All the Single Ladies, Now Put Your Hands Up! Our interview with Bachelorista founder Monica Bossinger


Q: Hi Monica! Thank you for doing this interview. I want to start by talking about your autobiography, The Life & Luck of a Bachelorista, because this seems to be where the Bachelorista brand was born. What inspired you to share your story?

A: Thanks for this opportunity, Jaclyn. I’m grateful to be part of this dialogue.

That’s a great question, Jaclyn. If you told me 20 years ago that I would write a book about single life, I wouldn’t have believed you. I never set out to be single in my forties. Although I’ve always been a free spirit and career-minded, there was a part of me that wanted to settle down. And while that desire is perfectly healthy, getting married because you don’t want to be alone isn’t. It was only after making lots of mistakes in my life that I learned that it takes courage to show up alone when everyone around you is coupled-up, and it takes chutzpah to blaze your own trail and not care what other people think of you. For me it was a long and clumsy journey. But I learned to trust myself, follow my instincts, and believe in my value whether I had someone by my side or not. I also realized that the whole ‘you are an island thing’ is hogwash. My life really didn’t open up until I reached out to Lightworkers who showed me a better way to be in the world. In other words, I didn’t go it alone. The Life & Luck of a Bachelorista was just my way of exploring all of these things and exposing “conventional wisdom” for the sham it is. It’s also the roadmap I wish I had years ago when I struggled with my single life.

Q: The concept behind Bachelorista, Inc. is pretty amazing. You’re helping women embrace their single years in a society that stigmatizes this status, especially as we get older. Our reasons for being single vary but many of us feel judged, regardless of why we aren’t dating someone. What made you decide to brand Bachelorista?

A: After escaping the corporate world and moving away from the beautiful chaos that is NYC, I began working with an entrepreneur coach. Both of us recognized that there were many branding elements that I had built into the book without realizing it. I spent decades in marketing, so I think that may have had something to do with it.

Q: Did you create Bachelorista, Inc. with the idea that it will evolve as society does? In terms of women’s rights, as the years go by, we seem to be stepping backwards in many regards. Have you found it challenging to help women recognize their worth and potential during their single years in a society plagued with gender inequality?

A: I love the expression ‘Be the Change’ because it really sums up the idea that we can’t wait on society to do the heavy lifting. If everyone who sees a need and feels led to take a stand does their part, change will happen. Grassroots disruption is powerful. Women are powerful. Together, we can shake things up. But I think it’s equally important that our message is peaceful and one that unites the sexes. Single and married men and women read The Life & Luck of a Bachelorista and enjoyed it – it’s not polarizing in any way. So I think there’s a way of uplifting our single sisters – giving them the fuel, inspiration and information they need to feel great about their place in the world-without tearing anyone down.

There are over 50 million single women in this country. And while we all have our own journeys and challenges to face, the idea that we’re not alone, and that we’re in this together is comforting. Instead of making decisions based upon the fear of being alone, the book encourages single women to make healthy, self-loving decisions. Every woman wants that for herself.

Q: It seems that part of your goal is to reclaim the word ‘single’ and create a definition that functions for the benefit of the woman rather than having it mean that we are ‘without’ a partner. Have you found it challenging to do this?

A: I think perspective is important. I can tell you that Bachelorista is about celebrating single life, and not wishing it away, but if you’re singularly focused on finding Prince Charming you’re not going to be open to the message. But if our goal is to be happy, then we really need to master the art of living in the moment. Studies suggest married women retain the same level of happiness they had when they were single. To me, this means that we need to cultivate our joy wherever we are in life. When our marital status is irrelevant to our happiness, then we’ve arrived. That’s what The Life & Luck of a Bachelorista is about.

Q: I’m often unpleasantly surprised when I talk to single women who judge their worth and success in terms of being with or without a partner. I’ve had friends tell me, “I’ll have it all when I have a boyfriend!” What would you say to these women?

A: As a society we’re constantly bombarded with messages that say partnership is the key to happiness. If this were true, we wouldn’t have crazy-high divorce rates. But these stats don’t stop us from allowing cultural expectations to cloud our self-image the way we do. Let’s face it: we’re up against mainstream madness and a formidable communications machine. We need to see the hype of “You complete me” for what it is: a good movie line. The sad thing about allowing the world to define us is that it keeps the focus off of ourselves. So basically we’re not growing or taking responsibility for our own happiness.

There really is no shortcut to doing the necessary inner work. That’s the Bachelorista challenge to all single women. The only way to prevail against our inner demons, and societal nonsense, is to open our eyes and look inward. There’s a wellspring of self-love there that can see us through anything.

Q: In the interest of full disclosure, I’ve also felt judged by my friends who are in relationships. I’ve been told that I must “tone down my feminism” if I want to be in a relationship but I refuse to compromise my morals, or who I am, just to placate society’s idea of what I should be. Despite my best efforts, I’m still very much aware of the perceptions that exist. Is one of your goals to teach women how to respond to these judgments?

A: Many fabulous women throughout history were told to “tone down”. Thankfully, they didn’t listen. And hopefully you’re doing the same. I applaud you for following your passion. It takes courage to stand up for what you believe in, defy stereotypes and ignore naysayers (even if they are close friends).

I also think that we need to save our best juice for the right audience. When we find avatars, and like-minded people, they lift us up, and give us the courage to keep at it. There’s no substitute for solidarity and sisterhood. As far as relationships are concerned, many men have made great strides in supporting feminism, too.

By following your own path and empowering yourself, you’re paving the way for other women to do the same. Bravo!

Q: Is there one person who has been instrumental to your brand’s success?

A: Isabelle Fregevu is Bachelorista’s illustrator. She’s a genius at visually executing the feel and sensibility of our brand. Bachelorista wouldn’t be what it is without her. On a personal note, I feel blessed to have found such a wonderful friend.

Q: How has creating this brand helped you grow as a woman?

A: I’m an introvert, so putting myself out there is never an easy thing to do. 
But I do believe that nothing makes us happier than when we’re following our life purpose. Finding my voice and drumming up the courage to speak my truth wasn’t easy. But I’m more excited than ever that I did, because now I’m helping other women find their voices.

Q: What does the future of Bachelorista, Inc. look like?

A: That’s a great question. I wish I could say that I have it all figured out. Creative endeavors, especially ones with no backing like mine, get traction at the grassroots level or they don’t take off. Whatever happens, I’ll continue writing and empowering single women in any way I can.


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