The Antidote to Regret: Kimberly Rich (Transcript)

To lead a fulfilling regret-free life, you just have to be willing to do one thing. You have to be willing to be bold.

When I first had this realization that boldness was so integral to finding fulfillment, I devoted my life to spreading this message. I read book after book and attended seminars and ultimately I started coaching people on how they too could embody a bolder lifestyle.

I’ve spent the past two years interviewing inspiring individuals for my podcast, people who have been able to create adventurous regret-free lives based on this one common theme: embracing their inner boldness.

But before I tell you how you can start to be bolder in your life, I need to tell you how I got to this place. Because trust me, I was not always living this way.

Like most people in our society, I believe that life looks like this. You go to high school, then college, then you get a job, find a mate, buy a house, make a baby, and live happily ever after.

It seems pretty easy, right?

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Well, I gave it my best attempt. I graduated college in 2008 which as you may remember, was the best possible time that one could hope to be getting a job.

So to be safe, I took the first job that was offered to me and it ended up being the exact job I said I would never do. So for two and a half years I made cold calls to government employees and I’m sure that they were as thrilled about it as I was.

About the same time that I got my dream job, I also got into a very safe relationship with someone who was all wrong for me. We did a couply things. We went on vacations, happy hours, nice dinners, but there was little to no passion.

And I stayed with him for a year because I was too scared to leave.

Well, the turning point came like most big shifts in our life. Slowly… and then all at once.

I started taking risks first by leaving the relationship and then eventually the job, and then at my next employer I took another even bigger risk by proposing an international remote work agreement, something that no one else was asking for.

But ultimately the biggest shift came when I read a little book called ‘The 4-hour work week’. After reading Tim Ferriss‘ book, I had hope and I stopped believing that I was stuck, feeling overworked and under traveled for the rest of my life.

I stopped believing that I was stuck driving an hour long commute every day for the rest of my life.

And in 2013 just four months after reading this book, through a series of very bold decisions, I quit my corporate job and I moved overseas. I spent the next two years traveling all over Europe and Southeast Asia working anywhere that had a decent Wi-Fi connection.

I studied things like internet entrepreneurship, which eventually led me to personal development, which led me to my business, The Bold Life Movement and ultimately to the stage.

What I hope you can see though is that this was a process that took time. The bold moves that I made evolved over the years. With every risk that I took, my comfort zone expanded, and with every bold action I eliminated the potential for those future feelings of regret.

Today we’re going to talk about how you can do the same. And I’ll share with you three secrets that I’ve uncovered through hundreds of hours of research and interviews and years of personally living these truths myself.

Ask for what you want

So to avoid regret, number one: Ask for what you want. The quickest and easiest way to start getting what you want is to have the audacity to ask for it. This may seem so obvious and so simple, but for some people asking for what they want is as terrifying as getting up on stage in front of a large crowd.

But the truth is that we don’t know what seemingly out-of-reach things can start to become within our grasp until we start to ask.

I’ll share with you a personal story. My mom somehow became a huge fan of an Australian-based TV show and fortunately the producers of this show know that without their fans it just wouldn’t be as successful.

So throughout the year they host these different events where the fans and the actors can come together. She has taken full advantage of this and flown all the way to Australia more times than I can count.

So for her birthday last year, I thought it would be a really great gift if I could get the actor on the show to send her a happy birthday message. I knew it was a big stretch, but I figured, what do I have to lose?

So the day before her birthday, I logged into Instagram. I opened a private message to him. I sat there for about 10 minutes with my finger hovering over the record button because I was very nervous. And then eventually I recorded a video and hit send.

The next day, I couldn’t believe when his message came through. Not only had he actually responded to me, but he had sent the most thoughtful video ever. Fortunately, she and I happened to be Skyping at the time and I was able to capture her reaction. Take a look.

<Kimberly Rich plays a video>

Off screen voice: Happy Birthday! Um, sorry I’m just getting the hang of this… video thing on Instagram, but… I’m having a wonderful day. I miss you… and it’s been not the same since you’re been back. It’s always, always awesome to have you here.  So much fun. You know, and just all throughout the distance and ’39 steps’. Love to get your way sometime… And love to have you back sometime. So, have a wonderful day and… All the best… Big Hugs and Kisses.

Kimberly Rich: I just asked him.

Mom: MY GOSH!

<Video ends>

She’s so happy, right? Hopefully you can see how being bold enough to ask her what you want doesn’t just benefit you, It can benefit the people in your life too. The interesting thing is that most of us underestimate how likely people are to say, ‘YES’.

A recent study at the Stanford graduate school of business illustrates this point really well. They had participants go out with the goal of getting five strangers to complete a short questionnaire. They also asked the participants to estimate how many people they’d have to approach to reach this goal.

Well, most of the participants overestimated how many people it would take. In fact, they thought it would take twice as many as it did. To get those five signatures on average, participants only needed to ask about 10 people. That’s a 50% success rate, which is comparable to what had been seen in other studies.

So if you are 50% more likely to get what you want just by asking, why would you forego that opportunity?

It could be as simple as asking the Barista to fix your coffee order because they messed it up or asking for an upgraded seat on your next flight. It could be asking your boss for the afternoon off, simply because you need a mental-health day.

Having the audacity to ask for what you want doesn’t make you an asshole. Being bold doesn’t make you a bad person.

At the end of every podcast episode, I ask my guests to tell me what their definition of leading a bold life is.

One of my favorite all time responses came from a former lawyer turned travel writer and food blogger Jody Ettenberg. Jody said: “Being bold is different from being brash…” There’s a subtlety and a roundness to being bold that is classy.

It means being unapologetic about the things that you love in life. Isn’t that great? It’s not aggressive. It’s confident. If you’re not willing to ask for the small things, how are you going to be willing to ask for the things that really matter?

Today, it’s a better table at a restaurant, but next year it could mean having the guts to ask your spouse to move your entire family across the country for a job that you really want. Too often we forego asking for what we want because we’re scared of being judged. We’re scared of imposing or we’re scared of being told no.

Newsflash: If you don’t ask, the answer is always NO, and here’s a pro tip: Sometimes the best possible time to ask is after you’ve already heard that initial NO.

One of my favorite personal examples of what can happen when you refuse to take ‘No’ for an answer came when my dad was discharged from the U.S. Air Force halfway through officer training school.

Now you should know that my dad spent his entire life preparing to be a pilot in the air force. He got his Pilot’s license at 16. He graduated college in three years with a degree in aviation and he aced all of his aptitude tests.

But halfway through training they faced an overage of officers. So they changed their policies and made some cuts. Well, my dad being a very reasonable man, decided to write a letter to the person in charge of the entire military. If you don’t know, that person is the commander in chief sometimes called the President of the United States.

His bold letter to President Ford earned him a phone call from The Pentagon just a few days later. And within four years my dad had been reinstated. He had completed officer training school and he had earned his wings. He spent the next 23 years serving his country and living out his dream.

What dream are you giving up? Because you’re so willing to accept ‘NO’ as the answer or worse, not make the ask at all.

To avoid regret, you have to be bold, so ask for the little things. Ask for the big things. Ask for the things that no one else is asking for. You never know what people will be willing to say yes to until you give them the chance.

Think different

The second way to avoid regret is to think different. In the 90s, Apple nailed it with their ‘Think Different Ad Campaign’ because they weren’t just improving the way that we listen to music or the way we use computers, they were creating an entirely new way of doing it.

They were willing to think outside the box and to challenge the status-quo to get what they wanted. And ultimately if you want to get what you want, you have to be willing to do the same.

Last year, one of my favorite authors and bloggers, Chris Guillebeau came through Austin on a book signing tour. I was determined to show him my appreciation for his work when it came time for him to sign my book.

Now I knew the best way to do that was to just be myself and to accept that that meant being a bit different from everyone else in line.

For me, the most authentic form of appreciation is a handmade gift. So I made Chris a watercolor illustrating all the ways that his work had impacted my life. Naturally, I was terrified to give it to him because I didn’t want him to think I was some wacko fan.

But when it came time for him to sign my book, I jumped up. I was the first person in line, too nervous to wait, and in the end he was so touched and so taken aback by the gesture that he ended up asking me for my contact information.

By thinking differently about that opportunity, I was able to leverage it far beyond what I ever could have imagined. Since then, Chris has been a guest on my podcast and last year he even invited me to host the session at his annual conference.

To avoid regret you have to be bold. If you want to create opportunities in your life, be willing to think differently, be willing to challenge the status quo and be willing to stand out.

Trust your gut

The third and final secret to avoiding regret is to trust your gut. Only you know what is best for you. And if you want to lead a fulfilling and authentic life, then you need to be willing to fulfill your dreams and desires no matter what anyone else in your life thinks, says or would do.

Let me share with you a personal story that may surprise you.

When I was in high school, I used to spend a lot of time on AOL instant messenger. So much time in fact that I ended up meeting a long distance boyfriend and falling in love.

We lived 3000 miles apart on opposite sides of the country, but because my dad was a pilot, I had flight benefits and we were able to make it work.

Keep in mind though, this is pre-Tinder, pre-online dating and I was in high-school, so this was very taboo for the times. But we had connected over instant messenger and fallen in love over the phone and we even took it as far as going to prom together.

When we went off to college, things ended on somewhat of a sour note and for years I thought he hated me and didn’t know why. For years I want a closure because I’m a human.

Fast forward to 2015, 10 years later I found myself in his hometown attending a conference.

This was the first time I had been back since I was 17, so I looked him up. At first I took the usual routes. Facebook, found nothing, Instagram nothing. Twitter, LinkedIn, Google, all dead ends. According to the internet, he was virtually nonexistent.

It wasn’t until I found a single Google image posted by his then employer, did my luck search change, but there was no email address.

So I decided to pay him a visit at his office. If alarm bells are ringing in your head and red flags are flying in front of your face, that’s probably a very normal reaction. But I wasn’t concerned with being normal. I was on a mission.

I somehow convinced a good friend to come with me as moral support and to get myself pumped up. We blasted. I have the tiger in our rental car as we drove down the street to his office. I was completely terrified, but I also figured what’s the worst that could happen?

If nothing, it will make for a very good story. That unexpected drop-in ended up being one of the best things that’s ever happened to me. Of course, he was shocked, but he didn’t call the cops.

No. In the end, he was thrilled and we spent hours reconnecting. Any negativity he’d once felt was a distant memory. I knew in my heart that that reunion would be positive, but I never could have known how much it would change my life.

The story of that encounter ended up being the first blog post on my website- The Bold Life Movement, which has since turned into a coaching business, a podcast, and soon a book.

When your heart tells you to do something, listen. If the only thing keeping you from taking action is fear of judgment or failure or rejection, I encourage you to move through it because trust me, all of those people that you think are going to judge you, they won’t be around when you’re in your 70s or 80s looking back on your life wishing that you had seized those opportunities.

To avoid regret, you have to be bold. So whether it’s a new business, a new job, a new romantic partner, or an old one, trust your gut because believe me, you’ll never be able to please everyone else anyway. So if you’re waiting for permission, this is it.

No matter what the outcome is, action always breeds clarity. And failure is just another form of feedback. So remember that regret is a choice and that it’s avoidable.

So be bold enough to ask for what you want. Be brave enough to think differently. And always, always, always trust your gut.

Thank you.

Resources for Further Reading: 

Regret-Free Living: Bronnie Ware at TEDxGraz (Full Transcript)

Nothing to Regret – Small Bad Habits Cause Lifelong Regrets: Iman Aghay at TEDxStanleyPark (Transcript)

Life’s Way Too Short Not to Live Your Bucket List: Travis Bell (Transcript)

Owning Alone: Conquering Your Fear of Being Solo: Teresa Rodriguez (Transcript)

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