The Cold, Hard Truth

I started Viaggio Partners with the goal of helping moms find flexibility in their work without sacrificing the equity they had already built in their careers before starting families. Little did I know that this would morph into working with millennials looking for the digital nomad lifestyle, and baby boomers interested in semi-retirement and snowbirding during the winter. I am so grateful and excited for the journey that lies ahead.

“If you are lucky enough to find a way of life you love, you have to find the courage to live it.” – John Irving

I never felt that I fit in a corporate environment. I got my bachelor’s degree in accounting and really enjoyed the work, but culturally it just wasn’t the optimal fit for me. I convinced myself that it was okay, because I loved the people I worked with and it was when I went to school for, so I what other options did I really have? I felt starved of my freedom in a number of ways for many years, but thought I didn’t have a choice.

The long hours of busy season often drained me, but this was the lifestyle I signed up for when I decided on my line of work. I often came out of the fog of the 4/15 deadline saying, “where did the first three months of this year go?” I remember one of my first managers once joked about how a job in public accounting was “a great way to burn through the winter.” I used to find some comfort in that living in Boston, because it really did help make those cold, gray winter weeks fly by… And then there was the stuffiness of business dress and business casual attire (insert eyeroll here). Don’t even get me started. What I realized after 10 busy seasons, though, was that I was missing out on quality time with family and friends – and I didn’t even have kids yet. I could never understand how my female managers did it while raising their own families.

I was raised in a household where my mom was always home. She ran her own business – a children’s daycare – out of our house. Growing up in this environment and seeing parents leave their children 40 hours/week with someone else was one of the reasons I chose accounting as a major in college. Since, per Ben Franklin, my career would focus on one of the two constants in life, I knew there would always be a demand for my services. And seeing my mom run her own business from home, I knew it could be done.

What I didn’t see coming was the speed at which technology progressed over my high school and college years, which allowed me to be connected remotely to my future employers’ offices while I was at client sites, and very occasionally from home. And as technological advances surged, the world became smaller.

My employers – all three of them between 2007 and 2015 – started outsourcing to India. Information was shared securely via the internet. If we were sharing with India, why did we need an office at all? When my employers were willing to outsource to another country, but resisted allowing local staff to work remotely, I questioned why (as I have always done throughout my life with anything that didn’t make sense to me – just ask my parents).

The biggest reason was because they felt employees would take advantage of the arrangement and not actually get work done. We were also dealing with a major generation gap. The baby boomers expected their employees to report to work daily – seeing them at their desks made it more believable that they were actually getting their work done. It’s also what they did to work their way through the ranks over their careers, so why should the younger generations expect more favorable treatment?

But once millennials (the generation most inclined to question the way things are done – and yes, I’m proud to be one of them) who grew up with technology reached the workforce, they were ready to embrace and experiment with the technology available.

When I did start working from home at the end of my career in public accounting, I realized first-hand how much more productive I was because I was working in an environment in which I was much more comfortable – in my yoga pants, no makeup, AND saving time on a commute. It was the most satisfied I had ever been with my work life.

So here’s the cold, hard truth. Dressing up for work everyday and commuting to an office doesn’t make me any more professional or talented than if I do the same type of work wearing my workout clothes. My messy bun and tattoos don’t indicate lack of professionalism or dedication to my clients. I’m pretty sure they actually appreciate my self-expression and authenticity, which combined allow my creativity and positive attitude to flow freely.

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