Should have. Could have. Would have.

No three verbs — and perhaps no words at all — better express regret. Sometimes called the “modals of lost opportunity,” they show us a hypothetical past. Often, it’s one we long to stay in. We assume that if we’d just said something else, been someone else, or tried something else, we’d be in a better position than we are now.

But positions in life cannot be lost; they can only be created. Every time we make (or don’t make) a choice, we choose one future over another. When we pick dinner out instead of eating in, we choose a life with a little more time and a little less in our bank account. We select an upside — as well as a downside.

Regret: What Burdens Build

Although we may struggle to see it in a single decision, our burdens are cumulative. If we choose to work on weekends, we tend to get ahead at work; if we get ahead at work, we tend to receive more money, as well as more responsibility. Taking on more responsibility encourages us to work even more, adding to those same burdens.

Too often, we don’t see the compounding consequences of our choices until long after we’ve made them. In “Living a Rich Life,” James Lenhoff recounts two financial planning meetings he had, one with a man in his 80s and another in his 30s.

In the first, an 83-year-old came to Lenhoff, now president of Wealthquest, to talk not about preserving his multimillion-dollar fortune, but about the regret he felt in making it. He’d trade it all, he assured Lenhoff, if he could spend the time with his family that he instead spent chasing raises and promotions. Shortly after, he met with the second man, who told Lenhoff he had to miss his daughter’s first ballet recital for a work project with a promotion attached.

“That was the day I decided it wasn’t my job just to help people big build fortunes,” Lenhoff explains in the book’s introduction. “My real job was to help people accumulate wealth without accumulating regret.”

Regret is the felt weight of those burdens. And without conscious change, they continue to accumulate. Eventually, they grow so large that they split open, spilling out as anger, sadness, and fear. “Regret is slow-building, but awareness hits hard,” Lenhoff explains. “It’s realizing someone who matters most has grown distant, or suddenly recognizing how little enjoyment you are getting from the life you are living. It’s often a very painful epiphany.”

Confronting Regret

Regret, as Lenhoff’s octogenarian client knows, cannot be assuaged by money. Especially when it comes from a lifetime of choices in a certain lineage, regret is stubborn. It cannot be bought or erased overnight; it can only be eased by an equally lengthy series of decisions in a different direction.

How can we make decisions that reduce the weight of our regrets?

1. Determine your non negotiables.

Every decision that chooses one thing sacrifices another. It’s important to identify what cannot be sacrificed, under any conditions, in order to feel fulfilled. That’s different for everyone: One person may value time for his hobbies, while another may be committed to being home in time for dinner with his family every night.

Non Negotiables, rather than serving as limiting factors, are actually helpful in making decisions — they create boundaries to eliminate some of our options, making it easier to see what’s important to us. They create a framework to make many decisions straightforward, allowing us to save our brain power for the choices that aren’t so clear-cut.

2. Make choices together.

Family life is built by one or two people, but it’s lived by three or more. The choices we make on our own have enormous consequences on our spouses, children, and friends, yet we struggle to see that when we’re asked to take on another project or fill in for a colleague. “It’s just work,” we tell ourselves.

The next time you’re faced with a choice that will affect your family or friends, try this: Gather those it will impact together around a table, and pass each person a marker of a different color. Divide a piece of paper into the number of possible choices. For each choice, create a “pro” and a “con” chart where each stakeholder can write positive and negative ways they’ll be affected by each outcome. Giving everyone impacted by a decision a voice in the process helps the whole family proceed with confidence. You will also learn more about what you as a family really want.

3. Focus on what regret can teach you — without letting it own you.
After making a choice, remember its positive consequences. A lost job is a chance to reconnect with family. Old friends who have grown distant create space to make new ones. A hurt leg is a chance to rest and catch up on reading. By seeing the growth you experienced, you can take its teeth away.

Regret can trap us into making the same decisions because we resign ourselves to it (which is why it compounds). But it can also serve as a powerful catalyst for change. Choosing to view past decisions through a positive lens can’t change the decisions themselves, but it can alleviate the associated regrets. When we dilute regret’s power, we’re better able to make choices that align with our current circumstances, which tends to produce the sort of future we want.

Regret speaks the language of could have, should have, and would have, but it doesn’t have to exert its power in the past. Regret doesn’t have control over our actions; we do. We can allow it to steer us away from what we want, or we can seize it and accept the burdens that come with it. Positions in life cannot be lost; they can only be created. 


  • Hicks Crawford

    Content marketing Expert

    Outreach Media

    Hicks Crawford is a leading Online content editor on Company. Over the past 7 years, He's worked closely with clients from all over the world to help them get more results from inbound marketing and blogging. Through experience, He has mastered some of the most powerful Tech, Content Marketing and Social Media Platforms.