How to Make Life’s Biggest Decisions

Should I change careers? Should I relocate? Should I divorce…or marry? These and other big decisions are difficult for almost everyone. They demand that we step into the unknown, which can be disorienting, unsettling…even ­terrifying.

Here are four ways to improve your odds of making smart decisions…

Strive for a B+ result when making big decisions. It’s natural to search for perfect A+ options. Of course, you want an A+ job where you are fulfilled and well-compensated…an A+ relationship where everything goes smoothly with your partner…and an A+ retirement where you stroll along the beach looking as happy as those TV-commercial retirees. The trouble is, A+ options don’t always exist, and if you target these, you might end up missing out on perfectly good B+ options. Or you might continue pushing yourself to build that A+ retirement nest egg or afford that A+ house when you would be much happier if you decided the B+ nest egg or house was good enough and gave yourself permission to relax.

What to do: When you struggle to find an option that seems perfect, remind yourself that a B+ is really good. A B+ (or an A–) is a whole lot better than average…and it’s a whole lot better than never choosing an option and wasting months or years searching for an A+ that doesn’t exist. And if you are a person who tends to judge your life largely by others’ lives, keep in mind that most people who seem to be in A+ situations actually aren’t—it’s just that you don’t know the troubles they have!

Don’t turn down an option because you’re not certain it’s a step forward. When people consider the opportunities and options that come their way, they often think in terms of forward progress and upward mobility. Would accepting this job be a rung up or a rung down for my career? Would going back to school or relocating be a step forward or a step back? Often the answer isn’t clear, and that lack of clarity can lead to inaction and missed chances…or to regret when an option we select turns out to be the wrong one.

What to do: Visualize your options as openings in a maze, not rungs on a ladder. If you reach an opening as you walk through a hedge maze, you wouldn’t ­expect to be able to see far ahead or know for sure which path was correct—you would just decide based on the knowledge that you have and move forward. That’s all anyone can really hope to do with many life decisions. When you look back years later, it might seem obvious which choices you should have made, but there’s a good chance that this was unknowable at the time.

Helpful: When you need a reminder that you can never make decisions with perfect foreknowledge, ­reread Robert Frost’s poem “The Road Not Taken.” Its concluding lines are among the best known in American poetry and among the most ­misunderstood…

Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.

Read the poem, and you’ll see that its protagonist is not extolling his wise decision or advising us to choose an unconventional life—he is admitting that at the time he made his biggest decision, he really didn’t know how to choose between his options and eventually did so essentially by chance.

Live in your decision for a day. Most people have had the experience of making a decision and then waking in the middle of the night convinced that they made the wrong decision. Sometimes there’s no turning back once you’ve committed.

What to do: Before you finalize a major decision, tell yourself you’ve already done so and then live with this for 24 hours, time permitting. If you’ve made a good choice based on what you know and can reasonably expect, it probably still will feel good throughout this day.

If your decision nags at you during this day, dig into the nagging feelings. If they are feelings of discomfort or fear, that does not mean your decision is incorrect—it’s perfectly normal to experience discomfort and fear when making major choices. But if what you feel is something more akin to regret or dismay, it’s worth reevaluating your decision. To do this, tell yourself you have made a different choice—whichever option was in second place—and live with that decision for a day. If you get through this day without feeling regret or dismay, this might be the better choice for you. Example: A writer was offered a prestigious position. But after living for a day with the decision to a­ccept it, he realized it wasn’t something he wanted to do but rather something he felt he was expected to do. Turning down the position felt right.

If every option you consider triggers feelings of regret or dismay, stop searching for the option that feels right and instead consider which feels least wrong. Sometimes in life we must settle for our least-bad option for the time being. And you never know—you may find out that it was a great decision all along and you were making yourself suffer unnecessarily.

Ask yourself if there is a “normal” to go back to. When people are faced with a potentially life-altering choice, most lean toward one option above all others—the option to “get back to normal.” They favor this not because it’s their best choice but because it feels safe. But there’s usually a problem with the “back to normal” option that they have failed to consider—the “normal” they are trying to return to may no longer exist. Examples: Moving back to your former hometown is an option when you are deciding where to relocate or retire—but that town may no longer be the place you remember, and you are no longer the same. You still may love the town, but consider how much has changed since you lived there. Taking back your spouse might be an option after a separation—but the relationship may be different after the split and reunion.

Even when there is an option that does get life somewhat back to normal, this feeling will not last forever. Staying put in your current job rather than taking a new one is fine, but as time passes, your colleagues will change, your responsibilities will change and/or you may no longer find the job fulfilling.

What to do: It’s fine to include a familiar place, person or position among your options—returning to something can be a reasonable choice—but evaluate this option just as you would a brand-new opportunity. Ask the same probing questions about it…and employ the same vetting process with it. Example: If you rent a home for a month in each of the towns where you are thinking of retiring, do so in your former hometown if you are considering it as well—don’t assume that you already know this place.

Whenever you experience warm, comfortable thoughts about any kind of “back to normal” option, ask yourself, In what ways might this option be different and less comfortable than it used to be? You then might comfortably choose a new path in the maze!