I Spent Ten Years Ashamed of Being Single

Share this

I Spent Ten Years Ashamed of Being Single

Share this

I was lowering my standards, erasing my dealbreakers, and widening my willingness to settle by the day

“A future that upholds women’s independent ambitions will always be out of reach if we’re telling young girls and women that independence is a character flaw.”

From researching the history behind words like “spinster” and “old maid to the experience of planning my wedding, I’ve been consistently disillusioned by the extent to which a woman’s worth and place in society is still defined by her marital and motherhood status. And the ways in which those societal pressures and expectations can undermine a woman’s own ambitions.

So today, I’m pleased to invite author Shani Silver to Too Ambitious, to share her honest, unfiltered experience of letting go of those expectations and the lessons learned in the process.


I spent ten years ashamed of being single. I know, starting out on a high note, right?

For an actual decade, I devoted countless hours and oceans of mental energy to “finding someone.” It was very much a daily chore, or a “second job” as I’ve often heard it called.

I wasn’t especially lonely, I didn’t necessarily feel “incomplete,” but what I did feel was a strong sense that being single was wrong, embarrassing, and in need of repair. So for ten years, I tried to fix what I assumed was wrong with me, so that I could be in the “right” club, the coupled one.

I was dating so that I could check an item off a to-do list. Maybe this wouldn’t have been so bad, if dating had ever actually worked.

In ten full years of trying, I never once had any success to show for my efforts. Nevermind that dating had turned into a digital face buffet where my value was perpetually dismissed and degraded and dating apps themselves had become for-profit industries with absolutely no vested interest in users actually meeting partners—just the opposite, they make more money the longer we are single. None of these things ever dawned on me. All I could see was how embarrassed I was to still be single with each passing year, while everyone in my age bracket paired off like socks.

Call it exhaustion, frustration, or pure boredom, but eventually, I started asking questions:

Why was I dating when dating was so punishing?

Why was I volunteering for an activity that hurt my feelings and lowered my self-worth?

Why was I spending all of my free time searching for someone else instead of focusing on me and the things I enjoyed?

What was really so bad about being single?

For me, it wasn’t being alone, it was the shame of being alone.

I was lowering my standards, erasing my dealbreakers, and widening my willingness to settle by the day—anything to avoid more shame of being single, more looks of pity, more baseless and uniformed dating advice.

Nothing mattered other than finding something that would “stick.” It was the darkest, most desperate point of my singlehood, and I am so deeply grateful for the dawn. I also deeply grateful that I didn’t meet someone while I was so dedicated to running from shame.

The interesting thing about shame is that it doesn’t come specifically from within us. It’s an internal response to an external source, or a presumed or anticipated external source. That’s a long winded way of saying: We care about what other people think.

While a certain level of self awareness is fine, letting the opinions of others drive our thoughts, feelings, and actions can lead to a life that feels lost, like it doesn’t even belong to us. If we don’t stop for a moment and ask ourselves what’s actually motivating our actions, it can feel like we’re devoting ourselves to running from shame.

So why talk about shame in a space dedicated to ambition? Because shame and fearing what other people think can stand in the way of it. How could we dream and plan freely, and what could we accomplish, if “what other people think” wasn’t a factor? Rather than taking in societal conditioning and expectations and letting those things drive, we can find genuine freedom in identifying motivation from within. It can start small, and simply.

When was the last time you asked yourself, “What do I want, and why do I want it?”

One way I love starting a new year is crossing off every “why” that comes from the expectations and programming of other people. I’m always far more motivated to dream, work, and explore when I put my own desires above what I’m “supposed to do.” That includes my professional and personal lives.

I believe shedding shame is a conscious decision that is then put into practice and developed like a skillset over time. It’s not enough to simply decide for yourself that what other people think no longer matters. It really starts to solidify when you take action to prove to yourself that you can be internally motivated, and do what you want, rather than what’s expected of you, and discover that the world doesn’t end afterward. You reinforce for yourself over time that shame and “supposed tos” really do stand in the way of ambition, and no one deserves to have power over your future.

It’s not often that we associate the shame of singlehood with hindrances in other areas of life, but they’re legion. Shedding single shame and connecting with my sense of internal motivation (and validation!) is one of the greatest gifts I’ve ever given myself and my career. I look forward to my future relationships. But I don’t fear the days of my life lived before them, because I’m no longer ashamed of what other people think of my singlehood.

My singlehood isn’t happening to anyone else, it’s happening to me, and I like my single time.

I like the space and freedom it affords me. And I like that my single years were the ones I used to let go of what doesn’t serve me, in order to pursue so many things that do.

Shani Silver is a humor essayist and podcaster from Fort Worth, Texas who began writing at age six. Her name is pronounced like “rainy” with a “sh.” Her book, A Single Revolution: Don’t look for a match—light one, published in the fall of 2021. Her podcast, A Single Serving Podcast, launched in April of 2019 in the hopes of giving single women content that—for once—didn’t revolve around dating, and to support women around the world in reframing singlehood. Following ten years of use, Shani permanently deleted her dating apps in January of 2019. She has loved her life ever since.

P.S. I got a chance to join Shani on her podcast to talk ambition, what it means to feel entitled to it, and the milestones we do and don’t (but should) celebrate along the way. You can check out the episode here. And if you have a story about how your relationship status (and the response to it) has impacted your relationship to your own ambition, let me know in the comments.

Image: Oliver Rossi/Stone via GettyImages

More Articles

You May Also Like

If you’ve ever been called “too ambitious”, this is for you…

Join the “Too Ambitious” newsletter for real stories and expert advice on navigating work, money and ambition on your own terms.

When you sign up to our newsletter you agree to our Terms and Privacy Policy