4 Questions That Always Come Up in my Coaching Calls (and My Honest Answers…)
While every client I meet with comes to me with their own unique needs and goals, I have to admit, I hear these 4 questions all the time:
“Where do I even start?”
“Is starting a business really for someone like me?”
“Why is no one buying from me yet?”
“Why do I feel like I’m failing?”
To be honest, I’ve asked those questions myself many times— as a founder, a leader, and as someone who’s rebuilt her path more than once. And the truth is: these aren’t just beginner questions, they’re the real-life questions that every leader and entrepreneur face when what’s next is blurry and the pressure is loud.
So let’s talk about them together and shift our thinking from you need all the answers to curiously exploring the questions.
1. “Where do I start?”
Starting anything, whether a business or stepping into leadership, it’s less about the perfect first move and more about your next move.
When I began my business, I thought I had to have everything aligned: a brand, website, launch plan, team the list goes on. What I didn’t realize was I just needed to start. start learning, start designing, start reaching out. I just needed to start.
Shift: You don’t start when everything’s perfect; you start when you’re ready to show up imperfectly and learn. Start with one clear step. Build momentum. Then another.
2. “Is starting a business for someone like me?”
First, let’s strip away the “shoulds.” Business isn’t just for risk‑taking start‑ups or ultra‑confident founders, or the mega wealthy. It’s for the challenged, the restless, and the ones who feel something’s missing.
When I launched, I didn’t have funding, I didn’t have clarity, but I had doubts. Knowing that, I still took a forward anyway.
Shift: Starting is less about being fearless and more about being willing. Willing to adapt. Willing to own the work. willing to learn. And honestly, that’s leadership too.
3. “Why is no one buying from me yet?”
Crickets don’t mean you’re invisible. They mean something’s untested. I’ve seen founders and leaders get stuck here because they skipped authentic connection. The honest reality is, people buy confidence first, and product or service second.
Shift: Pause the hustle. And asses before you spend money on a new subscription or gadget, ask: Who am I talking to? What problem am I solving for them? How will they know I’m the one? Adjust, and then get consistent.
4. “Why do I feel like I’m failing?”
Because you’re learning. Leadership and entrepreneurship share this silent battle: you will always feel like you are breaking in the process of rebuilding. For me, that question came up when I coached leaders and started new ventures. It showed up in quiet ways through overthinking unanswered emails, goals missed, and momentum stall-outs. It’s important to remember this is just a season, and this too shall pass.
Shift: Instead of asking, “Why am I failing?”, ask: “What feedback is here?” Then use that feedback to refine, redirect, and rise.
To this client, I said specifically: You are not failing, you are learning to fly. Give your wings the space to grow.
SOOO.. what next?
The reality is, these questions don’t vanish overnight, and trust me, I so wish they did, but preparing yourself for how to answer them when they do come up can make all the difference in how you shape your experiences. In the meantime, take these three steps:
Pick your one next move.
Chart it.
Hold yourself accountable.
💡 If this resonates with you, I’d love for you to join the conversation. Subscribe down below so you never miss a post.
And if you’re ready to move from questions to clarity — let’s talk coaching.
