Reinventing Your Career & Embracing Failure: Highlights from My Conversation with Melissa Maher
- Daniel Wathen
- Mar 26
- 4 min read
In a recent episode of Learn Chat Share, I had the odd pleasure of interviewing my longtime friend and executive powerhouse, Melissa Maher. Melissa is the founder and CEO of Pinnacle Enterprises Group, and her wisdom on career growth, leadership, and reinvention is next-level. It was a wonderful way of sharing all the great advice I’ve gotten from her over the years.
This conversation was full of real talk—perfect for anyone navigating layoffs, a career crossroads, or just looking to level up.
Here are some of the top takeaways from our chat:
🔄 1. Reinventing Yourself Mid-Career
Melissa spoke candidly about what it takes to shift gears when you’re 30, 40, 50+ and questioning what’s next.
“If you know your strengths, your values, your quirks—you can build a strong personal brand. That gives you the confidence to go after something new.”
✅ Tip: Take time to define your personal brand. Knowing who you are is the foundation for your next step.
Mid-career shifts can feel daunting, especially when you're used to stability. But change doesn’t mean starting from scratch—it means using your experience in new ways. Melissa emphasized that your personal brand evolves, and so should your ambitions.
🔗 2. Networking Is Everything
75% of people find their next job through their network. According to Melissa, most people wait until they need help to tap into their connections—but the real power comes from building those relationships early and often.
“Expand your network beyond your role, your division—even your industry. That’s where unexpected opportunities live.”
✅ Tip: Think outside your job title. Attend cross-functional meetings. Say yes to mentorship (or better yet—reverse mentorship!).
Melissa reminded us that networking isn’t just about getting something—it’s about giving value too. When you consistently show up in your network, you're top of mind when opportunities arise. Building authentic relationships is a long-term investment that pays off when you least expect it.
Also, staying connected will also allow you to stay infomred on any industry happenings from those that are experiencing it first hand - and is especially important for you when you might not be active in the industry for a time.
💡 3. Failure Is Your Best Teacher
One of my favorite moments from this episode was Melissa’s take on failure. We often treat failure like something to hide, but she reframes it as an essential part of the journey.
“Failure is a powerful teacher. It’s where growth happens. Oprah talks about it. Sarah Blakely talks about it. If you’re not failing, you’re not taking risks.”
✅ Tip: Try writing down your top 10 accomplishments—it’s a great reminder that you’re not defined by your setbacks.
Failure isn’t a sign of weakness—it’s a sign that you're pushing your limits. The people we admire most have failed publicly and often. Melissa encouraged us to view failure as feedback, not defeat.
💬 4. Build Your “Posse”
Career growth can be isolating, especially when you’re in a tough spot. Melissa emphasizes the importance of having a group of trusted people around you who will remind you of your value when you forget it yourself.
“Don’t let doubt fester. One text can change your whole day.”
✅ Tip: Identify 3–5 people you can lean on. Don’t wait until you’re in crisis mode to connect.
Having a support system isn’t just nice—it’s necessary. Your posse keeps you grounded, focused, and encouraged when imposter syndrome kicks in. Melissa’s message: start building those relationships now, not just when things get tough.
🚀 5. Stay Curious, Stay Learning
From AI to personal development to cooking sea bass (long story 😆), Melissa’s advice is to keep learning—no matter how big or small the topic.
“Constant learning keeps your brain fresh, your mindset growing, and your creativity alive.”
✅ Tip: Make it a habit to learn one new thing every week—professionally or personally.
Curiosity opens doors and builds confidence. Even small wins—like trying something new—can reignite your sense of purpose. Melissa says staying curious is one of the most underrated superpowers in today’s ever-changing workplace.
🎓 Want More from Melissa?
Melissa is launching two powerful professional development cohorts in May:
Executive Essentials (5-week course) – Starts May 7
Executive Essentials Accelerator (4-week course) – Starts May 8
If you’re ready to reinvent, reengage, or restart your career path, these courses are an incredible way to invest in yourself.→ Learn more and sign up here
They’re designed to take the concepts we discussed in this episode and bring them to life through practical tools, community support, and focused coaching. Whether you’re transitioning roles or rediscovering what lights you up, Melissa’s cohorts are built to meet you where you are. Spots are limited, so don’t wait!
🎵 Listen to the Full Episode
Whether you're listening on your morning walk or lunch break, there's something in this episode for everyone. It's a must-listen if you're navigating change, burnout, or just need a spark. And yes, you’ll laugh too—we keep it real.
Feeling stuck? You’re not alone. But as Melissa says—confidence, network, risk, passion, and fun—that’s the career cocktail we should all be sipping. 🍸
Comments