Some careers are shaped by a single company, a clear ladder, or one long-term specialization. Others evolve through different industries, changing roles, and the realization that one path doesn’t always fit forever.
Lesley Higgins’ story reflects that kind of evolution.
Her professional life has moved across politics, consulting, Salesforce ecosystems, creative work, and independent contracting — not through rigid planning, but through adaptability and a willingness to step into whatever needed to be solved next. Along the way, she also discovered something many professionals eventually confront: the size and structure of a company can deeply shape how you work, grow, and see your future.
For some people, large organizations provide stability and direction. For others, they create the clarity that independence might be the better fit.
What makes Lesley’s journey compelling is the way she allowed herself to follow that realization instead of forcing herself into a business path that no longer aligned. What began as freelancing is now becoming something far more intentional — a business with multiple branches and a long-term vision.
There’s a refreshing honesty in the way she describes this stage of growth: not as a polished “success story,” but as the process of building something sustainable and fully her own.
I was in charge of compliance for a political campaign in New York City and between elections it was just me and a fundraiser. One of us had to handle emails for the campaign, and it certainly was not going to be the fundraiser. That was where it started.
Eventually, one of my college teammates (I ran XC and track at the University of Colorado) asked me to fill a gap in his Salesforce practice completing a migration to Pardot. I worked for his company for several years until we were acquired. Eventually, I decided a large corporation was not for me, and I went off on my own.
I actually started freelancing in politics while living in NYC well over a decade ago, and juggled several small campaigns along with a couple of bigger ones. For a few years, I also worked as a contractor conducting background checks for the federal government.
I have always been very non-traditional in my approach to employment, and have been a contractor more than I have been a full time employee. However, just over the last year I have started looking at freelancing as a business and am working to build it out like a grown up.
If my business were a person, it would finally be growing out of its teenage years and thinking about how it's going to develop into a self-sustaining adult.
The most recent milestone I hit was filing to be an S-Corp and all the official business requirements that come with that. My next milestone will be successfully registering as a Salesforce Partner.
Additionally, I have two other business lines that I am working on building out - a graphic design arm for youth sports (team logos, merch, etc), and a voice acting and music production arm to support my kid's dreams of being a professional musician.
Salesforce's Data 360 and its integration with Marketing Cloud Engagement is not well documented. I think there are a lot of opportunities to expand in both building and documenting that line of business.
I would have left my last full time job and ventured out on my own a year earlier than I did.
What stayed with me most from Lesley’s story is the idea that careers do not have to follow one perfectly defined direction.
While building her Salesforce and email business, she’s also creating space for entirely different creative ventures alongside it. There’s something refreshing in that approach — the understanding that professional growth, personal interests, and family dreams do not always need to exist separately.
Sometimes the strongest businesses are the ones built around the full reality of who we are.
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Add Your Voice!
This interview is part of The Email Freelancer Pathways Project, a series documenting the many different paths into email.
Through a short survey, I’m collecting experiences from email professionals to make these career journeys visible — and to help advocate for better access to the tools people are expected to master.
If you work in email in any capacity, your experience matters.
📩 Connect with me on LinkedIn or send a message.
With Love from Lanzarote, Canary Islands
Annett
Founder, EmailBoutique.io
