“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

One day, it hits you. You wish you had done things differently in life. You think about all of the missed opportunities, bad decisions, mixed-up priorities, and the mistakes that resulted in your biggest regrets. Some weigh heavier than others, but regret can be a tricky piece of emotional baggage to carry around.

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 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.

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 had the privilege of coaching two clients as they neared the end of their lives. I had powerful, deep, trusting relationships with these two executives that transitioned from working on how to be a better leader to how to live out the rest of their lives in the best way possible.

Scott (not his real name) was a successful CEO of a large corporation who admitted in his final days that he had lost sight of what was really important during his life. He contemplated why he spent so much time in business meetings, when he could have had lunches with his wife that would have been much more meaningful. After a diagnosis that gave him only a few months to live, he began to process his life’s decisions differently. He transitioned from being completely focused on building his business to embracing the fragile moments of life – the time he had together with his family and friends. He regretted that he didn’t live his life with reflection on what was really important so he spent his final months putting all of his time and energy there.

My other client Karen (not her real name) appeared to be the sweetest woman on the outside but had been hiding anger, frustration and disappointment on the inside for years. She was successful enough to be able to throw money at and solve most problems in her life, until she was diagnosed with a terminal illness that no amount of money could cure.

In the last few months of her life, she was finally able to express all of her anger and frustration at the things she didn’t like about her life, including a bitter divorce that made her distrust relationships. Once she was finally able to let that go, she told me she felt lighter and free and that she wished she would have done this much earlier in her life. She finally felt complete.

Like Scott, Karen wished she would have played more during life rather than focusing on business as much, and I’ve found that this regret is a common theme among other clients as well. If any of the following disappointments ring true to you, here are some actions you can take to overcome your biggest regrets.

Career Choice

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 often 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?

Building a Secure Financial Future

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 like the current pandemic that can lead to a disruption in your income stream. Ultimately, retirement looms at the end of the employment rainbow.

financial regrets

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.

Related: A Pandemic of Financial Anxiety

Work-Life Balance

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.”

Related: Master Work-Life Balance

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?

wellness mindfulness meditation

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 mediation. It can help us “show up” for our lives, instead of missing the important things while our thoughts are elsewhere.

Stepping Out of Your Comfort Zone

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-Florida” mode, it may be a signal worth noting, whether you pack your bags or not. In today’s COVID climate, many of us – including yours truly – now realize that we can do our jobs from anywhere and therefore, live where ever we like.

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.

step out of your comfort zone

Take action: We live in a world that presents limitless opportunities to learn, grow, get involved, meet people and develop new skills. Taking an improv class or starting to learn another language are two great ways to step outside of your comfort zone. Others include taking advantage of the many adult education opportunities offered at local community colleges, high schools, YMCAs and park districts. From ballroom dancing to horticulture, self-defense, or learning to speak Spanish, the possibilities to learn something new are endless. Breaking out of your comfort zone happens the minute you make the decision to go and 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. Neglecting your physical health and failing to manage your stress can result in myriad ailments, from insomnia to chronic pain, heart disease, diabetes and a host of other serious problems.

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, start taking care of yourself. Today. Secure your own “oxygen mask” so that you have the right energy to take care of others.

reflect path to your future

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 over time. So, give yourself credit for putting forth the effort – and for incremental progress.

Pursuing Hobbies

Think about all of the hobbies you would like to pursue if you had the time. Now think about how you end your days when you are exhausted. Most of us want to do something mindless that doesn’t require a lot of energy, so it’s little surprise that watching TV is by far the most popular use of leisure time in the U.S.

However, when you spend time on a creative hobby such as music, writing or art, you’re actually boosting skills that help you in the workplace. When you give yourself some mental space, you open up room for creativity. Neuroscientists have found different parts of the brain are involved with rational thought and emotions. You must engage both in order to be creative.

Take action: Although you may think you don’t have time for creative hobbies, it doesn’t take long to see the benefits. A study found that spending 45 minutes making art helps boost confidence and ability to complete tasks. Take time out of your busy day or week to do something that feels creative and fun, without any guilt.

Letting the Good Ones Go

Often our regrets focus on past relationships in our lives, whether romantic or friendship. We may have failed to stay in touch with good friends from our youth and regret not putting forward the effort. We may regret leaving a relationship, wondering if we had endeavored to make things work with a partner if it would have resulted in staying together.

Take action: Whether you want to reconnect to an old love or you just want to be ready for someone new, it’s important to understand what went wrong in your previous relationships. Was there fear of commitment? Did you lack the skills to transform romantic feelings to deeper love? Understanding whether your behaviors contributed to the problem can make a big difference between another relationship succeeding or failing in the future.


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.

The path to self-forgiveness involves acceptance. Stop using labels like good, bad, smart or stupid. That kind of judgment doesn’t serve you well in building your future self. The past only serves as a lesson; ruminating won’t help you grasp that lesson and, in fact, can get in the way of making better choices for your future.

Reflect on your past, and use it to create your best future possible. Make a powerful declaration that your future — effective now — will be different. 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.

Learn more about career coaching