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Nov 09, 2022
This Is How We Work Now: Olena's Story

I started a progressive career with Fortune 500 companies even before I moved to the US. I came to Boston in 1998 with $15 in my pocket and not speaking English. In 2001, I finished graduate school (Information Age Marketing, with high distinction) and started a quick climb through the corporate ladder. I never worked just 9 to 5, made sure to walk the extra mile for every deliverable, and always took projects and assignments that nobody wanted. I was trusted to manage my first team when I turned 26 (5 people, most of them older than me).

Since then, my role has typically been to start a new team, launch a new revenue stream, implement new technology, or launch a digital transformation. In other words, figure out a successful solution to a problem that nobody solved before or has a clear answer on how to solve it.

I managed 7 teams (built 5 from scratch) and was hired where a strong, insightful, and engaging leader was needed. I played the risky role of an internal entrepreneur with a passion for getting results and moving customer experience and team performance to new levels. And I did it every time.

I worked in consulting (Deloitte), internal consulting (EMC), corporate marketing (Akamai, SAP America, Nuance Communications), eCommerce (Vistaprint), and later, at several startups as an innovation and product business leader. My passion for growing businesses and for turnarounds made me switch to working for incubators and startups. One discovery I made was that they didn’t stay in business that long.

Giving birth to a challenging child took me by surprise, and I had to slow down, looking for more flexibility and acceptance (it was before corporations started paying real attention to working parents).

I was invited to do just a bit of consulting on the side when I still was working full-time. It was an interesting strategic expansion project for a global high-tech leader that I just could not say no to. That was a happy discovery; it was tough, but I loved every minute of it. I had never considered freelancing before that project. At that moment, though, my solid corporate track record and the changes in the society where contractors became ubiquitous and accepted convinced me to make a move.

My last full-time job was as a senior director at a global digital marketing agency. I resigned, unwilling to work 70-100 hours per week at an effective hourly rate of $28. I was ready to work directly with clients.

I took small jobs (on Upwork and outside) first, taking a significant cut in my earnings for the first year. Hard work, commitment to top quality, superior customer service, and perseverance of my Ukrainian blood paid off. I now have a 100% Job Success Score (JSS) on Upwork, a track record of working with hundreds of clients, and a 100% response rate to inquiries that helped me to grow on Upwork and earn the Expert-Vetted Talent badge.

Fast forward to now, three years later. I more than doubled my best earnings and gained a flexible schedule that lets me be home when my child comes home from school while still doing the job I love. Amazingly, freelancing allows me and our family to travel whenever we feel like it (I take my laptop with me). Do I work 9-5? No, I work more than that because I love what I do and do what I love.

I LOVE helping businesses launch, grow, and work through the challenges of ups and downs. 

My favorite thing about freelancing is working with business owners because they need what I offer. I don’t sell pretty PowerPoint slides or try to “retain” them by upselling. They hire an honest partner who is on their side with a strategic mind, practical knowledge of decision-making, solid technical knowledge of customer-centric multi-channel marketing, and hands-on execution experience. I am different; I always was, and always will be. I am just like them.

Freelancing lets me manage my hours and days of work, time with my child, travels, fun, and other things I need to do while making 25 years of hard work pay back. And, I have to say, the feeling of living my American Dream is priceless!