Is Contentment Measurable?

Or does the act of attempting to measure it mean you are in fact, not content?

In part one, I reflected on a year that felt a bit meh, despite all the evidence otherwise. On how “more” wasn’t simply the answer, even if I expected it to be.  I was able to hit a bunch of milestones but still felt a bit flat.

For 2023 I’m hoping to spend more time reflecting on perspective, rather than solely on achievements. 

Not to say goals and achievements will not be central to me. It’s who I am, and who I intend to be. Having a life filled with great people and adventures doesn’t happen by accident. (unless you live in New Zealand or something?)

Documenting goals gives me accountability to myself, which makes me more accountable to others. I understand the irony of writing a self-imposed annual review and claiming otherwise.

But, I’m not sure you can measure contentment.

Or the ability to find stillness.

Or gratitude.

Or fun.

But hey……. here’s trying:


  • Create a Digital Hub – We use a system called Traction for LooseGrip, tied to a Trello board which basically breaks big goals into small goals. Why not try out creating one for life. Deadline 1/15
  • Walk w/o Stimuli – I walk a lot. With the dog. To kids, school. Etc. But I almost always have headphones in so I can be “productive” – One 30 minute walk a day without devices.  
  • Read 25 Books  –  Deadline 12/31
  • No Boredom/Default Drinking –  A lingering pandemic habit has clearly been a switch from a decision to drink — whereas now the decision is to not drink — or that a drink or two has become the default rather than the exception. Track Every drop of booze I consume in 2023 (I’m using the app “Less”)
  • 12 Micro Adventures – I tend to spend hours wistfully researching giant ass adventures. But as Beau Miles preaches, a whole lot of adventure can be had in your backyard.  Goal: 1 Monthly Micro Adventure, w/photo post proof. 

BIZ – 

  • Show and Tells – We started doing shop talks with other agencies last year. A closed door show and tell about how we do a specific aspect of our business in exchange for 30 minutes about theirs. Deadline:  1 per quarter
  • 3 x Conferences with A-players – This last year I spoke at two conferences with very different groups but each made me step my game up. I’d like to add one event that is even less directly tied to LooseGrip with a focus on depth on connections
  • Automate my Personal Retirement Investing – Entrepreneurs generally suck at this. I fit the bill. Deadline 1/31 
  • Continued Do-Goodery – We Joined 1% for the Planet this year, and I’d love for us to be more active in the community (along with our donations) in a way that donates our brains and not just our wallet.


  • Two Kid-Free trips – See below for the first, but I’m hoping to get one more short one in as well. Deadline: 9/1
  • One Anti-Trip – Traveling with me is not very relaxing. We gotta see, eat, and do it all. Laura and I scheduled an all inclusive, boring beach vacation that is the opposite of any trip we’ve taken otherwise. Deadline 2/15
  • Three Weeks at the Lake – I’ve got a pretty decent lake office set up, so no real reason this can’t be achieved. Deadline 10/1
  • Two Multi-Day Adventures – A race, a bike-packing trip, paddle-boarding trip, whatever.
  • Face time with Every LG Client and Team member – I.R.L. – Deadline 11/1


  • Five minute mile Deadline 5/5
  • 10 Ring Muscle Ups – I made it to 8 twice this year. Deadline 3/31
  • 3 Races Deadline – register or complete by 6/1
  • Snow Ski 10x Days – Deadline 4/1
  • Adventure-Kid Goals – Lida – Downhill ski. Shea – Big-kid-bike. Deadline – 7/1

About my annual review: For the last 10 or so years, I’ve tried to look back at the year before and see how it stacks up, while also setting goals for the year to come. I find the exercise invaluable as a mechanism to be inspired to do more cool stuff. The categories Life, Fitness, Business & Travel work best for me, but if you’d like to do your own I recommend checking out my buddy Chris’ Template to get started.

NeilCallanan Truths

Leave a Reply

Your email address will not be published.