I asked this very question of this community, for myself, about a year and a half ago: Getting into the business: finding good harvest internships - Cellar Rats (ITB) - WineBerserkers
I got a lot of really good advice from a lot of people - very practical, no-nonsense, but not discouraging, which I really appreciated. I ended up getting a harvest internship at Williams Selyem, which was a fantastic experience, and transitioning into a wine lab after that, which has worked out really well for me and I expect will remain a good fit for some time.
I’m sure there are important differences between wanting to go into production vs. winery sales/marketing vs. retail. And then I know some people try to just start their own winery or vineyard from scratch with no experience - I just hope they have a lot of money to burn.
If someone says that they or their friend/family member is interested in getting into the production side of the business, my number one recommendation would be for them to talk to a few people who’ve worked harvest and then, after hearing about the hours (for the first half of harvest at WS I worked ~5am-6pm six days a week, for the second half I worked ~2pm-3am, and I know some people work much longer hours than that), the toll on your body, the lack of time with your family, and in most places the low pay and lack of benefits…well, if after that they’re still interested, they should work a harvest, especially if they have a job that would allow them to take 2-3 months off and then come back. Then if they enjoy the harvest and don’t mind living on very little income, they can try to stick around.
Then there’s also the generic advice for people who are thinking of changing careers: make sure you have enough money saved up for everything to go wrong; make sure you have a backup plan if you can’t find any penetration in your new endeavors; and make sure you have people around you to provide emotional and, if necessary, logistical support.
I don’t think that the wine industry is nearly as sexy and enticing as people outside it think it is, but it has its moments, and you get to live and work in pretty awesome parts of the world. When I get off work, drive 5 minutes to Shiloh Ranch, hike 15 minutes up to the top and drink a cold beer looking out over the Russian River Valley, I’m pretty grateful that wine brought me out here to work on something I love.