Why start with the jobs I had before my career?
When I work with clients one-on-one, one of the first things we do is walk their career timeline. We start with the very first work they did all the way back in high school: babysitting, a grocery store, a restaurant, a summer job, or volunteering.
I want to understand what they loved and hated about those experiences. In my coaching practice, those early stories often offer some of the clearest glimpses of how someone naturally shows up at work.
For many people, those jobs came before the pressure of building a professional identity. The goal might have been a need for some spending money… gas for a car or buying clothes at the mall. That was not everyone’s experience, but for those who had that breathing room, work could feel more immediate: serve the table, help the customer, and get through the busy shift. The rawest version of ourselves showed up early on, before we learned there was a corporate game that had rules to follow.
As our careers progress, we learn what gets rewarded. We learn how to look, act, and present ourselves to fit an organization. Sometimes, in trying to play that game successfully, we gradually shut down parts of ourselves. We made ourselves quieter, smaller, and a whole lot less authentic. We stopped showing up with our full selves and what we could bring and instead fit ourselves into a box everyone wanted us to be in.
Looking back can help us see those parts again. Knowing who we are and the ground we stand on gives us more space to navigate career decisions and stress without everything becoming tangled together.
What can an old job reveal about how I work?
When I was a restaurant server, I loved the puzzle of a busy service. What was the most efficient path through my tables? Which orders needed attention? When should I check in with someone? Could I tell which tables I could leave alone longer? And which tables needed me to babysit them? Did I have time for a joke? Did they have a child that was upset that I could turn this moment into a memorable experience? Did they look tired? Were they in a hurry? Was it a date night?
The interaction of people in this environment and the system of how the restaurant worked was so energizing for me. (and for those that know me well, that will ring some bells)
I enjoyed finding a flow through the chaos and creating clarity within it.
Later, I became the lead dispatcher for a local courier company. We handled same-day, on-demand deliveries. On one side were the packages already scheduled and new requests arriving throughout the day. On the other were drivers spread across the region.
My job was to make sense of it: the right packages, on the right routes, with the right drivers.
Those jobs look very different on a résumé. But the experience I enjoyed was remarkably similar. Creating clarity out of chaos has appeared repeatedly in the parts of my career where I felt most satisfied, motivated, and energized.
There was another pattern in that dispatching job, too. Efficient routes with more packages meant drivers could earn more without spending their days going back and forth unnecessarily. I worked to make that happen.
My philosophy was that if I took care of the drivers, the drivers would take care of the customers. Happier drivers were more willing to help when something unexpected came up. During my time as lead dispatcher, our branch went from one of the worst-performing branches to the top-performing branch in the company.
Reflecting on that story now, I can see a philosophy I carried into managing a global team years later: if I take care of the people, the people will take care of the business.
The title changed, sure, but that way of working stayed with me. And I think it’s the fact that I repeatedly leaned into who I am, honed my craft, and leveraged that as my unique selling point is what gave me such a successful career (even if my identity did become fused and I did burn out over time… which the point in me saying that, is this isn’t an immediate “cure” or “prevention” for burnout - that’s different).
How do I walk my own career timeline?
Start with your earliest job, including work during high school if you have that. Then move through each role toward the present. Include volunteer work if it belongs in that story.
For each job, write down:
- What did I do? A short description is enough.
- What did I love? Recall moments when you felt energized, interested, motivated, or fully involved.
- What did I hate? Recall what drained, frustrated, or upset you. Include why you left that job as well.
- What does this bring up now? Note anything you had forgotten or something that surprises you.
Look for stories you can remember. “I liked working in a restaurant” gives you less to explore than remembering how you organized your tables during a busy service. As you’re reflecting on the things that you loved or hated, as part of your reflection, ask yourself “WHY?” Why did I love this project or interaction, why did I hate the way I was treated, what was it about this situation that made me stay or leave.
You do not have to find the pattern while you are writing, just capture the experiences first. You can return to them later, on your own or with a coach, and notice what repeats. Take your time, and let each job be what it was; there is no need to force a positive memory or invent negative ones.
How can I use what I discover in my job today?
Imagine gathering the parts of your work history that made you feel most alive and putting them into one job. No job will contain only those things, but the thought experiment can help you see what you want more of.
Then look at your work today and ask yourself… “How far away is my current position from this ideal state?”
A gap does not automatically mean you need to quit, but it does give you something specific to explore. You might look for a small opportunity to solve a problem, support a colleague, or change how you approach an existing responsibility.
In my experience, these recurring sources of energy often point toward our values. They offer clues about what matters to us and the particular way we contribute. That is also part of how a career becomes a craft (a topic for a different post).
The aim is to gradually build a way of working that gives more room to the person you are. Sometimes, even just knowing this, makes all the difference in the world.
