Taking Back Christmas: An Entrepreneur’s Journey

An entrepreneur’s journey to reclaim the holidays (and self)

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December 25, 2015. The house smelled of fresh pine. There was a slight ‘chill’ in the air, according to SoCal weather standards. And I felt the nostalgia that I have felt every Christmas for the last 20+ years since I discovered Santa didn’t exist.

My family celebrates Christmas, and I was raised with all the religious beliefs about the holiday and with the understanding that Christmas should be about spending quality time with family and friends. Christmas should be about love, gratitude, and celebration. Throw in some turkey, a glazed ham, and a few simple gifts, and that was Christmas. And it was perfect.

Christmas shouldn’t be spent working on your laptop.

Shouldn’t involve checking your mobile phone. Shouldn’t include stressing about your work deadlines. But that was my Christmas 2015.

I remember vividly almost one year ago the look on my parents’ face when they arrived at my house that Christmas Day to pick up my husband and me to carpool to his family’s home for dinner. My family likes to dress up for the holidays, so when they discovered that I was dressed down — in my pajamas, to be clear — they were less than thrilled.

I explained to them that I was working on some important client deliverables. I’m a management consultant for a global firm, and I work with Fortune 500 clients. Management consultants typically work 60-80 hours per week. The job’s not for the faint of heart. But what you sacrifice in sleep, you make up for in the amount of and speed at which you gain business knowledge and experience by solving some of the toughest strategic problems for the world’s leading companies.

As I was explaining to my parents why I needed to work on Christmas, I started to have an out-of-body experience — listening to and judging the words that were coming out of my mouth. I wasn’t buying my own argument, and I was beginning to get frustrated with myself.

It was Christmas… What was I doing?

I told my parents and husband that I would meet up them as soon as I wrapped up my work and got dressed. As I watched them leave with disappointed expressions, close the front door, and back out of the driveway, I felt more alone than ever. I had always been surrounded by a ton of family and friends on Christmas. It was never a quiet holiday. It was festive and loud and filled with laughter and holiday music.

The quiet hurt. Despite my typical stoic, stiff-upper-lip, no-nonsense attitude, I crumbled into a mess of tears as I sat at the kitchen table, entered the password on my laptop, and resumed my work.

In that moment of isolation, sorrow, and self-pity, I made a promise to myself: I would never work on Christmas and disappoint my family like that. Never. Ever. Again.

As a woman who likes to take action right away (read: yesterday) and becomes unstoppable (read: obsessively persistent) when she puts her mind to something, I decided in my drive alone that I needed a game plan to take back Christmas. It didn’t take much musing during that drive along Sunset Boulevard to Santa Monica for me to recognize that the best way to determine how I would spend future holidays would depend on my having full control of my time — both personally and professionally. I was going to need to make some big changes in 2016. If I wanted to take back Christmas, I would need to establish some professional autonomy. I decided that I would dedicate 2016 to launching my own business.

The idea of running my own business had always excited me. And after having focused my career on helping other businesses and organizations become great, I would make my own business great in the new year. I had earned my business stripes with a decade and a half of experience. I had worked across a number of industries and disciplines, such as Management Consulting, Media & Entertainment, Social Impact, Philanthropy, Education, Health & Wellbeing. I had experiences in a variety of organizations, including startups, nonprofits, and large corporations. I had developed expertise in a number of areas, such as Strategy, Operations, Innovation, Marketing, Brand Development, Digital Strategy, Strategic Partnerships, Client & Stakeholder Relationships, Project Management, and Business Development. I had the academic cred with a Master of Communication Management from USC and an MBA from UCLA.

I had the business background. But I needed the business idea.

I decided, what better way to help develop a business idea than to learn from entrepreneurs who’d done it themselves? So I began to interview women entrepreneurs. I was learning a lot. And I wanted to share this entrepreneurial wisdom with the world. I launched my website, The Opportunista, to feature my interviews with women entrepreneurs who were dedicated to creating their own opportunities to live their best lives. [Editor’s note: Though the author has subsequently taken down The Opportunista, this beautiful message remains timeless… and has led her to other pursuits.]

I decided that to differentiate The Opportunista, I would develop a platform built by the women who created it: Each Opportunista would nominate her Opportunista to build a genuinely supportive community of female entrepreneurs. More recently, I’ve begun to document my journey of building my business in real time so that women understand what it takes to create a company — even while working a demanding full-time job.

More motivated than ever, I’m now building The Opportunista into a media and education platform by combining my business background and my interviews with women entrepreneurs to create actionable plans so that aspiring entrepreneurs can apply these lessons to build their own businesses. I’m on a quest to demystify entrepreneurship to make it approachable and relatable so that women have the knowledge and tools to create their own companies and shape the lives they want to lead.

The Opportunista’s been up and running for a few months. I’ve featured interviews with about 45 entrepreneurs on the site, have another 30 in the pipeline, and I’m excited for all the directions I’m taking the platform — videos, podcasts, events, e-courses.

It’s a whole lot, especially with a full-time job, but ask anyone who’s ever worked with me and they’ll tell you — I get things done.

As I finish writing this, it’s dawned on me that Christmas 2016 is around the corner. This year has been my toughest professional year, but it’s also been the most rewarding. There’s nothing more thrilling than building something that you can call your own. There’s no better feeling than knowing in your heart and in your gut that you’re working toward building something that matters.

I’ll admit that this year has also been challenging on a personal level. Juggling the full-time gig with the side hustle hasn’t left me with much time for sleep. Delirium is often my new normal, and I know this has to change. The Opportunista is about living your best life — sleep must be part of the equation. I’m working on it.

Another thing that I desperately need to figure out is how to prevent all of my personal relationships, specifically my marriage and my friendships, from disappearing as I build my business. While I recognize that I need to work on this, I’m not certain when I will fully commit to improving my MIA behavior.

While there are mega challenges and responsibilities that come with entrepreneurship, the cons diminish in comparison to the pros — the freedom and sense of accomplishment that comes with living your life on your terms.

There’s something about this entrepreneurial journey that’s become bigger than myself.

Yes, I hope to leave my mark and my legacy, but my greatest hope is to help other women ultimately leave theirs.

So this year, Christmas won’t be like the last.

This year, I’ll be dressing up in a show-stopper cocktail dress. This year, I’ll be carpooling with my folks down Sunset Boulevard. This year, I’ll be loading my plate with turkey and glazed ham—neither of which I like much, but it’s tradition and they taste better that way.

This year, I’ll be spending Christmas the way I want to spend it — with no deadline in sight.

This year, I’ll be happy to have launched The Opportunista.

This year, I’m taking back Christmas.

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