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The Life & Luck of a Bachelorista with Monica Bossinger

Monica Bossinger is the founder of The Bachelorista
Monica Bossinger

Being single is a fact of life one way or the other. From never married to divorced or widowed, it’s a marital status none of us escape either at one point in our lives or throughout one’s life. For better or worse, being single is more common these days than in past generations. With the advent of singleness comes a certain discrimination, especially after a certain age, especially for women. Single seems to be perceived as a sign that something is wrong with a person for their lack of a significant other. Despite the fact that being partnered, in some cases, can be a recipe for dysfunctional patterns and behavior for both persons, many people attribute positive qualities to those who are partnered without any supporting evidence other than a wedding ring. Writer Monica Bosssinger of seeks to change the prejudice against single women through her blog which celebrates life. Whether single or coupled, one life is all you’ve got, making the best of it is the best option.

What is Bachelorista Inc. all about and what was the catalyst for you to develop it?

I founded Bachelorista and wrote The Life & Luck of a Bachelorista to celebrate, support, and empower single women. There’s so much to explore around the topic, but more than anything, I wanted to create something interactive where single women have a voice, feel appreciated, and are understood - especially amidst all the white noise of mommy bloggers. I’m single in my late 40s, with many friends in the same space, and instead of wishing our status away, I think it’s time we dismantle the stigma and start having fun.

How did you decide what to include in the book and blog as a tool to celebrate being single without discounting the possibility of finding love at any age?

I believe the book message “Blazing through your single years like a rock star” is possible for every woman, but none of us get there without making healthy choices in every area of our lives – including love. The book is a wake up call about being true to yourself and chasing down your dreams, and not settling for mediocrity – in anything! The better women feel about themselves, the better choices they make. So self-love and a healthy self-esteem are two entwined themes and must-haves in a Bachelorista’s clutch. Healthy relationships don’t happen accidentally. Healing and getting out of our own way so that we recognize what’s healthy is a big part of that. Once we’re happy being alone, the good guys always come.

What have you learned about why being single, for either gender, is pathologized and seen as a sign that something is wrong with the person?

I believe that we feel pain in our psyches and in our communities around issues we fear. The singles stigma isn’t a result of one thing; it’s a perfect storm of religious, societal, familial, and political beliefs – with sexuality thrown in to make it even more complex. As progressive as we think we are, we’re still dining on the crumbs of another generation. And I’m not saying the institute of marriage is necessarily outdated, but that we need to rethink what real partnership is. Our expectation that someone else will make us happy (or that marriage will) is what trips up a lot of people.

For all of above reasons, there are obvious prejudices against unmarried people. Mix that with a sensationalist culture, the dating scene, pressures from family and friends, and our own issues, and it gets messy in a hurry. I’ve felt marginalized for not having a plus one in my life many times- at work, around the family table, and socially. We’ve got to take meaningful steps to open up the dialogue and find a way to embrace single people. It’s my desire that Bachelorista serve single women in a way that society hasn’t: by listening, providing resources, tools, products, empowerment, and support.

Do you see the Bachelorista book series and brand as a forum for counteracting and calling out the prejudice against singles? In what ways is the discrimination against singles similar to other kinds of prejudice?

In the same way the LGBT community did, unmarried people will need to be more united in their efforts to ensure equal treatment. Why should we pay more for services like health care, travel and car insurance than our married counterparts? As single people, we also don’t receive the same tax breaks, mortgage approvals, and promotion opportunities. Since singles make up more than half the U.S. adult population, it’s appropriate for us to ask, “Where’s the love?”

But I’m not an activist for the single population pushing for policy change. I’m an author with a message of empowerment for single women. I’m also a businesswoman who wants to best serve the immediate needs of unmarried women. The Bachelorista brand is a newborn, but we’ll always parallel path support and our offerings.

Tell me more about the connection between Bachelorista and Mutual Love Society?

I’ve read dozens of books like He’s Just Not that Into You, but they mostly discuss women in the context of relationships with men. Once I finished the book, and the initial buzz wore off, I felt disconnected once again. I wanted to create a living, breathing, malleable community that embraces our fab natures and continues the conversation from The Life & Luck of a Bachelorista. I thought it was important to give this community a name. In my book, I call it a Mutual Love Society, which my BFF Laura penned during an email conversation we had about our friendship. Facebook was a natural place to kick around ideas, inspire, and support each other. Mutual Love Society is our virtual hug.

10% of your profits go to charity, which charities do you support and how did you decide upon them?

That’s an important question. Although Bachelorista is just starting out, I wanted to come out of the gate with the things that were important to me. In the same way I introduce spirituality in my book, I wanted the action of giving back to be built into our business plan. On I call this The Giving Tree. I have a personal connection to all three charities we support; Crossroads, Shout Out Loud Productions, and Four Bands, and you can read how here: I’m looking forward to the day I can hand each of these organizations a big check. For now, we are poised and hopeful that someday we can help make a difference.

How does the blog aim at counteracting the stigma against singlehood?

On the day to day, my message is one of empowerment. When women feel strong and on fire, they don’t see or feel the glass ceiling. They aren’t thinking of the ways they are held back. Seeing opportunity is critical for all of us. It’s also the lifeblood of business and the characteristic of a great entrepreneur or innovator. Once we get passed the mind games of the single stigma, and being a woman in a man’s world, we outperform men in a myriad of ways. That’s the juice. I don’t have an agenda on my blog; I write what moves me. Sometimes it’s personal, other times it’s a love letter to Bacheloristas and a reminder that we’re in this together. Every piece I write has an element of humor mixed in. I don’t take myself too seriously.

Are there any articles on the blog that most stand out in your mind and why?

I had a great time writing, We’ve Come a Long Way, Bachelorista! (10 Simple Ways Bacheloristas Can Make Life More Meaningful in 2014). I took my favorite quotes from Twitter last year and then crafted a manifesto relatable (hopefully) to single women. This quote by MLK stands out, “Our lives begin to end the day we become silent about things that matter.” There is something so powerful about that message. To me it means finding my truth and my voice, and not worrying about how people will react. I think today’s women are ushering in a more graceful feminism, and it’s so much more powerful than the angry and self-righteous banter that made us squirm.

Ultimately, what is your highest vision for the social impact of Bachelorista on modern society and pop culture?

There is so much power in conversation. Just talking about the things that we’re experiencing is so important. Shifts arise naturally from that honest place. I put the best of myself in The Life & Luck of a Bachelorista. And I will do the same with the entire book series. I’m busy at work on The Bachelorista Guide to Financial Happiness, which I’m writing in collaboration with financial advisor Melissa Lydon. And I’m also teaming up with Ivana Demrovsky on The Bachelorista Guide to Style – both Berkshire-based professional women. Isabelle Fregevu-Claracq is Bachelorista’s illustrator and a genius at visually executing the feel and sensibility of the brand. I can’t wait to see how Bachelorista evolves alongside her.

The Bachelorista registered trademarks are in place so we’ll be serving single women in many sectors – including a clothing line, electronic goods, and entertainment. I also hope to partner with service companies to offer Bacheloristas discounts in travel, spa services, etc.

I don’t expect all of these things to happen overnight, but if it’s meant to be, like I feel it is, it’ll be fun.

I understand you have a man in your life, where there any thoughts about not continuing with Bachelorista?

Hell, no! He's actually Bachelorista's biggest fan. After a mutual friend told him about me, he read my book and wanted to meet. We’ve been together ever since. He’s a genuinely great guy, and someone who believes in me wholeheartedly. I had tons of work to do before I got to a place where I could hold a space for what we have, and I’m so happy I put in the time. I still have a way to go, but it’s so much easier when you’re on the downhill side. I do find it maddening how differently I'm treated when I have a man by my side. And that’s exactly why I’ll never stop empowering Bacheloristas!

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