Alright – so today we’ve got the honor of introducing you to Carol Ann Conover. We think you’ll enjoy our conversation, we’ve shared it below.

Hi Carol Ann, thanks for joining us today. Are you happier as a business owner? Do you sometimes think about what it would be like to just have a regular job?

Honestly? The last time I thought seriously about a “regular job” was the day I no longer had one.
I never saw it coming. I was so committed to the work, to the members— and the results were consistent, year over year. In 2024, I had exceeded my sponsorship goal by 100%. So when it happened, I was at 89% of a new annual goal and had just raised nearly $5,000 in the week before my last day. The work was working. The people I served knew it. The Board knew it- (the revenue gains, not the firing! LOL). But organizational dynamics don’t always reward performance, and sometimes the people closest to the mission pay the price for someone else’s discomfort with it.

I spent about an hour in shock. Made the call to my Aunt Linda, then my mentor Sherry –and then I got to work.
Something shifted in that hour. I made a decision — not out of desperation, but out of clarity. I was going to lean back into the creative space I had drifted away from and finally live like a creator. The writing, the storytelling, the strategy — all of it on my own terms. No more waiting for someone else to decide what my contribution was worth.
And then the phone started ringing as news circulated. Not the phone in my old office. Mine. Colleagues expressed genuine shock and unending support. It was like I got a giant hug from this community. The people I had worked alongside, the sponsors and venue relationships I had cultivated, the nonprofit leaders and small business owners I had sat with in difficult conversations about visibility and growth — they kept calling me. Not because of a title. Because of trust.

That’s when I understood something I hadn’t been able to articulate before: the value was never the position. It was the relationships. It was the genuine belief I carry that every organization — whether driven by mission or by the dream of a first-generation business owner — deserves to be seen, funded, and celebrated. And my ability to help make that happen doesn’t live in a job description. It lives in how I show up for people.

So no, I don’t think about a regular job anymore. I could not be happier. My entire life and sense of wellbeing has leveled up in ways I didn’t fully anticipate. I lead with the same attitude of service I always have — that part never changed — but now it comes from a place of genuine freedom rather than obligation. I feel healthier. More myself. And more effective because of it.
Because I’ve learned that when you lead with service and you do the work with your whole heart, people find you. And there is no greater freedom than building something where your livelihood is protected by the depth of the impact you make — not by someone else’s comfort level with how well you do it.

Carol Ann, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I didn’t set out to be a strategist. I set out to be of service.

That’s not a reframe — it’s just the truth. Caring for others has been part of my life for as long as I can remember. Growing up with a younger sister and brother, and a whole crew of little cousins, meant that looking out for someone smaller or newer to the world was just Tuesday. In high school I babysat to save up for my first car. Service wasn’t a value I developed. It was just how life worked in my world from the very beginning.

Writing was always there too — quietly, persistently, from the very beginning. I was an avid reader who kept diaries and journals, and who would absolutely write a strongly worded letter on my grandmother’s behalf if some company had the nerve to upset her. I had a gift for putting words together and I knew it. What I didn’t know — and I’ll own this with a laugh — is that writing could be a career. It genuinely didn’t occur to me. I majored in math. I was often a little rudderless navigating early adulthood, without a paved road connecting me to the thing I was most naturally built for. Writing was always present, but for a long time it lived in the margins of my life rather than at the center where it belonged.

It started in a hospital in New Jersey at nineteen years old. I didn’t know it then, but those years in healthcare — surrounded by patients navigating some of the hardest moments of their lives — were quietly shaping everything that came after. The work taught me what actually matters. And the women who worked those floors with me, Janine, Lois, Trudy, Esteley, took a young woman with a difficult home life and some generational wounds she was still figuring out, and they big-sistered her through it. Here’s looking at you, J-9. I will never stop being grateful.

From there I moved into a private medical practice, where an early test of integrity handed me my first real management role before I was ready — or thought I was. Those seasoned nurses could have eaten me alive. Instead they mentored me. That pattern — of showing up honestly in hard moments and being met with grace — has repeated itself throughout my life in ways I still find humbling.

Eventually, I followed a pull toward something warmer. With some distance from family drama and a bad breakup calling my name, I moved to Fort Lauderdale. My strategy for learning a new place has always been the same: go into hospitality. There is no faster, more honest way to learn a community and its people. I worked at Yesterday’s, and then landed a brief stretch at a telecom company — the kind of corporate environment where the culture was fine but the heart was missing, and I knew from the moment I arrived that it wasn’t where I was meant to stay. But something extraordinary happened there that I would never trade. A rep from a client whose office was in the same building came in to discuss her bill on my very first day, and we went to lunch. We have been going to lunch ever since. Her name is Christina, and she is my best friend — my Forever Friend. We call it our Forever Lunch, and it started the moment a professional relationship quietly announced that it had no intention of staying professional. That has been one of the defining themes of my life. The people I meet across a counter, across a table, across a room — I keep them. And they keep me.

I left that corporate chapter behind in the autumn of 2003 and landed at the Village Grille in Lauderdale-by-the-Sea, where I found my people all over again. We’ve scattered across states since then, but that crew is still very much a loving, connected family. That’s what happens when you show up for each other. You don’t lose those people.

The writing was finding its footing in Florida too. I started contributing to By The Sea Times, run by the wonderful John and Eva MacMillan, then connected with WeMerge Magazine — a genuinely cool, art-centered glossy — and picked up some business features in Go Riverwalk Magazine, which reached a higher-end readership in the Las Olas corridor of downtown Fort Lauderdale. I was researching, submitting, building. And then one evening working at Shuck N Dive, I glanced down at a credit card and recognized the name of one of the publishers of the Beachfront News. I introduced myself, told him I had enjoyed a particularly bold cultural piece he had recently run — the kind of writing that takes confidence to publish and even more confidence to discuss over appetizers in South Florida. He asked me to send him something. I told him I already had. I gave him a quick overview on the spot, and just like that I was writing for the Beachfront News — which later became the South Florida Chronicle — and managing their ad sales. That moment taught me something I have never forgotten: opportunity lives in paying attention. And in having the nerve to speak up when you do.

By 2003 I had started building Prowrite, a freelance writing and content practice that became the quiet throughline of everything that followed — ghostwriting, copywriting, branding, grant writing, technical writing. The work that had lived in my journals and strongly worded letters for my grandmother finally had a professional home. Writing was no longer in the margins. It was the work. My first client was an office equipment consultant who hired me to write a technical patent for an ingenious idea — one that would harness emerging WiFi and VoIP technology to transform tourism advertising. It was a fascinating first assignment and a signal of the range this work would eventually take. And as my experience deepened and culminated across healthcare, hospitality, nonprofit leadership, chamber work, and community service, Prowrite grew up right alongside it — eventually evolving into CA Strategies Consulting, the full expression of every chapter that came before it.

When I eventually made my way back to the Northeast, I did what I always do — went into hospitality first. I landed at Davidson Brothers, a beloved local brew pub, and started learning the territory the way I always have: through people and conversation. I had originally planned to move to Tennessee, but the Adirondack region had other ideas. I stayed, revived Prowrite, and spent a year doing social media and marketing for small businesses before a chance encounter at a food event with a friend led me to the new ownership team of the Queensbury Hotel — a stunning boutique property built in 1926, right in the heart of the city I now call home. That conversation led to a role helping launch their new fine-dining restaurant, and that experience opened the door to a mentor who, as a customer, saw something in me and brought me into the chamber of commerce world.

I joined that role during the pandemic — when nobody knew where hospitality, events, or community engagement were headed — and I stayed for five years. I produced 50+ events annually, founded a Veterans Business Network, took over as liaison to the Women’s Business Council programming and doubled engagement, and ultimately exceeded my sponsorship goal by 100% in 2024, contributing over $130,000 in member retention, new revenue, and event fees. Along the way I also served on the boards of the Lower Adirondack Regional Arts Council, Crandall Public Library, Southern Adirondack Independent Living, and Soroptimist International of the Adirondacks — because mission-driven community work has never been separate from the job for me. It has always just been life.

Today, CA Strategies Consulting is the full expression of everything those chapters built. I work with nonprofits, chambers, small businesses, and mission-driven organizations on content strategy, fundraising support, event elevation, brand voice, and the kind of relationship-building that actually moves the needle. I’m also an AI implementation consultant — helping purpose-driven organizations understand how to use emerging tools without losing the human voice that makes their work matter. That’s the piece most technical consultants can’t offer. The voice layer is everything.

But the consulting practice is only part of the picture. In May of 2025, at the encouragement of my financial advisor, the incomparable Sherry Finkel Murphy of Madrina Molly, after a particularly insulting fifty-cent raise, I launched memyselfandwine.com — a food and wine lifestyle platform that draws on years of writing about food for the now-defunct Examiner.com and several of the publications I contributed to over the years. Food and wine have always been a genuine passion, and her advice was simple and smart: build it now as a sideline, monetize it, and it will be there when you need it. When I was let go on August 1st, I had to shift focus to building CA Strategies’ client base first — but I am actively sparking it back to life now, and the content is flowing, plus I’m making regular contributions to the Glens Falls and Saratoga Business Journals to keep connected to the business community. It keeps my network thriving and continues to cultivate multiple streams of opportunity.

What carried me through those early weeks of unexpected unemployment was a decision I made deliberately and out loud: I was going to live as a writer. Not someday. Now. I shaped my daily life to reflect that intention — writing every morning, treating creativity as the work rather than the reward at the end of it. That decision was informed in part by Martha Beck’s *Beyond Anxiety*, which explores the link between right-brain creative engagement and the relief of anxiety. Beck references the experience of a neuroscientist who suffered a stroke in her left hemisphere and noticed, almost immediately, the absence of the crippling anxiety she had carried for years. As she relearned speech and rebuilt her life leaning into her right brain, she found that it didn’t just restore her — it actually improved her scientific thinking. That idea landed hard for me. Creativity wasn’t the indulgence I had been treating it as. It was the medicine. And I was done rationing it.

What sets me apart is not a methodology. It’s an orientation. I lead with service, I build relationships I keep for life, and I believe with my whole heart that every organization with a mission deserves to be seen, funded, and celebrated. The numbers reflect that. But so do the phone calls I still get from people who aren’t calling the chamber — they’re calling me.

That’s the work. That’s the whole thing, really.

Can you share a story from your journey that illustrates your resilience?

The day I was let go, I spent about an hour in shock. And then I picked up the phone.

Not to job search. Not to vent. I launched a personal calling campaign to reach out to every sponsor, every partner, every community member I had worked alongside — to thank them. Genuinely, personally, without agenda. I had been at 89% of my annual sponsorship goal and had raised nearly $5,000 in the week prior. The results were there. The relationships were real. I wanted the people behind those relationships to know that regardless of what had just happened, they had mattered to me and that working alongside them had been a privilege.

What happened next stopped me in my tracks.
The responses I got were not polite. They were not obligatory. They were shock. Dismay. And an outpouring of support that I was not fully prepared for. People were upset on my behalf. They wanted to know how they could help. They told me, in no uncertain terms, that I was the relationship — not the organization. That the value I had brought to their sponsorships, their events, their visibility in the community lived in me, not in a job title.

I heard that, and something clicked into place.
Within two months of that phone call campaign, I had written and published Condition: Human — a poetry collection born directly from that moment of clarity and loss and forward motion all tangled together. It is available on Amazon, Barnes & Noble, and other online outlets, with links at carolannconover.com/books. Writing it was not therapy. It was declaration. I was done waiting for permission to live as a creator.

That calling campaign also became the foundation of CA Strategies Consulting. The sponsors who called me back, the nonprofit leaders who said “whatever you’re doing next, I want in” — they were not just being kind. They were telling me where the work actually lived. And I listened.

Resilience, for me, has never looked like pushing through alone. It looks like leaning into every genuine connection you have ever made and trusting that if you showed up for people the right way, they will show up for you. That campaign proved it. Those calls are still coming.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

I had to unlearn the belief that excellent work is always enough protection.
For most of my career, that equation had held. Show up. Deliver results. Lead with service. Build trust. Repeat. And for a long time, in most rooms, that formula worked exactly as advertised. So I kept applying it — even in an environment where the social architecture had been established long before I arrived.
When I joined the chamber, there were two other staff members who had worked together closely for years and shared a genuine friendship. They were a unit — and that was fine. I wasn’t looking to insert myself into something that wasn’t mine. I put my head down, focused on the members, and let the work speak. And speak it did. Year over year, consistent results. Deep relationships across the membership. A reputation built on showing up and following through.
When my mentor announced his retirement, I believed in my colleague enough to encourage her to step into the leadership role. I wrote her letter of intent. I coached her through her uncertainty. I told her we were surrounded by people who could help her grow into every part of the job. I meant every word of it.
What I didn’t fully reckon with was that the social dynamic that had defined that office from the beginning didn’t disappear when the org chart changed — it calcified. And the esteem I had earned among the membership, the self-advocacy I practiced, the space I took up simply by doing good work — those things, it turned out, were not comfortable for everyone.
When the end came, it came without warning. And in the clarity that follows a shock like that, I saw the full picture for the first time.
The lesson I had to unlearn was this: security is not the same as safety. I had clung to the stability of a role I was genuinely good at, told myself that performance was its own protection, and ignored the signals that told me otherwise. Real security, I now know, doesn’t live in a job. It lives in your relationships, your reputation, and your willingness to recognize your own worth — not just in the work you produce, but in the environment you choose to produce it in.
I will never again mistake a paycheck for belonging. And I will never again advocate less for myself than I would for a client.
That shift — from security-seeker to self-directed — is the foundation everything I’m building now is standing on. I’m my own captain, my own navigator and my own first mate.

Contact Info:

• Website: https://www.carolannconover.com
• Instagram: @ca_strategies
• Facebook: https://www.facebook.com/profile.php?id=61582562702879
• Linkedin: www.linkedin.com/in/ carol-ann-conover-5a689a8
• Yelp: https://www.yelp.com/biz/ca-strategies-consulting-glens-falls
• Other: Me Myself & Wine Info: www.memyselfandwine.com & @followmemyselfandwine

Image Credits

Carol Ann Conover
CA Strategies Consulting
MeMyselfandWine.com