How easy is it to have a side hustle while working a full-time job? Easier than you might think—especially when it’s fun and fits your lifestyle. Here are four stories from real Wine Guides who wine on the side and love it. Find out how they “do it all.”

A Passion for Wine and Setting Priorities

Ruby Director Jenn Bruns lives and works in Colorado. She’s worked in education for 15 years, and often gets asked, “How do you manage it all?” As the mother of three young children between the ages of 4 and 8 and a wife, life is busy. Add in her devotion to running and prioritizing friend and family time, the question is 100% valid. How does she do it all?

“I have to bring my best, most authentic self to the table EVERY day and do not have time to let little set-backs get me down or dull my shine,” says Jenn. “I ask myself the question everyday: ‘What can I control?’ And the rest, I let go. I think that’s good advice that everyone in this industry can embrace.”

Jenn says that she is very clear and always mindful of what means the most to her, including professional and personal priorities. Then, she structures her days to protect those values.  

“The flexibility Traveling Vineyard affords me is priceless; I am able to work my ‘day job’ and successfully manage my business on my timeframe,” she says. “It certainly doesn’t hurt that the world of wine is my passion—but I know anyone can find success as a Wine Guide.”

I live my life by the mantra from Nelson Mandela: There is no passion to be found playing small – in settling for a life that is less than the one you are capable of living.

Jenn Bruns, Ruby Director

Jenn says her success comes from the support, training, and the sense of community she enjoys as a Wine Guide. “For me, my friendships and sense of belonging has been the glue holding my business together while I manage other aspects of my life. And, it’s important to realize that ‘success’ can mean something very different for everyone, and that should be celebrated.”

Wine Guides on the Traveling Vineyard incentive trip
Amy Richecky, center, and Jenn Bruns, on the Traveling Vineyard incentive trip in 2019 to Dominican Republic.

A Balanced Life and Unexpected Benefits

Dawn Gilman, a Four-Star Leader with Traveling Vineyard, lives in Montana with her family and works full time as a patient access trainer at her local hospital. She launched her wine business in 2017. In her line of work, each week’s schedule can change, so when she wanted to supplement her family’s income, she couldn’t pick up a part-time job that had a set schedule—not if she wanted to have a personal life, too.

“I mainly wanted to earn a few hundred dollars a month, but I very quickly found out I was capable (and hungry) for so much more,” Dawn says.

“I offer my wine tastings Wednesday through Saturday and, to be honest, some weeks are crazy!” When she has two to three tastings during a busy week, things get hectic. “But I have found that having systems in place will help me. I get my tasting materials ready the night before, put my wines in the chiller before I leave for work, and it all works out great! I do social media posts or make phone calls on my lunch break. So, I make it work for me.”

Dawn says the benefits she has received from Traveling Vineyard have helped her both personally and professionally. 

“My wine tastings are fun, so that carries me through the mundane days at work. I’ve gained more confidence with my success with Traveling Vineyard, and that has given me more confidence in my day job as well,” she says. “My director has noticed the change and offers me more opportunities at work.” 

Wine Guide Dawn Gilman
Dawn Gilman launched her wine business in 2017 so she could earn extra income on her schedule.

In addition to the surprise benefit of enhancing her professional skills, Dawn has built lasting friendships. “It’s amazing how I only get to ‘see’ these friends once or twice a year, but when we do meet up, it’s like no time has passed at all!”

Dawn is planning on turning her wine side hustle into something she take with her into retirement, and is putting in the work now to build her business. Who knows, she says, maybe she will even turn wine into her full-time career eventually.

Taking Care of Business Driven by Purpose

Amy Richecky is a Director with Traveling Vineyard in Kansas. Despite being a busy working mom of two boys with a husband who travels, she jumped in with two feet and launched her wine business in 2016. 

“I have had many tries-and-fails and tries-and-succeeds on how to take care of everything,” she says. Her strategy is fitting her wine business into the workday so she can be present when she’s with her family. “It’s tricky, but it has paid off to work twice as hard during the day and have the evening off when at home.”

Looking back through my year and all the experiences we had as a family are in large part to Traveling Vineyard. I think I’ll stick around for a while!

Amy Richecky, Director

Amy says there’s no real secret to managing it all. “It’s about knowing what is important and knowing that it has to get done. We all get to live the same 24 hours every single day, so why not do something with them that gives me a purpose and fills my cup?” 

Amy’s family is her purpose, and why she’s a Wine Guide. “Without the financial side of the Wine Guide life, I wouldn’t be able to pay for karate tournaments (not to mention the gear that comes along with it), and help sponsor my kids’ baseball teams. From the day I started, I put both of my feet in, I have never stopped running and don’t plan to with my business. I look forward to making this a long-term financial plan for my family.”

Julie Posey says she is rocking mom life while working a full-time job and operating her wine business on the side.

Working Smarter Not Harder

Team Leader Julie Posey says she never planned to get into direct sales. She was a busy mom and wife, working a full-time job in her home state of Ohio. But nearly five years ago, Traveling Vineyard found her, she says. 

“I went to a tasting at a friend’s house and then hosted my own in March of 2015. They were both a blast and I loved the wines (Double Date and Fissata at the time … my how my taste has changed)! My thoughts were, if I was going to drink wine with my friends anyway, then why not get paid to do it? Plus, the discount on your own personal wine was super appealing to me. So, I took the leap and joined Traveling Vineyard as my side hustle.”

The day after Julie joined Traveling Vineyard, she found out she was pregnant with her daughter. 

“Talk about poor timing! I did a few tastings at the beginning, but let’s be honest, it’s just not as fun when you can’t sip along with your Guests. To say the least, I had a very slow start to this business,” she says. “I stuck with it though, stayed in the loop, and relaunched my business in November 2016. Since then, it has grown into something I never could have imagined. 

Julie is also a program director for an ultrasound program at a local community college. So how does she balance it all?

“Some days, honestly, I don’t know how I do it,” Julie says. “Between working full time, dance classes for my daughter, swim lessons for both kids, Cub Scouts for my son, fire department meetings for my husband, and my wine tastings, we usually have something going on every night of the week. But, honestly, I love it and I wouldn’t have it any other way.”

Anyone can do this. You just have to want it. Find your balance, have a good support system, and a dream for something more. 

Julie Posey, Team Leader

Julie attributes her success in part to having a supportive husband—who even helps clean the wine glasses. She also has a strategy that involves scheduling all her tasting for one weekend a month, which saves time the rest of the month. Julie loves always having a tasting on the calendar, so she focuses on that during her tasting events. “I try and work smarter, not harder.” Julie also stays connected with her team and with Traveling Vineyard, so she remains engaged and motivated.

“It’s exactly what I need and what I’m supposed to be doing. But I secretly also love evenings where we have nothing going on and get to hang out at home. Balancing all of this can be tough, I’m not going to lie. But I have found a way to rock the mom life, have a full-time career.”

Does the #wineguidelife sound like a side hustle you can handle? Let’s talk wine

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