The (Worst-Kept) Secret: How I’m Able To Try Going Pro In The Wine Biz

Vinted on March 30, 2011 binned in going pro

Here’s a snippet of a fictional conversation between me and a wine writer. I use the term “fictional” because it’s not a word-for-word retelling, but (somewhat shockingly) it’s more-or-less a conversation I’ve had with several people in the wine biz in the past few months.

Me: Hey, good to see you again! How are things?

Wine Writer: Goodgoodgood.  Aren’t you quitting your day job?

Me: Yeah, sort of; I’m leaving my IT career late Spring…

WW (cutting me off): How are you making money, exactly?

I’m actually getting sick of these “conversations” (is it really a conversation if the other person only asks you about things that concern them?) – in fact, I might pre-record answers to play back the next time I find myself in one of those; better yet, I’ll get one of those Mr. T talking key-chains and randomly hit the buttons in response to those questions.  That would rock; I imagine it would go something like this:

Wine Writer: Aren’t you quitting your day job?

Me (holding up Mr. T key-chain): Please pose that question to my spokesperson [ presses button on key-chain ].


If someone is going to pry into my life’s intimate details, I prefer that they at least ask about me or my family first and pretend to care about me on some personal level (lesson one about the new world of social media: you should actually try to be social).  As most any 1WD reader can tell you, I don’t know exactly how I’m going to be making a living yet – that’s basically what this series of blog posts is chronicling, so everyone will know those details very shortly after I do – but the truth is that I already have the single most important thing needed for chasing dreams (like switching careers or traveling the world):

It’s called Time.

And to get time, I needed to have money. Already

I guessed several years ago that this day (when I would leave my IT career) was coming.  My middle name is not Nostradamus, but I grew up with very little money, learned quickly that money = time = freedom, and so when I landed lucrative IT career work I did something that turned out to be very, very lucky in hindsight: I stashed away money like a squirrel prepin’ for Old Man Winter.

Not exactly an amazing secret, right?

And it’s not difficult yo do, but like anything else worthwhile, it’s just difficult to do consistently over a long period of time.

If I had the time to give those asking about my income situation a proper answer, it would look something like the following (mini-rant); it probably sounds preachy, and it has little to do with wine, but it has everything to do with riding the alternating waves of prosperity and tough times in your life.  And something tells me that it just might make a difference for a few people out there reading it, so it’s worth taking a chance and posting it.

The simple truth is that if you don’t have the time (and, therefore, the money) to chase your dreams, then it’s not yet time to chase your dreams.

It’s the worst-kept secret of Going Pro: spend less than you earn, smartly invest the surplus, and cash in when you hear the pitter-patter of rainy days on the roof of your life, or the distant but compelling clarion call of your dreams. How you handle your money and your career in any field are deeply personal choices, more akin to parenting decisions than to quick self-help action points, probably – but they make all the difference in being able to handle life’s random events and pursue your dreams.

Because of my long-haul personal choices, I’ll be able to support my family from rainy-day savings for about two years with minimal changes to our lifestyle (which isn’t extravagant, but is by no means  miserly).  That’s because the money never looked like things to me, it always looked like time, like freedom.

While it may be easy to point to my “other” career and say “well, of course you made some money, you were in IT, not wine writing!” you need to bear in mind that there are just as many (if not more) people out of work due to layoffs in IT than there are due to the same in journalism; the case could be made that workers in both fields should have seen the ‘dark clouds’ coming, and once you are over the poverty line the biggest differentiator for your future isn’t the total amount coming in, it’s the difference between what’s coming in and what’s going out.

You have to save money to Go Pro, and saving money takes time, patience, focus and a good relationship with money.  Not understanding how you relate to money is like trying to learn about wines based only on numerical scores – it’s not a real relationship, it’s a shortcut that works sometimes but will never lead to true understanding.

Because of my personal choices, I have a decent net worth – I’m not planning on buying a yacht, and the liquid portion of my cache will certainly run out – and thanks to that I can try Going Pro without going crazy, and hopefully with a sober eye (well, as sober as frequent wine-imbibing allows, anyway!) towards doing what’s best for my family, and looking out for the most sustainable/best-fit opportunities for making money in the (vastly) changing wine media world.

It all comes down to having a healthy, sound relationship with money. If you think it’s odd to have a “relationship” with money, consider that the number one cited fight-starter in U.S. marriages is the topic of debt – I’d say not having a good money relationship is the single most effective way to ensure that the rest of your relationships hit the skids as well.

If your current relationship with money sucks donkey butt, then I strongly recommend that you read a book like Trent Hamm’s The Simple Dollar. It might just change your life for the better.  It will certainly do you more good than looking to me for quick answers on how to rake in the wine media cash (because there aren’t any – and if there are, I sure as sh*t don’t have them yet)!






  • Thome Pellechia

    Ah yes, the doomsayers who really want you to fail and so they point out what to them seems like the obvious.

    On a sober note, however: when I left being an independent industrial show producer to start a winery, I had money saved–after 8 years of trying, I discovered that I hadn't had enough of it!!!

    From there, it was easy to start writing for a living, such as it turned out to be…

    • 1WineDude

      :) Thanks, Tom – as the old saying goes, if you want to make a small fortune in the winemaking biz, start with a large fortune.

      You know, I can't say that I get the vibe from people that they *want* me to fail… I think it's more that a) they are concerned about making money themselves and let that concern get ahead of their manners and relationship-building and b) they just can't compute that it could be possible to succeed in what I am trying to do.

      So I suppose the big caveat here is that not one person has said "you will fail" to me, nor have I gotten the *vibe* from anyone in the biz that they wish failure on me. The vast majority of people have been very, very supportive. But that didn't stop me from writing a mini-rant! ;-)


  • Willybuoy

    Taking the same approach gave me the freedom to retire comfortably at 51. For me their is also an important corollary to what you are saying. You mention that for you money was freedom not things. Freedom from an attachment to things is key not only to saving more of your earnings, but also to focusing on more important areas of your life such as relationships, experiences, spirituality, the arts and so forth. When you are free from having to worry about attaining and keeping things, you give yourself the freedom to focus on and expands into these rewarding areas. Put another way, if you had been worrying about getting that new car, bigger house, latest fashion, it is unlikely you would have pursued your interest in wine to the extent you have, let alone been free to go pro. I do understand your frustration with others attitudes. Most people want to know how I was able to retire so young, not why I wanted to retire so young and what I am doing with my freedom.

    • 1WineDude

      Thanks, Willbuoy – you get exactly what I'm trying to convey, which is the lifestyle decisions being deeper than methods to making money; the trick is to understand that freedom from needing to make so much money in the first place is the first step. Cheers!

  • 1WineDude

    @SanCrittenden – stick around and watch this series and you'll find out as soon as I do! :)

  • Alexandra Fox

    Congratulations! You certainly have one of the more interesting "voices" out there in the wine blogging community.
    Best of luck on your new adventure:)

    • 1WineDude

      Thanks, Alexandra.

  • Renee

    Mr. T, that was brilliant! I love it! Excellent post and very sound advice. Can't wait to read more about your adventure:)

    • 1WineDude

      Thanks, Renee!

  • @myrnaarroyo

    Great post!

    Many people ask me how I can travel for entire summers at a time, start a wine store, or go back to school to study archaeology if I feel like it. I tell them they can do it too if they are willing to make it a priority. I usually get blank looks or a bunch of excuses why they can't do what I do.

    You hit the nail on the head with the time/money connection in this post.


    • 1WineDude

      Thanks, Myrna. Archeology? That kicks ass!

  • Kris Chislett

    Best line in the article: "Not understanding how you relate to money is like trying to learn about wines based only on numerical scores – it’s not a real relationship, it’s a shortcut that works sometimes but will never lead to true understanding."

    Love that.

    • 1WineDude

      :) Thanks, Kris!

  • randyhall68

    I'm right there with you, my brother. About to embark into the great unknown of being self-employed myself. My exploits are far less blog-worthy than yours, and all the trouble and paperwork it takes to launch your own business is more than a little bit daunting.

    Just remember to sleep well, eat well, and remember that it's a process. I'm with you in spirit.

    • 1WineDude

      Amen, Randy – solidarity, bruthah!!!

  • Bryan Maletis

    I love this post.. true and hilarious.. quit your jibba jabba fool! , not you Dude.. you keep fighting the fight

    • 1WineDude

      Thanks Bryan – I think the next 1WD giveaway needs to be the Mr. T Talking Keychain…!

  • Cindy McMichael

    very wise point. i think it also boils down to investing in yourself. If your just saving money for the future, then you aren;t growing as a person like your bank account is. i believe it is important to enjoy life now because that retirement may never come if you dont live that long. overall though, good points

    warm regards,

    Cindy M

    • 1WineDude

      Cindy – there is definitely a balance; the key is more to understand that it’s not retirement to keep in mind, per se, but the balance of your life, your goals, and how money fits into that picture.

      For example, do you really need an iPad, or a full case of wine such-and-such? If you had a different job, with less stress and more enjoyment, would you actually net more even if the job pays 25% less than what you’re making now because you wouldn’t need the same expensive clothes, expensive commute, “toys” to keep up with the neighbors?

      *That’s* the kind of balance I’m talking about – taking a thorough look at your life and seeing how money can enhance your life goals rather than dictate them.


  • Alan Baker

    Ready, Fire, Aim!

    I pulled the trigger on a similar quest five+ years ago and all I have to say is when you have to scramble to find health insurance and adjust the flow of money, don't let panic overwhelm your Persistence of Vision. Trusting that vision when faced with apparent dead ends is key to landing where you should be. It will also force you to be creative, and that's when the magic happens.

    Good luck, and know there is a big community of folks who you can tap for help.

    • 1WineDude

      Thanks, Alan! I appreciate the advice as I'm about to dive head-first into all of that jazz very soon. :)—

  • Chris Metcalfe

    Joe, it is an interesting experience giving up a "good job" to do something that gives you more pleasure. When I left my job last year a lot of people asked the same similar questions. I am not sure if they were really concerned, of if the wanted me to stay by trying to scare me, of if they were just jealous. I still do not know because most of the people with these questions I have very little contact with now. "I pity the fool" who doubts me.

    Seriously though, good luck! I hope to see you in Portugal again soon.


    • 1WineDude

      And what king of fool are those people that doubt you, Chris? DAMN FOOLS!:-)

  • Maxine

    I was laid off late 2010 and it was the best thing thus far for me b/c I have TIME to devote to my passion of wine! With my new founded time, I studied and completed the CSW exam, able to write more frequently on my blog which has led to great opportunities, and currently working on another endeavor. These past three months I've learned it is no one else's concern how you are able to maintain, keep excelling at your craft and the money will come! Much success to you!

    • 1WineDude

      Thanks, Maxine- you too!

  • Mia Malm

    Joe, you hit the nail on the head. I've seen that sometimes people want to follow a dream, but they aren't willing to make sacrifices to achieve it — like start at the bottom rung of pay so you can learn an entirely new business, knowing with hard work and good planning you'll rise soon enough. You're taking a calculated risk but I fully believe you will succeed! I saved up and then left my "safe job" in the midst of the recession. I got many a concerned shake of the head and some not-really-complimentary mumbles about being "brave." I won't say it wasn't scary at first but it's been great and I wouldn't change a thing. Like Alan said, there are lots of entrepreneurs out here who will have your back. Welcome aboard!

    • 1WineDude

      Thanks, Mia!

      Glad to be here! :)

      I have some experience in taking pay cuts in favor of bigger payoffs later – I built my IT career on it, actually. But as you noted, it wasn't exactly devoid of terror-inducing moments! :) Cheers!

  • Evan Dawson

    I imagine this was an intensely personal post to write, and you did so by coming across as honest without being unreasonably testy. And you have reason to be, uh, testy.

    Here's what I wonder, Joe: As you explore this endeavor, are you seeing a kind of merging of old and new media that is creating sustainable careers? Here's an almost parallel: ESPN was tired of getting outhustled and out-scooped by print writers, so in the early 90s they just started hiring the best sports print writers. For a while, the Mortensons and Claytons struggled on TV, but they adjusted. It was a coup. Will there be a kind of merging that takes place between big media and new wine media?

    Regardless, we all benefit when unique voices are successful. Cheers.

    • 1WineDude

      Thanks, Evan – correct on all counts (as usual! :-).

      I am seeing convergence of old and new media all over the place in all kinds of fields, but not necessarily much in wine. YET. I believe it will come and I’m going to be looking at applying the models from other topic/interest areas and seeing what sticks (and what doesn’t) in the wine world.

      I don’t know if it will earn me a viable living, but I do know that with people like you and the other commenters cheering me on, the ride is going to be a blast; I am humbled and grateful to have such great people sending such positive vibes and encouragement – thanks!!!

      • Evan Dawson

        I'm glad you're out there looking for opportunities. I wonder if, at this point, bigger media even wants there to be a kind of convergence, or if that kind of development is perceived as a threat. It shouldn't be. Imagine if ESPN had decided that they were killing in the ratings, so they didn't need print reporters and they didn't need much web presence and they damn sure didn't need to be on Twitter and the like.

        I'd like to see older, traditional media engaging and seeking out opportunities for – corporate-speak alert – synergy. Or, to put it more simply, I'd like to see them recruit the best new media contributors and expand the platforms and products. That kind of reinvention doesn't have to be dramatic, but it can be the key to survival.

        Are you sensing hostility, indifference, or openness to such developments?

        • 1WineDude

          Evan – I'm sensing obliviousness to those opportunities, actually.Last year, in a panel we both spoke on during the Pro Wine Writers Symposium in Napa, Alder Yarrow predicted that we'd see almost exactly what you're describing: that established media outlets would “buy” blogs that were gaining followings and notoriety in the wine space. No one was sure exactly what form that would take or how it would work out in the specifics (e.g., does a single-author blog have value without that author/personality behind it? how would that synergy work? etc.) but generally the group saw it as a logical outcome of where things are going.BUT…The established wine media has shown little interest, I think. I'm not convinced it's because they consider blogs as threatening or not worthwhile; I think it has more t do with them not *considering* blogs *at all*. As in, 5-years-behind-the-times not considering them.

  • Julie

    Your discipline in squirreling money away and making your dreams happen is truly inspiring. I'm in the same boat in believing that focusing on (and saving for) your goals and aspirations is absolutely paramount and brings meaning to life. Matt and I often talk about our 'pipe dream' of having our own winery and take an overzealous approach in saving for it…we hope to follow in you footsteps one day in realizing our dream!

    I haven't heard of "The Simple Dollar" but I looked it up on Amazon and it looks to be a great read. In the spirit of a true saver, I went to my local library's catalog to see if they have it and, sacrebleu, they don't! This will have to be remedied…

    Thank you for a great read today and I wish you all the best of luck in going pro!

  • 1WineDude

    Thanks, Julie – and good luck!!!

  • Chris Metcalfe

    Joe, it is an interesting experience giving up a "good job" to do something that gives you more pleasure. When I left my job last year a lot of people asked the same questions. I am not sure if they were really concerned, or if the wanted me to stay by trying to scare me, of if they were just jealous. I still do not know because most of the people with these questions I have very little contact with now. "I pity the fool" who doubts me.

    • 1WineDude

      Chris – thanks (and nice job working in the Mr. T! :-)

  • Carl Helrich

    Joe, man, you nailed it for me. What's wild is that what you're doing puts into words what's happened to me in the past fifteen years. I grew up poor and worked my ass off. Through a couple lucky breaks and some people who were willing to take a risk on me, I shoe-horned my way into the wine business. Life is all about chasing the dream, whether it's world-class wine in PA or wineblogging. It's tough working against all the local oddsmakers, trying to prove them wrong. You understand…

    You've got the right appoach and a great perspective. You get it, and you've got the goods to make it happen. Keep up the great work. Can't wait to look back on this twenty years from now and see how far you've come. It's a scary ride, but aren't then the best ones always scary?

    Best of luck!

    • 1WineDude

      Thanks Carl – indeed the scariest rides often are the best. Cheers!

  • Lesley

    Hi Joe – I'm late in joining the conversation, but great post! Thanks so much for sharing your 'Going Pro' adventure with us, even though it provokes some annoying encounters. I appreciate what you're doing by sharing this – for someone like me who would love to leave my career in IT to write full-time as well, you are an inspiration (and one of the few wine writers I've seen so far who writes openly and honestly about the subject.) I suspect I'm not the only one, and I guess that's where some of those questions are coming from – they want to do it too! It's a shame it gets expressed that way, though. I wish you the best of luck!

  • 1WineDude

    Hi Lesley – great point, I should tone it down a bit probably… but I am constrained by my genetics! :)Cheers!

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