Milestone Moments in Business & Leadership

What if the career you've been chasing on the side is actually the one you were meant to do full time?Richard Wilmore, award-winning talk show host and founder of Make Your Day Richer, LLC, spent 30 years treating his passion as a side gig while running everything from a mobile fashion truck to a cancer arts nonprofit. Then one pivotal decision changed everything.What finally made him stop running from what he was born to do? And what's the one thing holding most entrepreneurs back from getting the visibility they deserve?Richard reveals why so many experts with powerful stories never get heard, and what separates those who break through from those who stay invisible. His answer might surprise you.Listen in to learn more about building confidence as an entrepreneur, turning your passion into a full-time career, and getting booked on podcasts to grow your brand.To connect with Richard Wilmore, visit makeyourdayricher.comStay connected! Subscribe to Sheila's newsletter for: Early access to upcoming episodes and events Expanded strategies and resources Direct connection with Sheila for questions and supportSubscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect with me on LinkedIn: https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestones For more information, visit: https://fivemilestones.com/show/ Sponsored by: https://PodToBook.ai | Turn Your Podcast Conversations into a Book

What if the moment your plans fall apart is really the start of someone you haven't met yet?Becky Kenrick spent more than 20 years in accounting and finance, then watched the future she had planned disappear almost overnight. As a single mother, she had to figure out who she was beyond everyone else's needs. Today she helps women find more clarity, confidence, and agency in their own lives.In this episode, Becky shares what she kept hidden behind a strong face, the reframe that changed how she saw the hardest season of her life, and an unexpected moment that showed her a gift she had been overlooking. What did she do with it next?If you're in the middle of a reset, or you're supporting someone who is, press play. Listen in to learn more about rebuilding after divorce, financial confidence, and starting over with purpose.Tune in to the full episode now.To connect with Becky Kenrick, visit [Becky's website]Stay connected! Subscribe to Sheila's newsletter for:Early access to upcoming episodes and eventsExpanded strategies and resourcesDirect connection with Sheila for questions and supportSubscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect with me on LinkedIn: https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestonesFive Milestones: https://fivemilestones.com/show/Sponsored by: https://PodToBook.ai | Turn Your Podcast Conversations into a Book

What if the thing holding your career back isn't a lack of options, but a loss you never had room to feel?Rachel Yance spent more than two decades as a nurse. Today she is a health and life coach, sound healer, and yoga teacher, and she is training as a grief facilitator. Along the way, burnout and loss collided in ways she never expected.In this episode, Rachel opens up about what finally made her rethink everything, the simple everyday practice that helped her move again, and a session she entered looking for career clarity that took a turn she never saw coming. What did she walk away knowing for the first time?Listen in to learn more about healing grief, recovering from burnout, and changing careers with confidence.Stay connected! Subscribe to Sheila's newsletter for:Early access to upcoming episodes and eventsExpanded strategies and resourcesDirect connection with Sheila for questions and supportSubscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect with me on LinkedIn: https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestonesFive Milestones: https://fivemilestones.com/show/Sponsored by: https://PodToBook.ai | Turn Your Podcast Conversations into a Book

What happens when the career you spent 25 years building suddenly disappears on someone else's terms?Janylene was a senior HR executive leading mergers, transformations, and national teams. Then one meeting changed everything. Her calendar emptied overnight, and a thought she'd been avoiding finally surfaced.Three days later, she walked into an interview for another VP role and froze. Not because she wasn't qualified, but because something deeper was happening. What she realized on the walk home in the rain became the turning point she never saw coming.What was the "missing link" she discovered? Tune in to hear the full story.To connect with Jenny Lane Turcotte, visit hypnocoach.caStay connected! Subscribe to Sheila's newsletter for:Early access to upcoming episodes and eventsExpanded strategies and resourcesDirect connection with Sheila for questions and supportSubscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect with me on LinkedIn: https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestones For more information, visit: Five Milestones: https://fivemilestones.com/show/ Sponsored by: https://PodToBook.ai | Turn Your Podcast Conversations into a Book

What do you do when the identity you spent years building suddenly can't carry you down the stairs?Alice Cunningham was a thriving litigator, a Barre3 instructor, and a healthy woman in her early 30s. Then one ordinary night, something felt off. She brushed it off. By morning, everything had changed.In this episode, Alice opens up about the moment she realized she was wrong about what was happening, the one thing that proved harder than physical therapy, and the emotion that surfaced mid-conversation that she didn't see coming.If you tie your worth to your work, this conversation may change how you face your next setback. Press play to hear what happened next.Tune in to the full episode now.To connect with Alice Cunningham, visit [Alice's website]Stay connected! Subscribe to Sheila's newsletter for:Early access to upcoming episodes and eventsExpanded strategies and resourcesDirect connection with Sheila for questions and supportSubscribe to the Newsletter: https://fivemilestones.kit.com/newsletterConnect with me on LinkedIn: https://www.linkedin.com/in/sheilaslick/Subscribe on YouTube: https://www.youtube.com/@fivemilestonesFive Milestones: https://fivemilestones.com/show/Sponsored by: https://PodToBook.ai | Turn Your Podcast Conversations into a Book