The blog · September 25, 2026
The Journey Was The Point- Exercise
The Journey was the Point
We spend so much of our lives focused on getting somewhere.
The next goal. The promotion. The relationship. The business milestone. The answer. The version of ourselves we think we’re supposed to become.
But when you listen to people reflect on their lives after they’ve achieved the thing they were chasing, you often hear some version of:
“I wish I had enjoyed the journey more.”
Looking back, they realize that the messy middle wasn’t simply something to get through. It was their life.
This exercise is an opportunity to step outside of your current perspective and look back at earlier versions of yourself with the wisdom you have now.
Not so you can judge the decisions you made or imagine how you could have created a perfect outcome.
Instead, ask yourself:
If I knew then what I know now about myself, how might I have experienced that season differently?
The Exercise
Choose one or two points in your life to revisit.
For example:
5 years ago
10 years ago
15 years ago
20 years ago
If those timeframes don’t fit your life, choose a few meaningful chapters instead.
Before you begin writing, go back through the photos on your phone.
Scroll back as far as you can. Look at old photos, screenshots, trips, homes, workplaces, friendships, relationships, celebrations, and ordinary moments.
Use them to transport yourself back.
Try to remember:
Where were you living?
Who were you spending your time with?
What did your normal days look like?
What were you trying to accomplish?
What were you worried about?
What did you desperately want to happen?
What felt uncertain?
What did you think you needed in order to finally feel successful, secure, happy, or enough?
Try to remember the version of you who existed before you knew how the story would unfold.
Then journal through the following prompts for each chapter.
Reflection Prompts
1. Who was I during this season of my life?
What mattered to me? What was I focused on? What was consuming most of my attention?
2. What was I trying to make happen?
What goal, milestone, answer, relationship, achievement, or outcome was I chasing?
3. What was I afraid of?
What did I worry might happen if things didn't work out the way I wanted?
4. What emotions was I carrying regularly?
Stress? Excitement? Pressure? Anger? Insecurity? Hope? Comparison? Urgency?
5. What was actually good about my life at the time that I may not have fully appreciated?
Think about the people, freedom, opportunities, experiences, health, ordinary routines, or small moments you may now see differently.
6. Where was I creating unnecessary suffering for myself?
Were you overthinking? Rushing? Comparing? Trying to control the outcome? Needing reassurance? Putting enormous pressure on yourself?
7. Without changing any of the facts or knowing anything about the future, what would I tell that version of myself?
You cannot warn yourself about something you couldn't have known or tell yourself which investment to make.
You only get the wisdom you have gained about how to live.
What would you tell yourself about trust, patience, relationships, ambition, fear, self-worth, or enjoying your life?
8. What would I still do exactly the same?
Sometimes hindsight doesn't show us that we chose the wrong path. It shows us that we could have walked the same path with less fear.
9. What would I do with less of?
Less urgency? Less anger? Less pressure? Less comparison? Less trying to prove yourself? Less internal turmoil?
10. What would I do with more of?
More presence? More trust? More fun? More courage? More rest? More gratitude? More confidence in yourself?
Now Bring It Forward
Once you've reflected on your past, turn your attention to your life today.
Imagine yourself five years from now looking back at this exact season.
You already know there are things happening today that your future self will someday feel nostalgic for.
So ask yourself:
What am I rushing through right now that I may someday wish I had enjoyed?
What am I making heavier than it needs to be?
Where am I waiting for an outcome before allowing myself to feel happy?
What would my future self tell me to stop worrying so much about?
What people, experiences, routines, or moments in my life deserve more of my attention right now?
If I knew this chapter was part of the “good old days,” how would I experience it differently?
And finally:
What would it look like to pursue everything I want while suffering less along the way?
You don't have to stop wanting more.
You don't have to stop being ambitious.
You don't have to stop moving forward.
**The invitation is simply to remember that your life isn't waiting for you at the finish line.
You're already in it.**