Hi, I’m Michael Cannon.
I write, teach, lead, automate, reflect, hike, make mistakes, recover from them, and try to live a little more deliberately than I did yesterday.
My core philosophy is simple:
Live fully by living deliberately.
That does not mean living perfectly. I gave up on that nonsense a while ago.
It means choosing with more awareness. Paying attention. Taking better care of myself. Building healthier relationships. Doing work that helps people own meaningful outcomes without burning out.
This site exists to help people understand who I am, what I care about, and what I keep learning the hard way.
A Few Things I’ve Lived Through
I have:
- Cycled around Taiwan
- Driven across Canada
- Lived in 10 countries
- Studied in 8 countries
- Traveled more than 3.2 million kilometers
- Served as a US Air Force EOD technician
- Stepped on landmines and lived to tell the story
- Earned three degrees
- Built, scaled, and supported companies
- Taught English across cultures and generations
- Photographed people and open source communities
- Overcome $380,000 in debt
- Married three times
- Divorced after 20 years
- Raised four sons
- Failed slowly, painfully, and usefully
- Geeked for more than 40 years
- Started over more than once
The details matter less than the pattern.
I keep learning that life gets better when I stop pretending, pay attention to reality, and make clearer choices.
What I Stand For
My life is guided by one purpose, three principles, and three values.
Purpose: Live fully by living deliberately
I want a life with meaning, freedom, contribution, and enough joy to make the hard parts worth carrying.
Living deliberately helps me choose what deserves my energy and what does not.
Principle 1: Take better care of myself
For years, I relied on external structure: coaches, military standards, work urgency, family responsibility, and financial pressure.
That works until it does not.
Now I’m learning to care for myself without needing a crisis as motivation. That includes meditation, movement, sleep, food choices, lower debt, and enough rest to remain useful.
Not perfect. Useful.
Principle 2: Have healthy relationships
Healthy relationships require attention, courage, gratitude, feedback, and listening.
I try to spend time with people I care about, people who inspire me, and people with whom there is mutual respect.
I have also learned that some relationships need to end. That lesson came late and cost plenty. Still, clarity is kinder than pretending.
Principle 3: Be an inspiring person
I want to challenge the status quo without becoming arrogant about it.
That means checking my ego and greed, sharing what I learn, setting clearer boundaries, and helping people take ownership of what they do.
My best work usually happens with people who care enough to think, speak clearly, and follow through.
How I Try To Show Up
Smile
A smile is not avoidance. It is a small signal of welcome, humor, and openness.
It reminds me to change myself before judging someone else.
Respect
Respect means calm presence, compassion, and curiosity about impact.
It also means directness. I would rather be kind than merely nice.
Purpose
Purpose helps me choose consciously.
Sometimes that means acting. Sometimes it means waiting. Sometimes it means walking away.
The Work Behind The Words
Much of what I write comes from leadership, automation, teaching, recovery, fatherhood, travel, and failure.
I care about:
- Sustainable ownership
- Healthy accountability
- Remote leadership
- Automation that helps people rather than replaces judgment
- Clear communication
- Practical self-care
- Resilience without heroic burnout
- Better conversations
- Living well without needing excess
My recurring question is:
How do we build lives, teams, and systems that help people do meaningful work and still live well?
That question keeps showing up in my writing, teaching, consulting, and personal reflections.
My Best Starting Points
If you want to understand how I think, start here:
- 7 Ways to a Thriving Open Source Organization Culture
On accountability, passion, shared responsibility, and community. - Being a Digital Nomad
On travel, work, curiosity, and choosing experiences over convention. - Fostering Fairness: The Role of Automation in Appraisal Systems
On using automation to support fairer, clearer people systems. - Leveraging Digital Exhaust for Accountability & Meaningful Conversations
On turning workplace signals into better conversations. - Hopeful Expectations
On uncertainty, leadership, and responsibility during difficult times. - When Uncertain, Decide Beyond the Horizon
On long-view decision-making when the present feels messy. - The Art of Productive Laziness: Leveraging Automation for Meaningful Work
On using automation to reduce friction and preserve energy for better work. - Automating Project Planning With Integrated Team Member Costing Information
On connecting planning, cost awareness, and operational clarity. - The Evolution of My Development Process
On how my thinking shifted from discipline toward better environments. - Discipline Down, Environment Up
On why the environment often beats willpower.
What I’m Still Learning
I’m still learning how to pace myself.
- How to choose fewer things.
- How to recover without guilt.
- How to be direct without becoming harsh.
- How to stay ambitious without letting ego or fear drive the bus.
- How to build financial security without sacrificing the life I’m trying to live.
- How to be present with my family, students, colleagues, and friends while still doing work that matters.
Some days go better than others.
That is part of the point here.
Deliberate Life Goals
I want to:
- Be reflective
- Be with whom I choose
- Do my best
- Enjoy what I do
- Feel free to choose
- Learn from failure
- Retire comfortably
Thanks for taking the time to get to know me.
If something here resonates, you’re welcome to keep reading, reach out, or simply take what is useful and carry it forward.
