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The First Day of the Rest of My Life

“So when are you going to quit your day job and focus on wine?” Everyone from close friends to well-meaning strangers have asked me that question for years, and for the first time, I actually have an answer. The answer, folks, is today.

Last week I left my company’s office for the last time, to do what people have been asking me about for more than a decade.

It remains a well-known cliché: to have worked so hard in order to achieve something, and then in the moment of attainment, to not entirely be sure what to do next. To become unmoored and momentarily confused at the absence of headwinds that have been present so long that they have become a part of you.

Yes, this all feels very weird.

For more than fifteen years, I have been working my tail off as an entrepreneur. I started my own experience design and consulting company in 2005 with a partner, and ever since then — even on vacation — only twice have I gone more than a few days without checking my work e-mail (a few weeks’ paternity leave and a fly fishing trip off the grid in Alaska). As a small business owner I found it impossible to ever truly leave work behind.

Over those 15 years of working 50- or 60-hour weeks, the business grew, slowly but surely. I was able to support my family, save a little for retirement, and hire some more people. It was difficult and rewarding. We did good work, and were successful, counting brands such as Google, Twitter, YouTube, Room & Board, Gymboree, Blurb and Franklin Templeton as clients.

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Almost exactly one year prior to starting my company, I also started a blog. Originally it was just as a way of learning what blogs were, because my clients at the time were asking me about them. There was never any question about what kind of blog I would write. Wine had long been an obsession, and writing a natural activity for me as a consultant in the domain of marketing.

Vinography and my business were born only a year apart, and they grew together at first. Being the boss of a young and growing company meant that I could control my own schedule. No one was going to yell at me for skipping out of the office one afternoon to attend a public wine tasting, and I could fly off to wine regions around the world several times per year on press trips without anyone hassling me about how much paid time off I had accumulated. Life was good.

Vinography in the early years was an endless source of joy, and a true creative outlet. I’d write 5 to 10 posts each week and still have energy and inspiration for more. Wine blogging was in its infancy, and I was helping to define and shape the medium. I was happy. My “night job” as I called it (really, what I did instead of watching TV) was endlessly satisfying. I won awards. I spoke at wine events. I was offered a column on Jancis Robinson’s web site. I profitably self-published a wine book that Eric Asimov liked.

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But the consulting business grew in both revenues and staff. We sold the company (really, merged it) to a friend’s agency in 2014 to become a larger, more capable firm. Some of the work weeks crept upwards from 60-hours closer to 70. My daughter stopped napping. Life got more complicated and more busy.

For the past six or seven years, I’ve watched and almost viscerally experienced my avocation — my primary personal passion — squeezed to the point of near death. Those of you who are faithful readers can’t help but have noticed the reduction in the volume and quality of my writing. For the last couple of years from my perspective, Vinography might as well have been on life support.

But leaving behind a company you started and a solid income to pursue a dying art that pays on average less than minimum wage is not an easy step to contemplate. Especially in the San Francisco Bay Area.

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So I waited. And worked. And eked out the little bits of time that I could find to feed my blog and the passion that still drove me to write.

Then about a year ago, my business partners and I sold the company properly, and for the first time I felt like maybe, just maybe, I could take a sorely needed break from the constant grind.

So, call it a sabbatical. A hiatus. A self-imposed residency at a one-man writing workshop. A self-indulgent reward for a decade and a half of hustle.

So now, pandemic and its imposition of house cleaning, cooking, and home schooling duties notwithstanding, I am going to indulge my passion. I’m going to write about wine like it’s actually my job to do so. I’ll do a little consulting on the side, just to make sure we can still pay our bills, but the vast majority of my time will be focused on Vinography.

There’s some sprucing up to do around these parts, and my focus will first be to get the site back to the quality and volume of content for which I can be proud again. After that’s taken care of, who knows what more I might be able to do? I’ve never had the opportunity to find out, but new things are now possible.

I hope you’ll continue to come along for the ride, and see where this new beginning on an old journey takes me. I, for one, can’t fucking wait.

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