Living Small, Living Simple, and Living Well

I would love to hear your comments, ideas, and thoughts on this. Leave your reply below.

I write this with coffee in hand, at 6:26 am, next to a campfire in the Black Hills of South Dakota. Ten days in the western part of this state have been on our annual calendar for over 30 years, and we consider it an essential recharge and grounding ahead of attacking the rest of the year. In some ways, my year is bookended by my Annual Review in December (and if you don’t know about the Annual Review, you’ll learn about it in six months), and this trip. They both serve the same purpose but in different ways: the goal is to help learn what is truly important.

This trip also naturally leads to time to think, analyze, contemplate, and write. And something has struck me hard in the last few days: the potent combination of living small, living simple, and living well.

Much of this bubbled up in my brain when we drove miles off the beaten track, found a ridge on a hill, opened up our chairs and table, and popped a bottle of rosé (which is where the photo of Spencer and Angela was taken). At that moment, I realized I have everything I could ever wish for. At that moment I had my family, an amazing view, happiness, a car full of food, and a glass of vino. At that moment, life brought me more joy than I’ve felt in a long time.

It got me thinking about why. What added up to this feeling of euphoria and gratitude? How can I replicate this in my life going forward?

It came down to three things: living small, living simple, and living well.

Living Small

Living small is about having a small footprint, a minimal impact, few needs, and curation of high-quality things that replace anything disposable or cheap.

It’s about having one great mug instead of a cupboard of hodgepodge. It’s about investing in good hiking pants and boots that last for years, instead of shopping based only on what’s on sale and replacing it every season. It’s about biking when you can, or walking if it makes sense. It’s about repairing items you own if they break or rip, and feeling the satisfaction that it wasn’t hard to repair in the end.

It’s about packing a lighter bag on a trip and knowing you’re going to be okay (or if necessary, you can always solve a problem along the way by whipping out a credit card).

It’s about carrying a music collection and a library in these amazingly powerful computers we carry in our pocket, reducing weight figuratively and literally.

It’s about buying meat and produce from farmers and roadside stands instead of on a tray of styrofoam at the big store.

It’s about having a small group of trusted friends that will have your back no matter what.

It’s about seeking a sunset and a view instead of a fancy-ass expensive dinner.

It’s about appreciating the little things every step of the way.

Living small is not a life of sacrifice.

Living Simple

Living simple is about systems that keep complications out of our lives.

It’s about keeping finances and investments streamlined and automated (read I Will Teach You To Be Rich, and follow Mr. Money Moustache).

It’s about always putting your shoes in the same spot so they are there for you in the morning.

Living simple is about making conscious choices to repel chaos and randomness and to definitely avoid the monstrous energy that social media can infect your brain with.

It’s about connecting with those you aspire to be more like.

It’s about knowing the direction you are heading, and the bigger goals you want to accomplish (while not going off-course by focusing too much on others and not enough on yourself).

It’s about realizing that a little bit of great food is better than a big pile of mediocre food (and it’s healthier for you).

It’s about making a short list of what you really want in life and figuring out how to make it happen.

Living Well

Life is too short. We only get one lap around the track. Living well is about consciously choosing to spend earned and banked time, energy, or money on things that will bring you joy in your life.

Part of “living well” is not to do it all the time (that’s living to excess) but rather realize the rare and appropriate moments to buy the fillet mignon instead of the top sirloin.

To recognize that the joy of a great play, concert, or musical deserves great seats to view it from (don’t cheap out when seeing your favorite bands).

To know that taking a trip to amazing places while you can, with people important to your life, will pay off in ways that have nothing to do with the money spent to accomplish it. A lifetime of memories for everyone.

Living well is having a small collection of very special bottles of wine to give you something to look forward to in the future.

Living well is popping those corks with intention and focus.

Where does all of this lead? I don’t know. It just struck me while sitting on the hill watching the sunset on the longest day of the year.

I would love to hear your thoughts on this.


  1. Absolutely brilliiant and lovely. I am going to save this one to remind me along the way. You are a connoisseur of wine and Life! I agree on all of it and totally embrace great seats for special events!

  2. This is so great. Scott and I try to do a lot of these things and it’s nice to see others finding joy in similar ways. Eliminating the clutter in many areas and knowing when to live well. So satisfying. Thanks… plan to share this with loved ones.

  3. For us, it has to do with gratitude. These are the “good old days,” when nothing is (terribly) wrong, when we wake up feeling lucky and smart enough to appreciate that. To love and be loved, to have enough, and remind ourselves to be aware each moment of the wonderful life we live.

  4. Love the theme of intentionality in how we spend time, resources, and energy. Thanks for the inspiration!

  5. Jason,
    We just returned from Burgundy- an amazing place- with people important to us- and we do feel much richer for the experience (and came home with a few bottles to look forward to). When you and Angela come to Oregon, we’d love to open a bottle with you and enjoy our sunset!

  6. Well stated. I would leave an image from our last few backpacking trips to Peru, the Windys, Sierras or CO, but it does not seem to be an option on this variant of WordPress.

    There is joy and wonder when you disengage with your routine and go out to beyond, wherever that may be, and just observe and feel. That joy gets me through the rest of the slog.

  7. Jason, Thanks so much for sharing this! You’re spot on, and your well-written reflections really brought it into focus. It’s hard to overstate how much a GOOD bottle of wine enhances those special moments. Thanks so much to you for expanding our “wine IQ” and making many of those ‘nice’ moments truly memorable.

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