Member preview

“two women sitting at the back of the car” by Jorge Saavedra on Unsplash

How to Avoid Living a Life Filled With Regret

“The mass of men lead lives of quiet desperation. What is called resignation is confirmed desperation.” — Henry David Thoreau

My mom graduated from high school a year early. She graduated from college and got her masters degree in five years.

She did everything “right”- got the grades, worked hard, climbed the ladder.

She spent the next few decades as a highly paid consultant. She achieved the proverbial American dream.

She had the trappings of success–the brand new car, the wardrobe, and the credit card with a limit so high she could go on as many shopping trips and she wanted.

Everything went smoothly for a long time.

Then 2008 happened.

She lost her job and was unemployed for 18 months. She found work again, but it wasn’t a six figure gig. When an employer has to decide between a seasoned employee with credentials and a younger person who can do similar work for half the money they always choose the latter.

She did a hell of a job raising two delinquent sons. She was amazing at her work. She’s had the opportunity to travel and have interesting experiences.

But I don’t know if she ever found her calling.

She always mentioned wanting to start her own business. She was an Avon representative for a while and she loved it. She was great at sales and enjoyed owning her little empire. She gave that up to spend more time with us.

I can’t help but think she’ll have to look back on her life with a bit of regret. It hasn’t been a bad life. Just an incomplete one.

Many of us end up living “good lives,” but there’s still a hint of the “quiet desperation,” Thoreau mentioned. We have dreams that slip away, ambitions that fade, and develop resignation for our situations.

It’s not completely our fault. We’ve been brought up in a society that encourages us to throw our dreams in the garbage.


The Quicksand That Swallows Dreams Whole

We live in a society built on carrots and sticks.

You’re taught early on to seek validation from outside of yourself. Regardless of your uniqueness or individuality you’re all measured and processed the same way.

The carrots are the good grades and comments on your assignments from teachers. Like a part to a machine, you’re processed through the education factory until you’re an adult who can’t help but salivate over the carrot.

Why do you think people work at six figure jobs for faceless corporations?

Not because they love what they do, but because chasing the carrot is all they know. Keeping up with the Jones’s becomes more important than being ourselves and doing what we truly want.

“We buy things we don’t need with money we don’t have to impress people we don’t like.” — Dave Ramsey

Then there’s the sticks.

When you grow up you learn about rules, punishment, and failure. Your priority becomes avoiding punishment and failure instead of taking chances and expressing yourself.

You learn to avoid eye contact with the teacher when she asks a question you’re unsure of. You learn that falling below a certain percentage on an assignment makes you less than your peers. You learn to fear the judgement of those around you.

The conditioning continues right into adulthood. Instead of taking initiative at your job, you do what you can to not get fired. Instead of starting that business or writing that book you choose the “safe” option of going to a meaningless job.

Why? Because everyone else does it. The overarching theme, even above the carrots and sticks, is to be like everyone else.

An Unconventional Approach to Finding Meaning and Happiness

Positive thinking alone won’t get you far. In fact, some research shows that visualizing your success too much can make you feel like you’ve already accomplished something even though you haven’t.

Our negative emotions don’t get enough credit.

Do you want to be miserable all of the time? Of course not. But your negative emotions are often signals that something in your life needs to change.

You’re feeling stuck. You’re working in a meaningless career. You feel like the dreams you once had have slipped away. You could say “oh well,” and continue to live your life this way. Or you could be a little tough on yourself and decide you’re not going to give in to your circumstances.

Maybe you don’t need to “love yourself” if you’re not being the “you,” you want to be. Maybe you shouldn’t pretend life is rainbows and roses because your situation is “okay.”

Maybe it’s a good thing to have relentless drive and always want to push a little bit more.

There was a time where I seriously considered becoming a full on zen-Buddhist. I read a few books by the Dalai Lama and Thich Nhat Hahn. The thought of having no stress or worries appealed to me. I did yoga and meditated for hours every day. I was on the verge of moving to Tibet and living in a cave.

Thankfully the phase didn’t last. The tenets of eastern philosophy are helpful for finding peace, joy, and meaning. But personally, a life of “nothingness,” isn’t what I want.

Gratitude and contentment can be foundations or they can be masks. There’s a difference between building an action filled life on top of these emotions and hiding behind them to avoid doing uncomfortable work.

Becoming great isn’t comfortable. Increasing your skill in increments with no promise of a payoff isn’t comfortable. Doing what others won’t do to live how others won’t live isn’t comfortable.

Working towards an ideal future can be uncomfortable to start but leads to a more comfortable ending. Think of exercising. It’s uncomfortable while you’re doing it, but it leads to greater comfort throughout the day.

Sitting your ass on the couch is comfortable while you’re doing it, but doing it too often leads to general discomfort throughout your day.

Living a “normal,” life because other people equates to to sitting on the couch. You don’t feel stress in the short run, but the life of quiet desperation causes an ongoing mild stress.

Then one day it hits you. You’re 50 years old. You look back at your life and say to yourself.

“What have I done?”

The biggest regrets of the dying include:

  • Not doing what they truly wanted to do in life.
  • Being like everyone else.
  • Playing it safe.

But they can’t get the time back once it’s gone.

I’m not here to tell you what to do with your life. I’m here to tell you what can happen if you’re not careful.

I’m meeting you right where you are so I can ask you to think about it.


What About You?

I’ve had comments to previous posts I’ve written saying something along the lines of, “That’s great, but some people have to earn an honest living. They have kids and responsibilities. If everybody went after their dreams who would pick up the trash and serve us our food.”

I understand where they’re coming from. There are roles in society that currently need to be filled. A percentage of the population will always work in jobs they don’t like and suffer through monotony.

But why does that have to be you?

Why you do have to be the “normal,” one?

Why do you have to pick the “safe,” route?

Why do you have to put your dreams on hold and gradually slip into the quicksand of desperation and resignation?

You don’t.

I’m not trying to put you down. I’m trying to prepare you for what’s ahead.

If you continuing working where you’re working and living how you’re living, what will the next decade look like for you? Expand that out to the end of your life.

Maybe you’ll have gotten a few promotions, won an award, and receive a gold watch for your retirement.

But will you have lived?

Of course you should feel satisfied with living a life filled with good relationships. But relationships are only half of the equation.

The work you do is important. The path you follow is important. The legacy you leave is important. The gifts you were generously given are important.

I write because I believe in freedom. Freedom for you and I both to live the lives we deserve. Not in terms of money or fame, but in knowing we got to share our gifts as much as possible.

What gifts are you hiding? The world not only wants, but needs something from you. When will you make the decision to give it freely?

When will be the right time for you to start living life on your own terms?

One day I’ll buy my mom and brand new house and give her seed money to start her business. She’ll be in the Forbes 60 under 60.