My Spiral Career: From Theater Major to Financial Services to Leadership Coach

September 17, 2026
A headshot of Tali Graham

“Who do you want to be when you grow up?”

It feels like every decade, I’m asking myself that question again. A Theater major who rebelled by working in Finance in New York, to a Leadership Coach & Facilitator - this was not a path I even knew existed when I was in college! When I graduated I had my sights firmly set on Broadway, or maybe I’d settle for film and television. Graduating into the 2008 financial crisis offered some robust reality checks, particularly regarding the cost of rent in New York City, and I realized I wanted to experiment with stability. Next thing you know I’m working as an admin for a hedge fund, and realizing this “corporate thing” wasn’t nearly as hard as I’d have thought. After a couple years I moved on to S&P Global, working with Structured Finance analysts before getting promoted to a people management role in the Financial Services business unit. A couple promotions, work travel, and one Green belt in Lean Management later, I started taking vacation days to get back into acting.

It worked for a while. Did you know you can be good at something, and still be unhappy? I learned that the hard way. After years of planning and saving I left in August 2019, and was ready to pivot into my full time portfolio career as an actor, model, training facilitator & coach…and 6 months later I was hunkering down at my now-husband’s family home in Massachusetts, no longer a resident of the city I’d pledged to never leave.

I now live in the woods outside Stamford, CT, with a successful career as a leadership & career coach and training facilitator. As I near 40, it’s hard not to look back at where I started and marvel at how many plans went sideways, yet still brought me to a place I’m quite happy with. On reflection, an 18 year old who decides to get a BA in Theater was probably never going to follow a typical path, yet I think I still had some notion that it would be more direct than it ultimately was.

Perhaps it’s time to expand how we think about career progression.Harvard’s Professor Arthur C. Brooks describes 4 distinct types of careers:
 

  • Linear: traditional, steady progressions of promotions and a clear ladder. (This is the one most education is preparing us for.)
  • Expert: pursuing deep mastery as the goal, rather than titles or climbing. 
  • Transitory: moving across industries or roles every 1-3 years, learning constantly, reinventing themselves and driven by location, curiosity, and lifestyle. 
  • Spiral: multi-year evolving mini-careers every 7-12 years, revisiting past interests/roles at a different stage of life, with new skills, perspectives, and purpose.


Looking at my own “spiral career” I’ve started to see how my seemingly random career pivots have actually been an evolution of prior paths.

Actor/Model: where I started, gaining over a decade of professional experience in film, theater, opera, voiceover, commercials, improv, and fit modeling. I learned the criticality of collaboration in a team dynamic, emotional intelligence, and even some psychology.
Finance & Financial Services: from an admin, to associate, to people manager, where I discovered a love of excel, operational processes, earned my Green Belt in Lean Management, and experienced firsthand the importance of people leadership. This is where I began creating and leading trainings, and started coaching others.
Training Facilitator & Coach: how I’ve combined my unique skill-set, blending public speaking and performance with leadership experience, leadership & coaching certifications, and an ongoing love of learning to share with others.

In Spring 2008 I had no way of knowing where my BA in Theater would take me. I’m happy to say that while the path has been entirely unexpected, I have found a career fulfillment I didn’t think was possible. I truly believe the same can be true for you.

So, what do you do with this? Try today’s 5-minute Habit Snack:

Write down every role you’ve ever had.*

Next to each, write all the skills and/or perspectives you gained that you benefit from today. 
Use this reflection to identify your career type, inform a decision on your trajectory, or as preparation for a coaching or mentoring conversation.

*If you’re a student, include your extra-curriculars, part-time jobs, and any class where you’ve applied skills or knowledge outside the learning context. If you’re on your way, include every role you’ve had, even ones that felt like detours.

While looking back I see a clear path, at the time these transitions were genuinely hard. The thing that helped me most was the question, “How do I define success?” For me, it became about a life lived in alignment with my values, and a certain lifestyle of travel, art, and time freedom. Strip away the titles and external accolades; the answer to that question can help guide your decisions, for life and a career wholly on your own terms.