One day, it hits you. Hard. You realize that you wish you had done things differently. Missed opportunities … bad decisions … mixed-up priorities … mistakes that resulted in life’s biggest regrets. Some weigh heavier than others, but regret can be a tricky piece of emotional baggage to carry around.

Fact: No matter how powerful, wise or successful you are, you cannot change the past. It happened.

You can, however, change your perceptions about what you did or didn’t do, and use your experiences – even (especially!) your biggest regrets – as insightful tools to steer your future in the right direction.


Regret can be a complicated feeling to process because it is multi-pronged. It can intertwine sorrow, disappointment, anger and guilt. As if that weren’t enough, regret is a self-directed emotional reaction – and we are often our own worst critics, harshest judges and worst enemies.

Why are we so hard on ourselves? Treat a friend with the same level of disdain and it could jeopardize your relationship. While self-criticism doesn’t carry that risk (you can’t really walk away from you), it can be equally damaging, holding you back from reaching your full potential.

“The past is a great place and I don’t want to erase it or to regret it, but I don’t want to be its prisoner either.” – Mick Jagger


Recognizing what bothers you the most about your past choices is the first step in embracing them as a catalyst for change.

In my 20+ years of coaching, I’ve found that regrets seem to focus around several common themes, listed below. Do any of these have a familiar ring? If so, here are some actions you can take to overcome your biggest regrets.


Many people regret not taking the time to figure out “what they want to be when they grow up.” Sometimes it’s faster, easier and/or cheaper to jump at an opportunity that presents itself, especially when accompanied by the lure of a healthy paycheck.

“It’s never too late” is not a platitude. Many successful, well-known entrepreneurs, authors and celebrities switched career paths later in life. Andrea Bocelli was a lawyer before he quit at age 34 to follow his passion – and talent – for singing. Comedian/talk show host Joy Behar taught high school English until she was 40. Laura Ingalls Wilder, author of the Little House on the Prairie book series, worked as a seamstress and farm worker before publishing her first book at the age of 65.

Take action: If working in a mismatched career is one of your biggest regrets, do something about it – now! Never assume that a career change is impossible – at any age. Even the seemingly impossible obstacles (“I can’t afford to go back to school” or “I have a degree in biology; no one will hire me to work in marketing”) can be overcome. If you’re contemplating a career shift, do the research. Are certain credentials required? How competitive is the industry? Is this career better aligned with your talents, personal values or style? Two great ways to start your career research are by visiting O*NET OnLine and by conducting informational interviews in your desired field.

Still not sure what you want to be when you grow up? A career coach can help you explore options and identify your best career fit.


If you believed that saving was something you did with “extra money,” it probably didn’t take long to realize that those two words don’t usually belong together. People tend to adjust their lifestyles to their income levels, and spend accordingly.

Because of the invincible nature of youth, few of us think about the “what if’s” until they’re here. From unexpected medical expenses to a leaky roof, things happen. Expensive things happen – including layoffs and other situations that can lead to a disruption in your income stream. Ultimately, retirement looms at the end of the employment rainbow.

If not having enough money socked away in some form of savings is one of your biggest regrets, you are not alone. Without ample savings, many people run the risk of outliving their income, partly because, as a culture, we’re living longer than ever before. According to the Social Security Administration, one in four 65-year-olds today will live past age 90, and one in ten will live past age 95. Do you really want to have to work that long?

Take action: Create a budget, and include “savings” as a mandatory expense. In fact, pay yourself first. Whether you set up a retirement account and enjoy the tax benefits, invest in the securities markets or simply open and consistently add to a bank savings account, “better late than never” applies here.

You may want to consider some of these retirement planning tips for “late starters.” In addition, author and personal finance expert Jean Chatzky offers online calculators (savings, retirement, etc.), articles and even online courses to help you better prepare for your financial future.

Regret and worry – these are two of the biggest energy drainers and time wasters. One focuses on the past, which we can’t change. The other is focused on the future in a way that keeps us stuck.


Devoting too much time to your career is a common regret for men and women alike. Milestones (birthdays that end in “0,” friends’ weddings, kids’ graduations, etc.) often spark reflection, reminding us where we fall short of our own expectations. Many women find that, because of the amount of time and energy they spent on their career, they’re not where they had hoped to be in their personal lives (married, with children, etc.). Many men say, in hindsight, that they missed being involved in their kids’ lives, having prioritized professional results (work and paycheck) over personal relationships (family).

Take action: The beautiful thing about balance is that it’s dynamic. The scales can be tipped in either direction, often with little effort. Lost time cannot be reclaimed, but you can move forward with a commitment to prioritize your time differently. Do what it takes – pick up the phone, arrange a visit, or try to create a clearer boundary between home and work by “unplugging.”

Focus on what’s really important. Project into the future by imagining that you’re on your death bed – what do you regret? Not spending enough time traveling and seeing the world? Not making enough time to date and find a partner? Not making yourself a priority in your own life?

Regardless of the subject of your regret, one of the most powerful ways to gain a greater sense of balance is through the practice of mindfulness meditation. It can help us “show up” for our lives, instead of missing the important things while our thoughts are elsewhere. “Being mindful is not a substitute for actually participating in our lives and taking care of our own and others’ needs. In fact, the more mindful we are, the more skillful we can be in compassionate action,” according to Karen Kissel Wegela, Ph.D., author of The Courage to Be Present. Note: See Meditation, Mindfulness and Your Career for a list of the benefits of meditation, and quick tips to introduce you to the practice if it is new to you.

“Over short time periods, people are more likely to regret actions taken and mistakes made, whereas over long time periods, they are more likely to regret actions not taken, such as missed opportunities for love or working too hard and not spending enough time with family.” – Melanie Greenberg, Ph.D.


Often, life’s biggest regrets are the direct result of staying in your comfort zone. While it can seem like the logical – or in some cases, the only – choice, many people plant roots in the same place as their parents and siblings. But if your extended family lives in Minnesota, and the first snowflake of the season sends you into full-blown “I-wish-I-lived-in-Arizona” mode, it may be a signal worth noting, whether you pack your bags or not.

Perhaps you admonish yourself for not taking greater advantage of your high school or college days, when there were seemingly endless opportunities to meet people and learn about practically anything under the sun.

As life’s circumstances change, we often don’t really know how good we had it until we don’t have it anymore. That’s a sure recipe for regret.

Take action: We live in a world that presents limitless opportunities to learn, grow, get involved, meet people and develop new skills. There are two things that I recommend most often to clients to help them get outside their comfort zone: Sign up for an improv class or join your local Toastmasters club.

You can also contact local community colleges, high schools, YMCAs and park districts, which offer a plethora of adult education opportunities, from ballroom dancing to horticulture, self-defense, and learning to speak Mandarin – to name a few! Or check out online resources – here are some of the best: Khan AcademyCoursera and TED Talks.

Breaking out of your comfort zone can happen the minute you make the decision to do so. Go. Meet. Do.


Do you wish you had taken better care of yourself – physically or otherwise? Many people don’t worry about their health, putting work and other family members’ needs ahead of their own – until the waving of the first red flag. The health issues that result from neglecting your physical health are very real, taking the form of heart disease, diabetes and a host of other ailments.

You don’t have to be obese or face health issues to lament not taking better care of your body. Packing on a few extra pounds becomes a harder process to reverse with age and a slowing metabolism. This can take a toll on body image and self-esteem.

If you are a woman – particularly if you’re a mom – you may have put such emphasis on taking care of your family that you lost sight of your own sense of self. After putting your own needs on the back burner for so many years, one of your biggest regrets may present itself as panic as you approach the empty-nest stage.

Reformed addicts are quick to identify their substance abuse as one of their worst regrets in life. Perhaps you wish you could un-do damages to relationships or regain the time you lost while you struggled with addiction. Once on the other side of the addiction fence, it’s easy to say “I wish I had quit sooner,” regretting ever smoking your first cigarette, popping your first pill or having that first drink.

Take action: First, forgive yourself. While true for any of life’s regrets, this may be harder in the wellness category than in any others because the consequences have the potential to be more serious.

Next, take good care – of yourself. Today. You’ve probably heard the analogy of the oxygen mask – just as it is on an airplane, where you must first secure your own mask before securing others’, so it is in life. You need to first take care of yourself so that you have the energy to take care of those you love.

Block off “me” time, even if it feels selfish. Develop healthy eating and exercise habits that are sustainable so you’ll stick with them. It may feel like it’s too hard to eat right or incorporate activity into every day, but keep in mind that success comes from the collective impact of all of the small things you do in a day, not just one big thing. So give yourself credit for everything – big and small – that you do well. And while the rewards may not be immediate, they will be well worth it.

Not sure where to start? MyFitnessPal is just one of many websites that offer free calorie and exercise trackers, along with tips and advice to help you get started – and stay on track. If you feel you need more structure, explore the local health clubs/rec centers in your area. Many offer great incentives – especially at the beginning of the year. Weight Watchers, which promotes an overall healthy lifestyle through diet and exercise, offers meetings at centers around the nation, as well as an online-only program. Are you more of a reader? Check out Eat to Live by Joel Fuhrman, M.D.


  1. Develop conversational awareness. You can’t change what you aren’t aware of. Change happens in the moment, so it’s important that you begin to recognize when you start leading yourself down into a negative self-talk trap. Try this exercise to increase your conversational awareness exponentially: Start your day with 10 paperclips in your left pocket. Every time you have a negative thought or negative self-talk moment, move one paperclip to your right pocket. Pay attention to how long it takes to empty your left pocket. With practice, it should take longer and longer to do so – this is a great sign of progress.
  2. Accept it. Stop focusing on good, bad, smart, stupid. This kind of judgment doesn’t serve you well in building your future self. The past only serves as a lesson; it’s not necessary to ruminate.
  3. Choose differently. Make a powerful declaration that future choices will be different than your historical mistakes.
  4. Repeat this process. 


Ruminating about your past is not productive, helpful or healthy. Instead of berating yourself, try a different approach. Have some compassion for the earlier versions of you. Understanding that you are not your 17-year-old self anymore can make you feel better about the wrong turns you may have made in the past.

Reflect on your past, and use it to create your best future possible. Create a new or different path for yourself, whether that means considering a career change, planning a vacation to a place you’ve always wanted to visit or making a weekly lunch date with your grown son.

While life’s biggest regrets can be unpleasant to ponder, they can also provide valuable insight into the person you want to become, and the life you want to live – starting today.