Story & Lesson Highlights with Cheryl Sutherland of Los Angeles

We recently had the chance to connect with Cheryl Sutherland and have shared our conversation below.

Hi Cheryl, thank you so much for joining us today. We’re thrilled to learn more about your journey, values and what you are currently working on. Let’s start with an ice breaker: Are you walking a path—or wandering?
I feel like I’m taking a little meander. I like walking down a path, seeing if it works for me, maybe doubling back and trying door number two, or three, or four. The fun thing is they all will lead to the same destination, I just get to play a little and do side quests along the way.

Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Cheryl Sutherland, a speaker, workshop facilitator, and coach focused on helping people reconnect with themselves, build confidence, and move forward with clarity. My work centers on creating intentional spaces where people can slow down, get honest, and make aligned decisions about their lives and work. I don’t believe in surface-level personal growth or telling people what they should do. I help them hear themselves again and trust what they already know.

PleaseNotes came later as a natural extension of this work. After years of speaking and facilitating workshops, I noticed that people would leave feeling clear and inspired, but struggle to sustain that momentum once real life kicked back in. PleaseNotes was created to make personal growth more consistent and accessible through guided journals, planners, and affirmation practices. Right now, I’m focused on expanding my speaking and workshop work, while continuing to grow PleaseNotes as a supportive companion to the deeper inner work I do with individuals and organizations.

What makes my work a little different is that I’m not afraid to get into the nitty gritty. Alongside confidence and clarity, I facilitate deeper conversations around inclusion, DEI, and allyship, the kind of work that requires self-awareness, accountability, and real reflection. Fun fact, I’ve lived in three different countries, and I also always choose an aisle seat when I fly.

Okay, so here’s a deep one: What breaks the bonds between people—and what restores them?
Honestly, I think what breaks the bond between people most often isn’t conflict, it’s what goes unsaid. It’s the assumptions we make, the feelings we swallow to avoid discomfort, and the moments where we stop communicating clearly because we don’t want to rock the boat. Over time, that silence turns into distance, resentment, or misunderstanding, even between people who care about each other.

What brings people back together is honest, human communication. Not perfectly worded conversations, just real ones. When people take the time to understand what they’re actually feeling, say it out loud, and listen without immediately getting defensive, something shifts. Repair becomes possible. I’ve seen over and over again that when people feel safe enough to be honest and feel heard, connection can be rebuilt, whether that’s in relationships, workplaces, or communities.

What fear has held you back the most in your life?
Definitely the fear of judgment and being disliked. Growing up, there were abusive situations I was put into and I learned very early that being liked meant survival. I became incredibly aware of other people’s emotions, watching for shifts in tone, mood, or energy, and I learned how to shape myself to keep the peace. For a long time, I was different versions of myself depending on who I was with.

Things began to change when I left my hometown. Creating physical distance gave me the space to let go of that role and start building a version of myself that felt more honest and grounded. It wasn’t instant, but it was the first time I realized I didn’t have to earn safety by disappearing or performing.

That fear still shows up in my work, especially as an entrepreneur. When you’re putting ideas, products, or services into the world, it’s personal. If people don’t resonate with what you’re offering, it can feel like rejection, even when it’s not. What’s helped me move through that fear is learning to separate my worth from other people’s reactions and trusting that the right people will find their way to the work. That shift has been freeing, both personally and professionally.

I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. What’s a belief you used to hold tightly but now think was naive or wrong?
That doing things the “right way” was the way to success. I followed rules closely, waited for permission, and assumed that if something wasn’t a perfect fit on paper, it wasn’t meant for me. Looking back, that belief was quietly limiting how many opportunities I even allowed myself to consider.

That showed up in really practical ways. I didn’t apply for grants unless my business matched every requirement exactly. I passed on applying to sell my products at certain shows because I didn’t think my work fit neatly into the category they were looking for. I also hesitated to pitch myself for rooms or opportunities unless I felt completely qualified, instead of trusting that alignment and lived experience mattered just as much.

What I’ve learned since is that there is no single “right way.” Growth often comes from stretching into spaces you’re not perfectly shaped for yet and letting yourself be seen before everything feels polished. Once I let go of that rigid thinking, more doors opened, not because I changed who I was, but because I finally gave myself permission to try.

Okay, we’ve made it essentially to the end. One last question before you go. Have you ever gotten what you wanted, and found it did not satisfy you?
Funny enough, I’ve noticed a pattern in myself where I reach a goal and almost immediately move on to the next thing. Instead of sitting in satisfaction, I tend to move from pressure and striving to a brief moment of relief, and then right back into pressure again. The goal gets checked off, but the feeling I thought would come with it doesn’t really land.

For a long time, I thought that constant forward motion meant ambition or discipline. What I’ve come to realize is that I wasn’t actually letting myself experience success. I was skipping over pride, joy, and fulfillment and treating achievement like something to get through instead of something to feel. Learning to pause, acknowledge what I’ve built, and let myself stay with the win for a moment has been one of the more meaningful mindset shifts for me, and it’s something I now encourage in my work with others too.

Contact Info:

• Website: https://www.pleasenotes.com
• Instagram: https://www.instagram.com/pleasenotesgoods
• Linkedin: https://www.linkedin.com/in/cherylksutherland