You spent your 20s working toward building your dream career, but now that you’re in your 30s, what do you do when you’ve, well, changed your mind? Or maybe you never quite figured it out, and you’re now ready to commit to something you’re passionate about, whether it’s a job, a city, or just a new way of life. To celebrate the career changes that can come at any age, we’re debuting a new series called Second Life. Each week, we’ll hear from women who got over their doubts and fears and made the biggest changes of their lives.
A lot of us have no idea what we want to be, even after we’ve “grown up.” For Masaye Waugh, her career in the bar industry didn’t start until she was in her 30s, when she began working as a cocktail server to survive the high cost of living in San Francisco. “When the going gets tough, the tough pick up a tray,” says Waugh, now 44. Last year, with over a decade of experience in the business, she started calling—not just pouring—the shots after partnering with a friend and opening up their own neighborhood bar, Ho’s Bootleg Tavern, in Russian Hill. Here’s how she made it happen.
MYDOMAINE: Tell us about your first career.
MASAYE WAUGH: After college, I graduated with an English degree and no idea what to do. My older sister was a newscaster, and since she was my role model, I interned at news stations after college. But it really wasn’t the thing for me. It took me a lot longer to figure out [what was]. I had different jobs in public relations, front-desk administrative assistant stuff, and retail, but I never liked being in an office. Sitting at a desk always drove me crazy—I need to move around and interact.
Then I got my own apartment and basically needed to pay rent and school debt. I called it “big-girl rent.” At the time, I was working at a Betsey Johnson boutique, and I told a friend I was having problems making rent. She said, “Why don’t you start cocktailing?” And that’s how I got into the bar business—as a cocktail waitress. I felt so stimulated. Things are flying at you left and right. It’s a constantly changing environment. In 15 minutes, your whole situation is different—you might have a dead bar that’s suddenly full.
MD: What triggered the need for change and owning your own place and why?
MW: The thing about the bar business is that everyone eventually wants to bartend. That was my long-term goal, and I ended up making it. I think when I started bartending, I had the notion I’d start doing creative writing. Not a lot of people bartended as a career at the time. It was before the whole craft cocktail thing, back when it was more of a party. Over time, you realize, This is my career. I remember this quote, “Be careful what you get good at, because it’s really hard to get good at something else.” I grappled with it for a long time.
Most bartenders had no job security and were hired based on looks and personality. The longtime bartender’s career curve reminds me of an aging Hollywood actress’s: Everybody knows you, and you’re getting older; the owners think you’re played out and want fresh faces. You fear someone will walk in and take your job one day, and sometimes they do. It can be a dead-end situation full of insecurity, unless you end up owning. I had been bartending for 13 years, so it was time for me to own or get out of the business.
MD: How did you go about making the transition to being a bar owner?
MW: I tried over and over again for years and years, but I never followed through. Five years ago, I took a business class through the Women’s Initiative for Self-Employment. It was for low-income women who wanted their own businesses. The funny thing about it was that a lot of it was very emotional. They asked us things like, “Do you think people will like you if you have money?” There were probably a lot of questions they wouldn't ask men. It made me realize that a lot of women think they will no longer be liked if they have power.
That was the first time I worked on my business plan. I cut up inspirational quotes and made this sprawling vision board. It had pictures of a bar I wanted to own; an ethnically ambiguous baby girl; a Shiba Inu (a breed of dog); Oprah giving a gift to her audience (I think it’s such a privilege to be able to give); a quote that says, “Beauty, beauty, don’t be afraid to face the world.” The funny thing is that I found this giant picture of a wedding ring and cut it out and put it on the top of the board and realized I didn’t really want that. I reshaped it and made it represent self-love. And at the end of the year, I didn’t achieve any of that. But I kept slowly pursuing these dreams over time. Now after five years, I have most of it.
I assembled a mini team. I reached out to a successful friend, Cory Hunt, who owns Jackelope in San Francisco, and said, “Can you help me open up my own bar?” And he said, “Yeah, sure, whenever you’re ready.” I had probably asked him a few times over the years, and finally I met up with him.
Then I asked my longtime co-worker Jerrid Wood, who had reached the ceiling [as a bar manager], to co-own with me. He was like me. He just needed someone to tap him on the shoulder and say, It’s time to make the leap. The next thing I knew, he was dragging me by the hair to get it going.
MD: What were the biggest challenges and why?
MW: For a couple of years before I opened the bar, I was with an abuser, and then in a resulting court case, and then in therapy. I saw I had made bad choices, and I built my self-worth back up. After that, I met a wonderful man and—I didn’t think it possible at my age—I became pregnant right when Ho’s Bootleg Tavern started to materialize. My journey has been a lot about self-love. I’m still working on having money and on actualizing being able to give like Oprah. But I have two dogs, I have a bar, and I have a 3-month-old baby girl—that continues to be a challenge. I don’t get a whole lot of work done when I’m watching my daughter. I’ve always known I’m not Superwoman, and that’s okay.
Another huge challenge was negotiating the lease for the bar. Without a good lease, you’re screwed. Luckily my mom, who has always been supportive of my dreams, was a co-signer on the lease. She was a civil rights activist. Her generation, they changed the world. My generation, we were raised on television and don’t have as much conviction—we have to find our reasons to be.
MD: Did you ever feel like you had made a mistake becoming an owner versus an employee?
MW: No. I had nothing to lose, really. I was living hand-to-mouth as a bartender for many years in San Francisco. I’ve been treading water my whole life here, in one of the most expensive cities in the world. Professionally and personally, I’m constantly learning and evolving. My goal isn’t to be a mega-millionaire; I envision having two successful, comfortable bars and a healthy, harmonious family.
MD: What’s the most important thing you have learned during this whole process?
MW: I met a lot of talented, smart people as a bartender, and all these people I met over the years came into play. I always say, “I may not have that talent, but I know people who do.” Making the bar happen was largely coordinating relationships. So don’t be afraid to reach out.
MD: What's your best advice for someone who wants to start over or make a big jump in their career?
MW: Clean up your personal life. Get therapy if you’re making destructive choices. Don’t get absorbed with someone who abuses you physically or mentally. If your partner is dragging you down, you’re not going to get very far toward your hopes and dreams.
Also, I’ve concluded I don’t like tackling ambitious projects by myself. It’s not as inspiring or motivating when I’m on my own. When you work with someone else, you’re accountable. So collaborate. And don’t be ashamed if you don’t instantly succeed. Put one foot in front of the other and you’ll get there at your own pace.
Ready to pick up your own metaphorical tray? Let us know if you've been inspired by someone's second life. You may see their story on MyDomaine next!