How do you choose a career before you've really lived life?
That's the question at the center of this conversation with Alex Dworsky and Gabriel DeSanti, co-founders of Staj. Most of us are asked to decide what we want to do at 18, 20, or 22 — long before we've had enough experience to truly understand what those choices mean. And while some people land in the right place, many others find themselves years into a path that no longer fits.
Alex shares her experience inside corporate America, where careers often follow a predictable path shaped by expectations, environment, and stability. But as time goes on, many people begin to question whether what they chose actually aligns with who they are becoming. Gabriel's journey offers a different perspective — pivoting early from a technical trade into content creation, ultimately building a career around exploring what different jobs are really like from the inside.
Together, they unpack why so many people stay in roles that don't fulfill them. Fear plays a major role — fear of losing stability, identity, or success. For many, it's not just about changing jobs, but about walking away from something that looks "successful" on paper. That tension — between comfort and fulfillment — is where people often feel stuck.
A key theme throughout this episode is the lack of real exposure. Most career decisions are made with limited information, based on what we're told, what we see around us, or what seems safe. Even internships, which are supposed to offer insight, often fall short by showing only a narrow slice of the job rather than the full picture.
This conversation challenges the idea that choosing once is enough. Instead, it invites a different approach: staying curious, experimenting, and being willing to reassess what success actually means at different stages of life.
Because sometimes the real work isn't choosing the right path — it's recognizing when the one you chose no longer fits.
What's The Point? is a podcast hosted by Bill Ellis featuring real conversations with people who've figured out what matters — their purpose. Each episode explores what motivates them and how they find meaning in what they do.
Connect with Bill:
- bill@billellis.com
- www.billellis.com
- www.brandingforresults.com
- IG - @wcellis
- Facebook - @CoachBillEllis
- Facebook - @bill.ellis
- LinkedIn - linkedin.com/in/wcellis
- Book: Women Who Won
Links for This Episode:
- Name: Gabriel DeSanti
- Email: gabe@gabedesanti.com
- Name: Alex Dworsky
- Email: admin@gostaj.com
SOCIAL MEDIA INFO:
- IG: https://www.instagram.com/gabriel.desanti
- LinkedIn: https://www.linkedin.com/in/gabriel-desanti
- IG: https://www.instagram.com/go_staj
Quick Episode Summary:
- 00:00 – Why choosing a career early is so difficult
- 01:30 – The idea behind Staj (try before you commit)
- 03:00 – Alex's corporate career and COVID shift
- 06:00 – Gabriel's early pivot and "world's longest resume"
- 08:30 – Why people outgrow their careers
- 10:00 – Why most people stay in jobs that don't fit
- 12:00 – How we actually choose careers at 18–22
- 14:00 – The problem with internships
- 16:00 – Fear, identity, and career changes
- 18:30 – The "golden handcuffs" problem
- 21:00 – Why people don't explore other paths
- 24:00 – Who understands Staj immediately (and who doesn't)
- 27:00 – Why small businesses get it faster
- 30:00 – Hiring, risk, and finding the right fit
- 33:00 – Why internships don't fully solve the problem
- 36:00 – Unexpected jobs and hidden career paths
- 40:00 – How to explore without quitting everything
- 45:00 – What to do if your career feels wrong
- 50:00 – Redefining success over time
- 53:00 – Final reflections on choice and fulfillment