"No one works harder than a woman who refuses to ask for help." I’m not sure who said it first, if you know, drop it in the comments. This quote is my autobiography. Because she’s me. For over seventeen years as a single mom, and even in my childhood, self-reliance wasn't a choice; it was life showing up and molding me to be the person I am today. And for years, when I thought about asking for help, the message was loud and clear:
🛑 “Don’t ask. That's embarrassing."
🛑 “What if it is a performative yes?”
🛑 “Figure it out. You got this.”
🛑 “People will disappoint you.”
So I became the queen of self-sufficiency. I learned to carry it all on my own, parenting, the career, the house, the heartbreak. I carried a lot of baggage, and it got heavy. Bone-crushingly heavy.
There are so many reasons why I didn’t ask for help. It wasn’t just pride or fear (though that was a big part of it). For me, it was the anxiety that if I reached out, the people I cared about, respected, or I thought genuinely cared about me would reveal themselves. And I wasn’t ready for the hard truth, that maybe these folks were not truly in my corner. All of these “what if’s” popped in my head. Like, their help wouldn’t be real, more surface-level, performative, polite. And worse, I’d feel like a failure for even needing it.
I saw a short clip with Kevin Hart talking to Issa Rae this week, and it pulled to the surface this thing I knew I needed to unlearn, but avoided quite often. Kevin mentioned how we assume people are too busy, so we don't reach out, yet in reality, a lot of people want to help. They want to be a superhero in someone else’s story. Yup, I had to sit with that, as I personally love helping people when I can. Folks who ask me for help, I never think less of them, judge them, or anything. I just want to pay forward what someone has done for me. But when I wanted to ask others for help, I’d convinced myself I didn’t want to burden anyone… I never stopped to think maybe I was denying someone the gift of showing up for me. Or, that I would make a meaningful connection I didn’t even know existed in the process.
So before I sugarcoat this and get you believing everyone has a good heart and good intention, the truth is many do not. And some of my beliefs about people turned out to be true. I spilled the tea on one of these stories in my book, Beyond the Mission Statement. Will people let you down sometimes? Yep. Absolutely. It’ll sting. But every time they do, you get clearer on who’s in your tribe and who’s just in your texts. So my EspressoFueled friend, that’s clarity. That’s growth. That’s freedom. And most importantly, you’re empowered to build relationships and tribes that are genuine and meaningful. At the end of the day, isn’t that what’s most important?
The messy thing about people is that, sometimes, they can truly amaze you.
I’m a networker at heart. It’s the lifeblood of my business, how I build my brand, and frankly, how I’ve landed some incredible roles at some fantastic companies.
Yet there was one company, a giant. A dream I have forever wanted to work at. This company is notoriously hard to even get an interview with.
Last year, I found myself, your girl, absolutely geeking out at an event in their New York office, I met someone amazing. He probably doesn't even realize the sheer courage it took for me to approach him, to follow up with that email, to brave that first exploratory call. It was a leap of faith into the terrifying unknown of "what if they say no?" But months later, when a perfect opportunity surfaced, he remembered me. He thought of me. He made the introduction, connected me directly to key leadership executives. And in those conversations, I was invited to to chat with senior executives at Cannes.
Nothing has come to fruition yet, no big offer materialized. But the person I was so afraid to ask for help, the one I wasn't even sure was "in my tribe," has shown himself to be an ally of the purest kind. No matter what happens, that quiet, genuine support, that unexpected belief in me, is something I will carry in my heart, forever grateful. It reminds me that bravery in connection can sometimes lead to the most profound and unexpected gifts.
And buttercup, you should know asking for help is one of the bravest things we can do? It means:
You’re emotionally mature enough to admit you’re human.
You trust someone enough to let them hold a piece of your load.
You’re finally ready to build a genuine community, not just carry the weight alone.
So how do I ask for help, when it makes my skin crawl? It still is the hardest thing in the world to do for me personally. In fact, I don’t even like to ask my husband to open a jar for me. However, this is the framework I live by. PR4
Pause: Notice the moment you start telling yourself, “I should be able to do this alone.”
Reframe: Ask, “What would I say to a friend who felt this way?”
Reach Out: Start small. Ask for something specific. Give people a chance to show up.
Reflect: Notice who responds, how it feels, and what you learned.
Repeat: Keep practicing. It gets easier. Not perfect. But easier.
You’re building community, not a transaction sheet. But, this process helps you discern who truly has your back, who aligns with your values, and who will move with you in solidarity.
I'm going to be completely honest here. Not only do I still struggle with this, I’m still learning this. Even today, every time I ask for help, it feels like swallowing glass. What I’m realizing is that my independence was never the whole story. It was survival. Now, I want community. And that means letting people show up for me. Even if there is a risk they may let me down, I cry, or just get completely embarrassed. Even if it’s humbling. I promise you, it is hard but it’s worth it. So maybe this is your permission slip too. To stop being the superhero all the time. To ask for what you need. To trust that help doesn’t make you weak and try to anticipate that people will surprise you. We need to stop the fear of rejection before it even happens. That’s the risk. But it’s also the gift. Trust me, you want to know who will stand in the storm with you, not just clap when the sun comes out. "New edition, can you stand the rain?"
Asking for help builds community. It creates a real connection. It invites people into your story. And it reminds you that you don’t have to carry everything alone. And not asking could cost you something special.
Until next time, own your story. Burn the script.
XOXO Jenny