Top 40 Lessons from 2025
- Jack Fleming
- Jan 1
- 6 min read
A great source of reflection, definitely my favourite blog post to write every year and enjoy looking back on past ones. The year of fatherhood, returning home, U19 World Cup, new job and major life adjustments! Enjoy!! Here are links to some past reads too.
LIFE
Moving home - from Hobart, Tasmania back to Melbourne brought on a rich mix of emotions. The joy of being so close to friends and family, the adjustments of life in a myriad of ways and the recalibration into what once was familiar.
Just because somebody carries a weight 'well' doesn't mean it's not heavy.
Who do you need to ask - what's the real challenge for you?
Your journal only reveals it's value in reverse.
Your deep honestly while nobody is watching, provides clarity and confidence for the future. There's a book to be written in there somewhere, one day.
Life doesn't provide new problems - it reuses old ones until you change.
Some lessons can only be learned by bleeding on them yourself.
A great post written by Chris Williamson on the Unteachable Lessons.
Find what feels like play to you, but looks like work to others. When it stops becoming play, it's time to move on.
Life feels whole when four buckets are alive: craft, community, contemplation, and constitution.
Decisions only you can make for yourself:
- Who you love
- What’s worth your time
- Where you call home
- What “enough” means
- When to walk away
A busy calendar is a hedge against existential loneliness.
Spending a tremendous amount of solo time on the big questions, has provided me with a lot of clarity.
Inside of every complaint is a request.
At the heart of your relationship can you skip the complaint and get to the underlying desire or need? This was a great podcast to listen to about masculinity and relationships.
Be proud of the things you say no to.
When you know what your priorities are, saying no can become easier.
If you fix your hardware (sleep, exercise, sunlight, food) it can help your software almost fix itself.
New job, new baby, new schedule made me forget this lesson too many times.
If you must play, decided on 3 things upfront. Rules of the game, the stakes and the quitting time.
Never be afraid to become a beginner again.
The tool that got me here, is not the one that will get me there.
Going on a massive journey to end up where you started, is not as the same as never leaving.
“No man ever steps in the same river twice, for it’s not the same river and he’s not the same man.”
We are deeply mimetic creatures. Most “shoulds” are traps laid by society — or by outdated rules you never revisited.
Have the courage to face your own flames. Not until a man has stopped running, can he grapple with the pain that has driven his own behaviour.
The most terrifying place is the truth of who we are, but can be the most empowering.
The most courageous act of the shielded man is the surrender of his armour.
At different times this year life hit me with overwhelm, and the most difficult thing was to ask for help.
Often we trade hidden metrics for observable metrics, because people can only judge your success from the outside.
Did you trade more money for less time, a fancier car for less practicality, or a bigger title for less of the job you actually want to do? Only you can judge the most important metrics and what they mean.
FATHERHOOD
On September 6th 2025 - we welcomed into the world Nash Fleming.
Your child can see into your soul, can feel exactly what is inside you.
It has made me cry and smile so many separate times, there is no hiding from them. How beautiful - their eyes are a mirror of truth.
Do Not Ask Your Children to Strive by William Martin
Do not ask your children
to strive for extraordinary lives
Such striving may seem admirable,
but is the way of foolishness.
Help them instead to find the wonder
and the marvel of an ordinary life.
Show them the joy of tasting,
tomatoes, apples and pears.
Show them how to cry
when pets and people die.
Show them the infinite pleasure.
in the touch of a hand.
And make the ordinary come alive for them.
The extraordinary will take care of itself.
We are all flawed children, just doing the best we can.
Parenting will humble you over and over, so grace is the skill you practice most.
Children are cared for in ecosystems, not households. If you let people in.
One of the blessings of being home, seeing the joy it brings friends and family to be around Nash - and being able to make a call when help is needed.
A child's face of joy and wonder, reminds you how beautiful it is to be human.
Reminder to never lose your childlike curiosity and wonder.
U19 WORLD CUP
A blog post around the mix of emotions after winning a silver medal.
Good coaching is setting the conditions to allow people to fail, and go forward.
Renae Garlepp is a tremendous coach and excited to see the future.
Follow Your Genuine Curiosity
Would I have ever thought I would be an assistant coach at an U19 Womens World Cup? Sometimes the most meaningful opportunities arrive sideways, what a rewarding experience and such a privilege to coach these young women.
Big games require 3 things:
- Fundamentals
- Togetherness
- Resolve
RECOMMENDATIONS
5 Favourite Books of the Year
- The Creative Habit by Twyla Tharp: Legendary dancer and choreographer on her practical habits for creativity.
- The Art of Winning by Bill Belichick: All things coaching, simplicity but a clear philosophy.
- Bittersweet by Susan Cain: How sorrow and longing makes us whole.
- Good Inside by Becky Kennedy: Tremendous read on parenting.
- I Don't Want to Talk About it by Terry Real: Excellent education on male depression, healthy masculinity and confronting trauma.
5 Favourite Podcasts of the Year
- Matthew McConaughey on the Art of Living a Courageous Life
- Boyd Varty: The Return of the Lion Tracker on Tim Ferriss
5 Favourite Quotes
"True inner self must be drawn up like a jewel from the bottom of the sea, rescued from confusion, from indistinction, from immersion in the common, the nondescript, the trivial, the sordid, the evanescent.” - Thomas Merton
“Greatness takes guts. And often, it's the courage to eliminate the things you can do fairly well so you have the capacity to do one thing exceptionally well. Have the courage to take more off your plate." - James Clear
"The answers you are looking for are in the silence you're avoiding." - Chris Williamson
“You think your pain and your heartbreak are unprecedented in the history of the world, but then you read. It was books that taught me that the things that tormented me most were the very things that connected me with all the people who were alive, or who had ever been alive.” ― James Baldwin
“And now that you don’t have to be perfect, you can be good.” — John Steinbeck, East of Eden
Turn your favourite quotes into graphics or images on ChatGPT - bring them to life!
QUESTIONS
A lot of these have been stolen from Chris Williamson on Modern Wisdom!
What did I develop in my 20's - that no longer serves me as much now?
Productivity as an identity.
What are the thoughts you repeated too many times this year?
Slow down.
What would 80 year me, have appreciated about my day today?
Slow walks.
What would it look like if it were easy?
Let go of control.
If your life was a movie, what would the audience watching be screaming at the tv?
Show yourself some compassion, some grace.
If I stopped trying to arrive, how would I live today?
With more surrender.
What do you want your son to remember about his first 4 months with his parents?
They were present, through all the amazing unstructured and quiet moments.
What is wishing to be expressed in the world through me?
Sharing your story to create positive ripples in the world, and giving permission for others to feel all the emotions of being a flawed but beautiful human.
FINAL THOUGHTS
Dear Love, what would you have me know today?
Change does not ask you to be ready — only willing.
Surrender is not the end of effort, but the softening of resistance.
And in that softening, tranquility finds its way in — not as a reward, but as a companion.
Trust the quiet shifts, the small openings, the unseen currents moving beneath the surface.
Let them carry you.
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