14 Choices You’ll Regret In 20 Years

1. Stressing out

When we fail to see the big picture of the miracle of life itself, we get caught up in the intricacies that simply don’t matter much – if at all – in the long run. The first book I wrote was about how to defeat stress, because it is one of the greatest enemies of the human race. Focus on the good things, not the setbacks, and you certainly won’t regret it. Listen to Bob Marley, mon’.

2. Working too much

Perhaps the most common regret people have in later years is working too much – the rest of us should take note. So much of life seems to revolve around making money and getting ahead, but lifestyle is a choice. There are “poor” people living much better lives than wealthy workaholics. People work hard to be able to buy more stuff, but we’re better off with fewer things. Possessions are not the key to a fulfilling life!

3. Not investing (enough)

One surefire way to be stressed out of your mind is to manage your finances poorly. You should be budgeting. Invest 10-15% of your income in whatever you feel comfortable investing in. Take on more investment risk while younger and gradually decrease your portfolio risk as you near retirement.

4. Living a lie

Countless people are not living the lives they truly want. We are easily influenced by the world – sometimes to our own demise. Not living true to yourself was the number one regret of people on their deathbed in Bronnie Ware’s famous blog post – Regrets of the Dying.

5. Not taking that risk

The “what ifs” are agonizing and the worst kind of failure. Truly, it’s worth failing just to see what happens (and hey, maybe you’ll succeed!). You live and you learn. But if you don’t really “live,” you won’t learn.

6. College or not?

Some people regret going to college. Others regret not going to college. I think the easiest way to determine which one you’d be is to (1) examine how important learning is to you, and (2) see how you feel about the school’s system of learning vs other forms of learning. For some, reading books is all the “school” they need. For others, being taught by another person is their favorite method of learning – or perhaps they want a degree for better job prospects. Whatever your preference, don’t underthink the critical life decision of how much formal education to pursue.

7. Buying too much stuff

Everyone can accumulate things, but not everyone can get rid of things. Excess possessions are a mental anvil and a physical impediment. I’m happy to know I can move anywhere in the world in 30 minutes.

8. Waiting

Are you waiting for the right moment? That could be a huge mistake. Seize the day, my friend. Do what matters right now, or you may not ever do it. The timing is never going to be perfect.

9. Wingin’ it.

The opposite of this blog’s namesake – wingin’ it sounds sorta neat-o, but it is the worst way to live. Those who wing it see life as an on-rails type of experience and they go with the flow. The truth is, the rails are only 2 feet tall. Sometimes, wingin’ it is erroneously seen as “living in the moment.” Let me just say that the moments we create matter most. Step over the railing and decide what moments YOU want to live in.

10. Staying in your horrible job

How many people do you know who love their job? About seven, right? And most don’t do anything about it. Constantly apply for better-suited jobs. Start a business. Use your problem-solving skills! If you love your job, you’ll probably love your life.

11. Not spending enough time with important people

Friends, family, children, spouse, etc. You know something that humans never regret? Spending “too much” time with people they love. Make this a priority and enjoy the richness of genuine, close relationships.

12. Trying to be normal

Nobody is normal. We just feel pressure to act like it – to revert to the mean. It’s why we start out as fun children and grow up to become boring adults. Aside from natural maturation, societal conditioning is heavily involved. The people labeled “crazy” or “weird” are having the most fun. Don’t you want to have more fun? I do… and I’m weird.

13. Eating food crap

If all of us intimately understood everything about the food we eat and how it affects us, quality food would see a massive increase in demand. And it is. As understanding grows and America’s health deteriorates, so grows the demand for organic food. Look at the emergence of Whole Foods as an example of people beginning to wake up!

14. Living With Regret

Maybe you’ve made most or all of these mistakes already. Even so, let them become lessons for future consideration, not life anchors. Living with regret is the worst of all, something you’d regret later in life.

Let your current regrets fade into weightless life lessons, and pursue the present moment with vigor. You won’t regret it.

About the Author

I'm lazy, but you can call me Stephen. When you're as lazy as I am, you need superior strategies to live well. My strategies are so effective that I'm productive every single day. As the world tries to figure out how to always stay motivated, I create strategies that don't require it.

Curtis Marshall

Solid post Stephen! As someone who is trying to live a better story, I agree with every single one of these.. and I would have to add Watching Television and Avoiding Failure. One fries your brain and is an epic waste of time. The other will leave you paralyzed with inaction

On a side note, I just read your guest post on ProBlogger and I’m guessing you’ll be seeing your traffic escalate again in the very near future. The content from that post resonated with me because I was thinking the same thing this morning… Content is NOT actually king! Influence is king, and content only helps increase your influence.

Ben Norman

A good post Stephen,

#5 rings most true with me. Although it’s all about taking that calculated risk I find it far too easy to talk myself out of something. Saying that I’ve not (yet!) had any spectacular failures either so I’m not sure how I’d handle them!

Stephen Guise

Hi Curtis. Watching television would have been a great addition to this list. Last I heard, the average time spent watching TV for an American is 6 hours a day! Avoiding failure is also a huge error to make – I’ve written about that topic several times.

I was surprised to discover that good content even with traffic isn’t enough. I guess people could still be reading it, but I only consider it effective if people are compelled to share/comment. Awareness and influence dictate so much about how content is received. They are the lens through which your content is seen.

Anyways, thanks for dropping by and adding in those great suggestions for 15 and 16!

Stephen Guise

Hey Ben,

Yes, I can imagine not taking risks has held most of us back in some way or another. As I’ve built up confidence in certain areas with that, I’ve (thankfully) found that it only gets easier once you start taking risks and failing some. It’s the realization that life is more exciting and rewarding when you take risks and that failure is not a big deal at all. I’d say it’s worth it just to avoid a boring life, ya know? 🙂

Amrit Hallan

Hello Stephen.

It’s strange that today I was discussing the same thing with my wife when we were having dinner. There have been some business problems and they manifested just when I had begun to feel I have figured out everything. I was explaining to her that whatever is happening today is nothing but the effect of what I have been doing and not been doing for the past 4-5 years therefore I can’t blame someone or something. All I have to make sure is I don’t repeat the same pattern and learn from my mistakes. So whatever I’m doing today, I must remember what impact it is going to have on me and my family 5-10 years down the line.


Hi Stephen,

I’m living out the ‘working too much’ scenario right now. However, I hope that it makes for a better life in the future.

I imagine that the ‘living a lie’ scenario would be very hard and would take a serious toll after 20 years. I definitely would not want the feeling that goes along with that.


I’m glad to be reading this at 22 and to be able to say I’m “only” 7/14 🙂

Stephen Guise

Amrit, that’s a bittersweet realization, isn’t it? I had the same one recently when I realized that I’m not where I thought I’d be at this point in life. I do find it important to give myself credit for the good things I have done, as I’m a firm believer in positivity, but I’ve missed out on so many opportunities by being conservative and passive.

You’re right. Don’t repeat your mistakes. Make new ones! As long as you’re making new mistakes, you’re moving forward. 🙂

Stephen Guise

David, I admit I’m doing a little bit of the work too much scenario myself. In the past I’ve been on the other end of the spectrum. It’d be nice to strike a balance here. The main thing to avoid is creating a lifestyle that encourages you to overwork because your cost of living keeps rising. That’s dangerous and a recipe for burnout!

I bet we’ve all lived a lie in some way on some level. Something as subtle as neglecting your true career interest is living a lie, and I’ve done that. It’s easy to live a lie and not know it by being influenced by your peers to the point where you lose your identify.

Stephen Guise

Hey, that’s not too bad! Which 7 though? Some are more important that others. Like, if you’re always stressed out, that would result in general misery.

Michael Underhill


Is indeed an excellent list. One thing that I would have to add to it, as it has impacted me and my life in countless and unimagined ways. I refer to the mistake of holding on to blame, and it’s correlate refusing to forgive. It is painfully astonishing the damage I have seen done by my own hand to my own life, by not moving beyond wrongs (perceived and actual) and those whom I believe to be responsible for imposing them upon me. I still have trouble not looking around to place the responsibility for this very mindset and its presence in my life somewhere or upon someone other than myself. At the end of the day (or my time here) it’s not so important the origin of the injustices and setbacks I have endured, it is what I have chosen to do to counter and overcome them and to consume and actualize what is there to be learned.

Stephen Guise

Important stuff Michael. I know that I have the best results in life when I take full responsibility for my situation. And when you’re thinking about the wrongs that have been done, you could be looking forward instead. This would make for a fine #15 to the list. Thanks Michael.

You identified your situation masterfully, by the way… very perceptive.

Vishaun Kistan

Another great article, Stephen. I totally agree with you at the latter part of the blog. ‘Living with Regrets’.

Stephen Guise

Yeah, that’s the big one…you’ve got to let the past go.

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