Today we’d like to introduce you to Chealsea Wierbonski

Hi Chealsea, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.

My journey to becoming a Writer, Keynote Speaker, and Coach has been a long one that includes a lengthy career in tech and a lot of inner growth and personal transformation.

I grew up in a small town in West Virginia and graduated from West Virginia University in 1995. At that time, tech hadn’t fully permeated into the main stream. The Internet hadn’t really taken off yet and having a computer in the home just wasn’t a common thing, especially in West Virginia, where many people live modest lives, especially then. So when I graduated from WVU, all I knew was that I wanted to leave the state to pursue a different life in a place where there was more opportunity. I had my heart set on a career in social justice or environmentalism, and so I moved to California. But I wanted to take a year off before I started working, so I moved to a ski resort town in Tahoe first to snowboard and work at ski resorts.

While I was there, I met someone whose father was an executive in a software company in Silicon Valley called Network General. After my first year at the ski resort, I got to know this person’s family pretty well and the father offered me an internship at Network General, I believe, sensing my ambition and desire for personal growth and change. I had never even considered a career in tech because I just didn’t know anything at all about this world, but I couldn’t pass up the opportunity for such a great job. I moved from Tahoe to Santa Cruz so that I could easily commute to Palo Alto.

On my first day of my internship, I was overwhelmed–both by the idea of having to learn technology with absolutely no exposure to it whatsoever, but also by the lifestyle that people there lived, as well as the way they all carried themselves. These were well educated, high achieving, successful people and the whole world just seemed different from my life experience to date. They all drove such nice cars, and talked about their extravagant vacations to Hawaii or Japan. They had hobbies like photography and racing, or my favorite, getting their pilot’s license. I just had never experienced anything like it.

The one thing I did know though, was that this internship was an excellent opportunity, so I used it to learn as much as I possibly could, and I worked as hard as I could to demonstrate my willingness and ambition. I worked with some very kind people. I was only 23 and I’m sure I seemed naïve; many people helped me, especially a mentor I had named Shih-Wei who taught me everything he knew about technology. I spent the summer with Shih-Wei understanding the inner workings of tech. Back then, nothing was plug and play so you really had to know your stuff to even get connected to the Internet through a dial up modem.

At the end of my internship, I was offered a full-time job as a technical writer and my career in tech began.

During those first few years, I told myself that working in tech was only temporary, but the more that time went on, the more I got comfortable with the paycheck, the health insurance, and other perks. Because I came from so much economic instability and an area rife with poverty, the security of my career felt really good to me. It seemed foolish to give up and nothing that I wanted to do that felt good in my soul guaranteed that kind of money. Since I couldn’t rely on anyone to help me if I hit any sort of financial hardship, I felt like I “had to” stay in tech.

As I got over the newness of those first two years, my feelings of being different from everyone were really amplified, and this became even more pronounced when I moved to New York City in 1999. It’s much more social in NYC than in Silicon Valley, and after work drinks with co-workers happened nearly every week, where I often heard about the privileged backgrounds of my co-workers. It became evident as I got to know people, that I came from a very different place.

My father was a coal miner, so was my grandfather and great grandfather, who immigrated to the US from Poland. No one in my family had gone to college. I wasn’t ashamed of my background, but I knew it was different from others, so I didn’t feel like I could share anything about me. I just didn’t want my co-workers and friends to see me differently. This caused me to create a distinct boundary between my work self and outside of work self, which actually led to a feeling of not being able to show up in an authentic way at work. I felt like I had to hide parts of myself and put on a persona in order to fit in and the whole thing made me feel uncomfortable and insecure.

I noticed that I would feel resentment on my walks home after our after work drinks. And I would feel really bad for feeling this way, because they were all so nice to me. To them, I’m sure I looked just like anyone else and honestly, they probably would have been totally accepting of my background, but I didn’t see it that way at the time, and I just wasn’t equipped yet to navigate my feelings.

I continued to work really hard and had a deep desire to make more money, but I distinctly remember feeling like I was lucky to have what I had and that anything more just wasn’t possible for “people like me”. So between the feelings of resentment toward my co-workers, and the feeling that I couldn’t bring my authentic self to work, combined with my lack of self-worth, I felt alienated. This alienation had many repercussions and held me back in my career for many years. I was easily triggered and often felt defensive when I’d talk to people, which impacted my ability to build a network and advocacy for my work. In hindsight, I now know that one of the biggest factors in not getting ahead was my self-doubt, negative mindset and limiting beliefs, but of course, I had no understanding or awareness of this at the time.

Even though I worked incredibly hard, got an amazing amount of work done, could basically learn anything and learn it fast, I remained a technical writer, stuck at the same level, for about 10 years. I was feeling stagnant and I started to self-sooth in unhealthy ways–eating, drinking, and going out a lot. Finally after a period of burning the candle from both ends–extreme overworking, combined with a relentless after work social life, I was exhausted. I took a year off to think about whether I wanted to continue my career in tech. I briefly dabbled in other areas like writing and fashion, but nothing provided the kind of financial security that tech did.

That year off was really good for me though. It’s one of the first times that I can remember trying to work on myself. I tried to take Pilates, go to therapy, stopped drinking, and started acupuncture for my anxiety. None of it (except the acupuncture) stuck. But the important thing is that my mindset had shifted a bit–from feeling totally hamstrung and stuck to feeling like maybe there was a way to change things. When I went back to my old job as a tech writer at the same company, I noticed that I had a little more self confidence, which I attribute getting more comfortable with myself during that year off.

Over the next year I started to really desire career advancement. I had been a tech writer for over a decade and was starting to feel restless. I wanted more excitement and more impact. That’s when I set my sight on product management. All of the product managers at my company seemed to possess a confidence that I just didn’t have. I had no idea how I’d do it, but I looked at all of them and said, I know I’m at least as smart as they are. So if they can do it, I probably can too.

At that point, everything started to fall into place–with just that one mindset shift. It was slow going at first, but that shift was really pivotal in terms of altering my career trajectory. Once I took that step to move into product management, and then started to work at Google, I was faced with all sorts of challenges that forced me to grow.

The further I got in my career, the more the beliefs I had about myself and the world were challenged. There were so many times when I felt uncomfortable, or I felt discouraged, but I held strong to the idea that I needed to master my mindset in order to progress.

For example, I had to do a lot of work to overcome my fear of speaking in public, both in large meetings as well as on a stage at events. I had to learn how to interface with people who were much more senior than I without feeling intimidated. I had to learn how to express my ideas, advocate for them in open forums, and build buy-in in order to be perceived as a thought leader. I had to learn how to acknowledge that I actually had skills, and value to bring to a team in order to overcome impostor syndrome. With each of these challenges, I slowly shifted my limiting beliefs and built my authentic confidence. I finally overcame my self-doubt.

The longer I went through this process, the easier it got in some ways, because I knew what to do. The emotional aspect of it remained challenging, but at least I felt I had the tools I needed to work through these things because I had been developing them over this second 10 year period of my career. During this time is when I developed my framework that I’m now teaching in my courses and coaching practice. I also talk through this same framework when I do public speaking.

It’s interesting because most people think that in order to thrive in their careers and grow as leaders, there needs to be an emphasis on developing outer skills and tactics, like negotiation skills, strategic thinking, networking etc; and while these things have their place, the real transformation happens when you do inner work. So this framework I developed helps with overcoming self-doubt and limiting beliefs in order to thrive and rise to leadership, without overworking or doing any of the external activities that we typically associate with career advancement, like networking or pursuing certificates. It’s truly meant to help people align their careers more closely with their deep inner ambition.

Success really has nothing to do with how many hours you log, how much work you take on, or any of the other external things we sometimes think are important, and everything to do with how you think about yourself and your abilities. If you think you’re capable of being a leader, capable of amazing things, then others will think that too.

As I refined this framework over the years and felt more and more successful, there came a point around my 50th birthday where I felt I was ready for more. I wanted to help other people who may be facing similar challenges and struggles that I did. I decided to formalize my framework and make it available through coaching, digital courses and public speaking with the hopes of helping people to overcome their self-doubt to thrive in their careers without overworking. And this is how I came to embark on this next phase of my career as a Writer, Keynote Speaker, and Coach.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?

It definitely has not been a smooth road; I think I mentioned a lot of these in the previous answer. But the most difficult part of my entire journey was not giving up when things got difficult. I felt very bad about myself for a long time and had so much anxiety around work and performance. But at the same time, I had a strong desire for a better life and I’m a very driven person. So even though things felt bad or got very difficult at times, I forced myself to keep going. I used to remind myself that I didn’t want to let myself down; that I wanted something different, something better. And all I had to do was to figure out how to push through. I’d try to imagine what life would be like on the “other side”, once I got through the challenge. What would my job look like? What kind of opportunities would be available to me? How differently would I feel about myself. That sort of thing. But there were plenty of times where I felt, “wow maybe this just isn’t for me”, or “maybe I don’t have what it takes”, or “maybe I should just go back to being a tech writer”. I think it’s increcibly important for people, when you really, really want something, to just keep going. Because what I learned wast that each time I navigated one of these difficult situations, it resulted in a lot of internal growth, and progress on the other side.

As you know, we’re big fans of Confident, Healthy Leadership for Women by Chealsea W. For our readers who might not be as familiar what can you tell them about the brand?

I’m a Writer, Keynote Speaker, and Coach who helps high-achieving professionals transform their inner confidence so that they can thrive in their careers without endless hustle. Drawing from my own journey, I help women to overcome self-doubt, impostor syndrome, develop authentic leadership presence, and achieve success on their own terms—in their careers and beyond.

I’m known for my empathetic, authentic and relatable style because I draw from my own experiences and insights that come from my journey as a first-generation college graduate in Appalachia to a product leader at Google in NYC. Although I refer to my working class upbringing as the main driver of my ambition and refer to my own journey from self-doubt to success, I’ve been told that people from many different backgrounds are able to relate to what I have to say. I seem to appeal to anyone who has ever felt like an outsider or “less than” the social group that they’re part of.

The framework that I have developed and now teach is truly transformational because the core principle is to focus on mindset shifting and addressing inner confidence, rather than taking external actions. When my clients focus on transformation through inner work, the impact is felt throughout many dimensions of their lives and they see change beyond just their careers.

My mission is to equip my clients with the tools, mindset, and unwavering confidence they need to see tangible results. I’m helping them to truly step into their power as leaders—whether that’s to secure a promotion to a higher leadership role, achieve a significant salary increase, confidently negotiate and close a major deal, or just to deliver a compelling presentation at an industry conference or company-wide event. At the end of our time together they feel empowered and able to boldly pursue their highest career ambitions.

Finally, I believe that my style is practical while still being inspiring: I balance actionable strategies with motivation to drive real change in all of the ways that I’ve mentioned above. I value genuine transformation over quick fixes, and I’m passionate about helping women achieve the kind of breakthrough that I experienced in my own career.

What was your favorite childhood memory?

In my writing and talks, I focus a lot on the ways in which my upbringing in West Virginia impacted my identity as an adult, I explore the challenges that I had once I left there and landed in a new environment around people who were different from me, so this could make it seem like I view my childhood and upbringing a something negative, which isn’t necessarily the case. There were times when I was very young, like maybe 6 or 7, where my memories of growing up in West Virginia are very sweet.

In one of our first houses, we lived in a very rural area. Our house was on a significant amount of land, with woods right in our back yard. This was in the early 80’s, back when it was totally acceptable to run around all day by yourself as a kid.

My brother and I would play in the woods with the other kids in the neighborhood and we’d be gone for hours, exploring the woods and going on adventures, climbing trees and building forts. Sometimes just my brother and I would run off together and we had such wild, vivid imaginations. Those woods turned into something magical for us, where we could escape the chaos of our home and find comfort in our own little world. To play freely in an open, wild area like that really allowed us to be creative and free in a way that I believe has had a profound effect on both of us as adults in terms of developing our creativity and the ability to express ourselves.

Pricing:

• I offer many different packages for coaching, but the most common is a 3-month weekly commitment for $2700
• My flagship leadership program, which includes 7 modules of digital course content as well as a 3-month bi-weekly group coaching program is $2500
• I also offer a career boosting video masterclass where I share my 5 step framework to overcome impostor syndrome; this is $197

Contact Info:

• Website: https://www.chealseaw.com
• Instagram: https://instagram.com/chealsea_w_
• LinkedIn: https://www.linkedin.com/in/chealsea/
• Other: https://www.tiktok.com/@chealsea_w_

Image Credits

Masha Lou Photography, Tre Dasher