25 Bits Of ‘Excellent Advice For Living’ That Apply To Adventure

drawing of a Planned Path vs. Other Interesting/Fulfilling/Life-Changing Thing


In 2020, Kevin Kelly wrote a post on his website titled “68 Bits of Unsolicited Advice,” which he’d put together for his 68th birthday. I read through it, found myself nodding along with his Tweet-length recommendations, loved it, and shared it in my weekly newsletter. This one was the second bullet on his list: “Being enthusiastic is worth 25 IQ points.”

The post was shared widely, first by people who were fans of Kevin Kelly, and I imagine later by people who hadn’t heard of him before but found the list to be insightful. I knew Kevin Kelly as the founding executive editor of WIRED, and the guy who came up with the 1000 True Fans theory back in 2008, and an avid backpacker and traveler. (TLDR; lots of people think he’s a pretty wise person.)

In a scenario that every online writer dreams of, a publisher decided the 68 Bits of Unsolicited Advice would make a good book, so Kevin Kelly removed them from his website, added 150 more bits of advice, and in May 2023, the book Excellent Advice For Living: Wisdom I Wish I’d Known Earlier was published.

My friend Mario mailed me a copy of the book back in April, and of course I blazed through it in a couple hours. But in reading it, I started thinking that many of the bits of advice are applicable to adventure, whether it’s big-A, expedition to some faraway mountain range Adventure, or little-a, let’s bike or hike to a new place this weekend adventure. So I started flagging them with Post-It notes, in order to compile a list. Here are 25 of them, with a few of my illustrations.

Tend to the small things. More people are defeated by blisters than by mountains.

drawing of size of mountain vs size of blister

Taking a break is not a sign of weakness but a sign of strength.

A vacation + a disaster = an adventure.

Acquiring things will rarely bring you deep satisfaction. But acquiring experiences will.

If a goal does not have a schedule, it is a dream.

A major part of travel is to leave stuff behind. The more you leave behind the further you will advance.

drawing of how much you leave behind vs how much you advance

Experiences are fun, and having influence is rewarding, but only mattering makes us happy. Do stuff that matters.

The greatest teacher is called “doing.”

Your enjoyment of travel is inversely proportional to the size of your luggage. This is 100% true of backpacking. It is liberating to realize how little you really need.

Always read the plaque next to the monument.

Ask anyone you admire: Their lucky breaks happened on a detour from their main goal. So embrace detours. Life is not a straight line for anyone.

drawing of a Planned Path vs. Other Interesting/Fulfilling/Life-Changing Thing

Looking ahead, focus on direction rather than destination. Maintain the right direction and you’ll arrive at where you want to go.

In preparing for a long hike, old shoes of any type are superior to brand-new shoes of any type. Don’t use a long hike to break in shoes.

For every good thing you love, ask yourself what your proper dose is.

Purchase the most recent tourist guidebook to your hometown or region. You’ll learn a lot by playing the tourist once a year.

Explore or optimize?
Do you optimize what you know will sell or explore something new?
Do you order a restaurant dish you are sure is great (optimize) or do you try something new?
Do you keep dating new folks (explore) or try to commit to someone you met?
The ideal balance for exploring new things vs. optimizing those already found is 1/3.
Spend 1/3 of your time on exploring and 2/3 on optimizing and deepening.
As you mature it is harder to devote time to exploring because it seems unproductive, but aim for 1/3.

pie chart of Exploring vs. Optimizing + Deepening

Hikers’ rule: Don’t step on what you can step over; don’t step over what you can walk around.

To have a great trip, head toward an interest rather than a place. Travel to passions rather than destinations.

Your flaws and your strengths are two poles of the same traits.
For instance, there is only a tiny difference between stubbornness and perseverance or between courage and foolishness.
The sole difference is in the goal.
It’s stupid stubbornness and reckless foolishness if the goal does not matter, and relentless perseverance and courage if it does.
To earn dignity with your flaws, own up to them, and make sure you push on things that matter.

The big dirty secret is that everyone, especially the famous, are just making it up as they go along.

The chief prevention against getting old is to remain astonished.

line graph of feeling of wonder as it correlates to feel of youthfulness

You choose to be lucky by believing that any setbacks are just temporary.

Measure your wealth not by the things you can buy but by the things no money can buy.

If you are stuck in life, travel to a place you have never heard of.

When making plans, you must allow yourself to get lost in order to find the thing you didn’t know you were looking for.

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