From Playing It Safe to Stepping Into Power
By Samantha Markey
Founder of the Plandipity Doers Membership Community
The moment I stopped dimming myself was surprisingly ordinary and incredibly powerful. I was sitting in a women’s networking meeting in April 2021, surrounded by inspiring entrepreneurs. My plan had been in place for a couple of years: I was going to quit my hotel career that year and go full-time into my business, which had evolved from photography into creative marketing services. But then COVID hit, and my husband was shifting careers too. I pushed my timeline back, playing it “safe.”
The weekend before, we’d traveled to La Jolla, CA, for an end-of-life celebration. We stayed with my husband’s aunt and uncle—self-made and generous. I asked them all the questions. I listened to their stories, their sacrifices, and what it took to build a life of freedom. I was also reading You Are a Badass at Making Money by Jen Sincero (huge fan!), and I remember thinking, “What exactly am I waiting for?”
Right then, during that meeting, I stood up and declared I was going for it. I quit my job that Monday.
That bold move wasn’t just about me, it was about what I wanted to build. The Plandipity Doers wasn’t even launched yet, but the vision for it was the reason I knew my work mattered. I didn’t just want to create marketing strategies. I wanted to build a system, a space, a community where women entrepreneurs felt supported, seen, and empowered. A space where we could get things done, together.
That idea felt familiar. My late mom had always dreamed of starting an art collective, a place where creatives could sell, connect, and thrive without the pressure of overhead or isolation. Plandipity Doers isn't a brick-and-mortar art space, but the heart behind it? That’s my mom’s spirit living on. That made my heart smile and gave me purpose.
But let me be honest: it hasn't been easy. In fact, once the idea became real, I started playing small again. The fear of rejection hit harder than it ever had when I worked in hotel sales. This wasn’t just a job, it was my heart. I paused, hesitated, and held back.
It wasn’t until I faced the real possibility of letting it all go that I asked myself: “How can I give up when I haven’t even really tried?” That’s when I hired my business coach, Connie Kercher, and started really showing up for my dream, and for the women I want to serve.
So, how do women lead unapologetically?
We stop waiting for the perfect moment. We stop making ourselves small to make others comfortable. We get clear on what matters to us, and we give ourselves permission to chase it wholeheartedly even when it’s messy, imperfect, or scary.
For me, unapologetic leadership looks like this: being honest about what I want, trusting that I’m worthy of it, and taking action even when it feels uncomfortable. It’s knowing that building a life of freedom doesn’t have to look polished every day. Sometimes, it looks like messy buns, shifting plans, and voice notes from the bubble bath. And that’s okay.
I lead by living it. No apologies.
Connect With Samantha
@morethanserendipity
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