Adventure is a dangerous word.

To some, adventure implies that you must be wielding a sword, hiking Mount Everest, or risking death at every turn. But what if life could be an adventure? What if you could get past playing it safe and live a life of adventure?

What would that look like for you? When you are old and dying, what would a life well-lived, an adventurous life, look like for you?

Life of Adventure
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My wife, Tara, and I set our family goals this past week.

Some were short-term. Some were long-term. Most were safe. Most were goals that if we achieved them, we’d be thrilled. If we missed, oh well. For the most part, they were relatively mundane, like so many goals that we all set.

Pay off mortgage in three years.

Save for two cars.

Remodel basement.

New landscaping on our property.

All worthwhile goals. All requiring us to stretch and even sacrifice to achieve them.

But where was the dreaming? Where was the list of things that we’d look back on and go “wow, we did that, didn’t we?”

No one has conversations like this in old age:

Husband: “Sweetheart, do you remember when we got the new landscaping on our property?

Wife: “Of course, Dear, I remember it like it was yesterday. But, I couldn’t sleep last night because I was thinking so much about the time we remodeled the basement. Oh, those were the days.”


What happened to dreaming big? What happened to doing crazy things that most people never dare to do? Isn’t that what we were made to do?

3 continents

Then we added another goal:

Visit 3 continents by 2017.

As soon as we set that goal, the conversation seemed to turn. We dreamed about big things again. We talked about almost unimaginable things like they were definitely going to happen.

We took one small step towards living a life of adventure. We broke away, if but for a brief moment, from the unremarkably average life.

How to be unremarkably average

Chris Guillebeau wrote in his book The Art of Non-Conformity a list of 11 Ways to be Unremarkably Average. Number 4 was:

Go overseas once or twice in your life, always to somewhere safe like England.

The rest of his list is below. If you want to be unremarkably average, follow these 11 suggestions. If you want to be remembered, if you want to leave a legacy, and if you want to live a life of fullness and joy, you must break out of the unremarkable mold.

You must set big goals, have big dreams, and decide, once and for all, that you will look back on life and say, “Wow, that was an adventure,” not “Wow, I sure felt safe.”

That’s what Tom Preston-Werner, the founder of Github wants. He is dedicated to living a full life, a life of adventure, a life worth remembering.

“When I’m old and dying, I plan to look back on my life and say wow that was an adventure not wow, I sure felt safe.” ~Tom Preston Werner
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What about you?

What about you? Are you going to choose to continue to set reasonable, mundane, unremarkable, and unremembered goals?

Or…will you stretch yourself? Will you choose to dream bigger, set loftier goals, and live a life that you and others will remember?

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Do you plan to look back on your life and say, “Wow, that was an adventure” or “Wow, I sure felt safe?”

The choice is yours.

Here’s Chris Guillebeau’s full list of 11 Ways to be Unremarkably Average. Which ones most apply to you?

1. Accept what people tell you at face value

2. Don’t question authority

3. Go to college because you’re supposed to, not because you want to learn something

4. Go overseas once or twice in your life, to somewhere safe like England

5. Don’t try to learn another language; everyone else will eventually learn English

6. Think about starting your own business, but never do it

7. Think about writing a book, but never do it

8. Get the largest mortgage you qualify for and spend 30 years paying for it

9. Sit at a desk 40 hours a week for an average of 10 hours of productive work

10. Don’t stand out or draw attention to yourself

11. Jump through hoops. Check off boxes.

Stay tuned tomorrow as I share why I hate SMART goals but love DREAM goals. Be sure to subscribe to my RSS feed or get posts via email (and get my free book as a bonus) so you don’t miss it.

Which life do you choose? The remarkable or the unremarkable? The adventurous or the safe?

15 thoughts on “Want to Live a Life of Adventure? Follow this Tom Preston-Werner Quote

  1. Kirbie Earley says:

    Well this was an eye-opener at 7:00 a.m. on a Monday! As someone who teaches goal setting workshops myself, I can truly appreciate this, and draw a lot from it! You’re right. I always tell people when they begin to dream big, but I’m not sure I put enough emphasis on it!
    I am travelling to France in a few weeks – alone. I have been asked to speak on innovation at a conference there, so my second week there will be full of people and a schedule, but my first week is mine and I am so excited. I can’t decide what I want to see or where I want to go exactly. I have a ‘city pass’ and I just can’t figure out how to use it!!

    I like your list of 11 – it tells me that the things I am doing have me on a good path, but it also tells me that I can dream bigger. Finish the things on that list that I have started – or do them even better, dream of other places to go, things to do. Thanks for the reminders on what life is all about.

    1. Matt McWilliams says:

      What a great opportunity. Live it up Kirbie!

  2. Great post Matt. I am currently working are #3 and #4 so that I am not stuck in #9. Which ones are you working on today?

    1. Matt McWilliams says:

      #7…getting there though

      1. Kirbie Earley says:

        me too!

    2. Kirbie Earley says:

      I did #3 – it’s hard as an adult, but you can do it! Best of luck to you!

  3. Let's Grow Leaders says:

    Inspiring post. I want to give a TED talk and then be on the Today show. I’ve already been to a bunch of continents, Asia is next on the list. Im a BIG believer in dreaming BIG.

    1. Matt McWilliams says:

      Love those goals Karin!

      What’s your favorite continent and why?

    2. Jana Botkin says:

      What subject do you want to give your TED talk on?

      1. Let's Grow Leaders says:

        Authenticity in leadership

  4. Adventure, traveling and experiencing new things is the spice of life! Awesome goal of visiting 3 continents by 2017. Here’s my challenge to you: why wait until 2017?

    1. Matt McWilliams says:

      Mostly it’s just the order of goals. There are a few other things we want to do first like visit Costa Rica (same continent), take Tara’s mom to Hawaii, and have more kids 🙂

  5. Jana Botkin says:

    I’ve been thinking about learning another language for 7 years. . . could have been fluent by now if I’d only started back then. Sheesh. Still wavering – Spanish, because I have a head start and it is common around here or French because it seems so stinkin’ hard and would really be challenging? Maybe I’ll just see which one costs the least on eBay (Rosetta Stone)! Now there’s a thoughtful way to make a decision – the cheapest!

    1. Matt McWilliams says:

      It’s better than not making a decision for sure 🙂

  6. Zechariah Newman says:

    Great post Matt! Easy to get comfortable and average for sure.

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