Repeatedly Ask Yourself One Obvious Question to Avoid a Life of Regret

Oprah’s simple secret to a regret free life.

“Every mistake I’ve ever made is because I went outside of myself to do something for somebody else that I should not have. To please them. Just for the purpose of pleasing them.” — Oprah Winfrey

When asked what we want to do with our lives, many of us sound like Allie at the end of “The Notebook” when Noah shouts, “What do you want?” and she sobs, “It’s not that simple.”

But what if living the life we desire is that simple, even if it doesn’t feel like it most of the time?

At some point, whether it’s after high school, multiple college degrees, or once you’ve reached the top of a career you’re not sure you wanted in the first place, every one of us must confront a pivotal question:

What do I want?

In that moment of reckoning, we could all use some passionate encouragement from a young Ryan Gosling,

“Would you stop thinking about what everyone wants? Stop thinking about what I want, what he wants, what your parents want. What do YOU want? What do you WANT?” — The Notebook

Your ideal life trajectory may not always be clear to you, but you often have a sense of what you desire in the present moment. That’s all you need, a starting point.

Your heart may lead you in different directions over the years, and you may never understand your final destination, but you have to trust the journey you’re on. You were made for it, and it for you.

That’s Oprah’s key to a remarkable life, to believe what you want isn’t a mistake. Turning away from it is.

But what does it take to be fearless in the pursuit of your passions? How can you protect your dreams from relentless voices of doubt?

I won’t pretend to have all of the answers, but here are three ideas on how you can embrace Oprah’s secret to a regret-free life. It starts with a stubborn commitment to what you want.

Step #1 —Decide you’re the only person who knows what’s best for your life.

Most of us love the idea of having free will but never take advantage of it because we fear the consequences of our choices.

What if we choose wrong?

To avoid the responsibility of our failures, we look to gurus, mentors, and often our parents to guide us. If someone else chooses for us, we can bask in our triumphs without accepting true responsibility for our frustrations.

The problem with this approach is you are the only person who knows what’s best for you. My mom dreamed I would become a CEO, my dad thought I would make a great attorney, but I opted for a degree in Psychology then ran off to teach English in Italy.

My choices didn’t make sense to anyone but me, but I can live with my decisions happily because I had complete control in making them. Following what someone else wants for your life may feel like the easy way out, but it’s ultimately the path of greatest resistance.

We have to carve our personal paths through trial, error, patience, and persistence. Finding the right direction feels intimidating, but you already have everything you need to make the best decisions for your life.

Consider this: If you had one dose of Liquid Luck, guaranteeing anything you tried would go your way, what would you do?

Go do that. Trust your dreams have been gifted to you because you can and will accomplish them if you dare to try.

Step #2 — Find your cheerleaders.

Ultimately, you have to believe in yourself, but we all have times when our confidence wavers. It’s in those fragile moments when you need at least one person to remind you of your capabilities.

Plenty of people will tell you why you can’t achieve what you set out to do. Take my sister’s high school drama teacher, “You aren’t pretty enough to make it Hollywood.” Or hear my AP literature professor, “Don’t major in English unless you’re trying to end up working at a high school.”

These types of people trample dreams before they’ve hit the dirt, ripping fruitful seeds from the soil without giving them a moment to sprout. These are not the voices of “reason” you want to surround yourself with.

Instead, find people who will assist you in watering anything you find the courage to plant. You don’t always need someone to believe in your vision, but you do need someone to believe in you.

Step #3 — No plan B.

“There’s no reason to have a plan B because it distracts from plan A.” — Will Smith

Having an idea of what to do if everything goes wrong can seem like the responsible thing to do rather than figuring things out as you go. While having a backup plan provides a sense of comfort, there are a couple of problems with focusing on a plan B.

One, as Will Smith says, plan B distracts from plan A. Second, it assumes failure before you’ve taken the first leap of faith.

When I decided to move abroad, I didn’t have a plan B. Honestly, I’m not sure I even had a plan A. However, I did have a step one: book a plane ticket.

Every life-changing transformation starts with a simple action. It’s pointless and even counterproductive to try and anticipate every possible outcome and pre-plan solutions for fictional problems.

As uncomfortable as it is, you don’t know what will happen until you start. If you get stuck planning for what could go wrong, you’ll have limited energy left for making things go right, or even starting. The relationships you nurture grow, the projects you focus on flourish, and the path you run down becomes your life. If you travel full force in one direction at a time, you won’t have to take as many detours.

Turning away from your inner compass to impress, please, and appease others is the only mistake you should avoid and the one type of failure worthy of your fear.

Oprah’s key to living a regret-free life is to trust what you want for your life is not a mistake. Straying away from your intuition for the approval of others is the only way you can end up on the wrong path.

We all wanted something before someone said we couldn’t have it. But what if we can? What if you already know what to do and you only have to trust yourself long enough to do it?

Your desires serve as the ultimate navigation system, revealing personalized step by step instructions for your most fulfilling life. Trust what you want will never lead you astray.

Because it won’t.

More Medium? Get unlimited access here. Your monthly membership fee directly supports me and all of the other writers you enjoy. Thank you!