Play to Win


Bronnie Ware worked as a nurse for seriously ill people for many years, often being with them just before they died. In her conversations over the years, she noted that people in her care told her they had the same types of regrets. She wrote a blog post about it called “Regrets of the Dying.”

[footnote]Regrets of the Dying[/footnote]

The most common regret of the dying: “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

Translated: “I wish I had played to win, rather than not to lose.”

When you live the life expected of you, it means you fear losing. You don’t want to lose respect, your reputation, or your image. When you try not to lose, you minimize your risk and reward.

Life Brings Risk Automatically

The phrase “life’s too short” exists because people understand the significant inherent risk of being a human being on Earth. There’s no way to hide from all dangers, especially from things we don’t fully control like disease and our mortality. 

Thinking broadly then, our lives are already saturated with risk! If we’re risk-laden, but we’re not putting ourselves in a position to acquire rewards, then we’re not playing the game correctly. But this isn’t a call to skydive (unless you want to do that), this is a call to practical risk-taking. It’s a call to take chances with the one chance we’ve got.

What Risks to Take

1. Invest

Don’t hide your time and money under your mattress.

If you have extra money, invest it in the stock market. It doesn’t matter if you think the world economy is going to collapse. You can invest your money in such a way to profit from that. You can invest in any industry, any country, any style. You can buy bonds. You can invest in real estate. There are so many ways to make your money grow, and while these methods come with risk (some of them very low risk), they can come with significant rewards as well.

If you have extra time, invest it in yourself. Buy books and courses to learn new skills. Exercise to build a stronger, healthier body. Practice communicating, playing sports, and playing music. How cool is it that we can become better at anything just by practicing? Take advantage of it! Investing in yourself is extremely low risk and it brings a very high reward.

Another way to spend extra time wisely is by buying experiences, which have been shown in studies to make us happier than possessions. I like the experience of traveling, so if I have the time and money to do so, I’d be CRAZY not to do it as frequently as possible. And yet, I’ve hesitated at times for various (invalid) reasons. That’s why this is on my mind, and also why I booked a cruise today that leaves in 6 days.

I invested a huge amount of time and money in my latest book, Mini Habits for Weight Loss. It’s risky, but so far, such investments have paid off very well for me.

2. Do What You Really Want, Not What Seems Easiest and Safest


Doing what you want is always a risk. It might seem odd to the people around you. You might fail. But so what? Life is too short and too perilous to worry about a short-term failure. Just like those people on their deathbeds, you probably won’t regret what you did do, only what you didn’t do.

Sometimes I hesitate to travel places because I think it’s safer and easier to stay home. But then I think about my time in Thailand just earlier this year. I rode on a scooter with crazy Thai drivers and made some memories that I’ll never forget. That choice and that trip were riskier—it’s only because of my natural remedy prowess that I staved off almost-certain food poisoning there—but my goodness it was worth it! It was one of the best experiences of my life!

The caveat to this one is that you need to remain smart. 

3. Don’t Wait for Anything or Anyone

Waiting is the worst. The very idea of waiting for something means you’re wasting precious time in a short life! If you literally have to wait for something like a planned trip, find ways to invest your time wisely before that happens. This is something I’m pretty bad at doing currently. I was frequently “bored” while Mini Habits for Weight Loss was being edited. Terrible. I’m going to practice and get better at it.

And just to clarify, wise time investment includes breaks and entertainment too. I love to work (Wow! Did I just say that? That’s proof of the power of habit formation. My subconscious went from loathing work to enjoying it.), but nothing is better than play!

The only way to win is to try to win. That statement is not as obvious as it looks. Put in another way, you will only win if you’re intentionally trying to win. Anyone could say, “Yeah, of course I’m trying to win the game/my goals/life/etc.” They only mean it if they have a specific plan, a strategy to make it happen.

Invest in yourself to grow. Invest your money to make it grow. Go places. Pay for experiences if you can afford them. Don’t look for permission. Don’t wait for anything. You’re already living a risky life because you’re on planet Earth. Go get the rewards!

What’s your next move, captain?

If you want to invest in your health, I suggest reading Mini Habits for Weight Loss. You won’t find a smarter or healthier way to lose weight.

It's Free to Subscribe

Free book - 10% Off Coupon - Newsletter

Share this article

Shopping Cart

Subscribe for

Updates & Gifts!

No spam. Easy unsubscribe. Life-changing newsletter!


Subscribe for all bonus content

I send my newsletter every Tuesday morning at 6:30 AM.


Instant Access


Read Part One of

Mini Habits

500,000 copies sold. 21 languages.

This book can change your life.

Start reading it now for free!

No thanks


You will also be subscribed to my excellent newsletter.

Unsubscribe easily anytime.

Scroll to Top