Your Life in Perspective: The Timeline Exercise
- Chris Coraggio
- Mar 24
- 3 min read

You know those movies or TV episodes where you see what happens in the end, and then you go back in time to see how that moment came about? (White Lotus Season 3...)
Perhaps we can take a page from that narrative arc. I highly recommend we all do what's called a "Timeline" exercise. I'll share more about what that is, but I'll share my story first:
2 years ago, I remember having a moment of wanting to give up my business. Nothing was working, I had no clients, I was saying to myself: "what am I doing here? I'm going nowhere. This is a waste of time, it's no use trying." Thankfully, I built up a reflexive habit of journaling when my brain gets crazy and researched what to do in moments like these where I feel a bit lost, stuck and hopeless - in the morass.
One of the pieces of advice I read was to engage in a bit of a timeline and “story of self” exercise. This exercise helped me make sense of different periods of my life, transitions, and dig into why my highs were highs and my lows were lows. I saw myself at 10,000 meters up: my essence and my story.
I discovered a few key points about myself:
I love helping people reach their potential (teacher/education/HR...)
I love creating, building, and innovating things
I love creating community and leading teams
I am relentless and don’t give up if I want something
Together, the above reflections reinforced by decision to keep training as a coach, and to try building a business imbued with my own flavor, my brand, my mission. And, if this turns out to be what I really want, then I'll relentlessly work at it - and be unstoppable. This reflection helped me recommit to my journey with rock-solid commitment and confidence, as if my success was already cemented in stone.
The other major realization of this whole exercise was that I am at the most difficult point in this

career change (and starting a business). The part right after opening the business is the hardest - like after you have the "Grand Opening!" and customers stop coming because the novelty wore off.
Having zoomed out and now seeing this as a 30+ year career arc, helped me put this current moment in perspective. It didn't make this moment easier, it just gave me comfort that it won't always be this way and that it can only get better.
And even another major realization - in my hardest times, even when I made the "wrong" decision to work in HR for Citibank, those moments were still pivotal in my life. Those moments taught me what I was really capable of, and that I don't tolerate anything except what is worthy of my time and talent. So even wrong turns, failures, and bumps in the road are important parts of this journey.
How the Timeline exercise works
Let me start by saying that we offer this as a service in our regular coaching, or if you join the YOLO.LFG Program. You complete the directions through a worksheet and then we synthesize some of the most important takeaways for you as you look forward to what's next in your life.
The Timeline generally consists of 5 major sections:
Identify the major phases of your life in a straight line
Use a curvy line to chart the high and low points in your life, paying attention to relative highs and lows
Write notes about important moments and transitions
Reflect on where you've been and where you are now, noticing patterns, growth, and signs of what makes you, you and your story unique
Synthesize and learn to tell your story to others succinctly - is it a story of perseverance? adventure? community? impact?
Here are 2 examples of how to structure the timeline (and linking to their websites for more guidance):
From Pathfinder.com:

From OliveMe Consulting:

It is less important that you follow the structure, and more important that you have a few questions in mind for yourself.
Summary
Remind yourself to put things in perspective. You'll alleviate the deep negative feelings of the moment with a dose of peace, calm, gratitude, etc. The big patterns seen from 10,000 meters above are what will be the patterns that will guide you your entire life. This is your essence and your story - your enduring context by which you live your life. Know this, and you'll design and live a life that truly fulfills you.
If this resonates, let's connect - book a discovery call or shoot me a LinkedIn message.
For Learning and with Love,
Chris



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