How To Live With No Regrets

September 10, 2014

Live With No RegretsIf you had to summarize everything you know about money into one sentence, could you do it? Just a few months ago I wouldn’t have been able to but now I can. In fact I can boil it down into just two words – No Regrets

If you’re a stickler for finance I know you may not agree with this tip. I can understand why you might read it with some skepticism. Until this last May I would have felt the same way about what I am going to say.

In fact, part of me thinks I shouldn’t even waste your time trying to convince you of its importance. As a parent, I’ve seen how people don’t really believe the advice you’ve given until they do the opposite and suffer the consequences.

It doesn’t matter if you’re 8 or 48, the only way you really learn is through experience. So I know that you’ll probably read what I’m about to share, maybe file it away or just blow it off, and go on with your day.

This Changed My Life

Whether it helps you or not I feel obligated and compelled to share this with you because it’s changed my life. If a red flag just went up in your mind because you’ve heard about so many “life changing” experiences, I understand. I really shouldn’t even use that term because of the skepticism it can trigger but I’m sticking with it because it’s accurate.

Not only has it changed what I do in my day to day life but also how I think about life and how I experience it. I won’t go into detail about what happened to me and why I feel so strongly about this tip because it doesn’t really matter. It’s not about what happened; it’s about what I learned.

Sharing What I Learned

This is really about you, not about me. I had a nightmarish time in my life last May but in hindsight it taught me a lesson I probably wouldn’t have learned otherwise. I’ve had the benefit of an Ebenezer Scrooge type experience, now I want to pass the insight I gained onto you.

So I’ll just say that I didn’t think I’d be around to see my kid’s next birthday and leave it at that. Experiences like those send your mind into places you’ve probably never explored before. As I lay there wrestling with these fears night after night my brain always ended up sliding back into the same heart breaking place. A giant cauldron of regret. My every waking action simmered in an ever-present, ever-growing feeling of regret and remorse.

That is why my tip to you is simple but vitally important – Live With No Regrets

I know it’s not an actionable tip, you can’t take it to the bank. It’s not going to help you save $500 in 20 minutes. It’s really more of a mantra or a philosophy than a tip.

No Second Chances

Years from now when you look back on your decisions and choices, you won’t be able to turn back time and get a second chance. If you’re able to think back on your life with a sense of peace and gratitude that will be amazing. If not, you’d give any amount of money to be able to go back and try again.

But of course you can’t, life doesn’t work that way. That’s why trying to live with no regrets is so important. So what are you supposed to take away from “No Regrets”? It’s a pretty vague philosophy, how can you apply it to your situation? Here are 5 ways to adjust your life so you’re more likely to look back with fewer regrets:

1) Quantify What’s Important

Most of us don’t have a bottomless bank account or endless days of leisure. Since we’re constrained by time and money we have to make decisions about how to use those limited resources based on what’s important to us.

It’s difficult to put a monetary value on lots of things in life but you can measure them against other things in your life. An example of this that you’ve likely faced before is choosing which job to pursue or accept.

You’ve probably wrestled with how important job flexibility was – whether you wanted to schedule your job around your life vs scheduling your life around your job.
Weigh Your Options
Things like the importance of flexibility compared to salary, your interest in the job vs benefits, opportunity for advancement vs required travel.

These are all aspects of a job that you have to weigh against one another. It’s really tough to put a financial value on flexibility, job interest, and time away from home but you still have to consider them when choosing the right job for you.

You don’t have analyze every decision but it really helps to take the time to measure and weigh the important factors when making big life decisions.

Weighted Criteria Matrix
This is one tool you can use to measure and rank life decisions and the factors that go into them. I talk about it in the context of a job search, here’s how you can apply it to help choose the right job.

Simple Head to Head
You can use the same approach for any big life decision but you don’t have to be that thorough. There’s a simple trick I taught my son for making decisions when he got hung up choosing between different options – the head to head method.

You take your top 6 options and compare them with each other one pair at a time.

  • Option #1 vs #2 – Pair A
  • Option #3 vs #4 – Pair B
  • Option #5 vs #6 – Pair C

Then you compare the best option from Pair A against the best option from Pair B. Whichever one comes out on top, you compare against the best option from Pair C. The winner of that “head to head” is your top option.

Not very sophisticated but if you make a note about each pair and your reasons for choosing then you come out with a winner and you know why you took that path.

Whatever your method, however simple or complex, it’s vital to learn how to quantify what’s important in life and make your decisions based on that.

You won’t always (ever) have perfect decisions as a result but following a system can help you avoid making a string of life decisions that you end up regretting in the short and long term.

2) Get Better at Saying No

Learn to say no
What are the most important things in your life? What do you want to accomplish, to leave as a legacy? Since you have a limited amount of time and money you want to focus on investing them towards achieving those goals.

Every time you say yes to spending time or money on something that doesn’t match up with your life goals you’re chipping away at part of what’s important to you.

I’m sure some of these “asks” might sound familiar to you:

  • Can you take on this project?
  • Will you volunteer for this position?
  • Can we tackle this house project?
  • Will you work this weekend?

Whether it’s your boss, friends, spouse, co-workers, church, club, parents, neighbor, or kids there will be people asking for your time.

Getting better at deciding who to say no to and how to say it will free up some of your time to focus on meaningful parts of your life.

If you’ve ever seen the movie Office Space you’ll remember the banner the boss (Bill Lumbergh) hung up that asked “Is This Good for the Company”. Lumbergh instructed every employee to ask that question before every decision they made at work. You can tweak Lumbergh’s suggestion and ask yourself “Is This Good for My Life” every time you’re asked to give time and money.

Unfortunately saying no is something that I’ve never been very good at. I would love to hear in the comments what approach works for you. Here are some tips from LifeHacker and Zen Habits on how you can learn to say no.

3) Be Present

Offering this type of generic advice runs counter to my personality. I prefer specific and actionable tips and I’ll admit that suggesting you “be present” is vague and not action oriented.

I found some decent tips for “living in the moment” that I’ll share in a minute. The main take away I’d like you to remember is not to spend so much time thinking about the future that you ignore the present.

Soak it in.

This catchy quote from Alice Morse Earle sticks in my head:

“Yesterday is history. Tomorrow is a mystery. Today is a gift. That’s why it is called the present.”

Unfortunately I haven’t always heeded this advice. As you know from reading this site, I’ve been working hard to accumulate and preserve money since I’ve been a kid.

I’ve always been thinking about the future, about what was next. However, one of the lessons I learned from my health scare was that I wasn’t making enough space in my brain for the present.

It can be tough to do with competing demands from work and family and today’s attention greedy society. Here are some actionable tips to help you along:

4) Allow Yourself to Celebrate

Celebrate Success
If you’re an overachiever you’ll have days where you feel defeated. Nothing went right, you made little/no progress, or things even went really wrong. It’s easy to get down in the dumps on those days but don’t let it hold you down.

If you’re reading this then chances are you’re better off than most of the people in the world. Even when you have a terrible day your life is overall still pretty good.

Why is it important to pep yourself up?

If you get hung up on the down dips you can waste days and weeks fretting over them and missing out on other things going on in your life. If you’re healthy and keep a positive attitude then you can overcome those challenges tomorrow.

The reason there are so many famous quotes about how successful people are good at dealing with failure and moving on is because it’s true.

Revel in the Small Wins
As achievers we tend to set our goals high and get frustrated when we don’t achieve them. One aspect of living with no regrets is allowing yourself to celebrate the gains that you do make even if you are not fully achieving your goals.

I’m not saying you shouldn’t push yourself because ambitious people help make the world go around – just give yourself permission to celebrate a little.

I’ll admit I’m not good at this; in fact I’m pretty terrible at it. I’ve been getting better lately but it’s still tough for me to find a balance between achievement and celebration.

Let me ask you this. If your life is only about achievement and you die next month do you think you’ll regret the celebrations you missed out on?

5) Be Lean

[Photo Eric RiesMr. Lean (Eric Ries)]

Being lean has a double meaning in this case. The first and most obvious is to stay healthy. Regular exercise can not only help you live longer – it also gives you time to yourself to reflect on, plan for, and appreciate life.

The second meaning has its roots in lean manufacturing. I was exposed to it via Eric Ries and his concept of a Lean Startup in business but it can also apply to your life.

In a nutshell, the approach is about quickly discovering the right thing to create. The goal is to avoid wasting time and money on something your customers don’t want. A great way to achieve this is by running lots of little tests to quickly learn whether you’re on the right track or going off in the weeds.

Lean in Your Life
You can apply this same approach to big decisions in your life. Rather than making assumptions and spending big chunks of your life trying to achieve something based on those assumptions you can setup small tests and spend some time trying to prove/invalidate them.  For example, if you’re thinking about changing careers you can look for an internship, temp job, or volunteer role in the industry/career you’re considering to see if it’s worth investing further time and money into.

Testing Assumptions
Maybe one of your assumptions is that you need to change careers to make more money, get a better work schedule, or to find a job that you really enjoy.  All those things could be true but until you confirm or invalidate them it’s possible that you could be doing the (wasted) work to switch careers when what you really want could be obtained with your current skill set or industry.

If you do find you need to change careers the next step could be to test your assumptions about internships, part-time jobs, and volunteer roles. There’s always something else about your life you can test.

If you think you could avoid wasting time and money while in hot pursuit of something you’re not sure about then I’d definitely suggest you read more about lean principles. Here are two articles that can help you get started:

Living With No Regrets

I’m sorry to say there is no secret formula to being able to live regret free. When I started this site 8 years ago I knew that I wanted to address the importance of managing your money wisely while also using your money as a tool to have a good life. Ironically I put so much time and effort into running the site that I probably missed out on some things in life. I don’t regret publishing Money Smart Life over the years but there are some things that I wish I’d done differently.

Looking back on my 5 suggestions for living with no regrets, I realize that I’m not great at many of them. I’m still in the process of transitioning from work-a-holic to a guy who can stop and smell the roses.  I’m still figuring this out so I’d love to hear any comments or tips you can share that have helped you make better decisions and left you with fewer regrets.

Obviously making mistakes is human and mistakes help us learn.  We’ll always have some regrets but hopefully these tips can help you avoid regret for the really important things in life. Please share your experiences, suggestions, or tips in the comments below!


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Ben Edwards, the founder of Money Smart Life, saved up enough to buy a Nintendo back when he was 12 years old. When he used the money to buy shares of Wal-Mart stock instead, he knew he wasn't like the other kids... His addiction to personal finance has paid off for his family and now he's helping you to afford the life that you want. Check him out on the web at Google Plus, Twitter and Facebook.

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4 Responses to How To Live With No Regrets

  • Mark @ Debt-Free Mormon

    Nice article. I’ve read many of your articles, never commented, but just subscribed so i can get instant updates. Always appreciate reading from other peoples experiences. Thanks for the encouragement! Keep it up!

  • Stephen Brian

    Thanks Again for New Article. I Really Enjoyed your Article. Thank you So Much for your Writing. Keep up it.

  • Ashley

    Wonderful article Ben. So insightful and so true. Thank you for sharing this with us. I am deeply sorry to hear you had such a scare but know events like that can really help put things in perspective. The realization of how short life can be can enable you to identify what’s most important and prioritize accordingly. Please know I’ll be praying that you have perfect health from here on out with no more scares. I’ll miss seeing you at FinCon and hope you have a wonderful time with your family that weekend!

  • Glen Craig

    Great article! So many people spend so much of their time regurgitating how good the past was without making the present the best they can. Glad you’re still with us Ben.