Write the Story As You Go | Wag Theory

Write the Story As You Go

by Jenny Ostoj March 24, 2019

I recently listened to a podcast with a message that resonated with me*. The primary take-away was that we don’t always have to understand how each decision or action will play out as we are experiencing it. Today, we are exactly where we need to be.

I love that concept. We all write our own stories as we go, and sometimes it can feel jumbled and disjointed from day-to-day. But often there are themes that stitch together over time that start to make sense.

After some reflection, I see how this is true with my own path.


In high school, I was driven (somewhat literally) to obtain a job as quickly after turning 16 as possible because the deal struck with my parents was that I could have a car if I could pay for the insurance. I have always loved a good plan of attack, so it wasn’t surprising that I had lined up my DMV appointment on my birthday and obtained my license that day so that I could drive myself to my first job (also starting that same week).  

The job was at a small town gift boutique, and it was there that I learned to “professionally” wrap gifts and keep the displays clean and dust free. But I also got a behind the scenes view of what it meant to run a boutique retail business. As I gained experience, I was trusted to handle inventory, make displays, and play a larger role in customer service.


In college, I focused my studies on what I thought would be most practical and useful: A major in business administration and a minor in Spanish language. My economics professor urged me to consider study abroad to tie the two together, so I spent the spring my my junior year in Spain. And it completely changed my life.


The experience of living in a different country quickly changed my outlook and priorities for a career, and I spent the next 8 years working in higher education where I could prepare students for their own life-changing study abroad experiences. That role cultivated my interest in diversity and my quest to understand different perspectives.

Seeking new challenges, I utilized my higher education tuition benefit to go back to school and was again pulled toward the most practical choice: Master of Business Administration. Working full time while being enrolled in such an intense business program taught me a lot about myself and my limits. But most of all, I learned creative problem solving skills and tactics for team building.


With my MBA in hand, I itched for another significant shift. As a lifelong learner, I was intrigued by the fast paced and every-changing world of technology. After reflecting on my ability to create and execute plans and love of working in teams, I determined that project management was the best fit.

I spent the next 8 years working with teams focused on website strategy, design and development, which afforded me the opportunity to deeply understand the intersection of marketing and technology. 

I have made lasting connections with many of my colleagues from this industry and  I “grew up” in that role. I learned how to ask questions, and think strategically. I learned the importance of customer experience, and how that should drive business decisions. I learned about technical platforms, requirements gathering, metrics, and most importantly, how to execute and deliver on plans (and how to pivot quickly when things don’t go as expected).


Solving business challenges for large corporations was interesting and required thinking outside the box, but I still craved using a different side of my brain. On the weekends, I started "making things" with my hands, and it eventually became clear that something brewed inside of me that warranted another big life change.

I started out hand stitching leather and making small gifts by hand, but quickly transitioned to machine sewing. Most of my learning in the early days was trial and error, and none of it was done in a formal classroom.

My process was:

  • Find a product I liked on Pinterest
  • Think about all of the parts that I would need construct and in what order
  • Find as many YouTube videos as possible to learn each element of the construction

I got really good at using a seam ripper (for all of the mistakes, hah!) and most of my original work didn’t turn out exactly as expected, but that early exploration taught me how to deconstruct my ideas and think of designs like building blocks.

My natural eye for detail combined with my drive for precision are the foundational elements that contribute to my commitment to high quality craftsmanship today.


Looking at each of the components of my story in isolation, you might not see how it all fits together. I know I didn't. But it all came together in the right place in the right time.

So what does it all mean?

No path is straight and unwavering. Think back on your own journey. Have you made choices that felt uncomfortable at the time, that later seemed to fit well into a greater life plan?

And always remember: Regardless of how chaotic or jumbled life may feel, today you are exactly where you are supposed to be.

*The podcast that inspired this topic was


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Jenny Ostoj
Jenny Ostoj


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