The Biggest Regrets and How to Avoid Them

A few days ago, Sarah shared a wonderful article with me that I wanted to share with all of you. Entitled and appearing in The Guardian, it’s a very touching look at the genuine regrets of people who are in hospice and directly facing the end of their lives. While I encourage you to read the whole article, here are the five regrets that were mentioned:

I wish I’d had the courage to live a life true to myself, not the life others expected of me.

I wish I hadn’t worked so hard.

I wish I’d had the courage to express my feelings.

I wish I had stayed in touch with my friends.

I wish that I had let myself be happier.

These regrets make a lot of sense to me. They reflect a lot of the sentiments I have myself when I reflect on my life. When I pull back and look at the big picture of my life, these are the kinds of things I think about. I don’t think about how fat my net worth is or how much I have in my Roth IRA. I think about friendships. I think about doing the things I want to do that bring meaning to my life.

Still, even if you understand those things, there’s a big leap between knowing them and actually implementing them in your life.

Here are some thoughts on making these things move from a nice idea to a big part of your life.

First and Foremost: Four Key Principles

These five regrets do have some overlap, so it’s not surprising that resolving these regrets in your own life have some overlapping tactics. Here are four things that you can do to resolve several of these regrets at the same time.

Spend Significantly Less Than You Earn

Most of the “regrets” that people feel come from being tied strongly to their job. People often work at high-paying jobs because they “need” that income level and because they’ve made lifestyle choices that require that level of income, they “can’t” lose that job. That gives their bosses a great deal of leverage over them. If they tell you to work late, you’ll do it. If they tell you to take on hugely stressful projects, you’ll do it.

When you spend everything that you make, you cede control over your financial future to your boss, and a boss with that much power over you will exploit it, intentionally or otherwise.

The solution? Spend less than you earn – and the bigger the gap, the better. Take that difference, use it to get rid of every single debt, then start banking it. If you do that, then your job has much less control over your life. You don’t have to work insane hours. You don’t have to find yourself constantly hating and loathing your job. You have the ability to break free of expectations.

Find Pleasure and Joy in Free Things

One of the biggest reasons that people find themselves in a position where they spend everything that they make is that they derive pleasure from expensive things – their car, their clothing, their trips, their restaurant excursions, and so on.

The problem with such expensive pleasures is that they drain your finances. They slow down your ability to repay debt and keep you in lockdown in terms of your career freedoms.

Instead, devote time to finding free things that bring you pleasure. Try lots of things – if one thing doesn’t do it for you, try something else. I’ve found deep pleasure from free methods of many things I would have never believed even a few years ago – collecting rocks, geocaching, practicing meditation and yoga in my basement, writing, walking in the woods or around my neighborhood, going to community meetings, and so on.

I’ve tried many, many other free things that just didn’t trip my trigger, but I don’t regret them because without those mis-steps, I would have never discovered a large handful of free things that bring me personal joy.

Don’t Hide Your Interests or Quirks

My philosophy with personal interests and quirks is that everyone has a few unusual interests or quirks, but it’s the people who are proud of them and not ashamed of them that make them seem normal. It’s only when you feel the need to hide them that they seem weird – it’s the act of hiding it, not the interest itself.

I love playing board games. It’s one of my favorite hobbies. It’s a fairly unusual one in the big scheme of things, but I don’t hide it in any way. Instead, I love to hear about the unusual hobbies and interests of others. It’s a lot easier to feel comfortable about your own quirks and to get other people happily talking about their passions if you just don’t “hide’ what you’re interested in and instead remain proud of it.

What if you chase people away? Well, what if you do? The people that stick around are the people that are open-minded enough to appreciate your interests and quirks as well as the people that actually share an interest or quirk with you. The people that you chased away not only don’t share interests or quirks with you, they’re not open-minded enough to appreciate them. Why would you want those people around anyway?

Be yourself. Don’t hide big chunks of who you are. It might not be easy at first, but you gain far more over the long run. You’ll gain friends who are open-minded and who share interests and quirks with you – and the only people you lose are the people you don’t have anything in common with and who aren’t accepting of others. That’s not really a loss.

Find Ways to Express Yourself Without Anger or Upset

When people want to say something but can’t find a way to say it well, it bottles up inside of them, causing stress and, eventually, causing damaged relationships. It is hard to admit being wrong. It is hard to say that you’re sorry. It is hard to be respectful and polite when someone else says something you strongly disagree with.

However, all of those things are well worth doing. They preserve friendships and relationships. They give you an avenue for expressing the things you want to express.

One trick I’ve found that always works for expressing myself when it’s difficult is to realize that by not saying anything, I look worse and, eventually, feel worse than if I say something. I look worse and feel worse by not apologizing than by apologizing. I look worse and feel worse by not admitting fault than by admitting fault. I look worse and feel worse by angrily disagreeing than by finding areas of agreement.

These techniques leave me feeling better in the long run via reduced stress and better relationships and a better expression of myself.

Now, let’s look at those five big regrets that people have and see what can be done to reduce or eliminate those regrets.

I wish I’d had the courage to live a life true to myself, not the life others expected of me.

From the article:

“This was the most common regret of all. When people realise that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honoured even a half of their dreams and had to die knowing that it was due to choices they had made, or not made. Health brings a freedom very few realise, until they no longer have it.”

How can we get there?

Solution #1: Set financial independence as a life goal.

How does that connect to living a life true to yourself? It’s simple. An awful lot of the choices we make that “compromise” a life true to ourselves is because we need money. We compromise a lot of things we believe in because of our jobs and our career and our insatiable need for more cash.

If you instead set yourself on a financial path so that you can live on the returns from your own investments sooner rather than later, you quickly start to divorce yourself from those kinds of compromises. Your job doesn’t have power over you if you don’t need the money. Instead, you can choose the terms on which you work. You can still be productive, but it’s productive on your terms. Compromise walks out of the picture.

Solution #2: Devote your free time to your dreams, not time-wasters.

Instead of spending your spare time on unimportant things that don’t last and don’t add up to anything, focus as much of your spare time as possible on achieving those things that you’ve always dreamed of.

Turn off the television and work on writing that novel. Put down that magazine and start drawing. Look for situations where you’re doing things to just fill a moment and fill that moment with something that moves you towards your dreams.

What if you don’t have any free time? Often, that’s a time management issue. People often have more spare time than they think, but it’s spread out into drips and drops. If you don’t have enough free time in your life to devote anything to your dreams, spend some time looking seriously at your commitments and push back on some of them. If your life is so jammed to the brim that you can’t move anything, you’re putting your family at serious risk because of the consequences of serious injury to you.

Solution #3: Engage socially with people who embody the things you hold true.

Look for people in your life that are doing things that you value and that you view to be true in your life. Then spend time building a relationship with those people. Connect with them. Get to know them better. Spend time with them. We are constantly influenced by the core people in our life, so you want to do what you can to ensure that the core people in your life exhibit values that are important to you.

If you’re struggling for a way to do this, look for community groups and meetings where you can find people who are interested in the things you care about. Use sites like and your city and public library websites to find these groups, then make an effort to join in.

I wish I hadn’t worked so hard.

From the article:

“This came from every male patient that I nursed. They missed their children’s youth and their partner’s companionship. Women also spoke of this regret, but as most were from an older generation, many of the female patients had not been breadwinners. All of the men I nursed deeply regretted spending so much of their lives on the treadmill of a work existence.”

How can we get there?

Solution #1: Make pay a lower priority in terms of your work.

Rather than focusing on squeezing every dollar out of your job, focus on other benefits. Favor the job that gives you more flexible hours over the one that pays a little more. Ask for “raises” in the form of increased vacation time or a more flexible arrangement.

What about the money you’re leaving on the table? If you’re committed to building a financially independent lifestyle, you’ll already be spending less than you earn, so making a choice like this isn’t nearly as hard as it sounds.

Solution #2: When you’re forced to choose between work and loved ones, choose loved ones.

Many people feel as though they must choose their careers, so they do things like skipping their child’s recitals or missing family dinners or never finding time for a conversation or a board game. Don’t. You’ll regret it.

When your loved ones need you, work can always wait. Your work project might seem more urgent, but ignore the urgency. Turn off your cell phone and go to that recital. Turn things back on when you get home and get caught up.

I will flat-out admit that this was one of the big reasons that I made a career shift. I was finding myself choosing work over family far more than I liked and I was regretting it on a daily basis. I didn’t want that to continue, so I took the leap. I don’t earn as much now, but I don’t regret the choice for a second.

You will never regret being there when your family needs you. You’ll probably regret choosing yet another work task over that family need.

Solution #3: Maintain a healthy emergency fund.

When you’re pressed against the financial wall and have no breathing room, every choice is scary. If a mis-step can cause your house of cards to completely fall apart, you become paranoid about each decision.

The most powerful single solution here is to simply build a strong emergency fund. If you don’t have at least $1,000 sitting in your savings account somewhere, you’re simply waiting for the other shoe to drop in your life. You’re in a difficult position professionally, you’re probably facing serious stress, and you’re at risk of a disaster in your life.

Build an emergency fund. Make room for it. Don’t ever find yourself in a situation where big chunks of your life fall apart in a week or two after a job loss or you’re in total panic mode if a car failure happens. It’s not good for you or the people around you.

I wish I’d had the courage to express my feelings.

From the article:

“Many people suppressed their feelings in order to keep peace with others. As a result, they settled for a mediocre existence and never became who they were truly capable of becoming. Many developed illnesses relating to the bitterness and resentment they carried as a result.”

How can we get there?

Solution #1: Write it down.

If you’re not comfortable saying those things, write them down. Start a personal journal just for yourself and write down the things you’re feeling.

I strongly encourage you to focus on the positive feelings. Write about the people you really care about and why you care about them. Even if you find it difficult to say such things to those people, you can still manage to write about them in your journal.

Sometimes, you may need to let some negative feelings out, and that’s a good thing. You should still find ways to look for the positive people in your life and write about them.

Solution #2: Reflect on how you would feel if people said those things to you.

When you’ve thought about what you would like to say to others and written those things down, consider how you would feel if those things were said about you. Would they hurt? Could you find a way to convey those thoughts without bringing the pain?

Even in the most negative writings about others, there are still seeds of things that can be useful to say. After all, it’s pretty hard to be angry with someone if you don’t care about that person on some level. If you didn’t care, you wouldn’t be angry.

Solution #3: Start slowly.

You don’t need to spill every inner thought at once. It’s not easy for most people. Instead, look for simpler things to say.

Call up your grandparents and tell them that you love them and that you remember some of the good things they have done for you over the years and how much of a difference those things made. Call up your best friend and just tell that person thanks for being there so often in your life. Tell that person that’s always nice to you that they’re awesome and that you appreciate their kindness.

Those words of kindness ripple outwards. Sometimes you’ll see the effects and sometimes you won’t, but the effects are always there and they often bounce back to you in ways that you don’t see.

Over time, doing this will help you to build the courage to say harder things and also to find the words to express those things, but in the interim, sharing positive thoughts that you previously held inside will make a tremendous difference.

I wish I had stayed in touch with my friends.

From the article:

“Often they would not truly realise the full benefits of old friends until their dying weeks and it was not always possible to track them down. Many had become so caught up in their own lives that they had let golden friendships slip by over the years. There were many deep regrets about not giving friendships the time and effort that they deserved. Everyone misses their friends when they are dying.”

How can we get there?

Solution #1: Go beyond the “like” button.

Many people “maintain” friendships by just clicking on the “Like” button on Facebook. That’s not maintaining a friendship.

If you want to maintain a friendship, take a few moments once a month – or preferably more often – and write that person a message. Ask how that person is doing and what they’ve been up to. Don’t fill it with blather about yourself – if the other person asks, fill in the blanks, but lead with interest in the other person.

Isn’t an old friend worth more than clicking a “Like” button?

Solution #2: Host dinner parties. Lots of them.

If you want to build a connection with people or maintain an existing one, there are few ways that are more effective at doing that than inviting them over for dinner. People open up when they’re invited into your home and they share a meal with you.

Not only are dinner parties a powerful way to maintain friendships (and build new ones), it can open the door to invitations to other dinner parties and other opportunities to build new relationships and maintain old ones.

Your dinner party list should regularly include all of your friends in the area that you wish to maintain friendships with (not all at once, but on a regular basis). Don’t be afraid to mix them up, either, and don’t be afraid to invite friends who may not know each other but may enjoy being introduced.

Solution #3: Incorporate visiting old friends into your travels.

Rather than focusing your travels solely on visiting new places, use some of that focus on visiting old friends as well. Use your travels as an excuse to meet up with friends that are spread around the country (or around the world).

Not only can this reduce the cost of your travels, it can provide a great way to maintain an old friendship. When you’re on a trip and you want to make time to see someone, it means something to them. It’s a powerful way to maintain that friendship, something that you’ll always be glad you did.

I wish that I had let myself be happier.

From the article:

“This is a surprisingly common one. Many did not realise until the end that happiness is a choice. They had stayed stuck in old patterns and habits. The so-called ‘comfort’ of familiarity overflowed into their emotions, as well as their physical lives. Fear of change had them pretending to others, and to their selves, that they were content, when deep within, they longed to laugh properly and have silliness in their life again.”

How can we get there?

Solution #1: Make every day a Valvano day.

I’m a huge believer in Jim Valvano’s plea to include three things in every day of your life: to laugh, to cry, and to learn something. If you do those three things, you’ll have a great day.

Make that a daily goal. Find something that makes you genuinely laugh. Find something that makes you genuinely cry. Learn something new. If you do those things over and over and over again, the emotions that bottle up inside of you drain away and you’ll find a much greater inner peace.

Solution #2: Try new things – and don’t be afraid to mess them up.

Trying new things constantly opens the door to new avenues of happiness in your life. It might show you something new that you love. It might provide you with a great story. It adds a new experience to your collection of life experiences.

So, what holds people back from doing this? People are often afraid to mess things up. Don’t. Don’t let that fear of failure worry you in the least. For starters, failing is a key part of learning – it’s pretty hard to learn how to do something without messing up along the way. For another, knowing how to fail makes it easier to handle other failures in life – and, as humans, we all fail. Finally, failing in a simple way in front of others is incredibly humanizing. I can’t recall ever not becoming closer to someone because we both bungled in the process of learning something new. That failure, when it’s enjoyed and laughed at and then overcome, is incredibly life-affirming.

Try something new. Sure, you’ll probably fail. Relish the failure and the new experience.

Solution #3: Play with a young child without distraction.

Few things feel better than simply turning off all of your distractions and just playing with a young child for a while. Don’t think about anything else. Don’t worry about life’s issues. Just let it go and play.

Roll down a hill. Build a sand castle. Play soccer in the grass. Dance like crazy. Make a pitcher of lemonade and drink it together. Have a tea party. Design a LEGO mansion. Let go and just get lost in the imaginative and joyful world of a child for a while.

Not only will that child absolutely adore you for this, many layers of your stress will fall away. It has been a restorative thing for me all throughout my life, even during the times when I couldn’t imagine being a parent.

Final Thoughts

You have the power to build a life that isn’t filled with the typical regrets. It just requires that you make some changes to your life, starting with getting a good grip on your finances and making better use of your free time.

A good financial foundation runs like a thread through all of these ideas. The solutions presented here either rely on good financial choices directly, are made much easier by having a financial buffer, or directly contribute to an improved financial state. Good finances help you step away from the challenges that hold you back.

Combining smart financial choices with the other solutions in this article can go a long way toward melting away those regrets, leaving you with a more complete life. In the end, it’s that complete life that we all strive for.

Good luck.

Loading Disqus Comments ...