yourself why his behavior annoys you so. Do you feel he jerked you around? Has he inadvertently jabbed old hurts or wounds, causing you to take his act of self-sabotage personally?

Once you feel more in touch with your own triggers and less reactive toward what happened, I do think you should talk to your colleague. At a time when you’re not feeling stressed, say something like, “I’m confused about whether you really want me to help you cut back your spending. Is there something I can truly do to help, or do you want me to back off and let you tackle it on your own?” You can admit to him how you felt when he invited your assistance but ignored your attempt to help him. Is he on board with the idea of taking turns buying lunch, or would he prefer a different solution?

Some men overspend as a way to impress others with their wealth, generosity, or magnanimity. If your colleague is willing, you might help him try to determine why he insists on picking up the tab for everyone. Is he emulating some parental role model? Was he accused of stinginess in the past? Did others look down on him at a time when he was financially struggling? Once he understands and develops some compassion for the need beneath this impulse of his, he may find it easier to keep his hands in his pockets the next time a lunch bill arrives.

Q: My 83-year-old mother loves her big Buick. Recently, however, she lost track of where she was and drove up the off-ramp of the interstate. Thank heaven she didn’t cause an accident, but hearing about it scared me to death. She promised to give me her car keys on New Year’s Day, but now she says she has to keep driving in order to chauffeur her friends (who no longer drive) to appointments. It’s hard for me to press her to give up her freedom, but I’m afraid to let her keep getting behind the wheel. How can I handle this without making us both unhappy?

A: This is a very, very difficult situation. For older folks, driving is the primary activity that lets them feel truly independent, competent, and in control. Yet if physical functions fade or slow down, including eyesight and reaction time, elderly drivers can become a menace to themselves and others.

Have you tried enlisting the help of your mother’s physician? The message that it’s time to hang up her keys may be more palatable coming from an authority figure she respects.

If that’s not feasible, I’m afraid it’s up to you. Wait until you feel less agitated. Then sit down with her, take her hand in yours (or at least look her in the eye), and tell her how much her continuing to drive worries you. Assure her you’ll do anything in your power to help her stay independent and mobile.

I would do some fact-finding work beforehand so you’re armed with good solutions. Perhaps you know someone responsible who needs extra money and would be willing to chauffeur her and her friends to appointments and on errands. Some areas have organized a volunteer service of this kind. Or you might contract with a car service for a certain number of hours a month.

Remember why you love, respect, and value your mother and how much you want to keep her safe. If you also keep in mind why it’s so hard for her to make good on her earlier promise, I believe you and she will eventually reach a solution that improves your peace of mind.

Q: In preparation for retirement, a client of mine is trying to spend less and reduce his debt load. Since he’s a lavish spender, his wife made him promise to join Debtors Anonymous to help change his habits. He did attend one or two DA meetings, but fell off the wagon in a big way by buying himself a $5,000 watch in a post-Christmas sale. She wants me to talk to him, but I sense that he’s defensive about his purchase and would resent being chided. How should I handle this?

A: Before you take on this task, remember that spending can be a compulsion or addiction that’s difficult to control without outside help and support. Your client may have rationalized his big purchase (“I’ve worked hard; I deserve it”), or he may be beating himself up about this lapse. Either way, it wouldn’t be advisable to chide him.

Instead, I’d invite him to meet you in a somewhat relaxed atmosphere, maybe over coffee. Ask how he feels about purchasing the watch after having promised his wife to spend less. Would he feel comfortable returning it, and/or recommitting to Debtors Anonymous?

You may then be able to meet with your client and his wife together. If his overspending has created ongoing friction in their relationship, at the risk of blowing my own horn I’d suggest that it could benefit them to read Overcoming Overspending: A Winning Plan for Spenders and Their Partners, by Olivia Mellan and Sherry Christie (Money Harmony Books, 2009). This might also help the wife understand her husband’s addictive spending lapses and develop more compassion for him. A couples counselor dealing with money conflicts may also be invaluable to them.

Forgiveness is obviously necessary if they are to move forward as a team. People often believe change isn’t possible unless they clobber themselves or someone else, but exactly the opposite is true. When we lovingly accept the frailties and failings of ourselves and others, and communicate our emotions, needs, fears, hopes, and dreams honestly and vulnerably, the difficult process of becoming our better selves is made easier.

Remember, we are all “predictably irrational” in many ways. Nobody is perfect enough to constantly measure up to their own high standards; even those who successfully change their bad habits relapse from time to time. But by developing self-love and acceptance of your own failings, you can extend the gift of compassion to others. What a great Valentine’s Day gift that would make!

Olivia Mellan, a speaker, coach, and business consultant, is the author with Sherry Christie of The Client Connection: How Advisors Can Build Bridges That Last, available through the Investment Advisor Bookstore at She also offers money psychology teleclasses for financial advisors and for the general public. E-mail Olivia at