Three Ways To Minimize Dying With Regret
Must be a valid email address.
Password must be 8-64 characters.
Must be a valid phone number.
Recession incoming? Here’s how you can prepare.
Daily Capital
Home>Daily Capital>Legacy & Estate Planning>Three Ways To Minimize Dying With Regret

Three Ways To Minimize Dying With Regret

“Sam, you will regret more of the things you don’t do than the things you do,” said my friend and office mailman, Jack. I could see the sadness in his eyes as he quietly sat still thinking about all the things he should have done.

“I should have taken more risks. I should have tried new things. I should have planned my finances better. I’m 56 years old and I’ve got hardly any savings. This wasn’t the life I envisioned,” he continued.

Every afternoon for 10 years Jack and I would chat for five minutes about our respective futures. He was a frail fella who sometimes came into work with a bandaid on his bald head to cover the sunspots that gradually formed over time.

Then one day he stopped showing up. Jack, the kind man who made $33,000 a year and beloved by all was laid off. The financial crisis showed no mercy, not even to a loyal employee who cost the least.


2008-2009 is a time period that many of us would rather soon forget. But ironically, the financial crisis helped embolden me and several of my friends to take more risks. Going through the worst downturn ever and surviving made us realize nothing else could be as bad.

Ever since riding in the back of my parent’s friend’s Mercedes as a 7th grader, I’ve always wanted to be an entrepreneur. But I neither had the guts, nor the financial wherewithal to take such risk. I turned down an entrepreneurial opportunity to work in Shenzhen, China in 1999 for the “safety” of working in finance in New York City. But every year I worked, I wondered what my life would have been like if I took the left fork in the road instead.

Regret is one of the worst feelings ever. I should have just kissed her, was one regret that plagued me all throughout high school. I didn’t want to look back as a 70 year old and regret having never tried entrepreneurship, so I took the leap of faith in the spring of 2012 to do my own thing. It’s petrifying to go from making a decent income to making hardly anything for the first year. But I don’t regret the move one bit.

Here are three ways to avoid regret:

1) Provide maximum effort. You can fail due to brutal competition, unforeseen exogenous variables, or simply a bad idea. But never fail due to a lack of effort. Hard work requires no skill, therefore you are in full control of your work ethic provided you are an able bodied person. If you’ve truly tried your best, then regret will be minimized because you know that there was nothing more you could do. The regret won’t completely go away, but it will be small enough that it won’t send you into some dark hole.

2) Ask yourself what’s the worst that could happen. Once you understand the realistic worst case scenario, then everything else isn’t so bad. Almost everyone I knew lost 30%-60% of their net worth during the financial crisis. Even if you ended up selling everything at the bottom, you’re probably still standing and in better shape than you were before. Having an idea of the worst case scenario creates a backstop that helps eradicate fear. But there’s a likelihood that many other scenarios will happen instead. Come up with at least two different subpar scenarios and steps you plan to take to improve the situations. The more scenarios you can plan out, the more prepared you will be. Part of regret comes from getting blind-sided by circumstances that could be avoided with better planning.

3) Imagine yourself with only one year left to live. There’s a great line in the movie Inception where Saito asks, “Don’t you want to take a leap of faith? Or become an old man, filled with regret, waiting to die alone?” Life speed accelerates. Eventually we’ll realize the end is near and pontificate on all the things that could have been. Try projecting yourself into the future and understand what are the things you will most regret. Surely you will regret more of the things you didn’t try than the adventures you took.


Have a watch at how Jeff Bezos, founder of Amazon came to the conclusion of quitting his well-paying banker job mid-way through the year to start Amazon.

I firmly believe the older we get the more we will regret our inactions. We’ll start telling ourselves that we are too old to do so-and-so anymore. Even if we fail, at least we know we tried. There are countless naysayers who will criticize everything you do. Thank them for giving you the motivation to carry on. The reason why they make fun of you is because they don’t have the courage themselves to try.

Unless you are extremely lucky, nothing great is going to just happen to you. Take action, provide maximum effort, do your best to plan for the unknown, and hope for better days ahead. If she slaps you for trying to kiss her after the third date, if the Venture Capitalist rejects your one minute elevator pitch, or if the new job opportunity doesn’t work out, at least you know you tried. The sting of rejection only lasts a short while. Regret lasts for a lifetime.

Plan your finances with Personal Capital

Readers, what are your regrets? How do you minimize your regress and maximize happiness?

Photo source: Public Domain




The content contained in this blog post is intended for general informational purposes only and is not meant to constitute legal, tax, accounting or investment advice. You should consult a qualified legal or tax professional regarding your specific situation. Keep in mind that investing involves risk. The value of your investment will fluctuate over time and you may gain or lose money.

Any reference to the advisory services refers to Personal Capital Advisors Corporation, a subsidiary of Personal Capital. Personal Capital Advisors Corporation is an investment adviser registered with the Securities and Exchange Commission (SEC). Registration does not imply a certain level of skill or training nor does it imply endorsement by the SEC.

Sam Dogen is the author of the new personal finance book "Buy This, Not That: How To Spend Your Way To Wealth And Freedom." Sam has been using Personal Capital to keep track of his finances for 10 years. He is the founder of Financial Samurai, one of the largest independently-owned personal finance sites with over one million visitors a month.
Icon Close

To learn what personal information Personal Capital collects, please see our privacy policy for details.

Let us know…

This year, my top financial priority is:

Building my emergency fund
Paying off high-interest debt
Budgeting better
Saving for a short-term goal, like a vacation or new car
Increasing my investment contributions
Maintaining status quo - I’ve got this under control

Make moves toward your money goals with Personal Capital’s free financial tools.