We recently connected with Jackie Carroll and have shared our conversation below.

Jackie , looking forward to hearing all of your stories today. Can you tell us a story about a time you failed?

One of my biggest professional failures was setting up a VR startup. I truly believed in the concept, poured everything into it, and even secured initial funding. But when it came time for the second round, we just couldn’t get the backing we needed. It was a devastating blow. I felt like I had let myself, my team, and my investors down, and for a while, I struggled with the weight of that failure.

At first, I saw it purely as a loss. But with time and reflection, I realized that experience gave me an incredible education in resilience, business strategy, and the importance of adaptability. More importantly, it shaped how I coach others today—because I know firsthand that failure isn’t the end; it’s often just a pivot point. That setback led me to a path that aligned far more with my purpose—coaching, helping others navigate their professional challenges, and ultimately creating a more fulfilling career for myself.

So yes, I failed. But that failure also led me here today, and I wouldn’t change that for anything.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I’m Jackie Carroll, a career, mental health, and well-being coach dedicated to helping professionals break through career stagnation, find fulfillment, and build resilience in their work and lives. My path to coaching has been anything but conventional—I’ve worked across multiple industries, from film production to corporate leadership as an executive assistant, bought and ran a 5-star destination spa, helped my husband establish his business, and even launched a VR startup.

One of the pivotal moments in my career was being promoted from Executive Assistant to Team Lead, where I managed a large team of Personal Assistants and administrators at PwC. This transition taught me the power of leadership and mentorship and the importance of fostering high-performing teams. It also reinforced my passion for coaching—helping professionals navigate career growth, workplace challenges, and personal development. That passion ultimately led me to pursue coaching, where I now help others gain clarity and confidence in their own careers.

Through my coaching practice, I offer Workshops and group Coaching on topics like imposter syndrome, personal branding, and workplace challenges, designed to help clients gain clarity and take action.
Speaking & Thought Leadership: As an advocate for career well-being, I share insights through written content, podcasts, and speaking engagements.
YouTube Channel – ‘Coaching Corners with Jackie Carroll’: Weekly content on career transitions, workplace fulfillment, and personal branding to build a community of 100,000+ engaged professionals.

I help clients who feel stuck, overwhelmed, or unfulfilled in their careers gain clarity and confidence, develop actionable career strategies, and create a life aligned with their values and strengths.

What Sets Me Apart? I don’t just coach from theory—I coach from lived experience. I’ve been where my clients are:

I’ve faced career transitions head-on, moving from an Executive Assistant to a Team Lead, where I had to redefine my role, step into leadership, and support a high-performing team. I understand the challenges of taking that next career leap and navigating imposter syndrome, leadership expectations, and workplace politics.

I’ve experienced business failure firsthand, having launched a VR startup that ultimately failed. That failure taught me more about resilience, strategic thinking, and reinvention than any success ever could. I use those insights to help my clients turn setbacks into growth opportunities.

I’ve built businesses and shifted industries multiple times, and I understand the emotional and practical challenges of reinventing your career. My coaching is action-driven, results-focused, and deeply empathetic—I don’t just give advice; I guide my clients through real, lasting transformation.

What I’m Most Proud Of – Successfully transitioning from an Executive Assistant to a leadership role and using that experience to help others advance their careers. Taking the lessons from my failed startup and turning them into a thriving coaching business that helps others navigate uncertainty. Building a coaching practice that has helped countless professionals redefine success on their own terms. Creating a space where clients feel seen, heard, and supported in their career and personal development journeys.

What I Want People to Know About My Work – If you feel unfulfilled in your career, stuck in indecision, or unsure of your next step, you’re not alone. I’m here to help you get unstuck, regain control, and confidently move forward. Career success isn’t about climbing a ladder—it’s about building a career that truly aligns with who you are. My work is designed to help you do just that.

What’s a lesson you had to unlearn and what’s the backstory?

The Lesson I Had to Unlearn: Success Doesn’t Mean Doing It Alone
For much of my career and entrepreneurial journey, I believed that success meant figuring things out on my own—that asking for help was a sign of weakness and that the strongest, most capable people were the ones who could handle everything themselves.

This mindset was deeply ingrained in me, and at times, it served me well. It pushed me to be resourceful, resilient, and independent. However, over time, I realized that this belief was holding me back rather than moving me forward.

The Backstory: When Doing It Alone Led to Burnout
One of the biggest moments that forced me to confront this was the failure of my VR startup. In the early days, I poured everything into the business—I worked around the clock, tried to handle too many roles at once, and believed that if I just worked harder, I could make it succeed.

I didn’t lean on a strong enough support network. I didn’t reach out for mentorship or guidance as much as I should have. And when things started going wrong—when funding didn’t come through, and we faced roadblocks—I internalized it as my failure alone.

The startup ultimately didn’t survive, and while the experience was incredibly valuable, the biggest lesson wasn’t about business strategy—it was about mindset. I had to unlearn the idea that success is a solo pursuit and start embracing the power of collaboration, mentorship, and seeking help when needed.

The Shift: Learning to Lean on Others
Later, when I transitioned into the corporate world and was promoted from Executive Assistant to Team Lead, I faced a similar challenge in a different form. I was now leading a team of PAs and administrators at PwC, and the old mindset crept back in—I felt like I had to have all the answers, that I couldn’t show uncertainty, and that I had to prove myself constantly.

But leadership—and success—don’t work that way. I had to learn that the best leaders aren’t the ones who have all the answers; they’re the ones who empower their teams, ask for input, and create an environment of collaboration and trust.

This realization completely changed how I approach my work today as a career and well-being coach. I emphasize this with my clients—whether they’re navigating a career transition, struggling with imposter syndrome, or building their businesses. You don’t have to do it alone. Asking for help isn’t a weakness; it’s a strategy.

The Takeaway
True success isn’t about going it alone—it’s about knowing when to ask for help, collaborate, and lean on others.
Burnout isn’t proof of strength—it signals that something needs to change.
The best leaders and entrepreneurs don’t have all the answers, but they surround themselves with the right people who help them figure it out.

It took me failing, burning out, and rebuilding to unlearn this lesson, but it has shaped everything I do today.

Any advice for managing a team?

How to Manage a Team & Keep Morale High (Without Losing Your Mind)
Let’s be real—leading a team isn’t just about hitting targets and getting stuff done. It’s about people. And if your team is burned out, disengaged, or just going through the motions, no amount of “rah-rah” speeches will fix it. High morale isn’t about free snacks or casual Fridays—it’s about how people feel about their work, their leader, and their team.

I learned this firsthand when I transitioned from Executive Assistant to Team Lead. It was a huge shift—from supporting leadership to actually being leadership. At first, I thought I had to have all the answers, be in control of everything, and somehow keep everyone happy. Spoiler alert: That’s not how it works.

What actually works? Here’s what I learned about leading a team without micromanaging, burning out, or accidentally killing morale.

1. Be Real With Your Team
Nobody wants to work for a robot. Be transparent, be human, and be honest.

If there’s a challenge, share it. Your team doesn’t expect perfection—they expect clarity.
If something’s going great, shout it from the rooftops.
If you don’t have the answer, say so—and then involve your team in finding the solution.
Teams work best when they trust their leader, and trust comes from honesty, not pretending to have it all together.

2. Celebrate the Small Wins (Not Just the Big Ones)
Big achievements are great, but let’s be honest—they don’t happen every day. People need to feel valued in the day-to-day, not just during performance reviews.

Instead of a generic “great job,” call out specific wins:
“I loved how you handled that difficult client call—it turned the situation around completely.”
Public recognition goes a long way. A quick shoutout in a team meeting or Slack message can boost morale instantly.
When people feel seen, they stay engaged, motivated, and actually want to do their best work.

3. Trust Your Team (AKA Stop Micromanaging)
No one likes a leader who hovers over every decision. Give your team space to own their work.

Instead of saying, “Do this exactly like I would,” try, “How do you think we should approach this?”
Let them come to you with solutions, not just problems.
Trust is a two-way street. If you trust your team, they’ll trust you—and that’s when the real magic happens.

4. Actually Listen (Not Just Nod Along)
You know that feeling when someone is “listening” but clearly just waiting for their turn to talk? Yeah, don’t be that leader.

Schedule regular check-ins and make them about more than just tasks. Ask things like:
“How’s your workload?”
“What’s frustrating you right now?”
“What’s something you’d love to work on?”
When someone gives feedback, act on it (or at least acknowledge it). Nothing kills morale faster than people feeling like their input doesn’t matter.
When people feel heard, they feel valued. And valued employees are engaged employees.

5. Lead by Example—Your Energy Sets the Tone
If you show up stressed, overwhelmed, and constantly putting out fires, guess what? Your team will start doing the same.

Stay solution-focused, not problem-obsessed.
Keep the mood positive but real—don’t fake enthusiasm, but also don’t bring doom-and-gloom energy into every meeting.
If morale is low, acknowledge it and get the team involved in brainstorming ways to turn things around.
A leader’s energy trickles down—so make sure you’re setting the right tone.

6. Help Your Team Grow
People don’t just want a job—they want a career. If they don’t see room to grow, they’ll start checking out (or checking LinkedIn for other opportunities).

Ask about their goals and help them get there.
Share opportunities for learning, mentorship, and upskilling.
Give them new challenges and trust them to rise to them.
When people see a future where they are, they stay engaged, motivated, and committed.

7. Build a Team That Feels Like a Team
We spend way too much time at work to not enjoy the people we work with.

Encourage collaboration and connection.
Create space for people to bond outside of tasks—whether it’s a team lunch, a quick coffee chat, or a Slack channel full of memes.
Don’t underestimate the power of laughter and camaraderie—when people enjoy who they work with, they show up differently.
Final Thought: People First, Results Second
If there’s one thing I’ve learned, it’s this: People who feel valued, trusted, and supported will always outperform those who feel micromanaged and overlooked.

Being a great leader isn’t about having all the answers—it’s about empowering the people around you to find them.

And the best part? When you build a team that feels seen, heard, and motivated, they won’t just work harder—they’ll actually enjoy doing it.

So, if you’re leading a team, ask yourself this: Are you creating an environment where people can do their best work? If not, now’s the time to start.

Contact Info:

• Website: https://www.jackiecarrollcoaching.com/
• Instagram: https://www.instagram.com/jackiecarrollcoaching/
• Linkedin: https://www.linkedin.com/in/jaccarroll
• Youtube: https://www.youtube.com/@CoachingCorners