The Power of Pivots: How I Built a Career Through Curiosity
Less "Career" and more professional way of life
It became clear to me some time ago that my career path was less like a ladder and more like a jungle gym — full of pivots, experiments, and detours. It took time (and some soul-searching) to make peace with those shifts and to see the red thread running through it all.
Honestly, I’d much rather be on a jungle gym than a ladder.
For me, that through line has looked like:
Following my curiosity – I don’t know what’s out there until I find it.
Expressing my creativity – I’ve always gravitated toward small teams and early-stage environments where there’s room to innovate.
Skill Building – I often say I spent my 20s in a self-designed “personal rotational program,” gaining skills I didn’t yet know I’d need. From excel to designing decks.
So what did that actually look like?
Summer Internships:
Psychotherapy Center – After freshman year, I helped run an art and literacy camp for low-income children. I was a fine arts major at the time.
Theme: Art + Children + Impact
Lawyers for Children – Shadowed social workers and attorneys advocating for foster youth. I had switched to a government major with a law and society minor.
Theme: Legal Advocacy + Child Welfare
Lloyds Banking Group – Interned in Risk & Compliance during the London Olympics. Rode an elevator with Bill Clinton (!). Theme: Legal → Financial Services
Early Career:
Hedge Fund – Started in operations transformation. I thought I’d keep creativity on the side and maybe prep for law school. Theme: Finance Services → Asset management + Ops + Realization that I needed more dynamism
(Creative outlet: joined a theatre nonprofit board, ran an adoption awareness fundraiser, joined Lawyers for Children’s leadership council)
FinTech Incubator – Helped build a digital capital introduction platform inside an established company. Started the client relations team, established ops and supported marketing. Again, London-based HQ.
Theme: Financial Services → Startup Functions → Marketing
(Creative outlet: launched a comedic video campaign with my best friend on the realities of women at work — one of my most fun and fulfilling side projects.)
Global Brand & Innovation Firm – Worked with legacy consumer brands to reimagine existing and future products through consumer research and creative strategy.
Theme: Pivot to Marketing & Brand + Creative Expression Solidifies
Business School Break:
People often say, “You can switch function or industry — but rarely both.” I realized in hindsight that my pivots followed that rhythm: always pulling a lever between function and industry.
Post-MBA Roles:
Big Tech (Entertainment Division) – Piloted a new client insights role focused on how to reach emerging audiences. Returned in sales & marketing for major sports brands
Theme: Brand + Consumer Insights in a Tech Context
Nonprofit (Tech & VC Ecosystem) – Joined a small org focused on founder and operator mentorship in startups. Focused on structured partnerships with VC/PE firms and marketing.
Theme: Tech Ecosystem → Nonprofit Leadership → Purpose
Today:
I work at the intersection of healthcare, career coaching, and art - you might see some comedy sprinkled in. It’s the fullest expression of what I’ve been circling toward all along: creativity, impact, and autonomy. I finally feel like I can bring my full self and full skill set to the table. Every day is different, and I’m still growing — but instead of jumping to the next thing, I’m going deeper where I am.
Each stop along the way taught me not just what I want to do, but how I want to live. It takes an immense understanding of people and companies so you can clearly communicate your value and transferable skills.
If you’re jumping around — keep going. Sometimes, the “path” only becomes visible in hindsight.
If you’re not convinced - here’s the difference between a jungle gym and a career ladder.
Career Ladder:
Linear Progression – Follows a straight, upward path with clearly defined steps (e.g., junior → manager → director).
Title & Status-Focused – Advancement is often tied to hierarchy, titles, and external markers of success.
Narrow Path – Limited flexibility; success is often measured by how high you climb within a single domain or industry.
Career Jungle Gym:
Nonlinear Movement – Embraces sideways, diagonal, and exploratory moves (e.g., switching roles, industries, or starting projects).
Curiosity & Fit-Focused – Success is more personal and defined by learning, passion, purpose, and alignment.
Flexible Growth – Allows for experimentation, reinvention, and adapting to evolving interests or life changes.
Are you on a ladder or jungle gym? Are you fulfilled where you are?
With love,
Sasha Mack