Yesterday I was editing one of our recent Youtube videos and came across a clip of our RV trip in Japan.

While watching Ellie and Eli run around a campsite in front of Mount Fuji, a thought occurred.

I have no regrets.

It wasn't just this literal thought that came to me, but more so a subtle feeling that we are living a life optimized for little to no regrets.

I don't believe we'll ever regret over-indexing into family time while our kids are young. I don't believe we'll regret taking them to see the world.

In today's newsletter, I wanted to share some of the mental frameworks we've used to strive to live a life without regret.

Before getting into the newsletter, I also wanted to share our two latest Youtube videos with you.

Video #1 Driving an RV in Wales was a bad idea​

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We were TRULY not prepared for the roads we experienced in Wales. To put it mildly, we drove a motorhome around back country roads that looked more like golf cart paths than actual roads. It's the most stressed I've ever been watching one of our videos. I still can't believe the roads we ended up on in our motorhome rental!

Video #2 Visiting the Wrexham Racecourse​

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After experiencing some wild roads, we made it to the town of Wrexham. I've been following the documentary series from Ryan Reynolds and Rob McElhenney who have been working to turn around this football club. If you want to see me geeking out about my first European football club visit, you can watch it here.

Okay, onward to today's email.

How to live a life without regrets

#1 Notice when you are using the word "should" to justify a decision

In 2014 Alyssa and I had a decision to make. Should we stay the course in our (first) jobs out of college once we were married or quit to travel the world?

Of course, these weren't the only two options. But they were the only ones we were talking about.

I felt torn.

I should probably be putting my degree to work and helping to grow this startup I recently joined. I should probably stick with a consistent job now that I'm providing for my newlywed wife.

For a while, I went back and forth.

Ultimately, the tipping point came when I asked myself a question.

Is there a chance I might regret not traveling while we are young?

I wasn't positive, but I felt there was a chance I could regret it. We decided to go.

Not only do I have no regrets from this year of travel, I have so much more gained.

Alyssa and I gained skills in video and writing that we didn't have before. We gained the confidence to work through challenging situations. Most importantly, we realized we make a great team and can get through tough situations as a unit.

Looking back, the word "should" has a way of nudging us into things we think society wants us to do. We should stay the course or do life in a traditional way.

But on the opposite side of the word should is another path.

Doing the thing that scares you. Doing the thing you know you want to do but feel as though you shouldn't. A lot of times we're making this decision because of the view or judgment of others (maybe the collective of a crowd or an individual person).

Instead of doing what you think you should do, strive to do what you feel is actually right for you. Do the scary thing.

#2 Realize there is no perfect time to do anything.

One of my best friends said something to me I'll always remember.

He said, there's never a perfect time to travel.

When you are young you have the energy and the time, but not the means. When you are middle-aged you have the means and the energy, but not the time. And when you are old you have the time and the means, but not the energy.

No matter when you decide to jump in and go for it, the timing will never be perfect.

Or as Tim Ferris says in his book 4 Hour Workweek:

I believe this is true for more than just travel. It's true for any major thing we want to do in life.

In 2019 we booked our first trip to Europe. We purchased the flights a few months before Ellie was born. The Delta agent asked for our daughter's name and I told her we didn't know yet. She laughed and said to just add it when we the baby was born.

In retrospect, taking a four-month-old across Europe was probably not ideal timing. Alyssa and I were sleep-deprived and running on fumes.

But we decided to go anyway. Why? Because we wanted to.

Was every moment easy? Heck no.

At one point while in Venice we left a window open and Ellie was attacked by mosquitos. Another day we lost a pacifier in the canals and endured a massive freakout while everyone stared at us.

But we also experienced magical moments too.

We found a gondola ride that took us up to a mountain peak overlooking the Dolomites. We tasted our first Italian gelatos and pizzas and fell in love with the country. We met friends in Tuscany who later invited us to come back and spend a month nearby and ride a bike across Italy (which I did last year).

I'm not saying it's right or even possible for everyone to go travel with a baby.

For us, we knew that the timing wasn't ideal being new parents to an energetic baby. But the timing would never be perfect. So we went. No regrets.

#3 Think of death.

We spend a lot of our lives consciously trying to avoid the idea that one day we will die. Ironically, one thing that helps us to live is to think about this day.

One day, if we are lucky, we will live to be old and then pass away.

A meditation I started doing over ten years ago is to imagine myself at 80 years old. I think about how my body will look and how my days will look. I think about how I'd like to be spending my time with Alyssa. I think about my life, the things I did and the kids I raised.

This practice of thinking about the end is one of the most powerful and easy ways I know of to live without regret. It becomes very clear in a few moments of this thinking what is important to us and what isn't.

#4 Be an "I love you" slut (pardon the language).

I tell everyone I love them. All the time. My kids. My friends (new and old). My family.

Because it's true.

I want the people around me to know what they mean to me. I don't know what tomorrow will hold. If I lose one of them before telling them the difference they made in my life, that would be a huge regret.

#5 Live your authentic life.

In a famous blog post turned book called Top 5 Regrets of the Dying, Bonnie Ware shared common regrets from people on their death bead.

The number one regret was:

When I first heard this I thought, "Sure, that sounds great."

But the more that I think about it, the more it resonates with me.

It's relatively easy to live a life that looks great on the outside but doesn't feel good on the inside. We have people who affirm us and tell us we are on the right path or the right career and it feels good for a moment.

The problem is when the outside metrics don't align with the inside ones.

Warren Buffet calls this our "inner scorecard."

Does what we are doing on a day-to-day basis actually feel like winning? Or are we only doing it because it's what we should do or what we're expected to do?

The tricky part of this conundrum is that only one person can be the judge of whether or not something feels good.

You.

It's my goal to live a life with no regrets. I want the same for the people closest to me as well as anyone who is reading this email.

If you've made it to the end, thank you for reading this. I hope it inspires you to not hold back from doing the things you know you want to do in this short and precious life.

-Heath

PS I was recently asked by a reader if they could hire me to do a "coaching session" with them for their business. I don't aspire to be a professional coach or have a coaching business, but I enjoy talking about business or startup topics with others.

So I've opened up a few time slots this next month for anyone who feels I could provide value or clarity for them in their life or business. We could discuss startups, selling a business, or anything you want.